After the Close

Daniel Stetser
  • 0.0 (0)
  • Entrepreneurship

The best lessons in dealmaking never leave the room. After the Close changes that. Each episode unpacks a real lower middle market transaction — the mechanics, the mistakes, and the moments that made or killed the deal. Founders who've exited. Acquirers who've closed. Searchers who took the leap. And the deal professionals who got it across the finish line. One deal. One lesson. No fluff. Hosted by Dan, an entrepreneur and student of the deal who's obsessed with how small businesses are built, bought, and sold. New episodes weekly.

Episodes

  1. "I Regret Selling My Startup" — Boris Berenberg on the Atlas Authority Exit

    May 31

    "I Regret Selling My Startup" — Boris Berenberg on the Atlas Authority Exit

    What happens when a founder runs his own sale process, gets the deal done, and then writes a viral blog post titled "I Regret Selling My Startup"? Boris Berenberg spent six and a half years building Atlas Authority into one of the top Atlassian partner businesses in the world. Tens of millions in lifetime revenue, high single-digit millions in ARR, 10,000+ customers, fully bootstrapped. In 2022, he sold to a private equity rollup. The check cleared. The regret showed up shortly after. This conversation is a postmortem on a deal that closed but didn't deliver. Boris is candid about the bidding process he ran among friendly competitors, why he now believes a real advisor would have produced a dramatically different outcome, and how selling inside your own ecosystem can cause you to leave money on the table. The deeper story is about what the sale revealed. Boris talks through a values exercise he completed after closing, the gap between wealth and cash flow, and why most exited founders he knows did not actually retire. He also gets tactical on what he wishes he had figured out years before going to market, including tax structure, seller notes, and how to use AI to pressure test a deal thesis before you ever sign an LOI. For any owner thinking about an exit, this is the conversation worth hearing before you sign anything. In this episode: The annual "birthday bidding process" Boris ran on himself for yearsWhy selling to buyers who know your space too well can backfireWealth versus cash flow, and which one most founders actually wantThe post-close values exercise that reframed the whole experienceWhat Boris would have negotiated differently on transition and structureThe right way to use AI when you are preparing to sell Guest: Boris Berenberg, founder of Atlas Authority (exited 2022), now building z0.ai Host: Dan Stetser New episodes every other week ataftertheclosepodcast.com

    33 min
  2. From 3x to 5x Earnout - Jeff Archibald on the Paper Leaf Exit

    May 8

    From 3x to 5x Earnout - Jeff Archibald on the Paper Leaf Exit

    Jeff Archibald built Paper Leaf from a two-person design shop into a 30-person custom software firm doing $4M in revenue. Then he sold it, but not before a failed deal nearly cost him everything. In this episode, Jeff walks through both deals: the PE buyer who dragged him through five months of due diligence, ran up $50K in professional fees, and then rewrote the terms on closing day. He also breaks down the strategic acquirer who ultimately bought the business with a structure that worked for both sides. You'll hear how Jeff negotiated his initial offer of 3x EBITDA up to nearly 5x through a creative earnout, why the buyer's willingness to funnel work into Paper Leaf made the performance targets actually achievable, and what the three-year transition period looked like from the inside. Whether you're years away from a sale or actively fielding interest, this conversation covers the real mechanics of how deals get structured, how they fall apart, and what separates a good outcome from a bad one.

    49 min
  • 2 Episodes

About

The best lessons in dealmaking never leave the room. After the Close changes that. Each episode unpacks a real lower middle market transaction — the mechanics, the mistakes, and the moments that made or killed the deal. Founders who've exited. Acquirers who've closed. Searchers who took the leap. And the deal professionals who got it across the finish line. One deal. One lesson. No fluff. Hosted by Dan, an entrepreneur and student of the deal who's obsessed with how small businesses are built, bought, and sold. New episodes weekly.

Information

  • Creator
    Daniel Stetser
  • Years Active
    2K
  • Episodes
    2
  • Rating
    Clean
  • Copyright
    © 2026 Daniel Stetser