🎙️ Staying Curious

[5 minutes to read] Plus: Getting to know TIP's Patrick Donley

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Weekend edition

Here’s yet another example of AI's benefit: A high schooler has created an algorithm that accurately predicts the needs of 911 callers.

With a 94.5% success rate, it could reduce response times and save cities millions.

“If the algorithm says, ‘I think it’s a mental health call,’ then you can send a psychiatrist or a mental health professional with the EMS crew to assist the patient and provide the more appropriate care” — instead of simply rushing police to the scene, the high schooler said.

Today, we're chatting with our very own Patrick Donley, a host of Millenial Investing.

All this, and more, in just 5 minutes to read.

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Patrick Donley on Learning and Real Estate

TIP’s Patrick Donley (right) with fellow host Kyle Grieve

Building wealth and independence

Meet Patrick Donley, a real estate entrepreneur, investor, and host of the Millennial Investing podcast for The Investor’s Podcast Network, the world’s largest stock investing podcast company.

Over the past year, Patrick has interviewed dozens of business owners, authors, and entrepreneurs. Each interview covers diverse ambitions, unique backgrounds, and compelling journeys. Yet one unmistakable conclusion has crystallized for him.

“Many of the people I’ve interviewed aren’t necessarily smarter, but they think much bigger about what’s possible in life,” Patrick says. “Most people are held back by limiting beliefs, and the folks who have done really well have smashed through their limiting beliefs.”

The founder and managing director of The Wexford Group, a real estate redevelopment company based in Columbus, Ohio, Patrick has lived and worked abroad. He has had a wide variety of adventures, including studying economics in Luxembourg, writing for a business newspaper in Vietnam, attempting to learn Spanish in Columbia, and biking across America to raise money for Habitat for Humanity.

He’s deeply curious and loves learning about financial markets and entrepreneurship. He can usually be found listening to podcasts, enjoying his family and friends, or attempting to hone his golf game in his free time.

Our full interview with Patrick was edited lightly for brevity and clarity.

Tell readers about your road to being fascinated with the investing world.

I loved collecting baseball cards and traded with the neighborhood kids. I also had side hustles like mowing lawns and even a chocolate chip cookie business. But, in 5th grade, my teacher, Mr. Lemon, gave a talk on the stock market and I fell in love with stocks and wanted to learn all I could. I read How to Buy Stocks by Louis Engel and still have the tattered paperback in my library today.

I had my dad open a custodial account, purchased 100 shares of Bob Evans at $3, and sold it at $6. My next investment also doubled, so I kind of got hooked on investing at a young age. 

What is your favorite part of running MI? 

One of my strengths from the Clifton StrengthFinder is “Learning” and I get to continually research and learn from some of the smartest, most successful people in the investment, real estate, and entrepreneurial worlds. I love doing the research for each interview and I’ve enjoyed the opportunity to be a podcast host. I probably would have done it for free! 

What are some of your favorite interviews?

I’ve always had a philosophical/spiritual side and have explored the world’s wisdom traditions. William Green, who wrote Richer, Wiser, Happier, suggested I go deep in the tradition I was raised in, which was Christianity. So, I’ve really enjoyed having people who are unafraid to express their faith on the podcast.

My first was John Marsh, who has an incredible story of being a drug addict, massively in debt, and a failing marriage and was ready to commit suicide. He had a transformative experience, which he discusses in our episode, and became a believer. He has since gone on to transform not only his own town of Opelika, Alabama but also replicate what he’s done in several small towns across America.

The guy inspires me. He mentors Chris Powers of The Fort podcast and Brent Beshore of Permanent Equity. I’ve had Chris and Brent on the podcast and loved hearing about their journeys to faith and how it has transformed their lives. 

What are a few of your favorite books? 

I love William Green’s book Richer, Wiser, Happier and have re-read it several times. I’m also a huge fan of Morgan Housel's The Psychology of Money. I have been doing a deep dive into the Bible and trying to read from it every day.

