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Tag: founder advice

  • This Founder Cold-Emailed Salesforce CEO Marc Benioff 53 Times Before He Got What He Wanted

    Harry Stebbings, founder of venture capital firm 20VC, send Salesforce CEO Marc Benioff 53 emails before the business leader finally agreed to appear on his podcast, 20VC. Stebbings discussed his strategy November 12 on Wouter Teunissen’s The Biography Podcast, and shared some tips for making your communications stand out.

    To Stebbings, nothing matters more than relationships. That’s why, in a world where you can find anyone’s email online, he thinks “everyone should learn to be a really efficient SDR, but essentially a stalker.” 

    The 29-year-old puts 30 minutes a week toward “hustle time,” when he thinks about who he wants on his podcast and how to make it happen. To this day, he said he’s roped most of his guests in with cold emails.

    Stebbings told Teunissen that while cold emailing is “super learnable,” it’s ridiculous that “so few people can do that well.” So he offered some clear cut advice. 

    How to Write a Cold Email

    The subject line should be “f—-ing clear” and to the point, as should the body of the email, Stebbings said. Skip the filler phrases.

    “I hope you’re well? Never,” he said. “Who says I hope you’re unwell? No one.”

    Instead, Stebbings advises to immediately state your objective. Tell the person what you’re asking and how much of their time you need.

    Provide some background information to steer them towards agreeing to your ask. In Stebbings’ case, he lists the subscriber count and a few guests he’s had on the podcast to give his request some validity. 

    Next comes a “P.S.” followed by a personal touch. Stebbings tried a few different routes, like offering Marc Benioff his favorite whiskey, or mentioning his holiday home and favorite vacation spot. 

    “Wow,” Stebbings said, imitating a recipient of his emails. “Super clear, really well outlined, and holy s–t he’s done his work on my favorite whiskey. Well done.”

    Don’t Delay the Follow Up

    If you’re lucky enough to connect in person, don’t wait until the day after to reach out. Stebbings said he always emails in the Uber home from the event or dinner.

    “It’s so important because it just shows them that you’re on it, and it’s fresh in their mind,” he said. “Not hard at all. Honestly, sometimes it can be a copy and paste and you just put the first line as personalized. Makes such a difference.”

    His slew of emails paid off when Benioff came on the podcast in a September 2023 episode. Benioff shouted out his unrelenting efforts in a post on X.

    “Harry must have texted and emailed me 100 times before I agreed to be on his podcast,” Benioff said. “Persistence pays Harry.”

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

    Ava Levinson

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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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  • Why Your Age Doesn’t Matter For Startup Success

    Do you imagine entrepreneurs as funky, hoodie-wearing twenty-somethings? Actually, research shows that the average founder age is significantly older. But is there a right age to launch a business? And does it really matter for success? 

    Busting the myth: The entrepreneur life cycle

    Young founders typically dominate media narratives. Glossy covers celebrate teenage tech moguls, billionaire whiz kids, and private equity unicorns. Annual TechCrunch award winners average 29 years old. Even Mark Zuckerberg famously quipped, “Young people are just smarter.” Funding programs can institutionalize this perception. For instance, the Thiel Fellowship caps its $200,000 grant to founders under 22 who either skip or drop out of college.  

    Naturally, the unbridled optimism, energy, and perceived invincibility of Gen-Z offer much to potential business success. Not yet hardened by reality or regulation hurdles, enthusiasm can be a catalyst for growth. Hope fuels exhausting funding rounds and endless all-nighters, even if at  a personal cost.  

    The willingness to move fast and break things can pay off. At 19, Sam Altman co-founded Loopt. He later became co-founder and CEO of OpenAI, the $150 billion startup. At 21, Wang Ning founded Pop Mart, the force behind Labubu’s toy figurines. 

    At 22, Britain’s Dragons’ Den investor Steven Bartlett co-founded Social Chain before the popular Diary of a CEO podcast, alongside FlightStory, and ThirdWeb.  At the same age, Alexis Ohanian co-founded Reddit which now hosts 510 million users. Two decades later, he still hunts for value. Age didn’t matter.  

    Few exhibit signs of slowing down—a salutary reminder to moderate pace. The smarter entrepreneurs tune in to the voice of experience to avoid rookie traps.

    Risk appetite shifts in your 30s or 40s. Confidence and experience compound. Networks deepen. This entrepreneurial milieu has a long list. 

    At 30, Jensen Huang co-founded NVIDIA, the first semiconductor company to hit $1 trillion market capitalization.  Boeing, Carlsberg, and Salesforce boast 35-year-old founders. Equally, Lenovo, Intel, Zara, and HTC boast 39-year-old founders. 

    This should reassure late starters. In fact, research shows that success peaks later.

    MIT and Kellogg researchers  analyzed US Census datasets of 2.7 million founders, concluding that the average age was 42 years. Digging deeper, they determined that among the fastest-growing startups over a five-year period, the average age was 45. 

