The Entrepreneurial Journey

This week, Dave sits down with David Heaps, Founder of Leadering, for a very different kind of conversation about leadership. After leaving the corporate world, David spent years studying with indigenous teachers in the Amazon, including more than 10,000 hours in silent isolation. That experience eventually became the foundation for his Inner Architecture Work. David explains why CEOs can know exactly what they need to do and still avoid doing it, how old beliefs quietly influence leadership, and why the real “noise” entrepreneurs struggle with often comes from their own minds. Dave and David get into accountability, difficult conversations, childhood patterns, self-doubt, and how leaders can stop operating on reflex and start making different choices. David is also offering viewers a free 90-minute Inner Architecture Audit. Learn more at Leadering.com/TEJ.

Lisa Pagotto has every reason to have quit. She sold her house to start Crooked Compass. Made it onto Shark Tank. Watched her business take off. Then one signature that never came nearly destroyed everything she’d built. Most people would have walked away. Lisa didn’t. In this conversation, Dave sits down with the Founder & CEO of Crooked Compass to hear one of the wildest entrepreneurial stories we’ve had on the show. From an investor deal falling apart at the last possible second, to a stranger stepping in with a life-changing act of generosity, to rebuilding an international travel company during a global pandemic, Lisa’s journey is full of moments that forced her to choose between giving up and figuring it out. The conversation also dives into the mindset that’s helped her keep moving through every setback. Lisa shares the FIRE Framework she now teaches to leaders around the world, why integrity matters even when it costs you, how rest can actually make you a better entrepreneur, and why waiting for certainty is usually the fastest way to stay stuck. Of course, you’ll also hear about the incredible experiences Crooked Compass creates, taking travelers far beyond the usual tourist stops and into some of the most fascinating places on Earth. Whether you’re building a business, navigating a setback, or wondering if it’s time to make that call you’ve been putting off, this episode is a reminder that the next opportunity rarely looks the way you expect it to.

If you're a business owner who doesn’t think about selling until you're ready to leave, this week's guest says that’s already too late. This week, Dave sits down with Saul Cohen, Partner & CEO of The Expert Eye, to talk about building a business that’s worth more long before you ever put it on the market. Saul explains why entrepreneurs should get regular business valuations, how his SCORE Framework helps increase company value, and why two businesses with similar profits can sell for completely different prices. He also shares practical advice on acquisitions, tax planning, balancing entrepreneurship with family life, and why founders create the positive change that moves the world forward. If you want to build a stronger business, create more wealth, or prepare for an eventual exit, this conversation is full of practical insights you can start using today.

Most entrepreneurs work incredibly hard to build wealth, but very few are taught how to protect it. In this episode, Dave sits down with Mark Miller, Managing Director of the Hilton Family Office and President & CEO of Hilton Tax & Wealth Advisors, to talk about how America’s wealthiest families think differently about investing, taxes, and long-term financial security. Mark explains why the wealthy prioritize safety over chasing returns, how entrepreneurs can legally reduce one of their biggest lifetime expenses through smart tax planning, and why a coordinated financial strategy beats picking the next hot investment. Dave and Mark also discuss AI, the importance of lifelong learning, and the story of Conrad Hilton’s integrity during the Great Depression. Mark is also offering listeners a free copy of Hilton Wealth at https://hiltonwealth.com.

Most entrepreneurs spend a lot of time thinking about sales. Kira Perdue thinks they should spend more time thinking about their story. This week, Dave sits down with the Co-Owner of SmArt Image to talk about branding, PR, and why the way you communicate can make or break your business. After helping companies like Verizon Wireless, Target, and Sun Microsystems build their brands, Kira now works with startups and growing businesses to sharpen their messaging, build trust, and stand out in crowded markets. Dave and Kira also discuss reputation management, crisis communications, working with your spouse, and why defining roles is critical when building a business together. If you’re looking for practical advice on building a stronger brand and a stronger business, you’ll get plenty of it in this conversation.

How do you build lasting wealth? According to Ash Kumar, it starts by seeing opportunities other people overlook. In this episode, Dave sits down with Ash Kumar, Founder & CEO of Ashford Communities, to discuss his journey from growing up in India and Canada to building a successful real estate investment company in Houston. Ash shares how creative thinking, persistence, and a willingness to keep learning helped him grow from buying small apartment buildings to leading a thriving real estate business. They also dive into creating value in every investment, raising financially smart kids, building meaningful relationships, giving back to the community, and why gratitude, continuous learning, and never giving up have been the foundation of his success. This episode is filled with practical lessons for entrepreneurs, investors, and anyone looking to build a better business and a better life.

How do you build an $11M+ business with zero debt? In this episode, Dave sits down with Jeremy Jenson, Founder & CEO of Encore Search Partners, to talk about what it really takes to scale a company. Jeremy shares how growing up in poverty shaped his mindset, why getting fired early in his career became a turning point, and how a struggling email marketing business eventually led him to build one of the country’s top executive search firms. They dive into hiring leaders who are better than you, implementing EOS, investing in executive coaching, and building a company that continues to grow without outside debt. Jeremy also opens up about rebuilding his life after divorce, overcoming destructive habits, and why the biggest breakthroughs happen when you stop blaming circumstances and start working on yourself.

What does it take to build a successful business while training for 100-mile ultramarathons? In this episode, Dave sits down with Jake Gerstenberger, Founder & Owner of Huckleberry Landscape & Property Services, to talk about resilience, leadership, and the mindset required to do hard things. After years as a wildland firefighter with the U.S. Forest Service, Jake launched his landscaping company in Missoula, Montana, and has grown it year after year through accountability, customer service, and a commitment to doing things the right way. Jake also shares incredible stories from the ultramarathon world, including battling hypothermia during a 100-mile race, running through injury, and learning how to push beyond perceived limits. It’s a conversation about business, endurance, culture, and why trusting your gut can change everything.

