Podcast

A Founder's Life:

Balancing Entrepreneurship, Family, Health, & Fun​

Podcast

A Founder's Life:

Balancing Entrepreneurship, Family, Health, & Fun​

Why Optimism Is a Founder’s Greatest Advantage – Dick Pfister | S7 E4

Most entrepreneurs spend years building wealth, but very few spend the same amount of time learning how to protect it.

In this episode of A Founder’s Life, Leo Gestetner sits down with Dick Pfister, Founder and CEO of AlphaCore Wealth Advisory, to discuss entrepreneurship, investing, wealth management, and the mindset required to build lasting financial success.

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Guest Info

Dick Pfister is the Founder and CEO of AlphaCore Wealth Advisory, a national wealth management firm specializing in helping entrepreneurs, business owners, and families navigate complex financial lives. After co-founding and successfully exiting Altegris, one of the pioneers in alternative investments, Dick launched AlphaCore to redefine wealth management by combining institutional-quality alternative investments with comprehensive financial planning. Today, the firm oversees more than $12 billion in assets for clients across the United States.

A lifelong entrepreneur, Dick started his first business at just 13 years old and has spent his career building companies around innovation, integrity, and long-term thinking. Outside of work, he’s a devoted husband, father of three, endurance athlete, and passionate advocate for continuous learning. His leadership philosophy centers on optimism, disciplined risk management, and helping entrepreneurs build lasting wealth while living meaningful, balanced lives.

About this Episode

Most entrepreneurs spend years building wealth, but very few spend the same amount of time learning how to protect it.

In this episode of A Founder’s Life, Leo Gestetner sits down with Dick Pfister, Founder and CEO of AlphaCore Wealth Advisory, to discuss entrepreneurship, investing, wealth management, and the mindset required to build lasting financial success.

Highlights

  • Early Career: Started his first business at 13, delivering ice cream and later launching multiple small businesses before college.
  • Financial Breakthrough: Worked on the Chicago Mercantile Exchange alongside legendary investors, developing a deep understanding of risk management.
  • Major Exit: Co-founded Altegris, helping democratize access to alternative investments before successfully selling the business.
  • Entrepreneurial Pivot: Founded AlphaCore Wealth Advisory to modernize wealth management using alternative investments instead of traditional 60/40 portfolios.
  • Leadership Philosophy: Believes optimism is one of an entrepreneur’s greatest competitive advantages.
  • Health Journey: Uses endurance training, sleep tracking, and daily fitness routines to optimize performance.
  • Family First: Credits his wife as his greatest supporter and biggest influence in taking the leap to start AlphaCore.
  • Core Advice: Assume people are good, fair, and honest—and build businesses around trust and long-term relationships.

Resources

Connect with Today’s Guest – Dick Pfister

AlphaCore Website: https://alphacore.com/
AlphaCore YouTube: https://www.youtube.com/@AlphaCoreWealthAdvisory
Upside Capture Podcast:
– Spotify: https://open.spotify.com/show/67pBO2WB5qXlV7MEwQ48Kg?si=de3d6fdb84714cb6
– Apple: https://podcasts.apple.com/us/podcast/upside-capture/id1888226015
– Dick’s LinkedIn Account: https://www.linkedin.com/in/dickpfister/ – AlphaCore LinkedIn Account: https://www.linkedin.com/company/alphacorewealthadvisory/

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