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Tag: Founders

  • These Are the Biggest Founder Comebacks of 2025

    Everyone loves a good comeback story, but the definition of comeback can vary significantly, especially in the startup world. In some instances, a comeback is the return of a founder to the business he or she left or was forced out of, helping it to recapture the spark that made it a success. In others, it’s a calculated change in direction that helps keep a company relevant when things look dire. Here are some of the most notable comebacks from this year.

    Kevin Rose, Digg

    Rose co-founded Digg, a repository of Internet links, in 2004. It quickly became a must-visit site, with users upvoting and downvoting the stories they liked and loathed the most. (That formula is now a common one at many websites.) Digg grew to an estimated worth of $160 million by 2008. A 2010 redesign was so unpopular, however, that the audience migrated over to Reddit (which offered a similar upvote/downvote functionality). Rose sold the company in 2012.

    Earlier this year, though, Rose and his one-time rival Reddit co-founder Alexis Ohanian, bought Digg with plans to revive it. Backed by True Ventures (where Rose is a partner) and Ohanian’s Seven Seven Six, the revived Digg aims to provide a human-centered experience in the age of AI.

    “In the current social media landscape, community discourse has grown increasingly combative, cluttered, and exhausting,” the two said in announcing the deal. “Users are bogged down by misinformation, spam, and the emotional toll of navigating hostile interactions. The upcoming relaunch of Digg is offering a solution.”

    Anne Wojcicki, 23andMe

    Wojcicki’s comeback might be one of the fastest on record as well as one of the most controversial. The 23andMe co-founder resigned as CEO in March of this year when the company filed for Chapter 11 bankruptcy (though stayed on as a member of the board). That bankruptcy of the company, which was once valued at $6 billion, followed a 2023 hacking incident that raised several concerns about the company. (The hackers, in one online post that offered data for sale, bragged of having a huge database of Ashkenazi Jews, including people whose ties with that ancestry are less than 1%.) Customers were also concerned that their DNA could be sold to a third-party company without their consent during the bankruptcy. 

    Wojcicki first offered to buy the company in mid-2024. The 23andMe board rejected her bid to take the company private, later quitting en masse. In June, though, TTAM, a nonprofit run by Wojcicki, agreed to buy the genetic testing company for $305 million. “I am thrilled that TTAM Research Institute will be able to continue the mission of 23andMe to help people access, understand and benefit from the human genome,” Wojcicki said in a statement at the time. She has since resumed her role as CEO.

    Ty Haney, Outdoor Voices

    Haney left Outdoor Voices five years ago, amid growing pains at the direct-to-consumer apparel brand. In July, whispers of her return were confirmed, along with news that she was now also a partial owner and partner. While her main focus will still be her brand loyalty rewards platform, Try Your Best, she told Inc. earlier this year that she believed she could win back the trust of Outdoor Voices customers and draw in a younger customer base as well. And the key might be having the two companies work together.

    “It feels very full circle and obvious for OV to step into TYB,” she said. “At Outdoor Voices, we had such a strong community, and it became one of our most profitable and productive growth channels. That said, we didn’t have a tool to make those efforts scalable and measurable. … When you engage closely in this way with your best customers, it does increase their value over time.” 

    Parag Agrawal, Parallel Web Systems

    The former CEO of Twitter, who was fired by Elon Musk in 2022, resurfaced this year with the launch of Parallel Web Systems, which aims to let AI systems conduct reliable, real-time research online. The company was quietly founded in 2023, but debuted its first products in August and secured a Series A round of $100 million in November, which valued Parallel at $740 million. (The round was co-led by Kleiner Perkins and Index Ventures, with existing backers, including Khosla Ventures, also taking part.)

    Pinky Cole, Slutty Vegan

    Cole temporarily lost control of her company earlier in 2025 due to a restructuring that followed a number of financial issues, including $20 million in debt. She wasn’t ready to give up on it, though. One month after she was kicked out, she reacquired full ownership of the fast-casual brand, using an LLC called “Ain’t Nobody Coming to See You, Otis.” Slutty Vegan 2.0 is a leaner company, with six locations instead of 18 and a new focus on franchising and plans for a global expansion. 

    “People love Slutty Vegan because they love me, and I used to not tap into that, but I 1764371429 know I have a superpower with people,” she told People magazine. “People love me, so I know that people are going to support and back me in whatever it is that I authentically do.”

    The final deadline for the 2026 Inc. Regionals Awards is Friday, December 12, at 11:59 p.m. PT. Apply now.

    Chris Morris

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  • Founder of $100 million company never unplugs from work, but encourages her team to have work-life balance: ‘They didn’t sign up to be entrepreneurs’ | Fortune

    Founders can find it hard to step away from work when their company rests on their shoulders. The concept of having “work-life balance” has sparked fierce debate among entrepreneurs, who question if it’s even possible to have the best of both worlds: scaling a multimillion-dollar business, with enough downtime to recharge. Two-time founder Nicole Bernard Dawes is a strong advocate of unplugging from the job—but only for her employees. 

    “I think I probably am a little bit of a hypocrite, because I don’t unplug. I never do,” Dawes tells Fortune. “I never want to be the person that’s holding up a member of our team.”

    The serial entrepreneur encourages her staffers to totally disconnect from work once they’re off the clock, but doesn’t give herself the same breathing room. Having scaled two companies to success, she’s assumed the responsibility of always being on for decades. Dawes first founded organic, non-GMO tortilla chip brand Late July in 2003, which currently lines the aisles of Targets, Whole Foods, Krogers, and Walmarts across the country. Campbell’s acquired a majority stake of the business in 2014, eventually buying the rest of the $100 million company in 2017. In 2018, Dawes broke into another consumer packaged goods (CPG) market again, this time with zero-sugar, sustainably packaged soda line Nixie. The brand raised $27 million in new funding earlier this year, with its products being sold in over 11,000 major grocery stores. 

    With more than two decades of entrepreneurship under her belt at Late July, Dawes had pushed through economic downturns and many sleepless nights. But the hardships didn’t stop her from returning to the startup scene as Nixie’s founder—having grown up in the business world, Dawes is not so easily deterred. However, she doesn’t want work to overtake her staffers’ lives.

    “I signed up for this. I am the entrepreneur, I did this to myself—a self-inflicted situation. [My employees] didn’t sign up to be entrepreneurs,” Dawes says. “I am very comfortable taking downtime, but also making sure I’m available.”

    Dawes says never unplugging is “my life”—and she grew up in it

    Many leaders out there, like Google cofounder Sergey Brin, expect their staffers to clock in more than the typical nine-to-five job. But Dawes doesn’t hold her her employees to have the relentless work-ethic of entrepreneurs who pride themselves on having no personal lives. 

    “I think that where a lot of [leaders] differ, is extending that to their team. I feel very strongly that it should not extend to the team,” Dawes explains. “But I also feel like that is how I grew up. My father missed a lot of stuff because he felt like that was what you had to do. So I was determined I wasn’t gonna do that. I wanted to be present at things for my kids, and I wanted [it] to be okay for our team to be that way, too.”

    Dawes witnessed the pitfalls of entrepreneurship as a kid growing up in her parents’ food businesses. She spent her childhood years working the front counter of her mother’s health-food store, and roaming the floors of her late father’s $4.87 billion snack empire: Cape Cod Chips. As a kid in a family running two businesses, Dawes says it could be difficult for her parents to step away from the job. So when she decided to follow in their footsteps as a two-time founder of successful CPG brands, she knew exactly what to expect. 

    “When you decide to become an entrepreneur, there’s a lot of people [saying], ‘It’s stressful, it’s lonely, it’s all these things.’ And that’s true, but this is where I was really fortunate: I grew up in this business, so I entered eyes wide open,” Dawes says. “That’s why it’s really important to be passionate about your mission, passionate about your products. Because you do have to sacrifice a lot on the other side.”

    Dawes still makes time for the important things

    While Dawes admits she has difficulty stepping away from the grind, she still makes time for the things that keep her sane. 

    “You have to choose what’s the most important thing in that moment. I don’t think as an entrepreneur—at least for me—I’ve never really, truly, been able to shut off completely,” Dawes says. “But I also make time to have family dinner almost every night. There were things that were priorities to me, and I still make them priorities, like going out for a walk every day or exercising.”

    The entrepreneur also loves hitting the beach, reading, and cooking—and despite it feeling like a chore to many, Dawes really enjoys going to the grocery store. She calls it her “hobby”: observing what new products are stocked on shelves, and what items shoppers are gravitating towards. It’s gratifying to witness people pick up a bag of Late July or a case of Nixie drinks to bring home to their families, something she feels immensely grateful for. While getting her brands into those grocery aisles has been no easy feat, it’s all been worth it in the end. Dawes says passion is what eases the weight of her work-life balance. 

    “Sometimes when I wake up in the morning like, ‘I can’t even believe I’m this lucky that I get to do this job,’” Dawes says. “And because I feel that way, it doesn’t feel like working. I’m getting to do something fun all the time.”

    Emma Burleigh

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  • 6 Startups That Found Buyers in 2 Years or Less

    Setting a business up for a successful exit usually takes a while. Whether a company files for an initial public offering or receives a compelling buyout offer, it generally has to first spend several years building a solid customer base. But every now and then, startup founders cash out quickly.

    Selling a company isn’t everyone’s measure of success. Some founders aim for a different exit or launch a company with no intention of leaving it. Others might want to stay around, but investors push for an exit to see returns on their money.

    Still, a select group of entrepreneurs have been able to sell their startups for substantial payouts before those businesses hit their second birthday. That’s especially noteworthy as many founders don’t tend to stick around a business for the long term. A Harvard Business Review study from several years ago found that less than half of founder/CEOs continue to run the business after three years and fewer than 25 percent are in charge when a company goes public.

    Perhaps even more striking is the fact that most of the companies that have achieved this rare feat are still either around or have become a key part of their new parent company.

    Chad Hurley, Steve Chen, and Jawed Karim: YouTube

    Hurley, Chen, and Karim founded YouTube in February 2005 – on Valentine’s Day. Within nine months, the site had hosted a video that collected one million views. While it wasn’t the first video sharing site (Vimeo had been founded the year before), it quickly went viral – and the uploading of Saturday Night Live’s “Lazy Sunday” sketch sealed that. On November 13, 2006, YouTube was purchased by Google for $1.65 billion, a record-breaking amount at the time.

    Kevin Systrom and Mike Krieger: Instagram

    Systrom was a Google employee when he built the forerunner to Instagram called Burbn. Krieger was an enthusiastic user of that app and the two eventually began working together to create what would become Instagram. The company was formally founded on Oct. 6, 2010. Meta (then Facebook) bought it for $1 billion on April 9, 2012.

    Stewart Butterfield and Caterina Fake: Flickr

    Founded in February 2004 by Butterfield and Fake, Flickr made its debut at the O’Reilly Emerging Tech conference in San Diego. Originally engineered as part of a multiplayer online game, the site evolved and made photo sharing a common online activity. By the following March, Yahoo acquired the company for $35 million, helping it to scale its infrastructure to keep up with demand. Butterfield would go on to found office communication tool Slack.

    Sabeer Bhatia and Jack Smith: Hotmail

    Smith, who was an Apple employee, came up with an idea for anonymous web-based email, teaming up with a coworker Bhatia to launch Hotmail on July 4, 1996. Microsoft liked what it saw and made a $400 million offer the following December, incorporating it into the Windows live suite of products. The service was eventually incorporated into Outlook.com.

    Mark Pincus: Freeloader.com

    Freeloader was one of the first “push” software sites, offering free games to users, supplemented by advertising. Pincus founded the startup in 1995 and found a buyer just seven months later: Individual Inc., which paid $38 million for the company. Changes in the advertising market led to the company shutting down the site in 1997. Pincus stayed a part of the gaming, eventually launching Zynga in 2007, which he took public in 2011 (and which is now a part of Take-Two Interactive Software).

    Marc Lore: Jet

    Lore had some experience with exits when he founded this retail site. He had already sold his startup Diapers.com to Amazon for $545 million. But when he launched Jet.com in April 2014, something clicked. In 2016, Walmart bought Lore out, paying $3.3 billion for Jet in hopes of expanding its e-commerce arm. Four years later, it shut Jet.com down and phased out the brand, but CEO Doug McMillon said Jet had helped Walmart jump-start the progress it had made with its online retail business in that time. Lore continued to work with the retail giant through 2021.

