The Cheat Code & Friends

In Revenue Capital

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. Combined with a rotating guest list of founders, practitioners and investors, the no-nonsense forum gathers fortnightly, holding court to translate headlines into reality and discuss the impact for early-stage businesses. The Cheat Code is just that, the trusted folks we look to for advice and insight, and we hope to bring the same to you. Game over.

  1. 9h ago

    Leadership, Research and Curiosity - Season 5: Episode # 95

    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 important as companies experiment with AI, why organizations are still surprisingly misaligned around their ICP, and how leaders can give teams room to experiment without creating disconnected pockets of activity. The conversation also explores an emerging cost of AI adoption that doesn't get enough attention: burnout. Lauren explains why asking employees to transform how they work while continuing to deliver at the same pace can become an organizational constraint in itself, and why leaders need to balance efficiency with the human side of change. They also dig into the enduring value of relationships, mentorship, proximity to customers, and building a network long before you need something from it. Chapters 00:00 Introduction and episode overview 02:00 Lauren's recent activities and 'tour de interesting' 07:02 Key findings on business growth constraints 08:31 Leadership challenges in AI and go-to-market 11:51 Characteristics of effective leaders in tech 15:01 The importance of ICP and fundamentals 18:06 Building trust and proximity in sales 21:47 Managing organizational drift and operational debt 25:50 Supporting teams and preventing burnout 30:03 Leadership practices for change management 35:58 Women in Revenue and mentorship initiatives 43:58 Connecting with Lauren and closing remarks References in the Show: https://www.forrester.com/blogs/ai-is-accelerating-the-great-gtm-reset-for-partner-ecosystems/  https://www.forbes.com/councils/forbesbusinesscouncil/2026/06/05/the-all-or-nothing-trap-how-ai-fatigue-is-warping-executive-judgment/  Quote of the Show: “I was expecting to hear a lot of stumbling and starts and stops around AI, right? That was the obvious thing of how experimentation was either creating a lot of breakthroughs or experimentation was creating a lot of efficiencies. And there was definitely a little bit of that. But when people took a step back and really thought about it and provided the honest answer, it was not surprising: lack of leadership, right? Like that emerged as a really big one on a number of occasions.” - Lauren Goldstein Ways to Tune In: Spotify: https://open.spotify.com/show/5GpM8myxsUinc5bfLIbjJz?si=0af576adfb8e49f8 Apple Podcasts: https://podcasts.apple.com/us/podcast/the-cheat-code/id1692445190 Amazon Music: https://music.amazon.com/podcasts/cb0b3afa-063f-4f3b-96be-b98214c74912 YouTube: https://www.youtube.com/@CheatCodePodcast

  2. Jul 31

    Founder Curiosity, Growth and Valuation - Season 5: Episode # 94

    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 ultimately matters. He explains why customer obsession, repeatable growth, and retention continue to separate enduring companies from short-lived momentum, why investors are rethinking pricing models and valuation, and how founders should approach fundraising in a market filled with both opportunity and noise. Tune in for more on outcome-based pricing, forward-deployed engineers, customer success as a growth function, venture capital discipline, and why the next generation of market leaders will be defined less by AI itself than by how effectively they solve meaningful customer problems. Chapters 00:00 Introduction and guest background 02:17 Stage 2 Capital's investment thesis and history 05:30 Market evolution from 2018 to today 10:07 Impact of AI on venture and market opportunities 15:04 The role of curiosity and innovation in startups 20:42 Pricing models and outcome-based strategies in AI 25:46 Customer success, retention, and long-term value 30:09 Valuation approaches and market dynamics 36:09 The messiness and opportunities in early-stage investing 40:14 Valuation discipline and market noise 45:05 Future outlook and strategic positioning References in the Show: https://techcrunch.com/2026/03/20/ai-startups-are-eating-the-venture-industry-and-the-returns-so-far-are-good/  https://www.stage2.capital/  Quote of the Show: “One thing that I've been finding pretty interesting is how companies are being funded relative to their underlying fundamental performance from a revenue perspective and whatnot. Just being so obsessed with what is the customer's pain point, life cycle, use case priorities, criticality, because there's no amount of capital that can solve that for you. Right? Like there's no amount of capital that's gonna have this manufacturing plant not wanna change their behavior, but still find value in your product.” - Jay Po Ways to Tune In: Spotify: https://open.spotify.com/show/5GpM8myxsUinc5bfLIbjJz?si=0af576adfb8e49f8 Apple Podcasts: https://podcasts.apple.com/us/podcast/the-cheat-code/id1692445190 Amazon Music: https://music.amazon.com/podcasts/cb0b3afa-063f-4f3b-96be-b98214c74912 YouTube: https://www.youtube.com/@CheatCodePodcast

