The Cheat Code & Friends

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Oct 2026

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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.

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October 23, 2026Episode 10042 min

100 Episodes, Zero Scripts - Season 5: Episode # 100

100 episodes. Three hosts. A few questionable party hats. The Cheat Code & Friends is celebrating its centennial. For this special episode, Justin, Josh and Sean ditch the guests and take a look back at the conversations, characters and unexpected lessons from the first 100 episodes. What started as a podcast about go-to-market cheats has turned into something more valuable, with some of the best conversations coming from people who challenged the guys to think differently. They revisit the guests who left a mark, from Dr. V challenging their perspectives on workplace culture to Jason Yarborough explaining why winning can hide serious problems. They get into the ideas that kept showing up across the years: why trust matters so much in GTM, what AI actually changes, how founders should think about capital, and why the best business advice is often painfully simple. There are plenty of shoutouts to old friends, a few stories from behind the scenes, and some appreciation for the people who've made the show worth showing up for every week. A hundred episodes in, the guys still don't have all the answers. But they've met some pretty interesting people along the way. Here's to 100 more. Chapters 00:00 Introduction and milestone celebration 01:59 Reflections on trust as a fundamental business driver 04:00 Building a brand that fosters trust and authenticity 06:00 The role of AI in exposing weaknesses and enabling scale 08:00 Notable guests and their impactful insights 09:56 Lessons on leadership, culture, and navigating challenges 12:10 The importance of niche focus and authenticity in branding 14:01 The trust hack and leveraging partnerships 16:13 The evolving role of human judgment in the AI age 18:08 Reflections on memorable episodes and guests 20:07 Future outlook and closing thoughts References in the Show: Jason Yarborough , Jared Fuller , Matt Heinz , Scott Albro, Geoff McQueen , Jason Vargas , Matthew Whyatt , Dr. V (Boykin) , Dan Tyre , Brad Kotansky , Greg Head , Stacey Lewis , Kyle Lacy , Joe Chernov , Craig Coppola , Grant Siders , Katie Martell , Ted Purcell , Craig Rosenberg , Lauren Goldstein , Andrea Lechner-Becker , Chris Walker , Jay Po , Chris Walton , Max Altschuler , Kevin O'Malley Quote of the Show: “Well, long story short, the takeaway from this is there's no shortage of great people that we've had the honor to speak with. I didn't think we'd do a hundred of these. Looking back on it and spending a little bit of time reflecting, maybe we'll do a hundred more, I don't know. I wouldn't mind it. As long as we can keep finding great, great folks, it's an enjoyable process and truly an honor.” - Justin Gray 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

October 9, 2026Episode 9943 min

Relationships, Serendipity and Compounding - Season 5: Episode # 99

There's a big difference between having a great network and treating everyone you meet like they might be useful someday. Chris Walton, Founder and CEO of ATLAS, has built businesses across real estate and hospitality, and many of the biggest opportunities in his career have come through people he knows. But he isn't collecting contacts or building relationships around what someone might eventually do for him. His approach is almost the opposite: get to know interesting people, figure out what matters to them, help when you can and stay open to where it leads. Chris joins Justin, Josh and Sean to talk about what it looks like to be intentional about relationships without making them transactional. They get into building credibility, making introductions that create value for both sides, why asking for help can sometimes strengthen a relationship, and the patience required to let a network compound over years instead of trying to “activate” it when you need something. The bigger takeaway: relationships aren't something you “activate” when you need them. They're something you invest in over a lifetime, and the relationship itself has to be worth something regardless of what comes from it. Chapters 00:00 Introduction and episode overview 02:00 Chris Walton's background and entrepreneurial journey 03:58 The significance of relationships as assets 12:02 Strategies for authentic relationship building 17:09 The importance of credibility and energy in networking 21:59 Giving and helping others as a core principle 27:54 Serendipity and creating opportunities through openness 34:02 Long-term relationship focus and trust 40:00 Crazy stories and unexpected outcomes from networking 43:07 Final thoughts on relationship as a life and business asset References in the Show: https://www.atlasphx.com/ https://www.forbes.com/sites/rodgerdeanduncan/2025/12/13/why-deep-relationships-outperform-big-networks/ https://www.forbes.com/sites/williamarruda/2026/08/18/relationships-win-in-business-heres-how-to-build-them-in-the-ai-era/ Quote of the Show: “I had an epiphany maybe within the last year or two, and that is relationships are the single greatest asset in our life. Period. If you think about first principles, it is an outcome, like an intended potential outcome. That's kind of the tip of the spear for me. And it could come in a number of different forms.” - Chris Walton 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

