The bold actions of leaders during times of crisis can redefine entire industries.

In this episode, I’m joined by Jim McKelvey, co-founder of Block, Inc. (formerly Square, Inc.) and author of The Innovation Stack. We dive into what it means to be a true entrepreneur and the challenges of breaking new ground.

Jim shares his personal journey from outsider to innovator, the influence of his unconventional upbringing, and the pivotal moments that shaped his approach to business and and creativity. We also explore the power of using discomfort as a tool for innovation and how being an outsider can be an asset when challenging the status quo.

Tune in to hear his stories and gain inspiration for your own entrepreneurial journey.

Specifically, this episode highlights the following themes:

• Turning setbacks into breakthroughs
• Overcoming regulatory challenges in tech startups
• The evolving role of AI in solving complex problems

Link from this episode:

• Get to know more about Jim McKelvey: https://en.wikipedia.org/wiki/Jim_McKelvey
• Learn more about Block, Inc.: https://investors.block.xyz
• Read his book The Innovation Stack: https://www.amazon.com/Innovation-Stack-Building-Unbeatable-Business/dp/0593086732/ref=sr_1_1
• Get to know more about Robert Tuchman: https://www.linkedin.com/in/roberttuchman

It's inspiring to hear how someone can turn a simple idea into a billion-dollar business. Angie Hicks, the Co-Founder of Angi, shares her journey from humble beginnings to leading one of the most well-known names in home improvement.

Angie Hicks is the Co-Founder of Angi (formerly Angie’s List). She started Angie’s List in 1995, which has grown over nearly 30 years from supporting a few cities to the first national digital directory for home improvement. Angie opens up about the challenges she faced as a young entrepreneur, including learning to sell door-to-door and figuring out how to scale the business.

We also talk about the significance of customer feedback and how it became a guiding force for growth. Angie shares why staying adaptable is crucial in a rapidly evolving market and what has kept her driven for almost three decades.

Angie’s journey shows what’s possible when you stick with it and keep learning along the way. Tune in to hear her candid stories and practical insights—it’s the kind of advice every entrepreneur could use.

Specifically, this episode highlights the following themes:

• Leveraging customer feedback to shape business strategy
• The evolution from an offline service to a digital-first company
• Why perseverance is a vital trait for entrepreneurs

Link from this episode:

• Get to know more about Angie Hicks: https://www.linkedin.com/in/angie-hicks-30566
• Learn more about Angi: https://www.angi.com
• Get to know more about Robert Tuchman: https://www.linkedin.com/in/roberttuchman

It’s essential to stay ahead of estate planning, especially with tax changes looming.

In this episode, we cover the essentials of estate planning, business planning for small and mid-sized businesses, and retirement strategies centered on life insurance and annuities. I sit down with Bill Bell, Vice President of Advanced Sales at Penn Mutual, to discuss the impact of upcoming tax law changes, particularly the scheduled reduction in wealth transfer allowances.

We also touch on why it’s critical to act before the 2026 deadline and how ultra-wealthy clients can stay informed despite their busy schedules.

Trust me, you’ll walk away with valuable insights and strategies that you can act on today. Tune in now and stay ahead of the curve!

Specifically, this episode highlights the following themes:

• Maximizing wealth transfer before the tax law changes in 2026
• The importance of life insurance in estate and business planning
• How Penn Mutual’s mutuality benefits clients and financial professionals

Link from this episode:

• Get to know more about Bill Bell: https://www.linkedin.com/in/billbellpml
• Learn more about Penn Mutual: https://www.pennmutual.com
• Listen to Life Matters – A Penn Mutual Podcast: https://podcasts.apple.com/us/podcast/life-matters-a-penn-mutual-podcast/id1700971729
• Get to know more about Robert Tuchman: https://www.linkedin.com/in/roberttuchman