My Worst Investment Ever Podcast

David Siegel – A Smart Idea Nobody Wanted

BIO: David Siegel is a Silicon Valley entrepreneur who has founded more than a dozen companies. He has written five books on technology and business, was once a candidate for the dean of Stanford Business School, and is now an AI thought leader leading an AI startup he hopes will pave the way for the agentic economy. STORY: David invested heavily in launching a longevity coaching business, believing people would pay to extend their lives through lifestyle change. Despite strong science, personal results, and significant marketing spend, demand proved nearly nonexistent. LEARNING: A great idea without real demand is still a bad investment. > “There will be many new problems, and whenever there are new problems, there’s a new economic opportunity for many people.” > David Siegel GUEST PROFILE David Siegel [https://www.linkedin.com/in/david-siegel-9786582a7/] is a Silicon Valley entrepreneur who has founded more than a dozen companies. He has written five books on technology and business, was once a candidate for the dean of Stanford Business School, and is now an AI thought leader leading an AI startup he hopes will pave the way for the agentic economy. WORST INVESTMENT EVER After years of building companies and studying major technological shifts, David found himself pulled deeply into the longevity movement. This wasn’t casual curiosity. He read more than 20 books, radically transformed his lifestyle, and developed a deep understanding of insulin resistance, nutrition, exercise, and long-term health. The results were personal and visible. David was fit, disciplined, and energized. The idea that science could help people live 10 to 15 years longer, with a higher quality of life, felt not only possible but urgent. Helping others do the same seemed like a natural next chapter. TURNING PASSION INTO A BUSINESS Confident in both the science and his own experience, David decided to turn longevity coaching into a scalable business. His target audience was people in their 50s and 60s, individuals who were pre-diabetic or heading toward serious health issues and stood to benefit the most from early intervention. He approached the venture like a seasoned entrepreneur. He built funnels, ran Facebook ads, spoke at retirement communities, and spent months on discovery calls explaining how lifestyle changes could dramatically reduce the risk of cancer, Alzheimer’s, and diabetes. This wasn’t guesswork; it was disciplined execution. THE PAINFUL REALITY CHECK Then reality set in. Despite spending over $100,000 on advertising and investing countless hours in conversations, demand was almost nonexistent. People listened. They nodded. They agreed the logic made sense. Then they walked away. Many believed the healthcare system would save them. Others hoped for a pill instead of discipline. Even those clearly facing insulin resistance weren’t willing to make sustained lifestyle changes. The most sobering realization wasn’t about marketing or pricing. It was this: most people don’t actually want to live longer if it requires consistent effort. ACCEPTING THE LOSS In the end, only about one percent of the people David spoke to were already doing the work and didn’t need coaching. Everyone else opted out, fully aware of the consequences. The investment failed not because the science was wrong, but because the market wasn’t there. David ultimately gave the information away for free and walked away from the business, having learned an expensive but clarifying lesson about belief versus demand. LESSONS LEARNED 1. Even the most compelling solution will fail if it requires behavior that people are unwilling to change. 2. Logic, evidence, and outcomes don’t matter if the market emotionally resists effort. 3. A great idea without real demand is still a bad investment. ANDREW’S TAKEAWAYS 1. Andrew highlights that people consistently search for shortcuts rather than long-term solutions. Whether in health or investing, most people prefer convenience over discipline, even when the stakes are life-altering. ACTIONABLE ADVICE Before scaling any idea, test for real demand, not polite interest. Ask whether people are willing to pay, change their habits, and put in effort. If behavior change is central to your offering, validate that reality early or risk learning the hard way. DAVID’S RECOMMENDATIONS David encourages understanding your own health data, particularly insulin resistance, through proper testing, such as an oral glucose tolerance test. While the business failed, the knowledge remains powerful and freely available for those willing to act. PARTING WORDS > “Keep looking for new problems that didn’t exist six months ago and jump in after them.” > David Siegel [spp-transcript] CONNECT WITH DAVID SIEGEL 1. LinkedIn [https://www.linkedin.com/in/david-siegel-9786582a7/] 2. X [https://x.com/PullNews] 3. YouTube [https://www.youtube.com/@redshiftlabsonyoutube] 4. Website [https://www.redshiftlabs.io/reset] ANDREW’S BOOKS 1. How to Start Building Your Wealth Investing in the Stock Market [https://amzn.to/3qrfHjX] 2. My Worst Investment Ever [https://amzn.to/2PDApAo] 3. 