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The Cheat Code & Friends: Daily Summaries Delivered
by 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.
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- 1 weeks ago44 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.Chapters00:00 Introduction and Guest Introduction00:24 Market shifts and venture focus02:11 Justin Gray's background and office tour04:02 Justin Gray's discussion on venture themes05:26 Introduction of Brad and his background07:20 Why B2B SaaS dominates venture capital08:08 Emerging sectors and opportunities in venture11:14 Venture investment criteria and valuation insights13:12 Market cycles and venture strategies16:08 Current trends in venture funding and exit strategies18:28 Cannabis industry insights and distressed opportunities23:03 Recapitalization and restructuring in distressed assets27:25 AI's impact on enterprise and vertical solutions34:01 Data security, privacy, and AI challenges40:41 Opportunities in cannabis and distressed assets44:43 Market cycles and strategic investing46:44 Advice for founders and investors in volatile markets47:57 Closing remarks and next stepsReferences 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 KotanskyWays 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 weeks ago38 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.Chapters00:00 Introduction to Ascendius and AI in Business02:53 AI's Role in Organizational Structure06:08 The Human Element in AI Integration08:57 Transforming Meetings and Management11:49 Navigating AI Implementation Challenges20:13 Understanding the Complexity of AI Training23:20 Navigating Data Quality and Input Integrity26:38 The Role of AI in Organizational Dynamics29:48 Sales Engineering in the Age of AI32:47 Balancing Accountability and Performance36:51 Creating a Centralized Organizational Knowledge BaseReferences 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 McQueenWays 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
- Aug 14, 202648 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.Chapters00:00 Introduction and episode overview02:00 Lauren's recent activities and 'tour de interesting'07:02 Key findings on business growth constraints08:31 Leadership challenges in AI and go-to-market11:51 Characteristics of effective leaders in tech15:01 The importance of ICP and fundamentals18:06 Building trust and proximity in sales21:47 Managing organizational drift and operational debt25:50 Supporting teams and preventing burnout30:03 Leadership practices for change management35:58 Women in Revenue and mentorship initiatives43:58 Connecting with Lauren and closing remarksReferences 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 GoldsteinWays 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
- Jul 31, 202652 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.Chapters00:00 Introduction and guest background02:17 Stage 2 Capital's investment thesis and history05:30 Market evolution from 2018 to today10:07 Impact of AI on venture and market opportunities15:04 The role of curiosity and innovation in startups20:42 Pricing models and outcome-based strategies in AI25:46 Customer success, retention, and long-term value30:09 Valuation approaches and market dynamics36:09 The messiness and opportunities in early-stage investing40:14 Valuation discipline and market noise45:05 Future outlook and strategic positioningReferences 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 PoWays 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
- Jul 17, 202648 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.Chapters02:36 JT Bricker's background and role at Grazzy05:39 Prioritization in high-growth SaaS companies09:08 Entering a business organically and intentionally13:39 Assessing companies in a changing funding environment17:27 The importance of focus and operational excellence21:02 Triangulating customer value and growth23:17 Pricing, packaging, and unit economics in SaaS26:36 Building usage flywheels and scalable products30:41 The shift to consumption-based models and sales strategies34:20 Impact of AI on sales, customer success, and talent43:56 Talent acquisition and strategic hiring in SaaS48:24 Final thoughts on prioritization and growth strategiesReferences 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 BrickerWays 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
- Jul 3, 202647 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.Chapters03:54 Grant Siders: Background and Helia's Mission08:01 Understanding Healthcare Procurement Challenges12:32 The Financial Implications of Medical Device Procurement17:44 Prioritizing Focus and Decision-Making in Startups21:41 Driving Enterprise Value in Healthcare Networks24:00 Navigating Early Sales Cycles and Market Education26:04 Data-Driven Decisions in Healthcare27:55 Operational Cadence and Strategic Clarity34:01 Building a Culture of Accountability38:56 Adapting to Change and Future GrowthReferences 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 SidersWays 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
- Jun 5, 202641 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.Chapters00:00 The Evolution of Tech Conferences09:00 Navigating the Changing Landscape of Marketing19:00 The Role of CMOs in Modern Marketing22:04 Cultural Change in Marketing24:34 Rethinking Marketing's Role26:18 Trust and Marketing Leadership28:54 The Evolution of Marketing Metrics30:11 Challenges in Early-Stage Marketing32:26 The Importance of Brand Credibility34:54 Building Customer Confidence39:20 The Comeback of Events42:28 Creative Approaches to Events47:10 Budgeting for Marketing SuccesReferences 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 HeinzWays 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
- May 22, 202644 min
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.Chapters00:00 Introduction and Setting the Scene04:32 The Modern Leadership Trap09:52 Finding Self-Worth in Leadership15:01 The Impact of Social Media on Leadership Perception18:08 Influencing Organizational Culture18:48 Understanding Motivation and Empowerment20:54 Navigating Organizational Change and Leadership22:41 The Impact of Leadership on Team Dynamics23:51 Balancing Performance and Personal Well-being26:02 Adapting to Market Changes and Personal Fulfillment29:25 Generational Shifts in Work Culture31:38 Creating Safe Spaces for Personal Growth34:38 The Role of Leadership in Organizational Health37:43 Demand for Mental Health and Coaching in Organizations39:45 Individual Responsibility in Personal Development42:57 The Arcadia Leadership ExperienceReferences 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 YarboroughWays 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
About The 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. 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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