Most entrepreneurs think they need more marketing. Mickie Kennedy thinks they need more visibility. In this episode, Dave sits down with Mickie Kennedy, Founder & President of eReleases, to explore how a poet and former waiter built a 26-year business helping small companies earn media coverage and credibility. After discovering that journalists respond to stories, not data, Mickie created eReleases to give entrepreneurs affordable access to the media. Mickie shares how he knew it was time to leave his day job, why he waited until revenue doubled his salary before taking the leap, the lessons he learned from hiring friends, and the leadership shift that tripled his company after he stopped micromanaging his team. They also dive into what makes a press release newsworthy, why most press releases fail, and how entrepreneurs can use earned media to grow their business and build trust.

What happens when you refuse to give up? In this episode, Dave sits down with Natalia Zacharin, Founder and CEO of Zacharin Consulting. After a divorce left her rebuilding life as a single mother, Natalia found herself earning $7.10 an hour and struggling to make ends meet. Today, she leads an Inc. 5000 company generating more than $2.5 million annually and helping businesses improve profitability, cash flow, and financial decision-making. Natalia shares how she landed her first client, taught herself bookkeeping from scratch, and built a thriving business through persistence, consistency, and relentless learning. She also breaks down the biggest financial mistakes entrepreneurs make, why understanding your numbers matters, and how business owners can avoid the traps of shiny object syndrome, poor cash flow management, and reactive decision-making.

What if the thing holding your business back is your ability to communicate its value? This week, Dave sits down with Esther Stewart, Founder of CottnOwl and a Business Growth Strategist who helps premium service providers attract more clients through relationship-driven marketing and scalable sales systems. After spending eight years inside Fortune 500 financial institutions training seven and eight-figure executives on client retention, sales, and growth strategy, Esther learned a simple truth: premium clients don’t buy hype, they buy certainty. Dave and Esther discuss what most founders get wrong about sales systems, why strong relationships remain the ultimate competitive advantage, how to build trust online, and the small touchpoints that turn clients into long-term advocates. If you’re looking to grow your business without losing the personal connection that makes it special, this episode is for you.

Most small businesses struggle because they sound exactly like everyone else. In this episode, Dave sits down with consumer behavior expert, author, keynote speaker, former corporate buyer, World Series of Poker competitor, and accidental bootlegger Shawna Suckow for a conversation about what actually makes businesses memorable. Shawna explains why small businesses are finally positioned to outperform big brands, why sounding “professional” often hurts authenticity, and why storytelling matters more than polish. She also breaks down “micro stories,” her “sandbox theory,” and how AI is changing marketing through GEO, generative engine optimization. This episode is packed with practical insights for entrepreneurs who want to stand out, build trust, and avoid blending into the “blandscape.”

What do you do when the business you built starts breaking you? In this episode, Dave sits down with Jeff Hill, Founder & CEO of RePurpose Center and franchise owner of 1-800-GOT-JUNK?, to talk about resilience, reinvention, and building a business with real impact. After scaling his company through the early 2000s, Jeff was hit by the 2008 recession, major financial pressure, and a cancer diagnosis all at once. Instead of walking away, he rebuilt and eventually launched RePurpose Center, a company focused on keeping usable goods out of landfills and connecting them with people and organizations that need them. Jeff and Dave talk about entrepreneurship, partnerships, leadership during difficult seasons, and why success means more than just growth. This episode is a powerful reminder that sometimes the hardest moments shape the most meaningful businesses.

Luke Wade turned a simple Facebook post into one of Kansas City’s biggest community-building brands. This week, Dave talks with Luke Wade, Army veteran, Founder & CEO of The Facility Ally, Founder of KC Crew, and creator of thriving sports and social communities that have connected more than 150,000 people across Kansas City. What started as a downtown softball league became a multi-business ecosystem spanning sports leagues, facility management, media, software, sponsorships, and community experiences. Luke breaks down the systems that helped him survive 15 years in business while most companies fail, and shares the exact frameworks he uses to scale businesses without losing himself in the process. From purpose-driven entrepreneurship, veteran community building, and leadership, Luke has created meaningful experiences that matter more than chasing status or money.

This week, Dave sits down with co-founders Ashley Esqueda and Ross Miller of Rowdy Skeleton, a media agency that helps brands connect with people. Between them, they’ve spent 40+ years in media, working with companies like Nintendo, The Verge, Twitch, and Microsoft. They’ve seen how things have changed, specifically how being on camera isn’t optional anymore, and they get into why so many founders struggle to show up as themselves, how everything has shifted to video, and why being able to tell your company’s story might be one of the most valuable skills you can build. They also share how they coach leaders using their four pillars of connection: authority, transparency, presence, and trust, talking through everything from getting over the fear of being on camera to dealing with criticism. Rowdy Skeleton is ready to change the way you think about showing up for your business.

What if the life you built is the very thing breaking you? In this episode, Dave sits down with Tino Dietrich, Founder and CEO of The Dietrich Institute, for a conversation that goes far beyond business strategy. After a near-death experience forced him to confront everything, Tino gained a level of clarity most people never reach. Success, money, status none of it mattered. What did? His family, his purpose, and the realization that his life looked right on paper but felt misaligned. With 30+ years of experience, Tino explores the hidden cost of ambition. Why high performers win in business but lose at home, and why the issue is not communication, but the patterns behind it. He unpacks “crules,” the unconscious rules we follow, and how they quietly shape our decisions and relationships.

Most entrepreneurs are not stuck because of strategy, but something deeper. This week, Dave talks with Alexander Lyadov, Business Therapist, about the hidden mental barriers that hold founders back. After leading major businesses and managing a multimillion-dollar fund, Alexander found himself hitting the same invisible wall again and again.  He breaks down why entrepreneurs feel stuck, the loneliness of leadership, and the internal dilemmas that create paralysis and poor decisions.  Alexander shares a simple but powerful framework: understand where you are now, define the worst-case future, and clarify your true desired state. If you feel stuck or uncertain, this episode offers a new way to think about growth, decisions, and your path forward.

