Why He'd Rather Hold 6 Businesses for 40 Years Than Flip Them

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 returnHis 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 capSubscribe to the SMB Deal Hunter newsletter (200,000+ subscribers): https://join.smbdealhunter.xyz/Want help buying a business?Learn about SMB Deal Hunter Pro: https://pro.smbdealhunter.xyz/Follow Helen:Twitter: https://x.com/HelenGuo_LinkedIn: https://www.linkedin.com/in/helen-guo-06674523/