The Decathlete.
And why I stopped trying to pick a lane.
I am not the best at anything.
If you’re looking for the world’s foremost expert on AI infrastructure or venture investing or founding companies or trading stocks or any one thing, I’m probably not your guy. There are smarter people on every one of those topics.
What I am is sneaky-dangerous across a bunch of them simultaneously.
That’s the decathlete. Not the fastest, not the strongest, not the best jumper. But when you add up all ten events — when you need someone who can run, jump, throw, and think — the decathlete wins the whole thing.
I spent years being (more than) slightly embarrassed by this. The guy who could hold his own in almost any room, but never fully belonged in one. The investor who was also a founder who was also an operator who was also an analyst. Pick a lane, kid.
I never did. Turns out, I was trained not to.
At Penn I did the M&T dual degree program across Wharton and engineering. I suppose it was a template for what was to come.
The events, roughly in order:
1996-2001. Sell-side research and investment banking. Furman Selz / ING Barings, then (JPMorgan) Chase H&Q covering Internet infrastructure. Financed the dotcom boom (bubble), watched it explode (burst), learned what hubris at scale actually looks like.
2002-2005. Hedge fund partner and analyst. MLH Capital with Ed Hajim and then Ardsley Partners. Ed taught me two things I’ve never forgotten: hubris is terminal, and the long term is just a string of short terms put together. Then he fired me. (And got me the job at Ardsley, who also later fired me.) I’m a better analyst now than I was then — experience gives you pattern recognition and epistemic humility simultaneously. (Whether you wanted it or not.)
2007-2010. Co-founded Tigerbow — send a real gift via email. Built it from concept to live platform. Wound it down. That’s the polite version.
2010-2011. Co-founded Philo — Foursquare for TV. Raised >$1M, built the product, negotiated an acquisition to a private company that later failed too. I made no money. What I got was “the education.”
“You’re not a founder until you’ve shit blood and drank at breakfast.”
— Me, on founding companies.
2012-2014. EIR at Broadway Video Ventures (Lorne Michaels’s thing) and Comcast Ventures. Sourced deals, explored ideas, and — according to my dear friend David who ran Broadway Video Ventures — spent a meaningful amount of time on his couch working on my mortgage refi. (Not entirely untrue.)
2014-2018. AWS, first tour of duty. Co-built the startup BD team — the playbook, infrastructure, startup GTM effort. Helped expand coverage to >100K startups and >10K partners. Learned what platform-scale institution building actually feels like.
2018-2019. Stripe. Left AWS to help co-build the startup growth team at one of the great hypergrowth companies of the era. Stripe was — and is — a remarkable company. The role was… not what I expected. I left after a year and a day. (Not a coincidence.)
2019-2023. AWS, second stint. At Amazon they call this a boomerang. I call it Hotel California — you can check out any time you like, but you can never leave. (Until they do another dozen RIFs.) Was nice being back, but no longer felt like I was in the room where it happened. But it was home until it wasn’t.
2023-present. Porch Capital. Which brings us here.
Throughout all of it, angel investing — in CoreWeave, Twitter and LinkedIn pre-IPO, Groq (pre-Nvidia), Crusoe, Throne Science, and others. Not as a strategy, but as a compulsion. Or maybe an “entrance fee.” It’s an expensive hobby. Being a great angel investor is a wonderful life, but you can only get there by being ultra-successful or being born into money. VCs are paid to invest. An angel’s job is to be rich. (It’s a very nice gig if you can get it.)
I am neither, which makes me either an idiot or an optimist. Or both.
None of these events, alone, makes me the best in the world at anything.
All of them together make me someone who can look at an AI infrastructure company and think about it from the perspective of a founder, operator, investor, analyst, and builder — simultaneously, in real time, without having to go look things up. (Zip it, ChatGPT and Claude — and sometimes Gemini 🤫.)
That’s what Porch Capital is. Not a fund. Not a firm. Not (just) a newsletter. A decathlete sitting on the porch with something to say.
I spent a long time thinking I should pick a lane. I’m done with that….
Porchdog. Decathlon Champion.
What can I say. I owe it all to Little Chocolate Donuts. (RIP, John Belushi.)