Avoiding the Regrets of Success: A Guide for Entrepreneur Fathers with Ryan Deiss

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Jun 18, 2025

Ryan Deiss, an entrepreneur and family man, shares his heartfelt journey of balancing success with family connection. He candidly discusses the moment he realized his emotional absence was detrimental to his marriage and kids. Ryan reveals how a pivotal moment with his son and learning to prioritize presence over perfection transformed his approach to fatherhood. He also introduces a family-first calendar ritual that fostered trust and rhythm at home. This conversation serves as a powerful reminder of the importance of being emotionally present.

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ANECDOTE

Success Without Family Alignment

Ryan Deiss realized he was using family as an excuse to work more, driven by ego rather than their benefit.
His wife confronted him, shattering the illusion that his hard work was truly for the family.

ANECDOTE

Divorced Parents But Unbroken Love

Ryan grew up with divorced parents who prioritized love and proximity without negativity.
Despite a "broken home," he never doubted he was loved and formed a unique perspective on family.

ANECDOTE

Infomercials Shaped His Genius

Ryan's early mornings watching infomercials sparked a lifelong passion for marketing and persuasion.
This foundation led him to embrace leadership and communication beyond just business.

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You can build the house, pay the bills, protect and provide—but if your wife doesn’t feel seen, and your kids don’t feel known, what are you really building?

In this episode, Ryan Deiss opens up about the moment his marriage hit a wall… and the quiet heartbreak of realizing he had drifted from the people he loved most.

It wasn’t burnout. It wasn’t failure. It was success without alignment—and the cost of being emotionally absent, even while physically present.

You’ll take away:

What his wife said that shattered the illusion he was “doing it for the family”
How disconnection with his kids crept in while he was busy being “responsible”
The family-first calendar ritual that rebuilt trust and rhythm at home
Why saying “yes” to golf with his son—and missing a deadline—was a turning point
The question he asked his son before college—and the answer that brought him to tears
Why presence—not perfection—is what restores closeness in marriage and fatherhood

If you're trying to be more than just the guy who gets stuff done…If you want to be the man your wife trusts and your kids remember—

👉 Listen to the full episode now

You don’t need to do more. You need to show up better—for her, for them, for you.

______________________________________________________

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