The Entrepreneurial Journey

Hosted by Dave Wescott

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Episodes

164

Latest episode

Aug 2026

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About the show

Introducing The Entrepreneurial Journey with Dave Wescott, a dynamic and insightful video podcast that serves as your guide on the entrepreneurial journey. Join Dave and a lineup of inspiring business professionals, thought leaders, and change-makers every Tuesday at 9:15 am PST on LinkedIn and YouTube for engaging conversations that ignite your entrepreneurial spirit. In each 30-minute episode, Dave and his guests dive deep into the topics that matter most to aspiring and established entrepreneurs. From conquering self-doubt and scaling your business to discovering the perfect idea and mastering investment strategies, we explore the essential elements that pave the path to success. But it doesn't stop there! The Entrepreneurial Journey goes beyond business-centric discussions; we spotlight non-profit organizations that profoundly impact and change the world. Special guest appearances from these organizations provide invaluable insights and inspiration to give back and create meaningful change. So, whether you're an aspiring entrepreneur looking for guidance, a seasoned business owner seeking fresh perspectives, or someone passionate about social impact, The Entrepreneurial Journey is your compass to entrepreneurial excellence. Tune in, gain valuable insights, and set your course for success in the ever-evolving business world. Learn more about Dave at DaveWescott.com or follow him on most platforms at @thedavewescott.

Listen to episodes

60 recent

August 11, 202654 min

Is Your Childhood Running Your Company? | 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.

August 4, 202648 min

A Crooked Compass Beats a Perfect Plan | The Entrepreneurial Journey

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.

July 28, 202649 min

Build a Business Worth Buying | The Entrepreneurial Journey

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.

July 21, 202651 min

Habits That Build Lasting Wealth | The Entrepreneurial Journey

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 .

July 14, 202648 min

What Story is Your Business Telling? | The Entrepreneurial Journey

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.

July 7, 202656 min

How Great Investors See What Others Miss | The Entrepreneurial Journey

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.

June 30, 202645 min

Building an $11M Business With $0 Debt | The Entrepreneurial Journey

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.

June 23, 202653 min

Building a Business and Finishing 100 Miles | The Entrepreneurial Journey

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.

June 16, 202647 min

The Credibility Shortcut Entrepreneurs Ignore | The Entrepreneurial Journey

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.

June 9, 202655 min

Sales Won’t Fix a Broken Business | The Entrepreneurial Journey

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.