21st Century Entrepreneurship

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.

Daniel Boettcher is a former diplomat-in-training turned luxury jeweler, whose remarkable journey from Yale’s PhD program to the Antwerp Diamond Exchange is driven by his ability to weave personal stories into bespoke jewelry. We spoke about his transition from diplomacy to crafting narrative-driven pieces, the psychology and anthropology behind his creative process, and how he transforms client interactions into wearable art.Boettcher’s story begins with a health setback that ended his diplomatic ambitions, leading him to a serendipitous encounter in an Antwerp cigar shop where a diamond dealer sparked his new path. His diplomatic training and psychological insight shine through as he designs jewelry that captures clients’ personal histories, like an engagement ring inspired by a couple’s love story in a Kansas sunflower field: “It did not feel like falling. It felt like remembering.” He explains, “I have to sit down with another human, and I have to find the space that the two of us touch each other,” emphasizing the deep listening that fuels his work.His refusal to quit—“For some reason I was not wired with the ability to quit”—underpins his success in the luxury market, where he navigates exclusivity and client privacy with finesse. Boettcher’s leadership, shaped by diplomacy, prioritizes understanding others’ desires: “You can really only lead people if you know where they want to go.” His vision extends to a cultural hub in a 500-year-old San Juan house, blending a jewelry workshop, bakery, and artistic institute to foster creativity and legacy.What’s most compelling is how Boettcher turns conversations into art, creating pieces that remind clients of their “creation story every day.” His process, from client storytelling to design briefs like “The Radiance of Sunflowers,” showcases a unique blend of empathy and craftsmanship: “I like to think that I can sell joy and I can even create joy where there was not joy before.”Key Takeaways:Stories Become Art: Boettcher’s jewelry transforms personal narratives into tangible legacies, making each piece a “narrative, memory and vow made visible.”Listening is Key: His success hinges on listening deeply—“taking the cotton from my ears and putting it in my mouth”—to craft meaningful designs.Grit Fuels Resilience: His persistence through adversity proves “it takes a long time to become an overnight success.”Luxury is Intimate: Privacy and personalization define his brand, catering to clients who value exclusivity and storytelling.Legacy Beyond Craft: His San Juan project aims to enrich culture, showing that luxury can “change a couple things” for the world.This episode offers a profound look at how empathy, resilience, and creativity converge to craft jewelry that’s more than adornment—it’s a celebration of human connection.

Cameron Bishop is a seasoned CEO turned investment banker, and we spoke about the hidden pitfalls that make otherwise successful companies unsellable—and what entrepreneurs can do to change that. With a track record that includes scaling a publishing company from $7 million to $400 million, acquiring 50 businesses, and helping private owners transition or exit, Cameron shares invaluable insights on building companies that are not just profitable—but also truly sellable.Throughout our conversation, Cameron reveals five recurring red flags that derail deals, from poor financial records to excessive owner dependency. He speaks candidly about his mission: “I just love helping business owners when they're ready to sell, to give them guidance and hopefully… get them the generational wealth that they hope to get.”Cameron’s stories—some painful, some triumphant—underscore the brutal realities of the lower middle market and the gap between what owners think their businesses are worth and what buyers will actually pay. As he puts it:“Somewhere around 70 to 80% of business owners who try to sell their company never sell their company.”Topics we covered include:Why so many $5M–$50M companies fail to close a saleThe shocking truth behind poor accounting—and how it masks real profitabilityThe dangers of customer and vendor dependencyHow gross profit margins can kill interest before a buyer even makes a callPersonal stories of lost deals, bad assumptions, and hard-earned wisdomTakeaways: ✔ Without accurate, GAAP-based financials, buyers walk away ✔ If your business can’t run without you, it likely won’t sell ✔ “Know what you don’t know—and find an expert to do it for you” ✔ Gross margin is a make-or-break factor for most buyers ✔ Selling your company isn’t just a transaction—it’s a strategic process years in the makingWhether you’re building to sell or just want to future-proof your company, Cameron’s insights will challenge how you think about valuation, succession, and long-term business health.

