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.
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...
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...
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...
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...
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.
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Conviction, Community and Contrarian Investing - Season 5: Episode # 92
In this episode, Isabelle Tashima shares why some of the best businesses are easy to overlook in their early days. At Volition Capital, she has spent years studying companies that create outsized outcomes, and many of them don't fit the conventional growth playbook.
Using examples like Chewy and US Mobile, Isabelle explains why customer loyalty, community, and founder conviction often become more valuable than short-term growth metrics. She discusses how great companies earn trust, turn customers into advocates, and build distribution advantages that competitors struggle to replicate. Isabelle also discusses what investors look for...
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...
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...
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...
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...
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...
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...
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 isnât in automating more noise, but in improving how sellers think, work, and create value.
...
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 âoldâ 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...
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 arenât failing because reps arenât working hard enough. Theyâre failing because the system theyâre 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 t...
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 âgoing broadâ 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 Mikeâs dental niche, going live means data conversion, workflow change, training across roles, and real internal leader...
Unicorns, Duct-Tape and Expectations - Season 5: Episode # 81
Hiring marketing talent is one of the biggest blind spots for early-stage founders, and Jessica Gilmartin has seen the same mistakes play out over and over again.
In this episode, Jessica (former CMO/CRO at Calendly) shares why âmarketingâ is actually multiple jobs, how to decide whether you need demand gen, product marketing, or brand, and why most founders hire the right person for the wrong stage. She shares real frameworks for setting clear expectations, building trust through communication, and avoiding the toxic ripple effects of a bad hire.
The...
Christmas, Chaos and GTM - Season 4: Episode #80
Itâs the Cheat Code Christmas Special! Join the hosts for an always colorful, yet never without value, conversation with Craig Rosenberg and Scott Albro on what actually works in go-to-market right now and why most founders are getting it wrong.
If youâre trying to break through buyer apathy, build a brand from scratch, or rethink how you go to market in 2026, this episode will challenge a lot of assumptions. In a world defined by the attention economy, economic uncertainty, and buyer skepticism, Craig and Scott break down why traditional GTM playbooks are fail...
Data, Leverage and Leadership - Season 4: Episode # 79
Tune in for a conversation with Kyle Norton, Chief Revenue Officer at Owner.com, on how modern revenue teams are using AI, data, and systems thinking to do more with less. Kyle breaks down how Owner built a highly efficient go-to-market engine by combining deep customer understanding with proprietary data, machine learning models, and relentless operational rigor.Â
The hosts dig into why todayâs CRO must think like a systems engineer, how to evaluate AI tools without chasing silver bullets, and what founders get wrong when they expect AI to fix broken sales motions. The...
Signals, Saturation and Shift - Season 4: Episode # 78
Join the hosts for a conversation with Jon Miller, co-founder of Marketo and one of the most influential minds in modern marketing, on how AI, tactic fatigue, and buyer anonymity are forcing marketers to evolve faster than ever. Together they explore the cracks forming in legacy marketing automation and the rise of signal-based journeys. Jon breaks down why the next decade of marketing wonât look anything like the last.
This episode explains why marketers must shift from tactics to context, how AI can streamline operations without sacrificing creativity, and why sales and marketing al...
Hiring, Grit and Risk - Season 4: Episode # 77
If youâve ever underestimated the power of hiring, this episode will change the way you think about growth.
Join the hosts for a conversation with Dr. Heidi Ojha, Founder and CEO of Aware Health, on how no-nonsense hiring can make or break your growth story. From identifying organizational gaps to building scalable hiring processes, Heidi shares what it takes to grow a team in one of the toughest sectors: healthcare. She explains why founders should approach hiring like a marketing campaign, the traits that define true high performers, and how onboarding and culture in...
Talent, DNA and Trust - Season 4: Episode # 76
Tune in for a conversation with the man, the myth, the legend, Bill Binch, Operating Partner at Battery Ventures and former sales executive at Marketo, on what it really takes to build high-performing sales teams in todayâs AI-driven world.
From hiring for the right sales mindset to building customer-focused teams and scalable sales processes, Bill shares hard-earned lessons from decades of leading and advising top SaaS companies. He breaks down how founders can make smarter sales hires, why continuous learning separates great leaders from the rest, and how AI is reshaping the future of...
Disruption, Revenue and Relationships - Season 4: Episode # 75
The world of sales is changing fast and the playbooks that fueled growth a few years ago arenât enough anymore.
In this special hosts-only episode, Justin, Josh and Sean break down what todayâs shifting startup and sales environment really means for go-to-market teams. From evolving buyer expectations to the rise of AI-driven strategies, they explore how top performers are adapting to meet customers where they are and where theyâre going next. Youâll hear insights on the new role of full-cycle AEs, why post-sale engagement is the key to long-term growth, and how...
Compensation, Culture and Accountability - Season 4: Episode # 74
Tune in for a conversation with Mark Schopmeyer, Co-Founder and Co-CEO of CaptivateIQ, on how incentive compensation can make or break the success of an early-stage company.
