21st Century Entrepreneurship

Michael Shaw, Founder of the Mastery Mindset Library, is a seasoned entrepreneur and the visionary behind a transformative mindset framework designed to help high-performing professionals thrive under pressure. In our conversation, we explored his journey from building and selling successful fitness businesses to confronting personal crises that reshaped his understanding of success. We discussed the emotional toll of entrepreneurship, the pitfalls of outdated belief systems, and his practical approach to building emotional resilience. Shaw shared his four-pillar framework—awareness, rewiring, alignment, and activation—that empowers entrepreneurs to rebuild their internal foundations and achieve true balance in life and business.What stands out most is Shaw’s raw honesty about the hidden struggles entrepreneurs face. He dismantles the myth of the invincible hustler, revealing how “we hide our anxiety behind hustle and we mask our burnout with bravado.” His story of turning a personal breakdown into a breakthrough—sparked by the question, “What if I could train my emotional resilience the same way I trained my body?”—is both inspiring and actionable. This episode is a wake-up call for anyone chasing success at the cost of their mental and emotional well-being.Shaw’s insights are grounded in real-world experience, from overcoming divorce, financial strain, and his father’s suicide to redefining success as “living a life that actually feels good to wake up to.” He emphasizes that “your business can only grow to the level of your mindset,” urging entrepreneurs to move beyond time management hacks and focus on internal growth. His simple yet powerful technique of pausing to ask, “What’s the story I’m telling myself right now?” when facing setbacks offers a practical tool for reframing challenges and building emotional fitness.Key Takeaways:Redefine Success: Success isn’t about vanity metrics but alignment with your values—peace, purpose, love, and freedom. As Shaw puts it, “Real success is alignment. It’s having the courage to build a life that matches your values, not just your vanity metrics.”Emotional Fitness is Trainable: Just like physical strength, emotional resilience can be built through consistent practice. Shaw’s advice to pause and reframe your narrative during setbacks—“Is this story useful? Is it helping me move forward or keeping me stuck?”—is a game-changer.Mindset Over Hustle: Entrepreneurs often operate from fear-based belief systems rooted in perfectionism or survival. Shaw’s four-pillar framework helps identify and replace these limiting beliefs to unlock true potential.Accessibility Matters: Shaw’s commitment to making mindset tools affordable through a scalable, on-demand platform reflects his belief that transformation shouldn’t be locked behind high price tags. He challenges the status quo, noting, “Countless coaches offering to teach you their proprietary success method for 30, 50, even 100 grand… that just doesn’t sit well with me.”This episode is a must-listen for entrepreneurs and high achievers seeking to break free from the cycle of stress and isolation. Shaw’s blend of vulnerability, practical strategies, and a no-nonsense approach to mental conditioning offers a roadmap to not just survive but thrive. Learn how to catch your stories, choose empowering ones, and build a life where you lead, love, and live with clarity and calm.

Patrick Pychynski, Founder of Stacking Capital, empowers entrepreneurs to scale with zero percent interest funding, and we discussed how to access $50,000 to $250,000 without harming personal credit. A former Marine and metal recycling entrepreneur, Patrick’s early struggles with a $20,000 debt that led to jail time inspired his mission. He shared his three-step framework: optimize credit, structure a compliant business, and apply to banks strategically. Unlike others, his approach uses a three Cs framework (credit, collateral, cash flow), as he noted, “One of the things that set us apart… is that we take a whole approach into your business.” Patrick emphasized long-term goals, moving beyond 0% funding to “bankable” businesses, and practical tools like Plastiq for vendor payments. His business success scan helps assess funding eligibility fast. “Everyone sort of gets a second chance when it comes to your credit,” he said, highlighting the power of rebuilding.Key Takeaways:Access Untapped Funding: A 700+ credit score can unlock $50,000–$250,000 in 0% interest business credit with minimal documentation.Protect Personal Credit: Business credit cards don’t report to personal credit, unlike personal cards that can harm FICO scores when maxed out.Strategic Application Matters: Applying to banks in the right order, considering bureau pulls and inquiry sensitivity, is critical for success.Think Long-Term: Build a “bankable” business to transition from short-term 0% funding to corporate credit with better rates.Leverage Tools: Use services like Plastiq to pay vendors with credit cards and offset costs with tax-deductible fees and card bonuses.This episode offers entrepreneurs a roadmap to scale smarter with Patrick’s proven insights, perfect for breaking free from high-interest loans or personal savings.

Julia Menez, founder of GeoBreeze Travel and a former actuary turned points-and-miles expert, joined us to share her analytical approach to mastering luxury travel without breaking the bank. We explored how business owners and high cash flow individuals can leverage credit card points to unlock premium international trips, from Emirates first-class showers to Singapore Airlines’ suites with separate beds. Julia breaks down her Business Class Blueprint, offering practical strategies to optimize expenses and book unforgettable travel experiences.The conversation highlights the pitfalls of common approaches, like chasing “shiny card syndrome” or relying solely on Google Flights. “A lot of people try following different tips on Instagram... but they’re still not getting the best deals,” Julia notes, emphasizing the need to work backward from your travel goals. She introduces tools like Points Path and Seats.Aero, alongside her counterintuitive advice to book from major hubs rather than home airports. “If I’m going to Asia, I’m searching out of Los Angeles, San Francisco, Seattle... Figure out a way to get over the ocean in a good business class deal,” she advises, revealing how a $100 positioning flight can unlock massive savings.What stands out is Julia’s focus on customization. Her one-on-one concierge service tailors strategies to individual needs, avoiding the generic deal alerts that force you to “fit your life around that deal.” She also champions diversity in the points-and-miles space through her GeoBreeze Travel podcast, featuring over 250 guests from varied backgrounds. “There’s no strategy that’s one size fits all,” she says, underscoring the importance of inclusive, mindset-driven approaches.Key Takeaways:  Start with your destination, not the card: Identify your travel goals and required points before applying for credit cards.  Use specialized tools: Platforms like Points Path and Seats.Aero outperform Google Flights for points-based deals.  Think beyond your home airport: Book business-class deals from major hubs and add cheap positioning flights.  Maximize points with transfer partners: Instead of cashing out points, transfer them strategically to get “five or ten times as many first-class flights.”  Personalization is key: Custom strategies beat generic deal alerts for aligning travel with your lifestyle.This episode is a goldmine for anyone overwhelmed by points-and-miles blogs or chasing outdated advice. Julia’s analytical mindset and real-world examples—like caviar on Emirates or Bulgari tote bags—make luxury travel feel achievable, proving you don’t need to spend $10,000 to live the high life. Check out her GeoBreeze Travel YouTube and podcast for more free tutorials and diverse perspectives on mastering the points game.

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.