$50 Million Was His Number—Here’s How Josh Payne Got There

Unlike most tech founders, Josh Payne never dreamed of a billion-dollar valuation. 

His goal was simpler—and harder. He wanted his equity stake to be worth $50 million. 

To get there, he skipped the usual playbook. No blitzscaling. No VC treadmill. He raised a small seed round, built a profitable company, and avoided dilution. By the time he sold StackCommerce, Payne still owned 75%—and hit his number. 

In this episode of Built to Sell Radio, you’ll discover how to: 

• Grow without giving away your company 

• Align your capital strategy with your exit goal 

• Use profitability as leverage at the deal table 

• Time your exit to take advantage of market cycles 

• Avoid chasing size at the expense of freedom 

• Rebuild your purpose after the money clears 

Josh didn’t want headlines. He wanted freedom. And he built StackCommerce to deliver it. 

Show Notes & Links

StackCommerce

OpenSky Ventures

Connect with Josh on LinkedIn

Definitions

LTV:CAC Definition: The Lifetime Value to Customer Acquisition Cost ratio compares the value of a customer over time to the cost of acquiring that customer. It’s crucial for evaluating the long-term value of a customer and the profitability of customer acquisition strategies.

Due-Diligence: This is a comprehensive appraisal of a business or investment undertaken before a merger, acquisition, or investment. It seeks to validate the information provided and uncover any potential risks or liabilities.

Earn-out: This is a financing arrangement for the purchase of a business, where the seller must meet certain performance goals before receiving the full purchase price. It reduces the buyer’s risk and aligns the interests of both parties post-acquisition.

About Our Guest

Josh Payne

Josh Payne is a seasoned entrepreneur, investor, and startup advisor best known for founding StackCommerce, the leading native commerce platform that transforms the way publishers monetize digital content. Under his leadership, the company grew from a curated flash‑sale site (StackSocial) to powering white‑labeled commerce for over 750 major publishers, reaching 500 million+ monthly visitors across the web—including CNN, Mashable, Hearst, and Yahoo!

With just $5,000 in his bank account in 2011, Payne built StackCommerce to over $80 million in annual gross revenue by 2020, maintaining profitability along the way. In late 2020, he sold a majority stake to TPG’s Integrated Media Company, securing StackCommerce’s long-term trajectory