How does “learning” and “more scope” in startups translate to career success?

Thanks so much for sharing your story - it definitely gives a lot more insight on the upsides of joining a startup. I have a few follow-ups:

1. You had a relatively long tenure as a senior SWE at your two startups (almost 8 years, right?). In hindsight, do you feel like you could’ve gone for staff SWE positions at big tech earlier? If so, when would’ve been the earliest for you to go for these positions?
2. Do you feel like you would’ve had the same amount of career progression today if you had stayed at Microsoft or moved to any big tech besides Meta (seems like Meta is more the exception than the rule when it comes to promo speed)? Why or why not?
3. How were your recruitment prospects as you continued to increase scope/demonstrate impact? Do you feel that you were having an easier time getting callbacks your scope increased?
4. What ended up happening to your 80-person startup?

1. I wasn't interested in going back to big tech :). Like I said above, I terminated my loop with Meta even though they were considering me for E6 (or potentially E7 based on my interview performance). I could've shaved off 2-3 years to get to Staff at another mid-level company by leaving the startup or the fintech sooner. But this is how it worked out due to a variety of reasons and I understand and value the contribution of that phase to my career and life.

2. I don't think I can predict my career progression at any other place. AFAIK, none of the folks I started my career with at Microsoft are Staff now. Most of them are still ICs though. Of course, it's possible that they didn't try at all. See more on my take on this below.

3. The only job I ever applied for was the startup! I had been looking for the right opportunity outside Microsoft for a while, so I went through a phase of mass applying and this startup worked out.

   All my other positions were either though campus placements or recruiter DMs on LinkedIn, including my most recent Staff role and all the other offers I had in that round. I wasn't even active on LinkedIn until recently; I'd only filled out my profile to a reasonable degree. Very fortunately, I have had more recruiters reach out than I could entertain for most of my career. Of course, the market is very different right now.

4. The startup went though a series of acquisitions unless the last company that acquired it got the short end of the stick and basically killed the product. But the primary revenue earning product did live to its late teens. Pretty incredible!

My perspective on predicting career progression:

This might be a hot take, but my long experience has showed me that our dynamic work environment makes it so that success in one environment doesn't guarantee success universally.

It's possible to do very well with your skillset in one team (with a specific manager and team mates and culture) and struggle on a different team within the same company! Even a manager change on a team you're successful on can drastically change things.

Added to this is the fact that different companies treat career trajectories different and value progression differently. There are also D&I aspects at play when it comes to who is set up to progress quickly and who isn't.

Does this answer your questions? Anything you'd like to add?

PS: Thank you for your patience in getting this follow-up. :)

I feel like this question falls apart a bit as some of your materialistic rewards feel arbitrary:

• If getting into Big Tech itself is defined as a reward in and of itself, that places the "inverse" in a bad spot.
• Getting a Senior SWE title is interestingly on the other side of the spectrum as it's easier to get that title in a startup as startup titles tend to be inflated. But zooming out, I don't think that's materialistic at all since your level is just a string next to your name at the end of the day.

Regarding the senior/big tech aspect of my materialistic rewards, what I really meant to say was how much better your recruiting prospects will be when you find your next gig. For example, say you led major revenue generating projects for a small startup and you compete with an average FAANG engineer for the same job at the same level. How much more likely are you going to get the callback compared to him? I think the essence I'm trying to get at is when does scope/impact beat prestige when it comes to recruiting and getting callbacks?

It's possible, but Seed's progression is actually far above average. Meta is an interesting case due to up-or-out, but the vast majority of engineers who join Big Tech straight out of school do not get to L5 within 4 years. For example, Amazon engineers often time take 6-10 years to go from junior -> senior, and this is the case for Google as well (Google will be a few years faster, but L3 -> L5 in 4 years is definitely pretty fast).

At Meta, I met another case of someone leveraging startups for larger growth. They started off at Dropbox for 1 year (this was well before IPO) and then went on to create their own startup (getting into YC). After doing the startup for ~3 years, they joined Meta as E6 (Staff). It is quite rare to go from Meta E3 to E6 in 4 years (maybe 10% of people who join Meta straight out of school can do it).

