Breaking Into Startups

From Cello to Investment Banking to AltSchool

Breaking into Tech with a “non-technical” background is hard. The same barriers that exist in Finance also exist with Startups. This post lays out the specific action steps that I followed to make this transition. No words can express my deep respect and appreciation for everyone that I mention (below) and the countless people that helped me during this process.


For those of you that don’t know, I got laid off from my first job in October 2012. After 2 months, I got an offer to be a 2nd year Investment Banking Analyst in Atlanta. I accepted and within 5 months, I was promoted to 3rd year Investment Banking Analyst (Chapter 2, more on this later).

Stay hungry, save money, and leverage online resources

Although my girlfriend was still in Chicago, I decided to move to Atlanta so that I could live with my parents and take advantage of the higher salary.

Like most investment banking analysts, I started thinking about exit opportunities in the middle of my 3rd year by doing private equity interviews and prepping for my MBA.

Going through the motions made me realize that I wanted more than a higher salary, so I opted out and searched for alternatives on social media.

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

My focus on San Francisco began when my tweet caught the attention of Balaji Srinivasan, Andreessen Horowitz’ Newest General Partner.

Where it all started (December 9-12, 2013)

Naturally, I was not going to let this type of opportunity get away from me. So, I kept tweeting things that I was passionate about, but were also relevant to him. He continued to respond with retweets that in turn led to Direct Messages, more venture capitalists (VC’s) following me, and questions about my background.

The Spark: Resume Request, Direct Messages, and more Retweets (December 2013)

Act on the advice you’re given

After some time, he shared his passion for education. Then, he said, “we should get you into tech.” To start, he told me to read all of the Suggested Reading links in his Startup Engineering MOOC on Coursera. Startup Engineering is a sequel to Peter Thiel’s CS183 course and it completely changed my perspective on what I needed to do next in my career.

Figure out how you’re going to add value

My Aha! Moment came when I read the notes for Peter’s 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.”

I immediately knew that this is where I was going to add the most value at a startup. After a few opportunity suggestions from Balaji, I started focusing on roles related to or centered on Sales, Marketing, and Business Development.

Network to build a personal board of directors and open doors

Just because someone connects with you on social media doesn’t mean they’re your friend. While online relationships can be broad and deep, they’re not quite like human relationships. Silicon Valley is relationship-driven and I wanted a group of people that I could consult with regularly for advice and feedback (Personal Board of Directors).

With that in mind, I decided that I had to plan my first trip to San Francisco and meet Balaji in-person. Since my cousin was graduating from Berkeley in May and my girlfriend had never been to California, I killed 3 birds with 1 stone and planned my visit around my cousin’s graduation date.

As I was preparing for my trip, I noticed that Geoff Lewis was also following me on Twitter. I was really excited about many of the companies he invested in on behalf of Founders Fund and loved an article he wrote while he was the CEO of Topguest. The article was called how to score massive meetings for your startup and I liked this template because I recognized that the most successful people in Business Development maintain a set of “pick up the phone” relationships with decision makers in companies that allow them to sell to end customers in a scalable way. Instead of sending him a Direct Message, I did my research (read his blog), sent him a cold e-mail following his template, and setup a time to meet in May as well.

Bloomberg Interview on Income Inequality (July 2014):

The last meeting that I setup for this trip was with Kanyi Maqubela from Collaborative Fund. The types of problems that I wanted to focus on were further down Maslow’s Hierarchy of Needs, so it was important for me to get closer to a personal board of directors that was also passionate about mission-driven companies. He was receptive to my cold e-mail and agreed to meet with me.

Maslow’s Hierarchy of Needs (e.g. MOOCs / edtech, shared services, agtech, bitcoin, drones, VR, quantified self, etc.)

In the interim (December-May), I established executive-level relationships with startup companies by leveraging my connections in Corporate Development (BMO alumni). After doing some Due Diligence (Stage 1 and 2; using public information) on each company, I cold-emailed the decision maker and made strategic introductions to one of my contacts that could solve his or her problem in a way that was mutually beneficial.

I thought about it like this: If I didn’t get a response to an e-mail, it wasn’t meant to be or it wasn’t the right time. The only thing that I had to consistently do was send 5 personalized e-mails to influential people everyday. To me, those e-mails were like sales pitches and ~80% of my “sales” came from ~20% of my efforts.

Another way that I thought about it was:

“Doing the unrealistic can be easier than the realistic because there’s less competition for the bigger goals.”

Position yourself for serendipitous interactions

One day, my girlfriend and I were listening to NPR in the car and she told me to pay attention. The radio host explained that about a dozen mansions in the Bay Area were being leased to groups of young entrepreneurs and run as communal living spaces.

I recognize the value of positioning and the power of serendipity, so I sent a request to book a room in a place called Agape on Airbnb. I read about Agape in SF Gate and knew that amazing things would happen if I stayed there. The host promptly responded saying that he also grew up in a classical family, his mom was a cellist, and I was a good fit.

As soon as we arrived, we decided to buy groceries. Unbeknownst to us, an Agape resident prepares family dinner every Monday and the person responsible for it had forgotten to do it that week. I saw this as an opportunity for us to get to know our hosts better and offered to prepare the meal instead after my friend Montrey suggested it.

Agape Family Dinner (May 13, 2014)

We said grace and Justin Rosenstein asked me why I was in town. He had just gotten back from presenting his “Do Great Things Speech” at TechCrunch Disrupt in New York and offered to help me. I was grateful because I believed in the “Helping Humanity Thrive” mindset.

