Do You Learn More at a Startup?

I’ve had The Debate many times with people at very different stages of their career – whether to go to a startup, or to work at an established company.  One of the classic arguments for the startup is that you learn more than you would inside the belly of the beast at a large company.

Why it’s True

One of the distinctive things about life at a startup is that everything happens at a hyper-accelerated rate.  Which means that for a given amount of time, you will generally experience much more of the lifecycle of a product, a business, and a company.

I experienced this really vividly when I did my second startup, a  I left Microsoft for the opposite coast to co-found the company.  In two years, we grew it from a few people to over 100, built a massively scalable server infrastructure from scratch and shipped it in six months, became the 50th most active site on the Web, went on a road show and took the company public, lived the exhilaration of flying high, got caught up in the crash and watched our stock go into the tank, had it come back to a more reasonable level, and merged the company with another.  Then my previous partner convinced me to come back to Microsoft to do an internal startup .. and I ran into people who were still working on exactly the same product cycle they had been doing when I left (!).  I felt like a traveller who has gone out into the world, had exotic adventures, and feels utterly changed by them, only to come back and encounter the polite incomprehension of the folks who stayed at home muddling along just as usual.

Another thing is that you typically get involved in a much broader range of activity.  At a big company, division of labor exists (must exist!) at an extreme.  There are hundreds of finance people at Microsoft who are extremely expert at what they do, so your involvement in that discipline even at senior levels of business ownership is very limited.  You consume their work, but that’s very, very different from actually doing it.  Similarly for legal, HR, recruiting, sales, lab management, datacenter design, office facilities, networking infrastructure, ad infinitum.

At a startup, there aren’t any specialists in most areas, so you have to jump in and do them yourself.  You get exposed to many aspects of the business that you wouldn’t otherwise know anything about.  If you like a holistic understanding of what’s happening, you love that.  If you want to focus deep in an area, it can drive you nuts.

But .. It’s Not That Simple

That’s the “pro” argument, but there’s another side of the coin that I think is often glossed over by the advocates.

Because things are moving fast and there aren’t a lot of “experts” around, you usually won’t get trained with any kind of deliberation.  Big companies are very uneven about how thoughtfully they develop their people, so it’s by no means assured that you will get a better experience, but hopefully you will.  I think one of the best way to learn, especially early in your career, is to “apprentice” with a more experienced and expert person.  Ideally, they are a great coach who will push you with challenging work, will evaluate it deeply and give detailed feedback, and they will be there to help when (and only when!) appropriate.  I think you are more likely to get that experience at an established company ..  but lousy managers abound everywhere, so you’ll have to be lucky or smart to find a good one.

It’s rare to get the opportunity to learn big and complex things systematically.  There are areas of expertise that are deep, hard, and take time to absorb.  Things like operating system and database kernels, distributed system design, compiler optimization, and machine learning, are systematic bodies of knowledge that call for the accumulation of knowledge and wisdom over many years to become a true expert.  In startups, you are scrambling like hell and need to get something up that works, so it’s hard to create something that is carefully and thoughtfully designed for the long term.  There are wonderful counter-examples of well-architected systems built by startups, and many pieces of crap built by big teams at established companies, so this is not some universal law.  But, in my experience, you are more likely to get a chance to master those kinds of areas at a big company that has the resources to invest in thoughtful architecture and quantities of deeply trained people available to work on it.

Running a business at scale is different than running a small one.  You won’t learn how to operate at scale at most startups.  Managing teams of hundreds of developers, keeping hundreds or thousands of sales people productive, coordinating hundreds of subsidiaries around the world – these are very difficult things to do well, and you won’t learn about them at a small company.

How it Nets Out

So will you learn more at a startup?  It depends on what you want to learn.  If you want to experience the whole business from customer experience to support to revenue, choose a startup every time.  If you want to move fast and see a lot of things quickly, ditto.

But, if you want to go really deep and immerse yourself in something complex, or you want to train yourself in your craft (whatever it is – systems programming, project management, finance), or you want to learn how to operate at high scale, you might find that you will do better at a larger and more established company.

What’s my approach?  Do both.  I have had by far the most fun at the three startups I’ve done, but I’ve learned powerful lessons at large companies that serve me well in everything I take on, with teams large and small.  And if you are at a startup, and it’s successful, then it’s nice to know that you have experience operating at larger scale – you won’t have to learn every lesson on the fly, when it’s life or death for the company that you do it right.


  1. Very well said. I wouldn’t trade either my 2 startup experiences or my bigco experience. They all contributed a part of my professional skillset. And I especially agree with the conclusion – if you want to learn how to run big projects or big teams, you can’t do that at a startup. And if you want to learn how to do a startup, you really can’t learn how to do that at a big company.

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