    Moreover, founders in their 40s succeeded twice as much as those in their 20s, attributed to greater experience and connections. 

    Some prefer the comfort of the corporate cocoon. Others seek to satisfy unfulfilled ambitions. Midlife opportunities can emerge in early retirement or post redundancy. 

    Life events also shape decisions. Both CEOs and graduates reappraised careers during the pandemic. 

    Beware stereotypes. At 54, Elon Musk still operates at breakneck speed, having launched SpaceX, X.com, Tesla, and Neuralink. He’s now considering  Grokipedia.  

    Empire builders love the buzz. Warren Buffett delivered into his 90s. As Berkshire’s 2024 earnings rose 27 percent, he recently confirmed his successor. Michael Bloomberg, 83, remains active at Bloomberg L.P., having returned as CEO in 2014. Nonagenarian Rupert Murdoch stepped down at 93 to become chairman emeritus of Fox Corp and News Corp. 

    If undecided on the startup journey,  simple solutions can make this easier.

    Equal opportunity knocks

    Entrepreneurial failure is notorious, yet success outliers dominate headlines. We read about superstars, not those left on social welfare. 

    Professor Shikhar Ghosh analyzed 2,000 venture-backed firms. He estimated that 95 percent miss initial projections, 70 to 80 percent fail to deliver projected returns, and up to 40 percent fail outright. 

    As outlined in my book Tune In, leadership misjudgment stems from predictable traps rooted in bias. With failures invisible, success is easier to recall. Wins are more salient and wrongly become the norm. Aspiring entrepreneurs should remember that normalized exceptions are not a base rate around which to build their business.

    In today’s AI-dominated world, tech entrepreneurship takes center stage. The very word conjures up a stereotypical image of Silicon Valley wunderkinds. Think Stripe’s Collinson brothers or Bumble’s Whitney Wolfe Herd.  However, in pursuit of hyper-growth, the slippery slope beckons. 

    When FTX left an $8 billion hole in customer funds, Sam Bankman-Fried received a 25-year federal sentence. Former Theranos CEO Elizabeth Holmes received an 11.25-year sentence for defrauding customers with fake blood tests. Ironically, both launched businesses in their 20s.  

    Relentless entrepreneurial ambition costs. Adam Neumann’s WeWork was valued at $47 billion at its peak, yet it imploded ahead of its 2019 IPO. 

    Lionized founders with uncontrolled egos, poor oversight, and mythical stories teach aspiring entrepreneurs valuable lessons. The takeaway isn’t to avoid tech but to judge by fundamentals, not by founder mythology. 

    The world has moved on. It’s too simplistic and outdated to attribute entrepreneurial success to age. Great ideas, networking, and hard graft always prevail, aided by luck and opportunity. 

    The best breakthroughs can materialize at any age and in any setting. It’s never too late to start.

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

    Nuala Walsh

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  • Fractional or Full-Time Help? Growing a Business Requires Founders to Know the Difference

    Hiring a team can be daunting for many founders, especially when it’s their first company. It’s like leaving your toddler with a babysitter for the first time. Trust me, I get it. One mistake can be detrimental. If you bring in the wrong person to a team, it can derail any progress made and cost you thousands in the process. That’s why hiring fractional help can be of assistance.

    Think about it like testing before buying. But when should a company seek full-time help and when is it better to go with fractional hires? There are some important factors to consider. 

    How to tell if you need help 

    If any of the following are true, you’re overdue for a hire or more. These are just a few of the main pain points.   

    • You’re replying to customer support at midnight.   
    • You’re spending more time on spreadsheets than on strategy.  
    • Your to-do list seems to be never ending.   
    • You’re managing people and projects that should be done by someone else.  

    As a CEO, when you spend too much time on work outside of your expertise, you know support of some kind is necessary. Many CEOs get stuck in the doing—managing projects, overseeing tasks, and solving immediate problems. They may be the busiest people in the business, but unfortunately that often does not translate to revenue. Hiring experts to fill your gaps is the best way to grow sustainably.  

    A few years ago, a founder contracted me to help with declining profits and “hiring problems.” Within two weeks of discovery interviews, the real picture became clear. He was spending more than 80 hours a week managing his team members and completing tasks far below his pay grade. The interesting part is that he had a team to rely on, but he didn’t have the tools to succeed with the team.  

    Consequently, he had no time to grow the company. That was the real issue. I persuaded him to bring in a fractional chief of staff and that completely transformed his organization. The CEO’s mindset shifted from reactive to proactive, and two years later, he sold the company for $2 billion.   

    Fractional versus Full-time  

    You know you need help, but you’re unsure what type. If you don’t have enough work for someone to fill the role full time, but you need the help of an expert, fractional is the way to go.   

