21st Century Entrepreneurship

Elliott Holland is a Harvard Business School graduate and veteran of small business acquisitions, and we spoke about why most aspiring business buyers never close a deal—and what you can do differently.With over 15 years in the trenches as a buyer, advisor, and coach, Elliott brings real talk to a world filled with overhyped promises and group-cohort gimmicks. “90% of business buyers never get a deal done. But that doesn’t have to be you,” he tells us. So what separates the 10% who succeed?We covered the messy reality behind the glossy dream: how corporate professionals earning $200–400K annually struggle to make the leap to business ownership, not due to lack of talent—but because they enter a completely new game without the right training, time, or tactical support.Key themes we explored:Why self-learning or group courses fall short when you're negotiating $3–7M dealsThe psychological leap from “safe employee” to “deal-making owner”Why mastering BS detection is more valuable than spreadsheetsThe brutal truth about due diligence, valuation, and seller gamesHow one-on-one coaching can compress 30 years of learning into 6 monthsAs Elliott puts it:“You don’t go from negotiating $20,000 salary bumps to $3 million acquisitions by reading a book.” “Everybody lies—and telling the truth can get you fired. This isn’t corporate America anymore.”He also shared a powerful story of one student who failed solo for 12 months, then bought a 7-figure company within six months of joining Elliott’s program—transforming not just their career, but their family legacy.Takeaways:Deal-making is a skillset, not a mindset—and most people are dangerously underprepared.You need 1-on-1 coaching to navigate the hundreds of nuanced, high-stakes decisions in a deal.Time is your enemy when you’ve got a family, a job, and one shot to make it work.Buying a business isn’t just about money—it's about freedom across generations.“This isn’t painting your room. This is a life’s work.”Whether you're a six-figure earner ready for your next chapter or just curious about the business buying journey, this episode offers a rare, honest look behind the curtain—and a roadmap to avoid joining the 90% who never make it.

Scott Desgrosseilliers, CEO of Wicked Reports, is a marketing attribution expert with over 25,000 hours in the trenches, and we spoke about the real reason most Meta campaigns fail, why AI is both a gift and a trap, and how his Scale, Chill, Kill framework helps marketers make better, faster decisions—without drowning in data.Scott has analyzed nearly 60,000 campaigns across 1,000+ advertisers. What he discovered flipped traditional attribution thinking on its head. “It wasn’t that we needed more data,” he said. “It was about knowing which signals are going to trigger alignment to what your strategy was doing and the results you were trying to get.”We explored:Why Meta’s AI favors retargeting and what that means for your long-term growthThe danger of relying on "last-click" logic in a world that demands first-click foresightHow to train AI platforms to prioritize new customer acquisition, not just bottom-funnel conversionsThe origin and power of Scott’s Five Forces Framework, inspired by reality creation: Intention, Expectation, Action, Outcome, OptimizationHow Wicked’s AI cuts through the noise by giving you “three bullets and an action step” for each campaign“There’s no one magic attribution model—depends on what you're trying to do.” “Marketers only care about data as much as it helps them make more money.”Scott also shared how the breakthrough wasn't more spreadsheets or better math—it was eliminating the time drag on creative marketers: “No one has two hours a day to look at attribution data. So we built a system that does it for you—and it’s actually better than me.”Key takeaways:AI is smart, but it needs direction. If you don’t signal what matters, it will default to retargeting—and your funnel will stagnate.First-click attribution is undervalued. It looks bad on paper, but it's critical for growth.Your measurement strategy must match your marketing intention. Misalignment leads to wasted budget and missed scale moments.Creative marketers need clarity, not complexity. Automation only works if it delivers insights in plain language, backed by evidence.If you’ve ever stared at your campaign dashboard wondering whether to spend more, shut it down, or just wait it out—this conversation will show you exactly how to decide.

Pasha Knish, CEO and Lead Strategist of AMZ Optimized, is a veteran Amazon seller and the founder of a boutique agency helping brands navigate the increasingly complex Amazon ecosystem. We spoke about what it really takes to succeed on Amazon today—and why many sellers are getting crushed by outdated strategies, poor infrastructure, or a fragmented team approach.With 14+ years of experience, Pasha brings clarity to the chaos of Amazon's ever-evolving landscape. Whether you're a new seller launching your first product or an established brand losing traction, this conversation unpacks the real playbook for sustainable growth.“Amazon is a place where both sellers that are completely brand new can exist as well as sellers that have been on the platform... but all sellers deal with the same problems.”We explored:Why having a fully optimized listing before running ads is non-negotiableThe power of pricing psychology: “Sometimes you actually sell more when you price higher.”How Amazon’s AI is now cross-referencing your website to verify your listing infoThe hidden costs of success: compliance, fees, logistics, and inventory flowWhy DSP (Amazon’s demand-side platform) and tools like DeepM matter for serious scalingThe myth of “set it and forget it” and why seller success requires ongoing partnership“This is not eBay. You want to make it easy for the customer and easy for yourself.”Key takeaways:PPC should never be your starting point. Nail your content, compliance, and pricing first. Inventory is your lifeline—“If you run out of stock, you lose all your momentum.”Being the cheapest doesn’t win—being the best value does. Boutique support can outperform internal hires or freelancers by aligning every moving part. Amazon may be templated—but real success is always custom.If you think Amazon success in 2025 is dead, think again. As Pasha puts it: “There’s still an opportunity... but it's getting eaten up little by little. You need to be smart, fast, and prepared.”