    Chris Morris

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  • The CEOs of Apple, Airbnb, and PepsiCo agree on one thing: life as a business leader is incredibly lonely | Fortune

    Being CEO has its many perks: Business leaders get to command the world’s most powerful companies, shape their legacies as pioneers of industry, and enjoy hefty billion-dollar paychecks. But in the steep climb up the corporate ladder, many won’t notice all the peers left behind until they’re looking down from the very top. It can be a lonely, solitary job.

    Leaders at some of the world’s largest companies—from Airbnb and UPS to PepsiCo and Apple—are finally opening up about the mental toll that comes with the job. As it turns out, many industry trailblazers are grappling with intense loneliness; at least 40% of executives are thinking of leaving their job, mainly because they’re lacking energy and feel alone in handling daily challenges, according to a Harvard Medical School professor. And the number could even be higher: About 70% of C-suite leaders “are seriously considering quitting for a job that better supports their well-being,” according to a 2022 Deloitte study. 

    To ward off feelings of isolation, founders and top executives are stepping outside of the office to focus on improving their well-being. Toms founder Blake Mycoskie struggled with depression and loneliness after scaling his once-small shoe business into a billion-dollar behemoth. Feeling disconnected from his life’s purpose and that his “reason for being now felt like a job,” he went on a three-day men’s retreat to work on his mental health. And Seth Berkowitz, the founder and CEO of $350 million dessert giant Insomnia Cookies, cautions bright-eyed entrepreneurs the gig “is not really for everyone.” 

    “It can be lonely; it’s a solitary life. It really is,” Berkowitz recently told Fortune.

    Brian Chesky, cofounder and CEO of Airbnb

    Eugene Gologursky / Stringer / Getty Images

    Airbnb’s cofounder and CEO Brian Chesky is one the most outspoken leaders in the business world waving the red flag on loneliness. Chesky described having a lonely childhood, pulled between his love for creative design and sports, never really fitting in. But his mental health took a turn for the worse once assuming the throne as Airbnb’s CEO. His other two cofounders—who he called his “family,” spending all their waking hours working, exercising, and hanging out together—were suddenly out of view from the peak of the C-suite. 

    “As I became a CEO I started leading from the front, at the top of the mountain, but then the higher you get to the peak, the fewer the people there are with you,” Chesky told Jay Shetty during an episode of the On Purpose podcast last year. “No one ever told me how lonely you would get, and I wasn’t prepared for that.”

    Chesky recommends budding leaders actually share their power, so no one shoulders the mental burden of entrepreneurship alone. 

    “I think that ultimately, today, we’re probably living in one of the loneliest times in human history,” Chesky said. “If people were as lonely in yesteryear as they are today, they’d probably perish, because you just couldn’t survive without your tribe.”

    Indra Nooyi, former CEO of PepsiCo

    Jemal Countess / Stringer / Getty Images

    Leaders at Fortune 500 giant PepsiCo face constant pressure from consumers, investors, board members, and their own employees. But it’s also tough to vent to peers who may not relate to—or even understand—the trials and tribulations of running a $209 billion company. Indra Nooyi, the business’ former CEO, said she often felt isolated with no one to confide in.

    “You can’t really talk to your spouse all the time. You can’t talk to your friends because it’s confidential stuff about the company. You can’t talk to your board because they are your bosses. You can’t talk to people who work for you because they work for you,” Nooyi told Kellogg Insight, the research magazine for Northwestern’s Kellogg School of Management, earlier this year. “And so it puts you in a fairly lonely position.”

    Instead of divulging to a trusted friend or anonymously airing out her frustrations on Reddit, Nooyi looked inward. She was the only person she could trust, even if that meant embracing the isolation. 

    “I would talk to myself. I would go look at myself in a mirror. I would talk to myself. I would rage at myself. I would shed a few tears, then put on some lipstick and come out,” Nooyi said. “That was my go-to because all people need an outlet. And you have to be very careful who your outlet is because you never want them to use it against you at any point.”

    Carol Tomé, CEO of UPS

    Kevin Dietsch / Staff / Getty Images

    Before Carol Tomé stepped into the role of the CEO of UPS, she was warned the top job goes hand-in-hand with loneliness. The word of caution didn’t phase her—at least, not at first. But things changed when she actually took the helm of the $75 billion shipping company. 

    “I would say, ‘How lonely can it really be? It can’t be that lonely?’ What I’ve since learned is that it is extraordinarily lonely,” Tomé told Fortune last year. 

    “When you are a member of an executive team, you hang together…Now, my executive team will wait for me to leave a meeting so that they can debrief together. It’s the reality and you have to get used to it. But it is super lonely.”

    Tim Cook, CEO of Apple

    NurPhoto / Contributor / Getty Images

    Apple CEO Tim Cook isn’t immune to the loneliness that often comes with the corner office. More than 14 years into his tenure, he’s acknowledged his missteps, which he called “blind spots,” that have the potential to affect thousands of workers across the company if left unchecked. Cook said it’s important for leaders to get out of their own heads and surround themselves with bright people who bring out the best in them. 

    “It’s sort of a lonely job,” Cook told The Washington Post in 2016. “The adage that it’s lonely—the CEO job is lonely—is accurate in a lot of ways. I’m not looking for any sympathy.”

    Seth Berkowitz, founder and CEO of Insomnia Cookies

    Courtesy of Insomnia Cookies

    Entrepreneurship can be a deeply fulfilling and rewarding journey: an opportunity to trade a nine-to-five job for a multimillion-dollar fortune, if all the right conditions are met. And while Insomnia Cookies’ Seth Berkowitz loves being a CEO and all the responsibilities that come with it, he cautioned young hopefuls about the weight of the career. He, like Cook, advises aspiring founders to counter loneliness with genuine, meaningful connections.

    “It can be lonely; it’s a solitary life. It really is. [During] the harder times, it’s very solitary—finding camaraderie, mentorship, some sense of community, it’s really important,” Berkowitz recently told Fortune. “Because I go so deep, it’s sometimes hard to find others and let them in.”

    Emma Burleigh

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  • How Blueland’s Founders Avoided the ‘Founder Divorce’ That Kills 65% of Startups

    Since my co-founder John Mascari and I started Blueland, we’ve only had one real disagreement—what to name the company. That was seven years ago. Since then, we’ve made thousands of decisions that matter far more. Somehow, we’ve managed to stay aligned. 

    That doesn’t mean we see everything the same way. We approach problems from different angle, and we ask different questions. However, we’ve built a partnership grounded in trust—trust in the other’s ownership and trust that the other person cares as deeply, works as hard, and sweats the details just as much. 

    Co-founder conflict is one of the top reasons startups fail 

    Research from Harvard Business School shows that around 65% of startups fail because of co-founder conflict or misalignment. “Founder divorce” is one of the most common but least-discussed risks in building a company. You can have the right idea, funding, and timing, and still fail because your partnership breaks down. From day one, we knew that if we wanted to build something durable, we’d have to protect alignment as deliberately as we protect cash flow. 

    How we work together 

    From the start, we divided responsibilities loosely by strength. For example, I tend to lead on marketing, brand, and creative. He focuses more on operations, finance, and our people. Those boundaries, however, aren’t walls. We both deeply co-own our mission and product philosophy. We both jump into anything that touches the customer or the planet. We talk nearly every day—sometimes about the biggest strategic calls and sometimes about the smallest details. 

    We each care deeply about the details. Knowing the other does the same is what makes trust possible. When he makes a call on a supplier, I don’t need to double-check it because I know it was made with as much care as if I had made it myself—never out of convenience or lack of time. When I do double-check, it’s welcome. We’ve built enough trust that questions never feel like second-guessing. We both know any push or challenge comes from the same place — wanting to get to the right answer for the company. 

    That kind of trust actually makes it easier to challenge each other, not harder. It’s a habit the broader team sees and mirrors. When people watch founders question each other with respect and curiosity, it sets the tone for how the whole company communicates. 

    Revisiting our North Star every year 

    From the beginning, we take a step back to reset once a year. Together with our board and leadership team, we set a North Star—a theme or focus for the year. Then, we define each leader’s priorities that will bring it to life. 

    We also revisit our company values to make sure they still feel true to how we operate. Next, we share the theme with the full company. It keeps everyone anchored and keeps us accountable. 

    When everyone knows the focus, it’s easier to see when decisions start to drift away from, including our own. That discipline around alignment isn’t just for founders. It scales across the organization. 

    Staying aligned in practice 

    Alignment doesn’t happen by luck. It’s maintained through constant communication. We check in daily—sometimes formally, sometimes between meetings or flights—to trade notes, flag concerns, or pressure-test each other’s thinking. If something feels off, we don’t wait. We speak up immediately. It’s rarely dramatic, but this habit has prevented countless small misalignments from becoming bigger ones. 

    What makes it work 

    • Shared ownership of purpose
      We both care about why the company exists and what we refuse to compromise on. 
    • Equal respect for detail
      We trust each other because we both do the work and commit to the details. 
    • Constant communication
      We don’t wait for formal check-ins to reconnect. 
    • Regular re-alignment
      Revisiting the North Star each year keeps decisions consistent and our focus transparent. 
    • Assuming good intent
      Every disagreement starts from the belief that we’re both trying to do what’s best for the company and the mission. 
    • A shared desire to keep learning
      We both approach the business with curiosity. There’s always more to understand, questions to ask, and new ways to make Blueland stronger. 

    The real takeaway 

    People sometimes hear that we’ve only had one major disagreement and assume that means we never debate. It’s the opposite. We question everything. We just do it from a place of total trust. The goal isn’t to avoid conflict. It’s to build a partnership where you know the other person cares as much as you do. 

    The opinions expressed here by Inc.com columnists are their own, not those of Inc.com.

    Sarah Paiji Yoo

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  • Here’s what it’s really like to appear on billionaire VC Tim Draper’s ‘Meet the Drapers’ pitch show | TechCrunch

    There was barely a breeze on the roof of the MCM studios building in Manhattan last week as six entrepreneurs graced a stage to pitch their businesses.

    At one point, it was April Wachtel’s turn. She stood and made the case for her company, Cheeky Cocktails, to a judging panel that included the billionaire venture capitalist Tim Draper. Men holding TV cameras circled her as she pitched, capturing the moment live for Draper’s “Shark Tank”-style business competition show “Meet the Drapers.” 

    The show is entering its eighth season, with past winners including the leadership platform Balloon and the food company It’s Skinny. 

    After the show, Wachtel told TechCrunch the experience was a “whirlwind” and said the exposure is huge for startups like hers. Cheeky Cocktails offers a line of handcrafted cocktail mixers. She heard about the show after coming in second at another pitch competition earlier this month. A producer for “Meet the Drapers” reached out and asked if she was available to film, and less than two days later, she was pitching on the show. 

    “There’s no substitute for hearing a founder tell their own story,” she said. “At the end of the day, people might buy from you because they like you and then stick around because they love the product.”

    Tim Draper (CENTER) with the founders who appeared on the show “Meet the Drapers.”Image Credits:“Meet the Drapers”

    Last Monday, the show provided a behind-the-scenes look at how it’s made to selected media and guests. Draper told TechCrunch he wanted to offer a behind-the-scenes look at how investments are made. 

    His judging panel included his sister, Polly Draper, an actress best known at the moment for appearing in “Hacks.” Also on the panel were Andy Tang, a partner at Draper Associates, and Rosie Rios, who served as Treasurer of the United States from 2009 until 2016. 

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    The show is one of many on Draper’s newly launched television channel, DraperTV, which offers programming around business and entrepreneurship, available via streaming services like Roku. Previously, the show aired on channels like BizTV. 

    This season of the show travels throughout various cities in the U.S., such as Tuscaloosa, Alabama, Austin, and Detroit, tapping into local talent and highlighting different tech ecosystems. 

    Wachtel was one of six founders on the New York episode, the winners of which go on to the semifinal round against all the other city winners, and then the grand finale in San Francisco to vie for the $1 million prize. 

    “The idea was for people around the world to be able to see what the entrepreneurial and venture capital interaction looks like, and why it’s one of the best things for creating jobs and wealth and energy and consumer activity around the world,” Draper said. 

    The show had all the hallmarks of entrepreneurship and entertainment that viewers love. Draper has a big personality and knows when to poke fun at himself. The investors gave clear insights, and the founders came with grand visions. Everyone hailed from diverse ethnic and gender backgrounds and various careers in a myriad of industries. 

    Sujana Chandrasekhar, founder of the medtech KivviMed, partook in the same New Jersey pitch competition as Wachtel and also received a recommendation to audition for “Meet the Drapers.” Chandrasekhar said she was more nervous than usual while pitching on “Meet the Drapers,” especially knowing the show’s audience size. KivviMed is creating a medical device to help alleviate ear pain.

    I’ve created five digital twins. I’ve got my digital twin interviewing, like, Karl Marx.

