The Entrepreneur's Logbook: Lessons from Growing Businesses

In this episode of the Entrepreneur’s Logbook Podcast, Zachary speaks with Jeremy Schoemaker, better known online as “ShoeMoney.” Jeremy first made his mark as one of the early internet marketing pioneers, co-founding Auction Ads (sold for $17 million) and Part Program (sold for $12 million), before quietly spending a decade building machine-learning trading systems. Today he’s a hands-on AI infrastructure engineer whose code has been merged into open-source projects at OpenAI, Google, Microsoft, Anthropic, Apple, Hugging Face and Mozilla. He’s also the author of over a million-copy-selling books, including “Nothing’s Changed but My Change: The ShoeMoney Story” and “AiBook: A Feel-Good Field Guide to Living and Working with AI Agents.” Zach and Jeremy kick off the conversation by reliving Jeremy’s hilariously bold first outreach: critiquing Zach’s mobile site as “ass” and then sending a complete site redesign in under 20 minutes. That playful anecdote sets the tone for a deep dive into how Jeremy approaches every project, identify a problem you personally need solved, build a minimal viable solution, give it away for free, and then monetize only once demand emerges. They explore strategies for building AI agents in incremental steps (the “Coke theory” of leveraging existing infrastructure), tips for keeping context without bloat, and the surprisingly simple trick of asking “What do I hate doing?” as the best way to uncover quick-win automation opportunities. Toward the end of the show, Jeremy and Zach discuss when it makes sense to rent AI infrastructure versus owning it outright, unpack misconceptions around enterprise privacy settings in ChatGPT, and debate which roles will never be replaced, namely, the real-world plumbers, electricians and technicians whose human touch remains irreplaceable. Listeners will walk away inspired to use AI as a force multiplier, but reminded that true competitive advantage still comes from authenticity, strong relationships and the personal brand you build around your work. Timestamps Jeremy’s Background in Early Internet Marketing and AI Engineering – 00:36 Unique Podcast Intro: Rebuilding the Host’s Mobile Site with AI – 02:02 “Listen to Everyone, but Don’t Blindly Follow Anyone” Advice – 05:10 Building Small AI MVPs, Offering for Free, Then Monetizing – 09:12 Automating Repetitive Tasks with Custom AI Agents (e.g., Comms Agent) – 13:56 Connect with Jeremy https://shoemoney.com/ https://www.linkedin.com/in/shoemoney/ https://shoemoney.com/#books Sponsored by We Feature You PR - Helping entrepreneurs build thought leadership through strategic podcast placements and launching their own shows. Ready to amplify your voice? Get in touch today. Subscribe & Review: If you enjoyed this episode, please subscribe and leave a review on your favorite podcast platform! Chapters (00:00:00) - Intro and Guest Introduction(00:01:34) - How Jeremy Rebuilt Their Website in 20 Minutes(00:04:43) - Lessons From Restarting a Career: Listen but Don't Follow(00:09:01) - Building for Value First, Monetizing Later(00:12:10) - Starting Small: The Coke Theory and AI Agents(00:18:28) - Terminal Life and Long History with Command Line Tools(00:20:48) - Separating AI Hype From Reality for Business Owners(00:28:23) - The Enduring Value of Human Touch in Services(00:32:44) - Owning vs Renting AI Infrastructure(00:38:45) - Enterprise Use Cases and Data Privacy(00:41:53) - Parting Advice: Avoid FOMO, Stay Human(00:47:36) - Closing Thoughts and Where to Find Jeremy

