21st Century Entrepreneurship

Mark Murphy is a top-ranked financial strategist, best-selling author, and CEO of Northeast Private Client Group. We spoke about how entrepreneurs can move beyond just surviving in business to creating multi-generational wealth and a life by design.Mark breaks down the crucial difference between running a business for cash flow and building a business that funds freedom. As he puts it:“Everybody has two businesses—the one that pays the bills, and the one they wish they had.”We explored how to shift from reactive decisions to intentional bets, why true wealth is rarely built in the stock market, and how most business owners unknowingly “buy themselves a job” instead of building a scalable asset.Mark also shares timeless insights on leadership, culture, and team building:“You don’t grow a business—you grow people.” “Good leaders create followers. Great leaders create other great leaders.”From the difference between networking and net weaving, to why 5% of people are entrepreneurs (and why that number hasn’t changed in 50 years), Mark challenges conventional thinking while offering deeply practical tools.Key themes discussed:The three true engines of wealth (and why your 401k won’t cut it)Creating “transformational” vs. “transactional” relationshipsBuilding company culture that scales—and attracts top talentThe real reason top performers leave (it’s not the money)How to know when your current team or advisors have taken you as far as they canWhat it means to “play in a competition-free zone”Key takeaways:Don’t chase more revenue—chase the right bets and informed guesses.Focus on your clients’ needs by “asking the check writers” what they truly want.If someone can do their job better than you, you work for them.Culture can’t be outsourced—it must be modeled by the founder.The best way to retain talent? Let them own something.Mark’s philosophy is clear:“If you’re an expense, you’re always on the chopping block. But if you’re an investment, I have an unlimited appetite.”Whether you're scaling a business or building your legacy, this conversation is a roadmap to both financial and personal freedom.

Kevin McCarthy is President of Blind Spot Assessments and a CSP-certified speaking professional whose journey from entrepreneur to federal inmate reshaped his life's mission: helping leaders uncover the blind spots that sabotage success. We spoke about how high achievers—especially entrepreneurs and executives—can unknowingly make devastating choices while believing they're on the right path.Kevin shares the riveting story of how he went from leading the 13th-largest Century 21 franchise to losing everything in the dot-com crash, getting swept into the largest stock fraud in Washington state history, and ultimately serving 33 months in federal prison—not for what he knew, but for what he failed to see.“I was guilty. I just didn’t know in the context of the moment that I was helping him further a crime.”“Context is king… We don’t always take a moment to step back and evaluate the big picture.”We explored how blind spots form, how trust without scrutiny can backfire, and how entrepreneurs, in particular, are vulnerable due to high-speed decision-making and isolation. Kevin explained how self-deception distorts perception—and how true leadership begins with awareness and humility.“You think you know what you know. But you have to step back and ask: What else could be going on here?”He also shares how prison became his unexpected retreat—a place where he finally had space to reflect on identity, character, and purpose. The insight he gained led him to study cognitive psychology, create the Blind Spot Assessment, and now train others—especially middle managers and leadership teams—to build trust, engagement, and clear-eyed decision-making.Key themes discussed:The hidden cost of unexamined trustHow “perception gaps” sabotage teams and engagementWhy most people believe they’re self-aware—and aren’tThe danger of promoting experts into leadership without supportWhy skepticism isn’t cynicism—it’s self-preservationTakeaways:Blind spots don’t make you a bad person—they make you human. But they can still ruin your career if ignored.Asking better questions and surrounding yourself with truth-tellers is essential leadership hygiene.Self-awareness isn’t a given. “Only 10–15% of us actually are self-aware.”Leadership success depends more on managing perception than just performance.If you want to grow your team, start by growing your self-understanding.Whether you're an entrepreneur running at full speed or a leader wondering why your team’s engagement is slipping, this conversation with Kevin McCarthy is a wake-up call—and a roadmap.

