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ASK HN: I'm lost -- need direction
40 points by selfemploy on Oct 11, 2009 | hide | past | favorite | 44 comments
Background:- I am a hacker/developer with over 10 years of experience working with cutting-edge software consulting company. Clients list includes fortune 500 companies many of them banks and some product companies. Skill set includes technology and project execution but not marketing and people management.I am married with kids.

Problem:- Always wanted to be an entrepreneur, right from the college days but never got myself to do anything about it. Now it seems time is running out.

Is it too late to get into startup mode?



Save your money, adjust your lifestyle to allow you to live on a lower spending rate. Make sure your wife is supportive of starting something.

Take your time and find at least one partner. If you don't know them well do some smaller projects together first.

Older entrepreneurs bring social capital, commitment, and an ability to focus and persist (See http://www.skmurphy.com/blog/2009/10/02/three-advantages-of-... )


That's great advice, Sean. I'd also add going to local groups like the one you host, Bootstrapper's Breakfasts. I went to one last year when I started a side project with a friend and got a lot of great feedback. Semi-regular meetups are the kind of thing that can help keep up the momentum over the long haul.


You can be a great half(or third) of a startup team, but you would need at least a marketing guy/girl(and possibly a business process/accounting person). Finding one you can work with might be the hardest part.


It's never too late. As most people have pointed out, most entrepreneurs are older than you expect. The kids who build successful businesses at 20 get all the press because they're the exception, not the rule.

There's lots of examples out there: Jay Adelson founded Digg at 34 and Revision3 at 35. William Hanna and Joe Barbera founded Hanna-Barbera Productions when they were both pushing fifty. You're never too old to get going.

I deeply believe this, because I'm in a similar boat (early thirties and married). Speaking from personal experience, your age will be an advantage more than an impediment. Age gives you experience, and hopefully some maturity and perspective as well. Those will serve you well in a new business venture.

Only one caveat - Make sure that your family is supportive. Starting a new business is a roller coaster, and it helps immeasurably to have the emotional backup. If your wife isn't on board with the idea, then take time to win her over before you take the plunge.

Now, go out there and do it! The only thing holding you back at this point is you.


That's really true. The media will always put on the magazine cover the guy how is billionaire in their twenties. Not necessarily because he is a genius (he may be) but because it sells magazines.


To be a first-time founder in your mid to late 30s, even early 40s, is not unusual at all, especially for ultimately successful companies.

E.g., John Warnock and Charles Geschke founded Adobe when they were 41 and 42, respectively.

Ignore the media fawning of young founders; it's only so much noise, and means nothing in the end.


Jay Adelson founded Digg?


Co-founded. My understanding is that Kevin Rose had the idea, and Adelson helped bring it to fruition.


I'm a nurse with over 15 years of Critical Care experience. I Read Hackers and Painters in 2003, and I went back to school part time for Software Engineering. I finished up last spring, and I started working on being a serial bootstrapper. As soon as I can adjust spending, I'll cut down to part time, or jump ship and do startups full time. I'm 36. I'm married no kids.

I have talked long and hard with my wife about this, and I have total buy in from her. That's huge. I wouldn't be able to do this if she wasn't on board.


What a great story :)


Its not too late, you just can't afford to be in Ramen mode unless you save money ahead of time or your wife has enough income to float you on a startup salary.

My advice: get in a startup as early as you can afford to. If that means being employee 10, so be it. You'll still have a good time. If you can afford to be a founder, do it. But with a wife and kids, joining a funded entity is probably more palatable.

As a more mature adult... you're actually really valuable to a startup: you bring wisdom and perspective. And you're still willing, you haven't 'grown out of it.' Use this to your advantage.

I'd suggest this talk from Damien Katz of CouchDB, about taking the leap to work on a project full time, with a wife and kids - http://www.infoq.com/presentations/katz-couchdb-and-me


This advice is similar to what I've done, and it has worked well for me. The experience you get in a small growing company is (to me, anyway) more valuable than what you get at a larger, more established company.