In this episode of The Entrepreneur’s Logbook, Zachary speaks with Carole Lawson and Rick Brown, co-founders of MarketStorm, an AI-driven advertising and demand-generation firm that helps brands reach customers long before they’re ready to buy. Rick and Carole share how they built MarketStorm from the ground up, never taking outside investment, and turned it into a nationwide operation by fusing Rick’s deep experience in sports and entertainment partnerships with Carole’s background in data science and behavioral research. Along the way, they explain why being physically together in those early years, asking hard questions of your own assumptions and partners, and moving faster on decisions are lessons they’d apply if they could start over today. The conversation digs into the “messy middle” of the buyer journey and how MarketStorm uses proprietary AI algorithms to target only those people beginning to think about a specific purchase, whether that’s a luxury home in Florida, an upscale wine collector in Oklahoma at 4 AM, or someone dreaming of private aviation. Rick and Carole contrast that precision “heat-seeking” approach with traditional last-click-only attribution models, which they argue have been obsolete for over a decade yet still dominate most agencies’ playbooks. They also debunk the hype around AI “for AI’s sake,” urging founders to begin with clear outcomes and metrics, then choose the right tools and data to support them. Listeners come away with practical advice on integrating AI meaningfully, avoiding waste in ad spend, and building trust across a long sales cycle by showing up in the right place at the right time, every time. Timestamps Lessons from founding MarketStorm – choosing speed, truthful planning, and co-locating early for better collaboration – 02:42 AI-driven demand strategy – how MarketStorm captures buyer intent and targets prospects before they’re actively shopping – 10:16 Pitfalls of last-click attribution – why focusing only on the final click overlooks 70%+ of the customer journey – 17:51 Genuine AI adoption vs. AI hype – the difference between purpose-built AI tools and simply slapping “AI” on existing processes – 21:23 Building trust in long sales cycles – leveraging intent and influence layers to nurture prospects over time – 26:38 Connect with Carole and Rick https://marketstorm.ai/ https://www.linkedin.com/in/caroleslawson/ https://www.linkedin.com/in/marketstormrick Sponsored by We Feature You PR - Helping entrepreneurs build thought leadership through strategic podcast placements and launching their own shows. Ready to amplify your voice? Get in touch today. Subscribe & Review: If you enjoyed this episode, please subscribe and leave a review on your favorite podcast platform! Chapters (00:00:00) - Intro and Guest Backgrounds(00:02:11) - Lessons Learned: What They'd Do Differently(00:05:01) - Building Together and Surviving COVID Timing(00:06:53) - How Marketstorm Finds Buyers Before They Search(00:10:28) - Beating Programmatic: The Secret Sauce(00:12:56) - Competitors and Protecting the IP(00:14:16) - The Problem with Last-Click Attribution(00:16:29) - Google's Own Research on Last-Click Myths(00:17:53) - Real AI Use vs Hype and Buzzwords(00:21:40) - Approaching AI Like Any Tech Implementation(00:22:47) - Earning Trust in Long Sales Cycles(00:24:16) - The $20,000 Wine Bottle Story(00:26:38) - Following Behavior, Not Guessing Placement(00:28:30) - Cutting Ad Waste and Winning the AI Search Race(00:30:10) - Final Advice: Question the Messy Middle(00:33:44) - Closing Thoughts and Where to Find Them

In this episode of The Entrepreneur’s Logbook, Zachary speaks with Mike Curtis, Chief Operating Officer of Traders Edge Network. Mike opens up about his introduction to the markets at just twelve years old and the first painful lesson he learned when an earnings event wiped out a trade. From that moment on, he shifted away from trying to predict every market move and toward designing rule-based, repeatable strategies that put risk management first. Today, he’s personally mentored hundreds of everyday investors, helping them replace guesswork with defined processes that generate consistent income through options rather than gambling on volatile swings. Zach and Mike dive into the heart of those risk-first approaches, from constructing simple covered-call and protective-put “insurance” positions to the signature weekly “Money Press” spread that aims to deliver small, reliable returns. They discuss how even modest accounts of just a few thousand dollars can get rolling, why setting clear milestones and carving out a half hour twice a week to learn the fundamentals makes all the difference, and how treating trading like any other skill, complete with study, practice, and accountability, helps investors stick with the plan. For anyone curious about getting started in options or looking to tighten up their risk controls, Mike’s blend of practical advice and mentoring insights makes this episode a must-listen. Timestamps Early introduction to trading and first lesson learned from a loss at age 12 – 00:18 Impact of the 2008 crash on adopting a risk-first, conservative strategy – 01:45 The emotional component of trading and why discipline beats impulse – 03:59 Traders Edge Network’s on-ramp process for new investors to place their first trades – 07:59 Structuring option spreads as “insurance” to define and limit downside risk – 11:32 Connect with Mike https://www.tradersedgenetwork.com/ https://www.linkedin.com/in/mike-c-curtis/ Sponsored by We Feature You PR - Helping entrepreneurs build thought leadership through strategic podcast placements and launching their own shows. Ready to amplify your voice? Get in touch today. Subscribe & Review: If you enjoyed this episode, please subscribe and leave a review on your favorite podcast platform! Chapters (00:00:00) - Introduction and guest background(00:01:29) - Mike's early trading experience and 2008 crash lessons(00:03:21) - Emotions and trading psychology(00:05:10) - Building a repeatable, risk-managed trading system(00:07:23) - Getting started: onboarding new traders(00:10:47) - Options vs. gambling: the insurance analogy(00:16:15) - What separates consistent traders from quitters(00:21:36) - Realistic time and money commitments to start trading(00:23:45) - Milestones, celebrations, and staying motivated(00:26:39) - Parting advice and where to learn more(00:29:31) - Closing remarks