    Draper said the show has a big viewership, specifically in India, Brazil, and Taiwan. DraperTV, launched last summer, reaches more than 350 million households throughout the world, according to stats the show provided.

    “I was able to stay focused and convey what I needed to convey and answer the questions as best as I could,” Chandrasekhar told TechCrunch. The show’s staff also helped prepare her, she said. They helped her hone her pitch, did a tiny walking tour of New York with the founders, and provided hair and makeup, which, she said, made her feel special. 

    “The exposure that our company and vision receives is outstanding,” she added about why she chose to participate.

    Hilary Taylor, the founder of WattsUp, agreed. WattsUp is a startup that created electric vehicle infrastructure. Taylor found out about the show through the Techstars Alabama Accelerator program, of which her company is currently a part. 

    She called the show engaging and challenging, saying it was just as much about storytelling as it was business. 

    “You have to connect with viewers and judges in a very short window, simplifying complex technology for a mainstream audience while still sounding credible to investors,” she continued, adding that the show helps early-stage founders connect with those beyond the tech bubble. 

    “Unlike the buttoned-up feel of many VC pitch rooms, this one had candid, funny, even goofy moments that made it feel human and unexpectedly fun,” she said. 

    “Meet the Drapers” is only one part of a larger Draper media empire being built. Draper himself is a third-generation investor (after his famed father and grandfather) and, in the 1980s, founded Draper Associates, a venture firm that has backed some of the biggest names in tech, like Tesla, Skype, and Twitch. His children have also entered the family venture capital business, including Jesse Draper, founder of Halogen Ventures, and Adam Draper, founder of Boost VC. 

    It’s clear Draper has big ambitions for his tech and startup-focused media empire. DraperTV offers shows like “Draper Decentralized,” about AI and web3; the “Can’t Be Done” podcast, about emerging technology; and “Talk with Tim,” in which Draper shares his perspectives about business and technology. 

    There’s no substitute for hearing a founder tell their own story.

    He’s also building digital twins: AI versions of himself that can interact with people and even conduct interviews. He believes digital twins will become a more significant part of entertainment, media, and news, though added humans will still play a big role in news development. 

    “I’ve created five digital twins,” he said. “I’ve got my digital twin interviewing, like, Karl Marx.” 

    Beyond his TV network, Draper is still running Draper University, a program that has, at times, used unconventional methods to train entrepreneurs on how to survive in the startup-world jungle. For instance, one of his first forays into reality TV was a show based on Draper University called “Startup U,” which was quickly canceled after one season. But Draper said he still likes the premise and hasn’t ruled out making another, similar attempt.

    “We’ve done some extraordinary things with entrepreneurs, and it has made some very good videos and some very good storytelling,” he said. 

    Draper believes that the innovation these founders are building will be of greatest importance in the decades to come and that showcasing such talent now is a gateway for people to explore the future. On “Meet the Drapers,” that meant a sneak peek at how people are seeing the future of sports betting, how founders are looking to enhance drug discovery, and how electric vehicle infrastructure is about to see a shake-up. 

    “There are a few networks that are thinking about the future,” Draper continued. “They are all telling the story of what’s happening right now. We want the story of 15 years from now.”

    Dominic-Madori Davis

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  • How Conscious CEOs Can Transform Today’s Purpose Into Tomorrow’s Legacy

    This article is written by Kent Gregoire, an Entrepreneurs’ Organization member who is co-founder and CEO of Symphony Advantage, where he helps purpose-driven CEOs build regenerative operating systems for stakeholder value creation with his regenerative business readiness assessment.

    You’ve read the books, attended the conferences, and even restructured your company around a higher purpose. Yet here you are, wondering why your passionate commitment to making a difference feels like pushing water uphill. You’re not alone. After years of advising purpose-driven CEOs and being certified as the seventh person globally in Conscious Capitalism, I’ve witnessed a troubling pattern: Leaders with genuine intentions to create positive change often struggle to translate their purpose into lasting legacy. The problem isn’t your purpose. It’s the gap between what you build today and what remains tomorrow. 

    The great disconnect 

    Here’s what keeps conscious entrepreneurs awake at night: Despite their commitment to stakeholder capitalism and their investment in purpose-driven initiatives, they’re not seeing the transformational impact they envisioned. Employee engagement remains flat. Community partnerships feel transactional. The business grows, but the legacy doesn’t compound. 

    According to King’s Business School, while purpose-driven companies achieve growth rates triple those of their traditional counterparts, most CEOs report difficulty in translating purpose into measurable, lasting change. Companies that make strong commitments to purpose show up to three times the compound annual growth rate as their closest competitors. Yet the disconnect isn’t in the intention. It’s in the execution. 

    Think of purpose and legacy as two sides of the same coin. Purpose is what you build today through daily decisions, cultural choices, and stakeholder interactions. Legacy is what remains tomorrow—the systemic changes, transformed lives, and regenerative cycles that continue long after you’ve left the building. Most purpose-driven leaders focus intensely on one side of this coin while unconsciously neglecting the other. 

    The three legacy gaps 

    Through my work with conscious CEOs, I’ve identified three critical gaps that prevent purpose from becoming legacy: 

    • The measurement gap. You measure profit meticulously but treat impact anecdotally. While you track revenue to the penny, stakeholder value creation remains a feel-good story rather than a managed metric. What gets measured gets done, and what gets done repeatedly becomes legacy. 
    • The integration gap. Your purpose lives in mission statements and annual reports but hasn’t infiltrated your operating system. It’s an add-on rather than the engine. Legacy emerges when purpose drives every decision, from hiring practices to supply chain choices, from product development to community engagement. 
    • The regeneration gap. You’re focused on doing less harm when you should be creating systems that generate increasing good. Legacy isn’t built through sustainability alone. It’s built through regenerative practices that create expanding circles of positive impact. 

    The shift from purpose to legacy requires evolving from an extractive mindset to a regenerative one. Traditional business extracts value from stakeholders to concentrate it for shareholders. Conscious business seeks to optimize value creation across all stakeholders. However, legacy-building requires something more. It requires regenerative business practices that create expanding value for all stakeholders simultaneously. 

    Consider Ray Anderson of Interface, who in 1994 experienced what he called a “spear in the chest moment” after reading Paul Hawken’s The Ecology of Commerce. He unilaterally transformed Interface from a traditional carpet manufacturer into a restorative enterprise, setting ambitious goals that seemed impossible at the time. By 2022, Interface had achieved carbon neutrality, reducing carbon emissions by 96 percent along the way. The company that started as an industrial polluter now leads Climate Take Back, creating regenerative systems that continue expanding positive impact long after Anderson’s passing in 2011. 

    Consider Patagonia, whose founder, Yvon Chouinard, shocked the business world in 2022 by giving away the entire $3 billion company to fight climate change. Here’s what matters for legacy: Patagonia’s purpose-driven approach generated consistent growth from $270 million in 2008 to over $1 billion annually by 2017, while maintaining an employee turnover rate of just 4 percent, compared with the industry average of 20 percent. The company achieved a B Corp score of 151.4, nearly triple the median score of 50.9. This isn’t sacrifice. It’s a regenerative business creating compound value. 

    Also, consider Miren Oca of Ocaquatics Swim School in Miami, who transformed a single-mother’s survival strategy—teaching swimming lessons—into a regenerative legacy machine. Starting in backyard pools in 1994, she built a company that now delivers 250,000 swim lessons annually across five sustainable facilities. However, here’s the regenerative twist: In 2024, Oca transitioned Ocaquatics into one of only 50 Employee Ownership Trusts in the United States, making her 165 team members the owners. As the world’s first B Corp-certified swim school, Ocaquatics doesn’t just teach swimming. It builds community wealth, reduces drowning rates, and creates expanding circles of environmental and social impact. This is what happens when purpose compounds: a swimming instructor becomes a force for generational change. 

    The lesson is clear. Purpose, on its own, is not enough. Legacy emerges when leaders close the gaps by measuring impact as rigorously as profit, integrating purpose into the core of your operations, and shifting from sustainability to regeneration. When you build systems that create expanding circles of value, your influence compounds far beyond quarterly results. The question is not whether your business will make a difference. It already does. The question is whether it is a difference-maker that will endure. Purpose is what starts the journey, but legacy ensures it continues to move the world forward. 

    The opinions expressed here by Inc.com columnists are their own, not those of Inc.com.

    Entrepreneurs’ Organization

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  • Why New Startup Founders Are More Optimistic Than Established Entrepreneurs

    Despite continued uncertainties about the bottom-line impact of tariffs, and lingering doubts about the economy’s health, polls have shown small business owners’ optimism has risen since the the beginning of the year. Now, new data indicates the confidence of more recent founders is even higher than the generally improving outlook of more established entrepreneurs.

    The upbeat expectations of relatively newer small business owners were captured in a recent survey by email, social media, and digital marketing platform Constant Contact. Its polling of nearly 1,600 entrepreneurs showed founders who launched their companies within the last two years expressed higher levels of optimism about growing their businesses over the next three months than the average of all survey respondents. Leaders of those younger firms were also markedly more confident about the near-term future than respondents whose businesses have operated for a decade or more.

    For example, while 29 percent of all participating founders said they expected to increase headcount in the next quarter, 41 percent of those who launched their companies less than 24 months ago said they planned on hiring within that period. By contrast, just 21 percent of business owners with 10 years’ experience or more thought they’d be able to hire new employees over the next three months.

    Moreover, 76 percent of business owners who launched less than two years ago and now have 100 employees or more said they plan to make new hires in the next three months. According to Constant Contact CEO Frank Vella, more recent entrepreneurs’ higher confidence partly reflects the vigor and positivity of leaders whose companies are still benefitting from early-stage growth.

    “For many this optimism isn’t just a feeling; it’s a reflection of their current growth trajectory,” Vella told Inc. in emailed comments. “Younger businesses are more likely to be hiring, and this rapid scaling imbues a greater confidence in their current position and trajectory. Many of these business owners are highly ambitious as well. They are actively scaling and investing in their future, which naturally fuels a more positive outlook.”

    Those upbeat views were also evident in respondents’ optimism about how they think their companies will perform over the next three months.

    While an average of 31 percent of all participants said they were “extremely confident” about how their business will fare over the next quarter, that figure rose to 41 percent among owners who’ve been in operation less than two years. It was even higher — 60 percent — for members of that more recent cohort with 100 employees or more. It then dropped to less than a quarter of entrepreneurs who launched more than a decade ago.

    Those differences in outlook, Vella says, may come down more recent founders still having the greater flexibility of younger companies to react the various business and economic challenges all small companies are confronting.

    “They were likely founded in the midst of the current economic landscape, which is defined by supply chain issues, rising prices, and general uncertainty,” Vella explained. “Because of this, their business models, supply chains, and marketing strategies were built from the ground up to withstand this volatility…They are accustomed to doing more with less and can adapt their plans without the inertia that can slow down a more established company. In this way they aren’t reacting to a ‘new normal’; this environment is their normal. That makes them structurally better positioned to navigate it.”

    That pliability of smaller businesses may also explain why their owners’ optimism of starkly contrasts the more somber views of corporate leaders. For example, the reading of the most recent Conference Board’s Measure of CEO Confidence survey came in at just 49 points — still in negative territory, despite a 15-point boost over the previous poll.

    By contrast, the National Federation of Independent Business’s recent monthly surveys have shown the confidence of member entrepreneurs steadily rising this summer. Constant Contact’s survey confirms that optimism among entrepreneurs, even as tariff and economic uncertainties weigh more heavily on corporate CEOs.

    Indeed, it found nearly a third of respondents saying now is “an extremely good time” to launch a new product. Meanwhile, nearly a quarter said they considered current market conditions beneficial for growing their companies by opening new physical locations.

    Asked if the higher optimism of more recently launched business founders might reflect an insouciance or naivete that more established business owners may have lost through the experience of tough times, Vella said he instead views their confidence rooted in their success in meeting today’s challenges.

    “These business owners haven’t experienced a more stable economic climate to compare today against, so they are less focused on what’s been lost and more focused on the opportunity directly in front of them,” Vella said. “So, rather than being naive, I’d say they are inherently adapted. They’ve built their businesses for the world as it is today, and that’s a powerful advantage that fuels their confidence and their capacity to grow.”

    Bruce Crumley

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  • CEO’s ‘Powerful’ Business Change Leads to 8-Figure Revenue | Entrepreneur

    “It’s always been my dream to be a CEO of a fashion brand,” Ginny Seymour, CEO of contemporary women’s fashion brand Aligne, tells Entrepreneur.

