If you don't have any other streams of income, you might want to think about ways you could get $1k/mo flowing into your bank account to keep you afloat while you flesh this out. $1500 isn't a lot of money, but perhaps that constraint will just make you more creative.

As for the validation that you're seeking, I've seen people do much crazier things that have turned out well. Which is all to say that, yes, the idea is crazy -- maybe even just crazy enough to work if you are committed to it. It sounds like the downside risk to you is pretty minimal, so why not?

To get you started, here's your first tip from an entrepreneur: don't be too attached to the outcome you have planned now. Just like in a startup, once you start on your adventure, you may find that going in a different direction looks more promising. Take the first step, then go where opportunity leads you.

The point of doing it on such a small budget (besides being how much I have) would be to force me into making it up on the fly. The project is deliberately structured to be somewhat open-ended.

So long as you have someone to stay with and feed you to recuperate after its all over, you should go for it. The only thing that should stop you is knowing that you would actually be living on the street when its over and have little way of picking yourself back up.

Set up a website to chronicle your journey posting photos, interviews (even summaries), etc. and put a donate button on it. I wwould donate once I see you're doing it and committed.

Or if you want to try and get the money ahead of time: http://www.kickstarter.com/

+1 on kickstarter - and if you're in NY, I'll give you my couch, the idea is very compelling and if you're passionate about it, you can make it happen.

Worst case, you lose the $1500 and end up looking for a job. Not so bad, is it?

i agree, there are a lot of people out there who have money and are willing to "invest"/donate in people with passion. create a blog, show your passiong and SHARE your passion and you will find a way to earn money.

Yeah, you're a little crazy, but there's no better time than now to do crazy things. It won't get easier, cheaper, less stressful, as you get older. I think you're underestimating the expense of some aspects of this...but if you plan extremely well and live extremely cheap, you can probably live a couple months on the road for $1500.

You should start blogging about your plans (your route, what you're taking with you, who you want to talk to, etc.) immediately...it won't bring in any revenue, but it will (hopefully) get you in touch with enough people willing to help along the way. Video might also be helpful. Once you're actually setting out, you might be able to get enough traffic to bring in some cash. The blogging process is also good for other things...it makes you a better writer, and if you get some traffic it might catch the attention of a publisher or magazine editor.

Also, you can crash at my place when you get to Silicon Valley, if you like.

I'll donate a six-pack to that endeavor, as long as I get to join in drinking it. :)

You can either do it, or always wish you did. Your choice.

I think there's a corollary to this - if it turns out you don't always wish you did, it probably wasn't that great. The question then becomes, how certain are you this is something you will always regret having not done?

The problem is you do not know if its something you regret until you have the regret. From my experience, the more regrets you accumulate, the more you learn to not have them and enjoy the process of life.

He doesn't have to "regret" having not done it, just "wish" he had done it for it to torment him forever.

I don't mean regret having "not" done it. I'm talking about regrets from doing things and "failing" or fear of that happening.

there's a simple experiment for this- just put off doing it for some length of time and measure your regret at intervals. After waiting long enough that you're pretty sure you'll regret it forever, you can do it.

This is one of the best quotes I've read on HN. Very true!

I have also seen much crazier things. A friend of mine from college who is a stand up comedian, decided to hitchhike his way from NYC to LA to "find Tom" of MySpace. He filmed his entire journey and shared it on the web. Additionally, he also crashed with all his MySpace friends the whole way so his cost is practically 0 (besides the bus tickets).

It's definitely doable on an even smaller budget :) Good luck and let me know when you arrive at the valley!

you left us hanging: did he actually find & meet Tom?

You sound like you have nothing holding you down and a great trip ahead of you. Once the job and bills start rolling in it becomes more difficult to break away and do it. Not impossible, just more difficult.

Just do it! I'd recommend doing the west coast bit if you leaning that way.

My way would be Chicago -> Seattle -> San Fran.If time and money and/or your desire permit then swing down the south for Austin -> New Orleans -> NY -> Boston.

How able/averse are you to living with or taking money from your parents while you do this?

I think it's a great idea, but there's no way you've got enough money to do this and take it to the point where it's publishable or monetizable. $1500 is like one month's rent in SF. While you can stretch that out by couchsurfing or camping, there'll be a lot of other expenses (gas? car breaking down? cell phone bills for all the calls you'll need to setup interviews?) And you'll need a lot of time to condense your interviews into something worth reading, and then more time and money to publish it (even if just online).

