Battle-Tested Optimism: Why Entrepreneurs Like Ian Cook Move Mountains After They Leave Corporate
From Ian Cook’s fancy 27th floor corporate office in Pittsburgh he gazed out at the dilapidated warehouse where his old startup used to be. In that moment a feeling that had been simmering for a while became totally clear: he wanted his old life back.
He was the Senior Data Scientist at Highmark Health, one of the largest insurers in the country. His job was stable, well compensated, and prestigious.
But he had this persistent dull sense that he would regret it later if he did not leave soon. That his life could be more impactful. That he’d make more money later if he worked with people he loved building something he believed in. He had neither at that point. He needed both.
So Ian decided the next day to join the Entrepreneur Exodus. He accepted a lower compensation, higher risk offer from an early stage venture, Tulco Labs, which accelerated AI capabilities for high growth, early stage startups.
When he left Highmark he believed he would be the only entrepreneur stupid enough to leave corporate executive leadership. But at Tulco he discovered something strange: almost all the founders he worked with were part of the Entrepreneur Exodus. They’d left companies like McKinsey, Goldman Sachs, and Google.
The Entrepreneur Exodus refers to the more than 2,500 corporate executives who’ve left leadership positions in the Fortune 500 to launch new ventures. By almost every measure: size of funding rounds, revenue growth, resiliency during a downturn this is the most successful founder demographic in the world.
But what pissed Ian off, (and pissed me off when I left Bloomberg in 2015 to become an entrepreneur again) is that the resources that are accessible to founders are for 26 year old founders - not 42 year old founders.
$HIT THAT MAKES LIFE UNFAIR FOR EXODUS ENTREPRENEURS:
Many VCs have explicitly stated that they won’t fund entrepreneurs over the age of 30. For example, Paul Graham, co-founder of Y Combinator said, “The cutoff in investors' heads is 32… After the age of 32 VCs start to be skeptical.”
VCs expect founders to empty their savings into their startup (makes sense at age 25, when you don’t have much savings. Makes less sense where you’re 45 and have a mortgage, kids, and a 401k.)
The communities (includes incubators and accelerators) that exist for founders are mostly populated by young founders. The older you get the less these communities offer what you need. Older entrepreneurs tend to trust the advice of survivors more than the advice of observers and thought leaders. Sometimes you just need someone who will listen to you when the stress is overwhelming. Sometimes you need the empathy of someone who is balancing entrepreneurship with parenthood and spouse-hood.
“Battle-tested Optimism”
Ian attributed his post corporate entrepreneur success to ‘battle tested optimism.’ “I had a clear sense of what the unmet need in the market was, and how the incumbents couldn’t get out of their own way to meet that need. I was completely clear about why it’s so hard, but also how it could be done.”
Ian is an expert in #AI and data science. Like so many people who join the Entrepreneur Exodus he developed a total inability to do fake work with fake technology. He knew how invigorating it felt to solve a real problem at scale with real technology, and was increasingly unable to accept any substitutes. ‘Done’, for Ian, meant that it was shipped, customers were using it to solve a real problem, and it was making money by growing sales, reducing costs or mitigating risks. Too often, HighMark’s definition of ‘done’ was a PowerPoint deck, a brainstorming session with PostIt notes, a whitepaper, or a hackathon.
Toward the end of his time he learned something about himself: if it didn’t solve a real problem, if it wasn’t making money, if it’s only ostensible purpose was to participate in a tech hype cycle - then he was out.
There are entrepreneurs like Ian who are leaving the corridors of power in healthcare, investment banking, insurance, management consulting and Big Tech. (Sam Altman who left Google to create OPEN AI, is perhaps the most high profile example of the Entrepreneur Exodus.) When you have a clean understanding of an unmet need in the market, and you understand exactly how incumbents can’t get out of their own way to meet that need, you’re a much more dangerous entrepreneur than someone whose optimism is unchallenged by obstructionism.
Ian is a member of Punks & Pinstripes, a vetted community of Exodus Entrepreneurs and rebel corporate executives. I created the community so that Exodus Entrepreneurs like Ian can capitalize on all the advantages that make them the best entrepreneurs.
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