9 Valuation Mistakes and How to Avoid Them [https://amzn.to/3v6ip1Y] 4. Transform Your Business with Dr.Deming’s 14 Points [https://amzn.to/3emBO8M] ANDREW’S ONLINE PROGRAMS 1. Valuation Master Class [https://valuationmasterclass.com/] 2. The Become a Better Investor Community [https://astotz.kartra.com/page/become-a-better-investor-community] 3. How to Start Building Your Wealth Investing in the Stock Market [https://academy.astotz.com/courses/how-to-start-building-your-wealth-investing-in-the-stock-market] 4. Finance Made Ridiculously Simple [https://academy.astotz.com/courses/finance-made-ridiculously-simple] 5. FVMR Investing: Quantamental Investing Across the World [https://academy.astotz.com/courses/fvmr-investing-quantamental-investing-across-the-world] 6. Become a Great Presenter and Increase Your Influence [https://academy.astotz.com/courses/gp] 7. Transform Your Business with Dr. Deming’s 14 Points [https://academy.astotz.com/courses/transformyourbusiness] 8. Achieve Your Goals [https://academy.astotz.com/courses/achieve-your-goals] CONNECT WITH ANDREW STOTZ: 1. astotz.com [https://www.astotz.com/] 2. LinkedIn [https://www.linkedin.com/in/andrewstotz/] 3. Facebook [https://www.facebook.com/andrewstotzpage] 4. Instagram [https://www.instagram.com/andstotz/] 5. Threads [https://www.threads.net/@andstotz] 6. X [https://twitter.com/Andrew_Stotz] 7. YouTube [https://www.youtube.com/c/andrewstotzpage] 8. My Worst Investment Ever Podcast [https://itunes.apple.com/us/podcast/my-worst-investment-ever-podcast/id1416554991?mt=2]

Jon Ostenson – I Built a Million-Dollar Business That Never Made a Profit

BIO: Jon is the Founder and CEO of FranBridge Consulting, a 2-time Inc. 5000 company, and he is a top 1% franchise consultant. STORY: Jon co-founded a marketing and call-center business that appeared successful on the surface, growing to millions in revenue and dozens of employees. However, excessive customization and an inability to charge prices that matched rising costs meant the business never became sustainably profitable. LEARNING: Profitability is oxygen. Knowing when to admit you’re wrong matters just as much as knowing how to start. > “Humble yourself and admit when you’re wrong, course correct, and pivot.” > Jon Ostenson GUEST PROFILE Jon Ostenson [https://www.linkedin.com/in/jonostenson/] is the Founder and CEO of FranBridge Consulting [https://franbridgeconsulting.com/], a 2-time Inc. 5000 company, and he is a top 1% franchise consultant. Jon is also the author of the bestselling book, Non-Food Franchising [https://franbridgeconsulting.com/#contact]. Jon draws on his experience as a former Inc. 500 Franchise President and Multi-Brand Franchisee in helping his clients select their franchise investments. WORST INVESTMENT EVER Leaving the corporate world felt like freedom. After years of structure, predictability, and steady paychecks, you finally get to build something of your own. That was precisely where Jon found himself: grateful for his corporate experience, energized by the idea of business ownership, and eager to prove he could create something meaningful on his own terms. A PROMISING PARTNERSHIP AND A COMPELLING BUSINESS VISION Shortly after leaving corporate life, Jon partnered with a colleague to launch a marketing and sales company. He owned 60 percent of the business and ran day-to-day operations, while his partner held the remaining 40 percent. The vision was compelling. The company would help franchise businesses grow by handling their marketing, answering inbound calls through an in-house call center, and booking appointments directly for clients. The promise was simple: make the phones ring and convert those calls into revenue. EARLY MOMENTUM AND THE ILLUSION OF SUCCESS At first, it worked. The business grew quickly, attracting a strong leadership team and building a culture Jon was proud of. With around 35 employees and annual revenues of $3 million to $4 million, the company appeared successful from the outside. The team was energized, clients were signing on, and the pace was exciting. WHEN GROWTH DIDN’T TRANSLATE INTO PROFIT But beneath the surface, there was a quiet, persistent problem. The business wasn’t profitable. Despite all the effort, the long hours, and the constant