21st Century Entrepreneurship

Samantha Upchurch is a passionate entrepreneur and health advocate who shared her transformative journey from poverty to building multimillion-dollar businesses. We spoke about her life-altering experiences, the five-step process she developed to achieve success, and how resilience and health play pivotal roles in sustaining it.Samantha's story began in a small Greek village, where simplicity and close community ties shaped her early years. But life took an unexpected turn when her family moved to England, leaving her with nothing but the determination to rewrite her destiny. "At the age of 8 or 9, I asked myself, ‘Am I okay with this life?’ And the answer was a resounding no," she recalled.Through her journey, Samantha discovered the importance of resilience. She emphasized, “Resilience isn’t just bouncing back; it’s actually bouncing forward.” Her approach involves reframing failures into stepping stones and leveraging past experiences to navigate current obstacles.She also underscored the role of passion and work ethic in achieving goals: “Passion is the engine, and strategy is the vehicle,” she stated. Samantha’s actionable advice includes writing down strengths, weaknesses, and opportunities to gain clarity and focus on what drives you.Finally, Samantha revealed a key insight: success is as much about health as it is about mindset. “How can you pour into a successful business from an empty cup? You can’t,” she said, stressing the need to address both psychological and biochemical imbalances.Key TakeawaysReprogram Your Mind: Identify limiting beliefs and transform them into empowering thoughts.Discover Your Passion: “Without passion, challenges will defeat you.” Find what excites you and turn it into opportunity.Adopt Relentless Work Ethic: Consistency beats intensity every time. Schedule your efforts and focus on high-value tasks.Cultivate Resilience: Learn from failures, and use them as steps to move forward.Prioritize Health: Balance psychological well-being with nutritional alignment to sustain long-term success.Samantha’s journey is a testament to the power of mindset, hard work, and a holistic approach to life. This episode is packed with actionable advice and inspiration for anyone ready to rewrite their own story.

Jay Tobey is an entrepreneur and founder of Northstar Recovery and Wellness who combines passion, philanthropy, and strategy to tackle one of the most pressing challenges of our time—creating a seamless continuum of care in the fragmented behavioral health industry. We spoke about his entrepreneurial journey, the cracks in the mental health and substance abuse system, and his innovative investment model blending real estate with operational support to drive long-term recovery outcomes.One of the most striking statistics Jay shared was that "one in six people have a substance abuse disorder and nearly 25% of adults have struggled with a mental illness at some point." Yet, only a fraction of those in need receive treatment, highlighting the urgency of rethinking current systems.Jay discusses the critical gaps he identified, such as the lack of consistent care and the challenge of patients falling through the cracks when transitioning between facilities. His solution? Building a "continuum of care for inpatient, supportive housing, sober living, and long-term outpatient" to ensure sustainable recovery over years, not just weeks.In addition to tackling systemic issues, Jay shares how his "personal board of directors"—trusted mentors who are ten steps ahead—has guided his strategic decisions, from structuring share ownership to maximizing tax benefits during exits.Key Takeaways:Long-term Recovery vs. Quick Fixes: Jay emphasizes the need to shift from 90-day programs dictated by insurance to multi-year solutions: "Each year someone is clean and in recovery, statistically their chances of staying clean skyrocket."Fragmentation in Behavioral Health: The top companies hold only 1% of the market share, leading to a highly fragmented system that requires tailored approaches based on geography and population.Real Estate as a Backbone: Jay’s investment model blends private equity with real estate to scale facilities quickly while ensuring investor security.Continuous Improvement Through Data: He challenges operators to prove outcomes: "Are you tracking your data? Are you proving that people are having long-term success with you?"This episode offers a mix of entrepreneurial insights, bold investment strategies, and a heartfelt commitment to helping those in need. Whether you’re in healthcare, real estate, or looking to make an impact through business, Jay’s approach will inspire and challenge you.

