HeyJaredThe Founder's Gambit
On this podcast, we talk with real founders about how they started, the big risks they took, what went wrong, and what actually worked. Honest stories, hard lessons, and practical insights from people building real businesses
- Indexed episodes, last 90 days
- 2
- Latest publication
- Sep 17, 2026
- Audience
- Checking…
- Earliest in this view
- Aug 19, 2026
Latest episodes
How I Raised $10.5M From a16z With a Boring Startup (opens the original)
Read excerpt
Oskar Block made $1M ARR at 18 building sports-betting models, walked away because it didn't feel meaningful, joined McKinsey to hunt for a real problem, and left the week before Christmas to build AI agents for patent litigation. Six months later, Stilta had gone from $18K to $102K ARR in two weeks during YC and raised $10.5M from Andreessen Horowitz. In this episode, he breaks down exactly how he got into YC with no product, closed customers in the most conservative industry on earth, and turn
How I'm Building a Billion Dollar Company (opens the original)
Read excerpt
A girl cancelled their dinner reservation the day of. Rather than eat the $100 cancellation fee, Jeff Wulkan built an app to find a replacement, then quit a 20-year aviation career and put $250,000 of his own money into it. Today Plus One is adding roughly 7,000 users a month on a lean budget, 60% of them organic, while marketing in exactly one state.What we cover:- The cancelled date that started it and the text he sent her six months later- Why he flipped the script on dating apps: plans first
Publishing over time
Last 90 days. Choose a month to open its work.
Recurring subjects
Named in the text we hold. One piece can cover several.
Audience
No verified audience measurement yet.
About this data
Counts cover the work we have indexed. Tone needs enough text and a confident classification. Excerpts and episode notes are not full articles or transcripts.
Identity or attribution wrong? Suggest a correction.