What if everything you thought was “safe” isn’t? In this episode, Dave Wescott sits down with Beau Turner, Founder & CEO of Abundant Mines, to unpack his move from real estate into Bitcoin. After watching his portfolio surge during a global shutdown, Beau realized something didn’t add up and started digging deeper. That journey led to a new path. Beau breaks down Bitcoin in simple terms, how mining works, why scarcity matters, and why he believes it is reshaping how value is stored and transferred. After losing $500,000 in a failed deal, Beau built Abundant Mines to bring transparency and simplicity to the space. Today, his company provides fully managed mining solutions designed to reduce risk and confusion. If you have been skeptical about Bitcoin, this episode may change how you think about money and investing.

What happens when a high-powered Wall Street attorney walks away from the predictable path and bets everything on coffee in Colombia? On this Tuesday's episode, Dave sits down with Adam Jason, Co-CEO of @The Green Coffee Company, Colombia’s largest coffee producer and a vertically integrated farm-to-cup business reshaping the global coffee market. Adam shares how he traded IPOs and Fortune 500 clients for mountain farms, language barriers, and high-stakes entrepreneurship in a foreign country. What followed was scaling to over 10,000 acres, 10 million coffee trees, and raising more than $100M from investors while building a pre-IPO company from the ground up. This conversation is about risk, conviction, and the reality of building something meaningful when nothing is guaranteed. From navigating cultural challenges and fragmented markets to leveraging the iconic Juan Valdez brand and building a direct farm-to-consumer advantage, Adam breaks down what it really takes to scale globally. If you have ever thought about leaving the safe path, entering an emerging market, or building something bigger than yourself, this episode is your wake-up call.

Do you have a message you want to get out about your business, service, or product, but struggle to connect with people when you pitch it in a room? In this episode of The Entrepreneurial Journey Podcast, Dave sits down with Fern Chan, CEO and Founder of Fern Chan Ventures, to unpack what it really takes to stand out, be heard, and make people care. Fern has spent 15+ years helping leaders, entrepreneurs, and educators become the kind of speakers people cannot ignore, from stages at the United Nations to intimate mastermind rooms. Her philosophy is simple. If you create a real connection, people will remember you. This conversation dives into the realities of entrepreneurship, from walking away from a stable career to betting on yourself, navigating fear, and building a business around what people already come to you for. Fern breaks down why most presentations fail, how storytelling changes everything, and the simple shifts that can instantly make you more impactful in any room. From ditching bullet points to opening with something unexpected, the goal is not perfection; it's a connection. As a bonus for listeners, Fern is offering a free downloadable copy of her book, How to Not Suck at Presentations. You can grab your copy here: https://lnkd.in/gKRD8q3b If you have ever struggled to communicate your value, connect with the right people, or confidently show up as yourself, this episode will challenge the way you think and give you a better way forward. Join us this Tuesday at 9:15 am PST for this lively and entertaining conversation!

Most businesses aren't losing money on ads because ads don't work. They're losing money because they don't understand how to use them. In this episode, Dave talks with Andy Janaitis, Founder and Chief Strategist at PPC Pitbulls, to break down why so many companies waste ad spend and what to do instead. Andy shares how to simplify paid ad strategy, focus on the metrics that actually matter, and build campaigns that are driven by profitability, not guesswork. From recognizing real demand to avoiding common traps in Google and Meta ads, this conversation is a practical look at what separates wasted spend from scalable growth.  If you are running ads or thinking about it, this episode will help you stop burning budget and start making smarter decisions

Anthony Scavo has spent nearly three decades in real estate development, construction, and operations, and today he is helping lead one of the most interesting plays in commercial real estate. As President and Partner at Basis Industrial, Anthony helps drive a fast-growing platform focused on multi-tenant small bay industrial and self-storage. What began as a self-storage development strategy evolved into something much bigger when Anthony and his team saw a shift in the market and made a smart move. Instead of forcing one path, they paid attention to what tenants needed, what the numbers were saying, and where the demand was going. In this episode, Anthony and Dave dig into the business of industrial real estate, the value of flexibility, and what it really takes to scale a company in a competitive market. Anthony shares how Basis grew from a small team into a multi-market operation with millions of square feet under management, why small bay industrial has become such a powerful asset class, and how customer service can become a real competitive advantage even in commercial real estate. They also discuss: • Why being adaptable matters more than being rigid • How to recognize when the market is telling you to change direction • The difference between chasing a deal and sticking to disciplined underwriting • Why tenant retention and service matter more than most owners realize • How to scale a team without losing accountability • What it means to be a good steward of investor capital Anthony brings an operator’s mindset to everything. He knows the numbers, understands construction, and stays close enough to the business to see problems before they grow. His perspective is practical, grounded, and shaped by years of experience in both institutional real estate and hands-on operations. And Anthony’s closing message is one worth remembering: Be kind.

Chance McClain is the founder of Heritage Films, a storytelling company that has produced more than 800 feature-length documentaries capturing family stories and life legacies. What started as a creative experiment eventually turned into a mission: preserving the voices, values, and memories that families wish they could keep forever. Before Heritage Films, Chance’s career bounced across the creative world. He worked in sports radio, wrote music and theater, produced commercials, and even created a Streamy-nominated project along the way. But everything changed when a friend asked him to film his father’s life story. That single interview became the first Heritage Film and opened Chance’s eyes to the power of documenting real lives. In this episode, Chance and Dave explore what happens when storytelling meets purpose. From filming hundreds of life histories to sitting with people at the most reflective moments of their lives, Chance shares the lessons he has learned about family, faith, leadership, and what really matters. They discuss: • How a creative side project became a business built around legacy • Why authenticity always wins over polished messaging • What hundreds of life stories have taught him about leadership and values • The surprising wisdom that comes from interviewing people near the end of their lives • Why entrepreneurs should document their own stories before it is too late Chance believes every family deserves to preserve its story. The real goal is not just recording memories, but capturing the values that shaped a life. His advice is simple and powerful: live a life that makes your kids want to remember your story.

