How Ruben Harris broke into tech with cold emails and Twitter.

Lessons.

  • Learn in your 20s, earn in your 30s. Spend your early years building a specific skill stack that you can then compound and monetize.

  • Remove “I can’t” or “I don’t like” from your vocabulary. If you only do things that you like to do then you aren’t really growing.

  • Consistency. Whatever you are trying to grow and improve, do it well and do it consistently.

Frameworks.

  • Don’t be afraid to reach out to potential mentors on Twitter.

  • Learn how you can add value.

  • Network to open doors.

  • Take calculated risks.

  • Build a support system.

Insight.

  • If you want to see what’s happening next. Ruben recommends that you closely follow what TikTok is doing and take it very seriously.

Ruben’s 20s.

Ruben Harris is the founder and CEO of Career Karma, which matches students with the best coding bootcamps. He also has a podcast called Breaking Into Startups with a social reach of ~3 million people, 200,000+ downloads, 10,000+ monthly website visits.

Ruben spent much of his youth as a professional Cellist, playing in prestigious venues like Carnegie Hall. While in college, Ruben worked at a classical music radio station and organized parties. Also in college, Ruben grew to love writing and launched his first blog called The Social Reformer and was an early recognizer of the value of social media, namely Twitter — a platform for which he claims to be one of the first 100 users and now amasses a following of ~60K.

For his first job out of college, he landed a much sought-after position as an investment banking analyst, but that didn’t come without first cold emailing over 1900 potential employers. His time in investment banking gave him an intensive education in business that he still leans on while running his company.

After a few years in investment banking, Ruben was looking to break into tech. However, he had virtually no network or technical know-how and dealt with tech’s unfavorable view of ex-bankers, making this a problematic career shift.

Ruben’s first entry into tech came after a16z partner, and former Coinbase CTO Balaji Srinivasan retweeted and subsequently followed him.

Ruben did not let this relationship go to waste, eventually turning the first online interaction with Srinivasan into a series of DMs and then an in-person meeting.

While preparing to meet Srinivasan, Ruben noticed that venture capitalist Geoff Lewis of Founders Fund was also following him on Twitter. He reached out via cold email and added him to the list of tech industry leaders he was to meet upon his initial trip to San Francisco. All in all, entirely through cold outreach, Ruben Harris was able to meet and build relationships with some of the tech industry’s most elite.

In addition to building out his personal board of directors to include the likes of a16z’s Nait Jones, Ben Horowitz, and the rapper Devine, Ruben began to zone in on the specific way that he would add value to a startup.

His big realization came upon reading notes from Peter Thiel’s CS183 class on distribution.

“People understand team, structure, and culture are important…but for whatever reason, people do not get distribution. They tend to overlook it. It is the single topic whose importance people understand least…Even if you have an incredibly fantastic product, you still have to get it out to people. The engineering bias blinds people to this simple fact. The conventional way of thinking is that great products sell themselves; if you have a great product, it will inevitably reach consumers. But nothing is further from the truth.”

Ruben decided that the way he was going to add value was through sales, marketing, and business development. Ruben subsequently landed his first job in tech on the Growth Strategy team at AltSchool.

Ruben wrote a viral blog post documenting his entire journey into startups that also includes how he left for San Francisco on a whim with a one-way plane ticket and how he spent his first month in a communal living space for entrepreneurs called Agape.

Takeaway

The major theme Ruben displayed time and time again was sheer tenacity. One example of this was sending five personalized emails to influential people every day in the form of a strategic introduction to one of his contacts that could solve his or her problem. He did not care if they responded or not, only that he stayed consistent in his effort.