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

Описание: 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 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.

In our conversation, Jordan shares:
→ 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.

Where to find Jordan Calderon:
→ Website: https://www.jordancalderon.me/
→ LinkedIn:   / jordan-a-calderon  

Where to find Mike Sirius:
→ Website: https://www.mikesirius.com
→ LinkedIn:   / msirius  

In this episode, we cover:
00:00 Building a Sellable Business
13:12 The Importance of Exit Readiness
21:08 Navigating Mergers and Acquisitions
30:05 The Emotional Toll of Selling a Business
33:22 Lessons Learned from Business Failures
35:36 Risk and Resilience in Entrepreneurship
38:20 The Importance of Standard Operating Procedures (SOPs)
45:14 Building a Business Beyond Founder Dependency
52:48 Understanding Business Valuation and Buyer Psychology
01:01:56 Negotiation Dynamics in Business Transactions
01:04:13 Preparing Your Business for Exit
01:06:37 Leveraging Remote Talent for Business Growth
01:11:08 Understanding Business Valuation Risks
01:13:23 Operational Systems and Due Diligence
01:16:12 Cultural Strength in Remote Teams
01:18:08 Founder Dependency and Business Sell-ability
01:20:24 Recognising Team Contributions in Business Success
01:21:17 Key Metrics for Business Valuation
01:22:50 Hiring Strategies for Scaling Businesses

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