4 lessons that led me to an entrepreneurial career in Indianapolis

If you would have asked me eight years ago what I imagined my career path would look like, it would have looked completely different than path I’ve actually followed. And I’m so glad it has turned out that way!

In college, I imagined myself working on the business side of a life sciences company – basically the opposite of a SaaS startup. Indy has a good reputation within the life sciences, and I thought large corporations were where people went to work after college, right? I landed what was theoretically the dream internship before my last year at Butler, but as great as the company was, I learned that corporate life wasn’t for me. When the Orr Fellowship came along, I just knew it was something I had to go for…even though I had only a vague understanding of what entrepreneurship in a tech context really was. In fact, I was so sure that there would be something better-fitting waiting for me if I followed the Fellowship’s path that I ended up turning down a solid job offer before the Fellowship’s recruiting process was even over.

Lesson #1

It sounds cliche, but listen to your gut. If you feel trapped in a job before you even accept it, it probably isn’t the position for you!

Fortunately, I was selected to be Slane Capital Partners’ first Orr Fellow. I couldn’t have orchestrated a better-fitting experience if I’d tried! Because I was part of a super small team, I got to touch almost every aspect of every project that came through the door. I was also given a ton of responsibility very quickly — everything from pitching at the first Innovation Showcase within a month of starting my job, to conducting an operational audit of a $10 million food business six months later. It was a true “get things done,” hands-off atmosphere, which gave me the room to explore, learn, create, and grow. Without that rapid on-ramp of professional experience, there’s no question that I wouldn’t have been able to take the next step: earning my MBA from one of the nation’s top business schools, The University of Chicago Booth School of Business.

For a little under two years, I commuted to Chicago on the weekends to gain broader exposure to more formalized business theory, much bigger companies, and a network of some of the most intelligent people I’ve ever met. For many evening/weekend students, getting an MBA is a turning point in their career, resulting in securing a promotion, entering a new industry, or even undergoing a complete career change. However, I completed my MBA under much different circumstances. I had been working on an internal product at Slane with Gerry Hays for almost a year, and we decided to spin it out as its own company three months after my graduation. It was always so interesting to me to see how my peers at Booth regarded me as an entrepreneur. Many of them romanticized and glamorized it, of course, but many others expressed to me their desires to start something of their own.

Lesson #2

If you are at all interested in working at a startup or starting something of your own, do it sooner rather than later. Life doesn’t get simpler. It usually gets more complex as marriages, babies, and the like are added, making it harder and harder to pursue something that’s riskier than what you’re currently up to. Waiting for the right time is something of a false notion. When the opportunity arises, yes, go for it! If you don’t, you may regret it later.

We ended up building a grocery tech startup over the next 18 months. Being a co-founder is such a unique experience, because when you’re a small, bootstrapped organization, you aren’t just a co-founder…you’re also chief strategist, product manager, brand manager, social media marketer, biz dev, implementation specialist, customer relations, and probably a dozen other titles I’m not listing. This took my previous experience to another level, because this time I wasn’t just helping someone else build their company, I was building one of my own. But, clearly I’m not helping to lead that company any more … so what gives?

Lesson #3

Timing always wins. You can’t force an outcome if the market isn’t ready.

Some people might consider this a failure. I don’t. How could gaining all the tactical experience I did be anything but a win? That said, key transitions in your working life can be stressful. If you’re able to take some time off before making your next move, I highly recommend it. It’s centering, it helps you focus in on what you want, and it makes you grateful when the right thing comes along. The time I took off to figure out the answer to “what’s next?” brought me full circle.

I considered, and interviewed for, positions at much larger corporations. I considered, and interviewed for, positions that were outside of Indiana (and heck, outside the US). I considered, and interviewed for, positions in very different industries.

I purposely avoided Indy tech startups for the majority of my time off because I thought I wanted something different. But I believe the interview process at a company reflects what it would be like to work there, which is why my interview experiences cemented for me exactly why Indy tech is the place for me to be.

The first tech startup in Indy I interviewed with was Zylo. It also happened to be the most wholly authentic interview experience I had.

Lesson #4

Don’t take it for granted when you connect with people. You’ll be spending a lot of your time with the people you work with, and the teams you’re surrounded with in the workplace make all the difference in your work experience.

I joined Zylo because it combined all of the aspects I wanted most in a job. I’m thankful for the other interviews because they helped me realize that the change I thought I wanted really wasn’t a fit for me at all. Zylo has passionate leaders, an open and engaging team, brand personality, the potential to shape an industry, freedom and flexibility in the workplace, and a fast-paced environment that is more focused on progress than politics. And, three months in, I’ve been welcomed not only as a “new” member of the team, but embraced and respected as a member of the team, period. I was able to jump in and work on impactful things right away, while learning the ropes on all the “new” stuff as I go, which is really what you hope for when starting a new gig, isn’t it? The opportunity and potential that lay before us is exciting, and I can’t wait to see how this part of the journey unfolds.

About the Author

After starting her entrepreneurial path with the Orr Fellowship, Central Indiana native Ashton Chaffee found a passion for startups. Whether it’s starting something of her own, helping others to realize their vision, or working as part of an energetic team, she loves it all! Chaffee received her MBA from Chicago Booth in 2015 and now works as Product Manager at Zylo.

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CATEGORY: Analytics, Procurement Technology CITY: Indianapolis

Zylo is the leading SaaS optimization and cloud intelligence platform. Discover, manage and optimize cloud investments within the enterprise

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ABOUT THE AUTHOR

Ashton Chaffee is product manager at Zylo, the SaaS optimization and cloud intelligence platform that works like an online command center for all cloud-based software used across a company.