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Nathan Barry’s $5k App Challenge: My Seasoned Bootstrappy Advice (unicornfree.com)
36 points by route3 on Jan 22, 2013 | hide | past | favorite | 31 comments


"I know Hacker News types think that’s a great list of niches, but it’s actually a really terrible one. You can’t sell to ANY of those people."

This piece of the conversation really left me wanting more, especially since I've been using that very same list with no success over the years. What are some good niches? Better yet, what's a heuristic for picking good niches? She seems to suggest we should focus on an audience we already have, as Nathan has with web developers (designers?), or that we could easily build. So I am the local corporate javascript expert: perhaps I could rally that into an audience of javascript developers or maybe even people that really need javascript developers?


"Not only do those audiences not buy things, not only are they scattered and incoherent and unprofessional and in many cases incompetent and/or broke…"

Ok, so to perhaps answer my own question I'm just going to reverse this. A good niche buys things (specifically software if you're selling it). A good niche is well defined, easy to find and filled with competent people with money to spend.

I think it's interesting that we are defining a kind of person, not a job description or industry.


the keywords here are audiences vs niches. See, audences are made of people with worldviews. Niche is.. well, impersonal agregate, an industry - without any beliefs, pains, dreams...


I think it's interesting that we are defining a kind of person, not a job description or industry.

People buy things… job descriptions and industries don't :)


Selling software and data systems to lawyers is actually a huge business, there exist multiple billion dollar businesses selling to lawers ranging from legal reference systems to machine learning discovery tools.


Sure. SOMEBODY is making money off them. Can you, as a solo founder, not a lawyer, though? That's the question.

SOMEBODY will win the lottery. That doesn't actually increase your chances.

Everything I write, all the advice I give, is increasing the chance that the person I'm talking to will experience success. Some people get rich off consumer products. Some people get rich selling sex, or cool, or experiences. Some people do manage to sell into very tough (but lucrative) industries. But those are all a lot harder than taking the easy path of creating tools for people like you, who have problems you can solve, and who pay money.

Me, I don't like risk. I also never tell people that my way is the only way. It's simply the way with the highest likelihood of returns.

EDIT: By the by, I recently sold back my 12% share in a VERY promising, disruptive startup in the legal space… WITH insider knowledge and connections. The major cofounders worked their tails off for years doing everything right and for their troubles? They got almost zero buy-in. Then they clawed back shares for one last do-or-die thrust (which imo is more likely to be die than do). Unlike many people, I'm speaking from experience.


The argument made is that lawyers don't spend money on software, that's hugely different from saying "solo founder without a domain background" can't sell to lawyers.


Here's what I said to Nathan:

"You can’t sell to ANY of those people."

And he can't.

Are you just quibbling for the sake of quibbling?


Fair enough, I assumed by "You" that you were referring to "You" at large rather than Nathan specifically.


Er, you did? The whole post was a log of an actual conversation I had with Nathan, which I made as clear as a person could possibly make it. The headline is "Me & Nathan Talking About His App Experiment."

What really happened here isn't that you misread, but that you didn't read.


"I know Hacker News types think that’s a great list of niches, but it’s actually a really terrible one. You can’t sell to ANY of those people."

Even as a conversation between two people it's ambiguous what the "you" means, in spoken english it would be distinguished by emphasis.

For example "YOU can’t sell to any of those people." would imply the speaker is referring specifically to the addressee, but "You can’t sell to ANY of those people." would imply a generic "you" referring to the general case of being able to sell to those people.


Exciting to my advice is so controversial it gets me downvoted :)


I wrote about niches vs worldviews and even included a free lesson from my class, because it's such an important & under-reported topic:

http://unicornfree.com/2011/niches-are-for-suckers/

When I said Nathan was throwing away every advantage he had, and he ought to go vertical, I meant to go with an audience where you already have experience, pull, connections, insider knowledge. That's what I mean by "vertical."

So yeah, if you're a go-to JavaScript guy, why would you start anywhere else but there? You'd just be pissing away your advantages.


