Nov 21, 2023

141: Winning at Organic Growth with Shawn O’Malley at “We Study Markets”

Succession Stories host Laurie Barkman, The Business Transition Sherpa™, welcomes Shawn O’Malley, Chief Editor and Financial Writer for “We Study Markets” at The Investor’s Podcast Network. 

“We Study Markets” financial newsletter has quickly gained traction with 36,000 daily readers at the time of this recording.

The essence of this episode is about organic growth and intrapreneurship – building a new business within an existing enterprise. Shawn is working at the intersection of unmet market potential and Gen Z creativity. 

Listen in as Laurie and Shawn discuss the challenges of building a startup within an established company; the power of trust; learning from failures; and how curiosity fosters continuous learning.

“When you’re young…it’s okay to fail and make a lot of mistakes. As Ray Dalio said, “Pain plus reflection equals growth or progress.”

Shawn O’Malley, Succession Stories

Hear what’s motivating a Gen Z leader early in his career– something many companies strive to better understand for talent development.

Find Shawn O’Malley and “We Study Markets” Here: 

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Laurie Barkman
Sean O’Malley Welcome to Succession Stories.

Shawn O’Malley
Hey, Laurie, thanks for having me on.

Laurie Barkman
Why don’t we start with you? Tell me about you and how you got into what you’re doing.

Shawn O’Malley
I’m pretty young. I graduated in the class of 2021, I was studying Finance down at a small school in North Carolina called Elon University and I started on a very traditional boring finance path. I was working for a big company that’s not exactly on Wall Street, but sort of Wall Street adjacent, it doesn’t really matter. I was working with investment bankers and doing lots of very sexy, exciting stuff like that, and managing data and building Excel models.

I was doing the CFA Program, which is Chartered Financial Analysts and I passed level one, it’s like 300 hours of studying. So yeah, I was coming out of college very much, hoping to climb the ladder and build up a kind of name for myself in the finance and investing world. As we’ll talk about a bit more today, I found myself and the opportunity to jump ship and do something a bit more entrepreneurial and I really love it. I think deep down, I’m probably a risk taker. I also really love to write and so to some extent, what I do now is the intersection of all these things, finance and writing and taking some risks.

Laurie Barkman
I love it! That’s why I wanted you to come on because most of the folks listening, I don’t know, for sure, but dare I say, are probably north of 50 or they’re in their 40s and you are in your 20s. We’ve had one other guest on the show in his 20s and he’s the 10th generation of his family, so it’s a little bit different situation than yours. What I find interesting about your story, as we’re gonna tell a little bit more about it and the company that you’re with is that you’ve got a pretty interesting opportunity from a career standpoint. You’re gonna tell us, I’m sure, about how you’ve made this switch from Wall Street to kind of Wall Street adjacent, and building the business that you’re in now. Why don’t we jump to that? How did that come together?

Shawn O’Malley
As I was preparing for this classic finance career, and was doing all the things in school and mock interviews, and prepping very much to do what Wall Street does so well is make themselves rich and manage other people’s money while doing it. It was something that I found generally very stimulating, which is investing and understanding financial markets. While I was studying and working my way through school, I started looking for podcasts that I would listen to on the side that would really kind of scratch the itch of not just learning about the boring kind of standard economics and business management stuff that you learned in school, but I was really captivated by stock investing and kind of the big picture of what was going on in financial markets.

It was actually during the COVID lockdowns, I got sent home from school in March 2020 and was locked down with my parents in our house. I was looking for some opportunities to kind of escape and go for walks with my dog and also be productive and really use the pandemic as a learning opportunity. It suddenly became very clear to me that I had no idea how long this was going to go for and I should probably try to make the most of this time. I remember pulling up my phone and looking at Spotify and just typing in investing podcasts and I’ve found my current employer that way, just through sort of the algorithm and some luck there.

