Should I leave my well-paid FAMG job? Or Join a startup? Here is a framework for your Engg career decisions

Don’t try to be a specialist too early in life. In the early years of career, everything you can know, you must know. Over time, you will naturally develop expertise in some. Anything <5 years is early. Remember, one cannot get a PhD before completing high school

Shreyas Doshi
Over the past 10 years, I’ve had more than 500 chats with talented tech folks about their job change decisions: should I leave my well-paid FAMG job? should I join Stripe, Facebook or Airbnb? how to evaluate this offer? etc A thread with 8 ideas I’ve often shared in these chats:
Note: Each of us has different aspirations, skills & values. No thread can definitively cover everyone’s situation while still offering a new & useful perspective. This stuff likely won’t apply outside tech/startups & won’t apply worldwide. Take what resonates, ignore the rest.
I highly recommend working at a fast-growth company at least once in one’s career. (doing it more than once might not hurt either 🙂 ) I’ve seen that even smart & talented people struggle with how to create their shortlist of fast-growing companies. Here’s what I tell them:
1/ Pay attention to growth rate, market size, customer satisfaction. If a company is growing really fast in a large market & its customers are highly satisfied (or are telling everyone they know about it), it should likely be on your shortlist of companies to consider seriously.
2/ Pay attention to the Founders. A friend recently called for advice on an offer from a 50 person series A startup. He wanted to know if he should ask for 5-10 bps more in equity & $20k more in cash. I asked him if he had talked to the startup’s Founder/CEO yet. He hadn’t.
I told him that his question of whether or not he should accept an early stage startup’s offer at XYZ terms was irrelevant until he had met & evaluated the Founder 0.75% of zero is still zero whereas 0.5% of $20B is a lot Early on, the caliber of Founders is the best predictor.
This resonated with him. He then asked how he should evaluate the Founder.
I gave him this simple heuristic: Ask questions that you genuinely have about the background, mission, customers, business, culture, challenges. Evaluate the Founder’s answers. Then ask yourself “Do I think this person is among the most capable people I have ever met?”
If the answer is No/Maybe, you may still decide to join, but be careful & make sure there are other great redeeming factors not related to the numbers in the offer. If the answer is Yes, by all means get the best offer you can, but don’t sweat over 5 bps of equity here or there.
3/ It always feels too early or too late. When a company is growing very fast, some people choose not to join because of regret that they missed out on previous growth. Other people choose not to join just yet because the explosive growth has created problems that scare them.
People in the first bucket will say: “It’s too late to join. I should’ve joined 2 years ago”. People in the second bucket will say: “It’s too early to join. I will join after they’ve fixed their go-to-market org structure (or whatever)”. They are too smart for their own good.
Instead, think about it this way so you don’t fall prey to the too late/too early error: The best time to join an awesome fast-growing company was as its first employee. The second best time to join that company is now.
4/ Every company has problems. It may not appear that way from the outside, but even the very best companies have major problems. Peek carefully inside an impressive rocketship company that’s a darling of the press and you will still see a plethora of problems. Guaranteed.
Why it is important to internalize this: – Some people are excited about a company, learn more about it in the interview process, and get scared because they didn’t expect to see problems – Some people quit a rocketship too early because they weren’t expecting so many problems
The question you should be asking is whether your goals, principles & values are misaligned with the problems you see. Personal example: I am quite okay with product/process problems & org structure problems. I am not at all okay with a low talent bar & culture problems. YMMV.
5/ People matter more than you think. Something odd happens on your 1st day at a company. Remember that Offer Comparison Spreadsheet you created? It won’t matter at all from this point on. The caliber of your coworkers will dictate your day-to-day fulfillment more than any math
So pick a company with high caliber people & an aligned culture. When times are tough, that’s what’ll help you persist & not quit too early with burnout. And it turns out that people & culture are also a good predictor for your spreadsheet math working out the way you want it to.
6/ Domain matters less than you think. Assuming you have the foundational skills, don’t outright reject an otherwise great company in a different domain just because you’ve never worked in that domain (say b2b vs. consumer). When you work with great people, domain matters less.
7/ Don’t let an ego hit get in the way. I know so many very smart people who have made terrible decisions by rejecting an offer from an amazing company mainly because “scope isn’t large enough”, “would be a step down on title”, “prospective manager is more junior than me”, etc.
I am not saying that you should always ignore scope, title, prospective manager. But I am saying that you should understand that at a fast growing company things will change all the time. Scope will grow, title will come, your manager will change. Temporary ego can be expensive.
8/ Apply where the bar is high. Some people never end up applying to really promising companies that check all their boxes for a dream job. Why? Because they have heard that the company’s hiring bar is high, and deep down, they don’t want to risk getting a rejection.
If this is you, you are not alone. The first and most important step here is going to be to admit the real reason why you are resisting applying to that company. And then find your own way to combat it. No one can solve this problem for you. You will need to solve it yourself.
There’s a lot more to say, but I will stop now after offering one last thought. Notice I didn’t say much about the company’s mission, impact in the role, your ability to learn, solving interesting problems, etc.
Because: – For very talented people, these should be table-stakes, not clinching factors – Too many people say in interviews that impact, mission, and ability to learn are all that matter to them. While that may be a fine interview answer, it is rarely the full, real answer.
With enough repetition, we end up believing these partial answers we tell others. And then we make unrigorous career choices we later regret. Of course the company’s mission *is* important. But that mission by itself isn’t going to pay for your kids’ college or your retirement.
To recap the 8 ideas: Growth rate, market, CSAT Evaluate the founder(s) It always feels too early or too late Every company has problems People matter more than you think Domain matters less than you think Combat temporary ego Apply where the bar is high
And to sum it all up in a few lines: Join a fast-growing company in a large market with high caliber people and a culture that’s aligned with your values. Do that whenever you are ready and the company is too. I wish you all the very best!
If you are hiring at a fast-growing company with high caliber people & culture, go ahead and promote your company & your jobs page by replying to this tweet so great people can find you.
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