Weston Ludeke

Joining another startup!

Published (updated: ) in misc.

The Streak team!
The Streak team!

Five years ago my wife and I made the long move out to Silicon Valley from Houston settling in Mountain View, California. After returning home to Houston in 2013 I joined my second startup, Streak.com, earlier this year!

The Hustle

Back in 2011 I moved to Silicon Valley with zero connections and hustled my way into a job at a small ad tech startup called isocket thanks to meeting the author of an awesome blog post I read on Hacker News, Jason Shen. Jason was leaving isocket to join Y Combinator’s summer 2011 batch as a co-founder of RideJoy and he introed me to isocket’s CEO/founder John Ramey, who eventually hired me as Jason’s replacement.

Working at the isocket office in Burlingame I would frequently ride the CalTrain to work. Each time I took the train I would walk down Dana Avenue, past the Hacker Dojo, and past the Y Combinator offices on the corner of Dana and Pioneer Way on my way to the station.

The YC offices

I’ve been a daily Hacker News reader since 2010 and Y Combinator has long been an inspiration to me. Walking to the Mountain View train station I would often think about all of the entrepreneurs working on awesome innovations inside those walls. AirBnB, Reddit, Dropbox, and Stripe are just a few of the hundreds of startups that went through the YC program that have disrupted industries and simplified life for millions of users around the globe. Walking by those offices I would dream about one day working for a YC startup and perhaps eventually starting my own company in the future.

View from the isocket office rooftop, looking out towards the Burlingame CalTrain station
View from the isocket office rooftop, looking out towards the Burlingame CalTrain station

The Road Less Traveled

After my position at isocket was eliminated in 2013 and moving back to Houston, I worked some different jobs while I tried to figure out what I wanted to do next. Even though I was initially burned out on startups at the end of my first startup experience, over the coming months I had plenty of time to reflect on my two years living and working in the Valley.

What’s fun about startups is they are vastly different than normal corporate jobs because they’re not yet successful businesses and may or may not be profitable. Startups move at lightning fast speed and I like to think it’s a 1:10 ratio: 1 year in startup life is equivalent to 10 years in the typical large tech company.  Startups and the products they make change rapidly. But working for a startup also comes with a big degree of risk, but without it, there’s no personal growth.

Some people aren’t built to rock the boat and need a certain deal of certainty in their lives. It took me a long time to realize that I’m not built for that certainty: I need and thrive on chaos and constant change that startup life provides. I can’t do the same thing over and over again every day: I need to be learning every day and constantly challenging myself to improve.

When I moved back to Houston I tried to work regular jobs just for a paycheck and not trying to find something that I thought I would really enjoy, but eventually, something kept gnawing at me: I was restless because I wasn’t challenging myself to get better every day in my job. That Bill Burr quote above always serves as a reminder to me: We only have one life to live and we don’t get a do-over, so we might as well live the life we want and not the life that other people live or the life that other people think we should live.

Just When I Think I’m Out

Once I realized I wanted to join another startup, I realized the best option for me was to try to find a remote customer support position since my wife and I were happy in Houston and not ready to leave behind our family to head back to SF (and SF isn’t exactly cheap). I decided to focus on support because support workers at small startups work closely with the founders and engineers in communicating product feedback and documenting bugs. I spent nearly two years and sent out over one hundred extremely targeted resumes and did some freelancing on the side to help bolster my resume.

Eventually, I met the awesome folks over at Streak.com and they hired me back in April. I went out to work in their San Francisco office for two months to get to know the team and learn the product. I hadn’t been back in SF since we moved three years ago so it was an incredible rush to be back in the Bay, surrounded by other startup geeks like myself.

Interestingly enough the Streak team was part of the same, summer 2011, Y Combinator batch as RideJoy.

Right At Home

When I joined Streak I loved the random conversations colleagues would have about cool stuff like the future of virtual reality and companies like Oculus. As a sports fan, I can chime in with how Stanford’s football team is pioneering the use of virtual reality to train their players and nobody looks at me like I have three heads.

There’s a saying that goes, “You are the average of the five people you spend the most time with” and I think it applies to careers as well. If I want to be on the forefront of technology and startups I need to surround myself with like-minded people.

The Future

I’m fascinated by technology and how web development works and I’ve been working hard picking up some front-end web development skills. If I’m the smartest person in the room, from a technical perspective, then I need to find another place to work because I’ll likely not be learning anything.

Sometimes you have to work many jobs in different positions and/or in different fields to realize exactly what you want out of a career. I’m glad I’ve had the experiences I’ve had to keep me focused on exactly the type of future I want. I plan to write even more over the coming months about why I enjoy startup life and the differences between startups and corporate life. I’m not saying I’ll never work in a large company, but likely only for companies that were formerly startups themselves which are now mid-sized companies or larger like the Googles and Facebooks of the world.