Again, I think it's a great idea, and it could work well if your parents don't mind you bumming around the house while you collect your notes and make it into a book or blog series or whatever. But if you don't have their support, it may be better to spend a year or so working and save up $10-20k first.

My mom would bankroll my phone bill and probably some other things. She also has her own business, so I could work for her while I compiled my work.

thats what I assumed...you got momma to back you up, she's not gonna let her child starve ;). go for it!!

Sorry to rain on your parade but perhaps you should think about getting a job first. Your savings are not much and if that is all you have in the whole world you can easily get in trouble (imagine, for example a car crash in the middle of nowhere).

And even if everything goes smoothly you can find yourself at the end of your adventure with no money at all. Of course you can set up a donations site but you never know how much donations you will get.

A good way to hang out with entrepenurs without risking your neck would be to get a job with a start-up or a small company. Or you can start a consulting biz that helps small companies (such as website creation, fixing setting up computers, etc.)

It sounds like his mom is willing to back him up if he goes broke. If that's the case, I don't see any reason not to do it.

If you make it to Austin, you can probably sleep on my air mattress and I might be able to introduce you to a couple of people.

You're totally nuts. And can crash at my place for a day if you end up in the silicon valley as well.

agreed. you're welcome to crash at our pad in Boston as well.

ditto Manhattan, if you don't mind getting woken up at 7am by a 2-year-old. PS: as someone below says, ditch the car!

Do it, because you'll not get time to do five years from now, and you might even meet someone who'll want you for a job. Just don't expect to necessarily return from it.

~Matt (met my wife while travelling and ended up in the USA)

How about reaching out to Mixergy and see if he needs any help?

I'm happy to help. I like this idea a lot.

He can make some guest post in Mixergy :D, it will add some value to mixergy and definitely promote his blog/site/project/ebook/<whatever he is thinking here>. Of course Andrew that will choose if it's possible or not, but Andrew rulez and everybody knows that ;)

You the man Andrew!

uh oh - Mixergy's giving me a 500 error...

I know it's driving me nuts. Sorry.

you're not crazy, this would make for a good read. it's like founders at work, but improvised and down in the trenches.

we have a tent you can borrow for a few nights if you'd like, won't charge. look up the palo alto hacker house and if interested email me (jared /at graffitigeo /dot com). we have people who have dropped out of school, left jobs, etc. and would probably be open to letting you profile a bit.

If you haven't made money from writing before, don't count on being able to do it this time. Making money at writing is super bonus extra hard.

I think the majority of successful people failed many times before (and after). And his earlier freelance writing is different from starting his own project (like being a freelance programmer vs. having your own company). And it really is unimportant whether he succeeds with this project. It will teach him certainly many interesting things that give him more background -- for whatever he will do later.

"Making money at writing is super bonus extra hard."

On the whole, perhaps, but if you have a compelling story that appeals to a specific market, you're way ahead of the game.

It helps if you can write, but people pay for shitty writing if the content is otherwise not readily available.

You've put enough thought into the idea that if you don't do it, you'll be regretting it five years down the road, if not sooner. Plus, you're at the point in your life where you can't screw things up too badly if it doesn't work.

I would, however, see if I could dedicate an intense two months to building up a bit more savings. If you can, move back home for these two months. Get two jobs at Starbucks, don't go out, and take the bus to work. Yeah, those months will suck - but it will make the fun parts last longer.

I'd also +1 the idea about ditching your car - you are in the perfect situation for Greyhound/Amtrak: no money and lots of time. Get yourself a rolling suitcase with a suit container, and life out of that. It will handle your clothes nicely, and you shouldn't need any more gear for this than a point-and-shoot digital camera, a little digital voice recorder, and a netbook. You lose the advantage of having a backup hotel, but you save lots of money, and most places have shitty backpacker hostels you can crash in as a desperate measure.

Do it. Just do it.

Normally I wouldn't advice spending everything to your last penny, but I take it that if you are broke you'll just stay at your parents house?

If I understood correctly, you plan the trip so that 1500$ pays for the trip. So on day 1 after the trip you have 0$? Then what?

That aside it is a good idea, probably you'll be invited to lots of things, get donations, maybe even some chances to work.

"So on day 1 after the trip you have 0$?"

And a really good story.

