21st Century Entrepreneurship

Martin Piskoric
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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. 11H AGO

    Sam Miles: How do you avoid IRS audits as an entrepreneur?

    Sam Miles is a CPA, and we spoke about how entrepreneurs can legally reduce taxes while avoiding the small, preventable mistakes that trigger IRS audits. Drawing on years of audit defense and advisory work, Sam explains why “it’s not the spending of money that makes a tax deduction, it’s the context or the story,” and why documentation—not clever tricks—is what actually protects you as the IRS gets better at AI-driven matching. We also talked about where most entrepreneurs get into trouble: unreported 1099 income, poor documentation, and not knowing their own numbers. Sam urges business owners to actively review their IRS transcripts, reminding listeners that “nobody knows your numbers like you do,” and that missing income is “the most common, easiest way to get audited.” He shares how CPAs read tax returns as stories—and why pushing your CPA to explain that story can reveal risks early. Sam’s approach is grounded in ethics and realism. He breaks down practical tools like reasonable compensation, entity structure decisions, and why some popular strategies backfire when abused. As he puts it, “little pigs are cute, but hogs, they get slaughtered,” a reminder that aggressive shortcuts often cost more in time, stress, and money later. The episode closes with a clear message: do it right, document it properly, and use the rules as written. Key takeaways Missing 1099 income is the fastest path to an IRS auditCheck your IRS transcript to verify all reported incomeDeductions depend on business context, not just spendingDocumentation must be done before, not after, tax filingsReasonable compensation protects S-corp owners in auditsCPAs read tax returns as stories—ask them to explain yours

    26 min

  2. 1D AGO

    Chris Kille: How did delegation save his life and business?

    Chris Kille is a serial entrepreneur who exited multiple companies, and we spoke about how running everything himself nearly killed him—and why delegation changed everything. At his first exit, he was earning a few million a year but doing every job himself, until “they thought I had a stroke.” That moment forced a hard reset: if the business depends on the founder, it’s fragile, stressful, and worth far less than owners believe. We talked through the practical method he learned the hard way: replacing yourself step by step. Chris explained why founders should offload admin first, then customer support, then marketing—before sales—so revenue doesn’t collapse under its own weight. He shared how documented workflows, SOPs, and clear expectations matter more than heroics, and why “80% done by somebody else is a hundred percent awesome” when it frees the founder to lead. Chris also unpacked the deeper reason this matters. Removing himself from daily operations didn’t just increase valuation and exit multiples; it gave him his life back. As he put it, “Systems matter more than people,” because strong systems survive churn, scale without burnout, and protect what matters most—health, family, and time. If you’re building a company that feels stuck, exhausting, or unsellable, this conversation offers a concrete blueprint for turning effort into leverage—and a business into an asset. Key takeaways Founder-dependent businesses get lower exit multiplesNearly burning out forced delegation and changeHire admin first, not salesDocument SOPs for every repeatable taskStrong systems outperform individual talentDelegation creates time, health, and freedom

    22 min

  3. 5D AGO

    Kate Assaraf: Seven-figure growth without ads?

    Kate Assaraf is an economist and founder, and we spoke about how she built a seven-figure, mission-driven business through word of mouth—without paid ads, influencers, or marketplaces. Her turning question was simple and risky: could a modern business grow purely through trust and real customers? She decided to prioritize direct relationships, email lists, and selective distribution, arguing that when platforms reward “the cheapest, the fastest,” the best products lose control of their customers. Her core method was choosing community over algorithms. She explains that “customers are really, really smart” and can quickly spot “fake purchased authenticity,” which is why she avoided incentivized reviews and staged content. By staying off dominant marketplaces and refusing paid social, she protected margins, kept ownership of customer relationships, and leaned into face-to-face retail and grassroots discovery. As she puts it, “I chose to build my company with communities over algorithms,” even when that path was slower and harder. We also talked about the mindset and structure required to sustain that choice: loving the product category enough to talk about it daily, protecting the business legally, and developing thick skin. Kate stresses learning to “shut your ears off to advice” when it doesn’t align, and using capitalism intentionally—what her team calls “Operation Big Check”—to fund causes customers actually care about. The result was unexpected media attention and awards that came from building differently, not chasing coverage. This conversation offers a grounded playbook for entrepreneurs who want growth without sacrificing trust, margins, or purpose. Key takeaways Word of mouth can scale to seven figures without paid adsKeep customers off marketplaces to control relationships and marginsAvoid fake UGC; real customers build faster trustChoose selective retail over algorithmic distributionLove your category enough to talk about it dailyUse profits intentionally to reinforce values and loyalty

    14 min

  4. 6D AGO

    Trevor McGregor: Why busy founders can’t scale?

