The Cheat Code & Friends

In Revenue Capital
  • 5.0 (6)
  • BUSINESS
  • UPDATED WEEKLY

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.

  1. 1D AGO

    Venture Capital Mindset, Founder-Led Sales and Resilience with Vasant Kamath - 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 today’s 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 what’s driving change in venture capital, the non-negotiable need to know your customer cold, and why adaptability isn’t optional, it’s survival. Chapters 00:00 Introduction and Light Banter 02:59 The Current State of Venture Capital Funding 05:46 Understanding Growth and Sustainability in Startups 08:53 The Shift in Venture Capital Mindset 11:35 Navigating Early Stage Investments 14:39 The Importance of Founders in Sales 17:29 Building a Strong Go-to-Market Strategy 20:47 The Role of Sales Teams in Startups 23:29 Challenges in Forecasting and Pipeline Management 26:41 Exciting Trends in the Market 29:22 Final Thoughts and Wrap-Up References in the Show: https://www.businessinsider.com/vc-ai-herd-mentality-jay-hoag-tcv-kids-playing-soccer-2025-06  https://www.saastr.com/the-great-saas-slowdown-what-q1-2025-numbers-reveal-about-the-cloud-software-market/  https://news.crunchbase.com/venture/startup-investment-charts-q1-2025/  Quote of the Show: "You've got to figure stuff out really fast because that's the only way you survive in early stage. And then once you find something that works, you can double down on it. But oftentimes I see early stage companies, that's not just founders and CEOs, but their management teams, fall into the trap of being really scared. Scared of making decisions, scared of making tough decisions, scared of moving on from strategies or people or whatever, what happens then is that they're just prolonging the failure of the company.” - Vasant Kamath 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

    46 min

  2. AUG 1

    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 “jockey” matters more than the “horse,” 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 to win and what pitfalls to avoid when betting on startups. Chapters 00:00 Introduction and Team Dynamics 02:58 Craig's Journey into Investing 06:05 The Evolution of Investment Strategies 09:12 Navigating Deal Flow and Investment Decisions 11:47 The Importance of Cash Flow in Startups 15:04 Market Trends and Liquidity Challenges 22:35 Navigating Founder Commitments and Financial Strategies 23:48 Evaluating Deals: Red Flags and Founder Investment 25:53 The Challenges of Business Growth and Execution 28:41 Lessons from Experience: The Hard Truths of Startups 30:06 The Importance of Sales and Team Dynamics 32:09 Building a Culture of Execution and Learning 34:51 Transitioning from Founder-Led Sales to a Sales Team 39:15 Advice for Aspiring Investors: Finding the Right Path References in the Show: https://www.wsj.com/articles/angel-investing-isnt-what-it-used-to-be-e643c862 https://www.linkedin.com/posts/craigcoppola_c2voice-recenttransactions-officemarket-activity-7320929470763171840-Qv_K/?utm_source=share&utm_medium=member_desktop&rcm=ACoAABGQUe0BsV-UBJEAh7QOmp9oMj11PxcnemE   Quote of the Show: “Entrepreneurial means you've got to make great business decisions. And so to me, you can negotiate a better deal if you're cashflow positive and you're telling them, I don't need the money. We have one of those right now where he's growing like crazy. He doesn't need the money. And it's like, if I take money, it's going to be for the right reason…This is what I want. When you look like a founder like that, I don't mind investing with somebody for the second time.” - Craig Coppola 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

    40 min

  3. JUL 18

    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 you’re scaling a team, rethinking your hiring strategy, or simply trying to keep up with the pace of change, this episode shares insights on the systems and mindsets needed to succeed in the future of work. Chapters 00:00 Introduction and Background 03:01 The Importance of Onboarding and Training 05:58 The Role of Culture in Employee Retention 09:01 Leveraging Technology for Knowledge Management 11:51 Data-Driven Insights on Onboarding 14:56 The Last Mile of Employee Training 18:06 Hiring Trends and Talent Gaps 21:09 Proactive Hiring Strategies 24:14 Building a Talent Pipeline 26:09 Leveraging AI in Recruitment 30:36 Roles and Responsibilities in Organizations 32:34 The Future of Education and Skills Training 37:26 The Role of AI in Enhancing Productivity 42:23 The Evolution of Entry-Level Jobs 46:35 The Need for Specialized Training Programs References in the Show: https://www.mgt.us/insights/top-5-k-12-enrollment-trends-for-2025/  https://trainual.com/ https://www.washingtontimes.com/news/2024/oct/8/report-finds-charter-school-enrollment-booming-whi/  Quote of the Show: “AI is really no different than hiring a new junior-level employee that you're going to delegate to so that you can take on the higher-level work in the business. So everybody that's working at these companies, if they're afraid of AI, it's because they have this scarcity mindset of just holding on to what they've always done. People will not be doing the same work 10 years from now that they've always done. It just won't make any economic sense.” - Chris Ronzio 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

