If you’re getting this, it means you’ve been a part of my journey in some way. Thank you! I’m writing down some of my reflections from making the leap to founder after years in Big Tech life. I hope you find it useful, or at least entertaining.
I wanted to start a business from a very young age. In elementary school, I traded pogs and used the proceeds for lunch money. In high school, I ran a soccer broadcasting website and an underground bookie operation. In the military, I had a couple of side-hustles (shhh!).
The dream was always to build something big. But life had other ideas—school, mandatory military service, moving to the U.S., getting the right immigration status, having kids, all of which made that dream harder.
So instead, I did proxies for entrepreneurship: I was an engineer to the core, but moved into product management. I got an MBA (go Bears!), which felt both smart and embarrassing—like strapping on training wheels as an adult. I knew the YC line: just start something. But it never felt like the right time. I suspect it’s the same as having kids: there never really is a right time.
Four years ago, after 12 years in Big Tech, in the thick of the COVID lockdowns and on paternity leave with my second daughter, I decided to make the leap. The startup idea was deeply resonant with me: help people make sense of their memories through photos – a mission that hit home personally (I was drowning in snapshots) and professionally (I’d launched monetization for Google Photos). I spent the next few months in “pre-founder” mode – prototyping and user-testing on stolen weekends – before going all in.
Into the wild
As they say, everyone has a plan until they get punched in the face. And as expected, despite all the pseudo-preparations, when I finally arrived, startups felt like a foreign land. A more reasonable person would have considered working in a startup before founding one, and that would be my first advice to my former self.
Luckily, I had guides in these lands: friends, mentors, early believers, many of whom turned angel investors. My guides helped me from my “pre-founder” stage, all the way to this day. If you're reading this, you’re probably one of them – thank you.
Since then, I’ve had the chance to pay it forward. I talk to a lot of pre-founders – people thinking about making the leap, or leaving BigCo life for something smaller and weirder. I found myself recounting the same stories, repeating the same advice. So I decided to write them down.
This is the first in a series of posts. It’s partly for aspiring or early founders, but it’s mostly advice to my former self. Four years of ups and downs, successes and failures, hopes and letdowns, with very little time to reflect on them. Writing is a forcing function to sit with it all, figure out what I’ve learned, and maybe help someone else along the way.
For PMs and For Everyone Else
The PM-to-founder path is a common one. At some level, I feel like most product managers daydream about starting something. Or maybe that’s just the False consensus effect talking.
PM is a kind of startup simulator. You’re responsible for the outcome, even if you don’t control all the inputs. You rally the team, steer the ship, and make the tough calls. People like to call it “CEO of the product,” which is true in some ways and laughably false in others. I’ll write about both.
If you're a PM thinking about making the leap, you’ll probably get the most out of this series. But I hope it’s a fun read for anyone curious about startups—or who just wants to follow the story of a guy from BigCo trying to build something from scratch. Over time, I might branch out into other topics too.
On Cadence and Intent
Confession: whenever I get a new “substack announcement,” my first thought is, “Good luck keeping that up.” I’ve tried to launch newsletters in more official settings – their survival rate is worse than a helium balloon in a toddler’s hand.
So: no promises. I’m writing these posts early in the morning, before the kids wake up. I’ll post these once every other Sunday-ish, until I run out of things to say – or until my kids start waking up earlier (please, no).
Few things make me cringe harder than “think-fluencers,” and I have no desire to go viral or monetize this. This is meant to be a salon conversation, not a packed arena. If something resonates, if it sparks a thought, or if it helps you feel seen or inspired, that’s enough.
In the next few posts we’ll explore:
House cats and street cats: the different attitudes needed in BigCo and a startup
The emotional edge of being a founder
Why exactly is consumer hard?
Swiss-army knives and bottle-openers: surviving consumer’s low attention spans
ZIRP management: the precursor to “Founder Mode”
I have the outlines for some of these in my Morning Notes, which is an accumulation of my thoughts over the years and a “staging area” with messy ideas. Let me know if you run into gems that you’d like me to explore more.
Thanks for reading so far! Feel free to reply with any thoughts – you’re getting this exactly because I’d love to hear from you :)
This is awesome! can't wait to read it all!
Thanks for sharing; looking forward to reading more of your stories and insights!