Vanessa Joy is a photographer, creative entrepreneur, and mother of two—and we spoke about what happens when a relentless drive for business success collides with a long-buried childhood dream. Known for building multiple thriving businesses and being the primary breadwinner in her family, Vanessa shares how a spontaneous trip to Kenya reframed everything she thought she knew about fulfillment, purpose, and legacy.At the heart of this conversation is a bold emotional shift: from executing perfectly calibrated workflows to creating something that finally felt meaningful.“All I’ve been doing is building businesses and feeding my family, and yet this one thing I dreamed about as a child—I never did it.”We traced her entrepreneurial journey back to a rebellious teenage choice in a high school guidance counselor’s office—a reluctant decision to take photography to please her mom. That single act of people-pleasing set the foundation for five successful businesses.But the real turning point came much later, standing in a Kenyan village, camera in hand, realizing that the children she photographed lived without clean water—and without complaint.“There was a fly right on her eyeball… and the baby wasn’t even blinking. That’s when I realized—this isn’t fake. This is their life.”Vanessa speaks candidly about guilt, ambition, and the emotional armor many entrepreneurs wear. Her realization? Building businesses is not the end goal—it’s the vehicle for something greater. The trip inspired her to start a nonprofit, launch a fundraiser using her art, and finally fulfill her childhood promise to fund a well.“Maybe that was the goal the whole time… to build businesses so I could do the work I’ve always wanted to do.”Key themes we discussed:The emotional cost of ambition and high-functioning entrepreneurshipHow childhood dreams can quietly shape adult purposePhilanthropy through business: the power of anonymous givingTurning burnout into meaningful creationWhy success without emotional fulfillment often feels emptyKey takeaways:A powerful reminder that your most meaningful work may not feel “efficient”—but it will feel alive.Giving doesn’t have to be loud to be transformative.Your past (even your people-pleasing moments) can plant seeds for unexpected purpose.Systems and workflows build business freedom—but freedom is just the beginning.This episode is for anyone wondering whether chasing "more" is still serving them—or whether it’s time to make space for what truly matters.

Draye Redfern is a serial entrepreneur, marketing expert, and founder of Fractional CMO. We spoke about how most business owners aren't dealing with broken marketing—they're just missing clear visibility into what works. From attracting leads to building self-managing companies, Draye laid out the exact framework he uses with billion-dollar clients and mom-and-pop shops alike.The centerpiece of the conversation is his ANCHOR Framework—Attract, Nurture, Convert, Humanize, Optimize, and Retain—which acts like a set of “small hinges that swing big doors.” As Draye puts it, “You should be stopping the stuff that's not working… and doing more of what is.” This simple shift in mindset—paired with the right systems—can lead to radical improvements in marketing outcomes and overall business health.We also explored:Why consistency beats complexity in marketing (“You can make anything work—but only if you stay consistent.”)The power of humanized outreach in an AI world (“We’re now in an H2H world—human to human.”)The biggest invisible opportunities in business growth, including underused KPIs and neglected client retention strategiesWhy every business should be built as if it’s ready to sell—even if you never do: “That’s the type of company that any buyer wants to buy.”“Even some of the best private equity firms managing $20 billion are missing at least two parts of the ANCHOR Framework.”“Would you rather get a personalized video that says your name… or another generic ‘buy my stuff’ pitch?”Key takeaways:Attraction is not the problem—optics are. Most businesses rely on one lead source, usually referrals. Draye recommends 2–3 to escape the feast-or-famine cycle.Write 52 nurture emails once. Then automate. One per week for a year. Rinse and repeat.Conversion is more than a sale. Track the right 2–4 metrics—booked calls, opt-ins, and close rate are Draye’s personal drivers.Retention > new acquisition. It’s 5–25x cheaper to retain a client. Personal touches (like birthday notes via Handwritten.com) matter more than flashy funnels.Build a business worth selling. Not because you will—but because a self-running business is the most freeing one to own.From marketing clarity to life alignment, this episode is packed with tactical advice and grounded wisdom from someone who’s scaled to $40M+, sold to a Berkshire Hathaway company, and now builds businesses designed to serve, scale, and sustain.

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.