21st Century Entrepreneurship

Terry Ross is a powerhouse in the medical aesthetics business—and we spoke about what it really takes to turn a beauty-based practice into a multi-million-dollar machine. With 20 years of experience helping medical spas, wellness clinics, and aesthetic practices scale into high-performing, sellable businesses, Terry brings a refreshingly analytical, strategic lens to an industry often seen through an emotional or purely visual lens.We talked about the business of beauty—why most highly trained medical professionals struggle with running a practice, and what they can do to finally bridge the gap between their clinical skills and business performance. From understanding gross profit margins to training your front desk team to convert calls into paid visits, Terry reveals why ignoring the backend systems is the most expensive mistake a practitioner can make.“Whether you run a med spa or you run a tech company, the fundamentals are the same. Knowing your numbers, training your people, building something scalable.”She breaks down three of the seven strategic pillars in her consulting framework:Revenue Optimization: “If we're not hitting those target benchmarks… we're losing money.”Staff Training & Development: “You're spending money in marketing to acquire a patient… If you're not converting those patients at a 70% ratio, you're losing them.”Patient Acquisition & Retention: “There’s riches in the niches. You don’t need to be everything to everybody.”What stood out most is her laser-focus on accountability and systems—not just for doctors, but for every single team member. In a cash-based business, she says, you’re not selling products—you’re selling time, outcomes, and trust.Key takeaways:Most aesthetic practices hemorrhage money because they don’t understand the true cost structure of their services.Sales training isn't optional—it's the highest ROI investment in a service-based business.Marketing isn't just spend—it’s strategy. Know your niche, tailor your message, and focus on lifetime value, not just clicks.Data is your best friend: “Understanding KPIs and analytics… that is the navigation point that tells the story.”If you're in wellness, aesthetics, or any cash-based business, this episode is your blueprint to sustainable, scalable success.

Daryl Black is a crisis-tested leadership coach, emergency response veteran, and creator of the Order to Chaos framework—and we spoke about what building startups, leading high-growth teams, and surviving natural disasters have in common.With three decades of experience in both emergency management and corporate project leadership, Daryl brings frameworks forged in fire—literally. From tornadoes and wildfires to multimillion-dollar business projects, he’s learned that leading in uncertainty requires more than grit—it demands clarity, structure, and emotional mastery.“What got you here won’t get you there… It’s no longer about doing the stuff anymore. It’s about the people part of the business.”We unpacked his Order to Chaos model, including how to go from frantic startup hustle to focused leadership, and why so many founders stall when they can’t make the leap from expert to people leader.“I’ve coached thousands of leaders and so many of them say: ‘I love my job. It’s the people part that’s hard.’ And I get it.”You’ll also hear how he builds high-performing autonomous teams—sometimes from scratch in the middle of an evacuation zone—and what leaders of leaders must do to scale influence across organizational layers.Topics we explored:How crisis leadership principles apply to business growthWhat entrepreneurs get wrong about scalingWhy frameworks beat improvisation under pressureThe 1-3-1 method for decision-making and ownershipHow to coach your top performers and manage your weakest linksMoving from command-and-control to a support model“We’re not building the bus as we’re driving it anymore. We’ve got the brights on now.”Key Takeaways:Self-mastery comes first: “Leadership always started with me… am I managing my sleep well? My nervous system?”Productivity is non-negotiable: Learn about “time fencing” and how to stay focused in the eye of the storm.Influence without micromanaging: “Come to me with one problem, three options, and one recommendation.”From chaos to clarity: Frameworks like OTC and 1-3-1 aren’t just tools—they’re lifelines.Whether you’re leading a startup, scaling a team, or managing through the unknown, Daryl’s stories and systems offer an essential blueprint for staying calm, focused, and effective—even when the metaphorical tornado hits.

Brian Truman is an experienced entrepreneur based in Nashville, Tennessee, and we spoke about the hidden power of collaborative entrepreneurship, the mindset shift from corporate comfort to building your own business, and how to create a life — and legacy — by design.From leaving a secure 22-year corporate career to launching multiple successful companies in real estate, business brokerage, and property management, Brian shares the moments that shaped his journey — and the mindset that sustained it. But perhaps most striking is his belief that entrepreneurship doesn’t have to be lonely.“Too many people go into it thinking they have to do it all by themselves when they don’t — and it’s best that they don’t.”We discussed the role of mentorship, spousal alignment, and what it really takes to transition from a paycheck to passion. Brian’s story is filled with practical insight — like how a single cold call to a Florida-based broker turned into a life-changing 90-minute call and a lasting friendship.“I asked him if I could have 10 or 15 minutes. We talked for an hour and a half.”He breaks down how his companies help clients build generational wealth by using business exits to fund real estate strategies, and why “a life by design” is more than a motivational phrase — it’s a step-by-step plan he creates with his clients over six to eight years.And when it comes to leadership and legacy, Brian makes it clear:“We’re here to help you create your standard of living so you can create your standard of giving.”Key themes we discussed:Why mentorship isn’t weakness — it’s your shortcutNavigating the leap from corporate life to entrepreneurshipBalancing ambition with a partner’s sense of securityBuilding long-term financial freedom through strategic business exitsThe underestimated ROI of community service in company cultureTakeaways:Ask boldly. The right conversation can change your career.Plan backward. Map your vision year by year — income, ownership, freedom.Don’t build alone. Collaboration is not a risk — it’s your edge.Legacy isn’t abstract. It’s built through systems, service, and structure.If you’ve ever wondered whether you have to figure out entrepreneurship alone — or if your success can fuel more than just income — this episode will shift your perspective.