You might be a little crazy. Why don't you put the money in the bank for now and find some entrepreneurs to talk to in Chicago instead of chasing all over the place? You have 37signals in Chicago and Adrian Holovaty of Django/Everyblock and that's just off the top of my head. If you want to go on the road that could be fun as well but just saying.

Exactly! There are probably hundreds of interesting people where you live you could talk to and you wouldn't have to spend so much money on the trip. You really should just try the whole interview thing at least once or twice before you head off.

I don't expect any upvotes on this comment, but if you're in the Annapolis, MD area, I've got a guest room (or couch if you really want) that you're welcome to.

Do it. You just graduated college. This will be an educational breather, and, it could end up influencing your future career. It's going to be tight on $1.5k, but where there is a will, there is a way :)

I'd suggest going about the travel differently. Using a car to get from point A to point B is insanely expensive compared to other methods. Greyhound goes practically everywhere (just not on a convenient schedule/time frame for most people). Also, starting off in Chicago, you've got a fairly major Amtrak hub nearby where you can reach nearly any point in the U.S. by train for a reasonable cost as well.

I would set aside enough money to take Greyhound back to wherever you plan to call home afterwards (from the furthest point away, so you cannot get stranded), then plan out cost to ride Greyhound from place to place. This should give you cheaper day to day costs, but puts you at the mercy of where you're going.

This is where the blog/donate will help out. Put at least a week's notice of what date you plan on being in which city, look for folks to interview and a spot to crash. Ideally you'll be able to "tail" someone for a day or two to really see how their business goes while you're interviewing them. This also would provide for a very interesting read (a day in the life of a entrepreneurs, and not just 1 famous guy, even just in the trenches never heard of them before entrepreneurs). And along the way, share what you've learned with readers and subsequent interviewees.

I agree that a car is expensive, but it doubles it's value by offering me a place to sleep if I can't find one by other means and serving as a big suitcase, allowing me to keep clothes straight and my equipment at the ready.

You need to be able to convince your interviewees to participate. What's in it for them? See http://scobleizer.com/ for someone else who has solved that problem.

One problem is timing. It's not sufficient to turn the interviews into enough money, you have to make that happen at the right time.

I think that your budget is a bit low, but that doesn't mean that this will be more doable later or that it's not doable now.

Yeah, this is the thing that's really bugging me. I don't want to bank on people just inherently wanting to share their story and calling in favors. I've got a couple weeks before I can realistically set out, and that will probably be haunting my thoughts the whole time.

Hopefully, I could offer enough exposure to present an incentive, but this only really works for the less established.

then focus on the less established. there are plenty of really interesting businesses in the 'exchange goods and/or services for money' category that have zero chance (and sometimes less interest) of getting venture capital.

Even those that get seed capital are usually interested in talking with interesting people... and if you do this right you will end up with a lot of contacts, and thus be a very valuable person, even without publicity. There is a lot of value to be had in saying "oh, I talked to this other guy last week who was doing something that would complement your product or service."

Second the "focus on the less established".

I suspect that you'll get better stories from folks who didn't get VC funding. Lots of writers try to get stories from people who are likely to become famous or already are, but the others are likely to have better stories.

Also, many people want their story told, not for biz reasons, but because the think that their life has something useful to show other people.

The guy who wrote "The Soul of the New Machine" says that some of the managers said later that having someone around to chronicle the effort improved the experience. He wasn't sure if they were joking when they said that they were going to try to arrange to have a writer around the next time.

In other words, think bard.

Definitely an interesting thought. I do have a few thoughts you may wish to consider: 1. Consider fewer case studies with more depth. 15-20 will involve a lot of contacts, possibly a lot of travel which will eat into the small savings, and limit your depth. On the other focusing on 6-10 but trying to get in some real time with them (several hours each at least) will let you get a lot more depth with less travel.

2. You may wish to carefully define entrepreneur. By itself it means everything from small business owner, franchise owner, founder of a traditional, capital intensive company (like Intel for instance), founders of web/softare startups, and people who make things in their garage to sell. I have not studied it formally, but I suspect this attract very different people. Unless you specifically want to do a longitudinal study to compare between groups, I would pick one. I presume you are talking about web/software founders, but this should be explicit (or explicitly rejected if I am wrong).

