BTU #290 - We Study Billionaires (Preston Pysh)

When I was first starting out, there were some very early mornings. That went on for years. There was a lot of consistent, hard work that went into it. You have to keep taking small, consistent bites until you get where you want to go.
— Preston Pysh

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Why Listen:

It was such an honor to connect with Preston, who runs the #1 Investing Podcast, We Study Billionairs, which has over 1 million downloads per month. In addition to that, he is ranked on Amazon in the top 35 Business Authors. Both of these are impressive enough on their own, but what really kicks this to the next level is the fact that Preston does all of this while serving on Active Duty in the military, as well as being a present parent of four kids. First of all - my apologies to both Preston and listeners, because I had some technical difficulties with this interview. Fortunately, Preston is always prepared, and had a backup recording of our interview, as my recording software crashed for the first time in 280 episodes during Preston’s interview. However, that recording did not have my audio, so I had to re-record this. So, bear with me if the audio quality of this episode is not as good as other episodes, but I assure you the content is absolutely top notch. Preston is humble and authentic in his advice, and I believe - regardless of your intended career path - you will benefit from listening to this episode.

About Preston:

Preston is the founder of The Pylon Holding company, which conservatively grows equity through the acquisition of private or public companies. He runs the #1 Investing Podcast, The Investor’s Podcast, with over 1 Million downloads per month. He a best selling author and ranked by Amazon in the top 35 Business Authors. He started out at West Point, served in the Army for over seven years. He holds an MBA from the Johns Hopkins University and has been accepted to pursue a Master of Computer and Information Technology at the University of Pennsylvania.

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Selected Resources: 

Transcript & Time Stamps:


Joining me today is Preston Pysh. Preston is the founder of The Pylon Holding company, which conservatively grows equity through the acquisition of private or public companies. He runs the #1 Investing Podcast, The Investors Podcast, with over 1 Million downloads per month. He a best selling author and ranked by Amazon in the top 35 Business Authors. He started out at West Point, served in the Army for over seven years. He holds an MBA from the Johns Hopkins University and has been accepted to pursue a Master of Computer and Information Technology at the University of Pennsylvania.


How would you explain what you do for a living?

To me, it’s about doing things that I thoroughly enjoy. I love engineering, finance and math. So wherever those lead me is what I end up doing. 


It’s amazing that you’ve managed to align what you do with your natural interests and skills. 

Especially with my podcast, it ended up being a lot of luck. I was doing it more for myself and wanted to learn. It turned out that there were a lot of listeners interested in the same thing. It really turned out to be a lot of luck helping me out. 


Did you start the podcast while on active duty or after you had gotten out?

I’m still active duty in the military. So I kind of do two things at once. I do my military duty during the day and the podcast at night. I love serving but in the evenings I go into business mode and work on my podcast or my YouTube channel. 


How do you juggle all of those priorities?

I think a lot of people totally overestimate what they can do in one year but they underestimate what they can do in ten years. The thing that I take pride in that I make my family a priority. I don’t work on my business when my kids are awake. But when they’re sleeping, I take advantage of that time. 

When I started my business, I obviously had to do everything. But then once you start growing, you can hire people that help you reach your goals and objectives. I’m able to be successful because of the team I’ve surrounded myself with. 


What advice do you have for someone that has a desire to write a book?

When I was at West Point, my Achilles’ heel was English and Writing. It wasn’t something I practice or was good at. But in my junior year, there was a writing test that you had to pass. If you didn’t pass, you got throw out. You got two tries. I failed my first test but passed the second. 

Later I was in Afghanistan serving with the Army. I was a pilot in a division staff. We were 12 hours on duty, 12 hours off duty. During that off duty time, I decided to capture different leadership lessons I learned at West Point. I wanted to put all those stories together in a book. I knew that I was bad at writing so I wanted to improve. I started nibbling away at it by writing one funny story from West Point and then having someone else read it and provide feedback. That turned into a constant off duty activity for me and eventually I was able to put those stories together in a book. 


How did you start the Investors Podcast?

I loved investing and finance. I was an aerospace engineering major at West Point and I’ve always been passionate about math. Later on, I became interested in applying those math skills to investing. 