Advice addendum: Be patient. There aren't many organizations that will work well for what you need, small and fresh enough to remain interesting yet stable enough to support a real family. The good news is that you only need one.


Now it seems time is running out.

That stops being true when you stop thinking it.


No it's not, use your age to your advantage. All the kids are focusing on YATA or YAIA(yet another twitter app or yet another iphone app)...use your old age and life experience and develop something for the baby boomers.

I dunno, a site to create bucket lists with reminders emailed every 24 hours, something like that


Have you found a problem/pain point (at your current job perhaps) that you want to solve and turn into a startup? That's the first thing to consider. The two companies I've started began with "we need to solve this problem" and (in one way or another) then evolved into "hey, this could be a business" ... if you just start with "I want to do a startup", I think there's a higher risk of you making something people don't want/need.

That being said, I don't think it's ever too late.

But being married with kids makes the decision a little harder. Doing a startup on the side (i.e. keeping your job for now) means you sacrifice time with your family. Taking the leap and quitting your job (at some point) may mean a lifestyle change for everyone if you're only ramen profitable or living off savings. Those are decisions you need to make with your spouse. There were some months early on I really put some stress on my wife (financially) ... that's not a discussion where you sugar-coat things or pull a "if only 1% ...".

I'm in my mid thirties, married, and have 4 kids (one is already 15!) so I occasionally feel like an "old founder" when I read about the college kids on HN or TechCrunch. But we do real well now. I think its been 8 years since I had a "real job" ... no regrets.


> In fact, twice as many U.S.-born tech entrepreneurs start ventures in their 50s as do those in their early 20s.

- Kaufmann Foundation for Entrepreneurship, http://www.kauffman.org/Details.aspx?id=1784 "New Study Challenges Popular Perception of Founder Makeup of Technology and Engineering Companies"

The idea of college being "the time" to start a startup is the fact that it's lower-risk, because you can always fall back on college. There is no reason that it is the only time to start a startup; on the contrary, any time is the right time.

I know many an entrepreneur who have started businesses who are well into their 40s and married with children. Your experience is valuable; use it!


To everybody quoting the result that most entrepreneurs are in their 40s: that includes entrepreneurs in clean energy, hardware, other kinds of engineering. I'm not sure there's a study out there about just software/web entrepreneurs. Vivek Wadhwa's study (http://www.techcrunch.com/2009/09/07/when-it-comes-to-foundi..., http://news.ycombinator.com/item?id=874340 below) doesn't separate industries out.


How about this - put aside $500 of your salary each month to hiring a coder on rentacoder that develops and idea for you. Take your time about it, but this is risk free and you get to learn for cheap.


Why do you want to an "entrepreneur"? What does that mean to you?

I don't see a passion for any particular project or idea in your question. I would expect that someone that really wanted to be an entrepreneur, right from their college days, would have moved in that direction somehow -- either by saving funds away so they could do it without disrupting their family, or by working on something on the side in their spare time.

Your question sounds more like it's coming from someone that likes the idea of being an entrepreneur, the 1990's version of, "I want to be an inventor too!" Being an entrepreneur means lots of long days; late or sleepless nights; lots of risk as you bank your welfare, and your family's, on the success of your new business. You don't have marketing or management experience, and those are helpful skills for someone trying to start a new small business.

The majority of startups fail, whether they're a local brick-and-mortar store or a webware-2.0 shindig. The odds are stacked against you. So, what will you do if it doesn't work out? What would you do differently to ensure that your outcome is more successful?

What do you dislike about what you're doing now? Is it just not "sexy" enough? Are you bored, or unchallenged? A side project, or a new job in your career, or even working for an established startup, would all be more logical choices than launching your own business.


PASSION ! The number one pre-requisite. Of course, you need to identify a problem/need/want AND work out how to monetize. If you don't have customers you don't have a business.

So instead of wanting to be an entrepreneur, starting being more aware, find a problem that really get's you going, solve it, tell the world about it and charge them when they turn up. Being passionate and making a difference is what's really important, not some label that you stick on yourself to impress people at cocktail parties.


