21st Century Entrepreneurship

Justine Froelker is a therapist-turned-speaker who helps entrepreneurs and leaders build what she calls “cultures of courage”—in life, business, and leadership. We spoke about the emotional cost of entrepreneurship, the myths of self-care, and the five essential pathways to courageous living. If you’ve ever felt burnt out while chasing your dream, or struggled to lead with both strength and authenticity, this episode is for you.Justine shares why so many high-performers neglect the very thing that makes performance sustainable: themselves. “We tend to never put ourselves—the care of ourselves—first,” she says. “And I’m going to come back every single time… you cannot give what you do not have.”Throughout our conversation, she outlines her Five Pathways of Courage—a framework born from decades of therapy work and corporate training—designed to help people not just survive their business journey, but live and lead well. We unpack topics like:Why emotional regulation is an entrepreneurial superpowerThe difference between values, beliefs, and identity—and why mixing them up leads to disconnectionWhy self-care isn’t about candles or baths but about boundaries and follow-throughWhat it means to show up fully you in spaces that aren’t always safeHow courage isn’t just in your head or heart—but “built between us”One of the most memorable moments comes when she reframes what leadership looks like today:“You can be a very vulnerable leader and your people still not know everything about you… Maybe you’re just vulnerable with how hard it is to lead these days.”Justine also opens up about leaving a successful private therapy practice to launch a speaking business, driven by a mission larger than revenue:“To create a space where people remember how loved they are—and then teach them how to live from that love.”Key Takeaways:Feel it all: Emotional literacy is the foundation of courageous leadership.Embody again: Show up and follow through for yourself—not just others.Be fully you: Authenticity invites connection, and connection is where growth lives.Love others well: Empathy and accountability aren’t opposites—they’re partners.Do the work: Real change begins when we rewrite the old stories we live by.Whether you’re leading a team or building your dream solo, this episode is a timely reminder: courage isn’t something you have or don’t—it’s something you build.

John Abrams is a builder, author, and visionary business leader who helped pioneer employee ownership in the U.S., and we spoke about how mission-driven companies can grow intentionally, remain deeply collaborative, and endure beyond their founders. What happens when a business born from passion faces the reality of succession? How do you preserve values, not just value?John shares his remarkable journey from being a “wandering hippie carpenter” to leading a 40-person architecture and building firm for decades — and ultimately transforming it into a worker cooperative. “Abrams, you've got a unique idea: subsidized housing for the rich,” a mentor once told him, prompting a turning point that ignited his business education and sparked a commitment to purpose-driven entrepreneurship.We explored the evolution of his company’s ownership model, how a sabbatical led to a powerful experiment in distributed leadership, and why he believes every small business should begin succession planning long before the founder steps aside. “It makes a lot of sense to disentangle the ownership progression from the leadership change,” he explains — an insight drawn from his own decades-long experience.At the heart of the conversation is John’s new book, From Founder to Future: A Business Roadmap to Impact, Longevity, and Employee Ownership, a guide for founders who want to keep their mission alive and share the wealth with the people who helped build their businesses. With millions of U.S. small business owners approaching retirement, John outlines a roadmap for longevity, impact, and fairness — offering real-world examples of employee ownership options like ESOPs, worker co-ops, and trust transitions.Highlights & Key Themes:The business case for not chasing endless growth: “It was not our aspiration to become a big company. It was our aspiration to become a great company.”How becoming a worker co-op changed everything — and made enduring excellence possible.Lessons from a failed leadership experiment, and how it eventually sparked a resilient management structure.The urgent need for succession planning: “Most small businesses don't think about it until the founder is ready to retire.”Three powerful employee ownership models — and why every founder should know them.Key Takeaways:Great companies can — and should — be small, values-driven, and democratically run.Succession isn’t a moment; it’s a long process that works best when begun early.Employee ownership isn’t one-size-fits-all — but it’s a transformative option founders often overlook.Intentionally designed transitions can preserve a business's soul while sharing its success.This episode is a masterclass in rethinking business not as a commodity to be sold, but as a legacy to be stewarded.