At that time, Warren Buffett was the wealthiest man in the world. I started looking at what books he reads and who his mentors are. I started to consume those resources until I felt like I had a better understanding of that world. One of Warren Buffet’s favorite books is Security Analysis. It’s very difficult to understand this book if you don’t have a background in finance. So I started digging into other things so that I could understand what was written in Security Analysis. I ended up writing a summary book to help other people get through the book Security Analysis in a way that would make sense to them. 

But again there was a lot of luck involved. This was at the very beginning of digital books - about 8 or 9 years ago. At the same time, YouTube was a new thing. I knew a little bit about HTML and programming. So I decided to record some YouTube videos to complement what was in my summary book. Both the book and then YouTube video ended up being very successful. 


How did you find your co-founder?

I went to the Berkshire Hathaway shareholder meeting in Omaha, Nebraska. The people that go to that meeting are extremely unique. After the meeting, I was standing in the airport heading home. I saw a guy wearing a LinkedIn jacket. We started chatting and he was asking me if I had heard about podcasts. I hadn’t but he recommended a particular podcast to me. When I got home, I downloaded all the podcasts and started listening to them. To me it was similar to my YouTube videos but more conversational. I loved the idea of podcasts. 

A short time later, I ran into Stig in an online forum. I asked him if he would be willing to help me finish a book I was writing on accounting. He did and we ended up building a strong friendship. We ended up co-founding The Investors Podcast together. 

There’s no way over the past 10 years that I would have had to accomplish what I have without allowing other people to help me along the way. If you’re a giver and the people you work with are takers, those relationships won’t last because in the end, the giving side recognizes that the relationship isn’t equal. 

If you’re looking for a co-founder for a new business idea, a lot of it is luck but it’s also important to find a giver rather than a taker. 


How have you grown the audience of We Study Billionaires?

Stig and I are relentless with the editing of our show. We want to make sure the show is concise and rich with information. A 10 minute podcast with great information is far better than an hour long podcast with a lot of meaningless talking. 

We mostly edit ourselves rather than what the guest is saying. We want to highlight our guests and the nuggets they have to share. 

If you do a podcast, it’s also very important to know your audience. You also should be familiar with who the top performers are in your particular space. The barrier to entry in the podcast world is very low but in order to differentiate yourself, you really need to provide a quality product. 

Understanding search engine optimization is also important because it can help drive traffic past your podcast.


What are the trends you’ve seen with the people you’ve interviewed on We Study Billionaires?

Tony Robbins got his foundation from Jim Rohn. Tony is all about focusing on your destination. He uses this analogy - imagine that you’re on a sailboat and you want to go somewhere. But the only way you’ll get there is if you figure out where you want to go. After you do that, you need to have a positive attitude. If you’re on your sailboat and you want to go north but the wind is blowing in your face you can’t just give up. It is possible to sail into the wind but you have to be open to the idea of finding that solution.

We also had Jesse Itzler on our show. He wrote a book called Living With a SEAL. He invited me to go on a hike with him. During the hike I told Jesse, ‘You really have to love what you do.’ He told me ‘No, fuck that. You have to love the journey and the struggle.’ 


Why have you continued to serve on active duty?

I’m so grateful for the opportunities I’ve been given and the experiences I’ve had. I want to do whatever I can to protect the freedoms that are available in this country. We live in a country in which we can question what we think to be true and discuss big ideas with one another. 


What advice would you give people serving on active duty that want to pursue a job or side hustle?

There’s nothing more important to me than my job. It’s my top priority. So I would advisable people to take on side hustles that they can control timewise. That way they can move that around if something military related comes up. It’s important that your military role remains your top priority. 


Do you have any book or podcast recommendations?

Three books that I recommend are The Power of Habit, Influence, and How to Win Friends and Influence People


Is there anything else you’d like to share with listeners?

The thing I’ve learned from interviewing all these highly successful people is that they are focused on exactly what they want. But they are often very unbalanced. They completely sacrifice their family, friends or other interests to become successful. 

I would advise people to set the destination for what you want. But also think about what you are sacrificing and make sure you are willing to make that sacrifice.