#MyMomentum | These 4 Lessons Propelled Me from Thiel Recruit to VC Fund Founder

This article was posted as part of the MyMomentum series on Looksharp. If you have a career path story you want to share, tweet it at as using the hashtag #MyMomentum. 

In the late 1990s, I was a Chemical Engineering major at the University of Colorado with a minor in business. I’d taken the business minor at my father’s suggestion, and it wasn’t until the end of my undergraduate career that I realized, out of the three core elements I’d studied at CU (chemistry, math, and business), I actually enjoyed math and business the most.

I applied to the Operations Research departments at various grad schools because OR seemed like an interesting area that applied mathematics to complex business problems in various fields, including finance. I was accepted into Stanford’s OR department, which now goes by the name of Management Science and Engineering, and decided to head to Palo Alto, California to pursue a Masters Degree.

When I got to Stanford, I noticed that almost all of my classmates had some kind of prior work experience, which seemed to give them a lot of context around the material that we were learning. It felt like they were getting more out of the educational program than I was, so I decided to get a job to gain some experience. I took a part-time position as a Financial Analyst at a company called Confinity, which was creating a system to allow people to beam money to each other on Palm Pilots.

It’s worth noting that during my initial breakfast meeting with the CEO of Confinity, he asked me what books I had read that summer, and later joked that my reading list was one reason he hired me.

Professional Life Lesson #1: Be Yourself

During my initial interview, I was so concerned about whether I had taken the right courses or done the right projects. In the end, what this employer liked most was what my reading list said about who I was. I’m sure it helped that I had gotten good grades and done interesting projects as an undergrad, but a lot of other applicants had too… So those things didn’t really set me apart.

On my first day at the company nobody knew what I should do. A Chemical Engineering major who knew a little about business? It turns out that I did have one really valuable skill at that time: I knew a lot about Microsoft Excel. One of my undergraduate professors, Dr. David Clough, had insisted that we all learn a lot of the more powerful (and sometimes obscure) features of Excel. When I started working at Confinity I was kind of a whiz at it, so they asked me to start tracking data, distributing metrics, building financial models. Because I was so good at it I could do the work really quickly, which meant I had time to then sit in on meetings where senior executives were discussing the data I was preparing. That kind of exposure was incredibly valuable for me at the time, because I got to learn how people communicate in a business setting, how they share and debate ideas, and how they work toward actionable conclusions.

Professional Life Lesson #2: Know Your Hard Skills

In most entry-level positions, you are doing tasks that require hard skills (proficiency with a software program, etc.). If you are able to do these things quickly and accurately, your boss will (at least they should!) allow you to use the remaining time in your schedule to attend meetings and begin learning the soft skills of doing business.

After several months, I was increasingly impressed with the caliber of people at Confinity, and the company’s growth as a whole. They were impressed with me too. The CEO offered me a full-time position that would require me to drop out of my MS program. Drop out of Stanford? Was he serious?! I thought about it and weighed my alternatives, and I confirmed with Stanford that if things didn’t work out with the company I could go back to finish my degree. I eventually decided that the downside was limited and took the job.

Shortly after this, Confinity merged with a company called X.com and the combined entity changed its name to PayPal. The three years that followed were a whirlwind of excitement, with incredibly long work hours and an unbelievable amount of learning. I eventually grew into an important role in the company’s finance team and got a first row seat in an Initial Public Offering process and then the acquisition by eBay in late 2002.  This learning and exposure set me far ahead of my peers in similar roles, and really launched my professional finance career.

Professional Life Lesson #3: Take Calculated Risks Early in Your Career

I made the decision to leave Stanford and work for Confinity at a time when my downside risk was really quite limited. As you get older and advance in your career, it becomes harder to take risks like this because you have more responsibility: family, financial commitments, as well as other things that start to constrain your alternatives.

I met and worked with an incredible group of people at PayPal, many of which went on to create globally important companies after they left. I feel honored to have been a part of that group at that time, and many of us still collaborate on business projects to this day. Through this network I have been exposed to some amazing ideas and given opportunities to work on projects and companies that are literally changing the world. Remember that CEO who liked my summer reading list? That was Peter Thiel, who is now a global iconoclast and one of the most successful venture capitalists of our day. Peter has been an important mentor to me and has had a major impact on my life and career. He is the one who, after seeing what I had learned and contributed in those early years at PayPal, eventually offered me my first role as a Chief Financial Officer (at Palantir Technologies).

Professional Life Lesson #4: Don’t Over-Plan Your Career Path.

You really don’t know what opportunities are going to be presented to you, at what times, and who will present them. If you over-plan your career you may miss out on unexpected opportunities that cross your path, instead of recognizing when you are in the right place at the right time and seizing them.

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Jason Portnoy

  • Zabrina Janda

    #1 What were some of the books on your reading list?
    #2 Excel = great skill to have. The main reason I got my current job is because I know Excel.
    #3 I work for a larger company and wanted to know if there was an appropriate way to get exposure the way you did. Ex: sitting in meetings or listening to other related conversations.

    I’d really appreciate any advice! Thanks for sharing. -Z

    • Jason Portnoy

      Hi Zabrina,

      1) Is hard to remember all of them. I was traveling in Europe that summer and had a lot of time on trains, so I read a bunch of books. Here are the ones I remember:

      Lord of the Rings trilogy (started during final semester, finished in summer)
      The Art of War
      For Whom the Bell Tolls
      Tao Te Ching

      2) Nice 🙂

      3) In most workplaces you have to manage your learning curve actively. If you want more esposure to opportunities to learn I think the first step is talking to your boss about your goals and working together to figure out what meetings, talks, etc. might be appropriate for you to listen in on. They should be able to help guide you in a way that makes sense for you and the company.

      Hope this helps. If you are reading blogs like this and active enough to ask these questions then my sense is that you are already ahead of the curve. Keep it up.