    Image Credit: Courtesy of Aligne. CEO Ginny Seymour.

    A fashion industry veteran who started her career as a contemporary buyer at Saks Fifth Avenue, Seymour had an opportunity to realize that goal with Aligne, originally founded by Dalbir Bains as a wholesale women’s fashion brand in London in 2020.

    Seymour envisioned a new era for Aligne — the brand could fill a white space she saw in modern women’s clothing: the need for design-led, wearable pieces at an accessible price point, delivered with an omnichannel approach.

    Related: 5 Things I Wish Someone Had Told Me Before I Became a CEO

    Seymour set out to make it happen, essentially “refounding” the company. She joined the business as managing director in 2022, relaunched Aligne under her vision in 2023 and was officially named CEO in 2024.

    Image Credit: Courtesy of Aligne

    “I felt partners [had to be] a huge part of the story.”

    During her first several years as CEO, Seymour focused on Aligne’s community building online and “design handwriting,” then branched out from a direct-to-consumer strategy to an omnichannel approach with U.S. retail partners.

    In fact, despite being a London-founded brand, Aligne sees a larger part of its business unfolding in the U.S., Seymour says.

    The CEO even recently relocated from London to New York to support the U.S. office and team as the brand continues its expansion.

    “ We’re still based in the UK, so I travel back and forth,” Seymour says. “London to me is our creative hub; it’s part of our DNA being a British brand. That’s super important to me and something we don’t want to lose. So we’re very much creatively driven out of London, but commercially driven out of the U.S.”

    Image Credit: Courtesy of Aligne

    Related: ‘We Got So Many DMs’: This 27-Year-Old Revamped Her Parents’ Decades-Old Business and Grew Direct-to-Consumer Sales From $60,000 to Over $500,000

    As a still relatively young British brand, Aligne gains validation with a U.S. audience through retailers that have loyal customer bases.

    “In  the UK, it’s easier to be direct-to-consumer only because the UK is much smaller and more attainable,” Seymour says. “But in the U.S., to resonate as the next contemporary brand that people should be looking at, I felt partners [had to be] a huge part of the story.”

    Aligne recently launched with Nordstrom, a retailer Seymour says she’d always hoped to partner with one day, after the company direct-messaged her to express its interest in the brand. Aligne is also available at Anthropologie.

    Image Credit: Courtesy of Aligne

    Related: Her Self-Funded Brand Hit $25 Million Revenue Last Year — And 3 Secrets Keep It Growing Alongside Her ‘Mischievous’ Second Venture: ‘Entrepreneurship Is a Mind Game’

    “There’s less visibility [into] the analytics and who your customer is. You have to really listen.”

    Despite the long-term goal to expand in retail, Seymour first prioritized understanding Aligne as a brand and its relationship to customers before tackling those partnerships, appreciating how important that strategy is for sustainable success.

    Whether you’re refounding a business that already exists or starting one from scratch, knowing who your customer is — and quickly — will make or break its growth.  ”And that’s easier said than done,” the CEO notes. “There are so many factors. With every iOS update, there’s less visibility [into] the analytics and who your customer is. You have to really listen.”

    Aligne’s target customers are “confident, working” women, and acknowledging what those consumers wanted in a clothing line helped guide the brand’s design shift and the direction of its collection, Seymour says.

    Related: This Is the Real Secret to Exceeding Your Customer’s Expectations

    Dialing into that customer base is paying off. Aligne ended its fiscal year in July 2025 with 56% year-over-year revenue growth and revenue approaching eight figures.

    Most of Aligne’s pieces are priced between $100 and $300. Although Seymour recognizes why some brands evolve into the “premium contemporary” space amid rising costs and tariff challenges, she says the company is committed to its accessible price point.

    Image Credit: Courtesy of Aligne

    “I quickly had to learn where I didn’t want to lean and how to make sure to get the support.”

    Being a CEO is a lot harder than Seymour thought it would be when she was 20 years old, she admits. But she appreciates how the job has allowed her to draw on her experience as a buyer, which demanded a “balance of art and science” much like the executive role does.

    “[There might be a] week that I’m so artistic and designing the concept and the line, and there’s other days where I’m definitely leaning into the science,” Seymour says. “But I quickly had to learn where I didn’t want to lean and how to make sure to get the support in those areas because a CEO wears so many hats.”

    Related: I Founded a $1.7 Billion Startup for Small Businesses — Here’s the Secret Every Entrepreneur Should Know

    One of the biggest lessons Seymour’s learned during her tenure as CEO so far is the value in listening to her instincts — even when it’s difficult. Over the first couple of months of the company’s refounding, Seymour sometimes hesitated to say what she wanted, then didn’t get the results that she desired.

    “Three months in, I had this moment where I brought the team together and was much clearer about what I wanted,” Seymour says. “That brought them more on the journey with me, and it solidified us as a team and our values. If you have an idea and you’re building your own business, trusting your gut and not being scared to say it is powerful.”

    “It’s always been my dream to be a CEO of a fashion brand,” Ginny Seymour, CEO of contemporary women’s fashion brand Aligne, tells Entrepreneur.

    Image Credit: Courtesy of Aligne. CEO Ginny Seymour.

    A fashion industry veteran who started her career as a contemporary buyer at Saks Fifth Avenue, Seymour had an opportunity to realize that goal with Aligne, originally founded by Dalbir Bains as a wholesale women’s fashion brand in London in 2020.

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    Amanda Breen

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  • I Founded a $1.5 Billion Business. Here’s My Success Secret. | Entrepreneur

    This as-told-to story is based on a conversation with Shanaz Hemmati, COO and co-founder of ZenBusiness, a $1.5 billion company that provides an all-in-one platform helping small businesses become official, stay compliant, manage finances and more. Her co-founder is Ross Buhrdorf, who serves as CEO. The piece has been edited for length and clarity.

    Image Credit: Courtesy of ZenBusiness. Co-founder and COO Shanaz Hemmati.

    I always had an entrepreneurial spirit, but I never really thought about going off and starting my own business.

    At the University of Texas at Austin, I studied computer engineering, starting with hardware design before pivoting to software engineering. I truly love technology, and especially software engineering, because you’re coding to solve problems — I still love solving problems.

    Related: This Mom’s Creative Side Hustle Started As a Hobby With Less Than $100 — Then Grew Into a Business Averaging $570,000 a Month: ‘It’s Crazy’

    My husband’s an entrepreneur who’s always had his own businesses. He’d encourage me to start my own business, but I was too concerned. Sometimes women can think too hard about doing something; that’s what held me back from becoming an entrepreneur.

    For women in male-dominated fields, it’s important to seek out mentors who can help you from their experience, even if their journey looked different from yours. You can bounce ideas off them and ask them questions. Mentorship pushes you, but it also gives you assurance and confidence.

    Over the course of my career, I learned so much, which helped me when I made the leap to founder.

    “Small businesses are what keep the economy growing.”

    I first met my ZenBusiness co-founder Ross Buhrdorf when we worked at Excite.com, a web portal company founded in 1994. Several years later, I joined HomeAway, a vacation rental marketplace, where I stayed for 11 years until the company was acquired by Expedia.

    Later on, Ross and I met up for coffee, and he started talking about this idea of building something to help entrepreneurs and people who are starting small businesses. I was intrigued and excited. I’d always been passionate about that category in the market: Small businesses are what keep the economy growing and going.

    Related: I Walked Away From a Corporate Career to Start My Own Small Business — Here’s Why You Should Do the Same

    So Ross and I founded ZenBusiness in 2017.

    When it comes to a fast-growing company like ours, we have so many things on our to-do list, but we don’t always have the resources to get them done at the same time, so we have to prioritize.

    AI has been one of those priorities. Everybody in business should be using it these days. It’s a great tool that saves time once you get employees on board and using it based on their role and function. Our personalized AI assistant, ZenBusiness Velo, is included with every LLC formation and helps entrepreneurs start and grow their businesses.

    Related: Two-Thirds of Small Businesses Are Already Using AI — Here’s How to Get Even More Out of It

    “It all comes down to this — people are at the center of any great company.”

    For a long time, I’ve had this mantra that’s helped me succeed as a business leader: Be fearless, be ethical, be passionate.

    Being fearless means recognizing that nothing is ever going to be perfect, but you just do it anyway. Being ethical means always being honest, to yourself, to your co-workers, to anyone. And being passionate is everything. Loving your work and doing the best job possible will help you progress in your career and build your business.

    It all comes down to this — people are at the center of any great company. Anything you do is all about people, whether they’re employees, customers or the community.

    ZenBusiness puts this rule into action by hearing and supporting its employees.

    For example, we became an early adopter of remote work. The company sent employees home when the pandemic hit, but as we continued to grow and hire more people, we listened to employees who said that they preferred working from home. Remote work gave them the chance to spend time with their families, cut down on commute hours and be more productive.

    Related: A CEO Who Runs a Fully Remote Company Has an Unusual Take on Employees Starting Side Hustles: ‘We Have to Be Honest With Ourselves’

    “Maybe you launch as a side hustle to test it out.”

    All aspiring entrepreneurs should avoid the pitfall of thinking about a business idea for too long before they take action: Do it sooner rather than later.

    You don’t have to drop everything else you’re working on to start. Maybe you launch as a side hustle to test it out. Talk to the people you’re trying to solve a pain point for because those conversations will give you a lot of information.

    Every day, you’re learning something new, and being able to pivot fast can be the difference between driving your business in the right direction or not. There are always going to be surprises along the way. So remember, it’s all about the people who are around you — it’s all about the people you bring in to help you go through your business journey.

    This article is part of our ongoing Women Entrepreneur® series highlighting the stories, challenges and triumphs of running a business as a woman.

    This as-told-to story is based on a conversation with Shanaz Hemmati, COO and co-founder of ZenBusiness, a $1.5 billion company that provides an all-in-one platform helping small businesses become official, stay compliant, manage finances and more. Her co-founder is Ross Buhrdorf, who serves as CEO. The piece has been edited for length and clarity.

    Image Credit: Courtesy of ZenBusiness. Co-founder and COO Shanaz Hemmati.

    The rest of this article is locked.

    Join Entrepreneur+ today for access.

    Amanda Breen

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  • These Are the 3 Most Common Mistakes I See First-Time Founders Make as an Investor | Entrepreneur

    Opinions expressed by Entrepreneur contributors are their own.

    Over the years, I’ve worked with and invested in many early-stage companies.

    I’ve seen promising startups gain traction and scale beyond expectations. Sadly, I know too many founders fall into the same predictable traps. They make simple mistakes that stall growth or even derail their businesses entirely.

    It’s not incompetence or a lack of determination. Passion, drive and ambition are vital qualities for entrepreneurs. However, they can lead founders down a dangerous path if they go unchecked.

    If you’re building a business right now, especially your first one, I want to highlight three of the most common mistakes I see founders make and offer some tips on how to avoid them.

    Related: 7 Fatal Mistakes Founders Make Just When Business Is Getting Good

    1. You assume you have product-market fit (when you don’t)

    One of the earliest and most dangerous mistakes founders make is acting as though they’ve achieved product-market fit before they have.

    They believe their idea is solid and move full steam ahead, spending money on development, marketing and hiring without validating their product with real customers.

    Why does this happen? Simple: It’s easy to fall in love with your own idea. You think you’re building something the world needs, and it feels obvious to you. But that’s a dangerous place to operate from.

    You don’t have product-market fit until your product is in someone else’s hands who isn’t your friend, spouse or former coworker. You have a hypothesis.

    Case study: Pivoting based on real users

    I remember a founder in our network who started a cosmetics company. When he launched the company, he thought the core audience would be women in their mid-20s, so they targeted, built for and marketed to that group. But when the sales data started coming in, it told a different story.

    It turned out that middle-aged and older women were the most loyal customers. They bought the product, loved it and were practically evangelists for it. To the founder’s credit, he listened to the market and pivoted, taking them from a generic play to a very focused, profitable one.

    Build, test, then expand

    In enterprise software, the same principle applies. Founders often build feature-packed platforms in isolation, only to learn that their users care only about a handful of the hundreds of features. The rest are simply wasted time, effort and capital.

    The lesson: Get a working version of your product into the hands of real users as soon as you can. Pilot programs. Beta testers. Whatever it takes. Listen to what users value and build around real-life data, not your assumptions.

    Related: The Top 2 Mistakes Founders Make That Hinder the Growth of Their Companies

    2. Believing you can do everything yourself

    Most founders are the Type-A, alpha dogs who believe they should be able to do it all.

    I understand that instinct. In the earliest days, you kind of have to. You’re bootstrapped, scrappy, taking on every role in the company. But what starts as a necessity can quickly become a bottleneck.