From the critical role of founding AEs to the delicate balance between keeping plans simple and aligning them with big-picture goals, Mark explains why no single model works for every business. They dig into the importance of trust and transparency in compensation plans, how leadership choices shape performance, and why cultural alignment is just as powerful as equity when it comes to motivating teams. Youâll also he...
Strippers, RTO and Sales - Season 4: Episode # 73
A former single mom, stripper, and felon turned two-time author and VP of Innovative Disruption at Lift Enablement, Dr. V lays out hard lessons and simple truths on resilience, sales talent, and reportingâwithout the euphemisms. In this episode, we talk about what most teams tiptoe around: who you hire, how you build culture, and why âreturn to officeâ means nothing if the office isnât safe.
This episode is candid, occasionally spicy, and packed with immediately usable hiring and enablement takeaways.
Chapters
00:00 â Cold open & why...
Nerds, Arizona and Connections - Season 4: Episode # 72
Tune in for a conversation with Don Fotsch, Cofounder of BDS AI (Battery Detection Systems), on how Arizonaâs tech ecosystem is growing into a hub of innovation and opportunity.
From bridging the gap between talent and funding to redefining how values shape hiring and community building, Don explains what it takes to grow a thriving startup culture outside of Silicon Valley. They dig into the challenges of post-pandemic workforce development, why real-world experience is often more valuable than traditional education, and how mentorship and collaboration can fuel the next generation of entrepreneurs. If yo...
Reps, Robots and Results - Season 4: Episode # 71
Tune in for a conversation with Justin Michael, Founder of the Justin Michael Method, on how AI is reshaping sales without replacing what matters most: the human connection.Â
From the enduring power of cold calling to the fine line between hyper-personalization and just being relevant, Justin explains what modern sales teams need to know to win. They dig into the rise of fractional work, why consulting can unlock both freedom and income, and how the smartest sales leaders are using AI as a force multiplier, not a crutch. If you want a front-row seat t...
Venture Capital Mindset, Founder-Led Sales and Resilience - Season 4: Episode # 70
Join the hosts for a conversation with Vasant Kamath, General Partner at Noro-Moseley Partners, on what it really takes to win in todayâs venture capital game. From navigating high-stakes funding rounds to building sales teams that actually close, Vasant shares hard-earned insights on driving sustainable growth without losing speed. They dig into whatâs driving change in venture capital, the non-negotiable need to know your customer cold, and why adaptability isnât optional, itâs survival.
Chapters
00:00 Introduction and Light Banter
02:59 The Current State of Venture Capital Funding
05:46...
Liquidity, Hustle and Trust- Season 4: Episode # 69
Listen in as we talk with Craig Coppola, a seasoned investor, entrepreneur, and commercial real estate legend, to discuss the messy reality of startup investing. From assessing founder grit to navigating lean liquidity environments, Craig shares what makes a deal worth chasing (and what makes him walk away). We talk about the hard truths of entrepreneurship, why trusting the âjockeyâ matters more than the âhorse,â and how the best investors build long-term success on discipline, culture, and conviction.
If you're raising capital, building a company, or considering your first investment, this episode shares what it takes...
Tribal Training, Onboarding and Change- Season 4: Episode # 68
In this episode, we sit down with Chris Ronzio, Founder and CEO of Trainual, to explore how companies can build smarter, more scalable systems for onboarding, training, and internal knowledge management. Chris shares why documenting institutional knowledge is a necessity and how AI is changing the game for employee development and organizational efficiency.
From creating proactive candidate pipelines to rethinking how we prepare people for the workforce, this conversation covers all things education, hiring, and training. If youâre scaling a team, rethinking your hiring strategy, or simply trying to keep up with the pa...
Homeschoolers, Autonomy and Access- Season 4: Episode # 67
Join us for a conversation with Jared Fuller as he shares his unique journey from the world of B2B and GTM partnerships to the forefront of education reform. As Partner and Chief Operating Officer of OpenEd.co, Jared is on a mission to transform homeschooling by empowering families with customizable curriculum options and a more personalized approach to learning.
This episode explores the shift from the economics of homeschooling and state funding models to the growing demand for alternatives to traditional schools. Jared shares why trust, community, and flexibility are becoming essential pillars...
Ageism, Curiosity, and Fist Bumps- Season 4: Episode # 66
Join us for a lively conversation with Dan Tyre, one of HubSpotâs earliest employees and a passionate advocate for startup growth, sales excellence, and lifelong learning. With humor and energy, Dan shares his journey at HubSpot and how the companyâs sales strategy evolved alongside a rapidly changing workforce.Â
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From tackling ageism in tech to highlighting the value of curiosity, this episode explores what it takes to succeed in todayâs job market. Dan shares practical tips on adaptability, preparation, and building strong relationships, offering a roadmap for anyone navigating career growth or startup life. <...
