Episode 100: Inside the Deal with Seth Freedman

Apr 27, 2026

In this episode of the Tech M&A Podcast, we chat with Seth Freedman, founder of Intelligent Observation, to explore the realities of building, scaling, and ultimately exiting a venture-backed software business. Over a six-year period, Seth grew the company from startup to acquisition, navigating the pressures of institutional capital and the strategic decisions that come with sustained growth.

Seth shares how a timely outreach from Corum initiated his M&A journey and walks through the board-level decision between raising additional capital versus pursuing a sale. He offers candid insight into the emotional transition founders experience post-exit, the demands of running a company while selling it, and how a strategic “hiatus” period allowed Intelligent Observation to strengthen key metrics—particularly churn—before returning to market with a stronger position and a clearer value story.

Takeaways

• Exits are a strategic fork in the road: For VC-backed companies, selling is often weighed directly against raising more capital and scaling further.
• Timing and positioning matter: Going to market before the business is fully prepared can limit outcomes—and knowing when to pause can create leverage.
• A hiatus can add real value: Stepping back to address how churn and sustaining growth can significantly improve buyer confidence and valuation.
• Selling while operating is demanding: Founders must balance diligence, negotiations, and day-to-day leadership at the same time.
• Expect the personal transition: The emotional shift after an exit often begins once the deal is done, not before.

Timestamps

00:00 – Pre-roll and setup: audio, video, and resetting the take
01:09 – Introducing Seth Freedman and Intelligent Observation
02:04 – How Seth first learned about Corum and why the timing mattered
02:39 – The VC-backed fork in the road: raise more capital or pursue M&A
03:11 – Life after the sale: the founder transition after the excitement fades
03:52 – Lessons learned building and exiting a startup
04:39 – Advice for CEOs selling their company
05:21 – What’s next: taking time before the next challenge
05:53 – The first attempt to sell and why it didn’t close
06:52 – Using a one-year hiatus to fix churn, strengthen metrics, and return to market