Practical Founders Podcast

#47: How to Win Big When Selling Your SaaS Company for Under $50 million – Chris Kern

Chris Kern is an expert independent M&A advisor who has helped over 150 growing tech companies get financing, obtain investment, or sell their companies. He is Managing Director of Windstream Partners where he advises smaller SaaS and tech business owners in selling their companies for successful exits between $10M-$50M.

Chris got his start on Wall Street working on large finance and acquisition deals, but he quickly shifted gears 20 years ago, moved to Phoenix, and started working only with small software companies with growing SaaS, software, and technology businesses. I have known Chris for over 15 years.

In this interview with an active M&A professional who helps many practical SaaS founders sell their companies every year. I ask Chris the most common questions I hear from practical founders who are thinking about selling their companies someday.

Best quote from Chris:

“There are a thousand times more companies getting acquired for less than $50 million than all of those that sell for billion-dollar valuations. You just don’t hear about these deals because they are smaller and often have confidentiality agreements in place.

“With most of the buyers I deal with, you can successfully sell a software company when you start to reach as little as $500K to $1M in revenue. SaaS is still a very hot market in 2023. There’s a lot of demand and there are a lot of buyers out there.”

In this episode, Chris explains:

  • What’s happening right now in mergers & acquisitions of software, SaaS, and fintech companies that sell for $10M to $50M?
  • What are common valuations ranges for software startups and small companies with revenues between $500K and $5M in ARR?
  • What are the factors that affect valuation one way or the other?
  • Can you really sell a startup for a multiple of revenues when it’s still small?
  • Who is buying these smaller software companies and why are they buying them?
  • What is the general process of selling your company?
  • What should they be thinking about before they try to sell to maximize their outcome?
  • Is it better to have outside funding or to have bootstrapped when selling your company?


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Greg Head recorded this on episode on May 26, 2023 for the Practical Founders Podcast see all of the episodes.

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