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

Connect with Jeremy

https://shoemoney.com/

https://www.linkedin.com/in/shoemoney/

https://shoemoney.com/#books

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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

Connect with Carole and Rick

https://marketstorm.ai/

https://www.linkedin.com/in/caroleslawson/

https://www.linkedin.com/in/marketstormrick

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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

Connect with Mike

https://www.tradersedgenetwork.com/

https://www.linkedin.com/in/mike-c-curtis/

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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

Connect with Alberto

https://www.invofox.com/en/

https://www.linkedin.com/in/gimenoalberto/

https://x.com/al_gimeno

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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

Connect with Steve

https://www.arielgroup.com/

https://www.linkedin.com/in/nolansteven

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In this episode of The Entrepreneur’s Logbook, Zachary speaks with Brooke MacLean, CEO of Marketwake, an Atlanta-based growth marketing agency that marries data and creative storytelling. 

Brooke shares how she scaled Marketwake to nearly 80 employees, landed on the Inc. 5000 list six times, and earned a spot on Inc.’s Best Places to Work for five consecutive years. She also reflects on her early leadership crash course as CEO of an email automation startup at 26 and her current passion for backing founders through Marketwake Ventures. 

Together, Zachary and Brooke dive into the messy, childlike exploration every entrepreneur must embrace, why getting your legal foundations right from day one matters more than perfecting your branding, and how teaching your team to think for themselves builds true leaders. They tackle marketing strategy in uncertain times and explain why cutting ad spend can undermine both your growth and your brand’s perceived health. 

You’ll hear Brooke’s unconventional take on keeping marketing alive during downturns, plus her vivid anecdotes about annual company retreats (think Iceland, Belize, maybe not Big Sky skiing). The conversation wraps with a deep look at culture as the ultimate growth flywheel. Brooke explains Marketwake’s transparent, profit-sharing model and her “debate room” approach to adopting AI, ensuring human judgment remains central to every decision. 

From avoiding copy-and-paste marketing traps to reclaiming your brand’s soul in an AI-driven world, this episode is packed with practical lessons for founders, marketers, and leaders looking to scale without losing what makes their company unique.

Timestamps

Connect with Brooke

https://www.marketwake.com/

https://www.linkedin.com/in/brookebmaclean/

https://www.instagram.com/brookebmaclean

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In this episode of The Entrepreneur’s Logbook, Zachary speaks with Zenon Olbrys, CEO of Microf, a company that helps homeowners finance essential HVAC and water-heater replacements through a flexible lease-to-own program when traditional lenders turn them away. 

Zenon’s path to Microf is anything but conventional: after 17 years leading companies through the chaos of post-communist Central and Eastern Europe, he spent time in the trenches as a home-improvement contractor in the U.S. Those experiences taught him the power of pairing talented people with the right technology, and the courage to overhaul systems early on. 

Zenon explains how alternative data models and a secured lease-ownership structure let Microf approve up to three-quarters of applicants, keep rates reasonable, and manage risk. He also makes the case for “good friction”, a few extra minutes of human hand-holding that boosts conversions, clarifies lease-to-own terms, and strengthens customer relationships. As HVAC prices soar and consumers tighten their belts, Zach and Zenon explore why contractors must lead with monthly payments rather than sticker prices, pivot toward repairs and maintenance, and embrace adaptability. 

Finally, Zenon leaves home-service entrepreneurs with a rallying cry: trades are more critical than ever, technology can’t wait, and focusing on what customers truly need will see you through any economic cycle.

Timestamps

Connect with Zenon

https://microf.com/

https://www.linkedin.com/in/zenon-olbrys-6102b644/

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In this episode of The Entrepreneur’s Logbook, Zachary speaks with Rich Kahn, CEO and co-founder of Anura.io, the leading ad-fraud detection platform that uncovers bots, malware, and fake clicks siphoning off marketing budgets. 

Rich traces his entrepreneurial roots back to writing his first video game at age nine and publishing it by twelve. After decades of bootstrapping multiple web ventures and watching ad fraud quietly erode campaign performance, he launched Anura.io to give marketers a real-time window into the true quality of their traffic. Along the way, they discuss his switch from self-funding to considering outside capital, the pros and cons of each approach, and the value investors can bring beyond dollars. 