The name of our company is The Investors Podcast Software, and I started listening to the shows. I fell in love with the guests that they brought on every week, the constant learning, and really just their way of thinking about stock investing. I listened to the show for two years and flash forward. I listened to it, like I said, through my junior and senior years of college and then coming out of college. I’m working this corporate finance job. I’m studying for the CFA, and all of a sudden, on one of the weekly episodes of the podcast, I hear that there’s an opportunity to join the team and so I jumped on it.

I think I had literally just started my job, maybe two weeks prior. I get on and I talked to The Investors Podcast, CEO and co-founder and podcast host, Stig Brodersen, and he looks at me and he goes, Is there a reason why you’re applying for the job after you just started your first job at a college? It probably seemed like a red flag to him and in hindsight, I think it was a green flag because it was an indicator of just how passionate I was. So thankful for everything I had learned from this podcast company that I was willing to jump ship and abandon almost my entire kind of career and life plan as I had imagined it up until that moment for this opportunity.

It was funny enough, the opportunity was actually to be a YouTube host, which is not something I’m cut out for, I’m pretty introverted. I know nothing about editing and making videos, or anything like that but again, I was just so excited by the opportunity. Honestly, probably very naive and a little dumb, but I knew that I wanted to get my foot in the door.

It was also funny, too. I did that first interview and I was so used to getting prepped to do interviews for kind of Wall Street-style jobs, took myself very seriously, took the interview very seriously. 22 minutes into the call, Stig looks at me, and he goes, you’re like a robot, I had such high hopes for meeting you. I just feel like I don’t know who I’m talking to. I don’t know you at all and I’d like to think that’s not who I am. I think that I was nervous to meet him and nervous to do the interview. Basically, he gave me a second chance which I’m really fortunate that I had that because otherwise, I’d probably just be climbing the ladder right now at my corporate job.

We had a heart-to-heart conversation and we ended that first call. He said, I want to keep in touch. I don’t know if I’m going to hire you today to be the YouTube host at 22 right out of college but I do want to keep in touch. He did he followed up to two months later and he gave me an opportunity to sort of prove myself, I wrote a stock investing guide that got featured on the company’s website. I also was working on a stock investing blog that I was sort of writing personally. He read that and I think after seeing both of those samples, he mentioned that they were looking to build a newsletter business, which I’m sure we’ll talk about more today. That was ultimately what I was brought on to do.

Within a short period, I was working a corporate job, studying for the CFA, and trying to figure out what my route of Wallstreet would be and as I sort of think of it now I’m what you might call a recovering finance bro. I’ve gone from just thinking about how I could enrich myself and climb the ladder to now being in a position to educate other people about finance and be more humble about what I know and what I don’t know, which I do through the newsletter that we write.

Laurie Barkman
That’s fantastic. Thanks for sharing that background. Why don’t you tell me a little bit more about The Investor Podcast Network and the newsletter as a startup?

Shawn O’Malley
The Investors Podcast Network is the world’s largest stock investing company which sounds really impressive, and it is impressive, but it is also kind of a niche that we’ve that we’ve carved out and got her name in early. As I mentioned, Stig, and then his other co-host, Preston started the podcast together in 2014. It’s called the flagship show called We Study Billionaires and I think Steve would be the first one to tell you that, it was sort of a matter of luck that not a lot of people were even doing podcasting back then. There definitely weren’t many stock investing podcasts going on.

They found this sort of feedback loop where they got at the top of the charts and they just kept getting recommended by the algorithm. That kept accelerating and building on itself. Eight or nine years later, we have 140 million downloads. I say we as if I deserve any credit for that, which I don’t but during that time, they did some other stuff. I think they first started doing book reviews and so they would basically just ask for people’s email addresses and they would email them a written version of the book review that they had done on the podcast that week. They basically accrued a few 1000 email addresses over the year.

The years that they weren’t really do anything with and as I mentioned, I was brought on to start this newsletter business. What was sort of originally outlined to me was, hey, we have a lot of news, we have a lot of email subscribers. When you look at some of these other major newsletter publications like Axios, and Morning Brew, and which is really popular with my generation and with millennials.

