HeyJaredThe Cheat Code & Friends
Serial entrepreneurs and operators Justin Gray, Josh Wagner & Sean Kester combine decades of B2B and GTM expertise with unwavering honesty to unpack the latest news (fake or otherwise) on The Cheat Code & Friends Podcast.
- Indexed episodes, last 90 days
- 7
- Latest publication
- Sep 25, 2026
- Audience
- Checking…
- Earliest in this view
- Jul 3, 2026
Latest episodes
Taste, Judgment and Scale - Season 5: Episode # 98 (opens the original)
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AI can have all the right data and context. That doesn't mean it knows what good looks like. What's missing is taste. Jason Vargas, Co-Founder & Chief Partner Officer at RevShoppe, describes it as the judgment that comes from experience: knowing what good looks like, recognizing when a message will resonate, and being willing to challenge an AI-generated answer instead of accepting it at face value. As companies build AI deeper into their go-to-market motions, Jason believes capturing that judgm
Distress, Discipline and Gasoline - Season 5: Episode # 97 (opens the original)
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Not every great company is a venture company. And not every great venture investment looks like the kind of deal everyone else is chasing. Brad Kotansky, Venture Partner at Copper Sky Capital, has built an investing philosophy around looking where the market isn't. With venture dollars increasingly concentrated among a handful of companies and fewer startups making it from Series A to Series B, Brad sees opportunity in places that don't always fit the traditional VC mold. That includes recapital
Intelligence, Hierarchies and Humans - Season 5: Episode # 96 (opens the original)
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AI is giving individual employees more leverage than ever. But Geoff McQueen, Founder and CEO of Ascendius, believes the bigger opportunity comes when companies stop treating AI as a collection of personal productivity tools and start thinking about it as intelligence that sits at the center of the organization. In this episode, Geoff joins Josh and Sean to explore what happens when AI has visibility across the systems, workflows, and digital signals that already run a business. They discuss why
Leadership, Research and Curiosity - Season 5: Episode # 95 (opens the original)
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Lauren Goldstein, long-time Go-to-Market Advisor and Co-Founder & Board Chair of Women in Revenue, set out to understand what's actually getting in the way of growth. After 53 conversations in 46 days with CEOs, investors, operators, and GTM leaders, the answers were surprisingly familiar: leadership, alignment, and a return to fundamentals. In this episode, Lauren joins Justin, Josh, and Sean to share what she's learning from her listening tour. They discuss why leadership becomes even more imp
Founder Curiosity, Growth and Valuation - Season 5: Episode # 94 (opens the original)
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AI has created one of the biggest shifts venture capital has seen in decades. New companies are reaching unprecedented growth rates, valuations are climbing, and founders have more ways than ever to build software. But according to Jay Po, Co-Founder and Managing Partner at Stage 2 Capital, the fundamentals of building a great business haven't changed nearly as much as people think. In this episode, Jay joins Justin and Josh to discuss how AI is changing venture investing without changing what u
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