This seems to be a fairly common problem amongst developers and designers.

The first problem is actually shipping something that customers can buy. I'll skip over this because both Nathan and Amy have certainly been able to do that. So the next step, the 'white whale' project is the infamous second project.

The advice out there suggests either:

1) Outsource Development (it certainly helps if you're a developer)

or

2) Learn it the hard way and do everything yourself

Rob Walling has certainly had fantastic success himself - all by outsourcing. In fact, if I remember correctly, Rob struggled to successfully launch countless products before he chose a different route. Rob chose to purchase existing businesses (HitTail, Beach Towels etc.) and then started marketing them . I don't believe he had any success before that.

Amy Hoy has had great success with building everything herself - Freckle being a great example. However, Amy has also failed with Charm: "It ended up with me spending 2 years and $200k on something I had to shut down."

It seems like it's not just as simple as choosing either option 1 or option 2. There are examples and counter-examples to both options.


I'm a big fan of outsourcing development as that was the route I chose to launch my product (http://www.bidsketch.com) in a much shorter time than it took when I was doing everything myself.

I outsourced the early code and design. Quality of both was shaky, but I only had $3,000 to put into it so I wasn't working with much. I later picked up on the last 25% of the development to get into a beta (since my cash ran out), but I was very glad I took this approach.

I've since been able to work with higher quality of developers and designers and improved both areas, but when you have a product that's solving a real problem, customers will be more than happy to pay for that shaky 1st version (as they did with mine).

That said, I have a dev background and learning Rails before outsourcing it was a big help. I know people that don't have a dev background and successfully outsourced dev of their products (I even helped a couple pick their developers), but it's a bit tougher and it helps if you have at least someone with a dev background that can help you pick the right developer.


Ruben, thanks for chiming in with your experience!

You had development experience and could tell what was going on… and Nathan didn't, which is why I was discouraging him from that route.

I personally don't know anyone w/o dev chops who fully outsourced the development of their product, with success.

I'd love to hear about how your friends made it work. Was it with your help?


You know, after I helped them out with picking a developer, they didn't ask for help once development started. I offered to help but they either didn't run into problems or didn't come to me when they did.

These are the ones that were successful at it...many more were not. But I don't know if the ratio is the same for people with/without dev experience (plus sample size is too small).

What I do know is that most:

1. Got help picking a developer initially

2. Had some guidelines on how to work with a developer

3. Had no development experience

4. Had to get learn how to outsource and made some mistakes (but eventually made it work)

Outsourcing is tough at first but it gets easier. Like any skill, you have to get better at it.

In any case, I do think it's a great idea to learn how to program so you're not so helpless if/when problems come up.


Ruben nailed it with this list. In my experience outsourcing is a continuum; it's not a never/always situation. Meaning you can increase your chance of success by having the factors Ruben mentioned above in place. I would also add that these factors make it easier to outsource your app:

1. Having dev skills

2. Building a mobile app or WP plugin (i.e., something simple) vs. a SaaS app (i.e. tons of moving parts and more ongoing maintenance)

3. Experience outsourcing in the past. It is absolutely a learned skill and the more you do it the better you get.

If you have none of the things Ruben and I have listed (so you're not a dev, you're building a SaaS or other complex app, it's your first time outsourcing, etc...) you have a very, very low chance of succeeding. And if you have every single one you're on the opposite end - IMO the swing could literally be from 10% chance to 90% chance of success depending on the factors you have in place.


Rob, rubeng, this is fantastic insight. It sounds like you have to start small to learn the ropes however ambitious you are. i.e. even if you want to build a SaaS app, if you've got no experience, you will likely fail.

So, if you're new to development, it's probably best to build small products (wp plugins, niche sites etc.) to build your portfolio, earn a little cash and more importantly increase your knowledge and experience. Amy, I'm not sure you would agree with this but I'd love to hear your views.

Aside: Rob, you mentioned that outsourcing is a continuum and something that needs to be learned. Is it possible that some people just get lucky with a great outsourced developer? For example, you've said on various podcasts that you're an advocate of VAs but have you had more than 1 or 2? Presumably, as soon as one works, you stick with him/her - perhaps that's luck rather than learning?


