I ran an operation much like #2 when I was in college (1991). Made a shitload of money doing it, had I been able to reach a wider audience it could have made for a nice enterprise.

Not only are certain brands cheaper in other countries, but products/styles within those brands are not always available in the US (double-exclusive).

FWIW, one thing I did different than what you propose was that I had people who went to the country to purchase and bring stuff back. This was more so based on how this operation came into business, than via intelligent design, but it minimized the remote "friend" problem, and with some deal hunting and advance planning, the airfare can be cheap enough.

A former VP at my previous employer quit and started shangby.com, a live shopping platform for pearls, silk and china around shanghai sitting in your living room. I think they failed. But you should check out their live shopping experience, pretty interesting.

To note: branded goods, standard stuff - remote shopping or exchanges would work. Essentially one is safe when you have a fair idea what is going to be in your package. Else it is a strict no for online buying and more for remote buying.

Re: (3):

* There are at least 20 products in the regulatory compliance (GRC) category, and more in the system scanning category.

* What's more, IT security teams resist buying from tiny companies, because they need to integrate their purchases into their processes and need to know that they're going to get long-term support.

* Most GRC products are sold via direct sales teams (pinning their price to over 50k/sale), which makes it hard to compete without a direct salesperson. Security is a category where low price connotes low quality.

* The sales cycle on new security products is very long --- 2-4 months, with high engagement through the process.

I wouldn't do (3) unless I had a really good idea about how to do it in a new way; that idea should be better than "good looking UI", because as soon as customers express a preference for good UI, all your competitors will drop 20k on a designer to get the merit badge.

Agreed re: everything.

I have a fairly good idea of the competitors, as I've used most of them, and my ideas are much better than a good looking UI, and working policies - the fact that the largest security company in the world can't even supply those basic things makes me think the areas a good target.

Understood re: 50K sales, and agreed re: steak and stripper sales guy - I already have a guy in mind. Agreed re: long engagement - as an architect in my day job I'm on the other end of the coin daily.

In the general entrerprise space, I'd basically be a ServiceNow equivalent to Remedy - multipronged attack on an established competitor at 80% of the price.

Tell you what, though. If you want to sell this thing, what I'd do is, develop it and open source it:

* Enterprises will pay money for open source products. In fact, it's easier for them to pay for open source than to deploy it for free.

* IT people will bring open source stuff in house to play with it, which makes them your shadow sales force.

* It's really easy to qualify accounts for sales; just have an inside sales guy call up and ask if they use your OSS project and like it.

A little confused as to why you, as a sole founder with little hope of securing funding, would choose a direct sales product with a 4 month sales cycle. But, best of luck!

I'm not sure why you don't think I could get a sales guy who owns a chunk of the company. Also conservative, non-ad revenue based products have a better chance of getting investment than the latest chance to make revenue from web services via the oversaturated ad sales market.

But thanks!

I wonder if there's a rule-of-thumb formula that can be applied. "Don't attempt a product with an N-month sales cycle unless you have a company of at least N*M employees."

I suspect M is closer to 10 than 0.25.

If you can leverage contacts to shorten the first few sales then a very small team (2-4 people) can endure the true sales cycle until you pick up momentum.

If your contacts own the budget and purchasing, maybe. Otherwise, you're probably deluding yourself to think that personal relationships are going to cut the sales cycle on an enterprise product. The sales cycle on a securty product at a BigCo includes:

* Weeks of presentations and demos (this part you can cut with relationships)

* Weeks of pilot deployment, which in this guy's case will involve coordination between security, architecture, and server IT.

* Weeks of user education and training (something everybody forgets about).

* Weeks of back-and-forth about missing features and requirements.

* Weeks of negotiation for first PO, assuming all the previous stages went well.

* 3-5 months of delay waiting for receivables.

What friendships will do for you in this process is eliminate the hidden "in-between" steps where people get distracted by their real jobs for 1-3 weeks and don't return your phone calls. But most people don't have friends in BigCo's that can simply cut them checks.

Also, when you try to shop this to VC, most of them aren't going to be impressed by the demo and pilot deployments you've secured with your friends.

Most of the entrepreneurs we work with are over 35, and in many cases know and/or have worked with department managers and senior managers who own a budget and can influence purchasing. For the most part they are not selling applications that are mediated directly by IT in the way that a security app would be so some of the friction is taken out of the process. I do agree that for younger entrepreneurs in the security space you are offering a realistic scenario. My comment was more in response to team size vs. sales cycle than the overall thread, I should have been more specific.

As an Aussie I'd love #2.

