21st Century Entrepreneurship

Hosted by Martin Piskoric

Business Entrepreneurship Education News

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538

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Aug 2026

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About the show

The 21st Century Entrepreneurship Podcast is a 4 x Gold-Award weekly show that features interviews with cutting-edge leaders and successful entrepreneurs. We talk about the fundamentals of starting and growing a business, achieving and maintaining success, as well as the difficulties of entrepreneurship and its future. Subscribe to the 21st Century Entrepreneurship Podcast and never miss an episode, so you can stay on top of the curve and gain the knowledge you need to succeed in today's competitive landscape.

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August 11, 2026Episode 5325 min

#539 Scott Oldford: Was $100M Worth Losing $14M?

Scott Oldford is a lifelong entrepreneur who built his first seven-figure business at 16, and we spoke about what happened when decades of entrepreneurial instinct collided with an identity he was trying to force. By 2022, he was making roughly $7 million a year at a 70% profit margin while working 15–20 hours a week. Then he chased a bigger identity and a $100 million outcome, losing $14 million across 2023 and 2024. Looking back, Scott says the difference between entrepreneurship as a “beautiful laboratory” and “a prison” can come down to ego. That collapse brought him back to what he believes he actually does best: understanding entrepreneurs, spotting patterns, and helping founders scale without unnecessarily reproducing his mistakes. His approach goes beyond tactics. He argues that sustainable scaling depends on mindset, nervous-system capacity, identity, and understanding whether you are operating reactively, willfully, intellectually, or intuitively. In marketing, he reduces the problem to relevancy, repeated exposure—generally “60+ times”—and intimacy: creating enough connection that you become the inevitable choice. A five-month illness then forced another practical shift. Unable to reliably take calls, Scott converted years of frameworks and judgment into AI-guided systems that walk entrepreneurs step by step through areas such as offers, email, marketing, and business strategy. Instead of requiring hours of courses or six-figure one-on-one engagements, his goal is to encode the logic behind his decisions so entrepreneurs can use it when they need it. Underneath that work is a simple motivation: helping founders feel “seen and heard” and avoid pain they do not need to experience themselves. The value for listeners is a practical framework for scaling around who you actually are—not around the business identity your ego says you should become.Key takeaways Define success before ego quietly replaces your original reasons for building. Scale around your natural strengths instead of forcing the wrong entrepreneurial role. Treat mindset, nervous system, and identity as core scaling infrastructure. Build marketing through relevancy, repeated exposure, intimacy, and human conversation. Use AI to compensate for structural, memory, and execution weaknesses. Identify recurring personal patterns before they distort business decisions.

August 8, 2026Episode 5226 min

#538 Denis O'Shea: How Do You Turn Technology Into Advantage?

Denis O'Shea is the founder and CEO of a technology services company, and we spoke about how a painful sales failure became the foundation for 22 years of helping organizations extract more value from technology. Early in his career at Nokia, a customer challenged him on why they should buy more technology when employees barely used what they already had. Denis says that conversation “burnt a piece of my brain.” He later built a 250-person mentoring operation that worked one-on-one with a million people across multiple countries, and today applies those lessons to AI, security, and workplace productivity.His own company’s AI rollout exposed exactly why enthusiasm is not enough. After deploying AI to roughly two-thirds of the organization, the team discovered 33,000 sensitive files that were overexposed, gaps in employee training, no clear foundation for AI agents, poorly defined use cases, and no objective way to demonstrate ROI. Their response became a five-part method: define use cases, secure and classify data, train people, establish a secure foundation for agents, and measure the economic value of AI-supported work.Denis also explains how extreme strategic focus changed his company’s trajectory. From New Zealand, his team committed to becoming exceptionally good at one narrow technology specialization, eventually winning a global partner award and gaining introductions to major enterprise customers. The discipline, he says, was to “say no to 99 things” while continuing to say yes to one thing for years. The same philosophy now informs his view of AI: build security in from the beginning, prepare for potentially hundreds of agents per employee, and expect companies to face three growing management problems—data, agents, and spend.For listeners, the practical value is a concrete framework for adopting AI without losing control of security, costs, focus, or measurable business outcomes.Key takeawaysDefine AI use cases before deciding who receives the technology.Audit and classify sensitive data before exposing it to AI.Train employees beyond browser-based AI into everyday productivity tools.Give every AI agent clear ownership, permissions, policies, and lifecycle management.Measure AI ROI at the task level, not through adoption alone.Say no to 99 opportunities to become exceptional at one.