Andrew Munoz is the Co-Lead Pastor of New Life Church in Everett, Washington, and has spent more than 16 years in pastoral ministry. He's married to Amanda and is raising three children, Lydia, June, and Silas. But Andrew’s story does not start in a megachurch or a spotlight. It begins in a small home church led by his parents, where he watched them love broken, ordinary people with extraordinary consistency. In this episode, Andrew and Dave unpack leadership from the inside out. From marathon training and mental discipline to navigating pastoral burnout, Andrew speaks candidly about identity, boundaries, and what it means to lead without losing your soul. He shares why burnout often stems from poor rhythms and misplaced identity, and how remembering that “Jesus died for the church, not me” changed his leadership forever. They dive into: Why identity must come before performance Building margin, rest, and personal devotion into daily life Leading change in organizations filled with “sacred cows” Communicating mission over preferences The power of serving your family before serving your platform Andrew also challenges leaders to turn down the noise. In a culture addicted to devices and distraction, he calls entrepreneurs, pastors, and parents back to stillness, reflection, and real conversation. This is a conversation about mission, margin, and servant leadership. Whether you are leading a business, a church, or a family, Andrew’s blueprint is simple and powerful: build trust, cast vision, and serve one another in love.

Ethan Hardinger built a business around something nobody wanted to touch. After starting his career in luxury real estate, Ethan realized he was hunting every deal just to get paid. Big checks, yes. Stability, no. What he wanted was a “chicken” that laid eggs. Recurring revenue. Predictable income. Something that worked while he slept . That search led him to an overlooked opportunity sitting in plain sight: filthy residential trash bins. Today, Ethan is the Founder and CEO of Bubble Binz, a residential trash bin cleaning company with over 35,000 subscription customers and a rapidly expanding franchise model. What started as a side experiment has evolved into a scalable, tech-enabled service business, powered by proprietary software, custom-built trucks, and a system designed for operational excellence. In this episode, Ethan and Dave dig into: • The moment he realized recurring revenue beats one-time commissions • How he validated a “weird” idea before going all in • Why niche service businesses can outperform flashy startups • Building proprietary tech to streamline thousands of stops • Franchising the system so others can “get in the race car and drive.” • Why customer experience is the ultimate growth strategy Ethan shares the lessons learned from trial and error, building trucks from scratch, investing heavily in software, and obsessing over customer service in an unglamorous industry.

Tim Packer walked away from a badge and a steady paycheck to live his dream. Tim spent 18 years as a police officer and detective before making one of the boldest decisions of his life. He left a secure career to pursue art full-time. What started as a side passion turned into a thriving, multi-million dollar art business built on originals, self-published prints, and direct-to-collector sales. But Tim did not stop there. After nearly losing his life to serious health complications, he realized his legacy was bigger than selling paintings. He launched the Tim Packer Art Academy to teach artists how to master both the creative and business sides of their craft. Through his #1 bestselling book, You Can Sell Your Art, and his growing online academy, Tim is helping thousands of artists move beyond the starving artist myth and build real income doing what they love . In this episode, Tim and Dave dig into: • Why mastery of skill must come before marketing • The difference between “pretty good” and unforgettable • How to find your unique voice • Why most creatives fail in product mode • The three paths to making a living as an artist • The power of the word “yet.” This is a conversation about art, courage, discipline, reinvention, and building something that lasts. If you are an entrepreneur, creative, or anyone sitting on a dream you have not acted on yet, this episode will challenge you.

Jonathan Sherrill is an entrepreneur, investor, and former manufacturing CEO who successfully exited the business he built from the ground up. In this episode, Jonathan and Dave unpack what makes an exit truly extraordinary. Not just financially, but emotionally and personally. Jonathan shares lessons from his own exit, why most sellers experience regret, and how understanding your deeper “why” early can change the outcome. They talk about preparation, defining non-negotiables, telling the right story to buyers, and navigating identity after the sale. Now a coach and advisor, Jonathan helps founders prepare for exits that maximize value while protecting legacy. This is a thoughtful conversation about selling on purpose, not by accident. "The Entrepreneurial Journey with Dave Wescott" is a weekly podcast airing LIVE at 9:15 a.m. PST on Dave's YouTube, Facebook, and LinkedIn profiles, and available ahead of your Thursday morning commute as an audio-only podcast on your favorite podcasting platform. This podcast is proudly sponsored by Sherpa CEO Coaching. Learn more at www.sherpaceo.com

When the founder breaks, the business often follows. Phil Neil knows this reality better than most. An entrepreneur, investor, and founder of Founders Compass, Phil has lived on both sides of the scoreboard. He scaled a medical supply business to more than $70 million in revenue and achieved an eight-figure exit, only to discover that success did not quiet the internal pressure to prove it was not just luck. When his next venture collapsed after an initial burst of momentum, the real lesson became clear. In this episode, Phil and Dave go deep into what happens when pressure distorts judgment and founders begin operating from fear, urgency, and reactivity. Phil shares his personal journey through rapid growth, pivoting during COVID, imposter syndrome, founder conflict, and burnout. More importantly, he explains how these experiences led him to build Founders Compass, a system designed to help founders strengthen their inner operating system before they break. They explore why founders suffer in silence, how decision quality collapses under sustained pressure, and why businesses often fail after the founder has already crossed an invisible line. Phil introduces concepts like the pressure cascade, the waterline method, and what it truly means to build an unbreakable founder. This conversation focuses on clarity, resilience, and learning to lead yourself before leading others. If you are a founder, CEO, or operator carrying more than you admit, this episode will hit close to home. Join us Tuesday morning at 9:15 am PST!