Israel Duran, founder of Israel Duran Associates, entrepreneur and "impact architect," shares his journey from losing his father as an infant to creating generational wealth. We explored three principles separating thriving entrepreneurs from those just getting by: the Principle of Conditions, the Principle of the Leak, and the Principle of Impact. These offer a roadmap for business owners and speakers to achieve lasting success.We discussed how past experiences can trap entrepreneurs, as Israel notes, “A lot of people… take the past and they try to portray it in the future and they get paralyzed.” Breaking free from these cycles is key to seizing new opportunities and avoiding stagnation.The Principle of the Leak highlights the need to fix business inefficiencies. Israel’s analogy of a leaky container is powerful: “If I have leaks in my business, I first have to plug in my leaks. So then as I go for more, I get to keep more of what I capture.” This underscores sustainable scaling through systems.The Principle of Impact ties education, systems, and influence to meaningful outcomes. Israel’s four steps of breakthrough—obscurity, resistance, light, and acceleration—guide entrepreneurs to authority and income. He emphasizes, “The way to impact always… comes before is influence.”Israel’s story and principles inspire action, making this a must-listen for entrepreneurs. His advice to rethink approaches and build systems resonates deeply.Key Takeaways:Release the Past: “I’m not going to let my past define my present or my future.”Fix Leaks: “Entrepreneurship is not about just making money, but it’s about keeping the money.”Build Influence: Embrace the four steps of breakthrough for lasting impact.Seek Specialized Education: Learn from mentors who’ve succeeded in your goals.Stay Humble: “Your humility has to 20x your abilities” for ongoing growth.This episode offers practical wisdom for entrepreneurs ready to move beyond the status quo and create lasting wealth.

Mitch McGinley is the founder and CEO of a Boutique Fitness Broker firm, an expert in guiding entrepreneurs in health, wellness, and fitness through the complex process of selling their businesses. We spoke about his journey from hotel management to owning and selling a yoga studio, the realities of business valuation, and the strategies that lead to successful exits. Our conversation unpacked why only 20% of listed businesses sell and how Mitch’s approach achieves an impressive 80-90% success rate.The most critical insight from Mitch is the importance of preparation and mindset in achieving a lucrative exit. He emphasizes that valuations hinge on profit, not sentiment or brand aesthetics: “Valuations are based on profit... not your brand, not how cool your logo is, not how long you’ve been in business.” This reality check is vital for passionate entrepreneurs who may overlook financial discipline. Mitch’s story of helping a Club Pilates owner secure $600,000 more in just four days underscores the value of expert guidance: “I saw him get an offer and saw the deal through and he walked away with $600,000 more.”We explored practical steps for business owners to prepare for a sale, from cleaning up financial records to planting seeds with potential buyers years in advance. Mitch’s advice to “begin with the end in mind,” inspired by Stephen Covey, encourages owners to view their business as a chapter, not a lifelong commitment: “No one expects you to keep the same job for the rest of your life. Why would you keep one business for the rest of your life?” His perspective is a wake-up call for those who see their ventures as inseparable from their identity, especially in altruistic fields like yoga or wellness.Mitch also demystifies the brokerage process, describing it as a “white glove service” where brokers act as advisors, therapists, and advocates, aligning sellers and buyers for mutual success. His focus on community preservation—ensuring businesses remain sacred “third spaces” for employees and clients—adds a heartfelt dimension to the transactional world.Key Takeaways:Profit Drives Value: Clean financials and a focus on discretionary earnings are non-negotiable for attracting serious buyers.Plan Early: Start preparing two years out by organizing records, networking with investors, and subtly identifying internal buyers: “Planting seeds... casual comments to staff, clients, friends... can grow within their brain.”Leverage Expertise: A skilled broker can significantly increase your payout, as seen in Mitch’s $600,000 win, debunking the myth that broker fees diminish returns.Mindset Shift: Treat your business as a valuable asset, not your life’s purpose, to embrace new chapters with confidence.This episode is a must-listen for entrepreneurs who want to turn their passion-driven businesses into profitable exits while preserving their legacy. Mitch’s blend of hard-earned wisdom and practical tactics offers a roadmap to not just sell, but to sell smart.

