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:
1️⃣ 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.
2️⃣ 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.
3️⃣ 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