tweaking, the company hovered around breakeven. Some months it lost money. Others it barely scraped by. Payroll was always looming, and profitability felt just out of reach. Jon tried adjusting pricing, shifting emphasis between marketing and call center services, and introducing new technology to increase value. But every fix only delayed the inevitable question he didn’t want to answer: What if the model itself was broken? THE HIDDEN COST OF CUSTOMIZATION AND COMPLEXITY The core issue turned out to be customization. The business was designed to scale by serving franchise systems with repeatable processes. Instead, each franchisee insisted their market was different, their staff was unique, and their customers required special handling. Wanting to please early clients and drive revenue, Jon said yes. Again and again. Over time, the company became highly customized, operationally complex, and increasingly expensive to run. Pricing no longer matched costs. The more the business grew, the harder it became to make money. What looked like top-line success was masking a model that couldn’t sustain itself. THE HARD DECISION TO WALK AWAY WITH INTEGRITY Eventually, Jon made the difficult decision to wind down the business. There was no dramatic exit or acquisition, but there was integrity. The team helped place employees in new roles and transitioned clients responsibly. Still, it was a painful experience. The failure wasn’t just financial; it was an ego hit. This was Jon’s first true experience of business ownership, and letting it go meant admitting that the original idea wasn’t as strong as he believed. LESSONS LEARNED 1. The biggest lesson came from contrast. After running his own startup without a proven product-market fit, Jon developed a deep appreciation for franchising. Unlike a startup built on assumptions, franchises offer historical data, real performance benchmarks, and access to owners who have already walked the path. You can see results before you ever invest. 2. There were personal lessons, too. Knowing when to admit you’re wrong matters just as much as knowing how to start. Humility, course correction, and the willingness to pivot are not weaknesses in entrepreneurship; they’re survival skills. 3. Profitability, Jon learned, is oxygen. A business that can’t consistently operate in the black eventually suffocates, no matter how exciting the vision or how talented the team. ANDREW’S TAKEAWAYS 1. One of the most important disciplines for any business owner is accurately closing the books each month. That means reviewing not just the profit and loss statement, but also the balance sheet. If your accountant can’t do that, it’s time for a new one. Monthly financial clarity allows you to identify problems early, before they become fatal. 2. Another insight comes from scale. Based on analysis of tens of thousands of companies globally, Andrew points to $7.5 million in annual revenue as a critical threshold. Below that level, it’s tough to afford the management talent and infrastructure required to run a scalable business. If you can’t get there efficiently, it may be time to rethink the model. 3. Finally, complexity is the silent killer. Businesses naturally drift toward offering more products, more services, and more custom solutions. Every added layer increases costs and erodes margins. Only disciplined leadership can stop complexity from overwhelming profitability. ACTIONABLE ADVICE If you’re building a business, be honest about whether you’re chasing revenue or building something scalable. Early customization can help you survive, but staying there too long can trap you in a low-margin cycle that’s hard to escape. Focus on creating profitable top-line growth, not just growth for its own sake. Learn to say no, even when opportunities feel exciting. And remember: there is no perfect time to start a business. The best way to learn is to get in the game early, without betting everything, and build experience that you can compound over time. JON’S RECOMMENDATIONS Jon recommends starting with education and proven frameworks. He offers a free downloadable copy of his book, Non-Food Franchising [https://franbridgeconsulting.com/#contact], in a concise 90-page guide. The book has received strong feedback and provides practical insights for anyone considering business ownership. Listeners can download the PDF or audio version by visiting FranBridgeConsulting.com [http://franbridgeconsulting.com] and sharing their email address. Those who prefer a physical copy can purchase it on Amazon [https://amzn.to/4pIDrzE], with all proceeds supporting Hope International. NO.1 GOAL FOR THE NEXT 12 MONTHS Jon’s goal for the next 12 months is to grow passive income across