August 5, 2026Episode 5125 min

#537 Jonny Price: Can Customers Be Your Best Investors?

Jonny Price is President of WeFunder, and we spoke about why startup investing should no longer be reserved for millionaires—and why founders may be overlooking one of their strongest sources of capital: their own customers. He explains how changes in U.S. regulation opened private investing to everyday people and why that shift creates opportunities not only for investors, but also for entrepreneurs who struggle to access traditional venture capital.Rather than positioning community investing as a replacement for venture capital, Jonny describes it as a complementary model. Some of the fastest-growing startups raise from top-tier VCs and still invite customers to participate because they want to “let their customers and community invest alongside” institutional investors. For founders outside Silicon Valley, the impact can be even greater. As Jonny puts it, “the vast majority of companies... are just not a good fit for venture capital,” making community funding a practical alternative instead of a last resort.The conversation goes well beyond fundraising mechanics. Jonny argues that a successful community round creates loyal customers, valuable product feedback, and emotional resilience for founders. He recalls one entrepreneur saying that traditional fundraising “feels like no,” while a community raise “feels like yes,” because every investment arrives as another vote of confidence. That support often translates into customers who buy more, stay longer, recommend the product, and genuinely want the company to succeed.Whether you're building a technology startup, healthcare company, local business, or consumer brand, this episode offers a practical look at how community capital can unlock funding, strengthen customer relationships, and make entrepreneurship a little less lonely.Key takeawaysVenture capital isn't the only path to raising startup capital.Turn existing customers into investors through community fundraising.Community investors often become loyal customers and product advocates.Lower investment minimums dramatically expand your potential investor pool.Fundraising should support building the company—not become the goal.Community backing provides emotional resilience alongside financial capital.

August 3, 2026Episode 5018 min

#536 Kim Butler: Should You Invest Before Saving $100K?

Kim Butler, Prosperity Thinkers founder, is a financial educator with more than 30 years of experience in banking, investing, and insurance, and we spoke about why strong earners often build wealth in the wrong order. Her starting question is direct: “You’re awesome at making money. How much of it are you keeping?” Rather than beginning with investment products, she helps entrepreneurial thinkers establish principles for making their own financial decisions.After a decade in the financial industry, Kim wrote her seven Principles of Prosperity in 1999. The first three—think, see, and measure—translate into a practical sequence: define and fully fund separate personal and business emergency reserves, continue accumulating an opportunity fund, and measure every decision by its opportunity cost. Using her example, a $100,000 emergency reserve could grow into $350,000, leaving $250,000 available for investments, acquisitions, or business opportunities without sacrificing peace of mind. As she puts it, “If you’re in a position of cash, opportunities will seek you out.”Kim also challenges people to compare mortgage prepayments, taxable interest, and other uses of cash against their highest realistic earning opportunity. The goal is not simply a better return—it is helping families sleep well, helping entrepreneurs act when opportunities appear, and ensuring more of every earned dollar remains productive.Listeners will leave with a clear order for building liquidity, evaluating financial trade-offs, and investing without weakening their safety net.Key takeawaysFully fund personal and business emergency reserves before discussing investments.Build a separate opportunity fund for large, time-sensitive investments.Choose reserve targets with your spouse or business partners.Measure mortgage prepayments against your highest realistic investment return.Prioritize liquidity and tax efficiency over small interest-rate differences.Match financial education to how you learn and take action best.

July 31, 2026Episode 4924 min

#535 Mike Ryan: Can AI Save Investors 80% of Their Time?

Mike Ryan, BPN CEO, is a former Goldman Sachs analyst who later ran its global equity business and managed Harvard’s $18 billion endowment, and we spoke about why powerful AI still fails investors when its answers cannot be trusted. After repeatedly receiving polished but incorrect information from generic tools, he decided to develop a more reliable approach. As he puts it, “AI wouldn’t pass a first-round job interview at most firms because it’s not trustworthy.”Ryan explains that AI has a “big stomach, but a very small mouth”: it can process enormous volumes, yet each answer depends on the limited information selected for that prompt. His method maps every question to the most reliable and relevant sources, uses trusted spreadsheets for calculations, preserves citations and source controls, and keeps one person directing the process through an “AI plus 1” model. Purpose-built agents can screen opportunities, identify the one or two highest-value priorities, and support complex decisions as new evidence arrives. The result he describes is decision-grade memos, models, and presentations produced in 80% less time, with templates or first drafts often completed within one or two days.For listeners, this is a practical blueprint for reducing processing work while preserving human judgment, accountability, and confidence in consequential decisions.Key takeawaysMap every AI prompt to the most reliable, relevant sources.Keep one human responsible for supervision, interpretation, and final judgment.Use trusted spreadsheets for calculations, then visualize results for faster review.Let AI screen opportunities before committing time to deep analysis.Update complex decisions iteratively as new evidence arrives.Use saved time for company visits, customer calls, debate, and judgment.

