Unpopular opinion: Most B2B startups fail because they build for startups instead of boring mid-size companies
Every founder I meet is building for either indie hackers/solopreneurs or trying to land Fortune 500 logos.
Nobody wants to build for the 200-person logistics company in Ohio or the 400-person marketing agency in Bangalore. And that's exactly why there's a massive opportunity there.
Here's what I've learned building for this "boring" segment:
They actually pay. They don't need a free tier forever. If you solve a real problem, they'll give you money in week 2.
Their problems are unsexy but painful. Nobody writes a TechCrunch article about desk management or internal workflow automation. But these companies lose thousands of hours a year on this stuff.
Competition is weaker. Every YC startup is fighting over the same developer tools and AI wrappers. Meanwhile, mid-size companies are running critical operations on spreadsheets and WhatsApp groups.
They're loyal. Enterprise clients will replace you the moment a bigger vendor adds your feature. Mid-size companies that love your product will stick with you for years.
I'm building in this space right now and the biggest challenge isn't product — it's convincing other people (investors, advisors, even friends) that it's worth doing.
Anyone else building for the "boring middle"? Would love to compare notes.