Not just for the prices, but for all the stuff that we can't buy anywhere here!

How about a service like this: I give you my credit card details and I get a name/address.

So anytime I need to order something online, it goes to: Mr 12345, Your Address here, 90210,

Whenever something for Mr 12345 comes into your warehouse - you slap my address sticker on it, and ship it off to me. (Charging my CC $10 plus postage).

You might have to answer to the custom (trading tariff?) once this business get big. (I'm guessing here.)

Great idea nevertheless.

1.

The cons here are pretty big. Your target customer is somebody who will solve most problems with google and 3 lines of bash/perl/etc scripting. The generic .NET software shop pays for this kind of software - *nix people don't.

I've written a few more paragraphs about this, and subsequently deleted them. It all really boils down to one thing: it's a bad idea. A lot of fun to write, but there's no money to be made.

2.

It's very hard to get any kind of competitive advantage here. If your idea works somebody else will do the same thing and charge less for the service. Also you will spend most of your time managing your (invariably unreliable) overseas contacts, leaving you no time to do anything else. This seems to be the kind of company that is fun in the beginning, and then turns into a nightmarish chore.

3.

I kind of like this idea. You have domain knowledge here, and already a few potential customers (or at least companies that can give you some feedback.) It's a niche, and there's still money to be made. Best idea so far.

I think number two is your best bet but instead of being a sort of shop overseas service, you should make storefronts focused on one of the brands at a time. Try to make your visitors feel like they have just stumbled upon something thats exclusive and secretive and they are sure to tell their friends.

I think you're right about focusing on brands - it makes the benefit quite apparent for potential customers - but I'd like to avoid targeting a brand directly as it invites legal hassles.

Your second suggestion is spot on - I'd pitch it as an ínternational buying service' much like very wealthy people have. You could even tie in beta testing with Éxclusive' invites, etc.

I just had my mother-in-law pick up some Blundstones for me in Melbourne for about 63 USD, whereas if I want to order them in the US they're at least 145 USD. So I vote for #2 as well :)

The second idea is a cutthroat business. The competition will be fierce and they will be as agile as you are. Number 3 sounds reasonable, but have a way of reaching your customer before jumping in.

You absolutely cannot rely on friends. If your business depends on that, forget it.

I ran idea 2 with my in-house shopping expert (gf) & her first reaction was 'This is so old-fashioned, plenty of people are already doing that on bbs/forums'. So people are already doing it, how are you going to make it better? http://www.dolc.de. (in the second-hand forum / Chinese)

What about taxes? Fraud? You'll need a solid reputation system. I like the idea though.

I think there's a difference between a real second-hand item and an item that legally is second hand, but has never been worn.

I like #2, especially given the other testimony by 'brk' about having made money with a small-scale version of the idea.

There are potential problems in tariff/trade laws, consistency of customer experience, and fraud. But solving those problems gives you your defensible advantage.

Beyond your initial friends, you might wind up with an enthusiastic community of 'buyers'/traders who are working more for the fun/access of it than high salaries/commissions.

And the ads write themselves...

"Where did you get that top?"

"A little shop in Milan!"

"When were you in Milan?"

"I wasn't! Let me tell you about my little secret..."

I think number 2, whilst an interesting idea, has a lot of potential pitfalls. I wonder if this could be done in a social network sense where the community contacts the community looking for items, rather than via one centralised source. The two main barriers as I see are trust (once the money has been sent) and the legals of sending goods into other countries (ie import tax). This one would interest me the most. The Linux one could be useful, but I agree that it could be difficult to make money on it. The 3rd one is interesting on the basis that it should provide a much better service than is currently offered but your main barrier is that the larger companies prefer to deal with larger companies. You may look to sell to the likes of Capita as they could re-package what you do and they are already 'in' with these companies.

Are there any other ideas, or have you refined your ideas down to these three?

I'd go with number 2. It's not high-tech as the other ideas, but it's a business with real cashflow, and is supposed to do better during a recession.

#3 seems like the best option. fastest to develop.

#2 - sure, you save money on the products, but you still have to ship them and pay the buyer. and i'm sure there are legal issues. i bought a dell server recently and had to check a box confirming that i would not sell the machine to someone outside the US.

Idea 3 also sounds like the only one to me that may realistically roll in some money. Idea 1 is technically intriguing but more of an OSS side-project. Idea 2 calls for legal hassles, taxes will eat into your profits and especially the "high-profile" brands that sell $10 products for $500 will probably not like you sidestepping their retail chain.