Scott Sheridan is a seasoned entrepreneur and trader who co-founded thinkorswim, a transformative platform later acquired by TD Ameritrade. We spoke about his journey from trading on the Chicago Board Options Exchange to building and selling multiple businesses, the mindset required to navigate entrepreneurial risks, and the importance of giving back to the community. Sheridan’s story is a masterclass in resilience, adaptability, and strategic thinking, offering practical wisdom for aspiring entrepreneurs.The conversation highlights Sheridan’s philosophy of “eating what you kill,” a trader’s mentality that shaped his entrepreneurial approach. He emphasizes the need for minimal personal expenses to preserve capital for business growth, recalling, “When my partner and I started thinkorswim, we took a minimal, minimal salary and we never changed it.” This discipline underscores a key takeaway: prioritizing the business over personal gain is critical in the early stages.Sheridan’s insights on pivoting are particularly compelling. He warns against rigidity, noting, “Most people become too rigid and they’re not willing to modify. They say, this is my idea. I’m not pivoting from that idea. And typically, that leads to problems, which leads to failure.” Instead, he advocates for launching a minimum viable product (MVP) and iterating based on feedback, a strategy that avoids “paralysis by analysis.” As he puts it, “Get the idea out there as quickly as you could possibly get the idea out… it puts pressure on the dev team to build as quickly and iterate as fast as they can.”Another standout topic is the power of partnerships and trust. Sheridan’s 36-year collaboration with his business partner exemplifies the value of complementary strengths and mutual confidence. “I would hand him my checkbook, I would hand him my credit cards. Wouldn’t even think about it,” he says, highlighting the rarity and necessity of such trust. This reinforces a key lesson: success is a team effort, not a solo endeavor.Sheridan’s reflections on giving back add depth to his story. His support for Lurie’s Children’s Hospital and Cooper Union, where his father studied, reveals a commitment to social responsibility. The emotional impact of receiving letters from students who benefited from his fund is palpable: “I had tears in my eyes because… they couldn’t have come to this school without your help.” This underscores a profound takeaway: true success extends beyond financial gain to creating lasting impact.From Sheridan’s candid admission that he didn’t have a paycheck until age 35 to his view of business as a game akin to trading, the episode is packed with gritty, actionable advice. His father’s influence, a lifelong entrepreneur who worked until 36 hours before his passing, adds a personal layer, reminding us that passion drives persistence. As Sheridan notes, “It’s not work if you’re excited to go do it.”Key Takeaways:Embrace adaptability: Be open to modifying your idea based on market feedback to avoid failure.Launch fast, iterate faster: Release an MVP to validate concepts and refine based on real-world input.Build trusted teams: Surround yourself with reliable, complementary partners to amplify success.Plan for a longer runway: Anticipate that time and costs will likely double or triple initial estimates.Give back meaningfully: Success carries a responsibility to support your community, whether through time or resources.Sheridan’s journey is a testament to the grind and glory of entrepreneurship, proving that with risk, resilience, and a willingness to pivot, ideas can indeed come to fruition.

Douglas Noll is a lawyer-turned-peacemaker who transformed his life from battling in courtrooms to teaching murderers in maximum-security prisons how to halt violence. We spoke about his remarkable journey from overcoming physical disabilities and a high-flying legal career to pioneering a revolutionary approach to de-escalating conflict. Noll shared how he developed a simple yet powerful skill—emotional validation, or "affect labeling"—that can stop fights, arguments, or tense conversations in 90 to 120 seconds, fostering instant calm and trust.The most striking takeaway is Noll’s discovery that traditional conflict resolution methods, like active listening or non-violent communication, often fail when emotions run high. Instead, his technique, backed by neuroscience, taps into the brain’s wiring to calm negative emotions and restore rational thinking. He explained, “When you validate another person’s emotions… the areas of the brain associated with negative emotions… are inhibited… you restore their ability to think.” This approach, honed in gritty prison basements and high-stakes mediations, is universally applicable—whether you’re dealing with an angry colleague, a estranged family member, or a heated boardroom dispute.Noll’s stories are gripping, like the moment he mediated between a divorced couple screaming “vile insults” at each other. By guiding them to label each other’s emotions, he witnessed a breakthrough: “John put his face in his hands and started sobbing… He says, ‘That’s the first time you listened to me in 25 years.’” Equally moving was the story of Sarah, a prisoner who used affect labeling to reconnect with her son after 18 years of silence, illustrating the skill’s power to mend even the most fractured relationships.What’s compelling is Noll’s belief that anyone can master this skill in just eight weeks, empowering them to face conflict without anxiety. He envisions a world transformed by this practice: “If enough people start throwing that pebble into that pond, we will have a tsunami of peace and our culture will be changed forever.” His work challenges us to rethink how we listen—not to words, but to emotions—unlocking a path to peace in any high-pressure situation.Key Takeaways:Emotional validation can de-escalate any argument in under two minutes by calming the brain’s emotional centers, as Noll learned from a 2005 mediation and later confirmed by UCLA brain scans.Traditional methods like taking deep breaths or walking away often fail to address intense emotions, but affect labeling works “every single time, without fail.”Noll’s Prison of Peace Project taught murderers to become peacemakers, proving the skill’s transformative power in even the most extreme settings.This skill is for anyone—couples, teams, or individuals—who wants to navigate tense moments with confidence and compassion, from family disputes to workplace conflicts.By listening to emotions, not just words, you can build instant trust and loyalty, as Noll did with inmates and mediators alike.

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.