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From Broke to Big Time Exit in Just 2 Years

August 27, 2021 |  

About this episode


In 2017, Justin Adams co-founded Digitize.AI to help hospitals get paid. They used artificial intelligence to get medical treatments pre-approved by insurance companies ensuring their patients could pay their medical bills.

The business was hungry for cash, and Adams and his wife put everything their young family had into the idea. At one point, Adams was so short of money that when their clothes dryer broke, the Adams family started hanging their laundry because they couldn’t afford the repair.

By 2019, things had started to turn around for Adams. Digitize had signed up their first few hospitals. However, the business was still thirsty for cash, and their competitors were raising eight and nine-figure investment rounds. Adams started partnership conversations with other software companies in the medical industry. He was pleasantly surprised to learn his young company may be worth 15-25 times revenue.

Adams decided to sell, and in this episode, you’ll learn:

  • How to increase the likelihood-hood your business idea will be a success.
  • The hidden downside of retaining at least 50% of your company when you sell equity.
  • How service businesses are valued compared to software companies.
  • How to ensure you protect your intellectual property if you’re considering turning your consulting business into a product company.
  • Why limiting the diligence period is a crucial deal point you need to negotiate in a Letter of Intent (LOI).
  • The ultimate BATNA that maximizes your negotiating leverage.


Check out our article on Biggest Mistake You Can Make When Turning A Service Into A Product.

Check out our full M&A Glossary

About Our Guest

Justin has spent his entire career helping transform organizations through technology and innovation, from Fortune 500 firms to the United States Intelligence Community.

Previously, Justin co-founded and led Digitize.AI as CEO and Chairman of the Board through the acquisition by Waystar and was a member of the Executive Leadership Team. Justin was a partner at a management consulting firm where he led the A.I. practice. Justin also helped start and built PwC’s Automation Center of Excellence.

Justin began his career in the Intelligence Community, where he started a task force that used novel technology to combine data analytics and operational responsibilities. He also sat on a board that advised a venture capital firm on promising new technologies. He received numerous awards from the government for his efforts.

Justin holds an MBA from the University of Chicago Booth School of Business and a BA in Economics with honors from Wheaton College.


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