Ron Rubin is a seasoned entrepreneur, author, and dreamer who turned a 40-year vision into reality with his Sonoma County winery. We spoke about his journey from a small-town Southern Illinois upbringing to achieving his dream of owning a vineyard, the power of mentorship, the lessons learned from a lifetime in business, and the importance of pursuing dreams without delay. Rubin’s book, Gold in Your Backyard, distills 50 years of leadership and life lessons, emphasizing that opportunity is closer than you think.The most striking takeaway is Rubin’s philosophy of finding “gold” in your immediate surroundings. As he shares, “Well, the hook is gold in your backyard. You don’t have to go everywhere around the world. It’s right there. All you have to do is dig deep enough.” This mindset challenges the notion of chasing distant opportunities and encourages listeners to uncover potential in their current environment. His story of waiting 40 years to fulfill his winery dream after a life-threatening health scare in 2009 is a poignant reminder to act on aspirations sooner. “If you have a dream, go for it, make it happen. No one can tell us what’s going to happen tomorrow,” he urges, underscoring the urgency of living intentionally.Rubin’s practical wisdom shines through in his approach to business and life. He emphasizes mentorship, crediting his father and others for shaping his path: “My first lesson that I learned in 1972 was to find a mentor.” His voracious reading habit—over 3,000 business books—offers a self-education model for those without formal degrees. One clever nugget he adopted from The Trillion Dollar Coach is starting meetings with “low lights” before highlights, ensuring challenges are addressed first. He also shares a budgeting tactic for entrepreneurs: “Put a line called mistakes in your budget… when we made a mistake and it cost us a lot of money, I didn’t lose sleep over it. It’s in the budget.” This reframes mistakes as inevitable and manageable, reducing stress for business owners.From his advocacy for B Corp certification to his insistence on punctuality (“If you’re on time, you’re late”), Rubin’s lessons are both actionable and inspiring. His three keys to business success—customer satisfaction, employee satisfaction, and cash flow—distill complex entrepreneurship into a clear framework. “There’s only three keys to business… customer satisfaction, employee satisfaction, and cash flow,” he explains, highlighting the often-overlooked importance of liquidity.Key Takeaways:Seek Mentors Early: Find experienced guides to navigate your journey, as Rubin did with his father and others.Act on Dreams Now: Don’t wait for a crisis to pursue your passions—start today, as Rubin learned after his 2009 health scare.Embrace Continuous Improvement: Whether through B Corp certification or personal growth, aim to do better each year.Budget for Mistakes: Allocate funds for errors to reduce stress and turn unspent “mistake” budgets into profit.Master the Basics: Focus on customer satisfaction, employee satisfaction, and cash flow to build a sustainable business.Rubin’s story is a masterclass in resilience, resourcefulness, and redefining success by finding treasure where you stand. His blend of heart, hustle, and hard-earned wisdom makes this episode a must-listen for dreamers and doers alike.

Skip Wilson is a seasoned advertising expert whose journey began as a teenage copywriter trying to impress a girl, now his wife, and evolved into leading an ad execution company that helps businesses achieve tangible results. We spoke about the science of advertising, the pitfalls of modern marketing advice, and how to craft campaigns that actually work. Skip’s insights unpack why focusing on customer benefits over product details is key, how to navigate the overwhelming flood of “shoulds” in entrepreneurship, and why treating advertising as an objective, predictable process can transform a business.What stands out most is Skip’s relentless focus on results over flash. He challenges the industry’s tendency to prioritize awards or aesthetics over performance, sharing a formative moment: “I won the South Carolina Broadcaster Association Star Award... for an ad campaign I did for this bail bond company and that client canceled... they weren’t getting results. That bothered me so much that I had an award for a campaign that didn’t produce results.” This experience shaped his mission to make advertising a science, not an art, where every step—from click-through rates to conversions—can be measured and optimized like fixing an engine.Listeners can learn how to cut through marketing noise and focus on what drives growth: distribution and customer acquisition. Skip emphasizes that businesses thrive when they prioritize “how you get them from Little Mario to Big Mario,” not obsessing over the “mushroom” (the product). He also offers practical advice for beginners: start by defining your audience, their desired action, and the message that moves them. His formula for success—“business success equals people plus process plus product times distribution”—underscores that even a mediocre product can win with strong distribution, like McDonald’s.Skip’s perspective on stakeholder capitalism also adds depth, highlighting a responsibility beyond profits: “We pay a carbon offsetting company to offset our carbon footprint... I enjoy driving on roads that don’t have potholes... if I’m going to use the stuff, I should have to pay the stuff.” This ethos extends to fostering a workplace that supports employees’ dreams without restrictive non-competes, reflecting his belief that businesses impact real people, not just bottom lines.Key Takeaways:Advertising is a science, not an art. Treat it like troubleshooting a printer: check each step (ad response, landing page, conversions) to find and fix weak links.Focus on benefits, not features. Customers care about outcomes—going from “Little Mario to Big Mario”—not the product’s specifics.Know when to advertise. Only run ads if you’re ready to handle 10-15 new customers; otherwise, refine your processes first.Distribution is the multiplier. Even average people, processes, or products can succeed with great distribution, as Skip notes: “Advertising is just simply a way to cheat at distribution.”Start simple. Write down who you want to reach, what you want them to do, and what to say to make it happen—this clarity drives effective campaigns.Skip’s blend of practical tactics and principled leadership makes this episode a must-listen for entrepreneurs seeking to turn advertising into a predictable engine for growth, while staying grounded in responsibility to their community and planet.

