The Entrepreneur's Logbook: Lessons from Growing Businesses
The Entrepreneur's Logbook: Lessons from Growing Businesses
Podcast Description
The Entrepreneur's Logbook brings you inside the minds of today's most successful business leaders to uncover the strategies, decisions, and frameworks driving extraordinary growth. Each episode features founders and CEOs sharing their proven approaches to scaling teams, expanding market share, and building thriving companies.
Our guests - from bootstrapped success stories to venture-backed innovators - break down the exact systems, processes, and strategies you can use to grow your company. No fluff, just actionable insights you can apply to your business.
Whether you're leading a growing team, aiming to break through revenue plateaus, or planning your next expansion, each episode delivers tested playbooks and practical wisdom from leaders who've turned small businesses into market leaders. Think of it as your masterclass in sustainable business growth.
Podcast Insights
Content Themes
The podcast covers a range of topics including effective leadership, scaling strategies, customer experience, HR technology, and professional branding. Episodes feature specific discussions such as the bias trifecta in leadership, utilizing AI for market insights, and strategies for transforming startups into market leaders, providing listeners with actionable insights applicable to their businesses.
The Entrepreneur’s Logbook brings you inside the minds of today’s most successful business leaders to uncover the strategies, decisions, and frameworks driving extraordinary growth. Each episode features founders and CEOs sharing their proven approaches to scaling teams, expanding market share, and building thriving companies.
Our guests – from bootstrapped success stories to venture-backed innovators – break down the exact systems, processes, and strategies you can use to grow your company. No fluff, just actionable insights you can apply to your business.
Whether you’re leading a growing team, aiming to break through revenue plateaus, or planning your next expansion, each episode delivers tested playbooks and practical wisdom from leaders who’ve turned small businesses into market leaders. Think of it as your masterclass in sustainable business growth.
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://www.linkedin.com/in/shoemoney/
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