    When I first founded my company, I hired a fractional social media expert. I am a Baby Boomer, so it is the furthest thing from my expertise. Years later, when I had the funds and many more projects to delegate, I hired a social media manager full-time. Another reason to make a fractional hire is when you simply can’t afford full-time help. Expert fractional work won’t be cheap, but it will give you an expert for less money.   

    The long-term effect   

    A mistake I see many founders make is not hiring help soon enough. Although it requires investment early on, it saves a company money in the long run.   

    Imagine you attempt to do it all yourself for the first few years. You will save cash in the short term, but it will cost you in the slowed and possibly stagnant growth of your company. One person can’t effectively do the work of many people. Also, it’s 2025. Everything moves faster than ever before, and without the proper help, you can quickly have a disaster on your hands. Instead, make a small investment now to prevent turning into one of many organizations that operate reactively rather than proactively.   

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

    Carol Schultz

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  • This Wellness Entrepreneur’s Story Proves the Power of the Pivot

    Shizu Okusa, the Wall Street alumna turned wellness entrepreneur behind Apothékary, which Okusa described as “Mother nature’s pharmacy,” shared on Yahoo Finance‘s The Big Idea about how to jump into change with both feet. Everyone will have to pivot at some point, whether they are forced to through a firing or layoff or if they are inspired to start a new company. In fact, a recent survey found that 50 percent of U.S. workers are actively considering switching industries. The key is to use the pivot to grow, evolve, and take the risk!  

    Recognize when it is time for change.

    Okusa built her early career in the high-pressure world of finance before realizing it no longer aligned with her aspirations. That clarity pushed her to explore her Japanese roots and passion for herbal medicine. The result was Apothékary, a plant-based wellness brand now carried by major retailers like Ulta and Sprouts.  

    Knowing when your current path is unsustainable is the first step toward making a bold shift. “There’s a visceral reaction in your body when you just know after day in day out, and you show up to work and you’re not present,” Okusa explained. 

    Treat pivots as part of the entrepreneurial journey.

    Okusa shared that entrepreneurship is constant evolution. “You have to go into business knowing that you’re going to pivot,” Okusa said.  

    From sourcing ingredients to scaling distribution, she has reframed pivots as a natural part of running a business rather than signs of failure. That mindset shows up in Apothékary’s journey. The company launched with herbal powder blends, but customer feedback was not exactly complimentary. Instead of ignoring it, Okusa rebranded and pivoted into tinctures that were easier to use and more palatable while still potent. 

    Her biggest pivot, though, came earlier. Before Apothékary, she co-founded JRINK, a cold-pressed juice brand. When that business was acquired, she shifted focus to her own health struggles and her Japanese roots in herbal medicine. That decision became the foundation for Apothékary’s plant-based wellness products. 

    These examples underscore Shizu’s point that pivots aren’t setbacks, they’re part of the path forward, and you should keep going. That mindset shift can help founders approach obstacles with flexibility and optimism.  

    Authenticity is key. 

    For those considering a career change, Okusa recommended researching the space and identifying what makes your offerings unique. That might be testing an idea as a side project, exploring funding options, or simply talking to others who have made similar transitions.  

    “Do everything and work for someone who you think is going to be in the industry or in the space you want to start your business in and learn it all, even for free,” Okusa said.  

    That kind of groundwork helps entrepreneurs uncover real problems worth solving. “You lead with the problem and then the solution comes forward,” she added. One real-life example is to look at the comments on your ads. 

    Career pivots aren’t easy, but Okusa’s journey shows they are possible with clarity, flexibility, and intentional steps. Whether you are moving industries or redefining your business strategy, change is less about the perfect moment and more about authenticity. 

    Elizabeth Gore

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  • If I’m being honest, I didn’t have what it takes to be a founder | TechCrunch

    If I’m being honest, I didn’t have what it takes to be a founder | TechCrunch

    Over the last couple of weeks, I’ve been working with some truly spectacular founders. One guy was a three-star general at one point. Another is in the U.S. because his research is so far ahead of the AI learning curve that the U.S. State Department issued him an O-1 extraordinary ability visa. Another had a doctorate and a stack of patents in his name.

    If you’re working at a VC firm, it isn’t unusual to meet such extraordinary people. You’ll see a steady stream of people waltzing in with pitch decks, prototypes and résumés. VCs are on a perpetual quest to discover and invest in extraordinary startups, those rare gems with the potential to disrupt markets, innovate industries, and disrupt the hell out of everything in sight. And if you’re an aspiring startup founder, you may wonder if you have what it takes to attract such investment and thrive in the competitive startup ecosystem.

    Unfortunately, what I’m seeing out on the fundraising trail right now is that if you don’t have perfect founder-market fit, fundraising is getting hard.

    Of course, that got me thinking about my own startups. If I map myself against the standards of fundraising today, none of my startups would’ve had a gnat’s shadow’s chance of raising money.

    Haje Jan Kamps

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