Stela Roznovan is a former concert pianist turned multimillion-dollar agency director — and we spoke about how mastering sales isn’t about hustling harder or memorizing 15-page scripts, but about tapping into clarity, connection, and confidence.Stela leads a $3M remote sales organization with over 100 reps and has mentored hundreds of young, driven individuals — former athletes, recent grads, and ambitious go-getters — who come to her burnt out and discouraged. Why? Because they’re “doing everything right by the book,” but nothing’s clicking. Her response? Throw out the script.Instead, Stela teaches a refreshingly practical 3-step framework built around authenticity, exclusivity, and urgency. It’s not theory — it’s what she uses live, every day, with her team watching in real-time.“Authenticity is why the client buys from you. Urgency is why they should buy today. And exclusivity is why they should buy this product.”Her approach is shaped by real-world grit. She recalls spending 10.5 hours driving to her first appointment in month two of her sales career — only to still close five deals. That kind of resilience — not polished scripts — is what she believes sets true closers apart.We also talked about:Why being liked isn’t optional in a sales conversation — “If you can't mirror someone’s behavior, they simply don’t like you.”How she turned a failed 15-page script into a simple, high-converting frameworkWhy “sales is the highest paid profession in the world” — if you master itHer team’s secret weapon: live observation rooms where reps watch real closings happen — “not theoretical stuff… real stuff they can implement on their next call”Building a high-performing culture 100% virtually — and how it’s scaling fast across all 50 statesShe also explains how applying discipline from her life as a pianist shaped her sales success:“You become a top performer in the practice room, not on stage.”Key takeaways:Don’t sell. Qualify. Your role is to guide, not push — “You’re helping somebody qualify for something versus selling them something.”Stop over-explaining. “As long as the client feels like they’re getting the best end of the deal, they will want to make a buying decision.”Burnout isn’t the problem — misalignment is. Most people quit “at the 350th call, when the 351st would have been their $4,000 deal.”Purpose matters: Her agency links performance to impact — saving dogs, helping kids, and giving reps something bigger than a paycheck to work toward.Whether you're in sales, building a team, or just tired of the hustle-without-results grind, this episode delivers both mindset shifts and hard-earned tactics to help you close — and lead — with clarity.

Christine Healey is CEO of Healey Pre IPO and an expert in private tech investments with nearly a decade of experience brokering deals in unicorns like SpaceX and OpenAI, and we spoke about the fragmented world of pre-IPO investing, why high-net-worth individuals are drawn to it, and how her concierge service simplifies access to these elusive opportunities. We discussed the challenges of navigating shady platforms, unreliable deals, and the lack of a centralized exchange for private shares, contrasting it with the ease of public markets where "you can go onto an exchange and type in a ticker and it's very simple and centralized." Christine shared her journey from investment banking to leading a pre-IPO fund and launching her own business, emphasizing the shift in company lifecycles: "Today these large private tech companies are choosing to delay their IPOs and stay private, sometimes up to billions, tens of billions, hundreds of billions of dollars in valuation," which shuts out public investors from massive growth. From my perspective, the most important insight is the democratization of access—pre-IPO shouldn't be reserved for venture capitalists or the ultra-connected, as it allows everyday accredited investors to own stakes in "futuristic pioneering companies that are changing our world." Listeners can learn strategies for managing risks in this high-reward market, like adopting a "flight to quality" by focusing on high-conviction companies, and the value of a personal broker to avoid "analysis paralysis" from false starts and impersonal platforms. A clever highlight: Christine calls out the "proliferation of mediocrity" in brokers and platforms that promise access but often lead to frustration, noting, "They want to talk to a human. It's almost like an old school, human approach to a market that is very new school." Key takeaways include: Accreditation requirements (e.g., $200K income or $1M net worth) gatekeep entry but open doors to potentially larger upsides than public IPOs; building a global network—from California employees to Middle Eastern family offices—yields better deals; and while successes like SpaceX inspire, failures like FTX remind us it's "a high risk market and it's a certain niche of investor that will really be drawn to the type of opportunities at play here." Overall, this conversation demystifies pre-IPO as a viable diversification tool for savvy investors passionate about tech innovation.

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.