I've been asked a version of this question probably a thousand times: "How did you end up doing what you're doing now?" And the honest answer is: I didn't end up anywhere. I'm still in motion. But the path that got me here looks nothing like the career-services flowchart I was handed at UC Davis in the early 1990s.
That flowchart was: pick a major, get a job at a big company, stay 20 years, get the pension, play golf. If you were ambitious, you substituted "Big 4 consulting" for "pension." If you were really ambitious, you went to Wharton or HBS and then to investment banking. There was a narrow set of legitimate paths and a wide set of illegitimate ones, and the unspoken rule was: straight lines win.
I took zero straight lines. And every detour that looked like a mistake at the time turned out to be the foundation I'm building from now.
Detour 1: PeopleSoft, which became Oracle
My first real job after college was at PeopleSoft, pre-Oracle acquisition. It was enterprise software before enterprise software was cool. It was the early days of ERP, CRM, HR tech — the plumbing of the modern corporation. I spent my 20s learning how big companies actually make decisions about software, which is slow, political, and full of people whose incentives don't match what they tell you in the room.
At the time, I thought I was just doing a job. In retrospect, I was getting a master's degree in enterprise software buying behavior. Every deal I've closed in the last 20 years — in digital marketing, in martech, in services — was informed by what I learned watching Fortune 500 CIOs decide whether to approve a $3 million software license. That pattern recognition is not something you can buy. You have to earn it in the room.
Detour 2: Japanese performance vehicles
Between stints in enterprise software, I did something that looks completely unrelated on paper: I imported Japanese performance cars. Not as a hobby. As a business. Skylines, Supras, the kinds of cars that had a cult following in the US before the law made it easier to get them here.
What I actually learned in that chapter had nothing to do with cars. I learned international logistics, customs regulations, cross-border payments, supplier trust, the difference between a handshake deal in Japan and a contract deal in the US, how to manage a product pipeline where every unit was unique, and how to sell to a customer base that cared more about the story than the spec sheet. I learned how to build a brand around something scarce, which is the whole premise of luxury.
When I later ran a beauty trade network connecting Korean brands to Latin American buyers, I wasn't learning from scratch. I was reusing the muscle from the car business. Different product. Same operating principles.
Detour 3: Real estate, the $30M chapter
In the mid-2000s, I did a few years in residential and commercial real estate. Bought and sold a meaningful volume of property. Made real money. Lost some of it in 2008 when the music stopped, like everyone did. Rebuilt.
The real estate years taught me three things that I don't think I would have learned in tech: how to read a capital stack, how to think about leverage at personal scale, and how quickly a "sure thing" can become a "problem" when the market turns. I watched smart, rich, experienced people get crushed in 2008 because they had confused "hasn't gone wrong yet" with "won't go wrong." That's a lesson I carried into every deal after that, and it's the reason I'm cautious about leverage in a way that sometimes looks old-fashioned to younger operators.
Detour 4: The public company years and the fire
Running a public company was the first time I tried to do it at real scale. Twelve acquisitions. A roll-up strategy in digital marketing services at a moment when the market was ready for it. It looked, for a minute, like the answer — the thing the detours had been preparing me for.
Then the public markets turned. Rebuilding from a hard stretch teaches you what no curriculum ever will. Most people would have walked away. I didn't. I rebuilt.
This detour wasn't a learning experience. This detour was a crucible. And what came out the other side was an operator who does not get rattled. There is nothing a boardroom can throw at me now that I haven't already survived. That's not a brag. That's just the actual risk profile of my nervous system now.
Every detour looked like a mistake at the time. Every one became an asset. The only mistake I ever made was the detour I almost refused to take because I was worried about what it would look like on a résumé.
Why the linear path is a lie
Here's the thing I wish someone had told me at 25: the linear path isn't actually a path. It's a story somebody made up to sell you comfort. The people whose careers look linear from the outside are either early in them, or they've retroactively cleaned up the narrative, or they optimized their life for the appearance of a straight line at the cost of what they actually wanted.
Real careers, by which I mean the careers of people who build meaningful things, look like a web. They have false starts, detours, failed experiments, crucibles, rebuilds, and restarts. They look chaotic in real time and inevitable in retrospect. The people living them can't connect the dots forward, to borrow the phrase, but they can always connect them backward.
The atypical path is not the exception. It's the norm among builders. The linear path is a marketing story sold to people who want to feel safe while they work for companies built by people who refused to believe it.
What the detours actually give you
Each detour gave me something I couldn't have gotten by staying on the "right" track.
Pattern recognition across industries. I've seen enterprise software, international trade, real estate, digital services, beauty, and public markets. I recognize patterns in the beauty business because I've seen them in car importing. I recognize patterns in AI services because I've seen them in early CRM adoption. No specialist has that cross-industry library. The generalist's advantage is underrated because it pays off later, not sooner.
Scar tissue in the right places. The people who've never been publicly wrong are brittle in ways they don't know. I'm not brittle. I got broken and put back together enough times that the broken places are actually stronger than the original parts. Hemingway wrote about that in A Farewell to Arms. It's true in careers too.
A tolerance for ambiguity. When you've taken enough detours, you stop needing to know where the road ends. You learn to operate with partial information, make decisions without perfect data, and adjust in flight. That tolerance is the single biggest predictor of founder success, and it only comes from reps.
A story worth telling. The atypical path is, in the end, the thing that makes you interesting to the people who matter. Investors bet on operators with real stories. Customers buy from brands with real stories. Kids listen to parents with real stories. The linear-path résumé doesn't tell a story. The atypical path is the story.
The challenge
Name the three detours that made you uniquely qualified for what you do now.
Most people can't do this on the first try, because we've been trained to hide the detours. We edit our LinkedIn. We skip the gap years. We don't mention the failed venture. We pretend the real estate chapter "wasn't really what we did."
Stop doing that. Name the three detours. Write them down. Ask yourself what each one actually taught you, and how you use that now. You'll find that the things you thought were weaknesses — the non-obvious moves, the failed bets, the crucibles — are the exact things that make you different from every other operator with a clean résumé.
The atypical path is not a detour from the destination. The atypical path is the destination. Own it. It's the most expensive asset you have.