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:

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:

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