21st Century Entrepreneurship

Martin Piskoric
  • 5.0 (73)
  • Entrepreneurship
  • Updated Daily

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.

  1. 3d ago

    #542 Robert Misheloff: How Do You Avoid a $3,000 Financing Scam?

    Robert Misheloff, Smarter Equipment Finance co-owner, is an equipment-financing entrepreneur, and we spoke about how small business owners can finance essential equipment without falling into costly traps. After running direct marketing campaigns for financing companies, Robert saw firms brag about how they “pulled the wool over the eyes of their customers.” That experience pushed him to build a business around transparency and helping owners make informed financing decisions.  Robert breaks the market into three practical options: start with dealer financing, then try a bank, and only then look to private equipment financing when those routes do not work. Dealer programs can sometimes offer 0% rates—“You can't do any better than free financing”—while brokers become more useful for startups, used equipment, or challenged credit. He also explains how fake approvals can turn a seemingly standard deposit into a $2,000–$3,000 loss, and why reading negative reviews for patterns of deceptive behavior matters before signing anything.    For Robert, the larger purpose is helping very small businesses—often just one to four employees—turn equipment into economic opportunity. He walks through a dump-truck example where someone earning $50,000–$60,000 annually could potentially build toward roughly $10,000 monthly after modeled expenses, then add trucks and drivers over time. In industries like trucking and construction, “the equipment literally is the business,” making the quality of a financing decision consequential not just for the company, but for the owner and their family.   Listeners leave with a concrete framework for comparing financing options, spotting scams, and deciding when debt can genuinely help a small business grow. Key takeaways  Check dealer financing first; 0% offers can beat every alternative.  Try your bank before entering the private equipment-financing market.  Brokers are strongest for startups, used equipment, or challenged credit.  Read negative reviews specifically for patterns suggesting fake approvals or deposit scams.  Never assume an approval deposit is refundable without reading the contract.  Model revenue, expenses, payments, and repair reserves before financing equipment.

  2. Aug 19

    #541 Luke Girgis: How Do You Turn $400K a Month Into Breakeven?

    Luke Girgis is a founder, operator and author, and we spoke about why he believes companies should be designed around workflows rather than org charts. The idea grew out of businesses where revenue increased but efficiency did not: while running Rolling Stone and Variety Australia, margins never exceeded 4% because new revenue continually required more people. Looking back, Luke says, “we were just buying revenue with labor.”  That lesson became urgent when Luke stepped into an interim CEO role at an e-commerce food business losing $400,000 a month. He broke every role into microtasks, mapped the workflows from customer order to delivery, reorganized the business and used automation to help bring it to breakeven. His four-step method is straightforward: audit where the business is bleeding, architect the highest-value workflow, activate the solution, then accelerate what works. Simply bolting AI onto an existing operation, he argues, is like “driving a Ferrari in traffic.”   In his artist management business, automating 90% of managers’ administrative work freed them to spend their time developing artists—and every artist on the roster is now earning more than ever before. Luke’s principle is that “we hate wasting their time,” connecting automation not just to lower costs, but to better work, stronger careers and businesses more capable of surviving.   Listeners leave with a concrete method for finding wasted work, redesigning workflows and applying AI where it creates measurable operating leverage. Key takeaways  Map individual tasks before deciding what technology to automate.  Redesign workflows first; reorganize people around those workflows second.  Revenue growth is not scaling if headcount must rise equally.  Audit, architect, activate, then accelerate the workflows producing results.  Automating 90% of admin can redirect people toward higher-value work.  Treat AI as a tool for saving time, not replacing people.

  3. Aug 17

    #540 Marissa Alfe & Lauren Fitzgerald: Why Isn't Talent Enough?

    Marissa Alfe & Lauren Fitzgerald is the partnership behind a boutique talent agency PRTNRS MGMT, and we spoke about what it takes to turn creative talent into a durable business. After years in artist representation, they launched their own agency as COVID upended the industry; Marissa remembers, “I had $800 in my checking account,” while still needing to protect clients she had spent years building. Their response was to help artists become more visible, commercially valuable and entrepreneurial because, as Lauren puts it, “the talent today really is not enough.” Their approach is deliberately hands-on. Instead of building the kind of 50-to-200-person roster they saw elsewhere, they keep their roster small enough to combine daily bookings with long-term career strategy, brand partnerships and even travel logistics. That means maintaining relationships with publicists, editors and brands, creating consistent social content, and double-checking everything from pickup times to approved captions rather than assuming someone else handled it. Underneath the tactics is a philosophy Lauren summarizes simply: “relationships are everything.” Their story shows how trusted networks, continuous learning and disciplined client advocacy can turn a frightening entrepreneurial starting point into a focused agency built for long-term careers—not just the next booking. Key takeaways Treat creative talent as a business, not just a craft.Build relationships with brands, publicists, editors and peers before opportunities appear.Keep your roster small enough to provide meaningful career strategy.Double-check critical details instead of assuming another party handled them.Use difficult market shifts to create new value for clients.Keep learning even after becoming an expert in your field.

  4. Aug 11

    #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.

  5. Aug 8

    #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 takeaways Define 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.

  6. Aug 5

    #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.

  7. Aug 3

    #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 takeaways Fully 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.

  8. Jul 31

    #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 takeaways Map 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.

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About

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.

Information

  • Creator
    Martin Piskoric
  • Years Active
    2017 - 2026
  • Episodes
    541
  • Rating
    Clean
  • Copyright
    © 2026 21st Century Entrepreneurship
  • Show Website
    21st Century Entrepreneurship