Ciaran Burke is the co-founder of Swoop, and we spoke about the real pain points business owners face when trying to access finance—and why so many are stuck in outdated assumptions. With over 250,000 businesses using their platform across multiple countries, Ciaran has seen firsthand the huge shift in how funding works today.We discussed why access to capital is still one of the most intimidating and misunderstood parts of running a business—even though there are more options than ever before. As Ciaran puts it: “There's such stigma that money equals bank... Whereas actually today it's quite far from the truth.”Some key themes from our conversation:How funding myths are hurting businesses. Many founders still believe banks are their only option. But as Ciaran says, “If the bank says no, it can completely just wipe away that option to access funding or to grow.”Getting smart with your numbers. Business owners don’t need to become accountants, but they do need to understand what lenders see. Connecting accounting tools and getting a clear credit picture is the first step to discovering what’s truly possible.A new way to save and fund at the same time. Ciaran shares a sharp example where a business was rejected for a loan—until his team recalculated their expenses. By switching FX providers and energy suppliers, “the repayments on the loan were the exact same amount as what we'd saved them.”Why chasing VC money too early might be a trap. Founders often obsess over big investment rounds—but, as Ciaran says, “It can take a humongous amount of time out from growing the business.”Respecting time and automating the grind. Business owners are time-poor. Swoop’s philosophy? Use existing data, avoid repeating forms, and get money moving fast. Sometimes even “within 24 hours they'll have dollars in their bank account.”From equity to lending, grants to cash flow tricks, this episode is packed with practical insight—and a few hard truths—for anyone trying to build and fund a business today.Key takeaways:Don’t stop at the bank’s “no”—there are more funding doors than ever.Your financial data is your superpower—use it to unlock options.Equity isn’t always the answer—sometimes smarter borrowing wins.Speed, flexibility, and automation are now part of modern finance.A good funding decision starts with understanding your real position.This one’s for the founders juggling ambition, reality, and that eternal question: “How do I get the money I need—without losing control?”

Tim Dwyer is a business growth strategist, mapping expert, and lifelong entrepreneur—and we spoke about how emotions, structure, and purpose come together to shape the real journey of scaling a business.Tim’s approach to growth is anything but traditional. Drawing inspiration from the book Longitude, he compares the evolution of business navigation to the leap forward in oceanic travel during the 1700s. “Business mapping has been pre-1700s,” he says. So, Tim spent 25+ years creating what he calls a Google Maps for business—a framework that guides founders through the emotional, spiritual, and structural dimensions of growth.We explored what really causes stress, frustration, and anxiety in business—and how those emotions are signals, not problems. “Emotions are our compass,” Tim explains. “Anxiety is a fear of future… frustration is usually a capability gap.” His message? Learn to read these signals and your business roadmap becomes clearer.We also unpacked how many businesses lose momentum when they scale too fast, bring in misaligned hires, or drift from their original purpose. Tim shared the common pattern: “They attract a whole lot of people that want to be part of the journey… but if they’re not aligned to the brand vision and culture, drama sneaks in.”Key takeaways:Emotions are data: “If we're continually stressed, we haven't dealt with the issue.” Learning to interpret your emotional responses helps prioritize what to fix next.Purpose first, profit follows: “When we start with purpose… sales activity becomes almost effortless because we're being our authentic selves.”Don’t outsource leadership too early: “Learn how to lead through culture and capability so you don’t have to have that drama come into your business.”Mapping growth means seeing the whole journey: Tim’s system breaks down the stages from solo entrepreneur to 30+ team members—and helps you prepare before hitting a wall.Whether you're building a lifestyle business or a $100M enterprise, this conversation offers a recalibration—away from hustle and chaos, and toward a business that flows with your purpose, your team, and your life.

