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03:44  Outdated incumbents + the opportunity hidden in “don’t touch that” markets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

 

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Thanks for listening!

 

 – Walter