...

But if the startup is good and you are able to handle it, you'll definitely grow much faster than an engineer who started off at FAANG.

I think the confounding variable here is that Seed and the person you mentioned aren't your ordinary FAANG engineers - they're likely superstars even amongst FAANG engineers. I think it might be unfair to compare them to your average FAANG engineer since Seed (or any superstar engineer) could be at the same place as he is today if he'd joined a big tech like Amazon or Google as opposed to Klaviyo. Unless you're saying that if these superstars had joined big tech, they aren't likely to get the scope necessary to get promos quickly?

For example, say you led major revenue generating projects for a small startup and you compete with an average FAANG engineer for the same job at the same level. How much more likely are you going to get the callback compared to him?

So having a Big Tech name on your resume obviously has a ton of weight (more than most companies), and there's extra nuance from how prestigious your smart startup is. But overall, I wouldn't say Big Tech is strictly superior as the top companies will often pattern match:

1. The best startups will favor great experience at prior startups
2. Bigger companies will favor great experience at prior bigger companies

For #1 as an example, I got an interview opportunity to become Clubhouse's 1st Android engineer while Rahul didn't. Clubhouse is dead now, but back in the pandemic, it was easily the #1 hottest startup (raised from the best investors and was valued at $1 billion in Series B).

They reached out to me because I had experience at Course Hero building their Android app from scratch (something you can pretty much only do at a startup) and building ~30 side projects with 5 million+ users combined. Rahul has only ever worked at Big Tech (he has more Big Tech experience than I do), so he didn't get a reachout.

Unless you're saying that if these superstars had joined big tech, they aren't likely to get the scope necessary to get promos quickly?

Yes, talent needs to be cultivated. I've seen a lot of talented engineers end up on the wrong team in Big Tech and get burnt out. Amazon in particular is particularly brutal with the senior promotion, and I doubt Seed and this other engineer are more naturally talented than every Amazon SDE 2 with 5+ YOE that is struggling to break into senior.

OP, I truly understand your thought process/feelings here. Believe me, I've been there. I want to say that don't worry about trying to min/max and over optimize for "career success". There is no formula. There is no secret sauce. There is no one size fits all.

Can you explain what you mean by over optimising for career success? To me, Taro is a platform for optimising career growth, so I feel like we have different ideas of what optimisation is. In fact, the videos are basically formulas for a successful career. But if I’m trying to understand you better - you mean there’s no straight path to career success?  I’d also be interested in hearing your story, but I understand if you’re uncomfortable doing so.

There is SO much randomness in what gets you a call in big tech that trying to find the most optimal strategy is like the above example in black jack. There was an experiment I saw that two recruiters rarely agree on passing/failing a candidates resume. What Alex said is true, big companies favor experience at big companies and likewise for small companies. While it's true, I will add theres just so much variance that's its very much possible to get callbacks at large companies having worked for smaller companies

I agree with you - even this study by interviewing.io suggests https://interviewing.io/blog/are-recruiters-better-than-a-coin-flip-at-judging-resumes that the recruiting process is really noisy. This study https://www.bu.edu/com/files/2018/10/TheLadders-EyeTracking-StudyC2.pdf shows what recruiters focus on. Having read both studies, the main takeaway is that recruiters don’t really care what you do. So if, even with greater scope and a better profile, I still have marginally better prospects than the average Joe for big tech, then why bother working so hard to get more scope? Why not just work the bare minimum to not get pip’d? You’d probably be better off by putting your marbles into shotgunning resumes and networking into progressively better companies until you reach big tech.

