AI, Creativity and Connection - Season 5: Episode #101

Everyone has access to AI tools. Everyone's automating outreach. And somehow, getting a prospect to actually respond hasn't gotten any easier.David Politis, founder of BetterCloud and creator of Not Another CEO, joins Justin, Josh and Sean to talk about what's working in GTM when everyone has access to the same technology.David has seen the cycle before, from the early days of Marketo and Salesloft to today's AI SDRs. The technology gives you an edge until everyone else starts using it. So where do you go from there? Apparently, sometimes the answer is a custom football jersey, a personalized demo, or even a petting zoo at a conference.The guys get into how AI can make prospect research dramatically easier, why buyers have less patience for traditional sales processes, and why creativity and emotional intelligence are becoming so important when hiring salespeople.There's a lot AI can do to help you sell. Getting someone to genuinely want to talk to you is still a different challenge.Chapters00:00 Introduction and episode overview02:01 The shift towards human involvement in AI-driven sales07:48 The cycle of technology adoption and differentiation11:19 Using AI for deep research and creative outreach15:20 The importance of genuine human interaction in sales20:21 Creative in-person experiences and high ROI events26:00 Building brand and thought leadership with AI30:15 Hiring for creativity, EQ, and resourcefulness36:23 The future of in-person events and relationship building44:31 Final thoughts and resources for further learningReferences in the Show:https://www.linkedin.com/company/not-another-ceo/ https://notanotherceo.substack.com/ Quote of the Show:“This is why early stage, and again, I'm talking about sub-10 million in ARR. I mean, all the way up to scale makes sense, but sub-10 million, I think the CEO, even if they hand off the actual sales process, there's so much value to them being involved, especially if they can build themselves a little brand in that particular space. Because part of the ‘give’ in the process may have nothing to do with the product. It may literally just be having a conversation with the CEO, who speaks to a hundred people in a similar situation as you, the buyer, every single week, and can come to the table with insight they couldn't otherwise get.” - David PolitisWays 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 

100 episodes. Three hosts. A few questionable party hats. The Cheat Code & Friends is celebrating its centennial. For this special episode, Justin, Josh and Sean ditch the guests and take a look back at the conversations, characters and unexpected lessons from the first 100 episodes. What started as a podcast about go-to-market cheats has turned into something more valuable, with some of the best conversations coming from people who challenged the guys to think differently.They revisit the guests who left a mark, from Dr. V challenging their perspectives on workplace culture to Jason Yarborough explaining why winning can hide serious problems. They get into the ideas that kept showing up across the years: why trust matters so much in GTM, what AI actually changes, how founders should think about capital, and why the best business advice is often painfully simple.There are plenty of shoutouts to old friends, a few stories from behind the scenes, and some appreciation for the people who've made the show worth showing up for every week.A hundred episodes in, the guys still don't have all the answers. But they've met some pretty interesting people along the way.Here's to 100 more.  Chapters 00:00 Introduction and milestone celebration01:59 Reflections on trust as a fundamental business driver04:00 Building a brand that fosters trust and authenticity06:00 The role of AI in exposing weaknesses and enabling scale08:00 Notable guests and their impactful insights09:56 Lessons on leadership, culture, and navigating challenges12:10 The importance of niche focus and authenticity in branding14:01 The trust hack and leveraging partnerships16:13 The evolving role of human judgment in the AI age18:08 Reflections on memorable episodes and guests20:07 Future outlook and closing thoughtsReferences in the Show:Jason Yarborough, Jared Fuller, Matt Heinz, Scott Albro, Geoff McQueen, Jason Vargas, Matthew Whyatt, Dr. V (Boykin), Dan Tyre, Brad Kotansky, Greg Head, Stacey Lewis, Kyle Lacy, Joe Chernov, Craig Coppola, Grant Siders, Katie Martell, Ted Purcell, Craig Rosenberg, Lauren Goldstein, Andrea Lechner-Becker, Chris Walker, Jay Po, Chris Walton, Max Altschuler, Kevin O'MalleyQuote of the Show:“Well, long story short, the takeaway from this is there's no shortage of great people that we've had the honor to speak with. I didn't think we'd do a hundred of these. Looking back on it and spending a little bit of time reflecting, maybe we'll do a hundred more, I don't know. I wouldn't mind it. As long as we can keep finding great, great folks, it's an enjoyable process and truly an honor.” - Justin GrayWays 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 