  3. Jul 17

    Priorities, Adoption and Misalignment - Season 5: Episode # 93

    In this episode, JT Bricker, CEO of Grazzy, shares what it takes to lead a growing company when every opportunity looks important and every decision carries long-term consequences. Drawing on decades of experience scaling organizations, JT explains why the best operators don't try to do everything. They build systems, align teams around a few critical priorities, and stay relentlessly focused on creating customer value. Together, JT and the hosts explore why customer adoption matters more than sales heroics, how leaders create alignment across growing organizations, and why operational discipline often becomes a bigger competitive advantage than strategy itself. Tune in to hear more about building the right culture, balancing long-term strategy with day-to-day execution, and why sustainable growth comes from helping customers succeed, not simply winning more deals. Chapters 02:36 JT Bricker's background and role at Grazzy 05:39 Prioritization in high-growth SaaS companies 09:08 Entering a business organically and intentionally 13:39 Assessing companies in a changing funding environment 17:27 The importance of focus and operational excellence 21:02 Triangulating customer value and growth 23:17 Pricing, packaging, and unit economics in SaaS 26:36 Building usage flywheels and scalable products 30:41 The shift to consumption-based models and sales strategies 34:20 Impact of AI on sales, customer success, and talent 43:56 Talent acquisition and strategic hiring in SaaS 48:24 Final thoughts on prioritization and growth strategies References in the Show: https://www.forbes.com/sites/larryenglish/2026/03/24/the-ai-era-is-changing-what-it-means-to-be-a-ceo/  https://inrevenue.com/insights/what-kills-saas-companies-between-1m-and-10m-arr/  Quote of the Show: “Good customer success, which means good customer relationships, does a good portion of the selling on the front end of the business. It doesn't mean that a salesperson doesn't have to sell the product, but the story that they can tell is, ‘hey, here's an operator, here's a customer that looks just like you, here's exactly what they're getting out of the platform.’ They're showing the real results through that.” - JT Bricker Ways to Tune In: Spotify: https://open.spotify.com/show/5GpM8myxsUinc5bfLIbjJz?si=0af576adfb8e49f8 Apple Podcasts: https://podcasts.apple.com/us/podcast/the-cheat-code/id1692445190 Amazon Music: https://music.amazon.com/podcasts/cb0b3afa-063f-4f3b-96be-b98214c74912 YouTube: https://www.youtube.com/@CheatCodePodcast

  4. Jul 3

    Priorities, Culture and Growth - Season 5: Episode # 92

    The hardest part of building a company isn't finding more opportunities. It's deciding which ones deserve your attention. In this episode, Grant Siders, founder and CEO of Helia, shares how founders can stay focused as companies grow, funding arrives, and priorities multiply. He explains why raising capital doesn't remove constraints, it changes them, and why great leaders learn to separate what's existential from what's simply distracting. The conversation explores prioritization, operating cadence, hiring, company culture, and the systems that help organizations stay aligned when plans inevitably change. Chapters 03:54 Grant Siders: Background and Helia's Mission 08:01 Understanding Healthcare Procurement Challenges 12:32 The Financial Implications of Medical Device Procurement 17:44 Prioritizing Focus and Decision-Making in Startups 21:41 Driving Enterprise Value in Healthcare Networks 24:00 Navigating Early Sales Cycles and Market Education 26:04 Data-Driven Decisions in Healthcare 27:55 Operational Cadence and Strategic Clarity 34:01 Building a Culture of Accountability 38:56 Adapting to Change and Future Growth References in the Show: https://startupgrowthhacking.substack.com/p/the-first-90-days-post-funding-where    https://hbr.org/2026/01/the-risks-of-prioritizing-short-term-revenue-over-customer-fit  Quote of the Show: “Early on, I thought prioritization was making a list, right? Like, I'm a list guy. I got one right here next to me. I make one every morning. Everything feels important, but it's not. I think over time I realized prioritization was about identifying the constraints, and what's a single thing today limiting the business right now? That's where I would shift my focus and then mobilize the team, the org, and the leadership around that.” - Grant Siders Ways to Tune In: Spotify: https://open.spotify.com/show/5GpM8myxsUinc5bfLIbjJz?si=0af576adfb8e49f8 Apple Podcasts: https://podcasts.apple.com/us/podcast/the-cheat-code/id1692445190 Amazon Music: https://music.amazon.com/podcasts/cb0b3afa-063f-4f3b-96be-b98214c74912 YouTube: https://www.youtube.com/@CheatCodePodcast