multiple asset classes, including franchising. His goal is to build sustainable revenue streams that create freedom across all areas of life: faith, family, fitness, finances, and future ventures. Passive income, for Jon, isn’t just about money. It’s about capacity—the ability to choose how you spend your time and energy. PARTING WORDS > “There’s never a good time to start a business. Get off the couch, dip your toe in the water, read our book, get in the game, and start thinking about it.” > Jon Ostenson [spp-transcript] CONNECT WITH JON OSTENSON 1. LinkedIn [https://www.linkedin.com/in/jonostenson/] 2. Twitter [https://x.com/Jon_Ostenson] 3. Facebook [https://www.facebook.com/JonOstenson1/] 4. YouTube [https://www.youtube.com/@JonOstensonFBC] 5. Book [https://amzn.to/4pIDrzE] 6. Website [https://franbridgeconsulting.com/] ANDREW’S BOOKS 1. How to Start Building Your Wealth Investing in the Stock Market [https://amzn.to/3qrfHjX] 2. My Worst Investment Ever [https://amzn.to/2PDApAo] 3. 9 Valuation Mistakes and How to Avoid Them [https://amzn.to/3v6ip1Y] 4. Transform Your Business with Dr.Deming’s 14 Points [https://amzn.to/3emBO8M] ANDREW’S ONLINE PROGRAMS 1. Valuation Master Class [https://valuationmasterclass.com/] 2. The Become a Better Investor Community [https://astotz.kartra.com/page/become-a-better-investor-community] 3. How to Start Building Your Wealth Investing in the Stock Market [https://academy.astotz.com/courses/how-to-start-building-your-wealth-investing-in-the-stock-market] 4. Finance Made Ridiculously Simple [https://academy.astotz.com/courses/finance-made-ridiculously-simple] 5. FVMR Investing: Quantamental Investing Across the World [https://academy.astotz.com/courses/fvmr-investing-quantamental-investing-across-the-world] 6. Become a Great Presenter and Increase Your Influence [https://academy.astotz.com/courses/gp] 7. Transform Your Business with Dr. Deming’s 14 Points [https://academy.astotz.com/courses/transformyourbusiness] 8. Achieve Your Goals [https://academy.astotz.com/courses/achieve-your-goals] CONNECT WITH ANDREW STOTZ: 1. astotz.com [https://www.astotz.com/] 2. LinkedIn [https://www.linkedin.com/in/andrewstotz/] 3. Facebook [https://www.facebook.com/andrewstotzpage] 4. Instagram [https://www.instagram.com/andstotz/] 5. Threads [https://www.threads.net/@andstotz] 6. X [https://twitter.com/Andrew_Stotz] 7. YouTube [https://www.youtube.com/c/andrewstotzpage] 8. My Worst Investment Ever Podcast [https://itunes.apple.com/us/podcast/my-worst-investment-ever-podcast/id1416554991?mt=2]

Edwin Endlich – Early Doesn't Always Mean Right

BIO: Edwin Endlich is the Chief Marketing Officer of Wysh and President of the National Alliance for Financial Literacy and Inclusion. STORY: Edwin’s worst investment was buying Tilray stock at $143 during the early hype of legal cannabis investing. Swept up in the excitement of a “new frontier,” he held on as the price crashed—eventually selling at around 30 cents and losing over 99% of his investment. LEARNING: The fundamentals always apply, even in new or exciting industries. Don’t let hype replace due diligence.   > “We’re in this AI conversation, let’s not forget the fundamentals of the market. Learn from what has happened in this space before. And don’t get too cocky.” > Edwin Endlich   GUEST PROFILE Edwin Endlich [https://www.linkedin.com/in/edwinendlich/] is the Chief Marketing Officer of Wysh [https://www.wysh.com/] and President of the National Alliance for Financial Literacy and Inclusion [https://www.nafli.org/]. Edwin has spent his career at the intersection of marketing, fintech, and AI, helping financial institutions tell more human stories in an increasingly digital world. He’s passionate about making financial protection simple, accessible, and even a little more fun — proving you don’t need buzzwords or hype to make banking and technology relevant. WORST INVESTMENT EVER There’s nothing quite like the rush of feeling early—early to a trend, early to a movement, early to a once-in-a-lifetime opportunity. That’s precisely what Edwin felt in 2015–2016, when investing in legal cannabis became possible in parts of the United States. For the first time, regular people could invest in a newly legalized industry. It felt like history happening in real time, a frontier market ready to explode. Edwin and his friends didn’t want to miss out, especially when companies were going public, and their share prices seemed destined to skyrocket. One of those stocks was Tilray. At $143 a share, Edwin was convinced he was buying the future. He imagined stock splits, booming demand, and a cannabis empire rising from the ground floor. Instead, he watched that $143 tumble month after month, until he