Finding Startup Ideas and Building in Heavily-Regulated Spaces - Lessons from Cash App & Carbon Health
TL;DR: Ayo Omojola, VP of Product at Carbon Health and former founding PM at Cash App, shares critical lessons on building products in heavily regulated spaces like fintech and healthcare. His central thesis is that problem selection matters far more than effort - choosing a large domain rich with opportunity provides leverage that no amount of hard work on a bad problem can match. Omojola advocates for targeting markets where the leading products are old, as this signals opportunity for innovation. In regulated industries, complexity creates high barriers to entry that protect first movers. Cash App succeeded by discovering an unexploited mechanism for instant money movement that nobody else was using because it was too difficult to pull together. The article details how the Cash Card team went 'unreasonably deep' on product execution, spending weeks at factories testing 200+ combinations of card thickness and manufacturing settings to create something users would be proud to show friends. This attention to intangible details like aesthetics for an underbanked audience drove viral growth through organic Twitter sharing. Omojola also emphasizes context-sharing as a leadership superpower - assuming team members have different context than you do and investing time to share the full picture rather than just tasks. He recommends hiring former founders who are undervalued by traditional employers but bring proven shipping ability and a desire to build something meaningful.
Key Insights
- Problem selection determines outcomes more than effort - choosing a large, opportunity-rich domain provides leverage that hard work on a bad problem cannot
- In regulated industries, the complexity that deters competitors becomes your barrier to entry once you establish a beachhead
- Look for areas where it gets tedious and people stop - that's a signal nobody has gone deeper before
- Going unreasonably deep on product details like aesthetics can drive viral growth through organic sharing
- Hire former founders - they are undervalued by traditional employers but bring proven shipping ability and intrinsic motivation
Actionable Takeaways
- Evaluate startup ideas by checking the age of leading products in the industry - older leaders signal more opportunity
- When you encounter ambiguous 'no' answers without clear explanations, dig deeper - regulations written years ago may not account for current technology
- Share complete context with your team rather than just tasks - treat it like downloading your brain into theirs
- Look for former founders in career transition as hiring targets - their artifacts and public work let you evaluate them independently
- Design products that solve status-signaling problems for your target demographic to drive organic sharing
Principles Validated (15)
Own growth personally before hiring - delegation is a slow way to learn
Ayo Omojola (Cash App)
Write documentation to scale your time - content scales but your time does not
Ayo Omojola (Cash App / Carbon Health)
Write documentation to scale your time - content scales but your time does not
Ayo Omojola (Cash App)
When you hear 'no' without a clear 'why', dig deeper - regulations may not account for current technology
Ayo Omojola (Cash App / Carbon Health)
Turn serial dependencies into parallel action by questioning what is truly blocking
Ayo Omojola (Cash App)
Turn serial dependencies into parallel action by questioning what is truly blocking
Ayo Omojola (Cash App / Carbon Health)
Add management roles before you think you need them - waiting reveals missed work
Ayo Omojola (Cash App)
Hire former founders in transition - they are undervalued and bring proven shipping ability
Ayo Omojola (Carbon Health)
Hire former founders in transition - they are undervalued and bring proven shipping ability
Ayo Omojola (Cash App / Carbon Health)