  5. Jun 5

    Customer Obsession, Trust and Modern Marketing - Season 5: Episode # 91

    Looking for insights on customer obsession, trust, and what modern marketing leaders should actually be focusing on? This episode has you covered. In this episode of the Cheat Code + Friends podcast, Matt Heinz shares why the best marketers are still solving many of the same problems they were solving twenty years ago. Despite the rise of AI, automation, and new go-to-market tools, he argues that customer understanding, trust, and buyer confidence remain the foundations of sustainable growth. Matt explains why too many companies get distracted by technology before deeply understanding the customers they're trying to serve. He discusses sales and marketing alignment, brand building, customer confidence, and why great marketing should help buyers make better decisions, not just generate more leads. Chapters 00:00 The Evolution of Tech Conferences 09:00 Navigating the Changing Landscape of Marketing 19:00 The Role of CMOs in Modern Marketing 22:04 Cultural Change in Marketing 24:34 Rethinking Marketing's Role 26:18 Trust and Marketing Leadership 28:54 The Evolution of Marketing Metrics 30:11 Challenges in Early-Stage Marketing 32:26 The Importance of Brand Credibility 34:54 Building Customer Confidence 39:20 The Comeback of Events 42:28 Creative Approaches to Events 47:10 Budgeting for Marketing Succes References in the Show: https://www.gartner.com/en/newsroom/press-releases/2026-02-23-gartner-survey-reveals-cmo-ai-blind-spot-as-65-percent-expect-role-disruption-yet-only-32-percent-say-significant-skill-changes-are-needed  https://www.forrester.com/blogs/predictions-2026-marketing-agencies-resign-their-agency/  Quote of the Show: “I see so many CMOs burn out just trying to do the right thing and just really challenged because you're not playing with a full deck. You're given this many cards and you're still expected to win.” - Matt Heinz Ways to Tune In: Spotify: https://open.spotify.com/show/5GpM8myxsUinc5bfLIbjJz?si=0af576adfb8e49f8 Apple Podcasts: https://podcasts.apple.com/us/podcast/the-cheat-code/id1692445190 Amazon Music: https://music.amazon.com/podcasts/cb0b3afa-063f-4f3b-96be-b98214c74912 YouTube: https://www.youtube.com/@CheatCodePodcast

  6. May 22

    Leadership, Burnout and Purpose - Season 5: Episode # 90

    A lot of leaders look successful right before they burn out. In this episode of the Cheat Code + Friends podcast, Jason Yarborough talks about the pressure behind modern leadership and why constant performance is leaving people disconnected from themselves, their teams, and the work they used to care about. The conversation explores burnout, identity, company culture, and the growing expectation that leaders should always be available, always producing, and always winning. Jason also shares why self-awareness, community, and honest conversations are becoming essential for leaders trying to build high-performing teams without losing themselves in the process. Chapters 00:00 Introduction and Setting the Scene 04:32 The Modern Leadership Trap 09:52 Finding Self-Worth in Leadership 15:01 The Impact of Social Media on Leadership Perception 18:08 Influencing Organizational Culture 18:48 Understanding Motivation and Empowerment 20:54 Navigating Organizational Change and Leadership 22:41 The Impact of Leadership on Team Dynamics 23:51 Balancing Performance and Personal Well-being 26:02 Adapting to Market Changes and Personal Fulfillment 29:25 Generational Shifts in Work Culture 31:38 Creating Safe Spaces for Personal Growth 34:38 The Role of Leadership in Organizational Health 37:43 Demand for Mental Health and Coaching in Organizations 39:45 Individual Responsibility in Personal Development 42:57 The Arcadia Leadership Experience References in the Show: https://www.cnbc.com/2026/05/05/executives-are-burning-out-dont-know-how-to-cope-management-experts.html  https://www.forbes.com/sites/lisacurtis/2026/04/29/the-ceos-beating-burnout-retention-loss-and-hustle-culture-all-at-once/  Quote of the Show: “I think part of the reason why we want Arcadia to focus on leaders is that everything rises and falls on leadership. How you operate and how you show up as a leader are going to be everything, and so is how your team shows up. The pressure you put under your team is going to rise and fall on the pressure that you feel in yourself.” - Jason Yarborough Ways to Tune In: Spotify: https://open.spotify.com/show/5GpM8myxsUinc5bfLIbjJz?si=0af576adfb8e49f8 Apple Podcasts: https://podcasts.apple.com/us/podcast/the-cheat-code/id1692445190 Amazon Music: https://music.amazon.com/podcasts/cb0b3afa-063f-4f3b-96be-b98214c74912 YouTube: https://www.youtube.com/@CheatCodePodcast

