21st Century Entrepreneurship

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21st Century Entrepreneurship

Martin Piskoric

485 episodes

2 days ago

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 ...

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Entrepreneurship

Self-Improvement

All content for 21st Century Entrepreneurship is the property of Martin Piskoric and is served directly from their servers with no modification, redirects, or rehosting. The podcast is not affiliated with or endorsed by Podjoint in any way.

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 ...

Show more...

Entrepreneurship

Self-Improvement

Episodes (20/485)

21st Century Entrepreneurship

Scott Abott: 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 h...

5 days ago

21 minutes

21st Century Entrepreneurship

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 ...

1 week ago

16 minutes

21st Century Entrepreneurship

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, ...

2 weeks ago

36 minutes

21st Century Entrepreneurship

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 mil...

2 weeks ago

19 minutes

21st Century Entrepreneurship

David Deane-Spread: How do you become employer of choice?

David Deane-Spread is a former military and law-enforcement leader who built a decades-long career helping organizations turn cultural dysfunction into alignment, resilience, and performance. We spoke about how he applies the same persistence that kept him “fully booked without marketing for 20 years” to transform leadership teams and entire companies. His approach centers on what he calls the ABC practice of leadership—attitudes, behaviors, and conversations—which he says are responsible for...

3 weeks ago

23 minutes

21st Century Entrepreneurship

Jake Stahl: Are You Missing Hidden Decision Signals?

Jake Stahl is a psychology-trained communication strategist, NLP master practitioner, and global trainer who has coached over 10,000 people across six countries—and we spoke about how people actually make decisions. His core premise is simple: every person has two profiles, the polished public one and the internal one “that responds to fear and biases and happiness,” and only that second profile makes decisions. Jake teaches leaders, founders, and sales teams how to communicate directly to th...

1 month ago

13 minutes

21st Century Entrepreneurship

Peter Maher: Can cash-flow beat broken credit?

Peter Maher is the U.S. expansion lead for Ovanti—recently rebranded as Flote—and we spoke about why he left a stable, well-paid role in fintech leadership to build an alternative to what he calls a “very, very broken” credit system. With 12+ years in payments, partnerships, and market launches, he brought a career’s worth of operational and commercial experience to a problem he personally lived through. Maher’s motivation is rooted in his early setbacks. A single poor decision at 19 “cost me...

1 month ago

15 minutes

21st Century Entrepreneurship

Jeff Abraham: Why do men last 5:40 while women need 18 min?

Jeff Abraham is an entrepreneur who retired after selling a semiconductor engineering company, and we spoke about how he later built a sexual wellness brand by using medical credibility instead of hype. He explained that “even in healthy couples, the average man finishes in 5 minutes and 40 seconds” while “the average female takes 18 minutes,” a difference he called “the arousal gap.” Rather than compete with “197 products online—shark fin, deer antler extract,” he chose to power statisticall...

1 month ago

22 minutes

21st Century Entrepreneurship

AJ Cassata: Can Cold Email Really Fill a Sales Pipeline?

AJ Cassata is an entrepreneur who has spent more than a decade building companies using one core mechanism—outbound lead generation. We spoke about why so many founders struggle with lead flow and how, as he says, “leads are the lifeblood of your business,” yet most assume they need ads, a large audience, or influencer status to grow. His turning point was realizing that targeted outbound—“starting conversations with your target market at scale”—can outperform paid channels when done with pre...

1 month ago

14 minutes

21st Century Entrepreneurship

Paul Cecil: When can going public unlock real growth?

Paul Cecil is the VP of Strategy at realpha and we spoke about how a young founder-minded strategist thinks through scale, pressure, and the role of AI in real business results. He began as a pre-med student, switched into business after realizing he “liked trading stocks a lot more,” and later worked for years without pay to learn capital formation. Joining realpha as employee number ten, he helped drive seven acquisitions, eight capital raises, and a NASDAQ listing in under three years. A k...

1 month ago

18 minutes

21st Century Entrepreneurship

Bogdan Micov: How fast can identity shift?

Bogdan Micov is a former CEO who led 700 people in Dubai before a stroke at 32 forced him to confront what he calls “how stress affects us” and how much of his success was built on pressure rather than wellbeing. We spoke about his shift from operating on cortisol to operating from calm, and the method he later developed to help high performers do the same. His approach is built on a simple chain: thinking creates emotion, emotion shapes behavior, and behavior determines results. As he puts i...

1 month ago

26 minutes

21st Century Entrepreneurship

Srikar Yeruva: Can hospitals avoid waste with full-workflow data?