I think they have like 5 million daily readers, which is just huge. We saw that as kind of a case study of hey, this can work. We have a large audience and we have a lot of credibility in the stock investing niche, we need to be tapping into the kind of daily newsletter business too so I was brought on to first write the newsletter and come up with what should the branding be? What should the tone be? What should the style be? How long should it be? Obviously, the goal is to do it daily and figure out you know, what was the right content, mix in-depth for our existing audience, and then also being mindful of we wanted to grow it into a multimillion-dollar business. What would the content have to look like, at a certain scale, for us to attract and retain a much broader audience? Those are some of the big-picture challenges that we’re still working through. Now I’ve taken a lot more responsibilities of actually managing the business and we have $100,000 advertising budget that we plan to execute on Meta through Facebook Ads and Instagram Ads, and other sorts of cross-promotional and growth opportunities.

I’m managing some of that stuff. Now, we also have a team of three or four of us who work directly and indirectly on the newsletter in one way or another, doing sales for writing it, and editing it on a daily basis. It’s been quite a journey over the past year and I’m always excited every day I wake up to see what’s next.

Laurie Barkman
Did you ever think that you would be a creative?

Shawn O’Malley
Some part of me always thought I had this romantic idea of being a writer. I was always into philosophy and I love the idea of being this reckless writer. But I also love the idea of working on Wall Street and being like a big finance, big wick, which is obviously quite a dichotomy. To some extent, I feel like I’ve been able to combine both of those fantasies and I feel really fortunate about it, where I get to, you know, it’s a financial markets newsletter. I kind of quite literally get paid to study financial markets and share what I learned with other people, which is creative and involves writing. It forces me to be very thoughtful, while also kind of making me feel at least like I’m plugged into the world of Wall Street.

Laurie Barkman
What’s the level of empowerment that you feel at this role? Because it’s a new role, right? There wasn’t anyone in your shoes, no one to follow? You’ve got mentors, maybe you don’t? How does that all work?

Shawn O’Malley
Iif I look back, it’s a recipe that doesn’t work for everyone. I’m not tooting my own horn but it did prove very motivating for me in the sense that I was given a lot of trust really early on. As soon as I joined the team, it was sort of seen as there was this extensive filtering process to get the job. I did three interviews with Stig. I did multiple sample writings proving that I kind of knew what I was talking about but once I got in the door, it was like, hey, anything you want to do whatever you think is best but let’s do it that way. I didn’t have to explain my decisions all that much. To some extent, there was just a lot of trust really early on to say, hey, let’s fail fast and it’s okay to fail. You’re really young, you’re gonna fail and make a lot of mistakes.

There’s this great quote from Ray Dalio, where it’s pain plus reflection equals growth or progress, one of those two words, but it means the same thing. The idea is, it’s okay to make mistakes as long as you’ve learned from them. If you don’t learn from them, it goes to waste. That was sort of something I heard very early on when I joined The Investors Podcast, and I’ll call it TIP, that’s just the acronym we use for short, early on a TIP was really just, it’s okay to make mistakes. You’re going to send an email out to 30,000 people every day, and you’ve never emailed more than four people before your entire life and that’s okay. We’re gonna do that together and you’re gonna make mistakes.

Stig has been a great mentor to me and then I had a couple other members of the team at TIP who were sort of helping along the way. At the end of the day, there was just a lot of trust given to really anyone who joined TIP. Once you make it through the door. you’ve kind of proven that you’re worthy of working there. It goes from being really skeptical to being Hey, you’re part of the team, all hands on deck, let’s get stepped on, let’s check off the boxes. It has really been a whirlwind experience where very narrow responsibilities at my, let’s call it my corporate job, where I had a couple of things that I was supposed to check off every day and do them really well and that’s great. Kind of as is true with any start-up and we’re no different, we have less than 30 employees and it’s ultimately a very small company, even though we do have a fairly large audience. You wear a lot of different hats. I’ve been given the opportunity to wear those hats and the only requirement of me was just to be honest and transparent about what I’ve learned along the way, while managing those responsibilities, and being upfront about mistakes that I made along the way.