Zach and Rich then dive deep into what ad fraud looks like today, from bots that spoof residential IP addresses to human-run fraud farms slipping past traditional filters. Listeners learn how fraud quietly drains as much as 40 percent or more of ad spend, why false positives in many solutions can scare off genuine customers, and how Anura.io’s data-driven, third-party architecture delivers 99.999 percent accuracy with a written guarantee. 

Rich closes with practical advice for anyone running digital ads: get a free Traffic Quality Audit at Anura.io to see exactly how much fraud is nibbling at your budget, and start putting those reclaimed dollars back into campaigns that really convert.

Timestamps

Connect with Rich

https://www.anura.io

https://www.linkedin.com/in/richkahn/

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In this episode of The Entrepreneur’s Logbook, Zachary speaks with Loral Langemeier, CEO and founder of Live Out Loud, about her two-decade journey as “the Millionaire Maker.” Together they explore why wealth isn’t a one-off windfall but a repeatable cycle of building income-generating assets, reinforcing your tax and corporate foundations, and then reinvesting those gains for lasting growth.

Loral shares her advice on what she would do differently if she could start over, namely, begin earlier, assemble a team faster, and treat building wealth with the same urgency most reserve for their day jobs. Zach and Loral dig into the nuts and bolts of her gap-analysis framework, explaining how to assess “lazy” assets (like underperforming retirement accounts or real estate), create rules for cash flow, and generate “fast-cash” wins that build confidence and momentum.

They also debunk the myth of passive income, rebranding it “p-active” to highlight the ongoing effort required to keep money moving. Along the way, Loral stresses the danger of fragmented financial advice and makes the case for an integrated team of experts—tax strategists, estate lawyers, real-estate professionals, and more, who coordinate around your goals.

Listeners will come away with practical steps for locking in tax savings as a “profit center,” jump-starting new income streams with simple outreach, and mastering the mindset and habits that separate those who build real wealth from those who stay stuck.

Timestamps
1. Restarting Your Wealth Journey: Start Earlier and Build Your Team Faster – 00:02:06
2. The Wealth-Building Process: Gap Analysis, Income Generation, Asset Cycle & Tax Foundations – 00:04:02
3. Debunking the Passive-Income Myth: Introducing “Pactive” Income – 00:05:51
4. Integrated Wealth Systems: Why Holistic Tax Strategy and Team Coordination Matter – 00:09:02
5. The Power of Knowledge, Mindset & Urgency in Creating Lasting Wealth – 00:23:10

Connect with Loral

Website: askloral.com/logbook

LinkedIn: https://www.linkedin.com/in/lorallangemeier

Check out Loral's book: https://a.co/d/0dxPyNVJ

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In this episode of The Entrepreneur’s Logbook, Zachary speaks with Steve Carver, product development director and master trainer at Jump Sport. Zach and Steve kick things off by exploring Steve’s unlikely journey from gym front-desk clerk to “Mr. Bouncer,” a fitness celebrity who has championed rebounding for more than three decades. 

Along the way, Steve shares the biggest lesson he’d tell his younger self, choose work you love over money alone, and explains how defining your “why,” committing fully, and crafting a realistic plan can help anyone break out of a fitness or career rut. Listeners will appreciate Steve’s candid advice on staying present, giving 100 percent of whatever you have each day, and treating every goal, no matter how small, as the first step on the path to lasting success. 

The conversation then pivots to the power of rebounding on a Jump Sport trampoline, where Steve debunks common myths and highlights the science behind low-impact, high-intensity movement. He details research showing that just 12 minutes of trampolining can burn as many calories as 20 minutes on a treadmill, all while reducing ground impact by up to 80 percent and engaging more muscle groups in three-dimensional space. 

Beyond fitness, Steve explains how gentle bouncing helps regulate stress, boost mood-lifting hormones, and speed recovery by stimulating lymph flow. He also introduces Liquid Hydrogen, Jump Sport’s molecular hydrogen electrolyte drink, as a cutting-edge tool for reducing oxidative stress, supporting mitochondrial health, and promoting faster post-workout recovery. Whether you’re a seasoned athlete or a busy professional looking for a fun way to stay active, this episode offers fresh insights, practical tips, and plenty of inspiration to get moving, trampoline or not.

Timestamps

Connect with Steve

https://www.jumpsport.com/

https://www.linkedin.com/in/steve-carver-95133841/

https://www.instagram.com/carvercompletefitness/

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