Oleg Romanov is a seasoned IT entrepreneur and AI expert based in London, with a mission to help businesses harness the transformative power of artificial intelligence. We spoke about practical ways AI can solve real business challenges, such as streamlining operations, boosting efficiency, and unlocking new growth opportunities.Oleg shared an inspiring case study from the real estate industry, where AI-powered assistants revolutionized lead management and sales processes. "We connected this AI assistant to his website and social media, and now it handles thousands of consultations instantly," he explained. This solution freed up managers to focus on closing deals, ultimately enabling the company to scale its advertising and grow exponentially.Key topics included:Identifying the Right Problem: Oleg emphasizes that AI implementation begins with pinpointing your business's main pain point. "It's the thing that stops you from growing 10 times now," he shared.Strategic AI Integration: From chatbots to advanced automation, Oleg outlined steps to leverage AI effectively while avoiding common pitfalls.Mindset and Growth: Drawing from his Muay Thai experience, Oleg highlighted resilience and determination as critical traits for entrepreneurs: "There is always a chance to win, even if it’s just 5%—you can win. Never give up."Mentorship and Collaboration: Oleg also shared how partnering with like-minded individuals can amplify success, saying, "When 1 plus 1 equals 11, it really helps to move forward."Takeaways:AI is a tool, not a magic solution. It works best when targeted at specific business goals.Collaboration and the right support network are key to entrepreneurial success.Personal development and continuous learning are crucial investments for any entrepreneur.Whether you're an established business owner or an aspiring entrepreneur, this episode offers actionable insights on integrating AI, fostering resilience, and building strong partnerships to achieve your goals.

Lior Weinstein is a lifelong entrepreneur, founder of CTOx, and a pioneer in fractional leadership. Starting his first company at 14, Lior has since built and sold multiple tech companies. Now, as a fractional CTO and CRO, he helps businesses unlock their potential by bridging the gap between vision and execution. We spoke about the challenges CEOs face in navigating technology, the transformative power of AI, and how fractional roles redefine leadership.One of the most striking points Lior makes is the importance of communication in tech leadership:"If you meet another professional and you don’t understand them, you should actually think about that. If they knew what they were talking about, they’d be able to explain what they do and how you can work together.”Here’s what you’ll learn in this episode:Choosing the Right Tech Partner: Lior shares why not understanding your CTO or tech team is a red flag, emphasizing the need for clear communication to ensure collaboration and results.Unlocking AI's Potential: With over 20 years in AI and five patents, Lior breaks down how tools like ChatGPT work and why it’s crucial to adopt AI in business. “If you’re not actively using AI, I consider it professional negligence.”Rethinking Software and Development: Learn about the shift from software-as-a-service to service-as-software and how AI makes building custom solutions accessible and affordable.Fractional Leadership’s Value: Discover how fractional roles, like CTOs and CROs, provide expertise at a fraction of the cost while delivering full-scale impact. As Lior puts it, “My clients need my leadership, not my labor.”Future-Proofing Your Team: Why resistant staff might not be part of your company's future and how to foster a mindset that embraces rapid innovation.Lior also reveals how AI tools are transforming workflows by collapsing timelines from weeks to minutes. “We’ve eliminated 80% of first-month decisions by using tools that provide instantaneous feedback loops.”This episode is packed with actionable insights for CEOs, tech leaders, and anyone looking to thrive in a tech-driven world. Don't miss Lior’s perspective on how combining leadership, vision, and AI can drive unparalleled growth.

Darius Ross is a seasoned entrepreneur with over 40 years of experience, and we spoke about navigating the global economy's seismic transitions. From the challenges posed by AI and escalating unemployment to opportunities in selling businesses strategically, this episode explores how to survive and thrive in uncertain times.Darius shared his journey of rising from the inner city of Chicago to becoming a leader in private equity, offering invaluable lessons for entrepreneurs at any stage. "Entrepreneurship is going to be very key because corporate jobs are going to be either diminished and or eliminated," he emphasizes, pointing to a future where adaptability is a necessity, not an option.Key takeaways from our conversation include:Navigating a transitional economy: Learn how global shifts in leadership and AI are reshaping opportunities.Positioning your business for sale: Darius breaks down the essentials of seller financing, tax planning, and creating a buyer-friendly offering to ensure a successful exit.Leadership in adversity: Insights from Darius’ book on how leaders can shoulder responsibilities and overcome mental breakdowns to keep their teams on track.Empowering future entrepreneurs: His 716 Foundation aims to inspire urban youth to enter real estate and entrepreneurship, creating pathways for long-term success.One standout insight: only 1 in 100 businesses successfully sells, leaving many entrepreneurs without retirement plans. Darius offers solutions, including packaging businesses for private equity deals to secure a "cash-rich position" and a stable future.If you’re an entrepreneur pondering what’s next or grappling with how to adapt to today’s economic realities, this episode is your roadmap.

