Mike's Note — It is easier to change your preferred airline than it is your cap table
Seth Godin wrote “beware of experience asymmetry.” Reading his post, I thought about the time I got my first mortgage. I remember thinking, Am I getting a good rate? How much house should I buy versus how much house can I buy? It was stressful. I felt vulnerable. The internet and publicly available data helped me call around and shop rates. (I still would have paid handsome money for a local guide.)
Seth calls out venture capital in his post. This is an important place to get a local guide. In my opinion, the best local guide is another venture firm. This may sound counterintuitive, let me explain. If you’re looking to make a deal, having more than one venture firm in the mix will help you get a truer understanding of your market value and secure the fairest terms.
If you have more than one venture firm looking at your business, congrats. You are in rare air. Most are lucky to even get one interested. In those less-competitive cases, it’s still important to find a local guide. It could be a fellow founder, angel investor, trusted advisor, or a blog post from 2012.
Regardless of your path, always surround yourself with local guides for the various stages of your business. When fundraising, run a process with multiple firms and always do your homework on potential investors. Call up the companies in their portfolio that weren’t home runs. You will learn a lot.
It is hard to turn down money but sometimes you might want to because it is much easier to change your preferred airline than it is your cap table.