finally sold it for around 30 cents. The emotional rollercoaster of hope, disappointment, and finally acceptance was a journey Edwin will never forget. A 99.3% loss. He now calls it his worst investment—not just because of the financial hit, but because of how powerfully excitement and hype clouded his judgment. LESSONS LEARNED * Every investor thinks their situation is unique. But in reality, the same patterns repeat again and again. * Markets take time to mature. * Regulation can shift overnight. * Early doesn’t always mean right. * Excitement is not a strategy. ANDREW’S TAKEAWAYS * A portfolio isn’t just about diversification by industry or geography; it’s also about diversifying across stages of maturity. * Stable, well-regulated companies like Coca-Cola or Pepsi behave very differently from early-stage, hype-driven industries, such as the cannabis sector. * Even large companies, with teams of top analysts, often get it wrong. ACTIONABLE ADVICE If Edwin could offer one piece of advice to anyone starry-eyed over the next big thing, it would be this: Do your due diligence. Seriously. Before you invest in anything—especially something exciting, futuristic, or rapidly trending—slow down and ask: * Has this been done before? * What can I learn from past bubbles? * What does history say about similar innovations? * Am I investing in fundamentals—or feelings? Whether it’s cannabis in 2016 or AI in 2024, the pattern is the same. Booms become bubbles. Investors overestimate how fast an industry will mature. And emotion often wins over discipline. But with the right mindset and discipline, you can avoid these pitfalls. EDWIN’S RECOMMENDATIONS Edwin encourages people to empower themselves with real financial knowledge. That’s why he co-founded the National Alliance for Financial Literacy and Inclusion (NAFLI) [https://www.nafli.org/]—a nonprofit dedicated to helping individuals understand money, investing, and financial products. Whether you’re new to investing or leading a financial institution, NAFLI offers education, tools, and resources to help individuals make more informed financial decisions. NO.1 GOAL FOR THE NEXT 12 MONTHS Edwin’s goal for the next 12 months is to have a full, uninterrupted conversation with his daughter, one that lasts longer than 10 minutes and isn’t broken by phones, notifications, or distractions. Edwin wants to rebuild community and presence—starting at home. PARTING WORDS   > “Stay focused and look to the past.” > Edwin Endlich   [spp-transcript]   CONNECT WITH EDWIN ENDLICH * LinkedIn [https://www.linkedin.com/in/edwinendlich/] * Website [https://www.wysh.com/] ANDREW’S BOOKS * How to Start Building Your Wealth Investing in the Stock Market [https://amzn.to/3qrfHjX] * My Worst Investment Ever [https://amzn.to/2PDApAo] * 9 Valuation Mistakes and How to Avoid Them [https://amzn.to/3v6ip1Y] * Transform Your Business with Dr.Deming’s 14 Points [https://amzn.to/3emBO8M] ANDREW’S ONLINE PROGRAMS * Valuation Master Class [https://valuationmasterclass.com/] * The Become a Better Investor Community [https://astotz.kartra.com/page/become-a-better-investor-community] * How to Start Building Your Wealth Investing in the Stock Market [https://academy.astotz.com/courses/how-to-start-building-your-wealth-investing-in-the-stock-market] * Finance Made Ridiculously Simple [https://academy.astotz.com/courses/finance-made-ridiculously-simple] * FVMR Investing: Quantamental Investing Across the World [https://academy.astotz.com/courses/fvmr-investing-quantamental-investing-across-the-world] * Become a Great Presenter and Increase Your Influence [https://academy.astotz.com/courses/gp] * Transform Your Business with Dr. Deming’s 14 Points [https://academy.astotz.com/courses/transformyourbusiness] * Achieve Your Goals [https://academy.astotz.com/courses/achieve-your-goals] CONNECT WITH ANDREW STOTZ: * astotz.com [https://www.astotz.com/] * LinkedIn [https://www.linkedin.com/in/andrewstotz/] * Facebook [https://www.facebook.com/andrewstotzpage] * Instagram [https://www.instagram.com/andstotz/] * Threads [https://www.threads.net/@andstotz] * X [https://twitter.com/Andrew_Stotz] * YouTube [https://www.youtube.com/c/andrewstotzpage] * My Worst Investment Ever Podcast [https://itunes.apple.com/us/podcast/my-worst-investment-ever-podcast/id1416554991?mt=2]

Scott Alldridge – Hot Coffee, Cold Reality: The $10,000 Drone Delivery Mistake

