The Cheat Code & Friends

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Jun 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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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.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, 2026Episode 9044 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

May 8, 2026Episode 8950 min

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.Chapters00:00 Introduction to Category Design and Founding Journey02:57 The Evolution of Green Leads and Category Design Advisors06:11 The Importance of Category Creation in Business Strategy09:01 Understanding Market Product Fit vs. Product Market Fit11:50 The Role of Category Designers in Business15:06 Challenges in Category Creation Mindset18:10 Marketing the Problem, Not the Product21:57 The Importance of Data in Category Design23:59 Aligning Organizations for Category Creation26:54 Deliverables and Execution in Category Design30:11 The Future of Category Creation in an AI WorldReferences 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

April 24, 2026Episode 8842 min

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. Chapters00:00 The Unsexy Fundamentals of Sales05:53 Understanding Buyer Dynamics09:02 Building Credibility in Sales12:09 Navigating Competitive Markets14:49 The Importance of Customer Experience17:55 The Role of AI in Sales Strategy20:49 The Power of Partnerships in B2B24:23 Innovative Go-to-Market Strategies25:19 Leveraging AI in Consulting28:10 The Importance of Authenticity in Sales30:49 Hiring the Right Sales Reps39:45 Revenue Funnel's Unique ApproachReferences 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 AjikawoWays 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

April 10, 2026Episode 8734 min

Gifting, Attention and Saturation - Season 5: Episode # 87

Listen now: Digital channels are getting saturated, and AI is accelerating the noise.Kris Rudeegraap shares how that shift is changing the way companies capture attention and build relationships. As CEO of Sendoso, he walks through why email alone no longer works, how gifting and direct mail are being used across the entire funnel, and what makes certain outreach actually stand out.Kris explains how teams are combining channels, using data to personalize at the individual level, and experimenting with creative sends that drive real engagement. He also breaks down how AI is shaping the future of go-to-market, from smarter timing and messaging to autonomous agents that support sales teams. Tune in for insights on acquisitions, scaling into new markets, and why human relationships are becoming more important as automation increases.Chapters00:00 Introduction and Personal Updates06:28 The Evolution of Sendoso and Gifting Strategies12:27 Market Trends and Segment Adoption14:29 Changing Buyer Behavior and Sales Strategies14:57 The Power of Gifting in Marketing18:10 Creative Use Cases for Gifting22:00 AI's Role in Personalization and Gifting24:17 Market Expansion and Customer Insights28:01 Navigating Acquisitions and Integration Challenges37:58 The Future of Sales with AI and Human InteractionReferences in the Show:https://www.giftbit.com/2026-trend-report https://ddbricks.com/post/corporate-gifting-trends-2026-from-objects-to-experiences-why-budgets-are-shifting Quote of the Show:“I still believe in email. I don't think email is dead. I just think you can't be email-only, which you could have been five years ago, 10 years ago. And so when you need to add other channels, one of the obvious ones that works really well is gifting a direct mail, and we're poised for helping a lot of companies since we've built the infrastructure and the data layer over the last decade.” - Kris RudeegraapWays 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

March 27, 2026Episode 8647 min

Coaching, Performance and Trust - Season 5: Episode # 86

Bad sales reps have always had places to hide. AI is starting to remove them.In this episode, Matthew Whyatt shares what happens when sales teams finally see the truth: which reps are really performing, which managers are actually coaching, and where deals start breaking down. The conversation focuses less on AI hype and more on what sales leaders can do with better visibility, better data, and better training.Matthew gives his opinion on why strong sales remains a human-to-human skill, even as AI reshapes how teams prepare, practice, and improve. He talks through the role of discovery, the danger of over-explaining in demos, and why guiding the buyer is often just as important as pitching the product.They also dig into objection handling, onboarding, sales management, and the growing pressure on leaders to raise standards rather than rely on instinct. Chapters00:00 Introduction and Light Banter02:59 Sales Backgrounds and Early Experiences06:01 The Impact of AI on Sales11:51 Sales Management and Coaching Challenges18:00 The Future of Sales with AI19:38 AI in Sales Training and Onboarding22:29 Challenges in Mid-Market and Enterprise Sales25:15 Real-Time Coaching and Sales Skills27:16 The Importance of Human Connection in Sales30:01 Guiding the Buyer Through the Sales Process36:01 The Role of Marketing in Modern Sales42:54 Tech Talk: Insights from Matthew WhyattReferences in the Show:https://www.linkedin.com/pulse/ai-wont-replace-your-sales-team-itll-just-expose-lazy-matthew-whyatt-kpq9c/?trackingId=a%2BGQ6EiGSH%2BeaPS8yVR63Q%3D%3D https://podcasts.apple.com/us/podcast/the-ceo-and-the-salesman-podcast/id1635865557 Quote of the Show:“AI is removing the nooks and crannies that crappy salespeople can hide in.” - Matthew Whyatt 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