I think that the other big con for idea 3 is that this is very likely to follow an enterprise sales model. Security in general is the kind of thing that is purchased relatively high up in an IT org. Not 100% clear if your idea would be in that basic mold, but if the model is that the tool runs against or sits on all servers, that would almost certainly be the case.

If you are in the "enterprise" space, that means salespeople, RFPs, support, etc and since all that costs money you are much more tied to a traditional vc model. That could be fine depending on what you want, but it feels different from the other ideas in terms of how much progress you can make on your own or with a small team.

You could probably start by doing some consulting, with an agreement in place that you own the tools you create.

I agree with everyone who says you should do the one that interests you most.

I would do the idea that has the shortest time to producing money. I suspect that's number two, the overseas buyer system.

I would avoid the security analysis tool. The customers sound troublesome, and the competition is likely to be on grounds of the niceness of the reports or something rather and technical correctness. The field has a lot of snake oil, and to be competeing against snake oil with a real product is not necessarily a good position.

The performance analysis tools for linux are needed and might make a good product, BUT: don't do this unless you have a paying customer who wants you to write some high-performance code, and you will be abl to use free distribution of the tool to get more jobs like that.

The overseas buyer is the way to go. Try to get something that is mostly self-service, where you allow buyers to meet sellers and they handle most of the stuff between themselves. Since you will have a web site describing lots of desired goods and visitors who are looking for those goods, you might be able to get some income from adwords.

All the potential hassels described by other folks about that idea apply, but none of them have not been solved before by other import/export people. There are also many regional products in the US that might be distributed this way, such as local brands of BBQ sauces, beer (again the possible legal issues), etc. However none of this is things that Ebay, craigslist, and etsy haven't dealt with.

Almost all of the objections to #2 also apply to on-line auctions. EBay is a relevant existence proof.

Which one would you enjoy working on the most?

I'd enjoy all of them in different ways.

1 scratches a personal itch of mine.

2 I enjoy because it involves (traditional) creative industries.

3 I'd enjoy because I know that 'enterprise' software is so bad it's almost fraudulent, specifically in this area, and I'd enjoy eating these guys lunch.

As drawn as I am to #2, I think you just answered your own question. #1 is where the juice is for you. The value will come. Do it.

Idea 4, which is much like Idea 3.

=========================================

Make Open Source viable for the "medical industry." There are numerous problems with deploying an opensource application environment when it is involved in the care process. Lawyers have made this a legal quagmire to validate software installs, but it can be done, just not for small startups.

By validating linux installs on machines via a process you will lower the barrier to entry for using technology in the medical industry and it should help improve care and reduce cost over all.

Medical companies will pay large dollars at first for this service (probably on order with what they pay for other software of its type).

For example, Documenteum installs can run between $5,000,000 and $50,000,000, where IBM content manager is Cheap, it still will cost on average $500k+ and it needs to be installed on windows.

By managing the documentation correctly, one could design and configure a set of 'validated' applications based on opensource technology.

I know there is money in it, and I would have done it by now, except I am not a linux person.

PS. if you do this well, you could probably get some support from change.gov.

Zed Shaw talked a lot about building a ruby based rules engine / document management system here:

http://news.ycombinator.com/item?id=420650

I think you need to do a little bit more research before picking one of the above. Rather than pick one now, it would be better to spend a little bit of time building up some sort of a business plan (not something to show VC's but just for internal clarity).

Of the three, the 3rd option seems to make most sense to me. The things one would look for are: 1. Customer pain point. Of the three, the third is the most clear. For the other two, its not clear as to who the customer is, or even what pain point you are solving. 2. Your capability to compete (niche markets would be better). 1 and 3 seem better than 2 in this regard.. 3. Cash flow/bootstrap options: 2 and 3 seem to be better, although you may end up paying for agents sitting on the bench before business builds up. 1 is the least attractive since its unclear who will pay for this initially. 4. Competition -- 1 has the least, 2 the most. However it might be better to have some competition, since (often) lack of any competition indicates lack of a market.

Just thoughts off the top of my head..

I'd definitely go for #3. It's such a pain and companies will generally pay in a way that users hate paying. I know I get driven nuts!

#1 would be neat, but one problem would be that you'd have to price it cheaper than better hardware. For example, if your product costs $500/year and I can just double my RAM from 1GB to 2GB for $20/mo, well, I'm just going to double the RAM and save $250. Or likewise any other attribute of the system. It just seems like it would be a lot harder to sell this since most people could probably put the money into hardware and get a better result.

#2 seems interesting, but with postage, is it still a good deal? Personally, I don't see anything wrong with parallel importing - in fact, I'd argue it's a good thing since it stops manufacturers from exploiting market segregation. You're talking about doing it on things like clothing which means problems will be lower. Things like autos or electronics often have regulatory issues. If you're going this route, you might want to consult an attorney.

