Four CEOs On How Their Side Jobs Made Them Better Leaders

What side gigs as a firefighter, a rancher, an IT manager, and a startup mentor taught these CEOs about leadership.

Four CEOs On How Their Side Jobs Made Them Better Leaders
[Photo: Flickr user Tony Webster]

The CEO is arguably the most important job at a company. They are the nerve center, and their personality and skills can go a long way toward the future success of the business.


Some like Jeff Bezos grew into their leadership role alongside the growth of the company. Others like Sharon Rowlands are change agents who turn companies around. Then there are the Kat Coles of the world who take lessons from scrappy startups to run their established brands.

Learning on the job is one way to amass these skills. But Fast Company talked to four CEOs who have full-fledged side jobs that have taught them to be better leaders.

Bill HoPhoto: Mollie McPhee

Side Gig: Volunteer Firefighter

CEO Skill: Staying cool under pressure


One of the most basic job requirements for running a successful company is knowing how to stay cool under pressure. That’s especially important in an age where businesses of all sizes are subject to unexpected hits to their brands.

For a company built on maintaining the security of clients’ private files, especially given the continuous threat from cyber-hackers, it’s mission critical. But Bill Ho, the recently appointed CEO of  Biscom, a multi-million-dollar enterprise-secure file transfer company based in Chelmsford, Mass, has had excellent training.

And it hasn’t just come from computer science degrees earned at Stanford and Harvard or his MBA from MIT–although they probably helped–or from his 12-year tenure at the company where he rose through the ranks to president before taking the corner office.


Instead, Ho credits his work as a volunteer firefighter with the skill. After six months of training to learn how to fight fires and work as an EMT to be certified, he’s on call for 100 hours or more per month and estimates that he answers 1-3 calls per week on average. 

Putting out a fire is an extremely coordinated strategy that is applied to a very chaotic scene where there are a lot of moving parts, and good communication is critical. There are a lot of things that can and do go wrong, but the primary objective is to save lives, save property, and remove the danger of having the fire spread. I think that’s why a lot of emergencies at work are called “fire drills”–you’re looking at a major operation that needs to come together in minutes and failure will have sizable repercussions.

What I’ve taken from my side job as a firefighter is a clearer way to think under pressure, better understanding of objectives and priorities, and making sure you have the best team to work with–because your life can literally depend on your fellow team members.

Gay Gaddis

Side Gig: Cattle Rancher

CEO Skill: Making tough decisions

You may remember Gay Gaddis as being the chair of a “secret society for high-achieving women” otherwise known as C200. Gaddis herself has achieved plenty as founder and CEO of T3, the largest woman-owned independent advertising agency in the U.S. Founded in 1989, T3 now has nearly 200 employees across the country and was recently recognized by Forrester Research as one of the top five innovation agencies in the world and works with brands from Staples to 7-Eleven.


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But when it comes to the more quotidian of goals like supporting staff through an important project, Gaddis doesn’t always refer to the lessons she’s learned in the confines of her Austin-based agency. Instead she looks to her home on the range–that is Double Heart Ranch, where she and her husband Lee raise Longhorn cattle. 

In my second job as a Texas longhorn rancher, I do business with nature on a grand scale every day. The decisions we make on the ranch have an immediate effect on the welfare of everybody and everything associated with it. This has taught me a lot of great business lessons in a very real, close-to-the-bone way. Issues like mitigating risks that you can’t eliminate, surviving through times of adversity, and making the most of what’s at hand to ensure the survival of the whole herd, even if that means making tough decisions.

Being a longhorn rancher gives me an overarching perspective that has been invaluable as a CEO, and I think everybody who leads a business could benefit from spending a week on the ranch watching their decisions play out on a grand scale, completely in the moment.

Dan Graham

Side Gig: Startup Mentor

CEO Skill: Listening to other’s ideas


Dan Graham may have started in 2005, but the founder and CEO of the rapidly growing company never wanted to get far from its startup roots. Though he bootstrapped the Austin-based online custom printing provider of signage and home decor items which is now expected to bring in $90 million in revenue this year (up from $70 million last year) and has 300 employees, Graham still feels a kinship with entrepreneurs who are putting their sweat equity in at kitchen tables and coffee shops all over the city.

To help them, he started an incubator called Owen’s Garage that houses 10 companies that he helps mentor and support. 

I’ve invested in and mentored a lot of startups over the years, but when I decided to open Owen’s Garage, which serves as an incubator and coworking space for the companies I now support, that’s when I really began to see how much I could learn while giving back. The incubator keeps my entrepreneurial spirit alive and reminds me of where I got my start. It’s fast-paced, changes constantly, and keeps you honest when you see that sometimes even the best concepts end up failing fast.

Dealing with young founders has given me new ideas for tactics like social media marketing and app store optimization, and different perspectives on management techniques that I’ve been able to take and apply to my own business. There’s a scrappy way of doing business as a startup, and through my incubator I’ve been able to remind myself of the work that goes into founding a business. Sometimes as a CEO you get lost in the daily grind, so when I get the opportunity to be around young minds that are setting out to change their industry it invigorates me and pushes me to think about in a new way.

Tiannia BarnesPhoto: Ed Lefkowicz

Side Gig: IT Manager

CEO Skill: Managing a lot of moving parts


You could say Tiannia Barnes did what some people only dream about doing. The IT program manager followed her passion for footwear to become the founder and CEO of the eponymous high-end shoe company that launched in January of 2014.

Barnes’ background–degrees in math and industrial engineering combined with an MBA–as well as her status as single mom of a 10-year old understandably make her a little risk-averse. In addition to learning the fundamentals of footwear such as pattern development and design at a shoemaker school, Barnes continues to work in IT. In this way, she balances her love of fashion with her experience in math and science along with the company’s checkbook as it gets off the ground. As she says in the company’s tagline: Amazing Never Waits.

My work as a corporate IT Project/Program Manager has taught me how to be a puzzle master who knows where to put all of the right pieces for success. One of the biggest things I’ve learned is how to build a strong team with the right skill set and cost model by hiring consultants to fill in some knowledge gaps. As the CEO of a luxury women’s footwear brand, it’s all about knowing your product and understanding your target audience.

As a startup, it’s critical to streamline your business and know where to spend dollars and where to be lean. Since January 2014, I’ve brought in team members to help mitigate any issues that might occur during my shoe-making process and to prepare me for the Fall/Winter ’15 launch. I applied the same principles I use day to day as a program manager to building my business, and this has helped me tremendously with getting my business established.



About the author

Lydia Dishman is a staff editor for Fast Company's Work Life section. She has written for CBS Moneywatch, Fortune, The Guardian, Popular Science, and the New York Times, among others.