21st Century Entrepreneurship

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

An entrepreneurship podcast that transforms in-depth interviews with founders, CEOs, investors, executives, creators, and business leaders into tightly edited, first-person narratives that distill what matters most from their real-world experience. A four-time Gold Award-winning show with more than 540 published interviews, 21st Century Entrepreneurship explores how businesses are built, funded, scaled, transformed, and sometimes rebuilt from failure. Host Martin Piskoric guides each conversation toward the moments, decisions, lessons, and experiences most useful to listeners, then steps out of the final edit. What remains is the guest's voice—without small talk, unnecessary promotion, or interview clutter—shaped with music and space for reflection. Episodes cover entrepreneurship, leadership, business strategy, growth, marketing, finance and investment, AI and technology, personal development, and the realities of building and leading businesses.

  1. 1d ago

    #547 Dean Drako: How Do Product, Timing, and Luck Drive Success?

    Dean Drako is a serial entrepreneur who has founded somewhere between five and fifteen companies, raised venture capital around 20 times in Silicon Valley, and experienced both successful exits and failures—and we spoke about the operating lessons that came from building repeatedly. His starting principle is simple: find a pain point you understand deeply, make sure many other people share it, and build what he calls “painkillers, not vitamins.”  Dean also breaks company growth into three distinct organizational phases. From roughly one to 25 people, almost everyone knows everything; as the company grows, specialization and communication systems become necessary; and around 500 employees, the CEO must increasingly delegate and trust major leaders rather than rely on founder-level visibility. Timing can be just as decisive: one of his businesses spent roughly five years “pushing a rock uphill” because the market was not yet ready, reinforcing his view that success depends on product, timing, and some luck.  That long-term perspective also explains why Dean says, “I don’t believe in an exit.” Instead of optimizing a company for sale, he argues founders should build durable products, customer relationships, revenue, service, and leadership—while staying adaptable enough to move quickly when customers and markets change. For Dean, the larger purpose is practical as well: his current work is organized around making physical spaces safer.  For listeners, the value is a concrete framework for choosing problems, scaling leadership, surviving bad timing, and building for endurance rather than an exit. Key takeaways  Solve painful problems you personally understand and many customers actually share.  Expect leadership needs to change dramatically as headcount grows.  Around 500 employees, delegate major functions to trusted leaders.  Being years early can be as dangerous as having the wrong product.  Treat product, timing, and luck as separate ingredients of success.  Build enduring customer value instead of optimizing for an exit.

  2. 4d ago

    #546 Sam Demma: What Happens When You Expect Nothing Back?

    Sam Demma is an author and keynote speaker who has delivered close to 850 talks across four continents, and we spoke about how losing a Division I soccer scholarship after three major knee injuries redirected his life toward service, storytelling, and speaking. A teacher challenged him to take small, consistent action, which led to five and a half years of community cleanups—and eventually to schools inviting him back as a paid speaker. Sam also explains the practical principles behind his latest work: “assume positive intent” when customers, colleagues, or family frustrate you, and “self-evaluate first” before blaming someone else when things go wrong. He describes great speaking as combining useful ideas with humor and stories, while his broader philosophy is that “when you give expecting nothing in return, beautiful things unfold.” That philosophy is operational inside his company: 10% of annual profits after tax and expenses goes toward giving—half through books donated in January and half through cash donations in July, when charities may receive less support. For Sam, the purpose is less about what comes back financially and more about fulfillment, relationships, and knowing the work genuinely helps people. Listeners leave with practical ways to manage reactions, take ownership, communicate memorable ideas, and make generosity part of how they operate. Key takeaways Assume positive intent before reacting to an angry customer or difficult email.Self-evaluate your contribution before blaming someone when something goes wrong.Turn personal experiences into stories that help people change their behavior.Wrap useful information in humor and storytelling so people remember it.Build generosity into business intentionally instead of treating it as an afterthought.Small, consistent acts of service can open completely unexpected career paths.Learn more about Return on Goodwill and Sam’s live events at https://samdemma.com/rog-live/

  3. 5d ago

    #545 Amy Perez: Can Dreams Improve Your Decisions?

    Amy Perez, CEO at myDream & Mindful Software, Inc. - is a former government technology leader, Lean Six Sigma Black Belt, and responsible AI consultant, and we spoke about using dreams as another source of information for decisions, self-awareness, and major life changes. After years managing high-stakes programs - including a digital system that distributed more than $10 billion in pandemic aid - Amy was outwardly successful but exhausted: “I was slowly dying on the inside.” A violent dream centered on her work phone became the turning point. She quit, immediately felt “20 pounds lighter,” and she and her husband left their careers to travel the world for a year.  That experience led Amy into systematic dream interpretation and eventually to building an AI-assisted approach that combines emotions, common symbolism, personal meanings, recurring patterns, and input from experts with more than 180 years of combined clinical experience. What previously took Amy more than an hour can now be explored in seconds, but she stresses that interpretations should offer possibilities rather than dictate decisions. Her philosophy is equally clear about AI: “Technology should serve the person, not turn the person into the product.” Privacy, anonymization, expert review, and keeping human judgment in the loop are therefore central to the approach. For listeners, the practical starting point is simple: set an intention before sleep, record whatever you remember - even one word - and begin looking for recurring emotional and symbolic patterns over time. Amy created myDream to make that process easier: the app lets users capture dreams quickly, add their own personal meanings to symbols, explore expert-informed interpretations, and identify recurring trends that may connect to waking life. Her larger argument is especially relevant to entrepreneurs: “you will never have all of the data you need to make a decision,” so dreams and intuition can become an additional source of information- not a replacement for judgment, but another signal worth learning how to hear. Set an intention before sleep to strengthen dream recall.  Record dreams immediately, even if you remember only one word.  Track recurring symbols alongside your personal emotional context.  Treat dream interpretations as possibilities, not instructions.  Use subconscious insights as additional data for difficult decisions.  Design personal AI around privacy, reflection, and human judgment.Learn more about Amy’s work and explore myDream: https://www.mydream.io/