    The issue isn’t just capacity; it’s control. Founders who resist delegation often believe they’re the best person for every task. They think they know better than the marketing lead they hired. They’re the ones who can close the deal faster than the sales team. They can tweak the product more effectively than the engineers.

    It becomes a mindset that stifles growth.

    You accomplish more when you do less

    I’ve seen it many times: A founder builds a product, launches it, starts gaining traction and then it stalls out.

    It’s not a market shift, but because they’re still trying to be the player, the coach and the general manager all at once. Eventually, every founder has to evolve.

    Think of it in sports terms. You start as the player on the field. Then, you become the coach, setting the strategy. Over time, you become the GM, building a team that can execute and win without you in every play.

    The hard truth about delegation

    Letting go is hard. It’s your company. It’s your name on the paperwork. But if you want to grow, you must accept the fact that you will have to trust your team. Your job is to empower people to perform, not micromanage them into mediocrity.

    And yes, delegation comes with a cost. There’s a learning curve. Productivity dips before it rises. But the upside of having people who can think, lead, and execute independently is massive. The sooner you realize this principle, the faster you’ll find success.

    3. Spending capital just because you have it

    Finally, one of the mistakes I see all the time is founders who spend money just for the sake of spending.

    Imagine you just raised a healthy investment round of $10 million. Suddenly, you feel pressure to act. You hire more people, launch new initiatives, and sign big contracts. Soon it’s all gone. Why?

    It’s easy to confuse movement with progress.

    I’m not opposed to rapid spending. If a founder tells me they spent $5 million in six months and can show precisely how that spend drove measurable results, I’m thrilled. I’ll give them another $5 million and let them keep rolling. But I don’t want to see a company hire an entire marketing department before defining its go-to-market strategy, invest in a new product line without validating the demand or sign big vendor contracts to “look like a real company.”

    Spend strategically, not reactively

    You don’t need a T-shirt team just because you think that’s what startups do. Every dollar should align with your core strategy. If it doesn’t, it’s wasted.

    From an investor’s perspective, I don’t want you sitting on cash forever. But I also don’t want you burning it for headlines. Strategic spending beats reactive spending every time.

    Related: 8 Mistakes First-Time Founders Make When Starting a Business

    How to avoid these mistakes

    If you’re a founder navigating the early stages, here are a few quick tips on how to steer clear of these traps:

    • Validate, then scale: Get your product into users’ hands early. Listen and adjust. Don’t build in a vacuum.
    • Delegate with purpose: Start handing off responsibilities as soon as you can. Expect the dip. Embrace the long-term upside.
    • Spend with discipline: Know your strategy, tie every investment to it, and resist the pressure to “look busy.”

    At Dale Ventures, we look for founders who are self-aware enough to grow into the next version of themselves and disciplined enough to avoid these costly mistakes.

    The first-time founder who understands this isn’t just building a startup. They’re building a foundation for lasting success.

    Hilt Tatum IV

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  • Mom’s Creative Side Hustle Grew to $570,000 a Month: Penny Linn | Entrepreneur

    This Side Hustle Spotlight Q&A features Krista LeRay, the 34-year-old founder of needlepoint store Penny Linn. She lives with her husband and two children in Westport, Connecticut. Responses have been edited for length and clarity.

    Image Credit: Courtesy of Penny Linn. Krista LeRay.

    Want to read more stories like this? Subscribe to Money Makers, our free newsletter packed with creative side hustle ideas and successful strategies. Sign up here.

    What was your day job or primary occupation when you started your side hustle?
    Before starting Penny Linn, a new-age needlepoint store offering hand-painted canvases, accessories and more, I was a full-time influencer running my blog, Covering The Bases. I started the blog in 2013, but I only took it full-time about a year before starting Penny Linn. While managing the blog, I had a corporate career at Major League Baseball, where I worked on the social media team for over five years.

    Related: He Spent $36 to Start a Side Hustle. Now the Business Earns 6 Figures a Year — With Just 1-2 Hours of Work a Day: ‘Freedom.’

    When did you start your side hustle, and where did you find the inspiration for it?
    I initially learned to stitch from my grandma, who inspired the name of the business, and then I really got into it in college at the University of Kentucky. I picked it back up again in 2018 when I started stitching custom belts for my dad and husband, and a ring bearer pillow for my wedding in 2019. Little did I know that this would be the perfect hobby to fall back in love with as the pandemic approached.

    As I got back into stitching, I quickly stitched through my stash of canvases and was disappointed with both the in-person and online needlepoint shopping experiences. It felt antiquated; there weren’t many sites with a good user experience, a handful of the shops made you call to order, and the designs felt very mature. I found myself wishing there were more fun and better accessories and canvases, so I started making them after my search came up short.

    Image Credit: Courtesy of Penny Linn

    What were some of the first steps you took to get your side hustle off the ground? How much money/investment did it take to launch?
    When I started painting my own canvases, I wasn’t even in the mindset of starting a business; it was still just a hobby for me. I probably spent under $100 buying a blank canvas on Etsy and paint at Michaels, and painted the infamous Ralph’s Coffee cup for myself. When I shared it on my Instagram, I had an overwhelming number of followers ask to buy one, so I knew my followers were also interested in needlepoint.

    As I began searching for cuter accessories for myself, I found that many custom items had a 100-item minimum. At the time, I had a business bank account for my blog, so I used that money to order the inventory and knew that I could at least sell 90 of them to my followers who also needlepointed. After making a few canvases and seeing the demand, I realized I had enough ideas to launch a larger collection online. So I bought the smallest Shopify package, started sourcing needleminders and project bags, and recruited my friends and family to help paint canvases.

    All in all, I spent about $5,000 on the initial inventory for our accessories and an additional $2,000 on shipping materials, canvas tape, etc., but none of this accounted for my time painting the canvases one by one, which was the biggest investment.

    Related: These 31-Year-Old Best Friends Started a Side Hustle to Solve a Workout Struggle — And It’s On Track to Hit $10 Million Annual Revenue This Year

    If you could go back in your business journey and change one process or approach, what would it be, and how do you wish you’d done it differently?
    Looking back on how I built my business, it’s a catch-22; if I had known what I know today, I might have done it differently. However, having my hands in every aspect of the business has brought me a great deal of knowledge and appreciation that continues to shape the business.

    In the beginning, I hand-painted nearly every canvas, which took many, many hours, but it kept costs low since my labor was essentially free and gave me control over my inventory. If I had known that people outsourced painting, it would have saved me so much time and energy, but doing it myself taught me the value of a hand-painted canvas.

    Similarly, I wish I had hired people at the beginning to take more off my plate, but by doing it all, I learned valuable lessons and knew how I wanted every aspect of the business to run. I don’t think Penny Linn would be such a thoughtful and impactful brand today if I hadn’t had my fingers on every aspect of the business in the beginning.

    Related: I Interviewed 5 Entrepreneurs Generating Up to $20 Million in Revenue a Year — And They All Have the Same Regret About Starting Their Business

    When it comes to this specific business, what is something you’ve found particularly challenging and/or surprising that people who get into this type of work should be prepared for, but likely aren’t?
    The reason Penny Linn has been so successful as a business, and also in reviving the cultural love for needlepoint, is that we brought much-needed innovation to the industry. I never expected the amount of pushback from vendors and industry vets I received. Across the board, people pushed back on our ideas and how we ran our business.

    Today, we have found partners who believe in our growth and are building with us. When we launched our acrylic line in 2022, there was so much chatter online that it wasn’t innovative or unique, but today we hold a patent for the design, and it’s one of our bestselling lines. We also take a slightly smaller wholesale margin than the industry standard because I believe in making needlepoint accessible. Our wholesale partners were initially adamant that it wouldn’t be successful, but it has proven otherwise. I developed a thick skin while blogging and learned to shut out the noise, which has followed me into Penny Linn as we continue to shake up the industry.

    Image Credit: Courtesy of Penny Linn

    Can you recall a specific instance when something went very wrong? How did you fix it?
    I vividly remember one of our first bag launches, which did not go as planned. It was a beautiful project bag with leather and PVC that we sold through so quickly! As I was packing them, I tested a few of the zippers and was very disappointed to find that they stuck and were difficult to open, despite the samples working perfectly. I reached out to each customer who had ordered them and let them know that the bags weren’t up to our standards. I offered them a full refund if they wanted to return the bag or a discount if they wanted to keep it.

    This became one of my biggest rules in business: When anything goes wrong, I need to take ownership and work to rectify it immediately. Our community was beyond appreciative of how proactive we were, and most ended up keeping the bags. We put the rest of the bags on clearance and now work with our team and vendors to ensure we have quality control measures in place.

    How long did it take you to see consistent monthly revenue? How much did the side hustle earn?
    In the first six months after we launched, the only consistent revenue was what we generated during launches. Everything would sell out so quickly that we wouldn’t have any inventory left until the next launch. We would often have a day or two without sales in between launches, which wasn’t a sustainable way to run a business. To prevent this, we started producing more inventory and introduced our Penny Linn Collective, allowing us to bring on designers who expanded our offerings. Our designer collective has been fruitful for us over the past five years, and we continue to grow it today.

    We started seeing more consistent revenue in year two, doing just over $30,000 per month. The popularity of our launches started to level out, and we could better forecast inventory to keep our income steady. It was such a big deal for us at the time to reach these numbers, but we do that in a day now. Each year has been drastically different in terms of demand, and about every six months, we reach an inflection point where we need to increase quantities even more.

    Related: This Couple’s ‘Scrappy’ Side Hustle Sold Out in 1 Weekend — It Hit $1 Million in 3 Years and Now Makes Millions Annually: ‘Lean But Powerful’

    What does growth and revenue look like now?
    It’s been really exciting that Penny Linn has doubled or tripled each year. In 2024, we did $4.4 million in revenue, and we have already surpassed that and are on track to double it in 2025. We are currently averaging $570,000 per month. Whatever I think our ceiling might be, we come in and double it each year. Our growth has been so explosive that I do expect it to start leveling out in the next year or so, but there is still so much opportunity for the business.

    My mind is always racing with new ideas for the brand as we expand our product offering, launch new designers under the Penny Linn Collective and bring new accessories to market. Our store opening in Norwalk, Connecticut, earlier this year was a huge milestone for us, and now we are exploring what more stores might look like. I don’t see our growth slowing down anytime soon.

    Image Credit: Courtesy of Penny Linn

    What do you enjoy most about running this business?
    I honestly love what I do so much and find great fulfillment in it. I feel so much pride, excitement and joy thinking about what we’ve created at Penny Linn and the business I’ve built in under five years. It’s nothing I could have ever imagined as my career or what I expected Penny Linn to grow into. We haven’t seen many bumps in the road yet, and keep having success after success, which energizes me to keep going.

    I pride myself on the fact that Penny Linn is “by a stitcher for a stitcher,” and there is nothing more satisfying as a needlepointer to want something in my collection and to be able to make it. I’m privileged to have the ability to work with our vendors to create the products of my dreams, and it’s just as exciting to see how much our community loves them.

    I also find so much joy in the change we have brought to the industry and how we have been able to bring needlepoint to the forefront for a new generation. It’s crazy to sit back and think that my brand has revived a centuries-old tradition and built it into something that will continue to live on and evolve for generations to come.

    Related: These Friends Started a Side Hustle in Their Kitchens. Sales Spiked to $130,000 in 3 Days — Then 7 Figures: ‘Revenue Has Grown Consistently.’

    What’s your best business advice?
    The first is, “If you don’t ask, the answer is always no.” People are often scared to reach out because they are afraid of rejection, but my motto is always to ask, and if they don’t reply, it’s still not a no. If they don’t respond, it’s not the end of the world, but the opportunity for the answer to be yes is so much greater.

    My second is to learn the difference between constructive feedback and criticism. If someone doesn’t like you or your business, they will never have anything nice to say, and it’s not worth listening to. However, if they are a loyal fan and a frequent shopper, and they comment on how a product or process might be improved, it’s worth listening to. It’s easy to get lost in the negative feedback, but the faster you learn what is worth listening to, the better decisions you will make for your business.

    Amanda Breen

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  • Can Startup Founders Become Great CEOs? | Entrepreneur

    Opinions expressed by Entrepreneur contributors are their own.

    As your business evolves from startup to growth stage, so must your role. You may decide to stay small, especially if you like to do everything yourself, and that’s okay. But if you dream of scaling up, you will need an effective CEO. Until you have enough money to bring in someone who can step into that role, that someone needs to be you.