There's a big difference between having a great network and treating everyone you meet like they might be useful someday.Chris Walton, Founder and CEO of ATLAS, has built businesses across real estate and hospitality, and many of the biggest opportunities in his career have come through people he knows. But he isn't collecting contacts or building relationships around what someone might eventually do for him. His approach is almost the opposite: get to know interesting people, figure out what matters to them, help when you can and stay open to where it leads.Chris joins Justin, Josh and Sean to talk about what it looks like to be intentional about relationships without making them transactional. They get into building credibility, making introductions that create value for both sides, why asking for help can sometimes strengthen a relationship, and the patience required to let a network compound over years instead of trying to “activate” it when you need something.The bigger takeaway: relationships aren't something you “activate” when you need them. They're something you invest in over a lifetime, and the relationship itself has to be worth something regardless of what comes from it.Chapters00:00 Introduction and episode overview02:00 Chris Walton's background and entrepreneurial journey03:58 The significance of relationships as assets12:02 Strategies for authentic relationship building17:09 The importance of credibility and energy in networking21:59 Giving and helping others as a core principle27:54 Serendipity and creating opportunities through openness34:02 Long-term relationship focus and trust40:00 Crazy stories and unexpected outcomes from networking43:07 Final thoughts on relationship as a life and business assetReferences in the Show:https://www.atlasphx.com/  https://www.forbes.com/sites/rodgerdeanduncan/2025/12/13/why-deep-relationships-outperform-big-networks/ https://www.forbes.com/sites/williamarruda/2026/08/18/relationships-win-in-business-heres-how-to-build-them-in-the-ai-era/ Quote of the Show:“I had an epiphany maybe within the last year or two, and that is relationships are the single greatest asset in our life. Period. If you think about first principles, it is an outcome, like an intended potential outcome. That's kind of the tip of the spear for me. And it could come in a number of different forms.” - Chris WaltonWays 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 

AI can have all the right data and context. That doesn't mean it knows what good looks like.What's missing is taste.Jason Vargas, Co-Founder & Chief Partner Officer at RevShoppe, describes it as the judgment that comes from experience: knowing what good looks like, recognizing when a message will resonate, and being willing to challenge an AI-generated answer instead of accepting it at face value. As companies build AI deeper into their go-to-market motions, Jason believes capturing that judgment may become one of their biggest advantages.Jason joins Sean, Justin and Josh to discuss how companies can actually build a taste layer, who should be responsible for it, and why it needs to evolve alongside the people, buyers and business itself. They also explore what AI means for traditional GTM team structures, how organizations can train agents more like employees, and why scaling AI successfully still requires humans who know what good looks like.Chapters00:00 Introduction to the taste layer in AI01:56 The importance of judgment in AI systems04:00 How organizations can build their taste layer07:59 The role of human judgment and experience12:01 Challenges in developing the taste layer15:48 Organizational structure and AI responsibility19:49 Onboarding and evolving the taste layer24:00 Digital twins and AI in organizational context27:57 Success stories and examples of taste layer implementation32:05 Future opportunities and closing thoughtsReferences in the Show:https://councils.forbes.com/blog/ai-is-cool-but-2026s-most-valuable-marketing-asset-is-still-human-taste https://hbr.org/2026/08/ai-is-undermining-leaders-judgment-heres-what-to-do-about-it Quote of the Show:“You have to be able to push back on [AI] and to bring your judgment into whatever it brings back. You have to bring your experience of building companies, running teams, coaching people, whatever. You have to bring that into the conversation with it, and you have to be able to spar with it. That helps you build the judgment. That's what I'm doing personally, and it helps. But you can't take what it brings back to you at face value. You always have to challenge, like, ‘Where'd you find that? Show me a link, or why did you say that?’” - Jason VargasWays 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 

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 

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 

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 

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 

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 

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