3. Remember you can publish this in numerous formats in short succession. There is nothing wrong with starting with a series of blog posts as a near 'stream of consciousness' on the journey, and then follow up with a book that summarizes, refines, and adds more traditional research/statistics to go along with the case studies you generated.

4. Related to 3, don't ignore physical books as a method of publication. While it is starting to change, there is still a strong bias in many circles giving books more respectability than other forms of publications. Also, they are more easily monetized than most other forms.

5. If you come to Las Vegas I know one software founder and one small business (retail) owner personally I can introduce you to.

You are young so it is a good time to make mistakes. Even if it all goes down the pan you should have something interesting to say at your interview when they ask you what you did after graduation.

Just one niggle, serendipity doesn't make house calls so you should not make plans based on it. make things happen. Once you get going however you might be able to give talks about your journey at tech meets, which should bring up more leads.

I think that your case studies would need to be days rather than just an hour, they would also be more valuable that way. Watching what people do will tell you a very different story than asking them what they are doing. Very few people are willing to admit that their success is down to plain luck, they will tell you all about vision and skill and all that other rock star bullshit. Dumb luck plays a bigger part than people are willing to admit and you will only see that if you spend much more time with people otherwise you could end up just acting as unpaid PR for these people.

Also people lie, which is something that is hard to detect in a one hour interview.

You know, with hard work and a bit of luck ('cause we all need some) this could be a lot of fun

I have no idea what you're asking. 1500 dollars isn't much money, so you should probably get a job, at least until you sort out your thoughts.

Do some research on a fellow by the name of Napolean Hill you may find it interesting.

You will not likely have a better opportunity than now to do this. It sounds fun to me and I am an old guy. I keep wondering. Why would you not also earn a little money along the way as needed? Doing whatever.

Heck, tell the entrepreneurs your interviewing your story and ask if you can sleep in their offices for the night. You'll probably get the real story if you spend a few hours with them after hours anyway.

Aye, [do your tour-of-interviews] and you may [go broke]. [Stay home], and you'll [save $20/day] ... at least a while. And [loosing your soul] in your [cubicle], many years from now, would you be willin' to trade ALL the days, from this day to that, for one chance, just one chance, to come back here and [do your tour-of-interviews] and tell [our corporate overlords] that they may take our [souls], but they'll never take... OUR [DREAMS]!

You're only crazy if you don't stop in Boulder!

I'm a big fan of saving before spending. Go find a job and save up $10k or so. Get yourself enough experience to make yourself thoroughly employable. Then quit and go take that trip.

Being in debt sucks, and doing what you propose will put you into debt in about a month. The end result will be several years of working at some crap company trying to pay it off. Get some savings laid in first, get yourself into a position where you're calling the shots, then go for it.

Sure. Why not? Just make sure you have someone that can send you $20 if you run out of food.

Oh, and I'm in San Diego and should have a couch that you can crash on. Email is in the profile.

Yes you're crazy :-) I love it!

If you find entrepreneurs who'll be willing to share details like these: http://particletree.com/features/web-app-autopsy/

...then you hit a goldmine.

So my suggestion is to go and find start-ups that are not yet well known and get no attention from the bloggers, but are willing to share their numbers.

Publish your case stories as freemium PDF's with kickback to the entrepreneurs.

Best of luck!

Not quite the same thing but Sean Aiken did something similar - http://www.oneweekjob.com/

Sounds like fun.

Get a paypal account and put a donate button on your blog as you chronicle this :-) go ahead and do it but keep us posted, you will be fine.

Do it. It's no crazier than this girl who set out to the end of the world back on a tractor collecting dreams of people.

A great interview on NPR at http://www.pri.org/theworld/?q=node/14897

and more information here: http://www.tractortractor.org/english/

you are crazy.

but it sounds like fun. if you make it to silicon valley be sure to check out the hacker dojo in mountain view: http://hackerdojo.pbworks.com/

Do start a website, and make sure you give your sponsors plenty of publicity. But make the project cool.

If I wasn't spending every penny I can on hardware, (or if I wasn't selling out faster than I can get new servers up) I'd buy some advertising. As it is, I'd be happy to give you some hosting, if you don't have any, and if you make it down here I'll buy or make you dinner.

You should pitch it as "I'm doing this really cool thing, and I think you are really interesting and would add something cool to the project" which should be true. Be aware that respondents will be motivated both by being part of something cool, but mostly by the publicity. But then, it's not good publicity unless it's cool, right?

