Why Building With AI Got Easy and Maintaining It Got Brutal with Fathom CEO Richard White

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1. 

   S2 · E33 · 19 Aug 2026 · 47 min

   How a Near-Fatal Car Accident Made Guinness World Record Holder Jenn Drummond Stop Living for Everyone Else

   Jenn Drummond had no mountaineering experience, no tolerance for sleeping in tents, and a fear of heights she did not discover until she was ten feet off an indoor climbing wall during her first training session. Three years later, she became the first woman in history to complete the Seven Second Summits, standing on the second-highest peak on every continent and earning her place in the Guinness World Records as one of the most unlikely and most documented athletic achievements in modern history. Jenn Drummond is a Guinness World Record holder, entrepreneur, speaker, and mother of seven.…

2. 

   S2 · E32 · 12 Aug 2026 · 1 hr 14 min

   Why the Setter-Closer Model Still Wins (And How to Build One That Actually Scales)

   Josh Troy, co-founder of Curvion Blue and 12-year high-ticket sales operator, joins Kayvon Kay on to break down what a real sales operation looks like from the inside, and why most founders have never actually built one. Most sales problems are not sales problems. They are infrastructure problems dressed up as performance problems. You hired the wrong person, handed them the wrong metrics, and wondered why nothing scaled. Josh has seen it hundreds of times. So has Kayvon. This conversation is two operators comparing notes without cleaning it up for the audience. The episode opens on the…

3. 

   S2 · E31 · 5 Aug 2026 · 1 hr 22 min

   Inner Empire: Why Unfinished Tasks Are Quietly Draining Your Income

   Meir Ezra, entrepreneur, speaker, and founder of Guaranteed Prosperity, sits down with Kayvon Kay for part two of a three-part series called Inner Empire. Every task you have not finished is still running in the background of your mind. It is pulling your attention, your energy, and your money without you noticing. Meir names exactly what is happening inside your head when you stall, freeze, or half finish something, and exactly what it is costing you. This is not a mindset conversation. It is a mechanism, and once you see it, you cannot unsee it. The episode opens with a distinction most…

4. 

   S2 · E29 · 22 Jul 2026 · 47 min

   How Real Brands Build Trust and Consistency (Most Companies Miss This Entirely)

   Most businesses think branding is marketing. It's not. And that single confusion costs them millions in lost trust, positioning, and growth. Howard Lim has spent his career helping companies to build and rebuild their brands. He breaks down exactly where businesses get branding wrong, why consistency matters more than creativity, and how the brands people actually want to buy are built on systems, not slogans. If your business isn't printing the value you know it's worth, this is likely why. Branding isn't about what you say. It's about what people think about you. The gap between those two…

5. 

   S2 · E28 · 15 Jul 2026 · 42 min

   Why Talented People Fail and Tenacious People Don't (The U2 Roadie Who Proved It)

   A psychologist told Scott Scovill it would be easier for him to grab a red-hot stove and hang on than to try at anything. His fear of failure was that severe. It flunked him out of college and left him waiting tables at a roadside Howard Johnson's. Then a tour bus rolled in one day, and everything he believed about talent, fear, and what it takes to make it got dismantled. In this conversation, Kayvon pulls apart how a college dropout with a clinical fear of failure snuck into U2 shows for five weeks with a homemade laminate, lived in his car, worked for free, and landed on the biggest…

6. 

   S2 · E27 · 8 Jul 2026 · 30 min

   How to Get Your Business Recommended by ChatGPT, Claude and Other AI Search Tools

   Your customers stopped Googling. They ask ChatGPT now. And when ChatGPT answers, it recommends someone. If that someone is not you, this episode explains exactly why, and exactly what to do about it. One founder already cracked it: 10 million impressions from ChatGPT, zero dollars in ad spend, and an American Marketing Association campaign of the year award to prove it was not luck. Anya Cheng spent her career building products and marketing at Meta, eBay, Target, and McDonald's tech headquarters before founding Taelor, an AI-powered menswear rental company in Silicon Valley. She is a…

7. 

   S2 · E40 · 8 Oct 2026 · 42 min

   How AI is Raising the Bar at Every Job (Most People Haven't Felt It Yet)

   Your team is already being measured against a standard you didn't set. AI raised the bar, and the founders who haven't noticed are about to miss opportunities because of it. Kayvon sits down with Sean Campbell, who has spent three decades watching how people adopt technology, who embraces it and who stalls. Sean sees the pattern in his classroom, in boardrooms and in the companies he helps rebuild around AI. He gives Kayvon the one question he would ask to predict who wins with it, and it has nothing to do with how technical you are. It comes down to how you manage people. Sean is the CEO of…

8. 

   S2 · E39 · 1 Oct 2026 · 2 min

   How Nike Built the Stories Behind Kobe and LeBron (And What Every Brand Can Learn From It)

   Most people who stall out in their careers never find out why. They did the work and hit the numbers, then watched someone else get the room, the budget, and the title. The rules that decided it were never written down, and nobody was going to hand them over. Arturo Nunez is the former VP of Marketing for Nike Basketball, where he shaped the public stories of Kobe Bryant and LeBron James. He ran Latin America for the NBA, spent four and a half years at Apple, and served as CMO of the largest digital bank in the world. He grew up in 1970s Harlem with no one in his family who had ever worked…

9. 

   S2 · E38 · 23 Sep 2026 · 1 hr 4 min

   Why Emotional Energy Is the Real X-Factor in Scaling a Business (Not Strategy)

   Most founders think strategy is what separates the businesses that scale from the ones that stall. It isn't. Lee Benson built an aerospace maintenance company from zero to over 100 million dollars with no outside investors and sold it for a 21.6x EBITDA multiple, in an industry where an 8x is considered a strong exit. He says the real driver wasn't the strategy. It was something almost nobody tracks. Lee Benson is the founder of ETW, where he runs CEO mastermind groups and coaches roughly thirty CEOs at a time, and the founder of Dinner Table, a family value creation platform now serving…

10. 

    S2 · E37 · 16 Sep 2026 · 53 min

    How to Increase Your Website Conversion Rate (3 Free Fixes Anyone Can Make)

    Most businesses run their websites off of a feeling, pure gut instinct. A stock photo here, a red button there, a template because it "looked good." Sahil names that for what it is, then shows exactly what replaces it. Sahil Patel CEO of Spiralyze, built his career two SaaS companies deep, and by the time he became a customer of Spiralyze, he had already sat through enough failed website redesigns to know the truth nobody wants to hear. Your best guess about what converts is still just a guess. Four years later he now owns the company, and what he found by analyzing other people's live A/B…

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