That’s great. When there’s something you don’t know, how do you go about learning it?

Shawn O’Malley
That is a great question. One of the wonderful things that I think is a huge advantage for our company is that, we’re a stock investing podcast company at our roots. So over the years, every week, multiple times a week, we’ve had some of the world’s best investors on and sharing wisdom, book recommendations, and podcast recommendations. Continuous learning is a value that we actually take really seriously and put into practice that TIP because we’re on it during the day. We’re all a bunch of nerds who like listening to stock investing podcasts and that tells you a lot about the type of people that we are.

We’re also the type of people that are always–the first thing I did when I was in a position to manage others on the team and kind of got promoted from a writer to a manager was I think I read two or three books on management. Obviously, you can’t find all of life’s answers just by reading books but some combination of soaking up wisdom from some of the wonderful guests we’ve had on our podcast over the years, looking for books that were really insightful, and then also just testing things. Real-time has probably been the formula generally that we use that TIP and the word we use this is to mimic others who have found success. Whatever we’re looking to do, and either building a newsletter business or doing something different with podcasts, or like I mentioned, I was originally interviewing to be a YouTube host. When we were studying other YouTube posts to see what they had done well and figuring out what we could mimic and clone and replicate what we could do better than them. Then obviously, testing that and learning for ourselves. Okay, hey, this doesn’t work, we should do this differently. This is too hard to do. It’s some blend of almost what I would call theory and practice.

Laurie Barkman
What advice would you give to business owners, when it comes to recruiting and retaining Gen Z talent?

Shawn O’Malley
I think Gen Z is eager to learn. We started out with the internet in our hands from an early age and that doesn’t make us smarter by any means. Maybe we seem like wizards using iPhones or iPads or whatever it is, but I think Gen Z is a curious generation and the sense that we’ve just from an early age. We had all of the world’s information available to us, at our fingertips. So encouraging, at least speaking for myself, I don’t know how much you can project that onto an entire generation, but I really do think that encouraging Gen Z workers to embrace that curiosity, and feel comfortable learning.

With my own experience, just having a lot of trust, I do feel like a lot of my friends and colleagues and people I know who are around my same age, we’re all really eager to jump into the workforce. If I had worked that corporate job I was at before, I would have never been given the trust that I have today. I actually told Stig My boss wants and I said, I would have been a mediocre worker at a company with 50,000 workers if you hadn’t given me this opportunity. I was nothing special at my last job. I’d like to think I’m pretty good at my job now or at least really passionate about it. Before we had some performance statistics, I think I was like the second or third worst on a team of a dozen people where I did just enough to get my annual bonus. It’s because you’re operating in a system where you’re not encouraged to pursue your curiosity, you’re not encouraged to fail fast, experiment and try things, and take risks. Ultimately, you’re just not given a lot of responsibility because you’re plugged into this, this huge sort of organization, which is just the reality of working at a big company.

At least for me, I found it extremely beneficial to be encouraged to test things and experiment and fail and learning that it was okay to fail. One thing that we did, that I would probably call a failure through the newsletter is we wanted to host this stock investing competition, and we’re gonna give $1,000 to the winner and encourage people to participate in it. And hope that it would be a means of engaging the audience and getting them to promote it with their friends and get a whole bunch more people to sign up for the newsletter by participating in a stock investing competition. I don’t think it drove any new subscribers, like five or six, maybe a few more people even submitted applications to do the competition and we still had to give somebody 1000 bucks. It ended up being 1000 bucks isn’t a lot, but also when I was like 23 and it was like my first initiative with the company. I was like, I just wasted $1,000 for the company and that’s not a great feeling.