You probably want to setup the website and build some excitement ahead of time.

so go out and make something cool.

As a 30 something man with corporate career, a wife, child, house and mortgage I say do it. Do it now before you have something to lose. Doing something like what you're propose, you may find a life path that you could never of dreamed of. also, check out the life story Napolean Hill. He made a life out of writing about successful people...

Yes you are crazy. And yes, I say do it. It seems the vast majority of the time, that the less crazy an idea is, the less it's worth doing.

Also, I'm an entrepreneur in Ann Arbor, MI, which could be an option for a closer stop if you want to do a trial one close to home first. We have an extra couch you could crash on.

Sounds like you've got interest....

You probably ought to think a little about where you land after this if it doesn't become profitable, or decide that when your bank account drops to something ($200?) it's time to stop. On the other hand, this is the time to do something like this. It'll only be harder later.

Awesome idea. It sounds a lot like the 'Think and Grow Rich', in which the author (can't remember his name),sought to find and write about the common traits among successfule people at the time. Updating the idea for entrepreneurs, particularly for the sw industry, could be an interesting read.

I'd be willing to put you up in LA when I'm down there for school (late September). I can also introduce you to someone in San Francisco who is a UIUC alum and is running a web dev business (I think there's a few other UIUC guys there too working with him). E-mail in my profile.

Please do it. My life situation means I can't do things like this anymore and I regret it big time.

I don't think you are crazy. Wishing you luck with what you want to do. Just make sure you post back your experiences on HN. Also, like someone suggested, blog about it regularly. Will be great to see whats going on with this idea on a daily basis!

I always wanted to do this too. Last summer I traveled to various cities talking to early-stage funds/incubators and their participants and learned a lot. Now I'm working on a similar blogging project. Pinged you!

I don't really know who you are. But you can crash at my place, if you drive by Portland, OR. I would agree with others, set up a website. People will pitch in for your trip, funny how it works.

If you're on your way up to Seattle from SF, I live in Portland and would totally let you sleep on my futon. I'd even share some beers for a good story or two.

Good luck, and definitely do it.

I don't think you're crazy, it's something uncommon and it'll be a great experience no matter what happens.

If you are happy about your idea, do it without a doubt.

do it! hit me up when you are in sf - 650 283 6558 / mingyeow@gmail (mrtweet.com/discoverio)

(as long as you do not mind my creaking roof - ear plugs provided!)

You're welcome to hit my couch (just outside of Boston) and I"m happy to regale you with stories from our companies first almost-two years.

Damn, I wish I was in the position to think that $1500 was a good chunk of money.

Yes, you're crazy, which is a good thing. Embrace it. Do it while you can.

Sure, go for it. Why not? There's very little risk. $1500 is nothing in the grand scheme of how much money you'll make in your life.

Come to NYC and I'll buy you beers while you interview me about my startup.

Yeah. You can crash in Des Moines if you want (e-mail in profile).

Great f-in idea. Do it.

you can telecommute.

please, do it

You're the right kind of crazy if you ask me. People travel on a much lower budget and I don't mean hobos. Setting up a blog and earning money with it is not a problem. with an original idea like this you get lots of exposure.

Focus on travel products and advertise with affiliate ads. Get publicity by interviewing people the world is or might be interested in.

If you pass through Colorado I can probably introduce you to a couple entrepreneurs: the founders of NetDevil (Jumpgate) and Double Encore, at the very least. I'm also somewhat of an entrepreneur, but just starting out and but a wee little tadpole in comparison to their success.

Where did you go to college?

University of Illinois - Urbana Champaign

My degree is in Political science with concentrations in computer science and economics. I also have about half a degree in physics and a whole lot of coursework (around the reqs for a minor) in math, english, and music.

Just out of curiosity, why such a wide focus? Did you delieberately set out to be "well rounded"?

I personally got a degree in math with a minor in philosophy and a large number of credits in computer science and several very random credits in other fields, but that came about from changing my mind about my major a couple of times.

cool, same here. are you on hndir.com? there is a collection of about 25 or so hackers for uiuc, many of them would be good to check out.

shoot me an email and let us host you for a few nights in palo alto, no costs -- jared /at graffitigeo /dot com

Found a bug in hndir :). It doesn't recognize @uiuc.edu as an illinois address. Not all of us changed, you know!

thumbs up for UIUC. :-)