Jacob Vanderslice focuses on building something that lasts. Jacob is the Co-founder and Principal of VanWest Partners, where he oversees the creation of value-add self-storage portfolios across the country. But his entrepreneurial journey did not start in an office or a boardroom. Before real estate, Jacob served as a firefighter and arson investigator in Colorado, a role that shaped his thinking about risk, responsibility, and preparation. In this episode, Jacob and Dave dig into the real story behind his transition into real estate and why self-storage became his long-term focus. What began as residential fix-and-flip projects evolved into a disciplined investment platform built around downside protection, conservative leverage, and operational control. Jacob shares how early mistakes, development missteps, and selling too early taught him lessons that still guide every decision today. They talk candidly about what makes self-storage resilient, why supply is the biggest risk in the asset class, and how month-to-month leases allow operators to respond in real time. Jacob explains why his team self-manages their portfolio, why culture matters even across dozens of markets, and why growing slower is sometimes the smartest move. This conversation is about discipline, patience, and learning through failure. It is a grounded look at building wealth the long way, protecting the downside, and knowing when not to sell. If you want an honest perspective on real estate, risk, and long-term entrepreneurship, this is an episode worth your time.

Karen Caplan's family has created long-lasting trends in the produce and grocery industries that continue to this day. Karen is the former owner and CEO of Frieda's Branded Produce, a company that quite literally changed how America eats. Built on the vision of her mother, Frieda Caplan, the business introduced more than 200 fruits and vegetables to the U.S. market, including kiwifruit, spaghetti squash, sugar snap peas, dragon fruit, and purple sweet potatoes. In this episode, Dave sits down with Karen to unpack a remarkable entrepreneurial journey rooted in family, courage, and conviction. Karen shares what it was like growing up inside a family business, working alongside her sister, earning her leadership seat, and eventually buying the company from her mother. She opens up about the realities of running a family enterprise, navigating generational transitions, and making the difficult decision to sell the business after more than three decades. They also explore Karen’s evolution after exit, her move into executive coaching, and why experience, perspective, and passion matter more than theory when guiding leaders. This conversation is about legacy, leadership, and knowing when to hold on and when to let go. Can't wait for you to join us this Tuesday morning!

Some entrepreneurs chase growth. Jason Kruger chased understanding first. Jason is a Partner at Citrin Cooperman and the founder of Signature Analytics, an outsourced accounting and CFO advisory firm he launched in 2008, right as the financial world was coming apart. While most people were pulling back, Jason leaned in, betting that businesses would need clarity, discipline, and financial leadership more than ever. In this episode, Jason and Dave walk through what it really means to “know your numbers.” Jason shares why accounting is the foundation of every business, how ignoring cash flow quietly kills otherwise healthy companies, and why many entrepreneurs hit a wall around five million dollars in revenue. The issue is rarely effort. It is almost always infrastructure. Jason breaks down how fractional CFO and accounting services help growing companies bridge the gap between chaos and control. They talk about managing cash cycles, building reliable financial reporting, and why closing the books on time every month changes how leaders make decisions. Jason also shares lessons from growing Signature Analytics to over fifteen million dollars in revenue and navigating its successful acquisition by Citrin Cooperman. They also dig into: • Why cash flow, not revenue, keeps founders awake at night • How poor financial visibility limits growth and financing options • What buyers really look for during acquisitions and why preparation matters years in advance • The biggest mistakes first-time entrepreneurs make when hiring sales and finance roles • Why leaders must understand every part of their business, not just their craft Jason’s story is a reminder that financial discipline is not a burden. It is freedom. When leaders understand their numbers, they gain confidence, control, and the ability to build something that lasts.

Some leaders build companies. Val Lesak builds community. Val is the co-founder of Influential Encounters, an organization designed to support women in male-majority industries by creating spaces to meet, inspire, and influence one another. Her work grew out of real life experience. As the wife of a snow industry operator, a business professional, and a mother of three, Val saw firsthand the isolation, pressure, and unspoken challenges women often carry in industries built for men. In this episode, Val and Dave have a candid conversation about the realities behind the work. They talk about the mental load carried by women at home and in business, the resentment that can quietly build during long snow seasons, and the tools Val had to learn to navigate those moments with clarity and grace. She shares how breathwork, prayer, and community became essential tools not just for survival, but for growth. Val explains how Influential Encounters started with a single dinner in Boston and grew into sold-out events, a national conference, and an ambassador program designed to provide ongoing support, mentorship, and skill-building. The focus is not surface-level networking, but real connection, accountability, and leadership development that continues long after an event ends. They also explore the role of women in building stronger businesses, why mixed leadership teams outperform siloed environments, and how communication, boundaries, and conviction allow people to lead with confidence without losing who they are. Val’s story is about humility, discipline, and staying grounded while building something meaningful. It is a reminder that leadership is not about having it all at once, but about knowing what matters most in each season. If you care about people, culture, and building organizations where everyone can thrive, this episode is a must-listen.