>>So, if you're new to development, it's probably best to build small products (wp plugins, niche sites etc.) to build your portfolio, earn a little cash and more importantly increase your knowledge and experience.

Yes, this is the tact I would take. I talked about this exact topic in-depth on a recent episode of Foolish Adventure: http://foolishadventure.com/audio/how-to-market-your-softwar...

Early successes are huge not only for you learning the ropes of outsourcing/marketing and giving yourself a small financial cushion, but also for building your confidence that you can make this happen.

>>Rob, is it possible that some people just get lucky with a great outsourced developer?

Good point. This is definitely possible. In my list of the 3 factors above I should have added a 4th: You find an awesome developer, whether through luck, having a great network, or knowing how to hire.

But it's just another variable that impacts that continuum I mentioned and pushes you more towards that 90% or 10% end.

>>For example, you've said on various podcasts that you're an advocate of VAs but have you had more than 1 or 2? Presumably, as soon as one works, you stick with him/her - perhaps that's luck rather than learning?

My success rate at hiring and managing VAs, developers, designers, writers, etc... is waaay better than it was when I started (at least 2x better, maybe 3x). I attribute this to getting better at both hiring (i.e., choosing the right fit) and managing/delegating (i.e. having more skill with outsourcing).


> * So, if you're new to development, it's probably best to build small products (wp plugins, niche sites etc.) to build your portfolio, earn a little cash and more importantly increase your knowledge and experience. Amy, I'm not sure you would agree with this but I'd love to hear your views.*

Oh, of course I agree. One of the things I harp on over & over is the idea of stacking the bricks:

http://unicornfree.com/2012/9-years-ago-37signals-had-no-pro...

The whole concept says "Don't try to build a SaaS the first time. Build something small. Don't try to build a huge business the first time. Focus on selling SOMETHING." etc. :)


Hmm, thanks!

One more q: Were these single people with limited budgets, or companies?


Not a prob! :) These were single people with a limited budget. I do have a Bidsketch customer that almost falls into this category (and I helped find a dev), but I didn't include him since he runs a small SEO shop where he's used to outsourcing and had tens of thousands to help him fund the development. Dane Maxwell, which Nathan mentions and doesn't have dev experience, also took the outsourcing approach in building his $40k+/month web app. Though he had a few years experience trying to bootstrap other apps before he was successful to that level.


FWIW, I never claimed to build everything myself… and we (my husband & I) made extensive use of freelance developers, support people, etc. Where do you think the $200k on Charm went? Not to my salary :)

Charm would have been an enormous commercial success based on all the indicators, but we belatedly realized that running it would entail a stressful type of business we didn't want. Big fat "Duh" there. I stake full claim of my mistakes and warn others about it.

This may sound like me twisting definitions but I don't think buying-an-existing-product is the same as outsourcing development, even if it is your only product. In the former, you've got something that already exists, that you can look at and try and poke around in; in the latter, you've got some rough designs and the hope that you picked the right freelancer.

I've seen so many people take the latter course - true outsourcing - and flop around til their money was all gone. Despite trying very hard not to be a party to it, so many of my clients were like that. I eventually had to come to the conclusion that I could push them to cut back features and launch, but it wasn't my job to refuse to do what they asked just because it was dumb.

On the other side, if you fully outsource your product, from scratch, what do you do if (as I mention in the transcript) you have a falling out and suddenly there's a major bug? You not only can't fix it yourself, you aren't sure if you know what it is, how to know if the person you hire can fix it, how to know if they've done a good job or not… plus your track record for hiring is already bad. It's a kind of helpless death spiral — tiny cuts leading to arterial spray.

Sidebar: This has made me realize just how little I know about Rob's origin story, so I'm going to have to fix that :) And by "this" I mean "this discussion" and not "arterial spray," ha!


So, are you saying always keep the core development/design internal?

