On the TechTO stage ×1
First seen on a TechTO stage in 2026. Every TechTO talk is searchable — ask the archive about Mike ↗
In their words
Whenever I raised, I would practice dolphin dives. I would always make sure I could get back to zero with whatever capital I had on the balance sheet, because what you do not want to be doing is raising when you need the capital.
Every problem is a people problem. Every solution is a people solution. That's true in your business, and it's also true with the people you bring onto your cap table.
You need to know your customer and your market better than anyone in the world before you go and raise capital from somebody else.
Around the web ×1
Quick answers
Why did Mike McDerment say no to VCs for FreshBooks' first decade?
At heart it was control — he feared losing the soul of the company, especially the ability to shape how customers were served. He also knew the information arbitrage between VCs and founders was heavily one-sided back then.
What finally changed his mind about raising venture capital?
Everything else was derisked: customers loved the product, the market spanned tens of millions of businesses, and the metrics showed a repeatable acquisition model. After recruiting seven or eight executives, capital was the only thing still holding FreshBooks back. He told investors to expect 10 years and only accepted funds in their first year.
What are 'dolphin dives'?
His fundraising principle: whenever he raised, he made sure he could get back to zero with whatever capital was on the balance sheet, so he was never raising because he needed the money. If you don't need the capital, investors fight to give it to you; if you need it, you're screwed.