John Giegerich returns to the show with a clear message for entrepreneurs and leadership teams: if you wait until January to plan the year ahead, you are already behind. As a Partner at CEO Coaching International and a former senior leader in capital markets and banking, John has spent decades helping CEOs turn vision into results. In this episode, John and Dave break down how elite leadership teams prepare for the year ahead. From building the plan before the calendar flips to launching teams at full speed on day one, John shares the frameworks, discipline, and mindset required to win the year before it even starts. They dive into the power of focus, why most companies fail by chasing too many priorities, and how narrowing the year to three true objectives changes everything. John walks through his proven planning process, including executive pre-work, strategy and execution sessions, 13-week execution marches, and the accountability systems that keep teams aligned when pressure hits. They also discuss: • Why annual planning must happen in October or November, not January • How to avoid losing the first quarter before it begins • The difference between purpose, passion, and real execution • Why discipline beats motivation every time • How resilience and focus determine long-term success This episode is a practical playbook for CEOs seeking clarity, alignment, and momentum heading into next year. No theory. No fluff. Just proven leadership discipline from someone who has seen what works and what fails. If you want your team prepared, focused, and executing from day one, this is a conversation you need to hear.

Robert Feldman is on the front lines of one of the biggest challenges facing homeowners and businesses today. As the founder of WOWS Fire Insurance Services, he specializes in insuring homes in high-risk fire zones that many carriers avoid. In this episode, Robert and Dave break down how wildfires have reshaped the insurance industry and why the future of coverage depends on education and prevention. Robert explains fire hardening, what homeowners must do to make properties defensible, and why insurance alone cannot replace what is lost in a fire. This is an essential conversation about responsibility, adaptation, and protecting what matters most in a changing world. "The Entrepreneurial Journey with Dave Wescott" is a weekly podcast airing LIVE at 9:15 a.m. PST on Dave's YouTube, Facebook, and LinkedIn profiles, and available ahead of your Thursday morning commute as an audio-only podcast on your favorite podcasting platform.

Tommy Sutherland built his career the hard way. Born in Scotland, he left school at fifteen and went straight to work. By twenty-three, he launched his first company and exited just two years later, kicking off a 25-plus-year journey of building, losing, rebuilding, and investing across the U.S., U.K., and Asia. In this episode, Tommy and Dave talk about grit, risk, and what it really takes to last as an entrepreneur. Tommy shares lessons from industrial services, electrification, and infrastructure, why workforce development matters more than ever, and how discipline and resilience shaped his leadership. This is an honest conversation about building businesses from the ground up and staying in the fight when things get hard. "The Entrepreneurial Journey with Dave Wescott" is a weekly podcast airing LIVE at 9:15 a.m. PST on Dave's YouTube, Facebook, and LinkedIn profiles, and available ahead of your Thursday morning commute as an audio-only podcast on your favorite podcasting platform. This podcast is proudly sponsored by WESTERN Snow Plows. Find out more at www.westernplows.com This podcast is also sponsored by Sherpa CEO Coaching. Learn more at www.sherpaceo.com

Billy Blough, National Accounts and Sales Manager for Douglas Dynamics, joins the show to share what really drives success in the snow and ice industry. Billy supports fleet contractors across the country and explains why the right plow is only half the story. The other half is the relationship. He talks about Douglas Dynamics’ commitment to building Western, Fisher, and SnowEx equipment in-house, their ability to scale during major storms, and why reliability determines whether a contractor wins or loses a season. We dig into fleet strategy, the importance of fast hookups, and the impact of new tools like the Pile Driver pusher box. A practical, insider look at what it takes to run a high-performing snow operation.

Kinder Smoots is the Executive Director of Eagle Wings disAbility Ministries, serving more than 2,200 adults with developmental disabilities in the North Puget Sound. Her journey began after the loss of her daughter Kayla, when volunteering became a path toward purpose and healing. In this episode, Kinder shares how a simple potluck for 60 people unexpectedly grew into a 240-person celebration and sparked a ministry that now offers dozens of free programs each year. We talk about grief, calling, leadership, and the importance of seeing every person as created in God’s image. For the next month, any business donation to Eagle Wings through the mBridge Global website will be matched up to $1,000. Tune in for a powerful, hope-filled conversation. Donate here: https://secure.givelively.org/donate/business-2-missions-dba-mbridge/eagle-wings-ministries Or, text eaglewings to #44321 to donate!

Zech Strauser has spent his life building businesses with grit, purpose, and a deep love for the outdoors. From launching Strauser Nature’s Helpers to creating Urture Apparel and Outfitters, Zech is driven by a simple mission: improve people, improve the trades, and leave everything better than he found it. In this episode, he and Dave talk about the early days of hauling mulch, the lessons that shaped him as a leader, and why the trades deserve a brand that reflects their pride and hard work. Zech shares what he has learned about taking chances, developing people, and building a legacy rooted in service and community. Tune in for an honest look at leadership, growth, and staying true to who you are. This podcast is sponsored by Western Snow Plows. Learn more at www.westernplows.com This podcast is also sponsored by Sherpa CEO. Learn more at www.SherpaCEO.com

David Morgan has spent his life studying honest money and real value. What started at age eleven, when he noticed silver disappearing from U.S. coins, grew into a lifelong pursuit of financial clarity and responsible investing. After learning the hard way through early mistakes, David launched The Morgan Report to help people avoid gambling in the markets and make decisions based on discipline and truth. In this episode, he and Dave talk about sound money, global shifts in power, why central banks are buying gold, and what every entrepreneur needs to understand about protecting wealth. Tune in for a clear, practical guide to thinking differently about money, markets, and long-term responsibility. "The Entrepreneurial Journey with Dave Wescott" is a weekly podcast airing LIVE at 9:15 a.m. PST on Dave's YouTube, Facebook, and LinkedIn profiles, and available ahead of your Thursday morning commute as an audio-only podcast on your favorite podcasting platform. This podcast is proudly sponsored by WESTERN Snow Plows. Find out more at www.westernplows.com This podcast is also sponsored by Frost Solutions. Learn more at http://www.frostsolutions.io