July 29, 2026Episode 4832 min

#534 Chris Majer: Why does coordination fail as companies grow?

Chris Majer is a former University of Washington rugby captain, performance psychologist, and organizational consultant, and we spoke about how practice, mood, and coordination determine whether growing companies can actually transform. An airport-bookstore encounter with George Leonard’s The Ultimate Athlete led him from rugby into Aikido, sports psychology, and work with elite athletes, Olympic teams, and Special Forces. That path eventually took his methods into business, where a 48-month engagement helped an AT&T division generate $3 billion in profit.Majer’s governing lesson is blunt: “Understanding is the booby prize.” Transformation fails when companies install new practices and processes on top of resignation, resentment, or distrust. Because “mood is everything,” leaders must first change the organization’s predisposition for action, then develop new leadership and coordination practices, and finally align compensation, recognition, promotion, and workflows with them. He recommends judging learning by what people can do, dedicating 3–10% of working time to development, and allowing months—not a weekend—for competence to become embodied: “It’s simple, but it’s not easy.”Listeners will leave with a concrete sequence for turning stalled coordination into sustainable performance: shift mood, practice new actions, and make systems coherent with them.Key takeawaysDedicate 3–10% of working time to deliberate learning and practice.Change organizational mood before introducing new practices or systems.Align rewards, compensation, promotion, and workflows with teamwork.Treat coordination as the core capability required for scaling.Build competence through repeated action, not information alone.Sustain transformation through months of follow-up, not one intensive event.

July 28, 2026Episode 4714 min

#533 Simon Mach: How do you build a crypto firm for every cycle?

Simon Mach is a crypto trader and founder of MyCryptoParadise, and we spoke about how a lean operation that began with four traders survived repeated market cycles after launching in 2016. When meme-coin bets that worked during bull markets vanished in a downturn, Simon stopped chasing potential 1,000% gains and developed a professional approach guided by one hierarchy: “Capital protection first, consistency second, and growth third.”He explains why professionals calculate potential losses before profits, determine exit rules before entering a trade, and use checklists to prevent volatility from hijacking their decisions. The business grew through word of mouth with almost no initial expenses, while Simon treated focus as an economic resource because “your main product is your time and you yourself.” His team publishes both profits and losses, limits participation when added trading volume could expose its positions, and even uses a 12-song album to reinforce the daily discipline behind “risk first, profit second.”Listeners will gain a practical framework for protecting capital, managing emotions, and building consistency that can outlast a bull market.Key takeawaysCalculate the possible loss before considering a trade’s potential profit.Define profit targets and loss limits before entering every trade.Use daily routines to protect focus and decision quality.Publish wins and losses to earn trust through transparency.Cap participation when added volume could expose your strategy.Reinforce disciplined behavior with checklists and repeated daily cues.

July 24, 2026Episode 4627 min

#532 Xavier Rivera: How Did a $300K Trade Erase $60K Debt?

Xavier Rivera is a former U.S. Marine, trader, and financial education mentor, and we spoke about turning a $200 teenage investment into $20,000—then borrowing $60,000, losing most of it, and spending four years trapped in debt. At 17, he entered the military believing his basic needs would be covered while he learned the markets, but the failed pharmaceutical trade pushed him so far into pressure that, as he says, “I was so deep in survival mode.”During a nine-month deployment aboard the USS America without internet access, Xavier printed financial materials, studied constantly, and began translating market concepts into the language of engines, transmissions, and mechanical systems. Teaching other Marines helped him understand the infrastructure himself; after returning, a researched electric-vehicle options trade earned him about $300,000 while three people at the table became millionaires. He stresses that this was a unique event, not a repeatable promise: traders must “calm your nervous system down and learn first,” prove a strategy, manage risk, and “become an operator, not a trader.”Listeners will leave with a practical framework for studying markets, testing systems, protecting savings, and recognizing opportunities without blindly following someone else.Key takeawaysLearn the market’s language before risking meaningful capital.Build a repeatable system instead of copying another trader’s positions.Calm your nervous system before expecting consistent decisions.Prove your strategy before accessing larger proprietary-firm capital.Protect savings by separating education, testing, and funded trading.Teach complex concepts simply to deepen your own understanding.

