Saturday, November 5, 2022

Thoughts on Taking the Leap To Be an Entrepreneur

As with a lot of my blog posts, it’s half diary for me, half wanting to share with anyone who is interested, the why behind career moves, insights into some of my experiences and just generally things I’m learning. As of August of this year, for the first time since college I have taken the entrepreneurial leap and started my own company, Beeloo. If you're interested in what it is and where the inspiration for it came, you can check it out here.

In this blog post, I’d like to share more about how I came to decide to take this leap, which some consider to be drastic since I’ve worked my whole career for tech companies with at the smallest 500 employees, but usually large public companies with several thousand employees.

To fully understand current decisions, we got to go back to my first job ever. In high school, I had a moderately successful lawn mowing business in my town in the suburbs of Austin, Texas. I had a trailer, employees, commercial equipment and even a few commercial contracts. I earned more cash than a teenager should have, a lot of fun and learned many valuable lessons (like don’t take calls from a customer during a nap because you won’t remember what they said or who said it when you wake up). After that positive experience, it was only natural I wanted to continue being an entrepreneur for my career.

Once I got to college I focused my extracurricular activities on the goal of being an entrepreneur. I was the President of the undergraduate Entrepreneur’s club for my junior and senior year. As I got closer to graduation, the economy started to have a complete meltdown. (I graduated in 2009). I think I have a decent tolerance for risk but watching the housing crisis and everything else meltdown around me had me reassessing my plan. I accurately assessed that I had no money, no real skills and barely a professional network. It started to feel too risky to bet everything right after graduation. Ultimately, I decided I’d have to take the leap at a later stage in my career and I got my first entry level marketing job a few months after graduation at Salesforce, moved to San Francisco and started flying down the technology marketing career path. I remember a few friends and mentors being shocked because I had seemed so determined to start my own company. In fact, I remember talking through whether I should take the entrepreneurial leap with one of my professors and he told me “if you don’t become an entrepreneur now, you never will.”

The entrepreneurial itch was always there as my career progressed. I got more experience, built my network and was saving my money. I got an MBA and a few years later I made a riskier career move by joining a late stage high growth company that most people at the time had never heard of, Zoom. After four extremely intense years at Zoom, I felt my time at Zoom was coming to an end and it was time to scratch an itch, but the entrepreneurial itch was not the only career “itch” I had. I’m also interested in the public sector and public service. I had a goal for a long time to apply for a 1 year MPA program, which I explained in more detail in a blog post. After leaving Zoom in 2021 I went back to school full time. I loved my experience during my MPA program but of all the career paths and jobs I explored only one public sector job really stood out to me, which I pursued unsuccessfully. The timing did not feel right to go all in the public sector and public service, though my interest only increased during grad school.

During my year in grad school, I talked to a lot of friends and mentors to get their take on whether I should take the entrepreneurial leap after graduation. I constantly got two very different pieces of advice. One was “go follow your dreams, you're a go getter, I believe in you, if you want to start a company, go do it.” The other advice was “this is a bad idea, you're throwing your career away, go join another late stage company like Zoom, but at a more senior level pre-IPO and make a bunch of money. As an entrepreneur you could throw away the prime years of your career”. I fully acknowledge that if I was optimizing for corporate career growth or money, joining another high growth late stage company for someone like me is a no brainer. Part of me really wished that was something that I was excited about, but I just could not get excited about going down that path again.

My family situation and where we wanted to live also factored heavily into the decision. We have moved 4 times in the last 4 years across 3 states and with my oldest being 7 years old, we were feeling the need to settle down geographically. Before moving to Boston for grad school, we had bought a home in a suburb of Raleigh North Carolina, and really felt like that was a place that we could call home. Part of the appeal of North Carolina too was that our family “burn rate” could be so much lower than if we would have stayed in the Bay Area or settled in another large city. The tech scene in the Research Triangle is vibrant and growing quickly, making me want to be an active contributor to the community. Lastly, you work like a dog as an entrepreneur, but you get to decide where your company is based and you have ultimate flexibility, which is very appealing for my family given the age of our kids.

Years ago, after my MBA I worked at LinkedIn and I remember grabbing lunch with a colleague. Her and her husband sold their company to LinkedIn. I shared with her my entrepreneurial ambitions and she very bluntly said, “if you want to be an entrepreneur, just go do it, you don’t need any more notches in your belt.” That advice really stuck with me.

Overall, whether it be money, career or life decisions I try to think really hard about how much I will regret not taking a certain path and how irreversible the decision is. This all led me to taking the leap at this stage of my career. It might seem riskier, but it feels A LOT less risky than when I graduated from college. I have marketable skills and a deep professional network. This will help me with my current start up but also if I decide to return to a corporate job. I think one thing people worry about the most about taking the leap at this stage of life is money. You have to think about your bills, mortgage, paying for college for kids and healthcare. Since this is something that has been in my career plans for a long time, we’ve prepared financially, we can’t do this forever but given our low family burn rate we can give it a good shot.

Sometimes I envy people who have careers with a singular path, purpose and goal, but I have come to terms I’m not one of those people. I have a lot of things that interest me and if that means my career zigs and zags, that’s ok with me. Most startups fail, but I’m confident that regardless of the outcome of Beeloo this was the right path and decision for me at this time. If there are any aspiring entrepreneurs out there reading this, I hope this gives you the courage to take the leap and be comfortable with some intelligent risks.