    Trevor McGregor is a high-performance coach and CEO, and we spoke about why so many entrepreneurs feel burned out, misaligned, and trapped by the businesses they built. After “over 45,000 one to one coaching sessions,” Trevor has seen the same patterns repeat: founders hustling harder, short on time, and unsure what they’re even optimizing for anymore. He breaks this down into five concrete blockers to scale: limiting beliefs, no clear strategic plan, missing systems, poor time management, and weak execution. Trevor explains why “most people spend more time planning their vacation than they do their business and their life,” and how reverse-engineering a clear short-, mid-, and long-term plan changes momentum. From there, he emphasizes building systems that support daily action, optimizing what to do, delegate, or drop, and taking “intelligent and inspired action” instead of reactive busyness. We also talked about his core framework—the four S’s: state, story, standards, and strategy—and why mindset is the real lever behind results. Drawing from his work with Tony Robbins and clients like Joe Fairless, Trevor shows how owning your inner state and standards can unlock financial, time, and location freedom, all in service of impact and legacy. Listeners will leave with a clear picture of what actually drives scale—and what to fix first. Key takeaways Burnout comes from hustling without clear goals or priorities.Identify and dismantle limiting beliefs before scaling.Create a strategic plan, then reverse-engineer daily actions.Systems and support make growth sustainable.Optimize time: do, delegate, or dump tasks.Execution requires intelligent and inspired action.

    13 min

  5. 12/30/2025

    Scott Abbott: How systems turn chaos into scalable growth?

    Scott Abott is the founder and CEO of BOS-UP, a three-time bestselling author, and a former EY Entrepreneur of the Year finalist. He is a systems implementer and early-stage investor, and we spoke about why structure—not hustle alone—is what actually allows companies to grow. After decades in ERP, SAP, and Oracle environments, and after building (and overbuilding) his own ventures, Scott learned the hard way that speed without discipline creates fragility. As he put it, “Be quick, but don’t hurry,” a lesson earned after raising millions, scaling too fast, and realizing how much he didn’t yet know. We unpacked his core method: combining entrepreneurial energy with clear agreements, simple operating rules, and shared language. Scott explained how alignment comes from fusing systems with humanity—“agreement-based commitments” paired with grace for individual style—so teams can be confident, resilient, and adaptable. He emphasized that antifragility isn’t about control, but about clarity: vision, values, roles, metrics, and communication that keep everyone on the same page. We also talked about leadership, mentorship, and harmony over balance. Scott reframed growth as learning to “work on and in the business” using concepts, tools, and discipline—plus reflection and self-awareness. His why is practical and human: helping founders, teams, and communities avoid unnecessary pain, save time, and build something that benefits “both the company and the individual.” Listeners will walk away with a grounded way to scale—one that protects energy, improves decisions, and makes growth feel sustainable rather than chaotic. Key takeaways Scale speed with discipline, not hustle aloneUse agreement-based commitments to reduce fragilityCombine systems with grace for individual styleWork on and in the business intentionallyChoose harmony over unrealistic work-life balance

    21 min

  6. 12/27/2025

    Scott Kelly: What actually gets a yes from investors?

