A Conversation with Jonathan Lansky

This month, we caught up with Jonathan Lansky, a passionate investor with a wealth of experience in the financial realm. Author of his own blog, No Straight Lines Investments, Jonathan's journey in the investment landscape has been marked by valuable lessons and a commitment to transparency. He's a firm believer that true investment stories go beyond successes, embracing the challenges and growth that come with them. His blend of investment expertise and approachable demeanor makes him a unique and insightful voice in the world of finance.

Can you share a little bit about your investment journey? What sparked your interest in the stock market and how did you develop a passion for investing?

My initial investment venture was a disaster. I made a rookie mistake by investing in a popular Japanese mutual fund following my dad’s recommendation without fully understanding the market. Unfortunately, I got in just as the Nikkei was peaking, but it took nearly 30 years to recover from the loss. It was a very good first lesson about understanding what you're doing and why you're doing it.

Next, I started a lawn care business. After I sold it to my business partner, I used the proceeds to invest in another mutual fund which did really well. In 1996, I became an investment banker and did that for about 18 months, which was a great learning experience, but it wasn't for me. I then took an equity sales position and fell in love with stock investing. For about a decade, I focused on sales, until I joined forces with an exceptional Canadian investor I had known from my early days. We had co-managed an internal fund for 12 years before parting ways in 2018. Since then, I've been investing my own money, offering my expertise to companies, particularly in the capital markets and on strategic endeavors.

How has your approach to managing your own money in the past few years differed from your previous roles in an institutional setting. Are there challenges?

I'd say the biggest challenge is the absence of information flow from the Street. In my previous role, I had access to a wider variety of research and data simply because our commission pool enabled it. However, I've observed that information accessibility has improved over the past five years, making it easier for anyone to access analyst research and similar resources. Despite this, there's still a challenge, particularly in getting insights from salespeople and traders. This lack of direct contact sometimes leaves me feeling unplugged.

On the plus side, I am completely away from the noise and the bias. My experience working from home before it became common has given me the freedom to focus without the stigma of remote work. In the investment realm, sometimes it's beneficial to be away from the crowd. Striking this balance is key.

One of the great things about investing is, you're constantly being fed heaps of humble pie. You're constantly learning. It's never the same day twice. What applied previously doesn't necessarily work now.

Tell me about No Straight Lines Investments. Do you get a lot of dialogue and positive feedback about what you post?

I don't write controversial things, I'm a bottom-up stock picker. I get some feedback, and the overall reception has been good. When I was in sales, I used to organize a stock picking contest. The idea was to gather fresh perspectives and some good competitive fun. Participants selected both a long and a short pick, with a year-hold requirement.

Investing is unique in the sense that you can sound incredibly smart, yet the real measure is your results. It's always been my belief that if someone only boasts about their successes, they're either being dishonest or aren't truly invested in the field. I've had the privilege of sitting alongside a tremendously successful investor for 12 years. However, even he admitted to me in a conversation about a year after the pandemic hit, that he had been shockingly unprepared for such an event. It took him a considerable amount of time to recover from that setback. This revelation was particularly interesting because, despite his success, the nature of this business has a way of humbling even the best.

The best investors readily admit their missteps. Look at figures like Howard Marks, Warren Buffett, or Cathy Wood. They openly share their insights, acknowledging their ups and downs. Cathy Wood, for example, despite facing public setbacks, sticks to her guns. Whether you agree with her or not, her commitment is respectable. The investment landscape is filled with frustrating and humbling moments, yet it's undeniably engrossing.

What sets this industry apart is its dynamic nature. I get up every day with no idea what's coming out. The blog has truthfully reignited my passion.

Has writing always been a big part of your life?

When I started managing money, I used to share ideas with a group of like-minded people. It wasn't formal: an email blast to around 100-150 people. I really enjoyed that because it instilled this discipline of writing. It's not like anybody's holding me accountable. I hold myself accountable. But it's out there in print, so you want to put your best foot forward. I take pride in what I do; I don't want to look foolish. Ultimately, I want to monetize it. Although I haven't reached that point yet. My original intention was to write consistently for about a year, hoping to attract an audience and become a part of their everyday routine.

Beyond investing, what other hobbies or interests do you pursue to find balance and enrichment in your life?

First and foremost, I'm a husband and a dad. I try to structure my life in a way that allows me to be involved in the lives of my kids. A variety of activities help me maintain a healthy lifestyle. I love hitting the trails on my mountain bike, carving down ski slopes, and getting on the basketball court. Staying healthy is a priority. I'm a voracious reader. My reading list spans beyond just work-related material. I'm particularly drawn to biographies of intriguing individuals from diverse backgrounds. Exploring the life stories of people from different walks of life fascinates me. However, I'm equally drawn to fiction, especially classic literature. There's a reason these books have stood the test of time.

Any recommendations?

There are a couple of nonfiction books that, to me, are brilliant. One is called, "Living with a Seal" by Jesse Itzler. Don't be misled by the title; it's not what you might expect. This book is an absolute delight, both hilarious and incredibly insightful. Another standout is "Shoe Dog," by the Nike founder, Phil Knight. This book surprised me in the best way. Prior to reading it, my perception of Knight was quite different from the person he revealed himself to be in his writing. "Shoe Dog" is, without a doubt, among the top three nonfiction works I've ever had the pleasure of reading.

You know what else? I love movies. I'm very blessed because my wife and I have the same taste in movies, so there are no conflicts. We like silly slapstick. It genuinely baffles me that comedy doesn't have its own category at the Oscars. I firmly believe that crafting comedy is more challenging than working on dramas.

This inclination towards humor extends to my investment journey as well. While there's a necessity for a serious approach in the investment world, I appreciate the balance that humor brings. Amid the seriousness, it's refreshing to embrace laughter. After all, why take yourself so seriously?

When you're writing, it's important not to come across as condescending or give the impression that you're infallible. People connect more with relatable content. For me, it's not a put on; it’s who I am. I write the way I speak. I'm not trying to be something I'm not. That would be hard work.