Helping Humanity Thrive Venn Diagram

Identify the people that know each other in your network

My meetings with the VC’s went well and I learned that Justin’s brother, Perry, went to school with Kanyi. Kanyi and Geoff also knew each other and both offered to make introductions to contacts in their portfolios. Geoff and I spoke over the phone because he had to reschedule, but we agreed to meet in person after I moved to the Bay Area.

Craft your story and don’t talk about it, be about it

I quickly learned that people in tech don’t like investment bankers that much because they think that they’re just Finance guys that crunch numbers all day. With that in mind, my goal was to clarify that an investment banker is essentially a B2B salesman with deep industry knowledge and a strong quantitative background. In case that would not convince them enough, I decided to take a Computer Science class online from Stanford to learn how to communicate with engineers more effectively. I also wanted to prove that I could establish strategic partnerships and raise money quickly, so I helped organize Atlanta’s first Healthcare Hackathon with a startup and raised ~$40,000 in collaboration with its leadership team.

Actions Speak Louder Than Words

Take calculated risks and don’t be afraid to use your savings

I realized that finding a job long-distance would be difficult, so I asked Agape if I could stay there for a month in September. They agreed, so I bought a one-way ticket.

Risky One-Way Ticket (September 5, 2014)

Know what you want

The type of company that I wanted to join had to have the following criteria:

  1. Team: Founders that have done it before
  2. Culture: Ethical, humble, and personable
  3. Early Stage: Series B or below
  4. Top Tier Investors: Due Diligence that I could trust on top of mine (ideally backed by Founders Fund, Collaborative Fund, and a16z)
  5. Market Opportunity (Size): Solving a problem that the CEO also has
  6. Full-Stack Startup: A place where I could learn and add a lot of value

Build a support system (to help manage your psychology)

On the plane, I read about managing my psychology and learned that the quickest way to happiness is gratitude (Peak and Emotional Equations by Chip Conley are great if you’re interested). However, I still needed a support system. I wanted to be close with other minorities without an Ivy League background that had successfully built a network in Tech. I knew that Diversity was an issue, but Naithan Jones and Divine figured out a way.

Diversity issues in Tech (Source:
Gender Gap in Tech (Source:

They both followed me on Twitter, so I sent them a couple of Direct Messages to set up meetings during my first two weeks.

Before and After meeting Naithan Jones
Before and After meeting Divine

Real recognized real, and we hit it off immediately. After my meeting with Nait, he told me not to worry about anything and invited me to a dinner hosted by Erik Torenberg from Product Hunt. Nait emphasized that I had to meet this guy named Chris Lyons, Deputy Chief of Staff at Andreessen Horowitz. Chris and I clicked because he’s also from Atlanta and bought a one-way ticket to San Francisco as well. Chris offered to help me and we all started sticking together. After that, Nait introduced me to Ben Horowitz and Dori Caminong at Glide Memorial Church. Dori introduced me to Ben’s wife, Felicia, and they both kept me updated on ways that I could help them build bridges between tech and the community.

Surprise Birthday Party for Nait Jones (Left to Right): Santi Yago, Ruben Harris, Felicia Horowitz, Chris Lyons, Nait Jones, Ben Horowitz, and Danny Bocanegra (December 6, 2014)
Event: A GLIDE Talk with Van Jones and Jim Gilliam (Left to Right): Dori Caminong, Nait Jones, and Ruben Harris (October 29, 2014)

Take meetings that may seem off-topic

During that first week, my friend Josh Kahn also introduced me to his buddy Alex Regenstreich. This meeting was not supposed to be related to business at all, but I noticed that he knew Jane Yu, the Head of Partnerships & Philanthropy at AltSchool. AltSchool was on my list because it met all of the criteria above and lucky for me, Jane and Alex interned together at Google.

Don’t hesitate when it feels right

Jane and I met for coffee on Monday, September 22. It went very well, but she said she had no opportunities on her team. She offered to refer me to any other roles that I was interested in and I thanked her. That Friday, I got another e-mail from her asking if I would be interested in working on a paid project with her over the next 5–6 weeks. Without hesitation, I said yes and started that Tuesday (September 30). I was really happy about that because my girlfriend’s birthday was on September 24 and we had been praying for a job that we would be able to celebrate together when she came to visit me that weekend.

Alexa’s 25th Birthday (September 29, 2014)

What’s even more crazy about that is my rescheduled meeting with Geoff was on Wednesday (October 1) and AltSchool is a Founders Fund portfolio company. During that meeting I asked him to be my mentor and we agreed to quarterly check-ins.

My first time in the Founders Fund office (October 1, 2014)

Work hard and over deliver

Two weeks later, the AltSchool project was completed and my contract was extended. I eventually earned a full-time position on the Growth Strategy team and moved into a new apartment.

Just to show you how God works, on my way to my new job, a man was trying to get my attention and I recognized that he was Charles Hudson, Partner at SoftTech VC. He said I looked familiar (I had e-mailed him a long time ago) and asked me if I lived in the area. We found out that we were neighbors and that led to a conversation about him becoming a mentor. What are the chances that I would have two African-American Venture Capitalists that are well-known in my circle (Charles and Kanyi)?

Suffice to say, I’m grateful. Grateful for Jane, my family, Alexa’s family, my mentors, and everyone that has supported me during this process.

2013–2014 was about creating online relationships and making them real. Stay tuned for what’s about to go down in 2015!


AltSchool is hiring:

Feel free to e-mail me if you’re interested:

Rubén A. Harris (@rubenharris on IG, Twitter, and Snapchat)