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Brian Flynn: Betting on the bootstrappers

The Silicon Valley equity dealer’s astonishing success rate comes down to knowing which sort of startup founder to back.

A serial entrepreneur and investor in digital businesses, Brian Flynn runs financial services platform FounderPartners to help mergers and acquisitions professionals and tech startup executives buy into or exit companies smoothly.

Since the turn of the century, Flynn has personally co-founded or backed 33 enterprises, developing an enviable instinct for the optimum time to either put money in or sell holdings.

He and his fellow FounderPartner members have an extraordinary 80 percent success rate in the businesses they’ve backed, something he puts down to knowing the type of startup leader most likely to give him a handsome return.


“I always bet on the bootstrappers to win simply because they can’t afford to lose,” the Ducere Global Leader Faculty Member says. “When the chips are down and the business is on the line, I want the guy who knows that if he doesn’t figure out how to fit that square peg into the round hole, his whole life will implode. He has no choice but to roll up his sleeves and do it.”

Flynn calls bootstrapping a mindset and a way of life.

“It’s about having such a profound conviction in your vision that the chance to realize it is worth putting everything you’ve ever worked for at stake,“ he says. “He’s like a marathon runner with clarity of purpose and laser-sharp focus to avoid obstacles and barrel forward toward the finish line.”

Asking important questions

The veteran dealmaker has more than 70 major mergers and acquisitions under his belt, including the 2005 sale of Macromedia to Adobe for US$3.4 billion in stock. What focuses his thinking is harnessing ambiguity and a desire to learn.

“One of the things that’s been my compass in driving toward success is having an incredible passion for learning and improving, and really embracing problems to find solutions,” he says. “That’s been my torch in understanding when I don’t know something and have to ask questions.”

“Uncertainty scares a lot of people, but I enjoy it because it forces me to go to my core roots to ferret out the right information.”

Part of that attitude comes from his background as a philosophy major in college.

“I love being in an opaque industry where I don’t know all the information,” he says. “Uncertainty scares a lot of people, but I enjoy it because it forces me to go to my core roots to ferret out the right information.”

One thing he is clear on is the need for boards to adapt to the digital world.

“They used to be comprised of a lot of businesspeople, and the CTO would never be invited,” he explains. “Now, the CTO is not only invited but is very important in the strategic decision-making. If you look at the big companies in Silicon Valley, the ones innovating so well are led by technical founders, like Google and Amazon.”

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