Founders Q&A: From Passion to Powerhouse - The Success Story of Shawn O'Malley and We Study Markets 🚀📰

Meet Shawn O'Malley, the bright mind behind the successful We Study Markets newsletter—your daily digest of the top three market stories made simple. Dive into his entrepreneurial journey and learn how he turned his passion for education and finance into a thriving business!

Q: Can you tell us about your personal background and how it led you to founding your startup?

A: I'm an intrepreneur more than I am an entrepreneur. After graduating college in Spring 2021 with a background in finance, I went to work for S&P Global (the company that produces the S&P 500 stock market index) while studying for and later passing level 1 of the Certified Financial Analyst examination.

I was on track for a very standard finance & investing career, though my passion is to educate others and write about things I find interesting. After listening to The Investor's Podcast Network through college and at the beginning of my professional career, I loved the educational investing content they created. When I found an opportunity to work there, I jumped on it and 'quit my day job.'

I was soon tasked with helping the company diversify into a broader media company beyond being just a podcast authority. I spent a few months studying other finance newsletters, and in July 2022, we launched our We Study Markets newsletter.

Beyond just being a copywriter, I've learned about the economics of the newsletter industry along the way, marketing and building an audience, working with advertisers for monetization, branding, managing a team, etc.

We have since grown into a newsletter business with hundreds of thousands in revenue, a team of 3 full-time workers, and 36,000+ email subscribers.

Q: What problem does your startup solve and how did you identify it?

A: Our newsletter fills a simple need with this elevator pitch: "The three biggest stories in markets, explained simply each day."

Traditional financial news like the Wall Street Journal is expensive and written for older generations. And easier to read, more relatable financial content for folks in their 20s and 30s is often too basic, lacking context and nuance.

We Study Markets is written for people who want to understand what is happening in the economy and financial markets, with an appropriate amount of context, without being dull and dry. After years of interviewing the world's best investors on our podcast We Study Billionaires, like Ray Dalio, Joel Greenblatt, Howard Marks, and many more, we are uniquely positioned to distill the big picture underpinning financial markets to everyday readers who are often not financial professionals.

In short, I made the newsletter that I wish I had been able to read every day when I first started getting curious about the economy and investing. Through TIP, I've had the opportunity to build that newsletter and the business surrounding it.

Q: How did the idea of your startup first come about?

A: As a podcasting company, we knew that we needed to diversify our revenue streams.

Following the example set by companies like Morning Brew and Axios with their successful newsletters, we found the newsletter industry to be particularly appealing and complimentary to our audio-focused podcasting business.

So we knew generally that we wanted to better utilize the emails we had collected from folks in the past while investing in building our own newsletter brand, which is where I came into the picture. I determined who the target audience should be, how the newsletter should be written and formatted, its style, and the logistics of sending it out 7 days a week.

Q: What is your startup's mission and how does it drive your daily operations?

A: Our mission is to empower and educate (primarily Americans) about the bigger picture around them and why it matters for their daily lives. For example, why is the Fed raising interest rates and what does that even mean? What causes inflation? Why do banks fail?

We focus specifically on answering the "obvious" questions people are too afraid to ask about because they may seem too simple. In other words, we often tackle things from a "first-principles" view.

This mission quite literally shapes everything we do, from the stories we select to write about, how we write them, and who we imagine we write them for.

Q: Can you share the story of how you gathered your founding team?

A: We Study Markets' team are all employees of our parent company, The Investor's Podcast Network (also known as TIP.) As mentioned, I was the first person hired to lead the newsletter initiative. I was selected by Stig Brodersen, TIP's CEO and co-founder. And then we've hired a few others along the way. The first writer to join me was Patrick Donley, who now drives sales from advertisers for We Study Markets.

Our next hire was Matthew Gutierrez who formerly wrote as a freelancer for The New York Times. He is now our Lead Writer and writes most of the daily newsletter. Our next team member to join was Weronika Pycek, who had worked at TIP previously making YouTube videos. She has joined as a partial writer for the newsletter who also manages our referral program (we give prizes to readers who recommend the newsletter to others), cross-promotions with other newsletters, and other supplementary things.