BIO: Scott Alldridge is CEO of IP Services and President of the IT Process Institute, a bestselling author of the VisibleOps series, and a Certified Chief Information Security Officer. STORY: Scott’s worst investment was a stake in a startup promising to deliver hot coffee by drone. Excited by the futuristic idea, he invested before the concept was proven—but the project quickly crashed when the FAA banned drone deliveries and a prototype failed spectacularly. LEARNING: Being first doesn’t always mean being right. Due diligence is non-negotiable.   > “You don’t have to jump in. Being the first with the most doesn’t matter if it’s a bad idea—you’ll lose money anyway.” > Scott Alldridge   GUEST PROFILE Scott Alldridge [https://www.linkedin.com/in/scott-alldridge-1a976/] is CEO of IP Services [https://ipservices.com/] and President of the IT Process Institute [https://itpi.org/], a bestselling author of the VisibleOps series [https://amzn.to/3LHEkJn], and a Certified Chief Information Security Officer. He holds an MBA in cybersecurity and has over 30 years of experience in IT and cybersecurity leadership. Scott empowers organizations to achieve resilience through process excellence, Zero Trust, and AI-driven security. WORST INVESTMENT EVER If you live in the Pacific Northwest, coffee isn’t just a drink; it’s a way of life. Seattle is home to Starbucks, and in Oregon, coffee culture runs deep. So when Scott was pitched an idea that combined coffee and technology—delivering hot coffee via drone—he couldn’t resist. The concept sounded revolutionary: push a button on your phone, and a drone drops off your piping-hot Americano right at your doorstep. It felt like the future—part Amazon innovation, part TED Talk dream. Excited, Scott invested for a 3% stake in the startup. The founders promised a caffeinated empire built on convenience and cutting-edge tech. But just three months later, the buzz wore off. The FAA issued a cease-and-desist order on all drone delivery experiments, particularly those involving liquids. And then came the final straw: the company’s prototype drone spilled an entire cup of hot coffee mid-flight, grounding both the drone and Scott’s hopes. The “coffee drone revolution” turned into a $10,000 lesson in wishful thinking. Delivering hot coffee by drone was never going to fly—literally. LESSONS LEARNED * Being first doesn’t always mean being right. * It’s tempting to jump into the next big idea, especially when it sounds exciting and visionary. However, early-stage innovation carries significant risk, especially when the concept hasn’t been tested or proven. * Enthusiasm can cloud judgment. Instead of investing based on a slick pitch deck or futuristic concept, it’s smarter to wait until an idea is validated, tested, and compliant with regulations. ANDREW’S TAKEAWAYS * Every idea looks brilliant until reality—and regulation—show up. * Even in large corporations, where top analysts and executives lead multi-million-dollar mergers, success isn’t guaranteed. Only about 20% of them added value within three to five years. * Business is hard, and due diligence is non-negotiable. ACTIONABLE ADVICE Always do your due diligence. Before investing in any idea—no matter how exciting—slow down and dig deep: * Validate the concept. Is there a working prototype, or just a fancy pitch? * Check the regulations, especially if the business operates in a grey area (like drones or cannabis). * Assess the risk. What happens if laws, markets, or consumer behaviour change? * Stay patient. If it’s truly a good idea, it will still be good when it’s proven. SCOTT’S RECOMMENDATIONS Scott recommends his Amazon bestseller, Visible Ops Cybersecurity: Practical Ways to Enhance Your Cybersecurity Posture [https://amzn.to/47ntZed], which breaks down complex IT security concepts into real-world strategies that leaders can actually apply. For executives who don’t speak “tech,” he’s also written The Visible Ops Executive Companion Guide [https://amzn.to/47ntZLf], a concise 105-page edition with zero “geek speak”—just actionable guidance. And coming soon: Visible Ops AI: Artificial Intelligence Governance with Practical Guidance, where Scott explores how businesses can safely and responsibly integrate AI while protecting data integrity. NO.1 GOAL FOR THE NEXT 12 MONTHS Scott’s goal for the next 12 months is to double down on two things: growth and impact. On the business side, his goal is to expand the top-line revenue of his IT services firm and bring in new client partnerships. But there’s also a bigger mission driving him—making the world a safer place through smarter, more disciplined cybersecurity practices. PARTING WORDS   > “Thank you for having me today. Let’s keep the world a cyber-safe place.” > Scott Alldridge   [spp-transcript]   CONNECT WITH SCOTT ALLDRIDGE * LinkedIn [https://www.linkedin.com/in/scott-alldridge-1a976/] * Instagram [https://www.instagram.com/scottalldridge1/] * Facebook [https://www.facebook.com/scott.alldridge.24/] * Website [https://scottalldridge.com/] * Book [https://amzn.to/3LHEkJn] ANDREW’S BOOKS * How to Start Building Your Wealth Investing in the Stock Market [https://amzn.to/3qrfHjX] * My Worst Investment Ever [https://amzn.to/2PDApAo] * 9 Valuation Mistakes and How to Avoid Them [https://amzn.to/3v6ip1Y] * Transform Your Business with Dr.Deming’s 14 Points [https://amzn.to/3emBO8M] ANDREW’S ONLINE PROGRAMS * Valuation Master Class [https://valuationmasterclass.com/] * The Become a Better Investor Community [https://astotz.kartra.com/page/become-a-better-investor-community] * How to Start Building Your Wealth Investing in the Stock Market [https://academy.astotz.com/courses/how-to-start-building-your-wealth-investing-in-the-stock-market] * Finance Made Ridiculously Simple [https://academy.astotz.com/courses/finance-made-ridiculously-simple] * FVMR Investing: Quantamental Investing Across the World [https://academy.astotz.com/courses/fvmr-investing-quantamental-investing-across-the-world] * Become a Great Presenter and Increase Your Influence [https://academy.astotz.com/courses/gp] * Transform Your Business with Dr. Deming’s 14 Points [https://academy.astotz.com/courses/transformyourbusiness] * Achieve Your Goals [https://academy.astotz.com/courses/achieve-your-goals] CONNECT WITH ANDREW STOTZ: * astotz.com [https://www.astotz.com/] * LinkedIn [https://www.linkedin.com/in/andrewstotz/] * Facebook [https://www.facebook.com/andrewstotzpage] * Instagram [https://www.instagram.com/andstotz/] * Threads [https://www.threads.net/@andstotz] * X [https://twitter.com/Andrew_Stotz] * YouTube [https://www.youtube.com/c/andrewstotzpage] * My Worst Investment Ever Podcast [https://itunes.apple.com/us/podcast/my-worst-investment-ever-podcast/id1416554991?mt=2]

Dr. Thomas Powell – The One Rule You Must Never Break as an Investor (Even for Friends)

BIO: Thomas J. Powell, founder of The Powell Perspective™, is a seasoned entrepreneur, investor, and advocate for founders, bringing clarity, strategy, and resilience to leaders building at scale. STORY: Thomas invested $3.6M in a friend’s cannabis company, where he ignored his own due diligence framework. Because he skipped key governance protections and didn’t document alignment or exit terms, the investment became frustrating, hard to control, and nearly impossible to fix—proving that breaking your own rules is the most expensive mistake. LEARNING: Never mix friendship and business. Make sure both you and the founder are solving the same problem.   > “They say good fences make good neighbors, good documents keep good friendships.” > Thomas Powell   GUEST PROFILE Imagine navigating the high-stakes world of capital, strategy, and legacy with a guide who has raised billions and structured ventures worldwide. Thomas J. Powell [https://www.linkedin.com/in/thomasjpowell/], founder of The Powell Perspective™ [https://thepowellperspective.com/], is a seasoned entrepreneur, investor, and advocate for founders, bringing clarity, strategy, and resilience to leaders building at scale. WORST INVESTMENT EVER You’ve probably heard the saying, “Never mix friendship and business.” Thomas learned that lesson the hard way. His story starts with good intentions. When his kids’ grandmother battled breast cancer, cannabis was the only thing that eased her treatment side effects. So when medical marijuana became legal in a few US states, investing in the cannabis industry felt like the right thing to do. But here’s where things went wrong. A close friend brought him the deal, and because of that personal connection, Thomas skipped many of the due diligence steps he usually followed through his family office. No detailed governance clauses. No proper reporting framework. No accountability structure. It wasn’t a small investment either—about $3.6 million. As time went on, the cracks began to show. The company missed financial reports, accounting systems were weak, and when COVID hit, things only got messier. To make matters worse, taking over the business wasn’t even an option since he didn’t have a cannabis license. The emotional toll of this situation was significant, as Thomas had to face the reality of his investment failing due to trusting a friend blindly. The worst part? Having to look a friend in the eye, knowing he’d broken his own investment rules. LESSONS LEARNED * Verify alignment: Make sure both you and the founder are solving the same problem, and that you share the same exit goals. Ask questions like, “If someone offered to buy this company for $25 million today, would you sell?” If your answers don’t match, you’re not aligned. * Watch the hubris: Just because you’re smart or successful doesn’t mean you can see around every corner. Understand the legal and regulatory landscape before