4 Career Lessons Learned on my Entrepreneurial Journey

4 Career Lessons Learned Entrepreneurial Journey
*author’s note: This post on the 4 Career Lessons I’ve Learned on my Entrepreneurial Journey originally appeared on I have reposted the first half here, but to read the remaining 2 lessons, you’ll need to click through to TechPoint. Also, this is just the tip of the iceberg of what I feel like I’ve learned over the past 6 years…so if you ever want to talk shop, just reach out! I could go on for days about this stuff, but they gave me a word limit ; )


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.

To see how the rest of my journey has unfolded thus far + to read the remaining 2 lessons, check out the full article on!

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