Michael Stone is the leader behind one of the largest players in the North American painting industry, holding a remarkable 1% of a $60 billion market. We spoke about how CertaPro Painters has grown fivefold in its space, yet still sees massive growth potential. This conversation dives into the essence of what fuels that success—not painting, but leadership, people development, and community impact.From humble beginnings in sunny San Diego to leading a $300 million brand with a vision of reaching $2.5 billion, Michael’s journey showcases the power of entrepreneurial mindset, leadership development, and the value of creating extraordinary experiences. “Businesses don’t grow. People grow,” he emphasizes, revealing the core philosophy behind CertaPro Painters’ scalable franchise model.Here’s what we covered:Leadership and Growth: Why leadership, not technical expertise, is the cornerstone of growing a thriving business.Franchise Support System: How a “business for yourself, not by yourself” model empowers franchise owners with state-of-the-art tools, marketing, and coaching.Core Values in Action: Michael shares how delivering on promises, respecting individuals, and embracing possibilities fuel extraordinary experiences for customers and stakeholders alike.Community Impact: Learn how initiatives like "Paint it Pink" for breast cancer awareness unite franchisees and communities, making a tangible difference beyond profit.Earned Growth: Michael illustrates the power of customer referrals, calling it “earned growth” that builds trust and community loyalty, exemplified by touching customer stories and personal thank-you gestures.Takeaways:Focus on people, not products: “The key to growing a successful, professionally managed large-scale painting operation is really about leadership development.”Deliver extraordinary experiences by living core values.Community engagement, like "Paint it Pink," drives brand loyalty while making a positive impact.True growth is earned, not bought: “You can buy a lot of growth...but earning growth is when you know you’ve enriched the lives of the people that you work with.”Whether you're considering a franchise opportunity, looking for ways to scale your business, or seeking inspiration to lead with purpose, this episode offers actionable insights and a roadmap for creating impact through leadership.

Nick Foy is the CEO, founder, and chief evangelist of Silverdale, a consulting company revolutionizing ERP implementations. We spoke about why most ERP projects fail, the critical mistakes businesses make, and Silverdale's innovative approach to creating successful outcomes.Nick shared that 75% of ERP projects fail to meet their objectives, a statistic that often deters companies from starting. However, he passionately explained how his team combats this through their proprietary Silverdale Implementation Method (SIM), emphasizing discovery, design, and delivery. "The trick is to understand which business processes make you unique and focus on those," Nick stated, urging companies to avoid unnecessary customizations that derail projects.Key topics included:Silverdale’s Fixed Pricing Model: Unlike traditional hourly billing, Silverdale aligns its goals with clients to ensure timely delivery without hidden costs.Transforming ERP Processes: “Don’t mold your ERP around your process—adjust your process to fit the ERP,” Nick advised, highlighting a major pitfall of failed implementations.AI’s Role in Consulting: Meet Dale, Silverdale’s 51st “employee,” an AI assistant improving efficiency by analyzing past projects and assisting the team in real time.A few takeaways:Customization isn’t always the answer. Focus on what makes your business unique rather than tailoring standard features.Phased success is key. Silverdale’s methodology involves hands-on discovery, iterative design, and robust post-implementation support.AI augments, not replaces. Leveraging AI enhances service quality while keeping the human touch central.Whether you're considering your first ERP implementation or recovering from a failed one, Nick offers a roadmap to success that’s as practical as it is innovative.

Brad Sugars is the #1 business coach in the world, an entrepreneur with a $2.5 billion track record, and the founder of ActionCoach, the largest business coaching franchise operating in over 80 countries. We spoke about his six-step framework for building a thriving business, the common pitfalls entrepreneurs face, and the formulaic principles behind achieving both business and personal success.At the heart of Brad’s approach lies a simple yet powerful formula: Dreams × Goals × Learning × Plans × Action = Success. According to Brad, “If there are no dreams, there’s no necessity to do your best.” From setting clear visions to working backward into actionable plans, Brad unpacks how these components multiply to create exponential growth.We also discussed his proven six-stage business-building process:Mastery – "Get very good at four key areas."Marketing – “There’s a formula for that: leads, conversion, transactions, and margins.”Systemization – Nine steps to ensure the business runs efficiently.Team Building – Six keys to a winning team.Scaling – Five disciplines to expand.Freedom – "A business that works without you."Brad’s insights go beyond just strategies. He shares personal anecdotes, like how his early grind masked broken systems in his business. “I wore it as a badge of honor,” he admits, “but me working that hard just covered up the fact that my sales system didn’t work.” His journey from hustler to a systems-driven leader highlights why entrepreneurs must grow themselves to grow their businesses: “Your business cannot outgrow you.”Other key takeaways include:The Marketing Mindset: "Your job is to get people to say, ‘I’m interested.’”Building a Mission: “Great people don’t want to work for a company that doesn’t have massive goals and a big vision.”The Power of Giving Back: With initiatives like pro bono coaching and programs for young entrepreneurs, Brad emphasizes, “You can’t just be taking. You’ve got to be giving back.”We also touched on the loneliness of entrepreneurship and how coaching bridges that gap by providing guidance, structure, and accountability. Whether you're an aspiring entrepreneur or a seasoned business owner, this episode offers actionable advice and a formula you can immediately implement to drive your success.