Many people, all more intelligent than I, tried to warn me about the miseries and ills of starting your own business, and they were right in everything they said.

If I could be content with a safe, regular job at a large company, I would do that instead without a moment's hesitation.

Unfortunately, I seem to suffer from some kind of mental illness which makes me cranky anytime I can blame anyone but myself for whatever mess I find myself in.


That's an interesting view. I'm not scared of doing the hardwork no money entrepreneur thing for a while. Can you give me tips on how to go about finding direction?


No, but I can tell you the only thing that works for me: I have to have a problem that I really, really want to solve. It's not necessarily a problem that I have, it could be -- and often is -- a problem that other people have. The more people have it, the more I want to solve it.

If I've got something like that to focus on, then I'm less likely to lose interest halfway into it.


No. I read somewhere, median age of founders are 40. Use your experience to your advantage. Get yourself a great cofounder and start kick some ass.


This is the question I always ask: do you want to be an entrepreneur or do you want to work for yourself?

Being an entrepreneur is about being so passionate about a product or service that you, and only you, can produce that you're willing to move heaven and earth to get it out there. Working for yourself means freeing yourself from the shackles of pointy haired bosses and stupid corporate policies.

Being an entrepreneur means going for the startup (or opening that bakery or what-have-you); working for yourself means setting out a shingle and starting a consulting practice.

If it's a little bit of column A and a little bit of column B, do the consulting practice for a year, then start your product on the side after you've built up a base of clients to support yourself.


It is more of starting a company and doing everything that is needed to make it success. I have few product ideas but I am agile to change in ideas.


I would caution against an over zealous changing of ideas. The reason that a lot of entrepreneurs fail is because they are too agile in changing ideas in search of the perfect one and never follow through with one of the decent ideas. There is not a perfect idea. The path to riches is through hard work and dedication to an idea that you can execute better than most. You do not need to have the best execution or idea to be a successful entrepreneur.

With that said good luck on your journey!


You asked "Is it too late to get into startup mode?", I don't think so. I think that you might want to discuss this with your wife and get her input into this decision too. Marital acrimony along with the stresses of a startup might take its toll on both of these things, and that would be regrettable.

In any case, as far as getting into "startup mode" it might help if you had an offering that you really believed in. Something to wow the world with. An idea for a product or service that is compelling to you and to others (a lot of others). Something your wife would believe in too.


I don't think it's late to do anything. Richard Bransons mom went around the world and learnt to scuba dive at the age of 85. If she can, then so can you (live your dreams that is).

My harder problem is finding out what your direction is. You obviously have a rich experience so far, what is that interests you? And like Hugh Macleod says, don't ditch the day job, start something on the side see how it rolls and then decide what you want to do with it.

The worst thing you can do is become an entrepreneur because everyone around you is becoming one or because you think that's a way to a quick buck.


From my point of view (a dozen or so years of work wearing many hats, no marketing experience):

Look at your commitments towards you employer, formal and informal ones. If your commitments permit: start on side something noncompeting with your employer. If it works, then its the Decision time.

Do not burn bridges.

To gain some marketing experience, I've started side project which consists of almost no coding and all marketing in very competitive niche. I'm learning every day and, as bonus, have possibility that project will work.


Absolutely not - but it'd probably be a good idea to find (hire or partner with) those who are strong where you're weak. Check this out - http://www.scribd.com/doc/17772299/Anatomy-of-an-Entrepreneu... - it gives an outline of what the typical entrepreneur looks like. For starters, a typical entrepreneur isn't just coming out of university (and that includes entrepreneurs of tech startups).


One methodological issue as I reread that paper: "We allowed company executives to tell us if they were a founder. The guidelines we provided for defining a founder was 'an early employee, who typically joined the company in its first year, before the company developed its products and perfected its business model.'"

Companies often give out the co-founder title to early employees, but that's not what we think of when we read that 'most founders are 40' here at HN.


PDF version:

http://www.kauffman.org/uploadedFiles/ResearchAndPolicy/TheS...

And Google cache HTML:

http://74.125.155.132/search?q=cache:FKhjp-qc6sIJ:www.kauffm...