Srikar Yeruva is an engineer-turned-serial entrepreneur, and we spoke about why he believes healthcare transformation starts with respecting the problem—not throwing technology at it. After years building technical companies, exiting one to Bain Capital and selling another in smart contracts, he realized “technology doesn’t sell—solutions do.” That shift pulled him into the heart of U.S. health systems, where he learned firsthand how hospitals operate, why workflows break, and why efficiency ...

1 month ago

30 minutes

21st Century Entrepreneurship

Melissa Faith Hart: What makes people feel truly safe again?

Melissa Faith Hart is a public-safety innovator with 20 years of experience, and we spoke about how personal survival, technology, and community systems shaped her mission. She began her career at Xerox helping police departments modernize, eventually co-building the first criminal e-discovery system in Colorado. As she put it, she always asked, “how can I make the system better… so that we can help victims?” A major turning point came after a brain surgery and a domestic-violence crisis that...

1 month ago

15 minutes

21st Century Entrepreneurship

Brandon Williams: How persistence built billion-dollar deals and TV hits?

Brandon Williams is a lawyer, entrepreneur, and business executive with over twenty years of experience bridging law, business, and entertainment across the globe. We spoke about how he turned persistence and practical judgment into the foundation for billion-dollar deals and international success stories. After representing Fortune 10 companies and global icons, Williams learned that growth begins with grit: “Everything starts small. Learn to build. It’s going to be hard.” His journey took a...

1 month ago

16 minutes

21st Century Entrepreneurship

Adam Cerra: Can You Sell Without Selling?

Adam Cerra is a high-ticket sales expert who has closed more than $30 million in offers for coaches, consultants, and entrepreneurs. We spoke about how he teaches people to “sell without selling” — a process he calls inverse closing, where persuasion is replaced by empathy and guided conversation. As Adam puts it, “You’re not convincing anyone to buy anything. You’re getting your prospect to sell themselves for the offer.” His approach hinges on emotional intelligence — the ability to feel wh...

1 month ago

11 minutes

21st Century Entrepreneurship

Dwan Bent-Twyford: How Do You Earn Six Figures in Six Months?

Dwan Bent-Twyford is one of America’s most recognized real estate investors and educators, known for turning a $75 setback into a multimillion-dollar career. We spoke about how losing her home and car as a single mother became the catalyst for a 35-year journey and over 2,000 completed property deals. Her approach begins with empathy, not transactions. “People before profits,” she said, describing how she focuses on homeowners in distress—those facing foreclosure, divorce, or loss—rather than...

1 month ago

22 minutes

21st Century Entrepreneurship

John Frost: What’s your why—and are you ready to say yes?

John Frost is the Vice President of Enrollment Management and Marketing at Doane University with nearly 20 years in higher education across community colleges and private and public universities. We spoke about what it truly means to change lives through learning—and why education is not just for the gifted but for anyone curious enough to start. Frost believes that “what we do is what politicians, kings and queens promise to do—we change lives each and every day.” His approach goes beyond ac...

1 month ago

12 minutes

21st Century Entrepreneurship

Patrick Wood: Why Every Entrepreneur Should Plan for Failure?

Patrick Wood is a 30-year entrepreneur in finance and capital markets across Canada and the U.S., now leading an early-stage public company redefining how digital asset treasuries hedge risk. We spoke about what it really takes to endure the entrepreneurial grind — and why expecting failure can become your most powerful advantage. “Always plan on failure first,” Patrick says. “Expect it’s going to fail — then move, pivot, and adjust.” That mindset has guided his own journey, from stockbroker ...

2 months ago

18 minutes

21st Century Entrepreneurship

Gail Kasper: How logic saves your business from emotion?

Gail Kasper is an author, professional speaker, and performance coach who has spent over 15 years training entrepreneurs and executives—from solo founders to leaders in multi-billion-dollar companies—on leadership, customer service, and sales. We spoke about how few CEOs (only 15%) have ever been formally trained in sales, and why that missing skill often determines whether a business scales or stalls. Her approach centers on what she calls the Systematic Attitude Development Technique—a meth...

2 months ago

18 minutes

21st Century Entrepreneurship

Christopher Hossfeld: What can war teach us about leadership?

Christopher Hossfeld is a 27-year U.S. Army veteran and leadership educator who translates battlefield decision-making into modern business strategy. We spoke about how lessons from military history can sharpen leaders’ thinking, reduce bias, and strengthen organizations. “Investing in your people is the best way of spending your limited resources,” he explains—because leadership, at its core, is about leaving something that transcends business. Through his Barrel Strength Leadership framewor...

2 months ago

19 minutes