Matt Harris explains why destiny is bullshit and the future is chaos (and that’s a good thing)

This conversation took place during Endeavor Week, five days of events and gatherings in New York City where members of our community from over 45 countries explored innovations and trends shaping global venture capital. This State of the Market chat featured Matt Harris, Partner at Bain Capital Ventures.

After a wide-ranging, forty-five-minute conversation spanning fintech, crypto’s ability to predict future financial institutions, building great boards, how to be a great VC and more, Matt Harris reflected on his own self. Or more importantly: on the idea that his self does not exist.

It’s a surprising idea from a man who’s achieved so much. Matt Harris is a partner at Bain Capital Ventures, where he first started working in 1995. He’s an Endeavor Board Member, mentor and ally who has helped us select and support dozens of Endeavor Entrepreneurs in 45 countries.

“This voice in your head, the thing you think of as you…is not real,” says Matt. If you take the time (and he warns it may require years) to interrogate your own sense of ego, you’ll find that your sense of self is insubstantial—an unworthy guide for your life. What is worth living for? Service. “Service can mean building the biggest company your country has ever seen, or helping others do that,” he adds. “It’s not just what you do, but how you do it. If you’re not living to gratify the self, you’re living to be of service—and that’s what matters.”

It’s a philosophy that illuminates and guides many of the ideas he shares with Allen Taylor, Managing Partner at Endeavor Catalyst, in the conversation recorded below.

Below is a summary of his key insights on global entrepreneurship shared during the panel.

Key Takeaways

• A CHAOTIC FUTURE IS GOOD NEWS: Destiny shouldn’t guide entrepreneurship, but too often circumstances like the country you’re born in have meant too much. That’s changing. Historically, the US has had the greatest entrepreneurial tradition, but a place that has “had over one hundred years of prosperity can’t continue to produce legions of people who are going to maintain hunger for their whole lives,” Matt shares. Instead, the intersection of adversity with opportunity – the ideal breeding ground for driven entrepreneurs – is moving global, and “the next hundred years of entrepreneurship will be chaotic, but better”, he adds.

• THREE PATHWAYS TO GREATNESS: The best venture capitalists tend to have one of three qualities. The first is the feeling for momentum, which is a talent that is impossible to teach. The second are natural salespeople, who have the ability to build relationships in short periods of time based on trust and connection. And the third, which can be taught, is learning to predict the future by surrounding yourself with a flow of the smartest people in the world thinking about a particular industry, and paying careful attention.

• BUILD BETTER BOARDS: Too many boards fracture because of conflicting economic alignments: a seed stage investor with a $10 million cost basis and a Series D investor with a $1 billion cost basis won’t often agree on a company’s next step. Treat a board the way you would a company, by setting values and objectives and following the same ‘storming, forming, norming’ traditions as you would in your own company’s teams.

• QUESTION YOUR OWN NECESSITY: The fact that the CEO role is important argues that you should have the best person doing it, not always that you’re the best person. Do you do your own heart surgery, or deliver your own babies? If you question your own role as CEO, you’ll also be able to ask your board members, are you the right person to sit on this board?  Generally the answer to that question is that you are the best person, as unquestionably the greatest value creation comes from founder-led companies, but the process of self-inquiry is useful in itself.  It almost never makes sense for boards to fire founders, and generally leads to disaster, but it can be transformational when founders proactively decide to hire a CEO to lead for the next chapter.

•PS, HOT TIP: Former or current CEOs of entrepreneurial companies are the best board members, full stop.

In addition to Matt’s insights on achieving entrepreneurial greatness and leaving the ego behind to do so, the panel also delved into insights from his past twenty-plus years in fintech and predictions for the future of the industry. At Bain Capital Ventures, Matt specializes in venture deals and fintech. His portfolio includes some of the most prominent fintech startups and scale-ups, such as Flywire, Justworks, and Acorns. 

Below is a summary of his key insights on fintech shared during the panel.

Key Takeaways

•FINTECH’S FIRST ERA: The first ten years of the fintech revolution took existing products and made them digital. It was a booming but unstable vector of change, because eventually incumbents would (and did) realize digitization was important. But the financial crisis bought that version of fintech an extra five years — just as incumbents woke up to its necessity, they were distracted by a near-death experience.

• EMBEDDED FINANCE WILL BOOST DECENTRALIZATION: A major contemporary problem with decentralization and cryptocurrency is accessibility: they feature challenging interfaces with frightening and high cognitive load activities. But embedded finance offers beautiful software with intuitive interfaces, and that offers potential for both B2B and B2C decentralization. “All I need to know is that payment is going from here to there,” a future customer will think, “and I don’t care if it’s SWIFT or a stablecoin rail.”

• CRYPTO IS WORTH STICKING WITH: Crypto runs a thousand experiments, and maybe 800 of those fail disastrously — which makes it embarrassing to be involved with! But if you stick with it, it always comes back, and we’re witnessing that right now with the rise of great new founders and exciting experiments. Those experiments won’t just transform crypto in its next chapter; they’ll also transform finance. Crypto is the dry run for how all future financial services will work.

Watch the full interview for the entirety of Matt and Allen’s discussion, including thoughts on generative AI, the most exciting companies Matt has (and hasn’t) invested in recently, and the difference between persuasive and knowledgeable founders. Thank you to Matt and Allen for such an inspiring and insightful conversation!