  7. May 8

    Category Creation, Problems and Storytelling - Season 5: Episode # 89

    The best companies win by changing how buyers think about the problem. Mike Damphousse joins the podcast to share the principles behind category creation and why most startups get trapped competing inside crowded markets they did not define. Drawing from his work with founders, investors, and high-growth companies, Mike explains how category design shifts the conversation away from product comparisons and toward strategic narrative. This episode covers product-market fit, emotional storytelling, positioning, and why strong messaging starts with identifying the missing piece in the market. Mike also shares lessons from working with startups at every stage, how companies create momentum around new ideas, and where AI may reshape strategic consulting in the years ahead. Chapters 00:00 Introduction to Category Design and Founding Journey 02:57 The Evolution of Green Leads and Category Design Advisors 06:11 The Importance of Category Creation in Business Strategy 09:01 Understanding Market Product Fit vs. Product Market Fit 11:50 The Role of Category Designers in Business 15:06 Challenges in Category Creation Mindset 18:10 Marketing the Problem, Not the Product 21:57 The Importance of Data in Category Design 23:59 Aligning Organizations for Category Creation 26:54 Deliverables and Execution in Category Design 30:11 The Future of Category Creation in an AI World References in the Show: https://www.thecategorycreationformula.com/  https://www.categorydesignadvisors.com/category-design-rx/  Quote of the Show: “I'm so impressed with what anybody can do with AI today. It's going to change the way we work, but it's not going to take away the work. It's just going to change how we operate. The new electricity.” - Mike Damphousse  Ways to Tune In: Spotify: https://open.spotify.com/show/5GpM8myxsUinc5bfLIbjJz?si=0af576adfb8e49f8 Apple Podcasts: https://podcasts.apple.com/us/podcast/the-cheat-code/id1692445190 Amazon Music: https://music.amazon.com/podcasts/cb0b3afa-063f-4f3b-96be-b98214c74912 YouTube: https://www.youtube.com/@CheatCodePodcast

  8. Apr 24

    Fundamentals, Risk and Differentiation - Season 5: Episode # 88

    In this episode of the Cheat Code + Friends podcast, Hannah Ajikawo shares what actually drives sales performance in competitive markets. As CEO and founder of Revenue Funnel, she explains why most teams focus too much on internal process and not enough on how buyers make decisions, which ultimately creates a gap that stalls growth. In her experience, sales fundamentals are getting ignored and buyers are getting harder to convince. Hannah shares how credibility is built, why borrowing trust can accelerate deals, and how strong execution often matters more than product differentiation. She also covers hiring, consultative selling, and the role of AI in shaping modern go-to-market without replacing the fundamentals. Looking for advice on partnerships, customer experience, and why helping buyers make confident decisions is the real job of sales? This episode has you covered.  Chapters 00:00 The Unsexy Fundamentals of Sales 05:53 Understanding Buyer Dynamics 09:02 Building Credibility in Sales 12:09 Navigating Competitive Markets 14:49 The Importance of Customer Experience 17:55 The Role of AI in Sales Strategy 20:49 The Power of Partnerships in B2B 24:23 Innovative Go-to-Market Strategies 25:19 Leveraging AI in Consulting 28:10 The Importance of Authenticity in Sales 30:49 Hiring the Right Sales Reps 39:45 Revenue Funnel's Unique Approach References in the Show: https://www.fastcompany.com/91464721/2026-will-be-the-year-marketers-rediscover-the-basics  https://www.forbes.com/councils/forbesagencycouncil/2026/02/10/the-b2b-buyer-journey-isnt-what-it-used-to-be  Quote of the Show: “When we think about the fundamentals, particularly wrapping it around the startup world, it's, who are you selling to? What problem are you solving? It's so unsexy that people cannot believe that's the conversation that we're starting with.” - Hannah Ajikawo Ways to Tune In: Spotify: https://open.spotify.com/show/5GpM8myxsUinc5bfLIbjJz?si=0af576adfb8e49f8 Apple Podcasts: https://podcasts.apple.com/us/podcast/the-cheat-code/id1692445190 Amazon Music: https://music.amazon.com/podcasts/cb0b3afa-063f-4f3b-96be-b98214c74912 YouTube: https://www.youtube.com/@CheatCodePodcast

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About

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. Combined with a rotating guest list of founders, practitioners and investors, the no-nonsense forum gathers fortnightly, holding court to translate headlines into reality and discuss the impact for early-stage businesses. The Cheat Code is just that, the trusted folks we look to for advice and insight, and we hope to bring the same to you. Game over.

Information

  • Creator
    In Revenue Capital
  • Years Active
    2023 - 2026
  • Episodes
    95
  • Rating
    Explicit
  • Copyright
    © 2023
  • Show Website
    The Cheat Code & Friends