Charlotte Watts is a resilient entrepreneur who turned her burnout and frustration into a thriving business. We spoke about the challenges of starting and growing a company, the personal sacrifices involved, and the mindset shifts that helped her navigate adversity and build success.Charlotte’s story is a testament to perseverance. From balancing a grueling work schedule with raising four children to battling cash flow crises and non-paying clients, her journey is filled with lessons for aspiring entrepreneurs. As she puts it, “The reality of what your first business plan is to the reality of that hits hard. And this is the point why businesses give up within the first year.”A few of the topics we explored include:The Breaking Point: How Charlotte realized she needed to leave her corporate job. “I thought, I can’t live my life like this. I’ve got these beautiful children. I’m making this company loads of money, but I don’t have a life.”Taking the Leap: Starting a business with no prior experience and learning on the go. “I had no clue about P&L sheets, registering with the tax man, or even setting up a company name.”Overcoming Early Challenges: The struggles of hiring her first employee and dealing with months of no bookings. “I took on my first nurse, and she didn’t get booked for three months. By this time, my money was really running out.”Battling Injustice: Navigating court battles and dealing with unethical business practices. “I had to go through a winding-up petition to finally get paid, and it took nine months.”The Power of Perseverance: Why resilience matters in entrepreneurship. “You have to keep going, even when it feels like the world is out to get you.”Key Takeaways:Be Prepared for the Unexpected: Success in business often requires handling unforeseen challenges, from cash flow issues to legal battles.Learn as You Go: You don’t need to know everything when you start, but you do need the willingness to learn and adapt.Find Your Support Network: Charlotte emphasizes the importance of having a "clan" to lean on. “You need people you can sound off to and share the load with.”Celebrate Small Wins: As Charlotte puts it, “The first booking was like, hallelujah.” These milestones keep you motivated.Charlotte’s journey proves that perseverance, self-belief, and a sense of humor can turn even the toughest challenges into stepping stones to success. If you’ve ever wondered whether you have what it takes to run a business, Charlotte’s story will inspire and empower you.

Matt Tait is on a mission to make entrepreneurship more manageable. We spoke about how adaptability, intentional leadership, and leveraging technology are key to running and growing a successful business in today’s ever-changing landscape.Drawing from his journey—from being a "recovering attorney" to leading Decimal, a tech-driven accounting company—Matt shared lessons learned from his winding entrepreneurial path. His upbringing in a family of entrepreneurs shaped his vision, but it was his failures and pivots, like running a restaurant tech company that “was a good idea but a terrible business,” that taught him resilience.We discussed the importance of adaptability, which Matt describes as "the number one characteristic of successful entrepreneurs." From recognizing personal weaknesses to building a complementary team, Matt emphasized that "you can't grow if you can't see what you need to improve." He also stressed the power of investing in a coach, saying, "A paid coach will give you that hard advice and reflection you need to understand where to grow."Key Takeaways:Adaptability is Essential: Entrepreneurs must embrace change, whether in scaling operations, managing a growing team, or integrating new technologies. "You have to admit you can't do it all," Matt explains.Self-Care Fuels Success: Matt’s daily routine of meditation and exercise supports his mental and physical health, enabling him to lead effectively. "Figure out what works for you," he advises, "and allow it to adapt as life changes."Build a Support Network: Loneliness in leadership is real. Matt encourages finding a peer group and investing in a coach to navigate challenges and maintain perspective.Lead with Intention: In a remote-first culture, leadership requires extra effort to build connections and foster growth. "Every employee is an island; it's our job to build bridges," Matt says.Through humor, honesty, and hard-earned wisdom, Matt reveals what it takes to navigate the complexities of entrepreneurship while staying true to your mission. Whether you're scaling your business or reflecting on how to improve as a leader, this episode is packed with actionable insights to help you thrive.Explore Matt's journey and connect with his content on LinkedIn or through After the First Million podcast.