In this episode of Founder2Founder, Aaron Spivak sits down with Richart Ruddie, serial entrepreneur, art collector, and founder of CaptainCompliance.com. Richart has built and exited multiple ventures across marketing, tech, and real estate, including one of the largest ORM agencies in the U.S.

From hustling calling cards as a teen, to selling a business at 24, Richart breaks down how he built a career by spotting overlooked opportunities and outworking everyone in the room. He shares the hard lessons behind scaling, selling, hiring, and why ignoring compliance could cost your company everything.

Chapters:

02:26 – Growing Up in Baltimore & Entrepreneurial Roots
 03:35 – First Job Punching Calling Cards at Age 12
 05:39 – Why “$10M” Isn’t the End Goal
 07:19 – How College Shaped His Hustle
 09:41 – Graduating Debt-Free Through Work Ethic
 11:01 – Grit vs. Moats: Why Outworking Wins
 12:06 – Giving First: A Foundational Principle
 14:16 – Books That Changed His Life
 19:44 – The First Business Exit: Dumpster Rentals at 24
 21:13 – Breaking Into SEO & Internet Arbitrage
 23:32 – How He Scaled a Boring Business Fast
 25:39 – Selling Leads in a Non-Tech Industry
 26:46 – Exit Strategy: When to Sell and Why
 28:06 – Building Profile Defenders From a Craigslist Ad
 29:25 – Scaling to $90K/Month in Under a Year
 31:00 – Private Equity Exit in 2023: How It Went Down
 32:11 – Systems vs. Team: What Buyers Really Look For
 33:49 – Why He Left 7x Revenue Growth on the Table
 37:48 – The Compliance Opportunity Most Founders Miss
 40:07 – From Removal Services to Privacy Software
 41:54 – Understanding Regulatory Risk in Scaling
 44:31 – Real Lawsuits: The Wake-Up Call for Founders
 46:55 – How $500/Month Could Have Saved a $5M Lawsuit
 49:08 – Hiring Strategy: Culture, Grit & Technical Testing
 50:46 – The One Interview Question That Says It All
 53:44 – Building & Exiting in a Hyper-Competitive Market
 55:19 – Advice to His 15-Year-Old Self
 58:08 – Why Going Deep, Not Wide, Builds Real Advantage

Guest Links:
Website: https://captaincompliance.com/
LinkedIn: https://www.linkedin.com/in/richartruddie/

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