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Alumni Advice: Thomas Stirling on What It Takes to Start a Business as a Millennial

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By Sarah Tuff Dunn

Knowing when to start a business is always a challenge, so we sat down with Thomas Stirling ’10 to learn about his background and get some valuable insight into how he was able to start a thriving web design and marketing agency while he was still at UVM.

Growing up, Stirling was influenced by a growing entrepreneurial community in his hometown of Winchester, Massachusetts. As a child, he found himself drawn to the challenge of fixing and repurposing hardware, and he loved taking apart broken technology. During middle school and high school, he rounded out his skills, taking some basic web and flash programming classes paired with photography and art. Later Stirling went on to attend UVM, majoring in computer science and information systems while minoring in economics.

uvm-alumni-advice“I’ve found networking and being active in the community to be a key to success,” says Stirling, whose résumé includes working with many nonprofits and volunteer organizations. As a result of these activities, in 2015 he was elected president of the Woburn Business Association. In addition, he is an active member of the Winchester Chamber of Commerce. Meanwhile, the company that he founded, Stirling Technologies, hosts interns, mentors local students, and is part of the UVM job shadow program.

Located in the Boston area, Stirling Technologies provides an array of design, development, and marketing services for the web to corporations, organizations, and nonprofits, as well as to individuals. His services include developing dynamic websites, custom software, iOS and Android apps, online advertising, and digital strategy.

What made you want to launch your own company?

While at UVM, I was enrolled in an independent study working with UVM Medical Center (then Fletcher Allen Health Care). After our initial work, the project evolved into freelance work, which I found very fulfilling. As my client base grew, I was able to hire other UVM students and relocate the business to the Boston area after graduation. There’s nothing more challenging and rewarding than being part of a startup company. As the business grows, roles are constantly changing, providing new opportunities.

What books or other resources helped you in that process?

Early in my career, I forged partnerships with and joined local groups such as Business Networking International to expand my reach in the area. Continuing education is important in any career. Many books have provided relevant insights for my business, including The Lean Startup, Predictable Revenue, SPIN Selling, The Personal NBA, and Three Feet from Gold. Television shows such as Shark Tank and The Profit on MSNBC also provide valuable insight into the minds of other successful—and unsuccessful—business owners.

What’s your prediction for the future of the web?

In many ways, like the dot-com boom, we’re at a technological crossroads that is happening right now across the world. We’re just seeing the beginning of what has been named the “Internet of things” and “big data,” which is going to fundamentally transform the web into a much larger digitally connected world. Smartphones are just the first step toward smart homes, smart cars, and intelligent devices all connected on one central network. While critics have security and privacy concerns, as developers we see a bright future where these devices all work together in perfect harmony, allowing all of us to be even more connected in our daily lives. Only time will tell, but what is important is that these changes will bring new jobs and opportunities in the technology space.

What advice do you have for millennials hoping to launch their own businesses?

In many ways, there has never been a better time to start a business. Thanks to technology, the barrier to entry and the startup costs in most industries are low. If you’re considering a business that requires little overhead to start, I would advise giving it a shot, part-time, as a hobby. No need to wait for a detailed business plan—get your idea out there and see how it’s received in the market. If it starts to grow wings, then you can always quit your day job and pursue your dream full-time as I did. If your idea never gets off the ground, the experience will prove invaluable and lessons learned can be applied to your next venture.

What if your idea requires a larger initial investment?

If your concept requires more to get off the ground, in today’s world you have two great options. If your idea is a fit, Kickstarter is the place to launch your business since you don’t need a working product to start getting funding. You just need a fancy, catchy presentation or video to entice your prospective users. This is similar to acquiring venture capitalist funding, where the goal should always be to have a low-cost initial prototype before investing too much capital. So if Kickstarter isn’t a fit, the model is still the same, but it will be a much longer road, requiring a more formal business plan and financial projections. Until you get funding, don’t get distracted and don’t over invest in your idea until you get this validation.

-Sarah Tuff Dunn is a freelance writer from Shelburne.