Just do great work, build an awesome network, and help others as much as you can and you'll reach your goals. You really cant force your career (you'll burn out if you're trying so hard and not seeing "wins") you just need to go with the flow and you're less likely to burn out that way :)

The thing is I feel like I’ve been doing good work but nothing’s happening. By good work I mean publishing papers to ICML/AAAI workshops and other conferences, turning my side project into a business, trying to get large scope as an intern by building my company’s core services, connecting with school alumni within my area, going to a top school and getting top grades. I’ve had my resume reviewed by 3 independent sources (one of which is Taro and another is an actual recruiter) and all of them gave the go-ahead.  I’ll admit that it’s only good, not great (compared to some of my friends who’ve published multiple papers to top journals, raised millions pre-seed for their startups, FAANG internships), and maybe that’s the reason I’m not getting a call. If so much of the path to getting better opportunities is gated by the recruiter screen, so much of it is determined by random luck, then why bother trying anymore? If working my butt off will yield the same results as doing the minimum required, then why go through all that unnecessary blood, sweat and tears? The better alternative would just be to rely on law of large numbers and job hop to the very top while doing the minimum required for the job.

I think I get the idea on what's happening. I've been there. I've followed guide after guide lesson after lesson on how to "crack into big tech". Just like you I spent years publishing multiple papers (granted not at tier 1 conference which is really impressive btw) I never got any big tech intvs. I wouldn't say I'm at a point where I'm "successful" afterall I have not worked for big tech and I'm still junior. It's incredibly frustrating, I get it. Especially seeing your peers get into big tech when you feel that you were just as talented is painful. All through college I only got 1 interview and 1 intern offer my last year of college compared to 2 intern offers the prior year. I never got any big tech interviews even

The market is absolutely insane right now. The way you should view this is that all these skills compound with every year of experience you have. You're not gonna see any success for a while but after you get out of intern/new grad purgatory your exact same skills people will value lot more.

The reason you're not getting interviews is because new grads are the riskiest hire even if you're talented, you're still risky. Every year of experience this risk factor drops exponentially.

I've got literally 10x more interviews being 1 year out of college (not having worked for faang/big tech going to a no name college) than the total interviews I had all through college. For the first time in my life I got interviews at reputable companies

The reason I say overoptimizing is bad is because if you place being successful with things that are luck based you will burn out because as youre saying you dont see the reward which is extremely frustrating which is demotivating

Think of it this way, if you read 10 self help productivity books and try and follow a bunch of advice its eventually going to not work out because things dont always work as planned. If you overoptimize then you fail to generalize when things eventually dont follow the rulebook

why bother working so hard to get more scope? Why not just work the bare minimum to not get pip’d

Try to shift your mindset to placing success on things you can control. Focus on being better than you were yesterday. Breaking into big tech = patience + skills + luck

It's a combination of all 3, you need skill to capitalize on luck. You can only job hop so far before it stops being helpful.

Yes, I think there's no straight path to success. Taro is a guide to improve your skills at being successful, but if youre dealt a bad hand/bad luck (this market) you cant do anything.

I truly enjoy the work I do so I dont really mind if it takes me years to get there

TL;DR: Survive this market, trust the process, things will work out over time

OP I have been trying to understand your mindset throughout this thread and I think you have been open now when you say: "Why not just work the bare minimum to not get pip’d"

First off, I think you may be underestimating how much work is required to still be the bare minimum to not get pip'd.

Secondly, you talk in this thread about the time it takes to get to X level a Y company, but if you are serious about career progression you absolutely must do far more than the bare minimum.

Given that $ is what you are optimizing for, I wonder if you have thought about the question: "Do I want a more sure shot at being FIRE rich, or do I want a small shot at being super rich." Like do you want a larger chance at 1 million or a lesser chance at 100 million?

For me personally, I have no interest in big tech. I don't think it is an enjoyable environment and I don't think I would be happy there. But a small close exciting rocketship startup that could make me super rich? That's where I want to be.

Disclaimer: I do enjoy gambling. No Limit Texas Hold'em is my favorite hobby. Maybe that's why the risk factor doesn't turn me off as much.

OP I have been trying to understand your mindset throughout this thread and I think you have been open now when you say: "Why not just work the bare minimum to not get pip’d"

I don’t know what you inferred from my responses, and I have a feeling we’re not on the same page, so I’ll share my motivation and my career goals.