    48 min

  4. JUN 20

    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 of modern education—and what it could all mean for the future of college, careers, and lifelong learning. Chapters 00:00 Introduction and Personal Updates 03:46 Transitioning to Open Education 05:42 Understanding Open Education and Its Mission 09:02 The Economics of Homeschooling 14:04 Funding and Support for Homeschooling 18:09 The Shift in Education Choices 21:38 The Future of Education and Trust in Institutions 24:10 Crisis in Education: Trust and Control 25:57 The Role of Socioeconomic Status in Homeschooling 27:45 The Benefits of Homeschooling: Flexibility and Customization 30:21 Innovative Learning Experiences Beyond Traditional Education 32:46 Community-Driven Learning: The Power of Shared Experiences 34:37 Empowering Parents: Taking Responsibility for Education 37:58 Navigating State Regulations in Education 41:31 The Future of College: A Shift in Educational Paradigms References in the Show: https://www.mgt.us/insights/top-5-k-12-enrollment-trends-for-2025/  https://www.pewresearch.org/short-reads/2025/02/20/a-look-at-homeschooling-in-the-us/  https://www.washingtontimes.com/news/2024/oct/8/report-finds-charter-school-enrollment-booming-whi/  https://opened.co/  Quote of the Show: “Trust is the new data. We do not trust institutions anymore as a country. If anyone pays attention to the news right now, it's like, I can't trust anyone on anything. We've been lied to so much and I'm not even naming anything. I'm not taking a political side as we don't trust institutions. Our institutions are in a mode of crisis and families are having to take more charge, more control of their kids.” - Jared Fuller 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

    42 min

  5. JUN 6

    Ageism, Curiosity, and Fist Bumps- Season 4: Episode # 66

    Join us for a lively conversation with Dan Tyre, one of HubSpot’s 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 company’s sales strategy evolved alongside a rapidly changing workforce.    From tackling ageism in tech to highlighting the value of curiosity, this episode explores what it takes to succeed in today’s job market. Dan shares practical tips on adaptability, preparation, and building strong relationships, offering a roadmap for anyone navigating career growth or startup life.  Chapters  02:59 The Journey of Dan Tyre at HubSpot  06:08 The Evolution of Work and AI  09:03 Building Relationships in Business  11:59 Creating Value for Startups  13:47 The Evolution of HubSpot's Sales Strategy  15:53 Ageism in the Workplace: A Personal Perspective  22:03 Building a Culture of Learning and Adaptability  30:06 The Importance of Curiosity and Business Acumen  34:15 The Power of Business Acumen in Sales  35:58 Curiosity and Learning in Sales  39:31 Identifying and Developing Sales Talent  42:55 Navigating the Future Workforce  46:02 The Importance of Preparation in Interviews  51:29 Closing Thoughts on Competitive Advantage  References in the Show:  https://www.entrepreneur.com/business-news/fiverr-ceo-says-ai-will-take-your-job-heres-what-to-do/491198    https://www.marketwatch.com/story/why-a-record-number-of-adults-over-65-are-working-and-its-not-just-about-money-85d2f15d?utm_source    https://www.marketwatch.com/story/why-a-record-number-of-adults-over-65-are-working-and-its-not-just-about-money-85d2f15d?utm_source    https://www.linkedin.com/pulse/experts-weigh-why-2025-holds-hope-older-workers-janine-vanderburg-tytkc/     Quote of the Show:  “Who needs a 66-year-old man telling them what to do, right? That's stupid. This is the modern age and you've got to be smart enough to say, alright, I know what this person needs and then ask the right question so you play inception, right?” - Dan Tyre    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

