The Jeff Heilman Project (Podcast)
Jul 17, 2026 · 30 min · 11 segments
In this podcast, Jeff and Jessica talk about agitation and struggle, and how it fuels us to create and innovate. They pull from examples like CS. Lewis, Thomas Edison, George Washington, and Elon Musk…
Jeff HeilmanHost
Jessica HeilmanHost
So coming up on 25 years now, a guy named John Asher, who's a buddy of mine, lived in South Carolina for 20 years.
He had homes in New York and Pennsylvania and divested himself of those things in his mid-30s because his wife had family in South Carolina and they wanted to move south.
And John and I were involved in a couple of different business ventures over the years together.
And great guy, built a very successful real estate business, has investment funds on top of that, like public funds that are available for investment by business.
And I asked him one day because he's, you know, I've made not, not quite 10 million.
And I, I asked him, I said, um, what do you, what do you spend most of your time doing? And he said, um, uh, he said, I don't really talk about this, this that much.
And, um, we're, we're very clear on our, on our thoughts of worshiping and not, and steering clear of idol of idol worship.
Um, And he said, I spend between six to eight hours a day architecting my life and what I want to do.
The color and the size and the location on the hull of the pinstriping for his sailboat that he wants and where he's going to put it and He's not into cars as much anymore.
He's traded in all the fancy cars and just drives – I think he drives a Prius or something economical because he just doesn't care about those things.
But there are things that he does care about, trips that he wants to go on, houses he wants to build, businesses he wants to build with his children, those types of things.
And he literally architects and thinks and – dreams and schemes and plans and allocates capital and effort and energy and resources and talent and recruiting all this stuff toward building this ideal life.
So coming up on 25 years now, a guy named John Asher, who's a buddy of mine, lived in South Carolina for 20 years.
He had homes in New York and Pennsylvania and divested himself of those things in his mid-30s because his wife had family in South Carolina and they wanted to move south.
And John and I were involved in a couple of different business ventures over the years together.
And great guy, built a very successful real estate business, has investment funds on top of that, like public funds that are available for investment by business.
And I asked him one day because he's, you know, I've made not, not quite 10 million.
And I, I asked him, I said, um, what do you, what do you spend most of your time doing? And he said, um, uh, he said, I don't really talk about this, this that much.
And, um, we're, we're very clear on our, on our thoughts of worshiping and not, and steering clear of idol of idol worship.
Um, And he said, I spend between six to eight hours a day architecting my life and what I want to do.
The color and the size and the location on the hull of the pinstriping for his sailboat that he wants and where he's going to put it and He's not into cars as much anymore.
He's traded in all the fancy cars and just drives – I think he drives a Prius or something economical because he just doesn't care about those things.
But there are things that he does care about, trips that he wants to go on, houses he wants to build, businesses he wants to build with his children, those types of things.
And he literally architects and thinks and – dreams and schemes and plans and allocates capital and effort and energy and resources and talent and recruiting all this stuff toward building this ideal life.
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