I recently got on a call with a potential coaching client who asked me the best way to create momentum during the fundraising process. And it got me thinking… “what’s been true in my own successful fundraising experience… as well as the 150M raised by those I’ve mentored/advised?” Turns out, there were some consistent (and repeatable) markers that can make the difference between a fast and effective fundraising round…

I’ll never forget one of the first times I pitched an investor. I was literally pacing in the back alley of a SF coffee shop with one of those ugly pre-2007 cabled headsets plugged into my iPhone. I had a warm intro to the investor. Things were going smooth. But with just ONE single misstep, I got those gut-wrenching words no founder ever wants to hear:

When I started my SaaS (that stands for Software-as-a-Service) startup Flowtown my co-founder Ethan and I had a tough decision to make... How do we fund the company? Even though I had the capital to self fund the whole thing, as I had just sold my previous company Spheric, he was 23 and didn’t have a penny to his name. So this is what I did... It was Friday, and I said, if you can find a way to raise

How do you build a $100M revenue business in 3 years? That was the question my coaching client Larry asked me with a straight face. Now, before you dismiss his question, you need to know that he just exited his previous startup a few months earlier. So I knew he had the chops. What a great question I thought ... ... so I took some time to really reflect on all the things I’ve learned in scaling my own software

Okay. Due to popular demand, I’ve decided to finally tackle the billion dollar question. And while it’s not easy to have a conversation about startup equity without putting the faint of heart to sleep, it’s territory that simply can’t be overlooked. Because for any growth-oriented entrepreneur entertaining the idea of handing out equity in their company, the math absolutely matters… And one small misstep can be the difference between accelerated growth or the speedpass to startup hell.