Jerry Nettuno started Schedulicity in Bozeman, Montana, in 2009 after struggling to book his own haircut as a single father. He recruited his first developers from Denver, paid for the build himself, and launched online scheduling for hairstylists, trainers and other small service businesses at $29 a month, starting with about a hundred customers around Bozeman.
To fund a bigger team and faster growth, Nettuno raised millions from angels and one large private investor, never from venture capital. Schedulicity grew to 15,000 to 20,000 small businesses, almost 40 million consumers, $10 to $20 million in revenue and about 100 employees, but growth stalled after COVID. The company raised about $28 million in total private capital.
Looking back, Jerry says he would raise less, since every round raises the sale price needed to deliver the same return, and today he could run the same company with a fraction of the people. He sold to Vagaro, closing in early 2025, and now co-founds Pulsara, which expects about $30 million in ARR.
Key Takeaways
- Exit Math – Every round raises the bar: $200 million to match the return a $25 million sale once delivered.
- Cheaper Today – With today’s tools, the same company could run with a fraction of the employees Schedulicity needed.
- Non-VC Capital – Angels and one large private investor funded Schedulicity after Sand Hill Road meetings left him unimpressed.
- Win The Owner – Fixing the stylist’s business problems brought her 200-plus customers onto the platform without paying anything.
- Explain Fast – Many founders lose people explaining the product; be able to say it in one minute before building further.
Quote from Jerry Nettuno, Founder and CEO of Schedulicity
“I would have definitely not raised the money that we did when we did. It was only so much I could do on my own, but I think we could have bootstrapped a little bit longer and not had to raise as much money. Things were so different at that time it was hard to see, but it’s very clear looking back, obviously.
“Not to mention, in today’s world we could have run the same company that we sold with probably a fraction of the employees. When seventy percent of founders say they’d raise less, a lot of it has to do with the fact that every time you raise money, the benchmark is raised.
“The more money you raise, it exponentially increases the amount you’d have to sell the company for to get the same amount. I remember seeing an article early on that talked about that. Once you raise the bigger money, you’d have to sell the company at two hundred million to come away with the same kind of return as you could have sold it for twenty-five.”
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