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Are you in a startup career path or are you one and done? (gabrielweinberg.com)
91 points by adityakothadiya on Nov 2, 2010 | hide | past | web | favorite | 21 comments

Strongly recommend, if you're interested in startups as a career, that you add "taking a job at a startup and working your way up to a key role" to your to-do list. I know a couple people who have tried to make startups their career by serially founding go-nowhere companies; that's the wrong way to do it.

(My rule of thumb, which I've back-rationalized onto my career, is not to start back-to-back companies).

I totally agree. The reason this is so important is it makes it possible for you to see the ways companies fail without bearing the burden yourself. (Because, odds are, the startups you join will fail.)

It also shows you that there is more than one path to success. I've worked for several startups and each one taught me a different way of thinking about what are the important things to focus on, what kind of people to hire, and what problems are worth solving.

Agree with you and the GP. Both well said.

It wasn't until my fourth start-up job that I found one that I loved and stuck with for more than 1.5 years. Luckily, that one worked out and I was rewarded for it. Not as a founder, but as the GP recommended: work at it and find a key role. Work up from there and get your efforts recognized.

You won't make millions this way but you will learn a lot about business--mainly, how to recognize the good and bad things in your environment, and how to navigate those issues. You also don't have to risk your savings or livelihood. Unless you have a clear or novel idea about what you want (which I didn't), it is a great learning environment.

One thing that I have always known is that I'm not a natural business-type person. After having the safety blanket of learning through 6 years of funded start-ups, rather than on my own dime (and thinking I could do it myself "because it's so easy"), it really helped my long-term prospects of running my own business. One day I will but not yet.

I can't' agree with this enough. I got really lucky. I started as an early employee at a startup that had some excellent folks running it. Just the contacts that I made are worth their weight in gold. Better than that, I learned about scaling a company, raising money, and building traction. As a founder those lessons have been unbelievably helpful.

I think this is kind of important for any development role (not just at a startup). It's definitely good/important to be "the guy everyone goes to" in any organization.


Where did you get this idea? You are absolutely not going to harm your career by having a key role at a startup that dies. Dying is what startups do. Most startups are doomed. Moreover, if you're not the founder or CEO of a startup that dies, nobody is going to attribute anything --- success or failure --- to you, unless you actively campaign to make the attribution happen.

This is bad advice. You should stop giving it.

Depends on what you mean by torpedo'ing your career. Yeah, maybe your options are worthless but you will learn a lot about what does and doesn't work in startups. You can use this in any of your future endeavors. Also, the relationships you form and network you create could be invaluable. My dad worked for a startup that failed about 15 years ago and his friends from it still meet every once in awhile to help each other out and network.

Edit: FYI- he had mentioned working for an unsuccessful startup would torpedo your career.

This also has a lot to do with the fact you shouldn't be starting companies if you haven't worked for one before.

The rationale is that if you don't know what the boss looks like to an employee, you won't know what to do as the boss.

I don't know that I'd go that far. It looks like Graham has found plenty of first-time startup workers that have gotten on base.

I'm not sure how I feel about phrase "startup career path" as concept. Not that I disagree with what Gabriel is saying here, but be careful not to box yourself in conceptually.

I definitely consider myself an early-stage startup guy, and I am extremely hesitant to work for a large company, however I've actually only been in a true startup for 3 years out of a 12-year career. Before that I worked for a public University, a new media agency, and a bunch of small freelance gigs. In all of those circumstances I was able to do great work, meet great people, and learn a lot about business (yes even at the U).

Now it's true that nothing matches the ambition or intensity of a true startup, and it's definitely a place I like to be. Conventional wisdom in silicon valley evolves quickly, but it's very inbred, and it tends to create bubbles of competition around sexy concepts, where hundreds or thousands of the very smartest people in the world are working 18 hour days on some specific concept that doesn't even have a market yet (eg. Check-in-base mobile apps). Meanwhile, out in wider industries you find huge markets with huge inefficiencies due; billion dollar markets that are ripe for disruption, with reasonably small barriers to entry for someone with a little inside information.

If you bring your technical and execution skills to one of these markets you have a much greater chance of success, and with an established market you also can be sure there's something really there. Spending a couple years in an established company could be the seed to a brilliant startup. Likewise, working on yet another social widget just for the sake of being in a "startup" could land you with obsolete skills when app-fatigue turns to backlash, and silicon valley moves onto the next hot thing.

