Codie Sanchez spent 15 years in traditional finance — asset management, private equity, venture capital, running a division of First Trust to a billion dollars in AUM across Latin America — before deciding she would rather own businesses than advise on them. She started with laundromats, used seller financing before anyone in banking was talking about it, and built a vertical integration from laundromat to wash-and-fold to the software powering both. She sold when a PE firm offered an obscene multiple. She would have held forever.

Today Contrarian Thinking is the holding company and media engine behind two investment vehicles: Main Street Holding Company (profitable buyouts in home services and professional services, $3-50M revenue) and Contrarian Thinking Capital (a venture fund on its second vintage, ranked number one on AngelList for its 2022 class investing in vertical SMB SaaS). She does around 30 deals a year and sees deal flow at the volume of a top-tier venture firm.

In this episode, she breaks down the full model: how the media business drives negative-cost deal flow and is now beating Goldman and KKR for talent, the five-bucket hire-in matrix she uses for every acquisition and every hire, the five mistakes first-time buyers make in the first 100 days, and why she thinks audience is the fourth type of leverage that Naval forgot to name. She also gives a step-by-step answer to how she would buy a cashflowing business in 90 days starting from zero — the Venmo method included.

Takeaways:

Media as infrastructure isn't a brand play — it costs millions per year to run and functions as a deal sourcing engine, a talent magnet, and a trust shortcut with sellers before the first call

The hire-in matrix is a five-bucket scoring framework Codie uses identically for acquisitions and new hires: known talent, experienced talent, sector and scale fit, problem style, and role explicitly — everything gets scored before the meeting, not after

The Venmo method: stack rank your own expenses, remove anything too large to buy, and approach the owner of whatever's left — it's how Codie bought four businesses early on

Working capital is the most underestimated cost in small business acquisitions: it's how otherwise good deals die in the first 90 days

50/50 partnerships are where dreams go to die — every deal needs one person in charge and defined buyout rights

The long-term vision is to double the US small business acquisition rate and cut the 90% failure rate down toward the franchise industry average of 18-20%

Chapters:

00:00 — From sovereign wealth funds to laundromats: why Codie left traditional finance and what the first deals actually looked like

06:07 — The two vehicles: how Contrarian Thinking Capital (venture, SMB tech) and Main Street Holding Company (profitable buyouts) fit together

16:11 — The advisory model: why she wanted to bring McKinsey-level services to businesses that can't afford McKinsey — and how 14,000 companies gave her the data to do it

22:38 — The hire-in matrix: Codie's five-bucket framework for scoring people and businesses, and how AI now runs it in real time during calls

28:21 — Why opaque markets are an advantage: the Venmo method, BizScout, and how she thinks about deal sourcing without public financials

33:31 — The FINRA-licensed finance exec posting about laundromats: the bet on audience as the fourth type of leverage, and why the biggest PE firms only came around a year ago

39:08 — What media actually delivers: deal flow at a16z volume, immediate seller trust, and talent that's beating Goldman and KKR

44:07 — The five mistakes first-time buyers make, the J-curve every buyer needs to model, and why learning the language of deal making matters even if you never buy a business