I never thought I'd find myself suggesting a PDF version, but I really do hate iPaper that much. If only Scribd had put all that effort into doing a PDF to HTML converter that doesn't suck...


i dont see it as a too late or not. more about a risk management issue, especially with kids. They cost money and time. Startups require significant time and doesnt provide much money (in early stage).

can you do it on the side of your day job ? can you financially afford not to have a day job ?

About the age thing, a fun way to considere it is not "they are young and im old", but more "they are inexperienced and i am experienced" :)

and another thing, find at least one partner who is business savy. This is a requirement


I think you could benefit greatly from Gary Vaynerchuk's ideas in this keynote: http://www.youtube.com/watch?v=EhqZ0RU95d4&feature=playe...

The general overview of what he says: it's never too late, you don't have to jump neck deep into it at first (i.e.: quit a job and take funding), you need more passion than Gandhi, and just fucking do it.


If you positioned yourself so well in life then accumulate wealth, wait for retirement and do whatever you like then. There is never too late to become entrepreneur. Being successful entrepreneur is about hiring guys smarter then you anyway so age is no barrier in becoming one.


I think it is a matter of financial planning. When you know the cost of doing a startup, you will know whether you want to jump into it.

Just assume things fail and go against you will give you a good bottom line perspective. At least you have enough buffer to expected failures.

All the best to you. Cheers.


You don't always have to be employee 0, there's plenty of room out in startup land for employee 1s, 2s, 3s, etc. Find industry friends to collaborate on new projects with, or simply go looking for brand-new startups to work for.



Not at all! Wisdom (usually) comes with age.

You're also more likely to have a better partnership with someone young. My partner in my current startup is 55, and I'm 19. We get along great.

I'm looking to start a new project. =]


First things first: There are too many checklists out there for telling you what it takes to be an entrepreneur, I am not talking about them. Do you believe beyond criticism, reason and logic that you have what it takes to be an entreprenreneur??

If the answer is yes, read on. Be sure about it or you will regret this.

I think a good idea will be to take it slow. A phased migration over a time period of year+.

phase1: For a few months at the start, maintain a status quo at current job just keep working right, but change your spending, living and saving habits. Meanwhile prepare your family for the change, slowly. You have lived too long under the cozy umbrella of constant and guaranteed paycheck at the end of every month, that has to change over to a not so persistent income and amounting only to live well and keep the kids just happy. Yes, as someone pointed out, convince and take along your spouse through this transition. Encourage her to take up a job if she is not already doing so. Save money.

phase2: Save more money :-) Then move over to part time, at the same organization if they respect your work or some other organization. You can look at freelancing also, but that a different game, you will have to build that image slowly. Consider yourself lucky if you get good gigs at the start, which is not usually the case. Meanwhile, during this 2nd phase transition, start developing a small fun/serious project or for open source in your part time. As Gary[http://www.youtube.com/watch?v=EhqZ0RU95d4] says: work 9-5, come home, spend an hour with the kids and then 7-1 is enough time to do damage. Second pointer will be start attending dev and entrepreneur unconferences[barcamp, headstart, etc], speak up, listen, you might make a few friends there who can appreciate what you know and vice versa. Do small weekend hackathons with them, to know them more. Not all weekends, some, spend the rest with the family. Hopefully one of these friends will be the one you found your first venture with. Zero on some idea that you are passionate about and a partner who shares the passion and vision. Starting out alone is not usually encouraged, but not ruled out. Start developing a proof of concept and talk to people about it and get feedback. Once you are sure that "this is it" and you have saved enough money for you and your family for 1year, or your spouse earnings will help in that.

phase3: Get in ramen mode. """Startup!!"""

Now you are on a complete uncertain rollercoaster. No turning back. Remember this is a result of the "choice" you made not something that was forced on you, so persevere and may the luck with you.

You can shuffle a few things in the phases. :-)

Hope that helps.


Any entrepreneurs interested in co-founders contact me at selfsemploy AT gmail.com.

Location : bangalore



My buddy Francine says: "do eeeet~!"




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