My goal by 30 is to hit at least staff SWE at a big tech company. The reason is that only a handful of people can get to staff - much less at big tech at such a rapid pace. I want to be a part of that group to tell myself I’m at that competency level. My goal is to find the fastest way to get to staff.

Tarodactyl has summed up my mindset pretty well, but here’s more explanation.

I’ve already been trying for the past 4-5 years of my life to crack big tech. In college, I was doing side projects, publishing papers, networking, doing everything I can do just to get a callback. Around 80% of my waking hours were dedicated to working and the remaining 20% were dedicated to “fun” stuff and living. I don’t know what “minimum” means to you, but I definitely did more than just taking classes. However, what I’ve done hasn’t paid off.  Summer after summer, I’ve tried breaking into big tech without any luck despite having a growing resume. I only got offers from startups.

I’ll be graduating next year.  With my internship opportunities gone, I can only head to startups to start my career (unless a lucky break happens).  Seeing my classmates go to big tech, I feel so behind compared to my peers and my goal. I initially felt motivated by Seed’s video and I thought “I’ll build these really cool impactful things and recruiters will totally come for me!” Then I see my peers getting into big tech while I don’t. I’ve put so much effort into trying to impress recruiters, and it hasn’t worked. The real kicker is that my friends who are in FAANG wonder why I haven’t gotten in yet. I think to myself “why try anymore? All recruiters see are shiny gems (brand names) and go after those. They don’t care about what you’ve actually done. It’s probably better just to hop to more and more prestigious companies into big tech.” This is why I posted the question in the first place. I had a hard time believing that recruiters cared about what you did. And even if they did, big tech will still down level you.

Tarodactyl, Alex and Shine’s answers have been very helpful and has kept me hopeful. But I’m nervous - I don’t have much time left (I’ll be 23 by the time I graduate), and people are telling me to keep believing in a process that hasn’t worked for me for several years? I want to believe that it’ll work out, but working hard for several years and hoping that big tech will acknowledge your efforts just doesn’t seem likely.

I hope my explanation has given you a better understanding. I really should’ve done this from the start. To answer your questions:

Secondly, you talk in this thread about the time it takes to get to X level a Y company, but if you are serious about career progression you absolutely must do far more than the bare minimum.

I asked about yoe-to-level expectations is because I need to figure out what benchmarks I need to beat in order catch up to my peers and achieve my goal. I need to know if my pace is outperforming the norm. If you can’t tell from my story, I feel like I’ve been serious about my career, and I’ve been doing more than the bare minimum. I sometimes feel bad that I haven’t worked harder.

Given that $ is what you are optimizing for, I wonder if you have thought about the question: "Do I want a more sure shot at being FIRE rich, or do I want a small shot at being super rich." Like do you want a larger chance at 1 million or a lesser chance at 100 million?

$ isn’t the only thing I’m optimising for. My goal is staff swe in big tech, and I’m trying to figure out the fastest way to get there. To answer your question - I’ll take the sure shot at FIRE’ing. Being FIRE by 30 is also another goal I have.

OP, I 100% get what you're going through. I will say you are NOT running out of time. 23 is still incredibly young. I totally get what you're going through. But it's important to realize 30 is just an arbitrary self imposed deadline. I feel like I tried everything to crack into big tech but I never could.

I've learned to let it go and it will come when it comes. From your story it's clear to me you're consistently comparing yourself to your peers. This mindset is incredibly unhealthy because you're comparing things that are inherently based on luck.

To achieve success you need patience. Good things take time and you never know what curve balls you're going to get hit with that your peers didn't.

I've honestly learned to let go trying to speed run my career. It'll happen when it happens. I found myself incredibly frustrated when i was trying to optimize for something I cant control and now I'm just trying to become a better SWE the best I can with what I have. I'll eventually get in and it'll be okay.

I love what I do so I don't have any plans on retiring soon as well. Your career is a marathon and not a sprint. It's also about the journey and not the destination.