21st Century Entrepreneurship

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.

Dianna Anderson is the co-founder and CEO of Cylient, and we spoke about the transformational power of everyday conversations—especially in moments when tensions rise, perspectives clash, or change feels impossible.What if the greatest skill for leading change isn’t strategy or planning—but the ability to talk with each other? Dianna argues that in today’s complex world, “our old approaches to having conversation are very conflict-based… and as a result, we all lose.” Drawing from decades of coaching experience and her development of the Untying the Knot® method, Dianna shares how teaching people to pause, get curious, and coach in real time unlocks shared insight, trust, and forward motion.At the heart of her message is a profound simplicity: “A knot’s just something that’s not happening.” And when we learn to recognize and unravel those knots—in thinking, in relationships, in leadership—we create space for learning and progress. With over 55,000 people trained in her “coaching in the moment” approach, Dianna shows how scalable, human-centered tools can shift entire organizational cultures.We also spoke about why traditional leadership models are failing, how assumptions from the last century hinder progress, and why conversation is the foundational skill of our era. “Our ability to have meaningful conversations with each other is the cartwheel of our moment,” she says. “And the better and the stronger our ability is to talk with each other, the more we can build upon that skill.”Key takeaways:Coaching is not just for coaches: Anyone can learn to use “in-the-moment” coaching tools to build bridges, not walls.Conversations are how change happens: “If you can't talk about something, you can't change it.”Modern leadership requires new language: Today’s complexity demands collaboration, not command.Untying the Knot is scalable: “There’s got to be a way that everyone could learn this… anywhere, at any time, in any conversation.”This episode is a must-listen for anyone who feels stuck in repetitive conflicts, overwhelmed by change, or curious about how simple shifts in dialogue can spark real transformation. Are you ready to untie your own knots?

Brian Bentow is a serial entrepreneur whose most important venture began not in the boardroom—but in the kitchen. He is CEO & Co-Founder @ Get Saucy. We spoke about his personal journey of reversing Crohn's disease symptoms through food, why he rejected conventional treatment, and how this led him to a deeper mission: making medically tailored meals accessible, sustainable, and delicious for people with autoimmune and food sensitivity conditions.What happens when modern medicine offers prescriptions, but not root causes? Brian's story begins with a diagnosis, a tearful colonoscopy photo, and a commitment: “I just wept… and I felt a determination to not only heal from this, but to be healthier than I ever was before.” Rather than accept long-term pharmaceutical treatment, he took a different route—a strict autoimmune protocol (AIP) diet that radically changed his life. “Once I was 100% compliant with the diet, the results were dramatic and almost immediate.”We explored what most people misunderstand about diet and chronic illness, why functional medicine still sits outside the mainstream, and how cultural myths about food are harming us. Brian also challenges the status quo in culinary culture: “My doctor said, ‘If you had these results and you were on medication, I would be ecstatic.’ And I said, ‘No medication.’”But this isn’t just a health story—it’s a startup story. Brian’s transformation led to his next business: solving the very problem that once overwhelmed him. “I had more discipline than most… but my daughter can’t force herself to eat food that doesn’t taste good.” This emotional trigger, combined with the challenge of making flavorful AIP-compliant meals, eventually led him to partner with a Michelin-trained chef and reimagine allergy-friendly cuisine. His goal: help people with autoimmune diseases have a seat at the table—without sacrificing flavor or health.Key Takeaways:The Power of Elimination Diets: “All my symptoms resolved and my inflammation went down by over 90%.”The Blind Spot in Medical Training: “In 40 years of practice, only one other patient had results like yours. But I don’t recommend the diet to anyone—because it’s not sustainable.”Root Causes, Not Band-Aids: “If I had been diagnosed with celiac, he would have told me to stop eating gluten. But for Crohn’s, only meds were offered.”Culinary Innovation Meets Medicine: From chicken tikka masala without nightshades to tomato-free marinara, Brian is creating sauces that heal as they delight.Mission-Driven Fulfillment: “Fulfillment is the hardest problem to solve. You can’t buy it. You have to earn it every day.”If you’ve ever wondered whether food could truly be medicine—or if you've struggled with restrictive diets and felt alone—this episode will not only give you hope, but show you what’s possible when determination meets innovation.

