Like many early adopters, Benjamin Alarie was working with artificial intelligence well before it hit the mainstream. A business law professor at the University of Toronto, he founded the legal tech startup Blue J in 2015 with hopes of applying predictive AI to tax law.
But only a few years later, generative artificial intelligence—the segment of AI best exemplified by ChatGPT, Claude and other text-generating chatbots—was finally taking off. Users were buying in, private capital was flowing and what had once been a powerful but unflashy software segment was suddenly the center of a consumer-facing boom.
By then, Alarie told VentureBeat in a recent profile, Blue J had hit a ceiling, with revenue leveling off at around $2 million a year. So he made a high-stakes gamble and went all-in on the emerging genAI trend.
“Large language models seemed like a very promising direction,” Alarie says of his pivot. Blue J’s earlier tech, predictive machine learning, couldn’t answer every question users asked of it—“Which was really the holy grail,” the Blue J chief executive explains—leading customers to abandon the tool when it let them down.
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Says Alarie: “I had this conviction that if we continued down that path, we weren’t going to be able to address our number one limitation.”
Yet the generative AI boom offered a way out. After giving his team six months to get him a new product, and then honing the resulting system’s outputs over the last few years, Alarie says that by now he’s cut Blue J’s response time down from a minute and a half to just seconds, and more than quadrupled its net promoter score from 20 to over 80.
He also credits a partnership with software giant OpenAI, which gives Blue J early access to cutting-edge artificial intelligence models in exchange for real-world feedback.
It’s all paid off for the company. VentureBeat reports that Blue J’s $122 million Series D, announced this summer, secured the legal tech startup a valuation over $300 million. More than 3,500 different organizations are reportedly on the firm’s client list, including several Fortune 500 companies.
“What once took tax professionals 15 hours of manual research to do can now be completed in about 15 seconds,” Alarie told VentureBeat. “That value proposition—we can take hours of work and turn it into seconds of work—that is driving a lot of this.”
Perell has built multiple multi-million-dollar businesses from the ground up and is known for teaching founders how to turn setbacks into strategy. When I asked her how she built lasting success, she didn’t credit luck or timing. She credited failure and how she studied her mistakes. We are both moms and acknowledged that parenthood in and of itself is an ocean of mistakes!
Not everyone has that mindset. According to the 2024 Global Entrepreneurship Monitor Report, 49 percent of adults worldwide say they would not start a business because they fear failure. Overcoming the fear of failure is not optional; it is foundational to leadership. Here are three Perell principles every entrepreneur can use to turn setbacks into strategy.
Remember that failing does not make you a failure
“So many times something tragic happens,” Perell explains. “We use some of these challenges, and we define ourselves by them. I think that’s a huge mistake.”
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To be truly successful, you have to be willing to bounce back. If you spend your energy chasing perfection, you will never find satisfaction because perfection is unattainable. Failure is inevitable, but the lessons you learn and how you respond to these mistakes determine your trajectory.
Perell believes that small-business owners need to take personal responsibility for their mistakes and then decide what to do next.
“Do you learn from it? How do you react? How you react is actually going to make the biggest difference in how that mistake plays out,” she says. “Mistakes are inevitable on the path to success, so embrace it, learn from it, grow from it, and move on.”
Surround yourself with supportive people
One piece of advice I hear repeatedly from the most successful leaders is to build a personal board of advisers. My board includes my girlfriends and my dad. Your board can include mentors, peers, family, and trusted confidants who can offer diverse perspectives. In a recent Kabbage survey of 200 small businesses, 92 percent of respondents said their mentors had a direct impact on their growth and survival.
“You can’t do it alone, you need help,” Perell says. “It’s more of a collaborative discussion on how we can solve this together.” The right people challenge you, protect you from blind spots, and help turn failures into decisions.