investing, especially in industries like cannabis, where compliance is complex. * Enforce accountability: Set clear reporting expectations from day one and include consequences for missed deadlines. Thomas admits that if his deal had stricter enforcement clauses, it would’ve saved him time, money, and frustration later on. ANDREW’S TAKEAWAYS * Many startups underpay themselves. It might sound noble, but it actually distorts valuation and creates problems later. * Make sure founders are paying themselves a market-rate salary. That way, when the business is valued or acquired, there are no nasty surprises about hidden costs. * Define roles clearly. Being a founder is different from being an employee. A salary compensates for your work; ownership rewards your risk. Mixing the two confuses things. ACTIONABLE ADVICE Align the capital and exit terms from day one—and write them down, even on a napkin. You don’t need a 30-page legal contract to start. Even a handwritten summary that defines the key terms, goals, and triggers for selling or exiting can prevent misunderstandings later. Because once the ink dries, or worse, once the money’s wired, it’s too late to wish you’d had that conversation. THOMAS’S RECOMMENDATIONS Thomas recommends these books, principles, and resources for smarter investing. * Read The Richest Man in Babylon [https://amzn.to/4oizUrb] – A timeless classic that teaches simple, lasting lessons about money management and investing in what you understand. * Invest in problems you understand. Don’t chase hype. If you know how an industry works, you’ll see both the risks and opportunities clearly. * Take advice from people with a “bigger pile.” In other words, learn from those who’ve already achieved more than you in that field. Theory is cheap—experience is priceless. * Use structured tools. Thomas’s Founders Office [https://www.founders-office.com/] provides frameworks that evaluate pitch decks for both founders and investors, helping you spot weaknesses and strengths before committing capital. NO.1 GOAL FOR THE NEXT 12 MONTHS Thomas’s goal for the next 12 months is to expand his Founders Office [https://www.founders-office.com/] cohort program, connecting entrepreneurs and investors to create better capital alignment. He’s passionate about free enterprise and founder advocacy, believing that capitalism—done right—can lift people out of poverty and fuel innovation worldwide. Whether in the US, Europe, or Sub-Saharan Africa, his mission is the same: empower founders and investors to build lasting, ethical wealth together. PARTING WORDS   > “Learn from other people’s experiences. When you see someone make a mistake, don’t repeat it because we don’t learn from the wins, we learn from the failures.” > Thomas Powell   [spp-transcript]   CONNECT WITH DR. THOMAS POWELL * LinkedIn [https://www.linkedin.com/in/thomasjpowell/] * Instagram [https://www.instagram.com/dr.thomasjpowell/] * Website [https://thepowellperspective.com/] * Master Class [https://www.6secretsraisingcapital.com/masterclass] ANDREW’S BOOKS * How to Start Building Your Wealth Investing in the Stock Market [https://amzn.to/3qrfHjX] * My Worst Investment Ever [https://amzn.to/2PDApAo] * 9 Valuation Mistakes and How to Avoid Them [https://amzn.to/3v6ip1Y] * Transform Your Business with Dr.Deming’s 14 Points [https://amzn.to/3emBO8M] ANDREW’S ONLINE PROGRAMS * Valuation Master Class [https://valuationmasterclass.com/] * The Become a Better Investor Community [https://astotz.kartra.com/page/become-a-better-investor-community] * How to Start Building Your Wealth Investing in the Stock Market [https://academy.astotz.com/courses/how-to-start-building-your-wealth-investing-in-the-stock-market] * Finance Made Ridiculously Simple [https://academy.astotz.com/courses/finance-made-ridiculously-simple] * FVMR Investing: Quantamental Investing Across the World [https://academy.astotz.com/courses/fvmr-investing-quantamental-investing-across-the-world] * Become a Great Presenter and Increase Your Influence [https://academy.astotz.com/courses/gp] * Transform Your Business with Dr. Deming’s 14 Points [https://academy.astotz.com/courses/transformyourbusiness] * Achieve Your Goals [https://academy.astotz.com/courses/achieve-your-goals] CONNECT WITH ANDREW STOTZ: * astotz.com [https://www.astotz.com/] * LinkedIn [https://www.linkedin.com/in/andrewstotz/] * Facebook [https://www.facebook.com/andrewstotzpage] * Instagram [https://www.instagram.com/andstotz/] * Threads [https://www.threads.net/@andstotz] * X [https://twitter.com/Andrew_Stotz] * YouTube [https://www.youtube.com/c/andrewstotzpage] * My Worst Investment Ever Podcast [https://itunes.apple.com/us/podcast/my-worst-investment-ever-podcast/id1416554991?mt=2]