Q: How did you go about securing initial funding for your startup?

A: Since I am an intrepreneur, the funding has been entirely sourced from our parent firm, TIP. TIP sees the newsletter as a big investment, which includes the salaries paid to everyone who works on it directly or indirectly, as well as our $100k+ yearly budget for advertising the newsletter and expanding its readership.

TIP and We Study Markets have never accepted any external equity or debt investments. TIP was originally funded by our podcast co-founders' (Preston Pysh & Stig Brodersen) own funds and invested time and has since been funded entirely by TIP's retained earnings.

Q: What were some major obstacles faced during the early stages of your startup, and how did you overcome them?

A: As a company, our core competency is in podcasting, so even though newsletters are also in the media space, it was a whole new business to learn. And while I didn't have years of podcasting experience to bias my work for the newsletter, being relatively fresh out of college meant that I've had a lot to learn generally about building a business.

For a while, we struggled to determine whether the newsletter should exist primarily to boost TIP's podcasts, meaning the newsletter would just summarize or frequently link to our podcast content with a lesser focus on original content and writing, or if it should be its own brand with its own original content.

After first leaning towards being a vehicle for promoting our podcasts, the newsletter has increasingly taken on a life of its own and is now entirely original content. Many of our readers now are likely not even familiar with TIP's podcasts.

Q: Can you tell us about a time you failed and what you learned from it?

A: For the first few months of the newsletter, I split my time doing something else: Making videos for TIP's YouTube channel. I studied content creators, bought expensive camera equipment, and worked with TIP's editing team to produce and test a range of different videos, from book reviews to stock investing tutorials.

Evidently, this didn't pan out and was a huge distraction from focusing on solely the newsletter business sooner.

It certainly showed me the importance of failing fast. In the grand scheme of things, we did fail fast and abandoned the initiative after a few months, but on the other hand, I stubbornly insisted on collecting more data and testing more videos before determining the YouTube project wasn't worthwhile, even though the original results were very poor.

We had a 100k subs on YouTube acquired just from posting podcast clips, and after posting a few videos from myself which were a different type of content (more native to YouTube), it was fairly clear that the audience wasn't loving the videos.

Q: How does your startup stand out from competitors in your industry?

A: I would say the most unique thing is our connection to an existing media company, rather than starting from scratch. Our podcasts have over 140 million downloads, and that huge audience is a big advantage. TIP's brand is well known in the stock investing niche, and that lends a lot of credibility to what we're doing with our newsletter.

Q: What has been the most rewarding part of being a founder so far?

A: Since We Study Markets goes out everyday, it's incredibly rewarding to see a unique final product at the end of each day when I sign off. Even better is when people write in to tell us how entertaining or educational the writing is. I've also come to enjoy managing the We Study Markets team of writers and our salesperson. It's incredibly rewarding to watch the newsletter grow and bring in more money while constantly focusing on improving its quality, too.

Q: Can you describe a typical day in your life as a founder?

A: In the mornings, I check over our Facebook advertising campaigns and review which ads to spend more on, stop, and brainstorm/create new ads to run. I also review applications for Boosts on Beehiiv, look through reader feedback and responses to the previous day's newsletter, go through analytics for the latest newsletter (number of opens, clicks, etc.)

I then check in with our writing team, editing their news stories and other content for the newsletter while adding in some of my own writing. I'll also typically have calls with TIP's CEO to talk about how the newsletter is growing and other strategies for growth we should focus on.

I'll also spend time doing the final proofread on a day's newsletter and sign off on it being sent out. Other time is often spent reading and studying other business founders, learning about markets, management, etc.

Q: How do you stay motivated during challenging times?

A: I often feel that I'm working my dream job, and even though not every day is a dream, I like to remind myself that a bad day in this job is infinitely better than a bad in a job I don't care about or am not passionate about.

