How I Raised $10.5M From a16z With a Boring Startup
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 turned a $3M raise into $10.5M.What we cover:- How he built a $1M ARR sports-betting business at 18 (and why he quit it)- Treating McKinsey as a 5% startup research job: the questions he asked in every expert interview- Why he picked patents, an industry everyone thinks is boring- Getting into YC with no product, no customers, and no revenue- Why four co-founders works (and the acquisition that taught him people matter more than product)- Missing his YC revenue target three times in a row, then going $18K → $102K ARR in two weeks- The anti-selling trick that cut his sales cycle from months to weeks- Manual LinkedIn outbound that actually converts in a conservative industry- 150 investor meetings in 9 days: how he scheduled them to build momentum- Why he told investors he was raising $3M, not $10M- FOMO as the most important tool in fundraising, and how the first term sheet triggered the rest- Why he chose a16z over higher valuations- The comfort trap after raising too much moneyKey takeaway: Find the bottleneck, solve it, move to the next one. Set targets that feel impossible, because getting halfway there every two weeks compounds into more than you thought possible.🔗 Links:Stilta: https://stilta.com/Oskar on LinkedIn: https://www.linkedin.com/in/oskarblock/
