The Startup Treadmill

A look at why raising capital too early can cause your startup to fail

Two keys to building a massive SMB startup

Late last year, I wrote about SMB being the “third market” for VCs. Lots of VCs fund consumer startups. Lots fund enterprise startups. Very few truly target startups serving the small business market. Why? The challenge and opportunity for startups targeting SMB is customer acquisition: there are 30 million small businesses in the US alone; […]

Stripe’s funding: Go big or go home!

I was just reading about Stripe‘s $ 80M investment today (full disclosure: Stripe is a partner of FreshBooks where I work. And we love them…). They raised $ 80M at a $ 1.75B pre-money valuation. So, what am I thinking about this? YCombinator has yet another company in the $B club Payments is super hot […]

SMB: The Third Market

Through some happy coincidence, I have spent almost my entire career either in or serving small business. When I was a young accountant in public practice I served small business owners.  Later on, I was part of a restaurant and small retail chain. More recently, I had my own small business offering CFO services to […]