Learnings from a 20 Year Career in Tech
Andrew Capland and I break down learnings from a career in product and growth
I just talked through some of the messiest moments of my career on a podcast. Here’s why I said yes.
When Andrew Capland reached out about coming on Growing Forward, my first instinct was the one most people in this industry have: curate. Lead with the wins. Tell the stories that make the journey look like a straight line.
I didn’t do that.
Because the straight-line version of any career is a lie, and honestly, not a very useful one. The stuff that actually made me a better product leader and manager wasn’t the launches that worked or the growth metrics that looked good in a board deck. It was the moment in Nairobi when I realized every playbook I’d carried over from Silicon Valley was essentially useless. It was the product I insisted on shipping at Rewarder while my own PMs were telling me it wouldn’t work — and then watching it hurt conversion. It was working out a year of tension with a Czech CTO on a Kenya safari, no internet, nowhere to go.
That’s the episode.
Andrew has a gift for getting past the polished version of the story. We talked about what it actually feels like when your expertise stops being the answer and starts being the assumption you need to question. We talked about the transition from player to coach — why the instincts that made you a great IC will actively work against you the moment you’re managing a team. We talked about “front stabbing,” radical candor, and what happens when your leadership values collide with the culture of a company you actually need to make work.
There’s also a section near the end on building range across industries rather than going deep in one vertical that I think most people in product and growth underweight. If the book Range by David Epstein has been on your shelf unread, consider this your nudge.
This is the Growing Forward podcast with Andrew Capland. I’ll drop the link below. If you’ve been following this Substack for a while, a lot of what we cover in the episode connects directly to things I’ve written here — but heard out loud, with the real texture of what it felt like in the moment.
Quick version of what you’ll get from this episode:
Why “I was hired because I know the answer” is the wrong frame — and what replaces it
The early management mistake I made that taught me the difference between being the best person and the right person for a given task
What a Kenyan street-corner DVD vendor taught me about product-market fit
Why making yourself redundant is actually the goal