81–90 of 95 posts
Im at a big tech company now. I’ve learned a valuable set of skills in my lengthy tenure, but I think your FOMO is unwarranted. We’re bogged down in tech debt, legacy systems, endless migration projects, and worst of all, management chains on their way out being replaced by people managers. They’re in technical roles, bringing culture from legacy mega corps like IBM, or IT managers from cost center organizations who…
Since I left big corps 20 years ago, I've spent almost all my time in startups. Most failed, but two were successfully, if not terribly profitably, sold. (As CTO or similar for all, I'm happy to say that the failures fell for business or founding team issues, not technical reasons - my teams always delivered the technology/product, often on impossible schedules and budgets!)
Yes, it's true that (unless your startup is wildly successful) you don't learn to scale things as much in a small company, but in reality, scaling is overrated, and many people spend way too much time foolishly trying to optimize for it. What startups DO teach you is to think about building great solutions for the product at hand. The lack of time and resources inherent even in well-funded startups (I've had the fortune to work in one of those) drives more expansive considerations of options and creative approaches, and a focus on the end goal rather than the process. Big companies simply cannot think this way, and I am very fortunate to have had a couple of my own startups under my belt before I was invited to join others. I think that proved that I had not been made utterly useless by my big-corp experience. (I'd also done a lot of R&D work in the big companies, which is as close to startup mentality as they can get.)
I could go on for quite a while, but suffice it to say, you're not really missing much, if anything (except miserable, bigoted big-corp Diversity, Inclusion, and Equity (DIE) training and policies that will never let you speak freely for fear of HR reprisals...) When I am asked to build teams, unless the client is a big-corp culture that only another bi-corp mentality person can survive in, I strongly prefer to draw from people with smaller company experience - they are usually considerably more capable across disciplines, much more creative, and have an MIH (Make It Happen) mentality that you never find in the big corps. In short, having done both, I consider big-corp experience to be more of a detriment (especially true for PhDs IMO), and startup experience to be invaluable for developing real teamwork, creativity, and the ability to make it real!
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> I'll go against the grain and say that working in startups has been hugely overrated. I don't think that's against the grain, and completely agree with the overrated part. The most surefire way for someone to become financially independent is to work in big tech. The money and job security is unmatched. I've seen it said before that entrepreneurs don't start companies because they want to, but because they have to.…
Odd take. I guess if you're shitty at picking startups. I know so many people who have made multiple 7 figures across secondary sales in various Series A-B companies. A VP at a fast growing SaaS company has millions in equity. Their comparable L-8 type position at BigCo won't give nearly the same upside. It's easier to make mid-high six figures at BigCo. It's easier to make a few million at startups. Frankly, the mos…
Yes, it's possible to make millions in startups. Most don't. I've made a bit, and lost a lot. Over the entire span I've done startups, I'd probably have made more money in a solid, boring, big corp job (working for a year or two for near nothing lowers that average quite a bit), but I have no regrets, and I'd choose the startups again in a heartbeat, since they let me love my work in ways a big corp NEVER can. This rubs off on the entire team, which in a well-run startup, has a drive and cohesiveness that is nearly impossible to create in a big corp.
I hope to make big money in a startup (I'm working on another right now that needs a good all-around developer, since I've graduated my previous one to CTO at another company), but money is NOT the reason to do them. They're just way more fun and rewarding in the ways that matter. (Besides, I still own 88% of one dead company, 25% of another, and 40% of a third. Remember, equity is worth NOTHING until you liquidate it.
Money is fun but won't make you happy - I had a Ferrari for 25 years, but I'm quite happy with the much cheaper, but even speedier 15 year-old sports car I drive now, and to be fair, it's more reliable. (And doesn't track me everywhere like new cars do...)
I'll go against the grain and say that working in startups has been hugely overrated. Each time I worked way harder for less money, and dealing directly with the owner/ceo makes everything so much more complicated. At a bigger company, sure it can be a bureaucratic mess - but I have been much personally happier every time. I get more resources, better pay, and much better work/life balance. I didn't realize how unhap…
> I didn't realize how unhappy I was working at startups until I took a corporate job again and my wife made me promise not to do another startup until the kids are grown up. Same... but in our case the kids haven't come yet. I can't believe how difficult some weeks were for me before landing my current corporate job. My wife says that I seem a lot happier.
If my teams have to work their asses off to get a demo or funding milestone done, I always make sure they get more than that back as time off to decompress and spend time with family. I'm also usually very flexible on hours - as long as they get the job done, I'm OK with almost any working hours they want. This is another benefit of startups - they have the flexibility to do things like that that you can't really pull off in a big co.
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There are many sizes of "startups" too – many Series C and above you'll probably never have to interact with the CEO directly, WLB improves too, but with lower equity and upside
My rule of thumb: if it's big enough to have a dedicated HR person, it's not "really" a startup. Or it's not going to feel like one. The best size IMHO is ~100-1000 employees. Big enough that you have resources at your disposal, but small enough that you can just pick up a problem and start working it.
Why don't you just work at one or two big company and get your FOMO out of the way? The worse case is you make more money (hopefully?) and hate it but you never need to look back, while your best case is a much higher ceiling. You're 30 years old, assuming you work for another 30 doing 1-2 years at 1 or 2 big corp isn't much. I mean from my personal experience, it's really the team within the big corp that you work a…
Edit: Primarily the bit about your team / manager, its the bit that will get you through the worst big corp can fling at you, in most cases.
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Odd take. I guess if you're shitty at picking startups. I know so many people who have made multiple 7 figures across secondary sales in various Series A-B companies. A VP at a fast growing SaaS company has millions in equity. Their comparable L-8 type position at BigCo won't give nearly the same upside. It's easier to make mid-high six figures at BigCo. It's easier to make a few million at startups. Frankly, the mos…
I've been in several startups with really good product/market fit, really good teams/people, and good customers that still didn't make it. (Sometimes it has nothing to do with you, but just luck and the external world, e.g. 9/11 and the 2008/2009 crash. Yes, it's possible to make millions in startups. Most don't. I've made a bit, and lost a lot. Over the entire span I've done startups, I'd probably have made more mon…
What Ferrari model if you don’t mind me asking? Why did you let go of it?
Thoughts on Tesla’s instant torque? Would you consider electric for speed in your next sports car when the industry sunsets internal combustion engines?
Larger companies can have better structure and mentoring available. They can also have more resources and work on more impactful problems. Public companies can have more liquid equity if that is part of the compensation.
Smaller companies can often provide opportunities with more customer impact earlier in your career at the cost of drinking from a firehose and with less resources available. Total comp wise, on average, startups will pay less because their equity is often illiquid and ultimately worthless, however the home runs can pay dramatically more than a large public company will.
I self identify as a roboticist and a generalist. Holistic systems thinking can be very valuable to a broad range of businesses in my experience. Keep learning the mental and mathematical models of your field and it is likely to payoff.
Grass is always greener, so there is just a trade-off on both sides in terms of various vectors like money, culture, stakeholders, scope of work etc.
Now what I also always felt that in startups I just didn't learn things that I also needed to, to become a better PM.
For instance, in our $50m ARR company we ran production-driven development, no tests and very autonomous structure until the company hit around 100 employees and started shifting.
In the company that I joined - we have around 1000x microservices and my product touches around 25 squads that I need to get approval before we even ship a single change.
Is it bad? No, its just different. But the only way to know is to try it. I always thought startups are cooler but now I am humbled to admit that I was also missing learnings from BigCo's like management, structure, async writing of documentation etc. and I kind of enjoy it!