Daniel Post

This isn't the first time I've competed with a company sitting on massive funding. When I launched MeetEdgar in 2014, Hootsuite already existed and they'd already raised tens of millions, maybe hundreds of millions of dollars. But Edgar had a new approach (repeating content) and probably more importantly, were going after the creator/freelancer market. One of the biggest advantages of being bootstrapped is you can go after smaller TAMs that VC-backed companies can't touch. Having a $1 million, $5 million, or even $10 million a year company is a massive win for a bootstrapper. But it's a VC failure. The math just doesn't work out for them. They need those huge exits, those massive ARR numbers to justify the funding rounds. So as a bootstrapper, you can target these smaller, specific markets that funded companies have to ignore. Not because they're not valuable, but because they're not valuable enough by VC standards. Something similar happened with a Paperbell competitor called Practice. They launched around the same time as us and raised $10 million. From the beginning, I thought a tool focused just on coaches probably wouldn't be a match for VC backing. It's a large market, but not necessarily by VC standards. To make those venture numbers work, I figured they'd need to pivot to a general freelancer tool. Here's what I assumed would happen: they'd start in coaching, dominate that market, then pivot to something broader. And looking from the outside, they sort of did and sort of didn't. They started publishing tons of AI-generated blog content about all kinds of topics way beyond coaching. I thought it was a sign they were pivoting, but then they never really made that larger positioning shift. I don't know exactly why. Maybe they thought coaching would be a big enough market after all. Who knows what was happening behind the scenes. I always worried they would use their huge budget to just blanket and dominate the coaching space while we caught up more slowly, but they never did. Now I understand why, which I'll cover in another post. As the years went on, I realized they weren't crushing us. How did I know? We didn't hear about them much. Customers weren't constantly asking us about the differences between our tools. In our exit surveys, their name barely came up. At the time, I didn't really know how big their business was. But I knew they weren't winning because the market signals just weren't there. Over time, having a funded competitor became less and less concerning. They just weren't making much of a dent. Bootstrapped companies have inherently different goals, different success metrics, and different mechanics than VC-backed companies. Funded companies need to hit large numbers to exit or raise their next round. (And those numbers can be many things, like free users.) The numbers a bootstrapped company needs to hit can be much, much smaller and still be a huge success for the founder. This is a HUGE overlooked advantage for bootstrappers! You can win in markets that funded companies have to leave on the table. You can build profitably while they're burning cash trying to 10x everything. You can focus on serving customers really well instead of optimizing for the metrics that make VCs happy. This is part of a series on my journey thriving while our $10m-backed competitor folded. What else do you want me to write about?