This week I recorded the 11th episode of Think Like an Owner and as such the podcast was at the front of my mind. Each time I prepare for a podcast, I think about what topics I want to cover and how I want to ask them. For my first episode or two, I would write out on a sheet of paper specific questions I wanted to ask the guest. Pretty quickly I realized that this made conversations feel more structured and less natural and fluid and decided to think about questions less and topics more. When I record episodes today, I don’t have any specific questions prepared in advance. I’ve found the best and most interesting conversations come from asking the guest about what interests them the most in business and private company investing and just letting them go.

The only questions I do prepare are the closing questions which are: 1) What class would you want to teach in college? 2) What is the most fortunate event to have happened to you that was by chance? 3) What is the best business you’ve come across?

When I ask question #3, what’s the best business you’ve seen, a lot of the time the response is “best business based on what?” I try to avoid giving any idea of what the “best business” looks like to me, because each person has a different definition of that and I want to learn about how the guest defines “best.” Andy Ellis from Localize Capital for instance talked about Bryan Materials Group which makes concrete and other construction materials. He thought it was the best because of its 135 year history and the fact it was family owned in the fifth generation. Mike Boyd from Mudbrick Capital talked about Envato which is a marketplace for website themes, which he thought was the best because of its highly profitable and scalable model. Each person had a different reason for choosing the business they did, and that’s what’s so fun about that question.

The first one tells me about what they believe is not being said in education and the way we teach business. None of the answers so far have been anything like the classes I took in college and I wish some of them had been around. Guests have said a class on Charlie Munger, the anti-entrepreneurship class, how to have difficult conversations, among others. This is a question I really enjoy hearing someone’s answer to.

The second question gives me pause though, I’m not convinced it’s the best question I could be asking. The point of asking for the most fortunate event to have happened to someone that was random is to ask them about what they felt was luck rather than skill in their success. I think we can all agree that luck plays a big part of our lives, but that’s not something we can use or apply ourselves. There aren’t many lessons to be drawn from hearing about someone’s luck, beyond understanding their humility.

Patrick O’Shaughnessy asks every guest what the kindest thing someone has ever done for them was, and I think that is a phenomenal question that better gets at the heart of what I’m trying to ascertain from my question. There is some element of their success that wasn’t due to their own efforts or intelligence, but rather the luck, kindness from another, or just being at the right place at the right time. I think I need a better question than the one I’ve been asking, and maybe that’s taking Patrick’s question as is. (It feels like plagiarism to outright copy his question, but maybe it is simply the best way to ask about that extra element of their success.) I’d love to know what you as the reader think and feel free to hit reply to this email and share your thoughts and ideas with me. I’m always open to a discussion and refining the project and hearing new ideas.

Capital Notes

Chenmark: People Like Us Do Things Like This, Part 2

“So, what is Chenmark? We are a team of small businesses committed to each other and to the constant pursuit of better. We share a commitment to Chasing Better, Keeping Score, Playing the Long Game, and Putting the Team First.

We enjoy working through the constantly varied mix of challenges associated with running any smaller company. We balance a commitment to long-term value creation with the daily drive needed to make decisions despite incomplete information. We maintain a passion for business, significant competitive drive, a willingness to grind, and above all, a deep desire to have a tangible impact on employees, customers, and the community at large.”

Ankur Warikoo’s Twitter Thread: Thoughts on Turning 39

“Nothing pisses the world off more than you being comfortable with who you are.”

“To not have a plan and be ok with it, is the best plan. It will take everything to get to that point.”

“Resisting the obvious is a great way to change your orbit. If you do what everyone else will do, you will end up as everyone else.”

Little Engine Ventures: Marketable Securities in a Private Company

“If you believe in buying assets for less than they are worth, doing the work, or employing the managers to oversee your interests, I highly recommend you consider marketable securities in your private company. You do not need to hold gobs of names. You do not need to allocate hours of time. You could buy the index or even pick five names you like and buy them equally. Do not create excess work for yourself just to heed my advice. I am no advisor. I am a practitioner.”

If you found an interesting article, podcast, or interview that I missed, please let me know, I’m always looking for interesting stuff!