In this episode, Ken Freire sits down with Tom Hart, founder of Hart Ops, to unpack why so many 7-figure agencies get stuck in the “financial black hole”—and what it actually takes to make profit possible. Tom shares his contrarian takes on experience, hiring, training, and why “automation basics” matter more than AI for most smaller agencies.

Resources Mentioned

• Hart Ops (website) — https://hartops.com/
• Tom Hart (LinkedIn) — https://www.linkedin.com/in/hartops
• The Bureau (formerly Bureau of Digital) — https://thebureau.community/
• Simple Numbers, Straight Talk, Big Profits! (Greg Crabtree) — https://gregcrabtree.net/books/simple-numbers-straight-talk-big-profits/

Timestamps

• 00:01 — Tom Hart’s background + what Hart Ops does for $1M–$5M agencies
• 01:54 — From English degree to web design to running a wedding business, then agency ops
• 03:11 — Turning an agency around: cutting salary cap, 13 months straight profit
• 06:46 — How Tom wins clients: referrals + The Bureau/EOS community + a 4-week program (40-page operating doc)
• 09:48 — The “simple numbers” Tom looks at: revenue vs margin, target 20% profit, and people cost red flags
• 12:10 — AI vs automations: why most smaller agencies should master basics first
• 17:13 — Common agency traps: overpaying talent while underbilling clients; align hourly costs with billing
• 19:41 — Training + coaching as retention strategy: grow people beyond their role
• 22:10 — Contrarian view: experience is overrated; hire hungry younger pros; document processes to remove the founder bottleneck
• 25:15 — Values + vision reset: “corporate therapy,” reclaiming the original mission, and EOS vision clarity
• 29:02 — Advice for the stuck founder: perspective from an outside operator who can tell the truth
• 32:23 — Fast Five: short-form podcasts + LinkedIn, marketing focus, industry shifts, and legacy book (maybe workplace poetry)
• 37:26 — Where to reach Tom: Hart Ops on web + LinkedIn