Jack Hallahan of Swimming World: From Avocation To Vocation; How I Turned My Hobby Into A Career

An Interview With Jason Hartman

Jason Hartman
Authority Magazine
14 min readMar 17, 2024

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Understand How to Navigate and Transform the Company’s Culture

I wish someone had told me more about this before I started because this is a recurring challenge anyone will face when coming to lead a company that’s been around since 1960 and is in need of reinvention to be relevant in today’s world. I am constantly seeking out advice and guidance from founders and colleagues on how this process will take place and ways to overcome the challenges of changing cultures.

As a part of our series about entrepreneurs who transformed something they did for fun into a full-time career, I had the pleasure of interviewing Jack Hallahan.

Jack Hallahan, co-owner and publisher of Swimming World and H2Media, is a seasoned executive with over three decades of experience in digital marketing and a proven track record of leading digital transformation and personalization initiatives. Specializing in publishing, digital commerce, Martech, Adtech, and AI/ML platforms, his expertise has earned Emmy Awards for innovations in video, advertising, marketing personalization, and ecommerce for established and high-growth brands.

Thank you so much for doing this with us! Can you tell us a bit about your “childhood backstory”?

Growing up in Virginia, my journey into swimming started with a splash! As my instructor took me across the pool, I recall my mom saying, “he seems to be doing very well.” As they were talking, I started swimming back across the pool by myself. My mom said, “Well, I guess we can cancel the rest of the lessons.”

From that moment, swimming became my obsession. Waking up early to sneak into the local pool for extra practice sessions became a daily ritual. I had a strong desire to do whatever it took to improve my skills. Before I knew it, I was climbing the national high school ranks and earning a scholarship with Villanova University’s Division One swimming program. A debt of gratitude goes out to my family and friends for pushing me to success…but most importantly to Coach Tom Healey who made me believe in myself and constantly refined my aquatic skills.

The discipline, dedication, and hard work required to become an elite swimmer has remained a guidepost for how to go about just about everything I do in life…and has propelled me to where I am today.

What was the catalyst from transforming your hobby and love for swimming into a business? Can you share the story of your “ah ha” moment with us?

A few years back, college roommate and fellow Villanova swimmer, Matt McKean, joined The International Swimming Hall of Fame Board, which owned Swimming World magazine at the time. However, the publisher, Brent Rutemiller, who for decades built the foundation of what Swimming World is today, fell deeply ill with stage four cancer. Additionally, the COVID-19 pandemic and subsequent shutdown took a huge bite out of competitive swimming — which in turn impacted all news outlets that report on the sport. These two barriers really damaged the company and painted an uncertain future.

Matt and fellow ISHOF Board Member Steve Hasty (now my business partner) asked me to come in and help them figure out how to turn Swimming World around and return the brand back to its original prominence.

Almost a year ago today it all started to take shape with a conversation about merging Swimming World’s passion for the sport with USA Swimming’s massive reach. By teaming up, we solved their dilemma of no longer being capable of publishing USA Swimming Splash Magazine by collaborating with as their Official Publishing Partner.

Today we have successfully re-energized our brand while bringing USA Swimming’s Splash Magazine back by incorporating it into a Swimming World. USA Swimming members now have easy access to all the USA Swimming content, along with Swimming World at their disposal to understand the entire international circuit as well.

There are no shortages of good ideas out there, but people seem to struggle in taking a good idea and translating it into an actual business. How did you overcome this challenge?

Turning a hobby into a business can feel like swimming against the current. We needed to change the brand to attract a younger audience. If Swimming World is the authority in the sport, how can it be reimagined for a contemporary audience?

From a business standpoint, I had to look at Swimming World as a property and an offering and identify what needs to be prioritized to bring it back to the forefront of the Swimming community.

Swimming World goes above and beyond, covering a vast array of the aquatic lifestyle from new tools and innovation in swimming, proper wellness and nutrition for swimmers, motivational tips, the history of the sport, etc. The content was there…just not formatted for easy consumption. The solution: packaging. Motivational Monday, Tech Tuesday, Wellness Wednesday, Throwback Thursday, and Friday Funday. With themed editorial calendars and interactive experiences, we made a splash in the swimming community, doubling our readership and breathing new life into our brand.

Collaborating with Editor in Chief John Lohn, we are enabling more engaging experiences with quizzes, polls and social media interaction that bring community into the conversation, where in the past our readers were on the outside looking in.

What advice would you give someone who has a hobby or pastime that they absolutely love but is reluctant to do it for a living?

If something is important to you, you shouldn’t let it go. Find 10% of time in your day to manifest your hobby into something that could potentially be the next big thing you do in life. Even if you don’t ever turn your hobby into your full-time work, at least you’ll get to dedicate a portion of each day towards something you love. Take that hobby or pastime and make it an important part of your day-to-day, integrated into the overall arc of your routine.Take that time to tinker with your concepts so that you continue to make your ideas take shape and feel a sense of regeneration. That helps keep the fire going.