Dan J. Berger is the Founder and CEO of Assemble Hospitality Group and the author of The Quest: The Definitive Guide to Finding Belonging. We spoke about how early life traumas, entrepreneurship, and the deep human need for connection shaped both his personal journey and his professional mission.Dan revealed that building his multimillion-dollar company wasn’t a story of youthful ambition — it was a survival strategy: "Starting my company was a way to really address my lack of belonging." Yet selling it forced him into a painful but transformative realization: "Operating the business was me running away from doing the work on my own."We explored the idea that true belonging isn't found in success or status but in how intentionally we build and nourish relationships. Dan introduced his powerful framework of belonging archetypes — like the anxious meerkat or the secure chimpanzee — and explained how different people need different "belonging fuels" to feel whole: "There are specific things we can do in order to fill our belonging tank, depending on what our belonging personality is."This conversation opens up crucial lessons for entrepreneurs, leaders, and anyone feeling a hidden emptiness beneath external achievements:Why personal belonging must come before professional belonging — and how failing to do so quietly erodes leadership impact.The six types of belonging fuels — from interpersonal relationships to symbolic bonds — and how to consciously fill your emotional tank.How to build cultures of true belonging at work without mistaking it for box-checking diversity initiatives: "Belonging is a feeling and experience someone has when they feel seen, heard, and valued."The real reason many entrepreneurs experience a profound sense of loss after an exit — and what steps to take before reaching that point.Today, Dan’s mission through Assemble Hospitality Group is to create spaces where teams can reconnect, collaborate, and experience real belonging — not just at work, but in life. His book, The Quest, and free belonging archetype quiz offer a practical roadmap for anyone ready to stop outsourcing fulfillment and start building it within.

Julio G Martinez-Clark is a pioneer in the world of clinical research for medical devices, and we spoke about why so many American innovations never get tested on American soil first. As the founder and CEO of Bioaccess, the only U.S.-based CRO dedicated to first-in-human trials in Latin America, Julio brings an insider’s perspective on how to save medtech startups from trial-related dead ends.Did you know that most U.S. medical device startups look outside the U.S. to test their innovations first? “Because the uncertainty of the FDA, the difficulty of recruiting patients, and the costs associated with these trials force these companies to go overseas,” Julio explains. The destinations? Colombia, Panama, Dominican Republic — not just for affordability but for speed. “The savings in time and cost in Latin America can be substantial—about 70% faster approvals and up to 70% cost savings.”We explored:Why the FDA approval timeline is a bottleneck for startupsHow Latin America became the "go-to destination" for first-in-human trialsWhat makes sites in Colombia, Chile, Panama, and the Dominican Republic so attractive for medtech foundersHow Bioaccess virtually recruited and treated patients during the pandemic when U.S. teams couldn’t travelWhy speed-to-data is the lifeline for medtech companies with impatient investorsJulio also shared how his team built a 20-year legacy out of a University of Miami spin-off, backed by world-class cardiologists like his brother Pedro Martinez-Clark and mentor Dr. William O'Neill. “We were able to set up different cameras in the operating room… so the team from different parts of the United States via Zoom was able to guide the local investigator.”Takeaways for founders and innovators:You don’t need to wait 12 months for a greenlight when you can have it in 30-60 days.Latin America offers “geographical proximity, same time zone, and also because it's a lot faster and easier and cheaper to recruit patients.”Remote trials are real: "We recruited over 30 patients this way, actually.”If you're developing a breakthrough medical device and can't afford a year-long waiting game, this episode is a must-listen.