Mike Rohrbach has spent his life building champions on the field, in the locker room, and in faith. A former University of Washington football captain, Rose Bowl champion, and longtime team chaplain for the Seattle SuperSonics and UW athletics, Mike’s greatest legacy is not in the record books. It is in the lives he has changed through Run to Win Outreach, the youth sports ministry he co-founded with his wife Karen in 1991. He and Dave discuss faith, leadership, and purpose, as well as Mike’s lifelong mission to “walk the talk and run to win.” His story is both a playbook and a testimony, a reminder that success is not about titles, but about showing up, staying faithful, and serving others. "The Entrepreneurial Journey with Dave Wescott" is a weekly podcast airing LIVE at 9:15 a.m. PST on Dave's YouTube, Facebook, and LinkedIn profiles, and available ahead of your Thursday morning commute as an audio-only podcast on your favorite podcasting platform. This podcast is proudly sponsored by WESTERN Snow Plows. Find out more at www.westernplows.com This podcast is also sponsored by Frost Solutions. Learn more at http://www.frostsolutions.io

Ever wonder what it takes to build a company that turns into the storm instead of running from it? This week, Dave sits down with Kevin Stonitsch, owner of Adirondack Customs and Bison Facility Management Services. Kevin’s story is all about grit, creativity, and staying true to your values, from building custom homes to managing snow and ice across half of New York. We discuss smart growth, understanding your numbers, and why ownership and integrity matter more than any contract. "The Entrepreneurial Journey with Dave Wescott" is a weekly podcast airing LIVE at 9:15 a.m. PST on Dave's YouTube, Facebook, and LinkedIn profiles, and available ahead of your Thursday morning commute as an audio-only podcast on your favorite podcasting platform. This podcast is proudly sponsored by WESTERN Snow Plows. Find out more at www.westernplows.com This podcast is also sponsored by Frost Solutions. Learn more at www.frostsolutions.io

This week, I sit down with Ryan Hogan, a Navy Reservist, serial entrepreneur, and Co-Founder and CEO of Talent Harbor. Ryan knows what it means to scale a business, challenge an industry, and lead with clarity. Before founding Talent Harbor, Ryan helped turn Hunt A Killer from a small idea into a $205 million global brand. Along the way, he saw firsthand how broken the recruiting world had become. Too many commissions, too many middlemen, and too few people focused on what really matters — finding the right fit for the right team. That realization sparked his next venture. With Talent Harbor, Ryan is on a mission to rebuild how companies hire. His flat-fee, embedded recruiting model strips out the noise and focuses on what drives long-term success: alignment, accountability, and trust. In our conversation, Ryan and I talk about: • The lessons he brought from his time in the Navy into entrepreneurship • What building Hunt A Killer taught him about systems, leadership, and decision-making • Why so many founders make the same hiring mistakes again and again • How to make recruiting a core part of your business, not an afterthought • Why the old hiring model still dominates today — and what to do about it Ryan’s story is about more than fixing recruiting. It’s about leadership, discipline, and the willingness to question how things have always been done. Whether you’re hiring your first team member or scaling a national company, this episode will challenge how you think about people, process, and growth. It’s a conversation about building smarter, leading better, and creating a business that lasts.

Christian Reed launched REEKON Tools to change how builders measure, plan and execute. In the process he uncovered something bigger. In this episode we dig into how Christian went from MIT machine-shop nights and Army engineer deployments to founding a hardware-first startup from his own garage, why the conventional tool industry is overdue for a makeover and how REEKON’s digital tape measure is just the first act, the shock of rising input costs, what he truly means when he says: “If you can’t make content and you don’t appreciate design, you’re just shooting yourself in the foot,” and the bootstrap mindset of skipping VC, owning your path, and laying the groundwork for long-term impact. Christian’s story is a serious playbook for founders who are facing margin squeeze, trade-headwinds, global supply-chain risk, and still want to build something meaningful. This podcast is proudly sponsored by WESTERN Snow Plows. Find out more at www.westernplows.com This podcast is also sponsored by Frost Solutions. Learn more at www.frostsolutions.io

Mark Bradley started as a steamfitter in a nuclear plant, then he built one of North America’s top landscape companies from scratch. From there, he built LMN, the industry’s leading business management software, helping thousands of contractors grow, train crews, and scale smarter. Now? He’s reinventing again with LeanScaper, a movement that’s part community, part mastermind, and part AI-driven workflow software reshaping how field companies operate. But the real story here isn’t about revenue or tech, it’s about redemption, purpose, and integration. After years of grinding 100-hour weeks and watching his health and relationships break down, Mark realized something: He didn’t want work-life balance; he wanted an integrated life. In this conversation with Dave, Mark shares: • How he turned burnout into a breakthrough. • Why your calendar is the ultimate mirror of your values. • The five goals that guide his life (and why business is last on the list). • How faith, family, and purpose now define his version of success. • The systems every entrepreneur needs to lead rationally, not react emotionally. If you’ve ever built your business at the expense of your health, your marriage, or your peace of mind, then this episode will hit home. And Mark’s story is proof that you can rebuild, automate, and find alignment again. This isn’t just about landscaping, it’s about life-scaping and designing a life you don’t need a vacation from. "The Entrepreneurial Journey with Dave Wescott" is a weekly podcast airing LIVE at 9:15 a.m. PST on Dave's YouTube, Facebook, and LinkedIn profiles, and available ahead of your Thursday morning commute as an audio-only podcast on your favorite podcasting platform. This podcast is proudly sponsored by WESTERN Snow Plows. Find out more at www.westernplows.com This podcast is also sponsored by FROST Solutions. Learn more at www.frostsolutions.io

