I Took the BIGGEST Risk of My Life—Here’s What Happened, w/Josh Bey

In this episode of RAW STORIES LIVE, we sit down with Josh Bey, VP of West & APJ at Obsidian Security, as he shares the gripping story of how he turned a seemingly unwinnable deal into a game-changing success.

Facing financial pressure & personal life challenges, Josh breaks down the emotional investment, strategic pivots, and relentless determination that ultimately secured a massive win. This episode dives deep into the importance of resilience, the power of champion-building, and the art of navigating high-stakes negotiations.

Key Topics Covered:

00:00 – Intro

02:19 – A Scrappy Patch & an Unproven Market

05:11 – The Deal No One Believed In

07:08 – The Pivotal Meeting

08:59 – The Missing ‘Why Now’

10:32 – Finding the Real Champion

11:38 – Everyone Gave Up, But I Had No Choice

13:29 – The Biggest Lesson in Deal Making

3 Biggest Lessons:

Emotional investment can blind you – A deal isn’t real until you align it with the customer’s true business drivers. Personal stakes don’t equal urgency for the buyer.

The “why now” follows the “why anything” – If your deal lacks a compelling reason for change, there is no urgency. Customers must see value beyond just your product.

The real champion is the one who benefits the most – Look beyond those who like your solution. The real decision-maker is the one who gains money, a promotion, or influence.

Thanks for listening! This episode was hosted by Simon Kouttis and Ollie Kuehne, founders of Hunters & Unicorns, and post-produced by the team at videoforce.pro If you enjoyed this episode, please drop a like/share and subscribe to our channel!

Episode’s Links:

Connect with Josh Bey – https://www.linkedin.com/in/joshuabey/

Learn more about Obsidian Security – https://www.obsidiansecurity.com/

Connect with Hunters & Unicorns:

Website: http://huntersandunicorns.com

Twitter: http://twitter.com/HuntersUn1corns

Instagram: http://instagram.com/huntersandunicorns

Blog: http://huntersandunicorns.com/blog

Notable Quotes: “If you don’t have a strong enough ‘why anything,’ you’ll never get a ‘why now.’” – Josh Bay “Customers don’t care about your fiscal year or personal stakes. They care about their business needs.” “Find the champion who has something to gain—more money, a promotion, or expanded control.”

#rawstorieslive #softwaresales #huntersandunicorns