Nick Halaris is an entrepreneur, writer, real estate investor, and engaged citizen. We spoke about what it truly means to be successful in today’s world — not just financially, but morally, socially, and personally.What starts as a pursuit of the American dream evolves into something deeper: a mission-driven philosophy of ownership, contribution, and integrity. Nick walks us through the three distinct phases of his entrepreneurial journey — from chasing wealth, to redefining success, to building a life of meaning.“The American dream without a moral bedrock and without a mission is kind of empty.”This conversation explores his work with Profit Plus (his newsletter), The Nick Halaris Show (his podcast), and his real estate firm, but more importantly, it highlights how modern entrepreneurship can thrive when aligned with values, service, and community impact.Key insights from our conversation:Ownership is essential: “The tax code is structured to favor people who are owners... the capitalist system is wildly skewed to favor people who are owners.” Whether it’s owning a business, shares, or a home, Nicholas argues ownership is the clearest path to empowerment in a capitalist system.Value over extraction: “You have to contribute more than you extract.” Capitalism and nature share a common truth — sustainability is built on generosity, not greed.The real freedom? Time and service. “Just because you're free, it doesn't mean that you should pursue only what makes you happy… doing for others is a fundamental part of freedom.”Citizenship is a daily act, not just a vote: From homelessness to justice reform, Halaris reminds us that real civic responsibility requires action. “If you see suffering in the world, do something about it.”Learn from Nick how:You can build wealth without compromising your soul.Success evolves through self-awareness, mission, and contribution.Political disengagement is not a neutral stance — it’s complicity.Owning your path means taking responsibility for more than just your outcomes.An episode for anyone asking not just how to win — but how to win the right way.

Bill Wilson is the CEO of Pace Pricing and a seasoned expert in B2B SaaS pricing, having coached over 400 companies to refine their monetization strategies. We spoke about the art and science of pricing, unpacking how it’s less about picking a number and more about aligning with customer value. From overcoming founders’ pricing anxieties to crafting effective packaging models like good, better, best, Bill shared actionable insights grounded in data and customer understanding.The conversation illuminated why pricing is a powerful growth lever. Bill emphasized, “Pricing isn’t about how much you charge, it’s about how you charge,” highlighting the need to focus on packaging and value delivery over arbitrary price points. For SaaS founders hesitant to tweak pricing, especially for existing customers, he offered a clear path forward: use data to build confidence. “The best way to build confidence in your pricing is through data,” he said, advocating for analyzing customer usage, segmentation, and jobs-to-be-done to create a pricing strategy that feels natural and defensible.We explored various pricing models—good, better, best, use-case-based, and platform-plus-extensions—and their fit for different customer sophistication levels. Bill cautioned against over-relying on per-user pricing, noting, “Per user is a bit dangerous… we are essentially tying our product to our customer’s most expensive resource, which is hiring a new person.” Instead, he championed hybrid value metrics, like the number of appointments in a booking software case study, which led to a 25-30% ARR increase for one client.What stood out most was Bill’s practical, step-by-step approach to pricing projects: start with subscription and usage data, talk to customers, map jobs-to-be-done, test pricing sensitivity, and validate with both existing and new customers. His advice to “use the data you have” and avoid chasing perfect information was a refreshing nudge to action. For founders stuck in pricing paralysis, Bill’s message is clear: “When it’s done, every founder I’ve ever worked with has always said it was worth it.”Key Takeaways:Value Over Numbers: Pricing should reflect the job your customer hires your product to do, not just a dollar amount.Data-Driven Confidence: Use subscription and usage data to craft a pricing strategy that reduces anxiety and aligns with customer needs.Smart Packaging: Good, better, best works for most SaaS companies, but consider use-case or extension models for complex or enterprise clients.Value Metrics Matter: Move beyond per-user pricing to capture value tied to usage, like appointments booked, to drive revenue growth.Test and Talk: Validate pricing changes with customers—new and existing—to ensure acceptance and minimize churn.Bill’s insights are a masterclass in turning pricing from a nerve-wracking gamble into a strategic asset. Whether you’re a SaaS founder or a pricing enthusiast, this episode offers a blueprint to “install good pricing practice” and unlock growth.