  4. Sep 8

    #544 Saurabh Gupta: Why Do 90% of AI Pilots Fail to Scale?

    Saurabh Gupta is CEO of The Modern Data Company, and we spoke about why so many AI initiatives struggle to scale despite massive investment in the technology. His perspective comes from nearly 30 years in data: designing the World Bank’s open data platform, spending 12 years leading statistical data at the IMF, serving as Chief Data Officer for Washington, DC, and later working across more than 20 major enterprise data initiatives at Thoughtworks. Across those environments, he kept seeing the same pattern: “people are not focusing on outcomes, people are focusing on technologies.” Saurabh explains why “bad data leads to bad AI,” and why adding more compute cannot fix a weak data foundation. His approach starts with right-to-left thinking: “bring only the minimum data that you need to solve a problem,” then expand as new problems emerge. He describes one manufacturer planning seven to eight quarters of foundational work before his team delivered the first use case and supporting platform in less than one quarter. Instead of stitching together 10–12 specialized tools, the method combines ingestion, quality, governance, orchestration, transformation and cataloging while keeping context attached to the data itself. Complex customer problems, he says, can often move from months to roughly four or five weeks. For listeners building with AI, the practical lesson is simple: start with the outcome, minimize the data and infrastructure required, prove value quickly, and only then expand. Key takeaways Start with the business outcome before choosing technologies or infrastructure.Bring only minimum necessary data, then expand as adjacent problems emerge.Replace 10–12 disconnected tools with a unified ingestion-to-cataloging layer.Package context, governance, lineage, and transformations with each data product.Track unused pipelines and shut them down to stop wasted compute.Aim to prove complex use cases in four to five weeks, not months.

  5. Aug 31

    #543 Digna Deleon-Morris: How Did $5.25 Become $4M a Month?

    Digna Deleon-Morris is an entrepreneur and insurance agency CEO, and we spoke about her path from arriving in the United States at 17 and earning $5.25 an hour to building an agency doing almost $4 million a month. Before entrepreneurship, she earned two college degrees, supervised 30 locations and managed $82 million in operations while working seven days a week — but, as a mother of four, realized, “I was building somebody else's business.”  The turning point was painful: after making millions in their first business, Digna and her husband lost everything in 2016 because, she says, they lacked financial education. They began learning through books, seminars and mentors, then applied those lessons to their own family before building a business around them. In 2023, Digna shifted her focus toward the Hispanic community and says she “literally 10x the business” by serving entrepreneurs in Spanish as well as English. Her broader method is equally clear: build people, create repeatable systems, delegate to leaders and give newcomers a structure they can “plug in and play.”  She also shares a practical 90-day planning framework covering seven areas: spirituality, health and energy, relationships, career, personal development, finances and contribution. Rather than waiting five years, she recommends defining what each area should look like in 90 days, writing it down and taking daily action — while using books, mentors, seminars and other successful people as blueprints. Her motivation comes back to family and freedom: she remembers being a mother who was rarely home and now wants other parents to build income without making the same sacrifice.  The practical value is a concrete model for turning personal growth, mentorship and repeatable systems into a business that can scale beyond you. Key takeaways  Set specific goals across seven life areas for the next 90 days.  Work harder on yourself, not simply longer inside the business.  Use mentors, books and proven examples instead of starting from zero.  Build repeatable systems newcomers can use without prior experience.  Delegate authority and develop leaders if you want a scalable business.  Serve an underserved community in the language and context it understands.

  6. Aug 25

    #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.

  7. 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.

  8. 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.

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About

An entrepreneurship podcast that transforms in-depth interviews with founders, CEOs, investors, executives, creators, and business leaders into tightly edited, first-person narratives that distill what matters most from their real-world experience. A four-time Gold Award-winning show with more than 540 published interviews, 21st Century Entrepreneurship explores how businesses are built, funded, scaled, transformed, and sometimes rebuilt from failure. Host Martin Piskoric guides each conversation toward the moments, decisions, lessons, and experiences most useful to listeners, then steps out of the final edit. What remains is the guest's voice—without small talk, unnecessary promotion, or interview clutter—shaped with music and space for reflection. Episodes cover entrepreneurship, leadership, business strategy, growth, marketing, finance and investment, AI and technology, personal development, and the realities of building and leading businesses.

Information

  • Creator
    Martin Piskoric
  • Years Active
    2017 - 2026
  • Episodes
    546
  • Rating
    Clean
  • Copyright
    © 2026 21st Century Entrepreneurship
  • Show Website
    21st Century Entrepreneurship