Mistakes are the path to success
Perell has invested in more than 100 companies, and she notes that nearly all of them have had to pivot to survive. Very few successful businesses end up doing exactly what they started with. YouTube, for example, began as a video-based dating site before becoming a global content platform. Twitter started as a podcasting project called Odeo before evolving into social media. Successful entrepreneurs and business owners learn from their mistakes and realize that being adaptable and learning to quickly repurpose is vital.
Every entrepreneur will face a dirty unicorn, what I call the mistake that feels too big to recover from. However, if you’re willing to study it, speak about it, and shape strategy from it, that mistake might be the most valuable investor you’ll ever have.
On The Big Idea, I ask every guest about the biggest mistake they’ve made. Not because I want the story, but because I want to share their response strategy with America’s aspiring entrepreneurs and small-business owners.
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.
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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.
Governor Gavin Newsom speaks at Salesforce Tower on August 22, 2025, in San Francisco, California. Photo: Tayfun Coskun/Anadolu/Getty Images
When the Trump administration flooded the streets of Los Angeles with National Guard troops to quell minor protests, California governor Gavin Newsom put up vociferous opposition. When Texas passed an audacious mid-decade redistricting plan, Newsom spurred the California legislature to follow suit. Now Newsom is taking aim at the president with an extensive trolling campaign, often posting online in the bombastic, all-caps style of the president. Newsom’s online antics have provoked the ire of those on the right — and even some in his party — but the governor is hoovering up attention at a time when many voters are questioning the direction of the Democratic Party. On the latest episode of Pivot, Newsom joined Kara Swisher as a guest co-host and talked about the origin of his trolling strategy and what he hopes to accomplish with it.
Twice weekly, Scott Galloway and Kara Swisher host Pivot, a New York Magazine podcast about business, technology, and politics.
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Kara Swisher: I want to talk about your new role — troll-in-chief, as one newspaper put it. In the last few weeks, you’ve flooded social media with all-caps posts, insults, AI-generated memes mocking Trump and his policies. You recently got into the merch game selling MAGA-inspired Bibles, red hats, and even “Make America Gavin Again” flags, which is really funny.
Fox News has been melting down. Dana Perino said that if she were your wife, she’d tell you’re making a fool of yourself. And while a lot of liberals are loving this, you have critics on the left who say the Democratic Party needs to do more than be an anti-Trump party. I disagree. I think this is highly effective, especially that you’re not stopping. Talk about the strategy. I have theories on it, but I’d love to hear it from you.
Gavin Newsom: I just wanted to put a mirror up to the absurdity of all of this. I wish Dana Perino and others have made that point months and months, years ago. The all-cap tweets, Trump putting himself on memes as the Pope or putting him on memes as Superman or with his shirt off, on top of different superhero characters or dinosaurs. I mean, it’s comical. And yet, it’s become so normalized and socialized in a way that’s not even critiqued on the extreme right. And so I just wanted to challenge that and challenge all these pundits out there, challenge all these people, all these acolytes, people that are just fawning over a guy who puts his picture up on Mount Rushmore that does text like a 13-year-old or a 10-year-old.
It’s humiliating, it’s embarrassing. So this is a mirror, and it’s a mirror not just to Trump himself, but to these networks. These are the chatbots for the administration. And it’s not just Fox, it’s One America News, it’s Newsmax, and it’s all the folks in the right-wing media. And I’m glad they’re melting down over it. Their situational unawareness is rather jaw-dropping, and we’ll keep at it.
Swisher: How did you come up with it? You have given credit to the whole team in creating these memes. But someone asked me about it and I said, “Well, this does sound like him, the person I know.” You can be very funny and cutting and sarcastic and stuff like that. It’s sort of in your wheelhouse to do this.
Newsom: I appreciate it. Look, I think there’s one answer to that and then there’s a subtext. This thing, really, it’s about iteration. I’ve always been willing to try new things. So, I’m always trying to challenge my team: “Let’s see what works.” That’s why I went on Fox. That’s why I did the debate with Ron DeSantis. That’s why I was one of the first Democrats to go on Truth Social. That’s why I started a PAC a few years ago and only went to red states and started raising awareness and resources in parts of the country where I feel the Democratic Party walked away. And so, it’s part of that, but it’s also specifically part of what we were on the receiving end of after the fires in January in L.A.
