AI Personal Finance Is More Personal Than You Think artwork

AI Personal Finance Is More Personal Than You Think

Money Tree Investing

September 4, 2026

Bill Harris discusses the rapidly evolving role of AI personal finance, sharing his experience building companies including Intuit, PayPal, Personal Capital, and his own Evergreen Wealth.
Speakers: Kirk Chisholm, Bill Harris, Phil Weiss

Topics: Investing, Business

**SPEAKER_1** (0:01)
Welcome to the Money Tree Investing Podcast. Stock market, wealth, personal finance, value stocks. Invest in your life.

**Kirk Chisholm** (0:11)
Hello, Smart Money Tree Podcast listeners. Welcome to this week's show. My name is Kirk Chisholm. I'll be your host. And today I'm joined with Bill Harris. Hey Bill, how you doing?

**Bill Harris** (0:18)
Hey Kirk, how are you?

**Kirk Chisholm** (0:20)
Doing great. So for those of you who don't know Bill, maybe you can tell us a bit about yourself and your background.

**Bill Harris** (0:25)
I've been in the financial technology business now for 30 years.
It's disappointing to think about that, just the longevity. But nevertheless, I've seen a whole lot, everything from early time sharing to MS-DOS, to graphical interfaces, to the Internet, to mobile, to now AI. And what I've had the opportunity to do is be on the leading edge of each of those new technologies in terms of how you apply that to use that in the financial technology in a way that can make people's lives better. That's what drives me.
Just a little bit about what I've done. I've had a number of successes. People say, what's the secret to success? Get old. Because the older you get, the more at-bats you have. And particularly in the tech business, you got to be in the right place with the right idea at the right time. And I mostly start businesses, and so some of them don't work. But anyway, I moved from media to technology first at TurboTax.
And I ran TurboTax for a number of years. Then I took that company public, then we merged it with Intuit, and then I ran Intuit.
And at about the height of the internet, left Intuit and joined Elon Musk and Peter Thiel and Reid Hoffman. And we started PayPal, or what's eventually called PayPal. That was sold to eBay. And since that time, I've been starting companies, Personal Capital, which was an RAA, the first high-end RAA that was effectively digital. And we went from zero to 23 billion. And then I've started a number of companies, portfolio management company, or portfolio management software company. Started a neobank called One, which Walmart purchased, and it's now the Walmart cash card.
And then more recently, I'm working on a thing called Evergreen Wealth.

**Kirk Chisholm** (2:21)
You've certainly seen it all. MS-DOS, huh?
Good old days.

**Bill Harris** (2:25)
Oh, man. You know, it started when modems were 128-bit, and when you had about 128K of memory in a machine.

**Kirk Chisholm** (2:36)
I remember those days. Those were the days of like the movie War Games, where you had the dial-up modem with the weird sounds like that.
Yeah, I can't even mimic the sound. It was so awful. But yeah, those are the days. Technology has come a long way, I would argue, in finance. Probably it's a lot slower than in other areas. But what are some of the biggest trends you're seeing now in technology and finance?

**Bill Harris** (3:02)
It's all AI. I'm not a believer that AI is completely different and changes the world and all that kind of stuff. I mean, it's gonna have a huge impact, but it's not qualitatively unlike some of the other things we did. Going to the internet was huge. Mobile was very significant. And this thing is really going to make a huge change. And here's the thing I'll say about finance and technology. Yes, it moves slowly, but you've got to look at the sector of the business. If you've got big financial companies, I don't care whether it's Bank of America or Schwab or whomever, there's just so much technology, so much process, so much history and paradigm, that of course they move slow.
But if you look at the edges, and it's typically been the fintech companies, if you look at the edges, it goes pretty damn fast.
The opportunity is to get out there in front and think about how to apply the new technologies to the very simple thing of people want to understand their money, maximize their money, and probably more important than anything else, feel good about their money.

**Kirk Chisholm** (4:13)
Let's talk a little bit about AI because everyone's talking about AI and it's an interesting interesting aspect technology right now because I think there's a lot that's unknown, there's a lot of speculation and frankly, it's in some ways hard to predict where the future is going to be. Where are people applying AI to finance right now that you're seeing is most effective?

**Bill Harris** (4:33)
You know, first of all, I just make the quick comment, artificial intelligence makes a whole lot of sense, but it's not necessary, I mean, I've done pretty well with natural stupidity.

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