I started my first company with Cashman Andrus in 2001. It was a bet that people would play video games on their cell phones. Lots of people (including my mom) thought it was a stupid idea, but it was just really early. Luckily, we bootstrapped the company so when we sold to CNET in 2004, everyone made money.
Cashman and I started another company called Yesware. I served there as CEO from $0 to $12m ARR. We served great customers and raised $50m from incredible investors like Brad Feld and Neeraj Agrawal, but after eight years I hit a wall. Luckily, I met Joel Stevenson and he agreed to lead the company from 2018 on. We sold Yesware to Vendasta in 2022.
My third startup was called BodesWell. Bernie Bernstein and I started it in early 2019. Our mission was to provide the benefits of financial planning to everyone by partnering with the largest financial services companies in the world. Our first launch was with American Express. Here is the Techcrunch post about that. In June of 2022, we sold BodesWell to American Express and joined up with that incredible team to continue our mission.
The common thread across all of these startups has been selling startup products to very large companies. At WGR (the mobile games startup), our first five deals were to Sega, JAMDAT (now part of EA), Sprint, Nokia and Verizon. At Yesware, our first five deals were with Groupon, Salesforce.com, Hubspot, Box and Yelp. We only had two customers at BodesWell, and one was secret, but the pattern is clear.
Previously, I wrote up my approach to opportunity assessment and financial modeling for nascent startups. If you are thinking of building a business and want to figure out how much money you need to raise, here’s a spreadsheet for you:
Free Startup Business Model Template
A colleague wrote in asking how to set up a consulting business in 2023, so I created this quick guide:
How to Set up a Consulting Business
As a way of communicating some of the approaches we took to software development at BodesWell, I wrote up this guide. Some of it is mundane how-to. Some of it is meaningful.