Swisher: And before that.
Newsom: And just a different level of mis- and disinformation. And to your point about before that — look, the recall. I’m romantic. I always think all politics is local. I was sort of born and bred with that construct, but that’s not the case, obviously. And I intellectualized that, but I never fully internalized it until the recall. I had guys like Newt Gingrich and I had folks like Mike Huckabee and the RNC nationalizing their grievance. And, of course, all the folks at Fox and One America News, et cetera, coming after us.
So I started to shift our approach then. It really got into high gear after the fires, when Trump and Elon Musk were coming after us and they were winning on just rank lies about water policy and all the b.s. But what they did to federalize 4,000 of our National Guardmen and women and put 700 active-duty military on the streets of L.A. — that’s when we just said, “We’re on the other side of this.” And we told the team, “There’s no permission slip now. Not even forgiveness. You just go and we go hard, and we don’t stop.”
Swisher: And you don’t stop. That’s what’s interesting about it — it’s relentless, which is very different. I had told, I think it was Kamala Harris, you’ve got to be almost promiscuous now from a social-media point of view. You have to be everywhere constantly and not stopping, which I think characterizes this quite a bit. When you hear criticism that it’s too much or cringey even from the left or right, how do you answer that?
Newsom: You know how I answered it? I haven’t really said this publicly, but I send my team a YouTube video of Marshawn Lynch on 60 Minutes Sports when he was asked about his running style. And he says, about going into the front line, “Over and over and over and over and over and over and over and over and over again.” So this notion of communication — I could not agree with you more. Trump’s success is the simplicity with which he communicates the same thing in that cadence over and over and over and over and over again. And we move week to week. It’s Infrastructure Week, and all of sudden, now Child-care Week and it’s Foster-care Week. And as a consequence, we have weak messaging, and they’re winning the narrative war.
Illusion rules. Facts don’t matter. That’s what Fox understands. That’s what Trump understands. He floods the zone, and we’re constantly on our heels and not on our front toes. And so, what we’re trying to do is, yes, fight fire with fire with the redistricting substance and in terms of our communication style. And we’re trying to keep at it. Look, you mentioned the Patriot Store. Just look at the stuff he’s selling. Perfumes? This is embarrassing. The guy’s hawking Bibles. Ours is sold out, so if you want it, sorry, it’s sold out.
Swisher: I was hoping to get one.
Newsom: And if you want a real prediction, we’re about to put a meme coin out. And you know what? Donald Trump, we’ll see how well your coin does versus our coin.
Swisher: Wow. You’re doing a coin. Of course you are.
Newsom: We’re just trying to turn up the heat.
Swisher: Is it going to be called Gavin Coin?
Newsom: No, I think Trump Corruption Coin.
Swisher: Oh, okay. That’s a little long.
Newsom: This is one of the great grifters of our time. It’s just jaw-dropping, and none of this is normal. Again, none of this is funny. I mean, it’s funny in one respect.
Swisher: It is. You’re being funny.
Newsom: It’s extraordinary what’s going on. It’s jaw-dropping. His family is sent out before these foreign trips, doing deals. Deals are literally done before tariffs are imposed. The crony capitalism that’s going on, the people that are selling their souls in this country. I mean, that was insanity at the Cabinet meeting. And Lutnick, talking about socializing and nationalizing companies like Lockheed. And you’re worried about Mamdani and some grocery stores? And these guys are taking tidings from AMD, 15 percent from Nvidia. I mean, this is serious stuff. The grift and the corruption, the self-dealing, is something that we will continue to call out. I’m really worried about this country. I think we’ve crossed the red line. I think it is much more acute and profound than many people think. And I’m just trying to wake people up. That’s what this is all about. Wake up, everybody.
This interview has been edited for length and clarity.