In this episode of The Entrepreneur’s Logbook, Zachary speaks with Alberto Gimeno, co-founder and CEO of Invofox, a document-parsing and data-extraction API trusted by more than 150 companies across the U.S., Europe, and Latin America. A Spanish mathematician and computer scientist, Alberto spent nearly a decade building startups in Madrid before spotting the unstructured-data challenge while consulting for a client. Since launching Invofox in 2022 and graduating from Y Combinator’s Summer ’22 batch, he’s raised $11.5 million, moved the company’s headquarters to San Francisco, and overseen the processing of well over 100 million documents a year.  Zach and Alberto dig into one of the hardest lessons for any entrepreneur: focus. Drawing on missteps from previous ventures and early stumbles at Invofox, Alberto explains why saying “no” to easy revenue and adjacent opportunities is critical, especially when you’re building an initial product-market fit.  They discuss why a narrow, highly optimized roadmap wins over feature creep, how complexity and technical debt can spiral, and why founders should weigh the real cost of building and maintaining an in-house solution versus plugging in a specialized API. The conversation then shifts to the nuts and bolts of Invofox’s technology: how it blends traditional and layout-aware OCR, in-house machine-learning models, and the latest LLMs and VLMs into custom pipelines that balance accuracy, latency, reliability, and cost.  Alberto paints a clear picture of the build-versus-buy trade-off in document-heavy industries, mortgage, insurance, healthcare, and beyond, and debunks the Silicon Valley bubble around AI. He shares how most companies worldwide are only beginning to scratch the surface of AI’s potential and how Invofox can help them safely unlock automation at scale.  Timestamps Introduction to Alberto Jimeno and Invofox – 00:46 The importance of focus for startup success – 02:53 How Invofox’s API parses unstructured documents into usable data – 09:12 Build vs. buy: The hidden costs of in-house AI document solutions – 18:51 The AI adoption gap: Silicon Valley bubble vs. global reality – 27:41 Connect with Alberto https://www.invofox.com/en/ https://www.linkedin.com/in/gimenoalberto/ https://x.com/al_gimeno Sponsored by We Feature You PR - Helping entrepreneurs build thought leadership through strategic podcast placements and launching their own shows. Ready to amplify your voice? Get in touch today. Subscribe & Review: If you enjoyed this episode, please subscribe and leave a review on your favorite podcast platform! Chapters (00:00:00) - What's the Secret to AI's Success?(00:00:30) - The Entrepreneur's Logbook Podcast(00:01:38) - What's One Thing That I'd Do Differently As An Entreprene(00:08:20) - How We Optimized the Document Process with InvoFox(00:17:28) - Will Microsoft Build In House?(00:26:24) - Tim Ferriss: The Silicon Valley bubble on AI(00:32:26) - How to Reach Invo Fox

In this episode of The Entrepreneur’s Logbook, Zachary speaks with Steve Nolan, CEO of Ariel Group, a leadership-development and executive-coaching firm that helps some of the world’s best-known organizations build leaders who communicate with clarity and lead with real presence.  With more than 30 years of experience transforming companies from the inside, whether as CRO at The Myers-Briggs Company or guiding organizations through major acquisitions, Steve shares the principles he’s uncovered about what really drives long-term growth. Throughout their conversation, Zach and Steve break down why curiosity trumps assumptions, how to uncover the gap between what leaders think is broken and what truly needs fixing, and why behavior change must be managed as an ongoing system rather than a one-off event.  Steve delves into the often-overlooked power of asking better questions (“Do you know that, or do you think that?”) and explains how small “leaks” in customer retention, single-threaded relationships, untested assumptions, out-of-date pricing or simply neglecting to resell value, can quietly bleed revenue. He argues that no amount of new-customer acquisition will make up for the slow drain that goes unchecked.  From his work at Ariel Group, Steve shows how diagnostic rigor, akin to a doctor ruling out every possible cause of a chronic nosebleed, uncovers the root of organizational “symptoms” and brings teams back to higher performance. The conversation closes on the themes of culture and AI. Treating a company like a living organism, Steve emphasizes transparency, an unwavering focus on customer experience, and an open-door style of leadership that gives every employee a clear view of how their role connects to value creation.  And while AI promises powerful productivity gains, he underlines the need for a “human in the loop” design: leveraging technology to amplify judgment and accelerate learning, not to replace the essential conversations, accountability and trust-building that only people can deliver. Timestamps Embracing Curiosity and Challenging Assumptions – 02:24 Identifying Root Causes vs. Surface Symptoms in Leadership Challenges – 04:58 The Limitations of Financial Dashboards and the Need for Qualitative Context – 07:35 Tackling Revenue Leakage: Retention, Single-Threaded Relationships, and Pricing Gaps – 11:57 Achieving Lasting Behavior Change through Systems, Reinforcement, and a Human-in-the-Loop – 17:13 Connect with Steve https://www.arielgroup.com/ https://www.linkedin.com/in/nolansteven Sponsored by We Feature You PR - Helping entrepreneurs build thought leadership through strategic podcast placements and launching their own shows. Ready to amplify your voice? Get in touch today. Subscribe & Review: If you enjoyed this episode, please subscribe and leave a review on your favorite podcast platform! Chapters (00:00:00) - The Entrepreneur's Outcome Logbook(00:00:39) - Steve Nolan(00:01:57) - Career Reboot: Being Curious(00:04:29) - How to Fix a Company's Problems?(00:07:27) - Steve Crowell: The Numbers Don't Tell the Full Story(00:11:30) - Revenue leakage is an important issue for business growth(00:16:41) - How Do Leadership Training Programs Change Behavior?(00:20:29) - What is the Company Culture?(00:21:37) - Aerial Group's CEO on Company Culture(00:25:31) - The Living Organization(00:26:58) - Leadership Challenges in AI(00:32:19) - A message for Leaders on AI