Being Fractional, Going Analog and Building Communities- Season 4: Episode # 65
Listen in for a conversation with Jason and Sam Yarborough on what it takes to build a business and their experience building Arcadia, a consultancy focused on partner programs. From the challenges of fractional leadership to the power of authentic partnerships, this episode explores how todayâs founders are navigating business growth, community building, and curating connections. Plus, a look ahead at the future of Arcadia and the role of digital tools in preserving meaningful relationships.Â
Chapters
00:00 Introduction Â
03:01 Starting a Business in the Age of AI
06:04 The Evolution of Arcadia
Obsession, Self-Awareness, and the Founder-to-CEO Leap - Season 4: Episode # 64
Gregg Scoresby, Founder and Managing Partner of Phoenix Ventures, joins the hosts to break down the traits that separate winning Founders from wannabes. From hiring blind spots to co-founder clashes, founder-to-CEO transitions, and spotting red flags, this episode looks at what it really takes to build and lead a killer startup.
Chapters
00:00 The Essence of Founder Traits
10:01 The Role of Subject Matter Expertise
14:28 The Path to Foundership: Backgrounds and Skills
19:29 Hiring for Deficits: The Key to Team Success
22:41 Navigating Co-Founder Relationships: The Importance of...
Market Challenges, Bootstrapping, and Founder Expectations - Season 4: Episode # 63
Whatâs the real story behind funding a startup today? Greg Head, founder of Practical Founders, joins the hosts to break down the world of bootstrapping vs VC funding. From capital strategy to AI-driven growth, this episode digs into what actually works in todayâs market. From chasing VC or building lean, this episode is packed with discussion on funding models, founder expectations, and the impact of AI on business strategies.
Chapters
00:00 Market Trends and Economic Challenges
02:47 Capital Allocation vs. Bootstrapping
06:12 The Global Landscape of Founders
08...
Marketing Hires, Hype, and the Role of AI - Season 4: Episode # 62
Marketing has never been more complicated or more important. In this episode, Kyle Lacy, CMO of Docebo, joins the hosts to unpack the chaos: from hiring in a fragmented job market to redefining marketing's role in driving revenue. Together they dive into personal branding, pipeline obsession, AIâs creeping influence, and whether great marketers really exist, or if itâs all just great products. If youâve ever questioned the hype around brand, customer-centricity, or why marketing still feels misunderstood, this oneâs for you.
Chapters
00:00 Introduction to Marketing Conversations
02:57 The Role...
Adios DEI? Roadblocks, Inclusion and Progress â Season 4: Episode # 61
In this episode, Stacey Lewis, founder and CEO of HR Interrupted, sits down for a brass-tacks conversation on how startups and high-growth businesses can navigate the murky waters of human resources (HR) and diversity, equity, and inclusion (DEI). As the pendulum swings, seemingly away from what has dominated the business landscape for the last half-decade, itâs more difficult than ever to simply âdo the right thingâ and even to know what that right thing is. Together the group discusses what really matters when attempting to build high-performing teams, the importance of employee voices, and fostering workplace relationships while also n...
Navigating the AI Hype Cycle with Scott Albro- Season 4: Episode # 60
The hosts welcome Scott Albro to their podcast for a discussion on venture capital trends and AI. They compare B2B vs. B2C AI adoption, emphasizing outcome-driven solutions. Together they explore AIâs impact on industries, labor markets, job roles, and startup founding teams.Â
Chapters
04:59 The State of Venture Capital and AI Startups
10:01 B2B vs B2C in AI Adoption
15:00 Transformative Growth in AI Startups
18:48 Addressing Labor Market Challenges
22:32 The Evolution of Job Roles in Tech
23:43 Agent-to-Agent Communication and LLMs
2...
Board Meetings, GTM Black Hole, CEO Report Card - Season 4: Episode # 59
From the GTM Cheat Code to âThe Cheat Code and Friends,â season 4 kicks off with the core crew only as Justin, Josh and Sean introduce this season's new format and cover some burning topics revealed by the start of the year - better known as 'Board meeting season.'
00:00 Introduction and Setup for New Season
(05:51) Board Meeting Dynamics
(09:03) Board Structure and CEO Support
(11:59) Effective Board Presentations
(15:03) Decision-Making in Board Meetings
(17:59) Go-To-Market Strategies and Challenges
(22:12) Navigating the Marketing and Sales Landscape
(26:10) The Power of F...
Kyle Lacy on How To Do Everything You Want To - Season 3: Marketing - Episode # 58
Join us for the Season 3 finale! Kyle Lacy dives into the pivotal role marketing plays in achieving goals across the business and how owning a number is key. From navigating top-down and bottom-up revenue goal setting to empowering founders in the process, Kyle unpacks strategies that keep marketing leaders agile and data-driven.
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Plus, hear about Kyleâs latest venture, The Revenue Diaries, where he shares lessons on scaling software businesses and personal growth. If youâre ready to supercharge your marketing efforts, this episode is a must-listen!
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Takeaways:Â
Marketing Owns a Reven...