If you're going to do #2, have a look at the references on http://en.wikipedia.org/wiki/Parallel_importation .

A few years ago there was a lot of talk about parallel import on the news here in Sweden, and if memory serves they said that parallel importing into the EU was illegal (but ok within EU). Might have been due to copyright or trademark reasons, so it may not be the actual importing that was the problem. Worth looking into, anyway.

I'm a programmer, so I'll refrain from giving my opinion on idea 2.

Idea 3, however, seems like a good idea to me. I read the other comments, and yes it will be difficult, but i still think its a good idea.

Idea 1 might be a bit difficult to to turn into a business. In fact, it is something I've been thinking about too for a while now. I was thinking along the lines of support contracts to web hosts or similar businesses. If you choose to work on this(as a business or just on the side), I'd love to help(email in profile).

idea 2

This is a Parallel Import idea, a kind of a grey market. These markets already exist in various niches & I suppose have some potential. (1) You can avoid competition from many big fellas - They can often be kept in line by various means. (2) It addresses an inefficiency in the market. (3) The shrinking world is an ongoing condition making this easier & easier for you. a few ideas:

a - I am not sure a 'buying agent' is necessarily the way to go. Seems like a high overhead.

b - Fashion is an area where retail margins are high anyway. Perhaps higher then your P(London) - P(Sydney) - Incentive to buy in this complicated manner. IE, you might make more per item simply buying @ wholesale & selling @ retail.

c - Parallel imports exist because of either price discrepancies or availability issues. The former is the bigger market while the latter might be more lucrative, given the right clients. If you can find enough people that will buy in $1-2K+ lots time (because they want things unavailable locally) you avoid the a & b issues altogether.

d - Maybe you could use the winter/summer discrepancy between England & Australia in conjunction with price discrepancy to create a double advantage. IE buy Aussie swim brands soon @ sale prices & sell in London in a month or two @ pre season prices.

I like Idea 3 in terms of "you can makes money here". Your "con" on it is genuine but if you can make a product that saves time, you can compete.

The first idea seems like a nice project but its risky as to if it will ever pay the bills. It is about time for the linux world to grow into paid software utils. I certainly wouldn't mind paying for such a tool.

The second idea is too large a market to find and educate. Good service though, I'd like to have access to it if you chose this one.

I've done #2 a bit while in Japan, but stopped because I didn't have enough scale. You have to first communicate about what they want, find where it is sold, take a trip there, box it, stand in line in post office, fill customs forms, do bookkeeping, answer to "where's my package omg wtf!?" e-mails and so on. For customers it was sometimes inconvenient because the packages would be stopped by customs in their home countries.

A) Find the one you are most passionate about with a clear value proposition. B) Make sure there is a wave you are riding, i.e. potentially disruptive platform or something that will put the wind at your back as you ride the waves with this business. C) Make sure there is a customer that wants this- their hair is on fire, doesn't matter if you give them a hose or a fire extinguisher. (whatusername is one example).

#4 keep thinking of ideas

I'd love to see #2 as a way to open up more choices, but I can't imagine ever using it. Just the shipping charges alone would keep me away.

#1, aren't there plenty of tools that do this already? Or at least they have been built already using Cacti and Ganglia in concert with other tools (Nagios comes to mind).

#3 Maybe. You can compete with very large companies if you find the right viable niche that they aren't interested in.

#1: Take it and make it applicable to distributed systems/clusters and maybe you have something.

#2: Is this Fashion News? I kid. This might be a fun site to write, so long as you aren't saddled with the inventory.

#3: Consulting around security is a great way to make a buck, but building a security company of size is very difficult. Automated tools are tricky to write due to false positives due to weird user configurations.

Oh, but the worst thing to do is read this comment stream. Just pick one and do it for a while. If it flops, start another :-)

Number 2 is not really a new idea, but if you can make it work and become the default place for overseas shopping it would be a goldmine. I actually already use a service like this for video games (www.play-asia.com) since I live Japan but I want the English versions of games. Anyway, if you go with number 2 and you need a contact in Japan, send an email my way. :)

I like #1.

Making money from that will be tough complex. Thing about how you can turn this into a product big-corp will want to shell out thousands of dollars on. (selling to individual programmers will be tougher since they are used to GNU being free)

Think about who might be interested in bundling your tool with an existing software/monitoring package.

Go for #1.

