Lessons from the “Forrest Gump” of Silicon Valley

How Do You Build a (Relatively) Successful & Varied Career in the Tech Biz?

I get asked this question often by younger folks all across the world, particularly in the last 6–8 years as a “Gray Hair” as 40 something in San Francisco. I firmly believe that the Future of Work and the world is becoming more like the “tech industry” in Silicon Valley than less. Whether you believe that is a good thing or not but it’s happening.

I do NOT feel like i’ve been particularly successful but yet i do feel i’ve had a very interesting and varied career. First as an early employee (Number 18) at a startup that ended up raising 64M usd, then spending 10.5 years at Yahoo! Inc in its glory days, followed by a 6-year stint as a Partner at venture capitalist fund 500 Startups. Varied careers like mine seem to be the norm here in the San Francisco Bay Area which is what makes this place so interesting (and scary competitive).

During this time I’ve pulled out some lessons and principles that I hope will be instructive and helpful for folks starting off, thinking about, or restarting their careers.

1. Try Lots of Things:

The first thing you learn about success from Silicon Valley is the velocity & dynamism of the place. The secret is taking many swings at bat & making a lot of bets. There is a reason so many of the top investors and Startup founders are very big aficionados of Poker.

You see lots of people jumping from startups to big tech companies back to startups.

For example, the average tenure of an employee at a big tech co (Uber, FB, Dropbox, Tesla, Square, Twitter, Netflix) is about 2 years. The days of spending 20 years at a company are over. I recommend trying a lot of things to see what you like, where you can thrive culturally and figure out what you are good at (that the market values). My caveat though is not to jump around every year though, that is just not long enough to see the results of your work at a place.

2. Pick a Growth Company (or 2):

This one is tougher to figure out and why i earned the moniker of “Forrest Gump.” But you should pay attention anytime you see a company on a growth trajectory. Or if you hear the excitement of customers & employees or smart friends talking about it. Present day examples of these high growth companies that come to mind would be Stripe, Fast.co, Superhuman, Epic Games, Notion or Webflow. Or Facebook 8 years ago.

And of course, hopefully you are personally excited by their mission or what they are doing. I found that even if the company does not work out, you meet a lot of very smart people.

3. Give Before You Get. “Paying it Forward Culture:”

The top people are almost always generous with their time, energy and advice. Give before you take. (Don’t be an arrogant A — hole who thinks they are better than anyone else). I am not always successful here but i do legitimately try to do this as often as i can.

This is how I ended up at 500 Startups. I was a volunteer mentor for their core accelerator program for over a year and half. I didn’t do it because I thought i was going to get a job. Being a Venture Capitalist was very far from my mind at that time (i always thought i would go back to being an operator type COO or CRO at Series A+ company) . I did it because it was fun, I had the time and I wanted to give back. I ended up spending almost 15+ hours a week with their startups. I guess they felt guilty and that was probably why they asked me to join and help start their San Francisco office in 2014. (Thank you Dave!)

Always try to be helpful to people below and above you. Morally & cultural this is what makes Silicon Valley work. But the pragmatic reason is that in an environment as dynamic as the technology business, what is a startup today could be a dominant company tomorrow. A poor founder today, is a billionaire tomorrow. It does happen so you never write anyone off here. No where else in the world do we love a comeback story quite like in Silicon Valley.

4. Think About Your Reputation & Practice Long Term Thinking:

As Warren Buffett says “It takes 20 years to build a reputation and five minutes to ruin it. If you think about that, you’ll do things differently.”

Everyone talks about it but in my 20+ years here in Silicon Valley, I am continually surprised by the bad behavior of people and extremely short term thinking that happens. If you are good at what you do, have a reputation for doing right by people whether you are a company or person. This will precede you wherever you go or whatever you do in Silicon Valley.

