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.