Building in Layers: The Compound Startup Playbook

April co-founder and CEO Ben Borodach joins Fund/Build/Scale to break down how he built a compound startup in one of the hardest markets in fintech: U.S. taxes. We talk about why some problems can’t be solved with a simple wedge product, how to sequence engineering, compliance, and distribution, and what it takes to operate inside complexity for years before the market catches up. Ben shares the early customer discovery work, the “science experiments” that shaped April’s product, and the cultural frameworks he and his co-founder developed before they wrote any code. If you’re an early-stage founder deciding what to build — or how to build it — this episode offers a clear playbook for choosing hard problems and de-risking them the right way. RUNTIME 48:00   EPISODE BREAKDOWN 01:08  How Ben and Daniel met + connecting over complex data problems 01:47  Ben’s background: Deloitte, crypto infra, cyber, fintech 02:51  Why pick tax? Choosing a hard, high-impact market 03:44  Outdated incumbents + the opportunity hidden in “don’t touch that” markets 04:57  Why tax innovation is so rare: regulatory hurdles and decades-old engines 05:29  Founder-market fit: complementary backgrounds + AI expertise 06:38  Translating congressional law into code + achieving 20× engineering leverage 07:25  The pseudo-manifesto: conflict resolution, culture, and founder alignment 08:40  What “compound startup” means and why narrow wedges don’t work in B2B 09:57  Stitching data, workflows, and software into a flexible platform 10:39  Building for multiple configurations across financial institutions 11:26  How complexity becomes a moat 13:01  Why compound startups require longer gestation and patience 14:46  Sequencing layers: engine → coverage → interfaces → embedded infra 15:50  The rigid annual regulatory calendar and “Manhattan-style” planning 17:13  Serving customers early: friction with the market by design 18:46  Manual work vs. automation: the constant balancing act 19:27  The early KPI wasn’t revenue  it was proving technical and trust viability 20:46  Running “science experiments” to de-risk assumptions 21:16  Investor expectations vs. seasonal learning cycles 22:47  Surviving four years of annual gauntlets before scale 23:02  Inside the regulatory maze: IRS approval, state forms, arbitrary specs 24:04  Data governance challenges: CCPA, IRS 7216, portability 25:20  Why April participates in the industry’s private governance body 26:18  Why April chose embedded distribution over a consumer app 27:32  The crumbling moats of financial institutions 29:08  Tax as the missing data layer enabling personalization 30:47  How customer discovery differed across banking, wealth, and SMB 31:07  Thousands of conversations across dozens of institutions 32:51  What April had to prove at Seed, Series A, Series B 33:49  Why rigid VC benchmarks can be unhelpful for complex companies 37:02  Headcount growth: seed → A → B 38:20  Why Ben doesn’t interview every employee anymore 39:48  Founder evolution: doing → delegating → maintaining quality 40:55  Resilience, wellbeing, and founder longevity 41:39  The mythology of 996 and why it’s unsustainable 44:07  The most common mistakes first-time fintech founders make 46:14  The one question Ben would ask if he were interviewing a founder LINKS Ben Borodach April Daniel Marcous april Raises $38M Series B to Embed Tax into Every Financial Decision April Careers   SUBSCRIBE 📥 Get the Fund/Build/Scale newsletter on Beehiiv: https://fundbuildscale.beehiiv.com/ 📸 Follow Fund/Build/Scale on Instagram: https://www.instagram.com/fundbuildscale/ 📺 Watch Fund/Build/Scale on YouTube: https://www.youtube.com/channel/UCFFH4cs2B1BKatPGs8SFRJw   Thanks for listening!    – Walter