From coding in a college basement to leading a digital studio trusted by Adobe, Gap, Stanford, and DocuSign — Ben Callahan has walked the long, messy, and exhilarating road of entrepreneurship . He didn’t start out wanting to be a business owner. In fact, he once swore he never would. But after years of building other people’s dreams and sleeping in his office for someone else’s paycheck, Ben had a realization: if he was going to sacrifice that much, it better be for something he owned . That decision sparked a journey that took him from scrappy startup projects (doing anything to pay the bills) to founding Sparkbox, a digital powerhouse at the cutting edge of design systems and technology. Along the way, he discovered hard-won lessons every entrepreneur needs to hear: Why “doing good work” isn’t enough — it’s just the cost of entry. How relationships and storytelling open doors to blue-chip clients. What it really takes to transition from practitioner to mentor and coach. Why his personal mantra, “Stay in Learning Mode,” might be the ultimate entrepreneurial advantage. This episode isn’t just about websites or tech. It’s about grit, timing, reinvention, and the courage to bet on yourself. Ben brings 20+ years of experience, but more importantly, he brings perspective — and a roadmap for anyone ready to level up their own entrepreneurial journey. "The Entrepreneurial Journey with Dave Wescott" is a weekly podcast airing LIVE at 9:15 a.m. PST on Dave's YouTube, Facebook, and LinkedIn profiles, and available ahead of your Thursday morning commute as an audio-only podcast on your favorite podcasting platform. This podcast is proudly sponsored by WESTERN Snow Plows. Find out more at www.westernplows.com This podcast is also sponsored by Frost Solutions. Learn more at http://frostsolutions.io

This week’s podcast guest is a certified beast — and not just on your TV screen. You might know him as the strategic mastermind from MTV’s The Challenge — But behind the scenes? He’s been building an entrepreneurial empire that now generates over $250 MILLION in annual revenue. Recently featured in Inc. Magazine Multi-company founder and investor Reality TV icon turned business tactician I’m beyond excited to welcome Wes Bergmann to the show — We’re talking: What reality TV taught him about strategy, pressure, and human psychology How he built multiple companies without losing his mind The secret to turning public attention into real entrepreneurial leverage Why business is the ultimate competition This episode isn’t just entertainment — It’s a masterclass in long-game thinking, personal evolution, and building wealth without selling your soul. Learn more about BetaBlox at www.betablox.com "The Entrepreneurial Journey with Dave Wescott" is a weekly podcast airing LIVE at 9:15 a.m. PST on Dave's YouTube, Facebook, and LinkedIn profiles, and available ahead of your Thursday morning commute as an audio-only podcast on your favorite podcasting platform. This podcast is proudly sponsored by WESTERN Snow Plows. Find out more at www.westernplows.com This podcast is also proudly sponsored by Frost Solutions. Find out more at www.frostsolutions.io WesBergmann #TheChallenge #Entrepreneurship #BusinessStrategy #RealityTV #PodcastDrop #Founders #Mindset #FromFamousToFounder #BusinessGrowth

Ed Harris, Founder and CEO of Harris Northwest Advisors, shares his path from Wall Street investment banking to helping entrepreneurs sell their companies in the lower middle market. Ed reflects on lessons from advising billion-dollar deals, working with Microsoft co-founder Paul Allen, and leading startups to successful exits. He breaks down what makes a business attractive to buyers, work-life balance in entrepreneurship, and why success comes down to out-executing competitors. "The Entrepreneurial Journey with Dave Wescott" is a weekly podcast airing LIVE at 9:15 a.m. PST on Dave's YouTube, Facebook, and LinkedIn profiles, and available ahead of your Thursday morning commute as an audio-only podcast on your favorite podcasting platform. This podcast is proudly sponsored by WESTERN Snow Plows. Find out more at www.westernplows.com This podcast is also proudly sponsored by Frost Solutions. Find out more at www.frostsolutions.io

This week, Dave welcomes Jessica Cvetic, Founder of Citrus Aesthetics Med Spa and Citrus Franchising, who shares how she transformed a solo practice into a thriving brand now preparing for national expansion. From her start in emergency medicine to her move to aesthetics, and lessons learned from being fired, Jessica discusses why ethics, natural results, and strong client relationships set Citrus apart. "The Entrepreneurial Journey with Dave Wescott" is a weekly podcast airing LIVE at 9:15 a.m. PST on Dave's YouTube, Facebook, and LinkedIn profiles, and available ahead of your Thursday morning commute as an audio-only podcast on your favorite podcasting platform. This podcast is proudly sponsored by WESTERN Snow Plows. Find out more at www.westernplows.com This podcast is also proudly sponsored by Frost Solutions. Find out more at www.frostsolutions.io

This week, Dave chats with Don Zerby, Founder and President of EcoLawn, who shares how he turned a teenage lawn-mowing hustle into a thriving, environmentally conscious lawn care company. Don talks about building a top workplace culture, the power of Profit First budgeting, and why continuous learning keeps his business strong after nearly five decades. "The Entrepreneurial Journey with Dave Wescott" is a weekly podcast airing LIVE at 9:15 a.m. PST on Dave's YouTube, Facebook, and LinkedIn profiles, and available ahead of your Thursday morning commute as an audio-only podcast on your favorite podcasting platform. This podcast is proudly sponsored by WESTERN Snow Plows. Find out more at www.westernplows.com This podcast is also proudly sponsored by Frost Solutions. Find out more at www.frostsolutions.io

This week, Ben George, President of Grower and Controlled Environment Agriculture at BFG Supply, shares his path from building a family greenhouse business to leading strategy at one of the nation’s largest horticultural suppliers. Ben reflects on lessons learned from scaling International Greenhouse Company, the risks and rewards of growth, and why failure is often a better teacher than success. "The Entrepreneurial Journey with Dave Wescott" is a weekly podcast airing LIVE at 9:15 a.m. PST on Dave's YouTube, Facebook, and LinkedIn profiles, and available ahead of your Thursday morning commute as an audio-only podcast on your favorite podcasting platform. This podcast is proudly sponsored by WESTERN Snow Plows. Find out more at www.westernplows.com This podcast is also proudly sponsored by Frost Solutions. Find out more at www.frostsolutions.io