March 13, 2026Episode 8543 min

Bottlenecks, Buyers and AI - Season 5: Episode # 85

This episode will change the way you think about sales leadership, buyer behavior, and what growth teams need to do next.Join the hosts for a conversation with Jake Dunlap, CEO of Skaled, on how AI is reshaping the modern revenue engine from the inside out. Jake breaks down why CROs are running out of time to treat AI like a side project, where most teams are misapplying it, and how the biggest opportunity isn’t in automating more noise, but in improving how sellers think, work, and create value.From prospecting and deal strategy to coaching, hiring, and customer experience, Jake shares a sharp perspective on what’s changing fastest in B2B sales. Listen in as he explains why buyers are moving ahead of most sales teams, why traditional sales playbooks are losing relevance, and why the future belongs to organizations that remove friction, move faster, and meet customers where they are.Chapters00:00 Introduction and Excitement for Snowboarding02:56 The Evolving Role of the CRO05:53 AI's Impact on Sales Processes09:04 Prospecting and Sales Strategies with AI11:53 The Future of Sales Leadership14:56 Implementing AI in Organizations18:01 Hiring and AI Proficiency21:04 The Changing Buyer Landscape24:03 Customer Experience and Sales27:11 Conclusion and Key TakeawaysReferences in the Show:https://www.forbes.com/councils/forbesbusinesscouncil/2025/12/15/the-winning-ai-strategies-of-high-growth-companies https://synoviadigital.com/insights/the-state-of-ai-in-2025-what-mckinseys-data-tells-us-about-2026 Quote of the Show:“AI is more of a shift in how we solve problems as humans, less of a new interesting technology.” - Jake DunlapWays 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

February 27, 2026Episode 8437 min

Handoffs, Experimentation and Agility - Season 5: Episode # 84

Startup land can be complete chaos… shifting buyer behavior, distributed teams, tighter budgets, and AI changing how work gets done. In this episode, John Eitel, CRO at Orum, explains what it all means for modern revenue leaders and why agility is no longer optional.Together, the hosts and John explore the death of the linear funnel, the resurgence of outbound, and why what was “old” in sales is suddenly working again. John also dives into the real leverage point most teams ignore: coaching and how AI can finally make it scalable without losing the human edge.The conversation questions long-held assumptions about SDRs, role specialization, and career paths, pushing leaders to rethink how their sales org is actually structured. This is about building revenue teams that experiment faster, learn quicker, and adapt before the market forces them to.Chapters00:00 Introduction to the Podcast and Guest02:55 Navigating Chaos in Startup Land05:52 The Impact of AI on Sales08:49 Balancing Scale and Personal Touch in Sales12:06 The Evolution of Sales Roles15:06 Understanding Ideal Customer Profiles (ICP)17:53 The Importance of Coaching in Sales21:02 Rethinking Sales Development Roles23:59 Career Pathing in Sales27:10 The Future of Sales Teams29:46 Final Thoughts on Experimentation and AdaptabilityReferences in the Show:https://www.sellingpower.com/23217/from-pipeline-to-prediction-the-ai-playbook-for-high-growth-sales-teams https://www.forbes.com/sites/lilianraji/2025/12/31/your-2026-marketing-strategy-edge-email-education-and-authenticity/ Quote of the Show:“No longer do our buyers all come into an office and sit at a desk with a phone on it. They're in a coffee shop, they're in their homes. They're now moving targets that buy differently. And then you put AI on top of that. I think that really was the third domino in this effect. But I think probably, again, those things all coming together have really sent this thing into a spin of change here.” - John EitelWays 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