Dive in headfirst! Get involved in your hobby on a deeper level. If you loved baseball growing up, see if there’s a Little League down the street where you can get involved. Once you get involved, allow the universe in, so to speak. Put yourself in the universe and that energy comes back to you.

It’s said that the quickest way to take the fun out of doing something is to do it for a living. How do you keep from changing something you love into something you dread? How do you keep it fresh and enjoyable?

Anytime you feel burnt out or overwhelmed, just take a step back and be grateful for where you are. Gratitude is a powerful healer. Today, I’m 100% grateful that I have this opportunity in front of me. It’s very rare to bring your vocation and your avocation together. I do occasionally think about whether taking this on could spoil my passion for my sport, but even when it gets to be a bit of a trudge or a challenge, I stop and remind myself that this is something most people and even myself would love to have the chance to do. Knowing that, I’m able to take those hard days in stride.

It also helps to have support from my wife Lisa and our swimmer/water polo/ rowing kids Pat, Griff, and Helena offering insights and rooting me on! Friends like Matt McKean and a brotherhood of swimmers in my life also keep things fresh as they feed ideas and offer support.

What is it that you enjoy most about running your own business? What are the downsides of running your own business? Can you share what you did to overcome these drawbacks?

What I enjoy most about running the business is the people I get to work with every day. I just enjoy being around these journalistic professionals, watching them in action and learning from their skills while also passing my knowledge out or sharing experiences.

I also really enjoy getting to hang around with the most prominent figures in the sport, from up-and-coming athletes, and storied veterans of the sport, to coaches who are shaping the latest generation of world class swimmers. It’s an honor to be invited to have open discussions and listen to their stories. Being that I’m such a fan of the sport itself, this is probably one of the most enjoyable parts of the business that never gets old.

The downside to running the business is that it’s always on. I have to figure out how to turn it off. Speaking personally, I need to remind myself to not be dull and boring when I’m around my friends and my family by bombarding them with everything happening at Swimming World and in the swimming community. On one hand, that’s exciting for some people; they feel your enthusiasm and passion, but after a while, that excitement runs its course for most people and becomes stale. I have to remind myself to turn off this button that seems to be stuck in the on position almost all the time.

Can you share what was the most striking difference between your actual job and how you thought the job would be?

The most striking difference is that there’s a lot of day-to-day processes to deal with in the business that are essential, yet when you’re doing those things, it often doesn’t feel like you’re moving the needle. Yet, that’s what most businesses are about — pay attention to the backend and the front end to make things work.

Running a business is like riding a wave — it has its highs and lows. But the best part? Surfing with an awesome team who want to bring more awareness to the many enjoyable aspects of aquatic sports.

Has there ever been a moment when you thought to yourself “I can’t take it anymore, I’m going to get a “real” job? If so, how did you overcome it?

I’ve had “real jobs” my whole career. I almost want to take this question and flip it upside down because I look at Swimming World as the most real job I’ve ever had. My business partner, Steve Hasty, and I now have the legacy of Swimming World resting squarely on our shoulders. Responsible for how this ship moves forward. We also have the opportunity to reimagine Swimming World and bring it back to that place of prominence it displayed during its heyday. There couldn’t be anything more real than that. The day-to-day responsibilities of effectively being CEO offers magnitudes of reality beyond anything I’ve ever done.

The best mentors I’ve ever worked with often said, “When you get up in the morning and go into work, think about how you would do your job if you owned the company.” So, from the moment you walk into the office to the minute you turn the lights off to head home, think about what you would do differently if this were your company. This always resonated with me because even when you feel like a cog in the wheel, you can reset your mind and regain a sense of purpose if you stop and ponder the question, “if this was my company, how would I do my job differently? Or, am I doing it exactly how I would go about things if it was my company?” Maybe that’s a better way to reflect on the idea of getting a “real job.”

What are your “5 Things I Wish Someone Told Me Before I Started” and why?

1. Understand How to Navigate and Transform the Company’s Culture

I wish someone had told me more about this before I started because this is a recurring challenge anyone will face when coming to lead a company that’s been around since 1960 and is in need of reinvention to be relevant in today’s world. I am constantly seeking out advice and guidance from founders and colleagues on how this process will take place and ways to overcome the challenges of changing cultures.

2. The Difficulty of Setting and Sticking to Priorities

When Jack Welch was running General Electric, he’d start the year by having everyone agree on five objectives that the company is going to try to achieve. Once they agreed, he’d tell them that they have to be unwavering and undistracted in achieving those goals. Even if unpredictable things come up and new objectives get added to that list, don’t lose sight of what you had set out to do that year. If you wander off course, you may damage your potential for success and ability to achieve priority goals. It’s a bit of a tight filter Jack Welsh sets and it’s really difficult to adhere to, but it’s worth the effort to maintain that standard.