    I learned this the hard way. I once recruited a buttoned-up senior executive from an advisory services firm to help us scale. In the first month, this soon-to-be former employee repeatedly told my team that “everyone knows founders are terrible CEOs” — especially when a decision was made they didn’t agree with. They cited research that said mid-to-large-sized companies led by the people who founded them were less productive.

    Even if that may be true for some corporations, founders CAN evolve into outstanding CEOs — rather than being replaced by them. It’s not easy, but it’s achievable.

    What I’ve learned through my pursuit to become a better CEO is that personal change does not happen overnight. It’s not linear. And it usually does not happen alone. Don’t expect perfection at first; treat it as a growth process. Just be better today than you were yesterday.

    If you want (or need) to make the transition from acting like a founder to being seen as a CEO, here are just a few of the things you need to do.

    Related: I Shifted From Founder to CEO 20 Years Ago and Never Looked Back — Here’s How to Successfully Make the Leap

    Keep being visionary

    For most entrepreneurs, your business starts with a strong sense of purpose. Maybe you left the corporate world to be your own boss, or maybe you’re a creative thinker who never fit the traditional mold.

    Regardless of your personal reasons, start thinking about your company in terms of what you want it to accomplish and why. Define how you plan to improve people’s lives or make a difference without sacrificing your values. Whether you’re the founder, the CEO or both, being able to articulate your vision again and again is critical and something you’re probably already good at.

    Keep being the best salesperson in the company

    As the founder, no one can sell your passion, purpose or product like you.

    Interacting with customers will teach you what the buyers in the market need, and more importantly, what they want to buy. Making those first few sales will help you crystallize your vision and give you confidence that you’re on the right track.

    The more your company grows, however, the more you’ll need to sell your vision to inspire your team and attract new investors. You’ll have to tell your story to recruit key employees and generate favorable coverage in the media. Leave much of the customer-facing work to qualified salespeople.

    Focus on process

    Business works best when the focus is on people > product > process. As a founder, you focus more on the product and the people you need to get your startup off the ground. As a CEO, you must pay even more attention to the people part.

    But you also have to become more serious about process — formal, documented and repeatable processes. The documentation part of this is very important. Should something happen to you and all the knowledge to run the company is in your head — inaccessible to the people who need to take over your work — you’ll have a big problem.

    Related: What Does It Mean to Be a Successful CEO Today? Here’s 5 Traits To Look Out For

    Be more strategic

    Founders create solutions to today’s problems. CEOs anticipate tomorrow’s obstacles. My friend, Jeffrey Hayzlett, likes to say CEOs “don’t need to be the smartest person in the room, they need to be the most strategic.”

    You can’t focus enough on strategy if you’re spending all your time putting out the fires that erupt in day-to-day operations. You must allow yourself time to think about where your company needs to go, how it will get there and how you’ll thwart the people trying to stop you.

    Start by asking the right questions instead of worrying about having the right answers.

    Be more willing to delegate

    Often, visionaries don’t want to compromise, and they won’t delegate. The temperamental Steve Jobs served as evidence of this type of visionary.

    When I was in Dallas recently for the launch of a book I co-authored, “The Leader’s Playbook: CEOs Transforming Vision into Action,” I met the founder of a successful startup. He was frustrated that his company had “plateaued.” After a few questions, I learned his problem was attributable to one of the biggest factors that stunts the growth of small businesses. It’s the founder’s inability (or unwillingness) to delegate everyday tasks so they can focus on more important things.

    This requires having a high level of trust in his employees and contractors, which he didn’t have.

    Hire people better than you

    Early in my career, I was inspired by advertising agency icon David Ogilvy, who believed, “Always hire someone who is better than you” at something you’ve always done yourself. This principle not only makes your company stronger; it makes delegation much easier.

    Your first few hires need to be good ones, so your recruiting process (there’s that word again) needs to be rigorous. If you hire friends and family members, cutting your losses from a bad hire becomes substantially trickier to navigate.

    Mind the metrics

    If you’re like most founders, you’re a visionary — acting more like a building developer than a building manager. Accounting is not nearly as much fun. But a CEO also needs to focus on numerical details, demanding accountability at scale, growing efficiencies and using reliable business metrics as the scorecard for generating profit.

    Be more introspective

    Being a CEO not only requires a different skill set than a founder; it also demands a different mindset. Start with an honest look in the mirror.

    The difference between being a catalyst for positive change and being the choke point starts with how you think about things. What are the thoughts keeping you from being the CEO that “your baby” needs to leave the nest and grow its own wings?

    Taking the first step

    As an entrepreneur, deciding how to balance the roles of visionary and CEO can be overwhelming. I was fortunate to find an executive coach who helped me become the CEO my company needed.

    Whether you tap into coaches, mentors or peer advisory groups, build a circle of trusted and successful people to advise you. My personal journey resonated so strongly with me that I now offer leadership coaching to turn founders into high-impact CEOs.

    Related: 5 Things I Wish Someone Had Told Me Before I Became a CEO

    Trust your instincts

    Any professional growth path will have its share of setbacks. Not every plan will be perfectly executed. You won’t always do or say the right thing “in the moment.” And you may slip back into your old thinking from time to time.

    But with enough commitment and discipline, you CAN grow into a CEO who will transform your company into what you’ve always dreamed it could be.

    As your business evolves from startup to growth stage, so must your role. You may decide to stay small, especially if you like to do everything yourself, and that’s okay. But if you dream of scaling up, you will need an effective CEO. Until you have enough money to bring in someone who can step into that role, that someone needs to be you.

    I learned this the hard way. I once recruited a buttoned-up senior executive from an advisory services firm to help us scale. In the first month, this soon-to-be former employee repeatedly told my team that “everyone knows founders are terrible CEOs” — especially when a decision was made they didn’t agree with. They cited research that said mid-to-large-sized companies led by the people who founded them were less productive.

    Even if that may be true for some corporations, founders CAN evolve into outstanding CEOs — rather than being replaced by them. It’s not easy, but it’s achievable.

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    C. Lee Smith

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  • My Business Hit $1 Million — Then a $46,000 Mistake Exposed the Biggest Bottleneck to Explosive Growth | Entrepreneur

    Opinions expressed by Entrepreneur contributors are their own.

    I’ll never forget the day I realized I couldn’t do it all anymore.

    My business had just crossed the million-dollar mark, but I was still trying to handle everything myself — coaching clients, selling, leading my team and running the accounting. Then, one day, I discovered I’d accidentally overcharged our biggest client $46,000 over nine months because I’d set up auto-pay and never double-checked it.

    The wave of panic that hit me was overwhelming. It was one of the worst moments of my professional life. I immediately owned the mistake, apologized and worked out a plan to credit the money back over six months. Thankfully, the client was incredibly gracious. But in that moment, I knew something had to change — I had to stop trying to do everything and start leading like a CEO.

    Related: 10 Growth Strategies Every Business Owner Should Know

    Stop doing — start leading

    When you launch a business, you wear every hat. You create the product, send invoices, post on social media and answer every email. That scrappy hustle is necessary to get off the ground — but it won’t get you to the next level.

    Scaling means an identity shift. You have to stop being the “doer” and become the delegater. Instead of asking, “How can I do this?” start asking, “Who can do this better than I can?”

    This is easier said than done. But holding onto control keeps you stuck. You’ll stay buried in day-to-day tasks instead of focusing on big-picture moves that grow your business.

    For me, stepping into the CEO role meant redefining leadership on my own terms. I didn’t want to follow a corporate playbook written by men. I wanted to lead in a way that aligned with my values and strengths — building flexibility into my schedule, doubling down on coaching and sales (my superpowers) and empowering my team to own the rest.

    Build the right team — and trust them

    Hiring an assistant to manage my schedule, emails and admin was one of the smartest moves I made. It freed up hours I could now spend coaching clients and bringing in new business.

    Delegating is scary. You worry they won’t do it as well as you can. Sometimes, that’s true. But growth only happens when you give others space to learn. If they stumble, you help them recover — and they get stronger. That’s leadership.

    Ask yourself: What are your superpowers? Are you a sales rockstar? A client relationship builder? Then be honest: How much of your time is lost in tasks that drain you — digging out of your inbox, chasing invoices?

    If those tasks pull you away from your strengths, it’s time to delegate. When you operate in your zone of genius and let others handle the rest, your business will finally grow the way it’s meant to.

    As your team grows, get to know them as people. We have every team member take the Enneagram test to understand communication styles and personalities. It’s taught me the power of listening and meeting people where they are.

    Create systems that set you free

    If your business lives only in your head, you can’t scale. Every process — client onboarding, social media posting, monthly reporting — needs to be documented so someone else can follow it.

    At our company, we use Asana for task management and Slack for communication. Everyone knows the flow, and it keeps us aligned.

    When I sell a client, I immediately hand them off to our onboarding team. Why? Because I know I’m the worst at follow-up. I know my strengths—and where I tend to get in my own way.

    We use Stripe for payments and Go High Level for email automations. These simple systems keep us running like a well-oiled machine.

    Related: Most Entrepreneurs Fail Because They Ignore These 3 Business Stages

    Think like a CEO

    If your calendar is full of urgent tasks, there’s no time for strategic thinking. But that’s exactly where CEOs live.

    Everyone on my team works from home on Fridays. I use that day to strategize and focus on the future. Where are we headed? Who do we need to become to get there? I take walks, listen to industry podcasts, and brainstorm new ideas.

    I also use this time to vet opportunities. It’s tempting to say yes to everything, especially early on. But now, before I commit, I ask: Is this worth my time? Does it align with our vision? Will it deliver a real return on investment?

    You belong in the CEO seat

    For too long, I thought being a great business owner meant doing everything myself. But real growth started when I stepped into the CEO seat — hiring for my weaknesses, trusting my team and making decisions from a long-term perspective.

    You don’t have to run your business like anyone else. Define what leadership means for you. Build a business that supports your strengths—and let go of what’s holding you back.

    You didn’t start your business to stay small. So take your CEO seat… you’ve earned it.

    I’ll never forget the day I realized I couldn’t do it all anymore.

    My business had just crossed the million-dollar mark, but I was still trying to handle everything myself — coaching clients, selling, leading my team and running the accounting. Then, one day, I discovered I’d accidentally overcharged our biggest client $46,000 over nine months because I’d set up auto-pay and never double-checked it.

    The wave of panic that hit me was overwhelming. It was one of the worst moments of my professional life. I immediately owned the mistake, apologized and worked out a plan to credit the money back over six months. Thankfully, the client was incredibly gracious. But in that moment, I knew something had to change — I had to stop trying to do everything and start leading like a CEO.

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    Deedra Determan

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  • Starting a Business? You Need Founder Friends — Here’s Why | Entrepreneur

    Opinions expressed by Entrepreneur contributors are their own.

    Starting a business can be a lonely endeavor. No matter how confident you are in your product and in yourself, there will always be times when doubt creeps in — usually just as you’re trying to fall asleep.

    These crises of confidence can be fatal to your vision, but they don’t have to be. And one way to stave off the startup scaries is by having other founders in your life to lean on.

    Back when Jotform was a company of one (me), I had a close friend who was also a fellow early-stage founder. His idea — selling beauty products online — was conceptually completely different from mine, but that didn’t matter. We were facing the same struggles, the same uncertainties and many of the same difficult decisions.

    Each week, we’d spend hours walking through New York, hashing out our ideas as we traversed the cobbled streets of SoHo to the tree-lined walking paths of Brooklyn Heights. We’d exchange marketing and SEO ideas, workshopping products and sales strategies. We celebrated each other’s small wins — like landing a new customer or finally fixing a stubborn bug — and vented about the setbacks. Those conversations didn’t just make me feel less alone; they sharpened my thinking and kept me accountable. In a phase of life where so much felt uncertain, that kind of camaraderie was invaluable.

    For founders, especially solo founders, having someone who understands the unique pressure of building something from scratch can make all the difference. Here’s why.

    Related: You Can’t Succeed Alone — Why Small Businesses Must Work Together

    The power of peers vs. mentors

    I believe strongly in the power of mentors, and think everyone should have one. Mentors have been in your shoes and can offer sage advice that comes from experience and hindsight. But while mentors are indispensable, peers bring something different — and equally essential — to the table.

    A mentor can tell you how they handled a particular situation five or 10 years ago. A peer, on the other hand, can tell you what they did last week — and whether it worked. The advice is current, and the exchange goes both ways. You’re not just receiving guidance, you’re collaborating.

    Peers also provide something mentors can’t always offer: emotional resonance. They’re in the trenches with you, facing the same economic climate, technological changes and customer expectations. There’s no need to explain why a poorly executed launch or bad hire feels devastating. They already know. That shared understanding builds trust fast, and trust leads to lasting bonds.

