21st Century Entrepreneurship

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.

Kenny Ridgell is a serial entrepreneur who traded his biochemistry degree for a mission to help Main Street businesses thrive in a digital world. We spoke about his journey from a college app idea to running multiple ventures, including a trash company that turned a $10,000 investment into $100,000 in six months. The conversation unpacked how he uses data-driven strategies and AI tools to cut through marketing noise, target high-value customers, and tie every dollar spent back to measurable revenue.What stands out most is Kenny’s relentless focus on efficiency and impact. He’s not here to waste time or money—his own or anyone else’s. “You cannot take something and spend money and not know where it goes,” he says, a lesson forged from bootstrapping startups where every penny counts. His approach flips the script on traditional marketing: no retainers, no long-term contracts, just results that make you want to “cheers in 10 years.” It’s about building trust through proof, not promises.There’s plenty to learn here, especially for business owners drowning in marketing options. Kenny breaks down how tools like StackAdapt, GoHighLevel, and CallRail can pinpoint your ideal customer—think HOA board members or luxury homeowners—and hit them with precision across video ads, emails, even digital billboards. “Your ads are only going to work as good as your data performs,” he notes, emphasizing the power of refreshing data to stay ahead of competitors. He also reveals how AI can redesign your website based on real user behavior, turning clicks into conversions.A few takeaways pack a punch: First, test your strategies with your own money before scaling—Kenny does it with every new idea. Second, focus on the “three H’s”—healthcare, hospitality, and home services—to tap into high-net-worth clients with disposable income. Third, timing is everything; hit customers when they’re ready, not six months late. His story isn’t just about profit—it’s about purpose. “Nothing makes you want to wake up more than seeing your client go from a one-room shack to a multimillion-dollar home,” he says, a reminder that business can be a vehicle for generational change.This isn’t marketing jargon for the sake of it—it’s a blueprint for cutting waste and building wealth, delivered with the passion of a guy who’s lived it. Whether you’re a small business owner or just curious about smarter growth, Kenny’s insights offer a fresh, no-nonsense take on making data work for you.

Minal Joshi Jaeckli is a global citizen with a remarkable journey—born in Africa, raised in Georgia, and now a Swiss passport holder—and the author of The Goldilocks Team: Master Retention and Hiring. We spoke about the elusive art of employee engagement, the real cost of turnover, and why so many retention strategies miss the mark. With a background spanning chemistry, semiconductors, and financial services, Minal brings a unique, analytical lens to a deeply human problem: how do you build teams that stick around and thrive?The most striking takeaway is how universal yet misunderstood disengagement is. As Minal notes, “Gallup says around 20%, if not less of the world’s population is engaged. So what about everyone else?” This isn’t just a feel-good topic—it’s a bottom-line issue. She reveals that replacing an employee costs about 1.5 times their salary, a direct hit to any business. But beyond the numbers, it’s the ripple effect—frustrated teams, missed milestones, and clients who notice the chaos—that makes this so critical.What can you learn? Minal dismantles the myths of trendy retention tactics (think sushi Fridays or dog-friendly offices) and legacy guesswork, arguing they’re “illogical” and often irrelevant. Instead, she zeroes in on basic human needs—safety, connection, contribution—as the bedrock of engagement. “Employees are engaged when their basic human needs are met,” she says, tying it to frameworks like Maslow and Ikigai. Connection, though, is the linchpin. She’s adamant it’s not about manager bashing—“It’s not the manager, it’s the relationship with the manager”—but about resonance, a two-way street where trust and collaboration flow.Her Goldilocks concept—finding the “just right” fit—offers a fresh take on hiring and retention. It’s not about mini-me teams or forcing change; it’s about alignment. “All of us think the way we do it is right,” she quips, highlighting how mismatched work styles (like her “military” precision clashing with chronic tardiness) erode trust and productivity. Her practical tool? A simple assessment to gauge values and interpersonal fit—think of it as a weather app for team dynamics.Key Takeaways:Turnover’s True Cost: It’s not just money—1.5x salary—but lost credibility and client trust.Connection is King: “When you have someone who is not supporting you… people run out the door.”Ditch the Trends: Retention isn’t about perks; it’s about meeting core needs like safety and meaning.Goldilocks Fit: Hire for capability and alignment, not just attitude, to build teams that click.This conversation is a wake-up call for anyone leading a team. It’s not about grand gestures or corporate platitudes—“we are like a family” emails that turn sarcastic post-layoffs—but about getting the basics right. Minal’s blend of data, personal anecdotes, and no-nonsense insights makes this a must-listen for turning disengaged workers into loyal, high-performing teams.