Who are your investing role models, if you have any? 

I love continual learners, so I’m a fan of people like Buffett and Munger and investors like Guy Spier and Mohnish Pabrai. I also love cranky contrarians and was influenced quite a bit by Jim Rogers, David Dreman, and Doug Casey. 

What is your investing motto, if you have one? 

Buy $1 of assets at a 30-50% discount. 

How much prep goes into an interview? 

Quite a bit. I do a lot of research on each guest before an interview and listen to several interviews they’ve done. I spend a lot of time on their Twitter feeds to understand them better, and then several hours are spent on coming up with questions that I send to them in PDF format so they can prepare for the interview. 

A few of your favorite stories from the show? 

A grade school friend of mine who had recently retired and had become CFO of a Fortune 500 firm listened to an episode I did on cost segregation. He was bored with retirement and called me and said, “What do you think about starting a cost segregation company?”

I said I thought it would be a great idea and didn’t give it much more thought. But he found a close friend who is an engineer, and the three of us launched a cost segregation company about a year ago, and it’s going really well. 

What do you hope the audience derives from your work? 

I hope people are inspired by what’s possible. There are so many ways to make money today and so many opportunities. All the playbooks are out there, and it just takes some willingness to pick a strategy, stick with it, and clone what successful people have already done. 

Can you give us a high-level overview of how you personally invest?

I have been a real estate investor and like the control it provides me over my portfolio. While I love the stock market, most of my assets are in real estate and bitcoin.

General thoughts on bitcoin and its role in your portfolio? 

Thanks to Preston and many others, I am highly convinced about Bitcoin. I’m excited about the next 12-18 months of this cycle. 

What’s the biggest investing mistake you made? 

I bought Amazon at $12/share back in the dot-com crash and said I would sell it once I had a 30% return. It hit $16, and I sold the position and never got back in. I’ve been afraid to calculate what it would be worth today had I held for the long term. That would be my biggest advice: buy quality and hold for the long term. Let compounding work its magic. 

Do you check on daily financial news? How do you block out all the noise on X, in the news, and elsewhere to keep a clear mind? 

I honestly don’t follow the daily financial news much. I’ll read We Study Markets and scroll Twitter daily (mostly to find new guests), but the news is often just noise. I have a long-term perspective on my portfolio and intend to just buy and hold. 

At what point do you sell stocks, if ever? 

I tried day trading when it became possible in early 2000. I love trading, the stimulation, and the game of it all, but it was a waste of time. I would have been better off simply buying good stocks, holding them forever, and using my time more productively elsewhere. 

How much cash do you like to hold, if any? 

Just enough for monthly expenses. My savings vehicle is bitcoin. 

How often do you check your brokerage account? 

Once a quarter. 

Do you think you’ll ever retire, or just keep studying the best and reading and sharing that information? 

I don’t think I’ll ever retire. I may take mini-retirements and travel for several months with my wife, but we both want to be productive and enjoy working on different projects. I’ll likely always do real estate projects of some sort. 

What are your favorite hobbies outside of investing? 

Working out. Golf and pickleball are two favorites. I also love to read and hike.

Is there anything else you’d like to share about your journey at TIP?

TIP has been an amazing place to work. Stig really optimizes for everyone’s happiness which is a very unique way to run a company. I’ve learned so much and have great co-workers, although it’s weird I’ve never met any of them in person. 

What has been the most rewarding part of hosting your podcast? 

I would say really getting to know the guests well and learning from them. Hopefully, the listeners benefit from their knowledge as well! 

Can you share a memorable interaction or story with a listener that impacted you?

I recently worked with Unchained Capital to set up a multi-sig account, and the guy helping me get everything set up recognized me from the podcast and said he had listened to several episodes and was a fan. Stuff like that is cool when it happens.

Dive deeper

Follow Patrick on X (formerly Twitter) and listen to his latest podcast episode here, which discusses how a couple dug themselves out of debt to build a $1.3 million real estate portfolio.

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