3. The Importance of Managing Expectations

It’s important to set big goals, but it’s just as important to be realistic about what’s achievable in any given time frame. You have to be careful that you don’t get swallowed by the expectations you set for yourself and the company. I wish someone had cautioned me to not get consumed by the ups and downs of this journey.

4. The Need for Patience When Reshaping a Brand

It takes time to reposition a brand in the eyes of the audience. In the beginning, I may have been too impatient trying to get Swimming World to recover and overcome the challenges facing this brand. It’s a process and a slow build, but progressive change is also change for the better. It takes time to achieve that outward objective of shifting people’s mindset about this brand in the swimming community. We want them to recognize that what we’re doing now is still the same top-notch journalism and content, now offered in different ways across various mediums so that it is contemporary, more digestible, and far easier to access than ever before. It takes a while for that message to resonate.

5. The Fast and Relentless Pace of Handling a Business

My days fly by and there’s never a dull moment. The business has a startup feel despite the fact that Swimming World has been around for decades. Each day, everyone has to step up to the plate to consider what we could be doing to better further our efforts with what we have. What’s working? What needs to be reimagined? Are there aspects of the business that need to be completely thrown out? What areas need the most attention and resources right now? Which operations are running smoothly? It’s a constant rebuilding mindset. Revamping. Rethinking processes and adding talent to keep moving forward.

Who has inspired or continues to inspire you to be a great leader? Why?

This question sets off a tapestry of voices in faces I have been fortunate enough to work alongside of over many years. I hear their comments in my head all the time…”Listen. We have 2 ears and 1 mouth for a reason.” Or “Be emphatic. Be Open. Ask questions.” Other times, it’s “Remember the best asset your company will ever have walks in that door everyday. Be sure to thank them and let everyone know when a job has been well done.” Finally, recognize and reward talent. Ask them to help find your next great employee. Empower leadership across the organization. I still hear you…from inspirational coaches, co-workers, bosses, and friends all of whom have taught me so many lessons I will never forget.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

I make mistakes every day. Some are funny…some not so much!

Usually mistakes help me understand my limitations. Most of my mistakes have been resolved by discovering there are people around me who can get that task or project done…and I don’t have to be so deeply involved.

How have you used your success to make the world a better place?

When life hands you success, why not share the wealth?We are leveraging this platform to make waves in the swimming world by moving beyond competitive swimming to include more water polo, diving, open water, and artistic swimming. We want all aquatic communities to have an opportunity to be heard. After all, it’s more fun to share the pool and swim together!

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

I was a pool lifeguard during my school years with a lot of time on my hands. My Dad handed Winston Churchill’s compendium and said, “Read Churchill…you’ll thank me later!” My favorite quote from those readings, “Success is not final, failure is not fatal: It is the courage to continue that counts.” Keep this gem in your back pocket, and you’ll weather any storm life throws your way!

We are very blessed that some of the biggest names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them.

Imagine sharing a meal with Rowdy Gaines! The chance to spend time with a swimming icon like Rowdy…his knowledge and passion for the sport…the moments he witnessed over the past 40 years at Olympic venues…that would be a dream come true. Who knows? Maybe we’ll cook up some ideas to make a bigger splash in the swimming world!

Thank you for these fantastic insights. We greatly appreciate the time you spent on this.

About The Interviewer: Jason Hartman is the Founder and CEO of Empowered Investor. Jason has been involved in several thousand real estate transactions and has owned income properties in 11 states and 17 cities. Empowered Investor helps people achieve The American Dream of financial freedom by purchasing income property in prudent markets nationwide. Jason’s Complete Solution for Real Estate Investors™ is a comprehensive system providing real estate investors with education, research, resources and technology to deal with all areas of their income property investment needs. Through Jason’s podcasts, educational events, referrals, mentoring and software to track your investments, investors can easily locate, finance and purchase properties in these exceptional markets with confidence and peace of mind.

Starting with very little, Jason, while still in college at the age of 19, embarked on a career in real estate. While brokering properties for clients, he was investing in his own portfolio along the way. Through creativity, persistence and hard work, he earned a number of prestigious industry awards and became a young multi-millionaire. Jason purchased a California real estate brokerage firm that was later acquired by Coldwell Banker. He combined his dedication and business talents to become a successful entrepreneur, public speaker, author, and media personality. Over the years he developed his Complete Solution for Real Estate Investors™ where his innovative firm educates and assists investors in acquiring prudent investments nationwide for their portfolio. Jason’s sought after educational events, speaking engagements, and his popular “Creating Wealth Podcast” inspire and empower hundreds of thousands of people in 189 countries worldwide.

While running his successful real estate and media businesses, Jason also believes that giving back to the community plays an important role in building strong personal relationships. He established The Jason Hartman Foundation in 2005 to provide financial literacy education to young adults providing the all-important real world skills not taught in school which are the key to the financial stability and success of future generations. We’re in a global monetary crisis caused by decades of misguided policies and the cycle of financial dependence has to be broken, literacy and self-reliance are a good start. Visit JasonHartman.com for free materials and resources.

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