Zee Cohen Sanchez is the founder of Sole Strategies, a political consulting firm that thrives on grassroots engagement and movement-style campaigns. We spoke about the future of the Democratic Party, the lessons learned—or not learned—from recent elections, and how grassroots strategies can reignite voter trust and participation.Zee shares her entrepreneurial journey, starting with the decision to leave her union job, live in a 1984 RV, and launch a woman-led political organization. “We did over a million dollars in our first year because we sold our dream, vision, and ourselves,” she recalls.Key highlights from this conversation include:The importance of authentic grassroots outreach: “Advertising and mail are just a very impersonal touch. Real conversations with American voters are what matter.”Why the Democratic Party must embrace populism: “Their biggest fear is us running a populist candidate… because they know that if we start actually offering something of substance, they’re in trouble.”Building a sustainable entrepreneurial model: Zee emphasizes hiring for attitude, not just experience, and creating consistent connection calls to fuel growth.Zee’s insights aren’t just about politics—they’re a masterclass in resilience, strategy, and finding your unique voice in any field. Whether you’re a budding entrepreneur, an activist, or simply curious about what it takes to win, this episode is packed with actionable wisdom and inspiration.Takeaways:Grassroots matters. Talking to voters, especially in rural areas, is vital for meaningful engagement.Focus on the pain points. “You’re not selling services—you’re selling yourselves.”Be selective. Hire and work with people who align with your vision, and say no to those who don’t.Ready to take the leap? Follow Zee’s advice: “The perfect time to get involved is now.”

Toby Potter is a seasoned real estate investor and lender with 30 years of experience, having navigated the 2008 crash, the COVID-19 turmoil, and beyond. We spoke about the challenges real estate investors face today—sky-high interest rates, inflated property valuations, and a housing shortage of over 6.5 million units nationwide. Toby shares battle-tested strategies for finding off-market deals, negotiating distressed properties, and building long-term wealth through smart portfolio growth.What stands out most is Toby’s emphasis on turning obstacles into opportunities. He recounts buying a 94-unit complex in Longview, Texas, for just $5,000 out of pocket by assuming a distressed seller’s note, then securing a million-dollar line of credit for rehab. “We bought a three million dollar property for five thousand dollars,” he reveals, showcasing how to spot value where others see problems. His approach—combining meticulous due diligence, creative financing, and a focus on high-demand areas—offers a roadmap for success in a fickle market.You’ll learn how to avoid common pitfalls, like chasing Zillow listings where “7,000, 10,000 other investors have already looked at that property and walked away.” Toby stresses the power of off-market deals: “You have to find the deals before everybody else finds them.” He also dives into balancing short-term flips for cash flow with long-term holds for generational wealth, cautioning, “If I went back to 1994… and I still had all those properties… I’d be worth probably four or five billion dollars easily.”Key Takeaways:Find Off-Market Gold: Skip Zillow and realtor.com; leverage relationships and brokers to uncover distressed, unlisted properties.Negotiate Like a Pro: “We point out all the problems… that tells the seller, ‘Oh, crap, I got more problems than I thought I had,’” driving prices down.Build for the Future: Mix flips for quick cash with rentals for equity growth—buy in high-demand, expanding areas like Atlanta or McKinney, Texas.Stay Resilient: Toby’s secret to success? “Never, ever, ever give up,” but stay spiritually, mentally, and physically strong to weather life’s storms.Life-Changing Perspective: Real estate isn’t just profit—it’s freedom. Toby’s shift to this industry let him prioritize family, from selling a company to be with his daughter to cherishing grandkids today.Toby’s journey—from losing millions in 2008 to rebuilding and thriving—pairs practical tactics with a heartfelt why: creating a legacy for family and financial freedom. His book, The Unshakable Self, ties it all together, urging you to build a foundation to tackle any challenge. Whether you’re lost in today’s market or aiming for a richer tomorrow, this conversation equips you to grow, adapt, and win.