I'm passionate about what I do, find it stimulating and challenging, and I'm highly motivated to keep growing the business — I'm both self-motivated as a matter of pride and also financially motivated (much of my compensation comes from a percentage of the newsletter's total revenue.)

I'd rather work 60 hours a work being (mostly) my own boss and support a company I believe in, than work on Wall Street or for some other big firm just to chase a guaranteed paycheck. There have been no shortage of challenging times, but it really does help to zoom out and remember why I'm doing this at all in the first place.

Q: What is the best piece of advice you received?

A: TIP's CEO, Stig, once told quite succinctly that "your reality is your reality." It can mean many things, but it's a great reminder about how things actually work. For example, if our newsletter comes off as too difficult to read to somebody, then no matter the fact that we market it as "easy to read," to them, it's hard to read.

And if we pride ourselves as being non-political, but someone perceives us as being political, then that is their perceived reality.

Being honest about how, for example, there are many different ways your newsletter might be perceived is important.

It's also very helpful in a management context. if you think you've treated an employee well, but they don't feel that way, then that is their reality whether you agree or not, and it's up to you to change how they perceive that reality, assuming you're interested in keeping them around.

So it's really a message to move beyond how you perceive reality and consider how others view things.

Q: How do you manage work-life balance, especially during intense periods of work?

A: It's not something I've always done well. Working remotely, I've been guilty of pouring myself into this business. Sometimes I'm involved with newsletter tasks from when I wake until basically I go to sleep. I find myself very consumed by it, which can be bad, but also shows that I truly care about what I do.

I do better about drawing boundaries on weekends, and I give myself some simple pleasures to indulge in (fantasy football, hiking, cooking, etc.)

The short answer is that it's still something I'm learning to navigate, but as I've grown more confident, I feel that I'm less compelled to work extremely hard to prove myself and focus more on trying to truly rest and reset so I can think more clearly about higher-level decisions.

Q: What strategies have you found effective for managing your team remotely?

A: As a company, we are scattered around the world at TIP (from the Philippines to Denmark and Poland), so we're all structurally used to working remotely. We all read the Culture Map to learn more about working on a multi-cultural team environment and being respectful and aware of cultural communication differences.

We rely heavily on Slack to communicate, but really, we operate with lots of trust in each other – there's no micromanagement. Without a great team and great people, it's hard to confidently work remotely as a manager without worrying about whether time is being wasted, which is why we put so much emphasis on hiring the right people who we don't have to constantly check in on.

Q: How has your leadership style evolved as your startup has grown?

A: I've become less of a people pleaser and more of a delegator. It's very easy to think that you know how things should be done best and that it would be easiest for you to just do them, but I've really come to appreciate the importance of transparently outlining why things are being done, how they should be done, and empowering others with the trust and responsibility to manage things themselves without even always needing your approval.

it's easier said then done, but I hope to continue building great systems to plug talented people into, rather than trying to directly be involved in putting out every fire.

Q: What does success look like for your startup, and how do you measure it?

A: As a company at TIP and on the newsletter team, we focus on "optimizing for happiness." We could easily raise money and pour it into growing faster, but then we'd be beholden to outside investors, which would likely make us all unhappier.

From the top down, TIP encourages everyone to do what they're interested in, because that's what you'll do best. Write about topics you like, for example, and the audience will sense your passion.

In terms of measuring how we optimize for happiness, instead of just optimizing for profits, we look at the number of full-time team members who have left under their own discretion as a gauge of how happy folks are. If more people are leaving on their own, that signals your company may not be a good place to work.

Q: How do you encourage a culture of innovation within your team?

A: On the newsletter team, everyone's bonuses are pegged to KPI's related to the business's growth so we're all incentivized to feel like owners in the business to an extent. This certainly helps with innovation and our commitment to quality.

