DiscoverMastering Tech GrowthExit Ready vs Exit Trapped: Why Most Founders Get This Wrong
Exit Ready vs Exit Trapped: Why Most Founders Get This Wrong

Exit Ready vs Exit Trapped: Why Most Founders Get This Wrong

Update: 2025-09-10
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Selling your business is where most founders lose their leverage, not win it. This episode shows how to turn your tech company or agency into a sellable asset years before exit so buyers pay up instead of retrading you down at the last minute.Perfect listen if you’re a bootstrapped or lightly funded tech / agency founder who wants real exit options, not burnout, golden handcuffs and a surprise haircut on valuation.To unpack this, I sat down with Jordan Calderon, a two-time exited founder and president of StratDev, one of the top 100 marketing firms in the US. He’s built and sold multiple bootstrapped companies, lived through a painful retrade on his first exit, then engineered a multi-offer, over-ask sale on his second.

https://www.linkedin.com/in/jordan-a-calderon/In this episode:

  • The simple “hit-by-a-bus” test Jordan uses to spot founder dependency early and remove it so you don’t get stuck in multi-year earn-out handcuffs.
  • How the M&A process actually works (CIM, LOI, due diligence, retrades) and the brutal $50m → $1.2m horror story that proves why exit readiness is a 1–3 year game, not a 3-month sprint.
  • The three levers buyers care about most: sustainable growth curves, a business that runs without you, and SOPs that can add roughly +1x EBITDA to your valuation almost out of thin air.
  • A dead-simple framework for building SOPs in Google Docs (including the “Starbucks stranger” test) so any new hire—or buyer—can follow your processes like a recipe.
  • How Jordan uses offshore and nearshore teams to charge “US prices, global costs” while improving delivery quality and margins.
  • The pricing and negotiation moves he used to go from being retraded on his first deal to running a competitive process with 11 LOIs, anchoring high, and protecting terms inside the LOI.

Get the links, notes and resources from this episode at masteringtechgrowth.com

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Exit Ready vs Exit Trapped: Why Most Founders Get This Wrong

Exit Ready vs Exit Trapped: Why Most Founders Get This Wrong

Mike Sirius