Don Finley is a seasoned innovator, founder and CEO of FINdustries, with a decade of experience in artificial intelligence, holding a computer science degree from the early days of AI’s “winter,” when the math was ready but the tech wasn’t. We spoke about the transformative wave of AI sweeping through businesses, how it’s reshaping work, and why it’s a rare opportunity—akin to the dot-com boom or social media revolution—to ride rather than resist. “You can either get crushed by the wave of AI or you can learn to ride it,” he says, framing the stakes perfectly.The conversation zeros in on practical AI integration, from a “crawl, walk, run” approach—starting with treating AI as a team member, then building tools that know your brand, to finally handing off outcomes to AI agents. Don shares a jaw-dropping example: a 20-page market analysis for his real estate business, churned out by AI in 30 minutes, that once took weeks. “That would have taken a lot of back and forth, some drafts… but in 30 minutes, my partners and I were able to digest one of these reports.” It’s not just efficiency; it’s about freeing up space for what matters—relationships, strategy, and creativity, the trio he believes AI shouldn’t touch.What’s most striking is Don’s vision of work as play, inspired by Alan Watts: “The goal in life is to make your work look like play and so that nobody knows that you’re working.” AI, he argues, can strip away the mundane—think customer service bots or automated sales research—so you’re left with the fun stuff: connecting with people, dreaming up strategies, and chasing creative sparks. Yet, he’s candid about the flip side, noting how AI’s rise has slashed freelance jobs in writing and coding by up to 20% in a year.There’s a personal thread here, too. Don’s trek up Kilimanjaro revealed a deeper truth: “I’m the reason for my own dissatisfaction… That sunrise and all the people that I dearly love are on this journey with me and I can’t find a way to enjoy it.” It’s a raw moment that ties his entrepreneurial drive to a quest for purpose—one AI can support but never define. He sees entrepreneurship as “the best reflection of my own internal state,” a mirror that AI can polish but not replace.Takeaways:AI’s a wave worth riding—think of it as a teammate, not a threat, and start small.It can slash grunt work (e.g., a month-long project down to hours), letting you focus on the human stuff.White-collar jobs are shifting—copywriting and coding gigs are down, but individual output is soaring.Purpose matters more than ever; as Don puts it, “It’s more important that you understand at the core level what drives you.”AI won’t save you from yourself—use it to amplify, not escape, your unique value.Rethinking work, joy, and thriving in an AI-driven world goes beyond just tech. Don’s blend of practical know-how and soul-searching makes it a must-listen.

Lance Mortlock is a seasoned strategist with 25 years of experience, an adjunct professor at the University of Calgary, and the author of Outside In Inside Out and Disaster Proof. We spoke about the critical role of strategy in today’s unpredictable, fast-changing landscape, where leaders face unprecedented complexity—from tariffs and geopolitical shifts to climate change and digital transformation. Lance unpacks why a well-defined strategy, paired with relentless execution, is more urgent than ever, drawing from his global work with organizations and his research into emerging trends.What stands out most is Lance’s emphasis on execution as the linchpin of success. He warns, “Strategy execution failure is at 90%. So strategies fail mostly because we don’t execute them well 90% of the time.” This sobering statistic underscores his core argument: it’s not enough to craft a brilliant plan—you have to follow through. He also highlights the chaos of modern leadership, noting, “One in ten CEO appointments fail within the first two years. It’s incredibly hard to lead right now.” Amid this turbulence, Lance offers a lifeline: his diamond framework, a practical tool to balance external trends with internal strengths and drive results.We explored 10 megatrends shaping 2025 and beyond—like the 147 zettabytes of data created in 2024 (most of it unused), the $2.5 trillion invested in digital, and 2024 being the hottest year on record. These forces demand strategic clarity, yet Lance points out common pitfalls: “We spend too much time emphasizing strategy development but not enough time on execution.” His framework—outside in, inside out, prepare to execute, and execute—cuts through the noise, offering a roadmap for leaders to navigate risk and uncertainty.Takeaways? First, speed trumps size—Lance echoes Rupert Murdoch: “The big will not beat the small anymore. It will be the fast beating the slow.” Second, talent is non-negotiable; he’s shocked that “only 36% of organizations have a talent management strategy,” given people bring plans to life. Third, simplicity wins—strategy must be clear so “employees understand, remember and believe in it.” This conversation is a wake-up call for anyone steering a business through today’s stormy waters—strategy isn’t optional, and execution is everything.