What Is Personal FinanceDave Portnoy founded Barstool Sports in 2003 as a free print publication distributed around Boston, covering sports betting and local commentary. Over the following two decades, it grew into an online media company covering sports and pop culture with a large, loyal audience. His estimated net worth, reported by outlets like Forbes in the hundreds of millions, comes primarily from his ownership stake in that company, built from nothing rather than inherited or invested into from outside at the start.
From a local paper to a media company with investors
Portnoy sold a majority stake in Barstool Sports to The Chernin Group in 2016, retaining a role and reported ownership share while bringing in outside capital and infrastructure to grow further. In 2020, Penn National Gaming, later renamed Penn Entertainment, invested in Barstool for a reported stake valued around 36%, a deal outlets described as valuing the company in the hundreds of millions, later increasing its ownership. In 2023, reports said Penn sold Barstool back to Portnoy for a nominal price while keeping certain licensing rights tied to sports betting, as Penn shifted its sportsbook branding toward a different partner.
Continuing to build after the exit
Rather than stopping after the Penn arrangement ended, Portnoy kept building new, audience-driven ventures, including a pizza review series that grew into its own following and brand deals separate from Barstool itself. The pattern across two decades stays consistent: build an audience around content, then find ways to monetize and grow the business built on top of that audience, repeatedly rather than once.
The transferable lesson
Few people found a media company that draws a nine-figure investment, but the underlying sequence transfers to a smaller scale: start something from almost nothing, keep at it long enough to build a real audience or customer base, and only then look for outside capital or a buyer once there's something with real value to negotiate over. Ownership retained through that whole sequence pays differently than a salary earned working for someone else's version of the same business, because ownership captures the value created along the way instead of only a wage for the work. Readers curious how outside investors evaluate and buy into growing companies might find angel investing vs. venture capital vs. private equity a useful next read.
To see how a business ownership stake fits into a full net worth calculation, see what net worth means and how to calculate yours.
Public net worth figures for Dave Portnoy are estimates from outlets like Forbes. They vary by source and change as new business and investment figures get reported. Nothing in this article is financial advice about any specific investment or business.