If you're scaling your agency but still stuck in the center of everything — decisions, operations, delivery — it's costing you more than time. It’s capping your growth, draining your team, and blocking your ability to build something truly sellable.
In this episode, I’m joined by Jordan Calderon, two-time exit founder and President of StratDev, a top 100 U.S. digital marketing firm that’s generated over $150 million in tracked client revenue. He’s also the founder of My Virtual Desk and someone who’s turned down 11 acquisition offers because he knew he could scale further.
We talk about how to build systems that scale without you, create operational clarity, avoid burnout, and make your business not just profitable, but sellable. You’ll hear how Jordan thinks about AI, team retention, hiring and firing, and what it really takes to create sellable agency systems that unlock optionality and freedom at scale.
If you’ve ever asked, “How do I get out of the day-to-day?” this is the episode for you.
⏱ Chapter Breakdown
00:03 — Meet Jordan Calderon: Founder, Strategist, 2X Exit Leader
01:22 — From Econ Class Dropout to Serial Entrepreneur
05:44 — Building and Selling His First E-Com Business
07:56 — What Buyers Actually Want in a Sellable Agency
11:07 — Learning Marketing by Doing (and YouTube)
13:20 — Turning Down 11 Acquisition Offers (and Why)
16:10 — Hard Lessons: Hiring Slow, Firing Fast
18:05 — Building a Team That Performs (and Stays)
21:58 — Who StratDev Serves and Why
23:53 — The Daily Practice That Keeps Him Leveling Up
28:30 — AI Integration and What Agencies Must Prepare For
31:15 — The Future Agency Model: Execution vs. Operator
📚 Books Mentioned
To learn more about Jordan’s work, connect with him at jordancalderon.me — where you’ll find his LinkedIn, Twitter, and business insights.
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