Episode Details
Back to EpisodesWhy He'd Rather Hold 6 Businesses for 40 Years Than Flip Them
Description
Ryan spent 30 years in corporate America running businesses for other people. Then he got fired twice — never for performance, always for politics. He decided to never build for someone else again.
He co-founded North Park Group with his partner Greg Topol and built a holding company designed around one rule: never exit. Since 2022, he's bought 6 businesses in manufacturing and industrial distribution. He plans to own them until he's 85.
❌ No 5-year flip
❌ No PE-style fund timeline
❌ No 7-year wait for investors to see a return
His investors got their first distribution checks in 2022 — the same year he closed his first deal. He pays them twice a year. Today, 8 out of 10 people he pitches say yes.
In this episode, Ryan breaks down why he'd rather hold a business for 40 years than flip it every 5, how he wins deals without being the highest bidder, and why his year-one operating playbook at every company he buys is "don't fuck it up."
◼️ Why holding for 40 years can make you just as much money — if not more — than flipping every 5
◼️ The "distributions as proof points" model that converts 8 out of 10 investors
◼️ How he wins deals without being the highest bidder (one was 10% below the top offer)
◼️ The pre-LOI diligence inversion that lets him walk away before lawyers get involved
◼️ The $250K he lost on the one deal that broke — and what it taught him
◼️ The SBA-stacked operator model he uses to scale past his personal $5M lending cap
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