Are you approaching your business with intention—or relying on hope and momentum to carry you forward?

In business, much like in poker, long-term success has very little to do with luck. It’s built through discipline, emotional control, and an honest understanding of risk. The strongest players don’t force outcomes—they know when to lean in, when to step back, and how to stay grounded through volatility. Community, trust, and resilience matter just as much as technical skill, especially when uncertainty is part of the game.

In this episode, Oliver Kotelnikov sits down with longtime friend and poker community leader Stevie Ray Helton to explore the striking parallels between poker and entrepreneurship.

Drawing from decades of running Seattle’s underground Monday Night Poker League, Stevie shares lessons on bankroll management, ego, adaptability, diversity at the table, and why mindset and relationships often determine outcomes more than raw talent. Together, they connect these insights to business brokerage, leadership, and building sustainable success.

Listen in and reflect on how you’re managing risk, relationships, and resilience in your own journey.

Guest Links:
Email: stevenhelton@outlook.com

Connect with Oliver:
Email: oliver@ibainc.com
LinkedIn: linkedin.com/in/oliverkotelnikov
YouTube: https://www.youtube.com/@NextVentureAlliance
Instagram: instagram.com/nextventurealliance

• (00:00:00) - Next Venture Alliance
• (00:01:50) - Poker Legends: The Boom
• (00:05:47) - The Diversity of Poker
• (00:08:25) - Was the tournament poker system outdated?
• (00:14:36) - Poker Star on Running a Business
• (00:16:14) - Poker Player on The Cast of Characters
• (00:21:38) - Poker on a Monday Night
• (00:27:27) - Poker Stars: How to Manage a Bankroll
• (00:34:06) - "Crazy Odds"
• (00:34:31) - Poker Lesson: Game Theory
• (00:40:15) - Poker Star Mike McDermott on His Mistake
• (00:46:09) - Poker Players On How To Buy Bitcoin
• (00:49:42) - The World of Poker
• (00:55:39) - Poker's Nostalgia Will Always Be There
• (01:03:26) - Poker Stars on the Evolution of the Game
• (01:08:25) - Top Poker Stars on the
• (01:14:29) - Flipping a Straight in Omaha
• (01:18:12) - Poker Legends on Monday Night Events
• (01:21:47) - Raised Events
• (01:28:25) - Pro Poker Stars: Giving Back Through Events
• (01:33:56) - What is a Charity Poker Tournament?
• (01:35:45) - How to Get Out of Real Estate Hacks
• (01:39:20) - Real Estate: Demand for Homes, Real Estate Prices
• (01:45:52) - Chat GPT and Artificial Intelligence
• (01:51:59) - Phil Keating on Daniel Negrano's
• (01:57:43) - Talking Up a Good Habit
• (02:01:55) - Americans on the Convenience Crisis
• (02:03:54) - Stevie Jackson on His Next Step
• (02:06:41) - Poker on My Face With Nicole
• (02:12:12) - The Kangaroo and Nicole
• (02:14:57) - Lars Had A Bar Near Ballard
• (02:18:29) - Next Venture Alliance: Exploring the Unknown