    In those early walks with my founder friend, we weren’t pretending to have it all figured out. We were troubleshooting in real time, riffing on ideas, asking questions and giving each other the push we needed to keep going. It didn’t matter that our products were different — what mattered was that our challenges were the same. I also found that working through his business issues gave my brain a needed break from focusing on my own. Oftentimes, I’d return to my desk afterwards with fresh insights I would never have had if I’d kept spiraling on my own bumps in the road.

    Related: I Mentor First-Time Entrepreneurs — These Are the 4 Unseen Benefits I Gained By Giving Back

    Where to find founder friends

    These days, most of my close friends are also fellow founders. Running a business is pretty consuming, but we don’t just talk strategy — our conversation drifts equally around the people we hire, our company cultures and how to be motivational leaders. I’ve learned so much during our hangouts over coffee or beer that no book or YouTube video could ever have taught me.

    If you’re launching a business but don’t yet have a built-in founder community, don’t despair. These days, there are tons of resources for connecting with like-minded people. Subreddits like r/Entrepreneur and communities like Indie Hackers are great starting points, but don’t just stop at making online connections. Check your city for tech meetups — with startups more geographically dispersed than ever, you don’t need to live in New York or the Bay Area to find one near you. And as with most things, your existing network is one of your most powerful resources. Make it known you’re looking to build up your community of fellow founders. In all likelihood, you know someone who knows someone doing the same.

    If you’re an introvert like me, you may find all this intimidating. But the truth is, so much of running a business is relationship-building. And remember, these early meetups don’t have to be formal. A 20-minute coffee chat can lead to years of camaraderie.

    Once you’ve made a connection, carve out space for it. My friend and I had our weekly walks in New York. You might have a 30-minute Zoom every other Friday, or a WhatsApp thread where you trade updates and cheer each other on. Consistency is key. These conversations are most powerful when they become habitual, rather than a one-off.

    And finally — be honest. This isn’t an interview. You don’t need to posture or pretend. Talk about the idea that fizzled. Be real about your scaling woes. Vulnerability is what makes relationships meaningful. It’s also what makes them useful. Because the goal isn’t to impress, it’s to grow.

    Building a business will always come with moments of doubt. But having people around you who truly understand what you’re going through can make the path feel a lot less lonely.

    Starting a business can be a lonely endeavor. No matter how confident you are in your product and in yourself, there will always be times when doubt creeps in — usually just as you’re trying to fall asleep.

    These crises of confidence can be fatal to your vision, but they don’t have to be. And one way to stave off the startup scaries is by having other founders in your life to lean on.

    Back when Jotform was a company of one (me), I had a close friend who was also a fellow early-stage founder. His idea — selling beauty products online — was conceptually completely different from mine, but that didn’t matter. We were facing the same struggles, the same uncertainties and many of the same difficult decisions.

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    Aytekin Tank

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  • Most Founders Start With the Product. I Started With These 3 Questions Instead. | Entrepreneur

    Opinions expressed by Entrepreneur contributors are their own.

    Too many founders start with the product. They get excited, build something, and then scramble to figure out if anyone actually wants it.

    I almost did the same. Technically, I started by generating silly AI images of my boss to make my coworkers laugh. But when I saw the potential of the tools I was playing with — and how accessible they were becoming — I realized I could turn it into something real.

    I didn’t have a background in AI or deep learning. But with open-source tools like Stable Diffusion suddenly available, people like me could build things that felt like magic.

    And like most entrepreneurs, I wanted to move fast. But instead of rushing to build, I gave myself a reality check. I asked three hard questions before writing a line of code. That checklist became the foundation of my business — and helped me avoid wasting months (and money) on a product no one wanted.

    These same questions apply whether you’re launching a SaaS company, a consumer product, a service-based business, or, yes, an AI tool.

    Related: AI Isn’t Plug-and-Play — You Need a Strategy. Here’s Your Guide to Building One.

    1. Is there real demand?

    Before investing anything in product development, I set up a test. I opened an Etsy store selling AI-generated pet portraits during the holidays. It was clunky. Every order meant I was manually training models and fulfilling them by hand.

    But people paid. They loved the results. It wasn’t scalable — yet — but that didn’t matter. It gave me proof:

    • I could deliver something people genuinely valued
    • They were willing to pay for it

    This kind of early signal is more important than a sleek prototype or a detailed roadmap. For you, it might mean selling a simplified version of your offer, pre-selling a service, or running a paid pilot. The goal is the same: confirm there’s real demand before you build at scale.

    2. Will people pay me — and how?

    After validating interest, I started experimenting with pricing. We tested $15, then $25. We ran ads on Reddit. Some worked, most didn’t. I tried subscriptions — but quickly realized that running custom-trained models on demand was too expensive to support recurring plans at an early stage.

    So I switched to a one-time payment model. Simple, low-friction, no complicated onboarding. We started at $9.99, and conversions were strong. Over time, we added higher-tier pricing — but from day one, the business had to make financial sense.

    Many people advised offering a freemium version. I considered it, but GPU costs made that unrealistic. Instead, I built a free tool that looked like our main offering (an AI headshot generator) but was actually a low-cost background remover. It gave users a taste of the experience and warmed them up to buy. And it converted.

    The takeaway? Revenue models aren’t just about pricing — they’re about sustainability. Founders often over-index on what’s ideal for the user and forget what’s viable for the business.

    3. Can I actually reach people?

    I didn’t have an audience. I didn’t have connections or media buzz. But I had Reddit.

    I started joining threads where people were talking about AI headshots. I added value, offered comparisons, answered questions — and eventually, shared my own product. That got us our first 100 customers. We used Google Ads to scale to 1,000.

    It wasn’t viral. It wasn’t pretty. But it worked. Why? Because I focused on solving the hardest part of distribution first: attention and trust.

    When people think about go-to-market, they think channels. But it’s better to think in terms of risk:

    • Can you find the right people?
    • Can you earn their attention?
    • Can you convert them — without overspending?

    If the answer is no, it doesn’t matter how good the product is.

    Related: AI Will Define Your Brand If You Don’t — Here’s How to Take Control

    Don’t build until you can answer these three questions

    Every founder wants to build something great. But building too early — or on shaky assumptions — can kill even the best ideas.

    A rough product built on real answers will always beat a polished one built on hope.

    So before you start building or investing heavily in a new product or service, ask yourself:

    • Who wants this right now?
    • Will they pay?
    • Can I reach them profitably?

    Everything else can wait.

    Too many founders start with the product. They get excited, build something, and then scramble to figure out if anyone actually wants it.

    I almost did the same. Technically, I started by generating silly AI images of my boss to make my coworkers laugh. But when I saw the potential of the tools I was playing with — and how accessible they were becoming — I realized I could turn it into something real.

    I didn’t have a background in AI or deep learning. But with open-source tools like Stable Diffusion suddenly available, people like me could build things that felt like magic.

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    Jeremy Gustine

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  • Her Business Helps Women Earn in a $6.3B Industry: ‘Rewarding’ | Entrepreneur

    Moniqueca Sims, owner of SSG Appliance Academy, got her first glimpse into the appliance repair industry while dating a man who worked in the space. “He worked all the time, seven days a week,” Sims recalls, “so I used to go out with him just to spend time with him. I saw how easy it was for him to repair those appliances, and he was repairing them quickly.”

    Image Credit: Courtesy of SSG Appliance Academy. Moniqueca Sims.

    Sims believes in “working smarter, not harder” and had the idea to hire technicians to help the man she was dating with repair calls. She did, but when he didn’t slow down, she ended up with her own appliance repair company.

    However, in running that business, Sims lost a significant amount of money purchasing parts. Many people she hired didn’t actually know how to repair appliances — and would just switch out part after part in search of a fit.

    Related: After Experiencing the ‘Lack of Diversity’ in Tech, This Software Engineer Started a Business That’s Changing Lives: ‘People Are Waking Up’

    So Sims took matters into her own hands again. She enrolled in an online course to learn about appliance repair and started handling jobs herself, even taking her kids along sometimes.

    “When you fix something, it boosts you up, every time you do it.”

    Still, Sims knew there had to be a better way to train and hire technicians for business growth, so once more she set out to make it happen: She founded SSG Appliance Academy, which provides hands-on training courses on the fundamentals to have a career in the appliance repair industry, in Atlanta in 2019.

    “ I saw how appliance repair was the gift that keeps on giving,” Sims says. “When you go out, when you fix something, it boosts you up, every time you do it. It’s not a grunt job. It’s a feel-good job.”

    When Sims went out on jobs with her daughter, she found that many of the clients were stay-at-home moms who breathed a sigh of relief when they realized they wouldn’t be alone with a male worker. Knowing that, and seeing firsthand what a confidence booster appliance repair could be, Sims committed to bringing more women into the industry.

    The total appliance repair industry revenue reached an estimated $6.3 billion in 2023, yet women make up less than 3% of home appliance repairers, according to data from ConsumerAffairs.

    Related: Raised By an Immigrant Single Mom, She Experienced ‘Culture Shock’ Working at Goldman Sachs. Here’s What She Wants You to Know About ‘Black Capitalism.’

    Sims decided to partner with shelters to grow SSG Appliance Academy and offer a viable career path to the women there. Although there was a lot of interest, the shelters didn’t have the funding to back it. So Sims got approved for grants through the Workforce Innovation and Opportunity Act (WIOA).

    The funding helps low-income, under- or unemployed women and men complete SSG Appliance Academy’s program and “turn their life around,” Sims says.

    SSG Appliance Academy’s classes typically enroll eight to 10 students. The most recent course had three women in it. In the past, Sims often had to attend events and convince women to come to the class; now, word-of-mouth is helping them find it themselves, she says.

    “ You constantly have to prove yourself [as a woman] in this industry.”

    Sims looks forward to seeing even more women take advantage of SSG Appliance Academy, despite the challenges that can come with being a woman in the space.

    “ You constantly have to prove yourself [as a woman] in this industry, and not just to the customers,” Sims says. “You have to prove yourself to everybody that works in the industry.”

    Sims is also excited to see more people across the board jump into the appliance repair industry, noting that learning a trade can help people make more money than they might through earning a four-year college degree.

    “Appliance repair can really help change people’s lives,” the founder says.

    Related: This Black Founder Stayed True to His Triple ‘Win’ Strategy to Build a $1 Billion Business

    “You want to learn your craft from the inside out.”

    To other women interested in starting their own careers or businesses in the appliance repair industry, Sims has some straightforward but essential advice: Enroll in a program that can help you learn all you need to know about the trade.

    “You want to learn your craft from the inside out,” Sims says. “A lot of technicians in the field now learn on the job, so they become part-changers because they don’t learn how to diagnose and troubleshoot the appliances properly. So my advice would definitely be to take a class. It doesn’t have to be my school — any school.”

    Related: I Interviewed 5 Entrepreneurs Generating Up to $20 Million in Revenue a Year — And They All Have the Same Regret About Starting Their Business

    Sims notes that there will be plenty of obstacles along the way, but she encourages anyone interested in learning appliance repair to stay the course — because “it’s a very rewarding career and business.”

    This article is part of our ongoing Women Entrepreneur® series highlighting the stories, challenges and triumphs of running a business as a woman.

    Moniqueca Sims, owner of SSG Appliance Academy, got her first glimpse into the appliance repair industry while dating a man who worked in the space. “He worked all the time, seven days a week,” Sims recalls, “so I used to go out with him just to spend time with him. I saw how easy it was for him to repair those appliances, and he was repairing them quickly.”

    Image Credit: Courtesy of SSG Appliance Academy. Moniqueca Sims.

    The rest of this article is locked.

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    Amanda Breen

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  • Co-founders of Stakt on Starting a Side Hustle Earning $10M in 2025 | Entrepreneur

    This Side Hustle Spotlight Q&A features New York City-based friends and co-founders Millie Blumka, 31, and Taylor Borenstein, 31. The pair started a side hustle in 2021 called Stakt, an adaptable workout accessories brand.

    Blumka was a director of brand partnerships at Showfields and Borenstein was a product implementation manager at Bloomberg when they invested about $50,000 of their personal savings into the business. The co-founders have since grown it from a two-person operation to a lucrative business on track for $10 million in revenue in 2025 as it scales across Amazon, DTC and B2B.

    Read exactly how they did it, here.

    Image Credit: Courtesy of Stakt. Taylor Borenstein, left, and Millie Blumka, right.

    Responses have been edited for length and clarity.

