
David Osborn
David Osborn is a serial entrepreneur, co-founder of GoBundance, and Co-Founder & Chairman of Waterloo Associates, a single-family real estate private equity firm based in Austin, Texas. He is a WSJ best-selling author of Wealth Can't Wait and Tribe of Millionaires.
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Aug 25, 2026
You're the Bow, Not the Arrow: How He Sees His Job as a Dad
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David OsbornGUEST
And then it's college, and then she's gone, right? So, um, my goal with my family is to love them hard, make sure that I'm doing everything I can to keep them engaged in something that they're purposeful and passionate about, um, make sure they have a charitable reason, and then, you know, love my wife hard.

David OsbornGUEST
I don't, I don't know about you, but I find the loving of the wife is the hardest part.
The $200M Blueprint: David Osborn on Wealth, Mindset & GoBundance
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42:35

PJ CrescenzoHOST
If I'm a high-powered entrepreneur today and I say, I just need to do a better job with the frequency or the quality of my goals, what do I need to learn from David Osborne about this practice?

David OsbornGUEST
So you have this beautiful potential in life because we are divine beings and we have this divine spark within us.

David OsbornGUEST
And we get to co-create with the universe, if you believe what I believe, a bright and shiny future.

David OsbornGUEST
And the way you do that is considering what you'd like to bring forth in the world, what your area of service is, what you would like to do, what you'd like to contribute, and then designing sort of a flight plan for that.

David OsbornGUEST
When a pilot gets into a plane, they don't just sort of go, oh, I'm going to go from Austin to New York.
20 MINS LATER

PJ CrescenzoHOST
Was the email the greatest tactical step you took on leveraging your time? Or was there something else that you would say created the most bandwidth for you and your business and your life once you implemented it?
Why Not Me? Building Lasting Wealth, Freedom, and Vision with David Osborn
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4:22MatthiasHOST
Um, tell us about how you were, uh, 26, broke and starting over, and what was a single belief or decision that shifted your trajectory? How do you still instill that same belief in the brokers and investors you work with today?

David OsbornGUEST
You know, we're full of anxieties, we're full of critical s- thoughts, you know, like...

David OsbornGUEST
And for me, after selling for three years, uh, my mom had opened a brokerage up in Dallas, a couple of them actually, and they weren't doing very well.
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30:52MatthiasHOST
Wow