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So, You Want to Be an Entrepreneur

22 points by prakash 18y ago

swombat 18y ago
All very good points, but I can't help feeling that anyone sensible who uses this list as a guide to whether to start up will never ever start a start-up. It's a scary world out here, and you need a little bit of ignorance (or a lot of arrogance) to get started. I chose the latter option, but not everyone is as arrogant as me ;-)
- tptacek 18y ago
  Which one of the items in this list seem overblown to you? They all seem pretty solid to me. If this list scares you away from entrepreneurship, maybe it's doing you a favor.
  - swombat 18y ago
    They're all real, but it's easy to over-estimate them if you're an intelligent, reasonable, risk-averse individual (like most successful entrepreneurs). Most of those are not "killer" issues, either, like the article presents them. They're just problems you'll encounter and deal with along the way. Being aware of them is worthwhile, but with the caveat that you don't need to resolve all that stuff immediately. I mean, take the last few for example: 9. Are you a self-starter? 8. Do you have a concept you're passionate about? 7. How persuasive and well-spoken are you? 6. What's your track record of executing your ideas? 5. Are you comfortable making decisions on the fly with no playbook? Sure, all those things help with running a business... but do you need to put ticks in all those boxes to start a business? Do you need to be confident in making decisions by the seat of your pants, have a track record of executing ideas, be a persuasive, well-spoken, passionate, self-starter before you even get started? Absolutely not. All that stuff will come with time.
    - tptacek 18y ago
      Ok, but let me be devil's advocate, based on my experience trying to get everyone at my company to be more entrepreneurial: * Some people suck at selling, and freeze up on the phone. They'll put off critical business tasks because they're shy or don't like feeling like whores. And they'll fail because of it. * Some people (cough cough) are great at starting things but have no follow-through ability --- or, in our industry, will tweak and tinker endlessly but never release code. * Lacking an actual playbook for "how to run a company", some people will hew to whatever received wisdom they find, and thus waste weeks getting 110% unit test coverage or waste tens of thousands of dollars hiring a human resources person.
      - swombat 18y ago
        Totally. And those people will fail at their first 1, 2, 3 or more businesses. Perhaps they'll never succeed. But, much like tweaking and tinkering endlessly and never releasing, it's unproductive to worry endlessly and not try. I still suck at making phone calls. I've found a way around that - I have other people with me who can do that better. Ten years ago I had no follow-through. It took me a while, but I learned to overcome that. Tweaking and tinkering endlessly was a problem in my first start-up. It cost me a good kick in the face (figuratively) and I learned to release early and often. Those are all likely mistakes, and some of them you can avoid by reading about them but most of them you'll have to face personally before you overcome them. And, who knows, maybe you'll never overcome them! But the worry should never stop you from trying.
davidw 18y ago
"Sort of". I love to build stuff, and want to be independent. Not sure what other options there are, really.
- tptacek 18y ago
  Freelancing.
  - davidw 18y ago
    Long term? Not really... it's treading water. With either a product company, or a stable, steady job, you still make money when you go on vacation. Not so with freelancing. Unless you are doing genuine 'consulting', where you come in, give some advice, and get paid a crapload for it, freelancing doesn't really seem to be a path to anywhere. Generally, you have to be well recognized to get the really plum jobs, though... which is why you don't see many actual 'freelancers' who are older. To tell the truth, one of the things that most inspires me about "the PG story" is that, at least from afar, he doesn't come across as a guy who wants to build and run a company for years, but who is good at building innovative stuff.
    - tptacek 18y ago
      People who are good at freelancing structure their practice so they have plenty of "bench time" built into their rates. The freelancers I've known throughout my career tend to be more carefree than the rank-and-file developers. More importantly, a consulting practice is a much better platform to build a product business on than a full time job. You can carve out plenty of time for your new business (it's just another one of your clients), you can staff up consulting to make time for the product, and if you fail, you don't have to beg for your job back; it's always there.
      - davidw 18y ago
        I do consulting myself, and prefer it to working a 9 to 5, just that I don't see it as a viable long term option.
jaspertheghost 18y ago
Asking whether you'll jump or not, is always the wrong question. If you're asking yourself that question, you're probably not an entrepreneur. Most entrepreneurs that are successful have multiple previous startups and have always made the jump early and frequently (Jobs and Wozniak with their illegal long distance calling hack, Zuckerberg with a collaborative fitering music sharing app in high school, Aaron (Mint.com) with his multiple startups back in college, etc). Doing every progressive experience gets you used to doing another startup and making you comfortable for the jump. Doing a startup isn't like rolling the dice and seeing if you can win the lottery, it's more of a compulsion. There was a blog entry : http://www.avc.com/a_vc/2008/04/ten-questions-a.html http://www.avc.com/a_vc/2008/04/ten-questions-a.html "Is there an ideal age for an entrepreneur? No, although most start at a young age since they don't belong in big companies. But once an entrepreneur always an entrepreneur. We've got one entrepreneur in our portfolio who is approaching 60 and working on his fourth company."
- gruseom 18y ago
  Woz wasn't an entrepreneur in this sense. He was a hacker who lived for computers and planned to work at HP his entire career.
  - jaspertheghost 18y ago
    Sure, but he was always an inveterate tinkerer. Much like the passage described below: http://www.nytimes.com/books/first/b/bennis-genius.html http://www.nytimes.com/books/first/b/bennis-genius.html Many of the people in our Great Groups are tinkerers--the kind of people who, as children, took the family television apart and tried to put it together again. They are people willing to spend thousands of hours finding out how things work, including things that don't yet exist. There's a joke about engineers that captures the spirit of many participants in creative collaborations. An engineer meets a frog who offers the engineer anything he wants if he will kiss the frog. "No," says the engineer. "Come on," says the frog. "Kiss me, and I'll turn into a beautiful woman." "Nah," says the engineer. "I don't have time for a girlfriend ...but a talking frog, that's really neat. " Members of Great Groups don't fear technology, they embrace it. And they all think that creating the future is really neat.

