Matt Watson was a two-time software company with two successful exits before he was 40 years old. He started his first company, VinSolutions, in his basement in Kansas City in 2006. VinSolutions started by helping auto dealers upload photos of their cars to sell in the popular Autotrader catalog and website. Matt was the first developer and product visionary who lead a team that build their popular CRM and lead management system to help those dealers manage internet leads and sell cars faster.

Their revenue doubled every year as they grew to eventually serve thousands of auto dealers with their pioneering web-based software.VinSolutions didn’t raise any venture capital or private equity investment as they grew to over 300 employees. In 2011, VinSolutions was acquired by Autotrader.com itself for a reported $150 million. 

Matt started Stackify in 2012 as the CEO funding the startup with his own money. Stackify is a tool for software developers using cloud platforms to manage and optimize application performance, a problem Matt had experienced at VinSolutions. Stackify grew slowly and struggled at first before it grew steadily. Stackify was acquired by Netreo in 2021. 

In this episode, Matt explains:

• How they started by taking photos of cars for auto dealers to sell those cars online, then bootstrapped a CRM software product to help dealers manage internet leads
• What it was like to be the CTO of a pioneer in web-based software with a recurring revenue business model back in 2008 when the auto industry was in a massive recession
• The benefits and drawbacks of growing a large vertical software company in Kansas City
• Why they tried to raise capital but started the process to sell the company instead
• Why Matt started a new company called Stackify as the CEO with a different customer focus, technology stack, and different sales model than his previous company
• Why did he self-funded Stackify and then raised venture debt as they grew, but didn’t raise big VC funding
• What it is like to be a two-time founder of software companies with successful exits before he was 40 years old

Find out more at practicalfounders.com.