February 12, 2026Episode 8346 min

Dialing, Data and Discipline - Season 5: Episode # 83

Joey Gilkey, CEO of TitanX, joins the show to tear down one of the most sacred ideas in go-to-market: that more activity equals more revenue.Joey argues that most sales teams aren’t failing because reps aren’t working hard enough. They’re failing because the system they’re operating inside is broken. Cold calling still works, but only if you stop treating every prospect the same. Most people will never answer the phone, and pretending otherwise destroys rep productivity, forecasting, and morale. By identifying who is actually reachable before a call is made, teams can radically change the economics of outbound.The conversation covers why SDR teams should be treated like a signal engine, not a meeting factory, and why founders keep defaulting to headcount when efficiency is the real constraint. By the end of the conversation, it’s hard to look at SDRs, outbound, or ‘activity metrics’ the same way again.Chapters00:00 Introduction and Setting the Stage05:05 Understanding Titan X's Value Proposition10:29 The Shift in Sales Strategies17:14 Redefining Sales Development as an Ad Channel20:15 The Importance of Messaging and Targeting21:21 Understanding Messaging by Persona24:41 The Importance of Follow-Up and Data27:49 Dispositions and Their Impact on Sales30:46 Data Aggregation and Coordination Drag34:22 The Reach Rate and Cold Calling Strategy39:18 Identifying Skill Gaps and Data Quality40:05 Customer Success and Operationalizing Sales43:01 The Challenges of Product-Led GrowthReferences in the Show:https://www.marketingbrew.com/stories/2025/12/18/cmos-on-overhyped-marketing-trends-in-2025 https://www.mckinsey.com/capabilities/growth-marketing-and-sales/our-insights/the-cmos-comeback-aligning-the-c-suite-to-drive-customer-centric-growth Quote of the Show:"An ad doesn't give us feedback. An email doesn't give us feedback. It's why I love the phone. It's just conversational advertising. If we can activate an audience, not even around conversions and appointments and meetings, and instead we can uncover interest and intrigue and intent, the three I's, and we can take that intel, that could be the mitochondria, the powerhouse of the go-to-market cell, which is, I'm on the front lines getting information that no one else has from my SDRs.” - Joey GilkeyWays 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

January 30, 2026Episode 8239 min

ICPs, Niche Markets and Expansion - Season 5: Episode # 82

Mike Huffaker, CRO, Planet DDS, joins the show to share what actually drives real growth in a vertical SaaS market where “going broad” is the default trap.Mike explains why narrowing to a true ideal customer profile can feel terrifying, but becomes a growth cheat code once you commit: higher win rates, higher ASPs, clearer messaging, and less competitive deal cycles. He also gets candid about the part most teams underestimate after they move upmarket: implementation. In Mike’s dental niche, going live means data conversion, workflow change, training across roles, and real internal leadership from the customer side. If you can’t deliver outcomes post-sale… none of the bookings matter.Chapters00:00 Introduction to Growth Strategies02:56 Targeting Ideal Customer Profiles05:51 Internal Buy-In for Market Focus09:12 Team Structure and Talent Acquisition11:59 Implementation Challenges and Customer Success14:58 The Role of AI in Implementation18:13 Revenue Growth and Account Management20:56 Navigating Complex Sales Processes23:59 Hiring for Success in Enterprise Sales26:50 Conclusion and Key TakeawaysReferences in the Show:https://www.forbes.com/sites/jodiecook/2025/08/08/5-chatgpt-prompts-to-define-your-ideal-customer-profile/ https://www.entrepreneur.com/growing-a-business/how-defining-my-ideal-client-profile-transformed-my-business/498064 https://martech.org/the-biggest-ideal-customer-profile-mistakes-businesses-make-and-how-to-fix-them/ Quote of the Show:"We did a lot of modeling on what we were generating from an MQL perspective, what we expected we could do from an outbound motion as well. And we got everyone pretty comfortable with it. And it's turned out to be something where the team now appreciates not having to work through. I guess, for lack of a better term, things that just keep you busy that don't really drive results.” - Mike HuffakerWays 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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