How Ruben Harris Used the Power of Stories to Break Into Startups

Disclaimer: This is my own personal podcast summary for a podcast which was originally produced by Free Code Camp titled: “How Ruben Harris Used the Power of Stories to Break Into Startups”

Introduction To Episode

Quincy Larson interviews Ruben Harris of CareerKarma, a social network for people interested in attending coding boot camps. He also hosts the Breaking Into Startups Podcast.

Ruben just finished Y Combinator, a startup accelerator, where he and his team raised the first round of venture capital funding.

Ruben shares his insights on coding boot camps. He also shares what he learned going through Y-Combinator.

Ruben on Twitter
Quincy on Twitter
Link to Episode

Listen to The Original Episode


“I didn’t see my background as a detriment. I saw it as a form of empowerment and I really valued being different and I sawy that as a super power.” Ruben Harris

“Chicago is a city that’s big, but you can wrap your head around it. You can rise up and reach your goals.” Ruben Harris

“No one can compete on being you than you. Most of life is a search for who and what needs you the most.” Naval

“You’re either at the table or on the table getting eaten.” Ruben Harris

Key Takeaways

Ruben on Life in General

  • Being polite and being a gentlemen has been a key part of Ruben’s upbringing.

  • He’s always been around people who are entrepreneurial and people who believed they can achieve things from all walks of life.

  • When you learn how to play an instrument, when you learn about music, you learn a lot about stretch targeting.

  • Stretch targeting is a goal that pushes you to achieve it.

  • Accepting and valuing yourself is crucial.

  • The ultimate calling is to serve others in life.

  • Introduce your children to difficult things early on. They won’t realise that what they’re learning is actually hard.

  • Finding value in things that you don’t like and doing them anyway is key; then reflecting on it and understanding what the value was.

  • Ruben’s mother emphasised on the importance of finishing things that you’ve started.

  • A small intimate group of friends will stay with you throughout your life.

  • Small short goals, mentorship & guidance are key.

Ruben on Breaking Into Startups

  • Ruben used online resources to teach himself investment banking

  • It’s all about people.

  • Leveraging people to get the interview or anything in life is key.

  • Understand what the minimum social skills are in order to tell your story.

  • "Chicago’s big but you can wrap your head around it."

  • "The way how you rise is through your non-tangible skills".

  • It’s all about getting your personal story nice and concise and then being able to communicate this to people effectively.

  • To get into investment banking, Ruben had to explain why he wanted to become an investment banker.

  • Answer your WHY. You want to give an answer that’s deeper than money.

  • Ruben wanted to become a successful musician, but a lot of musicians lack business skills, so in order to become successful he had to learn business and he learned that as an investment banker you learn a lot about business. And that was his story.

  • At the end of the day it’s about the chemistry.

  • Coders on FreeCodeCamp who are applying for the same job and all have the perfect resume and the perfect credentials can only differentiate through one thing and that is themselves.

  • What makes you different is who you are!

  • What is normally weird to people when they’re younger or what they were embarrassed about, a lot of times, becomes their super power when as they get older.

  • Quote from his colleague: "If you help people put food on the table, everything else will come."

Ruben on Starting A Business

  • Ruben always wanted to start a business.

  • Ruben and his team gained experience by working at different companies and learning from the experiences and how these companies ran to then take that knowledge and apply it to their own business.

  • The fundamental two questions from investors when you raise capital: A) Who’s technical? and B) How do you know each other?

  • One of the biggest reasons companies blow up is because the co-founders blow up.

  • Think of it as a relationship. Get to know your co-founders on a fun level first. Share your philosophies. Once they align, you have found fit.

  • In order to get ahead in business (& life) you need to understand trends

  • Ruben wanted to create resources that are actionable so people can elevate themselves.

Ruben on the Future of Education

  • "(Coding) Bootcamps are the fastest way to get a high paying job in less than 12 months."

  • The problem with online learning (MOOC): it lacks accountability and motivation. People don’t finish online learning programs.

  • The digitak skills gap is a real thing, hence, there are so many open jobs. There are people out there who are talented that companies are unable to find.

  • In the USA, 44% of college grads are unemployed or under employed.

  • Colleges will soon realize that 2-4 years education are too long.

  • Accelerator programs measured on outcomes are here to stay.

  • Colleges need to be aligned with the needs of the work force.

  • Partnerships with bootcamps and colleges will increase.

  • Income Share Agreements show signals that they are interested in the outcome of their students.

  • Ruben first got rejected from Y-Combinator, because he didn’t know how to communicate well.

  • His first pitch wasn’t laser-focused on the real value prop of CareerKarma.

  • 50% of engineering interviews fail because of non-technical reasons!

  • Speed of iteration, experimentatios & mentorship are key.

  • Understanding that everybody is lost helps dealing with Imposter Syndrome.

Ruben on Having the Right Mindset

  • There are always going to be curve balls, there are no straight aways.

  • You have to be mindful of things that can you throw off your path.

  • You have to be mentally sound. Keep your head in the game.

  • You never want to get comfortable. As soon as you get comfortable that’s your body telling you to push harder. Only that will give you growth & growth is life.

  • Sales & marketing roles & education will be getting stronger.

  • The only way to level up and escape automation is to do some form of education, e.g. a bootcamp.

  • Employer sponsored education & apprenticeships are becoming more and more important.

  • Employer run schools to retrain existing employees.

  • Credentials don’t matter as much as portfolios.

  • Always embrace learning.

  • What you do doesn’t define you. What kind of school you went to doesn’t define you. You are who you are.

  • Pain comes from the same spot where power comes from. If you dig deep enough to situations that hurt you, you can really get power out that.

Action Items

  • Start building your network and start building relationships early on.
  • Define your WHY and your life story to land your dream job.
  • Always embrace learning. Never stop.
  • Embrace your own personality and accept that you are who you are and that is what will set you apart.


Breaking Into Startups (Podcast)

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