My Next Play

I recently made the decision to leave LinkedIn after 2.5 years (and California after 4 years) and wanted to take an opportunity to share with you all why I made this decision, as well as a look into what I have planned next.

Before looking towards the future, I want to take a brief moment to rewind to the past. In the fall of 2016 I was deeply conflicted as to what I wanted to do after college. On the one hand, I had a burning desire to form a team and start my own company. From my sophomore to senior year I entered into every innovation competition on campus (winning $30,000+ in prizes) with projects ranging from an E-Waste recycling project to a Smart Gym app . And by my final semesters, you were more likely to find me tinkering in the IoT lab or doing volunteer marketing for Fetch Rewards (now a $1 billion company ) on a Saturday than at the bars.

However, as I was wrapping up my final semester at UW-Madison I was forced to confront some uncomfortable realities. We had spent the previous summer trying to get our latest project Cascade off the ground to no avail. This failure would have been embarrassing enough on its own, but to make things worse, we had to fly out to Qualcomm headquarters to present our progress, since we had won 1st place & $12,000 at their innovation competition. In the Qualcomm board room in San Diego, I explained to a room full of execs how we had failed to land even one paying customer for our software product. It was one of the most humbling experiences of my life.

Off the heels of my latest startup failure, I decided to lick my wounds and take the safe path by accepting a APM position at Intuit out in Silicon Valley. In hindsight this was probably the right decision as I was starting at 6 figures and it would provide me the opportunities I needed to learn (and make mistakes) on the company's dime as opposed to my own.

I told myself that my decision to join big tech would be temporary, but after 1.5 years at Intuit I decided to take a new opportunity at LinkedIn, another large tech company. What happened to my mindset over the next few years was very strange.

"All Humans Are Entrepreneurs"

As the quarters began to pass, I found myself becoming increasingly risk averse and decreasing self-sufficient. The thought of leaving big tech felt more terrifying after each pay bump/stock refresh. When our company went remote for covid, I realized that I didn't even know how to feed myself after receiving free meals at work for years.

It's not like LinkedIn was a bad company to work for, in fact it was quite the opposite. I truly loved the people and the work I was doing at LinkedIn. But deep down, something still felt off.

In his book The Startup of You, LinkedIn's cofounder Reid Hoffman argues that "every human is born an entrepreneur". But I began to realize that large tech companies (including the one he founded) have a natural tendency to suppress these instincts in their employees as they scale. When you have thousands of coworkers, almost every task can be offloaded to someone else if needed, and unless you're at an exec level or above, you don't really have that much skin in the game.

Suddenly the great perks like free food and gym memberships felt more like a handcuff than an altruistic gift from the company. One by one, I watched as some of my closest friends/coworkers across the industry came to this same realization over the past year and began to hand in their resignations.

I might have ignored these feelings and stayed put had it not been for a few key events over the past year. The first, was publishing my book Modern College . While different than a typical tech startup, publishing a book forced me to practice many of the same skills (design, marketing, planning) and also reminded me how self-sufficient I can be.

The second was a Substack article by Erik Torenberg, called Take Asymmetric Bets . This article helped me realize that there was actually more long-term downsides to me staying put than me quitting to pursue my own ventures.

If Not Now, When?

On June 11th, I made the decision to step away from LinkedIn (and my phenomenal compensation & benefits) in order to embrace my entrepreneurial instincts. However, the decision didn't come easy.

I woke up from an actual anxiety attack on the Monday morning of my final week and was questioning if I had just made a massive mistake. Should I get just one more vest cycle in? What do I even do for health insurance now? These thoughts rattled around in my head as I braced myself to take the leap.

What ultimately pushed me over the edge was the realization that I was in an extremely enviable position. After 4 years on a tech salary and some asymmetric investment bets, I now had enough financial runway to survive on my own for years.

If I wasn't ready to make the jump now as a single 27 year old with financial security, then I wouldn't ever be ready. So I decided to make the jump.

In terms of what exactly I will be starting, I'm still in the exploration stage for now. In the wake of Covid, entire industries have been shifted, and I've been keeping my ear to the ground on a few specific ones. What I do know, is that whatever venture I do decide to pursue, I will be devoting the time and energy up front to make sure I'm solving a real problem for a group of people who need it.

Keep Austin Weird

Once I had made the decision to leave LinkedIn, I realized that I was no longer bound to any one location. For a number of reasons, I've felt like California (especially San Francisco) is not currently a desirable or even safe place to live. I have strong opinions on how it got to this point, but those are probably better to be shared on other platforms. However, I do encourage others to read this Substack article on the California techxodus by Mike Solana, as it hits on a lot of points I agree with.

Rather than criticizing California/SF, I'd instead like to focus on the city I am moving to in Austin. I've long been attracted to the city of Austin, and nearly moved there after my 2 summer internships at Dell (see picture above from my drive down in 2016).

Aside from its great food and music scene, there is also a growing tech and entrepreneurship community that I am excited to contribute to. Some of my favorite memories in Austin, were when I would walk around Capital Factory and talk to anyone & everyone that would give me the time of day.

I also want to do my part to help the city scale in a sustainable and positive way. A lot of cities have made mistakes at the point Austin is at, but I'm optimistic with the right leadership and community support, this will remain one of the best places to live in the country.

I'll conclude by acknowledging how fortunate I am to be able to make these life changes. While I did work extremely hard for these past 4 years, I was also lucky to have the support of many incredibly people to help me reach this point. I truly enjoyed my time working at both LinkedIn and Intuit, and our teams accomplished some impressive launches along the way.

Starting a company and moving to Austin isn't for everyone. But right now, it's what I want to be doing and where I want to be doing it. I'm more excited than ever about the future.

If you live in Austin, please reach out and let's grab a coffee (or beer). Even if you don't live in Austin, the wonderful thing is that LinkedIn makes it easy to stay connected, and planes make it easy to travel. So don't be strangers.

-Alex