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Why Optimism Is a Founder’s Greatest Advantage – Dick Pfister | S7 E4
Description
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.
Dick shares how his entrepreneurial journey began at just 13 years old, starting small businesses in rural Wisconsin before eventually working on the floor of the Chicago Mercantile Exchange alongside some of the world’s greatest investors. Those experiences ultimately led him to co-found Altegris, pioneer alternative investments for independent advisors, and later launch AlphaCore after realizing traditional wealth management wasn’t serving entrepreneurs well enough.
But this conversation goes far beyond investing.
Dick explains why optimism has become one of his greatest competitive advantages, how his wife gave him the confidence to start over after a successful exit, and why measuring your health is just as important as measuring your finances.
Throughout the conversation, we explore entrepreneurship, wealth management, investing, leadership, family, health, resilience, and the habits that help founders build successful businesses while living meaningful lives.
Whether you’re growing your first company or preparing for a major liquidity event, Dick shares practical lessons every entrepreneur can apply.
In this episode you’ll learn:
- Why traditional investing may no longer be enough for entrepreneurs
• How alternative investments can improve portfolio diversification
• Why optimism is a founder’s greatest competitive advantage
• The importance of measuring your health as carefully as your finances
• How daily habits compound into long-term success
• Why having the right life partner changes everything
• How setbacks create stronger entrepreneurs
• Why continuous learning never stops
• How trust becomes the foundation of every successful business
Dick also shares how launching businesses as a teenager shaped his entrepreneurial mindset, why endurance sports became part of his daily routine, and how AlphaCore was born from challenging conventional wisdom about wealth management.
If you enjoy conversations about entrepreneurship, founder mindset, investing, wealth management, business leadership, resilience, personal development, and building meaningful businesses, you’ll enjoy this episode.
This episode of A Founder’s Life is brought to you by Thankz, helping founders scale with reliable remote talent.
Email founders@thankz.com with the subject A Founder’s Life for preferred pricing.
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/
Website