22 points by prakash 18y ago

All very good points, but I can't help feeling that anyone sensible who uses this list as a guide to whether to start up will never ever start a start-up. It's a scary world out here, and you need a little bit of ignorance (or a lot of arrogance) to get started. I chose the latter option, but not everyone is as arrogant as me ;-)

tptacek 18y ago
Which one of the items in this list seem overblown to you? They all seem pretty solid to me. If this list scares you away from entrepreneurship, maybe it's doing you a favor.
- swombat 18y ago
  They're all real, but it's easy to over-estimate them if you're an intelligent, reasonable, risk-averse individual (like most successful entrepreneurs). Most of those are not "killer" issues, either, like the article presents them. They're just problems you'll encounter and deal with along the way. Being aware of them is worthwhile, but with the caveat that you don't need to resolve all that stuff immediately. I mean, take the last few for example: 9. Are you a self-starter? 8. Do you have a concept you're passionate about? 7. How persuasive and well-spoken are you? 6. What's your track record of executing your ideas? 5. Are you comfortable making decisions on the fly with no playbook? Sure, all those things help with running a business... but do you need to put ticks in all those boxes to start a business? Do you need to be confident in making decisions by the seat of your pants, have a track record of executing ideas, be a persuasive, well-spoken, passionate, self-starter before you even get started? Absolutely not. All that stuff will come with time.
  - tptacek 18y ago
    Ok, but let me be devil's advocate, based on my experience trying to get everyone at my company to be more entrepreneurial: * Some people suck at selling, and freeze up on the phone. They'll put off critical business tasks because they're shy or don't like feeling like whores. And they'll fail because of it. * Some people (cough cough) are great at starting things but have no follow-through ability --- or, in our industry, will tweak and tinker endlessly but never release code. * Lacking an actual playbook for "how to run a company", some people will hew to whatever received wisdom they find, and thus waste weeks getting 110% unit test coverage or waste tens of thousands of dollars hiring a human resources person.
    - swombat 18y ago
      Totally. And those people will fail at their first 1, 2, 3 or more businesses. Perhaps they'll never succeed. But, much like tweaking and tinkering endlessly and never releasing, it's unproductive to worry endlessly and not try. I still suck at making phone calls. I've found a way around that - I have other people with me who can do that better. Ten years ago I had no follow-through. It took me a while, but I learned to overcome that. Tweaking and tinkering endlessly was a problem in my first start-up. It cost me a good kick in the face (figuratively) and I learned to release early and often. Those are all likely mistakes, and some of them you can avoid by reading about them but most of them you'll have to face personally before you overcome them. And, who knows, maybe you'll never overcome them! But the worry should never stop you from trying.

