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Wednesday, September 11, 2019

10 Career Lessons from 10 Years in Silicon Valley

I published this first on LinkedIn. 

Ten years ago this month I drove across the bay bridge in a full-size truck with everything I owned in the back, to start my first post college full-time job. I was a bright eyed, recent BYU grad, that did not know hardly anything about San Francisco.

Fast forward to the present and I feel extremely fortunate to have spent my whole career thus far in the bay area, working with many wonderful people at some pretty amazing companies. I recognize that it has been a privilege to have a career that I've enjoyed immensely.

There are a few lessons I've learned over the last 10 years that have really stuck with me and I wanted to share them here. Some are unique to Silicon Valley, some are not, but I hope you can enjoy what I've learned.

You're smarter than you think. I remember the first time I was in a meeting with a fellow marketer that went to Stanford. I was extremely nervous, to me, he might as well have been able to read my mind. I'd never met anyone that went to Stanford. I was extremely intimidated. A few months later I realized that he was of course very smart, but I realized I could keep up. I think that is so often the case, we think others are smarter or have some talent we don't have, but it's often not the case.

Work is important, but not THE most important. It may seem strange that I learned this in a place that is known for promoting the "hustle". People here do work hard, but I've also seen so many examples of people that can have a ambitious career and still take care of the things in their lives that are most important. It's not easy, but I'm grateful for mentors that have shown me it can be done.

Find managers who believe in you.
Looking back, almost all my managers have encouraged me, believed in me and given me opportunities to grow. If you are not in that situation, my only advice would be to find a way out as soon as possible.Your career will be greatly limited under a manager that does not believe in you.

Dream big. I think the biggest advantage of Silicon Valley is people here believe they can do crazy things and they just do it.

Find managers who tell you the truth. The most rapid personal career growth that has happened to me is when I've had managers who have told me the truth. At first it was uncomfortable and hard, the millennial inside of me would sometimes prefer constant praise, but with constant feedback you can learn so fast. If you're manager is never correcting you, you're not growing as fast as you could.

Manage your reputation like your career depended on it. The world is small, especially in Silicon Valley. Back channel reference checks are happening constantly, word gets around. Your reputation is either helping you behind the scenes or working against you. Work hard, treat everyone with respect and build those up around you and you should be fine.

Trust your gut. The first few years of my career I'd see a decision be made or something happening that deep down in my gut, I thought it was the wrong decision or disagreed with. I rationalized that they were more experienced or smarter, but hindsight is 20/20. In those situations, I now know to trust my gut and bet on myself. I remember getting that advice from the CEO of a start up I worked for in college, but did not have the confidence to follow it for the first few years of my career.

Be a missionary not a mercenary. If you are lucky enough to have the choice, I've found that I've felt much more fulfilled when I really believe in the product, the mission and the leaders of the companies I've worked for.

Leaving good in pursuit of great. In terms of roles and companies, I've seen that the people that push themselves when they get comfortable and leave a good job or role in pursuit of greater opportunities are happier. Companies in Silicon Valley have become masters of helping you feel comfortable and fulfilled in jobs that maybe don't push you to your full potential.

There is power in diversity. I truly believe that I've learned more being surrounded by a variety of people, ideas and background.

Thank you for reading and humoring my walk down memory lane.

Saturday, September 7, 2019

When to Sell Your Company Stock

For the last 2.5 years I've been working for Zoom, which before April 18th of this year was a privately held company. Before Zoom, I had always worked for large public companies. Now that we are public I've been doing a lot of research about when to sell company stock. Prior to my current gig, anytime I had company stock I was using it to pay for grad school, pay off debt or build an emergency fund. This is the first time that I have company stock and all those things are behind me.

I'm fortunate to have many friends and mentors who have gone through this before and I've been relentlessly bugging them and getting their advice. I've also been doing my own research linked out below to some of the best resouces I've found on the topic. I've always felt the best financial advice is not easy to find so I wanted to share what I've learned about when to sell your company stock.


If you have debt, sell baby sell. Earlier in my career I primarily used any stock I had to do two things, pay off debt and to build an emergency fund. The general conservative financial wisdom would seem to agree that this makes the most sense not just for stock but any sort of windfall or extra income.

Assuming you have no debt and a solid 3-6 month expenses in an emergency fund. Here are some other ways you should think about your stock ranked in order of most conservative to risky.

Sell everything as soon as you can and diversify. Even with no debt, there is solid data to back this one up, check out this article from Wealthfront. Another article walking through why this could be a good idea.

Make a plan and put it on autopilot. This takes the emotion out of when and how to sell. Emotion seems to be the biggest enemy to wise stock selling decisions. There are so many variations, but the key is to decide in advance how much stock you want to sell in what time period. For example you can have a plan to say that 4 years from now I want to have left 25% of a specific stock grant, so you would schedule regular amount of shares to sell each month to sell 75% of your shares. You could also say you'll sell everything over 12 months. The possibilities are endless, but should be influenced by your networth, what your financial needs are in the near and long terms as well as your risk tolerance.

You don't get rich by diversifying. I had a mentor and someone I really respect tell me this. I think I would modify it a little to say "you don't get REALLY rich by diversifying". Think about the employees who followed all the previous advice at Apple, Google, Facebook and all the other stock super stars. They got rich, but not nearly as rich as the would have had they held on for a long time. Most companies are not going to be in that category...but some will be. General conventional financial wisdom suggests you should almost never have more than 10-15% of your network tied up in your company stock. Personally, I think the key is being able to be realistic about the risk and comfortable with it. Can you take on that much risk? Are you more worried about winning big or losing big? Do you have enough money outside of the stock position to do what you want to do for the next 5-7 years? Any big purchases you need to make in the near future? How are you tracking for retirement, kids college savings etc?  If you are in a solid position to have a concentrated position in your company stock and want that to be a high risk/high reward part of your portfolio, then that makes sense.

As I've been talking to experts on this topic and reading up on my own, I keep coming back to one important thing to consider. No matter what you decide to do you need to make a thorough enough and smart decision that no matter what happens with the stock price you can look back and maybe not be happy with the outcome, but be happy with your decision.

In my opinion, what it takes to get to that place is to have a solid plan, get good advice, be realistic about your risk level and have a solid financial foundational.