Dan Abel is the third-generation chocolatier and CEO behind one of America’s most storied confections legacies, Bissinger’s - and we spoke about legacy, leadership, and the bitter lessons that come with chasing sweet success.From sweeping chocolate floors as a child to navigating a multimillion-dollar expansion during the steepest cocoa crisis in modern history, Dan shares what it really takes to honor 350+ years of craftsmanship while facing today’s pressures of scale, automation, and authenticity.What happens when small-batch artisanship meets big-box temptation? How do you hold onto soul when speed and volume try to tear it away?“We thought we wanted to touch the sun… but we really didn’t. We wanted to make really small batch artisan chocolates.”We unpack how Dan’s family went from dreaming about massive wholesale contracts to walking away from robotic production lines—because even success can become a trap. With raw honesty, he reveals the emotional toll of high-speed growth, the cost of losing creative purpose, and the deep reset COVID unexpectedly allowed.And then there's the cocoa crisis. With cocoa futures spiking 3–4x historic highs, Dan offers a masterclass in principled pricing and long-term thinking:“Our customers are our family… If we have an extra $3 of raw materials in a gift box, we’re just going to raise the price by $3.”This episode also explores how Dan and his siblings—each leading different business pillars—built a rare family business culture that actually works.“At 12 o’clock every day, my brother, sister and I sit down and have lunch together... probably 245 days a year.”What you’ll learn:Why growth can be seductive—and destructive—without purposeHow to use crisis moments (like COVID or a global cocoa shortage) to reset your business modelThe difference between scaling for ego vs. scaling with legacyHow a 350-year-old heritage still shapes modern product decisionsWhat it takes to build a family business that thrives emotionally and operationallyWhether you're building a brand, wrestling with scale, or wondering when to double down, this episode is filled with hard-earned wisdom—plus a reminder that even in chocolate, not everything sweet is good for you.

Mollie Engelhart is a former vegan chef turned regenerative rancher, and we spoke about resilience, food sovereignty, entrepreneurship under fire, and why the future of sustainability might not be what you think.In this raw and powerful conversation, Mollie opens up about her journey from operating $7M vegan restaurants to raising cattle on a regenerative ranch. Her story is anything but ordinary—and challenges common narratives about climate, food, and business.She questions our dependency on outsourced food systems, warning:“We are a net importer of food, and if the supply chain gets messed up, then we starve.”From almost closing a $31M restaurant deal to losing it all during the pandemic, to confronting online activism that led to being "permanently closed" on Yelp, Mollie shows what it means to keep going when the world pulls the rug out.“There’s nothing worse than cashing out $200,000 of your retirement to pay final paychecks on a business that’s never going to monetize.”And yet, she rebuilt—again. This time on Sovereignty Ranch, where she’s creating something entirely new: a full-circle experience of regenerative living.We discussed:Why she abandoned the vegan movement despite being celebrated in itThe connection between microbiology in soil and human mental healthWhat entrepreneurs must understand about self-worth: “I have opened my bank account app and seen millions. And I have opened it and seen negative $7,000. But who I am doesn’t change.”You’ll also learn why radical faith, relentless action, and surrounding yourself with true believers are the pillars that helped her survive multiple industry collapses—from music to marijuana to restaurants.Key Takeaways:Regenerative agriculture isn’t just about food—it’s about national security, self-reliance, and soul.Entrepreneurship is spiritual: "You cannot put your worth on your bank account."Action beats planning: “So many great ideas die in the details.”Resilience is not the absence of fear—it’s doing the next thing despite it.This episode isn’t just a story. It’s a wake-up call.💡 "You lose everything, and then you try again. But that doesn’t mean you are less of a mother, wife, or child of God."Whether you're a burned-out founder, a conscious consumer, or someone questioning your impact—Mollie’s story will challenge and inspire you.

Dr. Sherry Peel Jackson is a former IRS agent, Certified Fraud Examiner, and CPA turned financial truth-teller—and we spoke about how to keep, protect, and grow your income in a system that’s designed to take it from you.Known for her unapologetic views on taxes (“I call the IRS the Insidious Representatives of Satan”), Dr. Jackson pulls back the curtain on how everyday individuals and business owners can stop “feeding the beast” and start building lasting wealth. This conversation goes far beyond budgeting—it’s about strategy, structure, and self-reliance.We explored practical, often overlooked methods for lowering expenses, avoiding common traps like conspicuous consumption, and using the tax code to your advantage. Her background at the IRS gives her a rare edge—and she's using it to empower people like you.💥 “It’s not about what you make, it’s about what you can keep.”Some of the key insights and quotes you'll hear:Stop bleeding money: “People spend millions on conspicuous consumption… and it keeps them broke, busted, and disgusted.”Think like the wealthy: “If you do what they do, you can have what they have.”Use your home strategically: “Have a home-based business and write off everything but the kitchen sink.”Leverage the Augusta Rule: Learn how corporations can legally pay their owners $22,400 tax-free just by using their home for meetings.Pay your kids—and win: “Teach them to make money work for them, not the other way around.”We also broke down the three pillars of her framework:Keep what you earn – Smart spending habits, reducing lifestyle inflation, and cutting sneaky costs.Protect what you earn – From insurance and lawsuits to the IRS and unexpected life events.Grow what you earn – By starting small businesses, owning assets, and learning from foundations that have lasted for generations.“Only the little people pay taxes,” she reminds us, quoting Leona Helmsley—not to provoke, but to highlight how financial systems are tilted toward those with information. Dr. Jackson’s mission is to balance the scales.