    52 min

  6. MAY 23

    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 today’s 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.  Chapters 00:00 Introduction   03:01 Starting a Business in the Age of AI 06:04 The Evolution of Arcadia 08:49 Operationalizing Partner Programs 10:16 Building Relationships Through Shared Experiences 11:01 Navigating the Partnership Landscape 12:39 The Evolution of Entrepreneurial Journeys 16:20 The Importance of Relationships in Partnerships 17:33 The Entrepreneurial Journey: From Idea to Execution 19:14 Setting Expectations in Partnerships 21:47 The Challenges of Fractional Leadership 23:32 The Role of Relationships in Business Success 25:37 Learning the Art of Relationship Building 30:50 The Future of Arcadia and Community Building 36:20 Curating Quality Connections 38:00 The Demand for Bespoke Experiences 44:58 Navigating the Future of Arcadia 51:01 Closing Thoughts and Future Directions References in the Show: https://www.forbes.com/sites/jodiecook/2025/02/25/how-to-be-an-entrepreneur-in-the-age-of-ai/  https://www.northone.com/blog/small-business/entrepreneur-statistics  https://www.gartner.com/en/articles/product-differentiation  https://hbr.org/2024/06/why-cofounder-partnerships-fail-and-how-to-make-them-last  https://mobidev.biz/blog/future-artificial-intelligence-technology-ai-trends  Quote of the Show: “Arcadia means harmony, and that's the idyllic version of natural splendor. We chose that name for the business because that's what the partner leaders should be trying to do, is establish harmony between their partners, between their internal sales leaders, their internal marketing leaders, et cetera. But on the flip side of that, what Sam and I look for is, how do we help individuals find that harmony in their life? How do we help them find that and bring that into the work that they do, the life that they live, and the pursuits that they take on? It's very important to us to help them find that whole self and that person within everything that they do.” - Jason Yarborough Ways to Tune In: Spotify: https://open.spotify.com/show/5GpM8myxsUinc5bfLIbjJz?si=0af576adfb8e49f8 Apple Podcasts: https://podcasts.apple.com/us/podcast/the-cheat-code/id1692445190 Amazon Music: https://music.amazon.com/podcasts/cb0b3afa-063f-4f3b-96be-b98214c74912 YouTube: https://www.youtube.com/@CheatCodePodcast

    46 min

  7. MAY 9

    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 Alignment 25:58 From Founder to CEO: The Evolution of Leadership 30:24 Assessing Self-Awareness in Founders 35:00 The Role of Honesty and Transparency in Leadership 39:38 Red Flags in Founder Narratives: The Importance of Realism References in the Show: https://startupnation.com/manage-your-business/the-9-types-of-startup-founders-and-how-to-build-a-great-co-founder-team/ https://hbr.org/2024/10/the-strengths-and-weaknesses-that-set-founders-apart  https://www.saastr.com/top-10-founder-gtm-mistakes-with-saastr-founder-and-ceo-jason-lemkin/  https://www.liveplan.com/blog/starting/traits-of-entrepreneurs?srsltid=AfmBOopgdo-3EvV8JQ5Y5CyDEoKlefYsv5gFfhCuTYA4sf6OaCO0YhgY  Quote of the Show: “I would say over a third of the times I've invested early in a co-founding relationship, the co-founder relationship blows up.” - Gregg Scoresby 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

    42 min

  8. APR 25

    Market Challenges, Bootstrapping, and Founder Expectations - Season 4: Episode # 63

    What’s 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 today’s 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 08:52 Characteristics of Practical Founders 11:53 Growth Strategies and Metrics 14:51 Evaluating Great Companies 18:04 The Role of Founders in Company Success 21:11 Navigating Between VC and Bootstrap Models 28:26 The Evolving Landscape of Venture Capital 31:45 Navigating Funding Models and Founder Expectations 36:33 Understanding the Dynamics of Syndicated Deals 39:44 The Role of AI in Modern Business Strategies 54:22 Finding the Right Fit: Aligning Founders and Funders References in the Show: https://www.saastr.com/carta-38-of-bootstrapped-start-ups-have-solo-founders-but-only-17-of-vc-backed-ones-do-and-10-12-of-ones-that-ipo/  https://therecursive.com/tally-bootstrapped-success/ https://practicalfounders.com/  Quote of the Show: “The practical founders I work with are adding AI incrementally and practically in useful ways into their product. They're not stopping everything, saying we're going to be AI-first. They're not just waving AI out there, but they're using it in their business to get more efficient, and faster. Then we're back to the choice of how fast do you want to grow and what do you want to do with those extra dollars?” - Greg Head  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

    52 min
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5
out of 5
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About

Serial entrepreneurs and operators Justin Gray, Josh Wagner & Sean Kester combine decades of B2B and GTM expertise with unwavering honesty to unpack the latest news (fake or otherwise) on The Cheat Code & Friends Podcast. Combined with a rotating guest list of founders, practitioners and investors, the no-nonsense forum gathers fortnightly, holding court to translate headlines into reality and discuss the impact for early-stage businesses. The Cheat Code is just that, the trusted folks we look to for advice and insight, and we hope to bring the same to you.

Information

  • Creator
    In Revenue Capital
  • Years Active
    2023 - 2025
  • Episodes
    70
  • Rating
    Clean
  • Copyright
    © 2023
  • Show Website
    The Cheat Code & Friends