July 22, 2026Episode 4531 min

#531 Timothy Dougherty: How do meals become measurable wins?

Timothy Dougherty is a fitness entrepreneur and franchisor, founder and CEO of Project LeanNation, and we spoke about rebuilding identity after poverty, financial success, federal prison, and the collapse of everything he had tied his value to. The gym was the first place “where pain had purpose,” and keeping a small promise—to arrive at 6:00 each morning—gave him evidence that he could become disciplined. Years later, despite the house, Porsche, boat, and growing family, he says, “I never felt more empty.”After serving 1,000 nights in federal prison, Timothy returned home with anxiety, guilt, and no clear direction. He relied on a repeatable daily routine, Rational Self-Analysis—thinking about his own thinking—and the confidence that adversity had revealed his ability to persevere. Training one person became meal preparation for many; soon he was producing 1,000 meals each weekend while learning that “it wasn’t the food.” The real value was consistent support, accountability, empathy, and honest conversations that helped people change their behavior.That relationship-based approach eventually became a scalable operating model. Timothy describes spending a decade reaching roughly 30 units, then awarding more than 100 territories within 12 months after building stronger development and support teams. His practical method includes continuously auditing processes, educating himself before hiring specialists, protecting culture through accountability, and accepting that leadership sometimes requires delivering unpopular news. His mission is grounded in service—“we rise by serving others”—and in making healthier choices more accessible to adults and children.Listeners will learn how small promises, structured reflection, consistent service, and transferable skills can turn adversity into disciplined leadership.Key takeawaysKeep one small daily promise until discipline becomes evidence.Use routine to reduce uncertainty during high-pressure seasons.Examine your thinking before challenging someone else’s beliefs.Build support, accountability, and education into the operating model.Learn enough to identify and hire genuinely competent specialists.Protect the shared mission, even when accountability makes you unpopular.

July 20, 2026Episode 4415 min

#530 Mike Stone: Can 10 People Scale $5M to $10M?

Mike Stone is President & CEO of CertaPro Painters®, and we spoke about building scalable businesses through trust, proven systems, technology, and values. After more than 26 years with the organization, Mike believes sustainable growth comes from moving beyond individual projects toward long-term relationships because “projects end,” while strong customer relationships endure.Mike explained how franchising lets entrepreneurs be “in business for yourself, not by yourself,” combining independence with coaching, technology, national sales support, and established processes. He described an unusually fragmented $60–70 billion North American market where even the largest operator holds roughly 1% market share. Franchise owners receive different support as they grow—from accurate estimating and financial discipline to hiring, leadership development, succession planning, tax considerations, and maximizing enterprise value.Technology will reshape how that work is managed rather than eliminate it. Mike expects AI to improve marketing, proposals, estimating, and organizational knowledge, potentially allowing ten employees supporting a $5 million operation today to support a $10 million business in the future. Remote estimates, property data, Google Earth, FaceTime, reviews, and strong customer metrics will also reduce friction as younger customers increasingly expect digital buying experiences. Underneath these changes is a values-based culture built around keeping promises, respecting individuals, pursuing excellence, continuously improving, and being willing to “embrace the possibilities.”Key takeaways Build lasting customer relationships instead of optimizing only for individual projects. Use proven systems while preserving the franchise owner’s entrepreneurial independence. Develop financial discipline early, then add talent and leadership capacity. Apply AI to proposals, estimating, marketing, and shared organizational knowledge. Design remote buying experiences around data, reviews, and customer convenience. Protect long-term growth with clear values, succession planning, and continuous improvement.Listeners will gain a practical framework for scaling a service business without sacrificing trust, profitability, or customer experience.

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Listen to episodes

#539 Scott Oldford: Was $100M Worth Losing $14M?

#538 Denis O'Shea: How Do You Turn Technology Into Advantage?

#537 Jonny Price: Can Customers Be Your Best Investors?

#536 Kim Butler: Should You Invest Before Saving $100K?

#535 Mike Ryan: Can AI Save Investors 80% of Their Time?

#534 Chris Majer: Why does coordination fail as companies grow?

#533 Simon Mach: How do you build a crypto firm for every cycle?

#532 Xavier Rivera: How Did a $300K Trade Erase $60K Debt?

#531 Timothy Dougherty: How do meals become measurable wins?

#530 Mike Stone: Can 10 People Scale $5M to $10M?

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