Re. #2, there seem to be many human cogs that might not give end-users a consistent level of service

Re. #3, the cost of getting you software in these institutions might require a sales force, and that means to you might need to raise some amount of capital

All this said, a question: which one do you find most exciting to work on?

Regarding 3): Selling to enterprises for a startup is a bitch. We recently a closed an order with ask.com for our product and the the second item in the very first slide in their go/no go meeting was 'What if Radaptive goes bankrupt'.

So what do you think? Are they all OK? All terrible? One stand our more than the others? Thanks for any and all feedback.

"I'd be competing with some very large software companies."

I would call that an advantage.

Two words: exit strategy. Go with three; I like number two, but you don't control the user experience there. Do that with the proceeds you get from selling the company you make for idea three.

Agreed! To quote Richard Branson: pick on someone bigger than you.

That's only good advice if you can go directly to the consumer. Not the same when selling to the enterprise.

Once upon a time I founded a banking software company with my mates. To our surprise there were quite a lot of banks that appeared like shops founded by a guy and his mates as well. But still, they looked at us as if we were from a different star suggesting they buy green antennae and stick them to their heads :)

Questions about #3:

Considering all the servers in the world that ought to be audited with software like yours,

1. Who is deemed responsible for security auditing by management.ownership? In-house administrators or outside consultants?

2. What percentage of these servers are owned by little enterprises (who don't feel the need to buy from IBM/CA/etc.) vs. Fortune 1000 companies?

3. Of those servers whose security audits are done by consulting firms, are those firms big or small?

I'm semi-familiar with the bug tracking software space, so I'll use it as a possible parallel. Every IBM-ish tools vendor sells a bug tracking software package. They're always expensive and sometimes suck. They are sold because a salesman visits a large company and convinces them to buy a big, supposedly integrated suite of products.

Yet, FogBugz (FogCreek) and JIRA (Atlassian) seem to be pretty good businesses. My experiences suggest that smaller customers (1) won't pay 10x just because it's from IBM, (2) buy based on perception of quality/value rather than vendor image, and (3) allow their technical staff to influence purchases like security audit software.

So, back to the questions at the beginning of this post...What percentage of the audit-worthy servers are managed by the kind of people who would purchase FogBugz/JIRA? It seems that you could build you brand reputation among these folks with good blog posts, presentations at conferences, and some guest-authored security articles (the Joel model?).

Noting that I know little about security audit software, one downside may be that companies can CYA by saying, "But, we audited with [Insert big company here]'s award winning industry-standard software tool. How can you blame us for getting hacked? Management may be thinking along these lines when choosing to spend $70K on a POS product. However, your customers may be those who actually care if they're hacked or not!

I don't like #2 because I think you could easily be beaten up on margins, and I don't see why you would be better at running this business than other entrepreneurs out there.

#1 is tough because it doesn't get management attention. Management expects to buy security audit software, and risk aversion leads them to want to make a purchase. However, you'd be relying on a bunch of admins to convince management that they need your tool -- they're likely to use "good enough" Open Source alternatives.

WRT #3, You might consider a model where some basic features are free, but customers pay for enterprise-y features along with support. It's a lot easier to get your product in the door if the users can try it out without going through the hassle of convincing management to dole out $5K.

So, those were my somewhat random thoughts. I'm considering an enterprise software start-up (non-competing) that may have similar sales characteristics.

I LOVE idea number 2. For example, River Island is an awesome fashion retailer in the UK (www.riverisland.com). Perfect for "going nightclubbing" kind of apparel. So a "wrapper portal" to these kinds of sites would be great, especially for people who don't know where the "hot stores" are in a given country. I happen to know about River Island, even though I live in Austin, Texas, because I happen to have spent some time in the UK, but for people who have never been to the UK and want the "hot stuff" this portal idea would fill a real need, provided you can keep your over-head low. Can you rely on your close friends to work? Good question. I agree with President Reagan, trust but verify. You might want to retain a good solicitor to help with legal issues too. I agree the competition for Idea 3 is pretty steep, and that being able to monetize Idea 1 is going to be tough. I might get downvoted for saying this, and I don't care, but I agree with SCO CEO Darl McBride that Linux is essentially a pirated copy of UNIX, and therefore you are correct that UNIX folks won't want to buy Linux tools. Just my opinion there, so downvote if you like, but I think I'm in good company, lol. Anyway, Idea 2 I am definitely exited about, and certainly if anyone here is planning to do any clubbing in the UK and needs some "hip" apparel, definitely check out www.riverisland.com. (Of course I speak from the point of view of the LGBT themed clubs, but imagine River Island would have some good stuff for more mainstream clubs too.)