We've also interviewed so many great innovators on our podcasts, we all take pride in reflecting on those episodes and discussing takeaways, which reverberate across the company and forma culture of innovation.

Q: Could you share any pivots your startup had to make and the reasons behind it?

A: See my answer before about biggest challenges, where we pivoted away from thinking about the newsletter's purpose as a "top of the funnel" asset meant to filter people into TIP's other podcasts and YouTube content.

That approach makes it hard to have outside advertisers specifically for the newsletter, and We Study Markets often got added as a cherry on top to sweeten deals with advertisers on our podcasts, which doesn't exactly incentivize us working on the newsletter to grow it into a distinct business.

So I began focusing more on making We Study Markets into an original publication with its own branding, tone, and style, so we could build an audience that overlapped less with our podcast audience, which makes a better business case for it as a distinct business.

Q: How have you leveraged technology to grow and improve your startup?

A: We use AI-powered apps like Grammarly to automatically proofread everything we write and help catch mistakes. We also use ChatGPT to help overcome writers' block or to research topics.

We make great uses of Google's suite of free services (for example, we do a lot of our editing in Google Docs.)

Q: What is one thing you wish you knew before starting your business?

A: Once you lose a subscriber, they're probably gone forever. Not everyone is going to love our newsletter and there will be unsubscribes, but don't lose folks for stupid reasons.

Maybe the font is too small on their device, or there are to many grammatical mistakes, or you made something unnecessarily political, or you linked to paywalled things too many times, and so on, don't lose valuable subscribers from operational mistakes — growing is already hard enough as it is.

Q: Can you discuss a time where customer feedback directly influenced a decision or direction for your startup?

A: There's been lots of small tweaks we've made from listening to reader feedback, from making our font bigger to asking folks specifically what topics they're interested in. We also try to implicitly measure readers' interests by, for example, looking at the types of links people click on the most.

I can't point to one major change we made from reader feedback, but as mentioned, we try and improve the newsletter a little bit every single day, and that has compounded hugely over the past 16 months. Reader feedback has been incrementally important toward that compounding process.

Q: How do you see your startup evolving in the next 5 years?

A: I hope to build We Study Markets into a multi-million dollar newsletter business with hundreds of thousands of subscribers, a full team of writers and social media managers, a devoted sales team, and so on.

I'd also love to launch spin off newsletters or even acquire other newsletters, launch private membership communities or perhaps offer paid versions of the newsletter, and maybe even make a podcast derived specifically from the newsletter.

Q: How have you adapted your startup to changes in the market, especially during crises?

A: Yes — We've seen how volatile the advertising market can be, and we're looking to lean into other revenue streams that will offset our dependence on advertisers. For example, we are launching a paid stock investing course that we'll be offering soon.

Q: What are the key qualities you look for when hiring new team members?

A: One test we do is the airport test. We ask ourselves, is this someone we'd want to spend an hour with in an airport lounge? if so, they're likely a decent person to be around and work with.

We also like hiring people who are fans of TIP's podcasts, which typically means they share many of our core values and world outlook, as well as having just a better feel for who we are and what we do as a company.

Q: Can you share an instance where your team had to go above and beyond to deliver on a project?

A: With a daily newsletter, if someone is out sick, someone else has to shoulder all of the work and responsibility of ensuring the newsletter goes out at the same quality and at the same time. This is something I've certainly stepped up and done multiple times when other writers were out.

Q: How do you promote personal growth and learning among your employees?

A: At TIP, we have an educational benefit, where we'll pay for all books an employee reads for educational purposes so as to promote continuous learning.

Q: Can you tell us about a significant partnership or collaboration that has greatly benefited your startup?

A: Given our connections in the podcasting space, I'm often able to go on other popular podcasts and promote our newsletter. The biggest show, besides our own, that I've been on is Nicole Lapin's Money Rehab.

Q: What advice would you give to someone considering starting their own business?

A: Fail fast and reflect sincerely on why things have failed. Pain + reflection = growth

Pain with no reflection is just pain.