    When did you start your side hustle, and where did you find the inspiration for it?
    Blumka and Borenstein: We had the idea for Stakt back in 2020 when home workouts became the norm and our old yoga mats just weren’t cutting it. We needed more support and versatility for the variety of workouts we were doing like sculpt and pilates, and we couldn’t find a mat that could keep up. We found inspiration through our own personal need and noticing many trainers we looked up to were rolling their mat in half to get extra support…we knew there had to be a better way.

    Related: This Couple’s ‘Scrappy’ Side Hustle Sold Out in 1 Weekend — It Hit $1 Million in 3 Years and Now Makes Millions Annually: ‘Lean But Powerful’

    What were some of the first steps you took to get your side hustle off the ground? How much money/investment did it take to launch?
    Blumka and Borenstein:     Neither of us had started a business before, let alone created a product, so the first step was a lot of networking. We spoke with friends of friends to try to understand how you even go about creating a product. We also did a lot of surveying to understand if this was an “us” problem or if other people were struggling with this, too. We each invested $25,000 of our own savings to get the business off the ground and have invested profits ever since.

    Image Credit: Courtesy of Stakt

    If you could go back in your business journey and change one process or approach, what would it be, and how do you wish you’d done it differently?
    Blumka:     If I could go back, I’d probably establish our lanes much earlier. In the beginning, we both tried to touch everything and be hands on for every aspect of the business. Once we defined who owned what, things became so much smoother. Having those roles in place earlier would have saved us a lot of time.

    Borenstein: I probably would have hired customer service support sooner, as we spent a lot of our time on customer experience when we could have spent it building the business.

    Related: These Friends Started a Side Hustle in Their Kitchens. Sales Spiked to $130,000 in 3 Days — Then 7 Figures: ‘Revenue Has Grown Consistently.’

    When it comes to this specific business, what is something you’ve found particularly challenging and/or surprising that people who get into this type of work should be prepared for, but likely aren’t?
    Borenstein:     Before starting a consumer brand, I had always thought, How hard could it be if you have a good product? It turns out the product is just the first step: Growing a business takes a ton of discipline, hard work, networking and efforts across all verticals to really make it successful.

    Image Credit: Courtesy of Stakt

    Can you recall a specific instance when something went very wrong — how did you fix it?
    Blumka:     We once had an entire container of inventory arrive damaged, and we didn’t feel comfortable selling it. Instead, we donated the mats to local organizations and used them for community events. It left us out of stock for a while, so we leaned on pre-orders and reframed the challenge as a marketing opportunity.

    How long did it take you to see consistent monthly revenue? How much did the side hustle earn?
    Blumka:     We didn’t pay ourselves until we decided it was time to make Stakt our full-time jobs instead of just a side hustle.

    Borenstein: It took about a year before things leveled out and we saw consistent monthly revenue. For the first year, there were good months, great months and bad months — eventually it became more consistent and easier to predict.

    Related: At 24, She Immigrated to the U.S. and Worked at Walmart. Then She Turned Savings Into a ‘Magic’ Side Hustle Surpassing $1 Million This Year.

    What does growth and revenue look like now?
    Blumka and Borenstein:     We are on track to do $10 million in revenue this year — doubling what we did in 2024.

    Image Credit: Courtesy of Stakt

    What do you enjoy most about running your business?
    Blumka:     The combination of creativity and community. I love taking an idea and turning it into something people genuinely connect with. That said, the real reward is seeing our products out in the wild, with people actually using and loving them. Building community around movement and wellness has been the most fulfilling part. Plus, doing it alongside my best friend is the biggest bonus.

    Borenstein: At some point, this truly stopped feeling like work. Stakt is an extension of me and my family, and every day I get to work with my best friend and my husband (whom we hired last year). I love that I can make my own schedule, my hard work is rewarded with the growth of my own business, I meet awesome people, and I get the opportunity to design new products and see them come to life.

    “Chaos is part of the journey.”

    Based on your journey so far, what’s your best advice for aspiring founders?
    Blumka:     There will never be a perfect time, perfect product or perfect plan, but you have to start somewhere. There will always be a reason to wait, but the real progress starts once you launch. This is when you can adapt, learn and grow.

    Borenstein: Everyone will have advice, but trust your gut — there’s no single playbook. And remember, no one has it all figured out; the chaos is part of the journey.

    Want to read more stories like this? Subscribe to Money Makers, our free newsletter packed with creative side hustle ideas and successful strategies. Sign up here.

    This Side Hustle Spotlight Q&A features New York City-based friends and co-founders Millie Blumka, 31, and Taylor Borenstein, 31. The pair started a side hustle in 2021 called Stakt, an adaptable workout accessories brand.

    Blumka was a director of brand partnerships at Showfields and Borenstein was a product implementation manager at Bloomberg when they invested about $50,000 of their personal savings into the business. The co-founders have since grown it from a two-person operation to a lucrative business on track for $10 million in revenue in 2025 as it scales across Amazon, DTC and B2B.

    Read exactly how they did it, here.

    The rest of this article is locked.

    Join Entrepreneur+ today for access.

    Amanda Breen

    Source link

  • How a Software Engineer’s Business Impacts Education | Entrepreneur

    As Brandon Bailey, founder and CEO of TutorD, built his career in software engineering, he came face-to-face with the “lack of diversity and inclusion” in tech — and he wanted to do something about it.

    Image Credit: Courtesy of TutorD. Brandon Bailey.

    Bailey worked at a consultancy in Chicago at the time, and as co-lead for one of the firm’s employee resource groups, he partnered with a couple of community-based organizations. One partnership was with a middle school in Bronzeville.

    The school was located about 15 minutes from Bailey’s home, but the students “had a totally different lived experience,” the founder recalls. Many of the kids had never been on an escalator or inside a skyscraper despite living just minutes from downtown.

    Related: Technology Opens the Door for Entrepreneurs to Achieve the Triple Bottom Line

    The program helped the students have those experiences and access internships and other opportunities. “That gave me this drive and passion for the educational experience and helping facilitate it,” Bailey says. “It changed my life. I know it changed [their lives].”

    But Bailey wanted to figure out how to reach even more people. He landed a job at an edtech startup in Los Angeles, California, and began to think about how he could bring together education, engineering and entrepreneurship.

    When considering the platform or tool that could accomplish that, Bailey noted one significant obstacle: There was an issue of connectivity for students who didn’t have access to computers in their homes. However, most students did have cellphones, so Bailey decided to meet the students where they were and build for those.

    Related: How DEI and Sustainability Can Grow Your Triple Bottom Line

    “We wanted to lead with providing value to the community first and gaining trust and buy-in.”

    Bailey officially founded TutorD, an edtech platform for teachers and tutors to enable distance learning, and TutorD Scholars, a nonprofit that teaches “urban youth in-demand 22nd century skills,” in 2019.

    “We wanted to lead with providing value to the community first and gaining trust and buy-in into what we were doing,” Bailey says. “So that’s why we led with the nonprofit TutorD Scholars first, while building out the software platform.”

    Teaching made it easier to figure out the specific tools students would need on the platform and how to tailor lessons to their unique learning styles.

    Related: This Black Founder Stayed True to His Triple ‘Win’ Strategy to Build a $1 Billion Business

     ”We’re teaching [the students] in different ways,” Bailey says, “so using visual, auditory, reading and kinesthetic. [It’s] a very intentional approach.”

    Entrepreneur sat down with Bailey to learn more about how he’s grown TutorD into a successful business — and the role that Intuit’s IDEAS accelerator program has played.

    Intuit’s IDEAS accelerator program provides founders access to capital and the company’s AI-powered platform, service and experts, plus business coaching from the National Urban League and executive coaching from Zella Life to support their business and professional growth.

    Related: Over Half of Small Businesses Are Struggling to Grow, Intuit Survey Shows — But These 5 Solutions Can Help

    Learning the accounting fundamentals was a game changer

    Through the IDEAS program, Bailey got valuable exposure to the basic accounting fundamentals, like cash flow and profit and loss statements, that make or break a business.

    “That wasn’t something I had a lot of support with growing up, looking back at it,” Bailey says. “In our household, [and] it is common across Black and brown households, we didn’t have that training around finances.”

    Receiving that technical training helped Bailey and the TutorD team develop a clearer sense of where the business was headed and how its costs and sales projections would shape that trajectory, the founder notes.

    Related: Why Accounting Skills Are Indispensable for Entrepreneurs

    Streamlining the business’s messaging was also key

    TutorD used Intuit’s MailChimp, an email and marketing automation platform for growing businesses, to streamline its communications.

    Not only did the platform make it easier for people to get in touch with TutorD, but it also helped cultivate a sense of presence — making the business seem bigger than it was, Bailey says.

     ”We’re a team of five right now, and we’re dealing with other companies that are 200, 500 people strong,” Bailey explains. “And they have $20 million backed by different investors. [MailChimp] helped us appear bigger than we are to compete in the market and with other edtech companies.”

    Related: How to Streamline Your Company’s Internal Messaging and Communication

    Leaning on mentors helped during tough times

    The business coach that Bailey connected with through Zella Life also became an integral part of TutorD’s journey.

    Having a support system in place was invaluable as Bailey juggled the challenges of growing a business with major life events, he says.

    “My father passed away, and my baby came, and I had an injury, all in a three-month span,” Bailey says. “My coach had also lost his mother around that time, so we [had a] really deep connection, and he was able to help.”

    Related: How to Evolve From Manager to Mentor and Create a Lasting Impact in Your Organization

    Bailey says that the IDEAS program put TutorD in the position to scale — and gave him and his team the confidence to talk to people about their journey.

    Advice for young entrepreneurs

    Bailey encourages other young, aspiring entrepreneurs to never stop learning, seek out opportunities where there’s a need and ability to create value, connect with other founders who can serve as mentors, and leverage the community to help lay the foundation for business success.

    He’s also excited to see people embracing the “triple bottom line,” which tracks a business’s financial, social and environmental performance — and suggests anyone considering the leap to founder do the same.

    “ People are waking up to [the fact that] it’s not just about making money and some infinitely growing, making-money approach to entrepreneurship and capitalism in general, but really looking at it with a triple bottom line approach, generating sustainable profit or revenue for yourself, your family, business and shareholders, but also making an impact in the community,” Bailey says.

    Join top CEOs, founders and operators at the Level Up conference to unlock strategies for scaling your business, boosting revenue and building sustainable success.

    Amanda Breen

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  • Want to Get Into Founder Mode? You Should Be So Lucky

    Want to Get Into Founder Mode? You Should Be So Lucky

    It’s also true that when one of those groundbreaking companies matures and faces challenges, a founder has a unique ability to make bold moves and stick to the original vision when others urge a less risky course. There are certainly cases where companies struggled when founders were replaced by managers. Remember Yahoo? And of course there’s Apple, where the founder returned and restored the company to its former glory and beyond.

    But there are abundant counterexamples as well. Apple isn’t exactly struggling under Tim Cook. And consider Microsoft. Its CEO since 2014, Satya Nadella, had been a company lifer, slogging away in various divisions since 1992. Not a founder, nope. But he’s taken the company to new heights. Though Bill Gates is still revered at Microsoft, no one in the company wants him back at the top.

    And god knows, there are plenty of cases where it wasn’t management fakers but stubborn founders who drove a company into the ground. My guess is that Travis Kalanick might have benefited from listening to stodgy managers. His replacement, a management type of dude, has made Uber profitable.

    The fact is, not everyone is Brian Chesky, and no one is like Steve Jobs. The vast majority of companies never take off, and instead fade into ignominy. Very few founders get to the point where investors demand that they retain adult supervision to manage growth, because only the rarest of companies get to that point.

    It’s fun to talk about founder mode, maybe for the same reason that some of us read Ben Horowitz’s founder-porn texts with our noses pressed to the window. Founder mode, which Graham predicts will one day get its closeup in management texts, really applies only to the most exceptional founders, the ones Steve Jobs once described as “the crazy ones.” Their companies aren’t called unicorns for nothing.

    Time Travel

    In 2007, I embedded in a Y Combinator batch of 12 companies. (Starting next year there will be four batches a year, with hundreds of startups.) It was clear even then that Graham, who was extremely hands-on, had developed his views on the primacy of founders. My story ran in Newsweek under the headline “Boot Camp for Billionaires.”

    Every Tuesday during the program, Y Combinator hosts a dinner of chili or stew for the start-ups. At this first one, Graham and [cofounder Jessica] Livingston distribute gray T shirts emblazoned with one of Graham’s pithiest admonitions, MAKE SOMETHING PEOPLE WANT. A second, black shirt is bestowed only to start-ups that achieve a “liquidity event”—a purchase by a larger company or an IPO. It reads, I MADE SOMETHING PEOPLE WANT.

    Steven Levy

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