September 25, 2026Episode 9843 min

Taste, Judgment and Scale - Season 5: Episode # 98

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 judgment may become one of their biggest advantages. Jason joins Sean, Justin and Josh to discuss how companies can actually build a taste layer, who should be responsible for it, and why it needs to evolve alongside the people, buyers and business itself. They also explore what AI means for traditional GTM team structures, how organizations can train agents more like employees, and why scaling AI successfully still requires humans who know what good looks like. Chapters 00:00 Introduction to the taste layer in AI 01:56 The importance of judgment in AI systems 04:00 How organizations can build their taste layer 07:59 The role of human judgment and experience 12:01 Challenges in developing the taste layer 15:48 Organizational structure and AI responsibility 19:49 Onboarding and evolving the taste layer 24:00 Digital twins and AI in organizational context 27:57 Success stories and examples of taste layer implementation 32:05 Future opportunities and closing thoughts References in the Show: https://councils.forbes.com/blog/ai-is-cool-but-2026s-most-valuable-marketing-asset-is-still-human-taste https://hbr.org/2026/08/ai-is-undermining-leaders-judgment-heres-what-to-do-about-it Quote of the Show: “You have to be able to push back on [AI] and to bring your judgment into whatever it brings back. You have to bring your experience of building companies, running teams, coaching people, whatever. You have to bring that into the conversation with it, and you have to be able to spar with it. That helps you build the judgment. That's what I'm doing personally, and it helps. But you can't take what it brings back to you at face value. You always have to challenge, like, ‘Where'd you find that? Show me a link, or why did you say that?’” - Jason Vargas 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

September 11, 2026Episode 9744 min

Distress, Discipline and Gasoline - Season 5: Episode # 97

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 recapitalizations, distressed businesses, overlooked industries, and companies with broken capital structures that can be reset for their next stage of growth. That perspective requires a different definition of a good investment. A company doesn't need to become a thousand-times return to create an exceptional outcome, and raising more capital isn't always the answer. Brad shares why investors need to understand the business beneath the valuation, why founders should resist the pressure to "incinerate money," and why the best time to pour gasoline on a company is only after you've found the fire. Chapters 00:00 Introduction and Guest Introduction 00:24 Market shifts and venture focus 02:11 Justin Gray's background and office tour 04:02 Justin Gray's discussion on venture themes 05:26 Introduction of Brad and his background 07:20 Why B2B SaaS dominates venture capital 08:08 Emerging sectors and opportunities in venture 11:14 Venture investment criteria and valuation insights 13:12 Market cycles and venture strategies 16:08 Current trends in venture funding and exit strategies 18:28 Cannabis industry insights and distressed opportunities 23:03 Recapitalization and restructuring in distressed assets 27:25 AI's impact on enterprise and vertical solutions 34:01 Data security, privacy, and AI challenges 40:41 Opportunities in cannabis and distressed assets 44:43 Market cycles and strategic investing 46:44 Advice for founders and investors in volatile markets 47:57 Closing remarks and next steps References in the Show: https://www.gsb.stanford.edu/insights/search-funds-keep-offering-proven-path-ownership https://news.crunchbase.com/venture/logic-behind-vc-bets-uninvestable-sectors-cuvelier-rtp-global/ Quote of the Show: “There's so much sexiness and hype around ‘I got venture money’... ignore the hype. Your goal here is to build a strong business that has really strong growth that ultimately is cash flowing and paying everyone large dividends or is acquired for a good multiple. You don't need to incinerate money to do that.” - Brad Kotansky 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

August 28, 2026Episode 9638 min

Intelligence, Hierarchies and Humans - Season 5: Episode # 96

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 managers spend too much time moving information instead of coaching people, how AI could flatten traditional org structures, and why better visibility could allow leaders to focus more on judgment, development, and the work that actually moves the company forward. But more visibility also means more accountability. When leaders can see where people are spending their time, where work is getting stuck, and who is actually performing, there are fewer places to hide. Geoff believes that could ultimately make great managers and employees more valuable, not less, while forcing companies to rethink what human leadership should look like when AI can handle more of the information moving through the organization. Chapters 00:00 Introduction to Ascendius and AI in Business 02:53 AI's Role in Organizational Structure 06:08 The Human Element in AI Integration 08:57 Transforming Meetings and Management 11:49 Navigating AI Implementation Challenges 20:13 Understanding the Complexity of AI Training 23:20 Navigating Data Quality and Input Integrity 26:38 The Role of AI in Organizational Dynamics 29:48 Sales Engineering in the Age of AI 32:47 Balancing Accountability and Performance 36:51 Creating a Centralized Organizational Knowledge Base References in the Show: https://www.businessinsider.com/jack-dorsey-all-6000-employees-reporting-ceo-middle-managers-2026-4 https://www.wired.com/story/tech-ceos-using-ai-to-be-everywhere-at-once/ Quote of the Show: “In computer science, we have this phrase of ‘garbage in, garbage out.’ I'm sure it's been used in lots of industries. And an AI makes that all of a sudden like a toddler with an assault rifle. It's super dangerous. Because what you've got is potentially garbage going in, but the AI makes the output look beautiful and sound so credible and so smart.” - Geoff McQueen 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

August 14, 2026Episode 9548 min

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

July 31, 2026Episode 9452 min

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

July 17, 2026Episode 9348 min

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

July 3, 2026Episode 9247 min

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

June 5, 2026Episode 9141 min

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

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