Ha, it boggles my mind this concept of raising money and then creating something that’s useful for the market, only to have to go back for more money round after round. It just never felt like the natural path forward for us. We made a decision early on at ProdPad that we weren’t going to go for funding, and that instead, we were going to focus on building something of value that people would pay for, and fund it that way.
That path was only an option because both me and my co-founder were builders and were able to make a working, sellable version of our product ourselves. We had a couple hundred customers and nearly $15K MRR before we looked at growing our team and getting help. It took time to build, but in hindsight, certainly not more time than we would have spent knocking on doors trying to get the multiple rounds of funding we likely would have needed (as everyone knows, you never just get one round!)
It was also harder to build trust in the market in early days. For some reason, large companies tend to be distrustful of bootstrapped businesses, even if they are profitable and self-sustaining. Because we kept our team small (we’re still fewer than 30 people! 
), it meant that we’d sometimes be compared against competitors with 100s of team members, even if they only had that team because of a huge amount of debt. Thankfully, the balance swings over time, and we’re now the player in our market who’s most suited for large enterprises. After a certain number of years, enough ‘proof’ from other companies using the product (we’ve now got well over 1000 companies worldwide), and building our team and processes out to meet the needs of large companies, we found that the large deals were easier and easier to close each time.
For anyone who wants to know about our enterprise offering, check it out here: Product Management Software for Enterprise