davidw 18y ago

"Sort of". I love to build stuff, and want to be independent. Not sure what other options there are, really.

tptacek 18y ago
Freelancing.
- davidw 18y ago
  Long term? Not really... it's treading water. With either a product company, or a stable, steady job, you still make money when you go on vacation. Not so with freelancing. Unless you are doing genuine 'consulting', where you come in, give some advice, and get paid a crapload for it, freelancing doesn't really seem to be a path to anywhere. Generally, you have to be well recognized to get the really plum jobs, though... which is why you don't see many actual 'freelancers' who are older. To tell the truth, one of the things that most inspires me about "the PG story" is that, at least from afar, he doesn't come across as a guy who wants to build and run a company for years, but who is good at building innovative stuff.
  - tptacek 18y ago
    People who are good at freelancing structure their practice so they have plenty of "bench time" built into their rates. The freelancers I've known throughout my career tend to be more carefree than the rank-and-file developers. More importantly, a consulting practice is a much better platform to build a product business on than a full time job. You can carve out plenty of time for your new business (it's just another one of your clients), you can staff up consulting to make time for the product, and if you fail, you don't have to beg for your job back; it's always there.
    - davidw 18y ago
      I do consulting myself, and prefer it to working a 9 to 5, just that I don't see it as a viable long term option.

jaspertheghost 18y ago

Asking whether you'll jump or not, is always the wrong question. If you're asking yourself that question, you're probably not an entrepreneur. Most entrepreneurs that are successful have multiple previous startups and have always made the jump early and frequently (Jobs and Wozniak with their illegal long distance calling hack, Zuckerberg with a collaborative fitering music sharing app in high school, Aaron (Mint.com) with his multiple startups back in college, etc). Doing every progressive experience gets you used to doing another startup and making you comfortable for the jump. Doing a startup isn't like rolling the dice and seeing if you can win the lottery, it's more of a compulsion. There was a blog entry : http://www.avc.com/a_vc/2008/04/ten-questions-a.html http://www.avc.com/a_vc/2008/04/ten-questions-a.html "Is there an ideal age for an entrepreneur? No, although most start at a young age since they don't belong in big companies. But once an entrepreneur always an entrepreneur. We've got one entrepreneur in our portfolio who is approaching 60 and working on his fourth company."

gruseom 18y ago
Woz wasn't an entrepreneur in this sense. He was a hacker who lived for computers and planned to work at HP his entire career.
- jaspertheghost 18y ago
  Sure, but he was always an inveterate tinkerer. Much like the passage described below: http://www.nytimes.com/books/first/b/bennis-genius.html http://www.nytimes.com/books/first/b/bennis-genius.html Many of the people in our Great Groups are tinkerers--the kind of people who, as children, took the family television apart and tried to put it together again. They are people willing to spend thousands of hours finding out how things work, including things that don't yet exist. There's a joke about engineers that captures the spirit of many participants in creative collaborations. An engineer meets a frog who offers the engineer anything he wants if he will kiss the frog. "No," says the engineer. "Come on," says the frog. "Kiss me, and I'll turn into a beautiful woman." "Nah," says the engineer. "I don't have time for a girlfriend ...but a talking frog, that's really neat. " Members of Great Groups don't fear technology, they embrace it. And they all think that creating the future is really neat.