    Scott Kelly is a veteran venture investor and advisor, and we spoke about what it really takes to raise capital after decades on both sides of the table. With 35 years in venture, multiple exits, and billions raised, Scott has seen where founders consistently get it wrong—and what actually moves investors to say yes. At the center of his approach is preparation and relationship-building. He explains why “running your startup is a full time job and raising capital is a full time job,” and why shortcuts don’t work. Instead of blasting pitch decks, Scott stresses building a vetted network—“a minimum of 100 to 200 people”—who invest in your industry and stage, then earning the right to pitch through real engagement. We also break down what investors expect when you finally get the meeting: a clear problem, a differentiated solution, a capable team, real competition awareness, a credible exit path, and a precise plan for how the money will be spent. Scott is blunt about resilience, reminding founders that rejection is part of the process, and that sometimes “the best raise, the way to raise capital is go sell something” before chasing investors. This conversation gives founders a grounded, no-nonsense roadmap for raising capital without wasting time, burning relationships, or fooling themselves about what investors actually look for. Key takeaways Build investor relationships long before you ask for moneyTarget investors by industry and company stageMaintain a network of at least 100–200 qualified investorsPitch decks must answer problem, solution, market, team, and exitExpect many no’s and keep updating investors with traction

    16 min

  7. 12/20/2025

    Rob May: When should you stop using just one AI model?

    Rob May is a serial founder (five startups) and we spoke about how he went from “I did not intend to go do a fifth” startup to building a new AI company after he “stumbled upon an AI idea” he could prove out—and couldn’t ignore. He’s been focused on AI since 2015 (after exiting his first company in December 2014) and framed the current moment simply: even “10 years later… we are still just at the beginning” of what’s coming. Rob walked through the real path to his current thesis: early bets, being “a couple years too early” pre-LLM, and a short venture-capital chapter that was “very intellectually stimulating,” but ultimately he missed “the battleground” of building and winning in-market. That experience shaped the core idea of the episode: most teams start with one big model, then hit the same wall—cost, speed, and inconsistent outputs—because models are probabilistic. As he puts it, “if you ask the same question multiple times, you might get different answers,” which is why techniques like Best-of-N (ask the same question 10 times) can reveal a distribution and help you avoid weak one-shot results while you decide what should run where. If you’re building with AI, this conversation gives you a concrete way to think about splitting work across multiple models, when you actually need a frontier model, and how small process changes (like repeated probing) can improve reliability without rewriting your whole product. Key takeaways Stop routing everything to one model; match model strength to task type.Use Best-of-N: ask 10 times, inspect outputs, choose the best.One-shot outputs can vary; plan for probabilistic behavior.Keep complex, variable tasks on frontier models; offload narrow tasks to smaller ones.Validate ideas fast; being “too early” is real in AI product timing.Optimize for accuracy, speed, and cost together by splitting workloads.

    36 min

  8. 12/16/2025

    Rod Khleif: How did he recover after losing $50M?

    Rod Khleif is a real estate entrepreneur and educator, and we spoke about how he rebuilt after losing $50 million during the 2008–09 crash—and the mindset that allowed him to have $50 million to lose in the first place. Growing up as an immigrant with little money, Rod watched his mother quietly build wealth through real estate, which pushed him to choose that path early and scale fast. The turning point came when rapid success fed ego, followed by a brutal correction. Rod calls it “a $50 million seminar,” and explains that recovery didn’t start with tactics, but with psychology: “80 to 90% of your success in anything is just that, your mindset and psychology.” Instead of obsessing over the loss, he reset his focus, reminding himself that “whatever you focus on gets bigger,” and deliberately re-anchored on goals, decisions, and daily action. We also broke down the practical structure behind that comeback: aggressive goal setting, making a non-negotiable decision (“motivation will get you started, but… commitment is what brings you home”), taking the first imperfect step, and surrounding yourself with peers who raise your standards. Rod shared how identifying limiting beliefs as “B.S.”—belief systems with no factual basis—helped him replace fear with momentum. This conversation is a grounded playbook for anyone facing a setback and wondering how to rebuild clarity, confidence, and forward motion without waiting for perfect conditions. Key takeaways Reset focus quickly; what you focus on expands.Set goals first, then define why they matter.Make a full decision—no halfway commitment.Take the first step before seeing the whole path.Expose limiting beliefs as unfounded assumptions.Choose peers who normalize higher standards

    19 min
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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
    490
  • Rating
    Clean
  • Copyright
    © 2026 21st Century Entrepreneurship
  • Show Website
    21st Century Entrepreneurship