What advice would you give junior engineers on moving to San Francisco and working at a startup?

My hot take is that moving to San Francisco was one of the best decisions I’ve made in life. The essence of the place is wild, contradictory, optimistic, cynical, and always changing. Nothing about the city wants you to get comfortable for long. Because of that you’ll be challenged every day with new perspectives, opportunities, and change.

But you’re asking about startups not personal growth, right? Without question: this is the place to be for startups! If you wanted to learn from the best painters and could choose any place in history, you’d choose to live in Renaissance era Italy. If you want to learn about the startup world then there is no better place than Silicon Valley to spend a few years. Some advice to help you get started:

1. Tech Skills: Learn Python, JavaScript, and/or React

While every company makes different tech choices, you’ll open more doors by focusing on these languages. Python has certainly become a powerhouse and it is the best place to get started for an engineer interested in back-end development. If your aspirations point more toward front-end development then look at React, which seems to be winning the UI framework wars nowadays. Everyone needs to learn JavaScript as it will probably become the standard for coding everything in the next decade (as a person who started their career with C++/Assembly this a terrifying but, I’ll admit, powerful change).

2. Evaluate startup opportunities the same way a Venture Capital firm would

Once you start exploring jobs in Silicon Valley, you’ll find an unbelievable range of opportunity. The first month of my job search included a food delivery startup, a micro-satellite company, a social network, a platform for drones, and a geospatial analytics firm. I even got pitched on “BitMoji for dogs.”

My suggestion when evaluating all these options is to choose a company where you are passionate about the product, see exciting learning opportunities, and vibe with the culture. Of course, you also need to look at the monetary aspect. Part of your compensation will be in the form of options or RSUs which can turn into real money if the company has a future liquidity event. So how do you know how much this form of compensation is worth?

Isn’t that the million-dollar question? No one can predict the future, but to evaluate startups on the dimension of “likeliness of having a liquidity event” I suggest using the same business metrics a venture capitalist would use. Does the startup have experienced co-founders with previous exits? What’s the annual recurring revenue (ARR) and is there a path to the important $100M threshold? Growth rate? Dollar based net retention (DBNR) that indicates happy customers? Remaining runway?

You might not get answers up front, but you should be wary of any startup that refuses to share an indication of business health at some point during the interview process.

3. Yes, equity DOES matter

During your interview process, you might hear someone (perhaps a mustache-twirling recruiter) say “startup equity is just lotto tickets.” Don’t get lulled into the false sense that you shouldn’t pay attention to equity. Equity can be life changing and is a critical component to consider in your total compensation.

Ok yes — if you join an early stage startup the odds are against you seeing a liquidity event. Even so, you should try to maximize your equity during offer negotiations and take advantage of tax benefits such as the 83(b) election while you have a favorable strike price if you do land the gig. If your company has a liquidity event someday this forward thinking will save you a ton of money. Another thing you’ll want to consider up front is asking for an adjustment to the typical 90-day options expiration period so that you don’t end up with zero equity if you leave the company before a liquidity event. By retaining equity, you can continue to grow wealth even if you are no longer employed with the company.

At later stage startups, understanding how equity maps to total compensation is more straightforward and the likelihood of your “lotto tickets” paying off is increased. Depending on how strong the positive signal is, you may consider some advanced job offer negotiation strategies. I have encountered savvy job-seekers who asked about trading off salary for equity or even asking for the opportunity to buy company equity during the next fundraising round. This may be too much for a first-timer to deal with but keep it in mind for future jobs. Which reminds me…

4. You probably won’t stay long

People flock to New York to be in finance, to LA to become movie stars, and to San Francisco to become startup millionaires. It often feels like everyone you meet is from somewhere else and thinking about moving somewhere else.

Tenures are short. Expect to start another job search after 1.5 years and expect to leave San Francisco within 5 years.

Be careful about staying any longer. Similar to how Gizmo turns into a Gremlin after midnight, if you stay in San Francisco past 5 years you’ll most likely transform into a Venture Capitalist.

5. Managers don’t manage your career

It will be rare to get the same level of career support and guidance at a startup as you might expect from a larger company. About half the startups I consult with haven’t even set up proper job ladders or performance review systems. That doesn’t mean they have bad intentions — it’s more that well-implemented career support systems don’t emerge until the later growth phases of a company.

What this means for you is that you’ll need to take charge of your career by understanding how the company is growing, proactively looking for opportunities within AND outside the company, thoughtfully networking, and holding yourself accountable to good work.

6. San Francisco is amazingly rich and jaw-droppingly poor at the same time

I have only lived in San Francisco for 3 years but in that short time I have seen wild extravagance and extreme poverty side by side in a way that I have not encountered anywhere else in the world. Everyone I know who moves here experiences an adjustment period where they are at first shocked then become numb over time.

I’m not sure I have any real advice on how to deal with that feeling, everyone will process the situation differently. But I would humbly make a suggestion. Always keep in mind that being a part of SF’s tech scene at all puts you in a position of immense privilege and high potential. How we treat others not afforded that same privilege is both a measure of our character and an indicator of whether we are worthy of the rewards that come with success.

I shall now step down from my soapbox on this incredibly complex issue. Good luck.

7. All the cool people live in Oakland

rock on, nick