5. Stress Importance of Relationships & Network (and Power of the Back Channel):

What makes Silicon Valley as well as any other industry work is the tight relationships and networks that span geographies. School and company alumni operate on this. There is the most famous Paypal Mafia but people forget about the very extensive ex-Yahoo!, ex-Facebook, Xoogler, or ex-Ebay or ex-AirBnB or ex-Uber Mafia that spans across Silicon Valley.

This is how you get new opportunities and get referrals and feedback on individuals. This is also how you find out about people’s true reputations during the inevitable reference check.

6. Optimize Learning over Earning (ie. Chase Curiosity and not Monetization):

Be a Missionary, not a Mercenary. Mercenaries don’t last in the long run in a place like Silicon Valley. What I optimized for every role I chose was “would I learn in this position and company?” Would I be surrounded by super smart people who would raise my standards?

“You are the average of the 5 people you spend the most time with.” This has always worked for me.

Of course there are situations when you do need to think of the money. But for me, In those few occasions when I did choose things mainly for the money, it never worked out well. Probably either because I was not fully interested nor was I fully committed.

7. Stay Longer and Be Prepared to WORK A LOT:

I see so many people jumping around every year to a new company or new opportunity. I know I mentioned taking a lot of bets but you also have to spend at least 2–3 years at a place as this is how long it takes to 1) make an impact on the business

2) seeing the results of what you are working on. This is how you learn the trade.

I should also note that while I worked at Yahoo! for 10.5 years, I had 5 different roles across different groups while there. So it was varied and did not feel stale.

Sorry to disappoint you but you cannot “4 Hour Work Week” this, especially if you are early in your career (or if you want to achieve excellence in a new role or something completely new to you). When I was at Yahoo! and 500 Startups, I’d work 80–100 hours a week and it did not feel like work. I thoroughly enjoyed the work so much, it was almost every night Monday to Thursday that I would get a call from my wife after 900 pm asking me when I was coming home. (SORRY :() & i should note i missed a lot of my young daughters life which is the only deep regret i have in my life today).

8. Invest in Yourself:

I was so obsessed with getting better and learning about how to do the job, I’d spend time in the evening and weekends reading and watching videos, talking with friends who were investors or renowned operators and learn from them. At Yahoo! this was driven by insecurity and fear of losing my job in the aftermath of the Dotcom Bust. I also felt very behind everyone around me there. They were smarter, had more relevant experience and were more credentialed than I was (boy so MANY Stanford MBAs at Yahoo!). I definitely have some level of OCD which helps here. But I was legitimately interested in the subjects, and over time they became an obsession for me.

When I joined 500 Startups in 2014, i found some good mentors outside the Firm who were extremely helpful to me (thank you Mike & Tim). I read and watched everything on the art of Venture Capital and how it worked. I was also lucky to be at 500 during that time as it gave me many opportunities to practice investing (i ended up doing over 400 seed deals when i was there which i will be eternally grateful about).

9. BE Interesting (and be Opinionated & Vocal):

In my sabbatical aka “Fallow Years” between Yahoo! & 500 Startups, i met a lot of interesting people in Silicon Valley after being cocooned in the comfortable world of Yahoo! digital media/advertising. It’s relatively easy to get first meetings but hard to get follow up ones. I did this because i had 1) nothing to sell 2) i was not looking for a new job 3) nor was i trying to raise money. But I had built a solid experience, a decent reputation and spoke my mind as I saw things whether it was popular or not. This is very much valued by most senior accomplished people whether they were senior VCs or Business Execs or Startup Gods where people (especially in California) do not speak their mind for fear of offending anyone. So I always got invited back. It does pay to “Speak Truth to the Power.”

I hope the lessons I shared will be helpful for anyone who is interested in surviving and thriving here in Silicon Valley. I cannot guarantee you will get “Rich” following these principles but i do think they will help you build a really fun and impactful career in Tech.

I consider myself very lucky, having built a varied career that has challenged me intellectually, put me in the circle of so many accomplished individuals at the top of their game and given me opportunities to travel across the world. I’ve had such a fulfilling and fun time over the last 21+ years here. That is why I have no problems claiming the title “Forrest Gump of Silicon Valley.”