Jack and Jill Johnson are founders of The Franchise Insiders, seasoned franchise owners and consultants who transitioned from corporate burnout to entrepreneurial success. We spoke about their journey from a pivotal New Year’s Eve decision to sell their house and quit their jobs, to building and scaling franchises, including a home health care company that grew from two to 120 locations. They shared insights on navigating the franchise landscape, the importance of aligning a franchise with personal goals, and avoiding common pitfalls in the process.A key focus was their three-step process for helping aspiring franchise owners: understanding personal motivations, identifying the right franchise category through data-driven psychological modeling, and thoroughly vetting franchisors and franchisees. Jack emphasized, “It’s not just about making money, of course we all want to do that, but it’s about partnering with a company that can teach you to be a great business owner.” Jill highlighted their tailored approach, noting, “We’re not just showing you things that we think would be great. They’re actually very tailored and personalized to you specifically.”From my perspective, the most critical insight is their emphasis on “boring businesses” as resilient investments. Jack’s advice, “Do I need it if the economy’s bad? Will I pay for it?” underscores the value of franchises that provide essential services, like home health care or restoration, which remain in demand regardless of economic conditions. Their candid warning about the oversaturated market—“There’s like 3,000 franchises on any given day. Here’s the brutal truth. Most of them are junk”—is a wake-up call for thorough due diligence.Another standout topic was the role of strong branding and marketing support from franchisors. Jill’s marketing expertise, honed at companies like IBM and Wynn Resorts, informs their focus on franchises with robust lead-generation systems. “What you want to hear from existing franchise owners is we get 1, 2, 3, 5 leads a day from our franchisor,” Jack explained, highlighting how this support eases the burden on new franchisees.Key Takeaways:Start Slow, Scale Smart: Avoid overbuying territories initially. “Spend less money on franchise fees in the beginning, put more money into working capital,” Jack advises, to ensure financial stability.Data-Driven Decisions: Their AI-powered tools and territory analysis help match clients with franchises where they’re likely to excel, preventing costly missteps like poor territory selection.Boring is Profitable: Focus on essential, recession-resistant businesses rather than trendy franchises like fitness or fast food, which may falter in tough times.Franchising as a Learning Path: Franchises teach systemization, equipping owners with skills to scale or even create their own businesses later, as Jack noted, referencing The E-Myth Revisited.Jack and Jill’s blend of personal experience and industry credibility—they’ve helped over 600 people become franchise owners and earned top accolades in 2025—makes their advice both practical and inspiring. Their story proves that franchising isn’t just about buying a business; it’s about building a legacy with the right guidance.

Chris Tripoli is a seasoned hospitality industry veteran with over 45 years of experience as a concept developer, owner, operator, and consultant. We spoke about the magnetic pull of the restaurant industry for entrepreneurs, the critical elements of building a successful restaurant, and the common pitfalls that can derail even the most passionate dreamers. From navigating tight margins to understanding the importance of community engagement, Tripoli shares hard-earned wisdom from his decades of opening over 100 restaurants across the globe.The discussion highlights the paradox of why so many entrepreneurs, even those successful in other fields, are drawn to the high-risk, low-margin world of restaurants. Tripoli notes, “More and more small business entrepreneurs are drawn to this industry to open up their first business,” despite the competitive landscape and financial challenges. He emphasizes that success isn’t about a single recipe or nostalgic vision but about meticulous preparation and execution. “It costs a lot more than you think to open up a small business,” he warns, describing the industry as one where you “invest dollars to chase dimes.”A key takeaway is Tripoli’s formula for success: people, product, and processes. He stresses, “If you don’t have the right people around you, if you haven’t engaged the right investors, if you haven’t selected the right partners, then we have a lot to work on.” This people-first approach, coupled with a differentiated product and consistent processes, forms the backbone of a profitable restaurant. He also underscores the importance of knowing your core customer, using the metaphor of a dartboard: “It isn’t good enough to just be able to hit the dartboard. We must make sure that we’re hitting the bullseye.” This means tailoring every aspect of the business—menu, ambiance, and marketing—to the customer, not the owner’s personal tastes.What stands out most is Tripoli’s passion for mentoring and learning, even after decades in the field. He credits his first manager, Ray Nardoni, for sparking his career at age 15, and he continues to pay it forward through his work with restaurantowner.com and the Corner Booth podcast. “I learned the importance of mentoring,” he says, a principle that shapes his approach to helping family-run businesses navigate the unique challenges of accountability and dynamics.Key Takeaways:Preparation is everything: Success requires the right team, a differentiated product, and consistent processes to survive the industry’s tight margins.Know your customer: Design your restaurant for your core demographic, not your personal preferences, to hit the “bullseye.”Community matters: Engage with local causes to build a brand that resonates, as “people really like doing business with people they like.”Experience the grind: Work in a restaurant to understand its chaotic reality before investing your savings.Mentorship drives success: Whether in family businesses or startups, guidance from experienced leaders can make or break a venture.This episode is a masterclass for anyone dreaming of opening a restaurant, offering a candid look at the risks, rewards, and relentless effort required to thrive in an industry where passion alone isn’t enough. Tripoli’s stories—from mentoring young entrepreneurs to opening restaurants in the Middle East—make it clear why he’s still hooked on the next challenge, and why listeners will be too.