About Doug Thorpe: Doug Thorpe is an executive coach, leadership advisor, and founder of a highly regarded leadership and management development firm serving both Fortune 500 companies and growth-focused entrepreneurs. Shaped early by watching his single mother build an interior design business from scratch, Doug learned firsthand the realities of risk, responsibility, and resilience.

Over the course of his career, he has combined that entrepreneurial foundation with a deep commitment to servant leadership, mentorship, and faith-driven wisdom. Doug now specializes in helping owner–founders of middle-market companies—typically $5M–$50M in revenue with teams of 10+—move beyond “founder-itis,” build high-functioning leadership teams, and turn their companies into scalable, saleable assets.

In this episode, Gary and Doug Thorpe discuss:

• Growing up around entrepreneurship and how early exposure to risk and responsibility shapes leaders
• The role of mentors in developing wisdom—and why experience alone isn’t enough
• Fear, limiting beliefs, and why change feels harder than it actually is
• Why many founders struggle to scale—and how “founder-itis” caps growth
• What it really takes to build a leadership team and a saleable business asset

Key Takeaways:

• Leadership often begins with service, not authority. Early responsibility and a desire to help others can quietly shape how someone leads later in life.
• Experience only becomes wisdom when paired with honest self-reflection. Without reflection, people repeat the same patterns—mistakes included.
• Fear is rarely about the change itself. It’s about the story we tell ourselves about what might happen if we fail.
• Growth stalls when founders believe only they can do things “the right way.” Building systems and trusting others is the difference between a lifestyle business and a saleable one.

"There is a value in finding out a way to claim those wins and stack them up like blocks in your foundation." — Doug Thorpe

Connect with Doug Thorpe:

Website: https://dougthorpe.com/

LinkedIn: https://www.linkedin.com/in/dougthorpe/

Podcasts: https://podcasts.dougthorpe.com

Twitter: https://twitter.com/dougthorpe_com

Facebook: https://facebook.com/headwayexec

Instagram: https://instagram.com/dougthorpe_com

YELP: https://www.yelp.com/biz/headwayexec-houston-4

To get in touch with Gary:

Website: https://betterpathtraining.com/

LinkedIn: https://www.linkedin.com/in/gsinderbrand/

Audio production by Turnkey Podcast Productions. You're the expert. Your podcast will prove it.

About Dean Mathews: Dean Mathews is the founder and CEO of OnTheClock, a time‑tracking and payroll platform serving over 18,000 businesses with tools for employee time tracking, scheduling, payroll, and PTO. A self‑taught developer who started by building custom software for local companies, Dean grew OnTheClock from a kitchen‑table side project into a scalable SMB solution known for being easy, reliable, and intuitive to use. Today, he leads a growing team focused on practical product design, strong culture, and helping small businesses run more efficiently while building happier, more productive teams.

In this episode, Gary and Dean Mathews discuss:

• Dean’s entrepreneurial and technical origin story
• The creation and growth of OnTheClock
• Product philosophy: usability, reliability, and UX
• Intuition, pattern recognition, and the emotional side of entrepreneurship

Key Takeaways:

• Some of the most valuable business lessons don’t come from classrooms or formal training. They come from making decisions without a safety net and owning the outcome.
• Responsibility and real consequences change how you think—and when the stakes are real, learning accelerates fast.
• Confidence grows through repetition, not perfection. Getting things wrong is often part of getting better.
• Leadership isn’t about having all the answers. It’s about being willing to learn, adapt, and move forward anyway.

"There's always a fear element…But fear isn't the thing, it's the courage that matters." — Dean Mathews

Connect with Dean Mathews:

Website: https://www.ontheclock.com/

LinedIn: http://linkedin.com/in/dean-mathews-yes | https://www.linkedin.com/company/ontheclock-com

Facebook: https://www.facebook.com/ontheclocktimeclock

YouTube: https://www.youtube.com/user/OnTheClockTimeClock

To get in touch with Gary:

Website: https://betterpathtraining.com/

LinkedIn: https://www.linkedin.com/in/gsinderbrand/

Audio production by Turnkey Podcast Productions. You're the expert. Your podcast will prove it.

About Anders Jones: Anders Jones is the co-founder and CEO of Facet Wealth, a financial planning firm built to serve the massively underserved mass affluent market with affordable, subscription-based advice from dedicated CFP professionals. Prior to Facet, Anders was a founding partner of Argyle Ventures. Argyle invests in emerging startup markets, with a focus on advertising, technology, financial technology, and healthcare IT. Prior to Argyle, Anders was on the early team at LiveRamp (acquired by Acxiom for $310 million), and has been involved as an investor or advisor in many other startups in Silicon Valley.

In this episode, Gary and Anders Jones discuss:

• Why the traditional asset-based advisory model excludes millions who still need real guidance
• How the DOL fiduciary rule exposed a massive cost-of-service problem in financial advice
• The shift from B2B to direct-to-consumer—and what finally unlocked growth
• Why human advisors, trust, and empathy still matter in an increasingly automated world

Key Takeaways:

• Entire industries can overlook enormous opportunities simply because serving them doesn’t fit existing business models. That doesn’t mean the need isn’t real—or urgent.
• Financial advice isn’t just about numbers. Trust, empathy, and consistent human connection are often more valuable than technical optimization.
• Scaling service doesn’t require sacrificing quality, but it does require rethinking how time, technology, and human expertise are allocated.
• For many people, the real competition isn’t another firm—it’s doing nothing. Education and clarity are often the first steps to meaningful engagement.

"We refer to our advisors as therapists with calculators." — Anders Jones

Connect with Anders Jones:

Website: https://facet.com/

LinkedIn: https://www.linkedin.com/in/anders-jones/

Email: anders@facet.com

To get in touch with Gary:

Website: https://betterpathtraining.com/

LinkedIn: https://www.linkedin.com/in/gsinderbrand/

Audio production by Turnkey Podcast Productions. You're the expert. Your podcast will prove it.