Regarding Charm, it wasn't always clear to me why you shut it down. You mentioned it here: http://news.ycombinator.com/item?id=4814598 which received some positive and negative comments. I'd rather not start that debate again but it would be interesting to hear your thoughts on whether the development of Charm was the issue i.e. internal vs. outsourced.

Rob has recently detailed his story on the excellent (and fairly new) Product People Podcast (from mijustin): http://productpeople.tv/2013/01/16/ep09-rob-walling-part1/


The issues with Charm have absolutely nothing to do with my position on outsourcing. They're two unrelated points that occurred in the same conversation :)

It wasn't the development that was the issue. It was the preview of things to come, running an infrastructure product, and the general inability to hire somebody to just take that over for us entirely. Do not want.

As for "core"… what does "core" mean?

If you are helpless to fix things in your product, even on a stopgap emergency basis, you are going to be in for some miserable times. Unlike writing or design, code is completely impenetrable if you don't know a lot already.


Nathan and Amy: this is awesome. By letting us “listen in” on your dialogue the lessons in here feel genuine. Great work.

To add a little fuel to the fire, I’ll make a few comments:

> Amy: "I’ve never seen anyone do successful presales for a software product, for the record."

I guess it depends on the definition of “successful” – Jason Cohen had 40 pre-sales before he started building WPEngine: http://blog.asmartbear.com/stop-customer-interviews.html

> Amy: "I don’t know ANYONE… ANYONE… who outsourced their product and made a success out of it."

Again, it depends on your definition of “success” but I personally think Rob Walling is pretty successful, and he outsources almost all of his development: http://www.softwarebyrob.com


It depends more on your definition of "know." :)

Serious question: Isn't Rob originally a developer?

We outsource a lot of our development too, but outsourcing part (even if it's a large part) as a developer is very different than outsourcing all of it, or outsourcing the "core competency" of your product/business, or outsourcing all the code from day 1. Which I still find sketchy and predict will land a person in trouble if they are unable to work on their own product, just as I describe in the transcript!

As for Jason, I didn't know that, that's great. He does write that 40 promised, but only "20 actually did before launch." What I meant, in my terse way, was "presales to fund the development," which is what I understood Nathan to mean because of his only-$5k budget. Jason had some proof of concept in 20 people but that probably paid for just about nothing :) Or… he was able to get a significant pre-sale $$$ by reaching larger, institutional clients with his connections and track record! Which isn't something a bootstrapper starting out should count on.

Thanks for clarifying!


In the comments of his post, Jason wrote:

"Customers are bad about figuring out features, but good about explaining their pain or what they'd like solved."

In your chat with Nathan, you said that people are not good at explaining or even noticing their pains. I guess your experience differs from Jason's in that respect. Mine is probably somewhere in the middle :-)

So, if your prospects are not aware of their pain, how do you sell them your solution?

I expect you have to educate them. It's probably unlikely that you just build something, unveil it, and they go "Of course I need this! Why didn't I think of it?! Silly me! Here's my money."

But then how long do you spend on educating them? Is this why you recommend info products? So that you don't waste time educating for free?

Or do you recommend doing landing page tests?

This is turning into an interview, so I'll stop here. I don't expect you to give away all the secrets you teach in your courses, but would appreciate anything you can share. Thanks!


We have to draw a line between "Customers" as in "Customer interviews" as in "People I want to learn about to maybe build something for who MIGHT become actual customers with money later" -- and actual customers, who are already paying you money.

It's easier to get actual information out of actual customers, because they have something concrete to start with (your existing product).

Speculating about potential problems with Customers™ of the first kind doesn't work so well.

I don't think any of my products were products people would have complained about to start with, but once we (yes!) educated them, they were excited.

Part of education means clearly showing the potential customer what pain they're in that they're currently ignoring. Most people block out daily pain & annoyances… even big ones. After all, if they haven't seen hope that it'll get better, why constantly be upset by it? Natural human coping mechanism. I think this is where big wins exist.


I agree with you that that's where the big wins exist. But, there also lies the eternal tarpit of dead products - email software, project management apps, to-do list apps, etc.




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