Skip to content
← All issues
November 9, 2026

Three Friends, $5,000 Each, Nine Years in the Black

Rounders to Founders is a free community for poker players building startups. Join free and post your build →

🃏 R2F Spotlight

A poker player who built a business.

Doug Polk, smiling, black and white portrait

Doug Polk and two friends put $5,000 each into a poker school. After month two, it never lost money again.

Doug won three WSOP bracelets, including the 2017 $111,111 One Drop High Roller for $3,686,865. In 2015 he and two friends started Upswing Poker, a training site. They each wrote a $5,000 check, and in month two each had to add another $5,000.

That was the last unprofitable month. The business made money every month for more than nine years, and Doug built the audience himself, one YouTube video at a time. In August 2025 they sold it to ClubWPT Gold for an undisclosed amount.

"It was a great company, and I felt like we took it as far as we could."

Steal this: split the seats by skill. One founder per job, and say out loud who owns what.

Read Doug's story

Know a poker player who built something? Tell us who in the discussion thread.

— Art

PS: New here? Rounders to Founders is a community for poker players building businesses. Post what you're building and get honest feedback from people who've been there. Post yours, free.

Building something? Put it next to Art's.

Free account, two minutes. Your build gets its own page and a running log the rest of us can follow, even if it's just an idea and a domain.

Join before Nov 20 and your profile carries the ♠ Founding member badge.

Join free and post your build
Get the next one

Two emails a week. Unsubscribe in one click.

Three Friends, $5,000 Each, Nine Years in the Black | R2F Newsletter