Gabriel, I really like your article because all too often to we get short-sighted and get caught in the "get rich quick" mentality. I think it is critical to balance this long term approach with a firm belief that your current project will make it BIG.

Without this belief that what you are working on will be the next sliced bread, it can be easy to get discouraged or, as you mentioned, move on to the next project.

One of the best startup posts I've read yet - big kudos to @yegg, he's the man.

Thinking that you're going to win by just playing one or two hands is dumb. I also don't like the view that entrepreneurs do it because their personality naturally gravitates towards risk, that's just not smart business.

Only way to win is to take advantage of high EV moments in life, but to also maintain a long-term view and mitigate risk along the way so you can keep playing the game for as long as possible - survival goes before anything else.

Max Levchin failed 4x before he hit it with PayPal. No one becomes a great entrepreneur overnight.

Using investment as an analogy, this is like a barbell strategy. Put most of your portfolio into bonds and put 10% into pure speculation like out-of-the money options.

No, it's not. It's more like the Kelly strategy: http://en.wikipedia.org/wiki/Kelly_criterion

Be ready to seize opportune times, but never risk disaster. The world's greatest entrepreneurs and investors didn't get to where they are today with diversification strategies.

They did it by concentrating the bets they made in life.

I think there are lots of ways to go about startups and only some subset qualify as the yegg's "startup career path." Which is to say, there are a fair number of things that are startups and can be done with a couple coders and some ramen over a couple months -- often not evening needing a "marketing" guru -- while there are lots of other problems which require more specialized domain knowledge (either with respect to technology, market, or both).

In this case, what you need to succeed depends largely on having the right set of skills to succeed within your specific domain, assuming you have one. I'm generally of the opinion that there is much lower risk in these areas (assuming you know your market well) since presumably all you have to do is match an existing need with a product, the primary barrier being your competence.

How do you acquire the skills necessary? This too depends on which side of the ball you are on. Larger startups need people in different roles. Rather than getting in on a little startup and being part-time coder, part-time cleaner, part-time ramen cook, get out in the would and be the most excellent in whatever facet you excel in. Heck, you may decide that making the world a better place in whatever capacity you are best at (usually also what you enjoy) you is better than attempting getting superrich and retiring at 30.

In other words, my advice to all "startup" people out there is do what makes you tick, do it as best as you can, and let your startup, if it arises meet a need that you know is real. This may be a problem that people don't realize is a problem (like limited and often unintuitive course management software) or it may be something bigger and better that only a few people will understand (e.g. a cure for Multiple Sclerosis).

Anyways, I've nothing against serial entrepreneurs if that's what makes you tick. More important though is do what you love.

I wrote a blog post about this a few months ago, the cloud or the ladder:


"Cloud" in this context is an opportunity cloud, the sum total of all the positive things that can happen to you at one particular moment. It is what happens when you position yourself to be in a spot where good things happen, not knowing exactly what.

This is a different strategy than the "ladder" strategy which basically is about climbing a corporate career ladder.

When you're in "startup mode" you constantly try to expand your opportunity cloud but you don't always know the direction. It's a completely different way of thinking compared to the ladder.

I joined my first startup 20+ years ago because I liked creating software, being at the researchy end of the product spectrum, the informality and speed of a small company, having a lot of responsibility, and of course, the prospect of a big payout was attractive.

I've been exceptionally lucky in all of these aspects, so I've been doing nothing but startups since then (except when I found myself at a big company post-acquisition).

If you're going into it just to get rich quick, you are definitely doing it wrong. And your motivation is sufficiently off-course to pretty much guarantee that you won't get what you want.

I respectfully disagree. A start-up is hard. If you're doing anything other than putting maximal effort into your current endeavor odds of success go down.

I think you can certainly be successful in that mode. I was--working in almost complete isolation, and afterwards I still wasn't really a part of the startup community (since I didn't really know many people in it).

What I missed though and what I've realized since is that if you actively engage in that community you end up meeting people that end up helping you that you would otherwise never meet because you can't justify meeting them with your head down all the time.

So it ends up being sort of non-intuitive, and hence the post. I think if you do relax that mode a bit your chances actually go up. Of course there needs to be a balance though.

I'm three years into an ambitious and promising startup now, and feel the same way. I gotta get out and get in touch more with the community.

I'm doing my current job for now, but there's plenty of other stuff I could be doing afterwards. I imagine that I'll probably take a break, but sitting at home growing olives and playing tavla isn't something I could do forever.

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