I don’t remember anyone pointing a finger at me getting mad at me even blaming me, the response was, it didn’t work. What can we learn and what can we do differently? Sincerely, I get it. That’s really what it was and I actually really did learn that it’s okay to fail which I think that especially for people early in their careers. That’s not a lesson people learn soon enough because I know speaking from experience, I would still be working this way and this feeling of like, hey, it’s not okay to fail. You can’t make mistakes. You have to be perfect because honestly, that’s what you’re taught in school. If you’re recruiting kids from really high-end competitive colleges, they’ve all been taught to score perfectly on exams and not make mistakes. It really is kind of an eye-opening experience, when somebody says, it’s totally fine that you lost money for the company, that’s not the problem. The only reason we’d be upset with you is if you did that and didn’t learn anything from it.

Laurie Barkman
Where do you see yourself in the next 5, 10 years?

Shawn O’Malley
I’ve really tied myself to this newsletter business that we’re building at The Investors Podcast and the newsletter is called, We Study Markets. We’re up to 36,000 readers nowa andwe have two other writers who I manage, who work on it. We have a fully devoted salesperson who works with advertisers to monetize it and bring in revenue for the newsletter. We’re sort of probably breakeven, but also we’re spending a lot of money on ads to grow it. So the hope is that within the next three to five years, it will be a profitable multimillion-dollar business unit.

In that sense, I feel a lot of pride in being an intrapreneur as opposed to being an entrepreneur. Even though I love the fantasy of being an entrepreneur, which I think a lot of people love. Realistically, I never would have been the person to quit my job and put a bunch of money on the line to do something as uncertain as starting any company. With tip, they gave me the opportunity to have a baseline salary, which covered my needs, and then capture a lot of the upside of being an entrepreneur who figures out how to build this newsletter business tip, has a nice audience in the podcasting world.

It was hoping to diversify into a broader media company, and get a little bit less of our revenue coming explicitly from the podcasting business and get new revenue streams coming in. That was why the newsletter business opportunity was appealing to tip. I was given the opportunity to build that as an intrapreneur. I sometimes I ask myself, I am I incentivized enough to work on building the newsletter into hundreds of thousands, millions of followers, subscribers down the road, and I think I am. And that’s because to some extent, I feel like I owe a debt to how much trust was given to me at such an early age and how much responsibility it was given to me that I feel extremely loyal to tip.

In this situation where I had a baseline salary that covers my basic cost of living and takes a lot of the risk out of entrepreneurship and intrapreneurship, while also incentivizing me to, hey, if you build this in a million-dollar business, you can also be making well north of six figures or whatever it is based on kind of a percentage of revenue and ad sales as we have it structured.

I guess that was a really long answer. The short answer is, as long as the newsletter business keeps growing, I hope to be there growing it, I hope to make it into a multimillion-dollar business, I hope to have a team of people reporting to me and continue to grow that and ultimately, I to some extent, I hope to pay back the generosity and investment that was made in me so early by Stig and by tip by turning the newsletter into a successful business.

Laurie Barkman
I love it. Shawn, if people want to subscribe to the newsletter, learn more about it. What’s a good way for them to connect?

Shawn O’Malley
You can connect with me on Twitter.I believe it’s is the URL. I’m sure we’ll have that in the description. It’s the easiest way to just go through and you can see the full archive of all of our past newsletters. Like I said, we do one every day.

You can also go to Generally, you’ll also find links to the newsletter there and you’ll find all of our podcast content and many of the wonderful interviews that we’ve done.
Laurie Barkman
We’ll definitely have the links in the show notes. No doubt about it. Shawn, thank you so much for coming on Succession Stories, and I love how you talked about being an intrapreneur and how the organization is building this startup. We’re gonna have you back on when you are on 100,000 subscribers and say, look back at that. It didn’t take us as long as we thought. Wouldn’t that be fun, though?

Shawn O’Malley
That would be a blast. I’ll be counting down the days till it happens.

Laurie Barkman
Absolutely! To our listeners, thanks so much for tuning into Succession Stories. Be sure to subscribe in YouTube and of course, on your favorite podcast platform from tune in next time from transition to transaction.

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