BOOTSTRAPPING $50/month ★ 152 upvotes 2011

Failure: Building a web app that makes $50/month

Retrospective Overview & Key Insights

Distilled analysis of the business dynamics, operational challenges, and strategic takeaways:

Published in 2011, this chronicle by @mootothemax details the mechanics of building a profitable, self-funded business without venture backing. Key verified financial milestone: $50/month.

Core Principles for Independent Builders:
1
Charging customers from day one acts as the ultimate filter for building software that solves genuine, high-urgency problems.
2
Keeping fixed overhead low and leveraging lean infrastructure allows founders to stay alive until market tailwinds kick in.
3
Small, repetitive improvements in customer retention and conversion rates yield massive returns over multi-year horizons.
Community Debate Themes:

The community focused on B2B customer acquisition channels, cold email vs SEO distribution, and balancing full-time employment with side-project development.

Community Discussions & Critical Reviews

High-signal perspectives, counter-arguments, and peer founder insights debated on Hacker News (58 total discussions):

CO @cooperadymas Peer Contributor

Out of curiosity, why did you decide to make it a separate service from TweetingMachine? It seems like a natural extension of it. That being said, since you have both tools, I would consider approaching it in one of two ways.

First: give InboxCleaner away for free and use it to get registered users for TweetingMachine. I imagine if a user signs up and is happy with one tool you provide, they would be more inclined to pay $20/mo for another related tool. This seems like a great opportunity for some A/B testing as well.

Second: add InboxCleaner as a paid add-on for TweetingMachine. Your customers are paying $20/mo for the basic service, so you know they aren't afraid to pull out their wallets. Offer them a monthly inbox cleaning for an extra $1/mo. What's the difference between $20 and $21 when they're already paying you?

Also, your name might be inhibiting some initial click-throughs to your site. When I hear InboxCleaner, I immediately think email. Maybe this is because I'm not a heavy Twitter user, but it's something to think about.

One feature that might up the ante is email reminders to clean their inbox every 6 months or every year. It's something people will do probably rarely, which means they're likely to forget the name of the tool they used to do it or forget to do it altogether. You might offer a friendly reminder to do Spring cleaning on their inbox.

Anyway, I've really enjoyed reading your posts. They're some of the most practical real world case studies I've come across, as opposed to the "I'm making $2000 a week and only working 4 hours" drivel that's out there. Not that I wouldn't like to make $2000 in 4 hours a week.

TE @techscruggs Peer Contributor

As I suggest in the comments: http://tbbuck.com/building-a-50-dollar-a-month-web-app/#comment-475

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Try presenting your users with a paid and viral choice. First oauth them with the promise of the service you are offering. Then present them with the value proposition: "You are about to save X minutes by automatically deleting Y DM's". Then offer them two choices to compensate you for that value: 1) Follow your twitter account & tweet an endorsement (which could be as simple as a variation on the value prop ) or 2) pay you $0.99 for a one time service.

This will allow you to a) measure your funnel, b) advertise without spending any money, c) build an audience, d) use that audience to build a feedback loop and test other ideas, e) make money in a way that seems to align with your users usage habits.

Thoughts?

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What do yall think, could this dog hunt?

KG @kgtm Peer Contributor

First of all, I would like to thank you very much for your posts, they are informative and have great value for emerging entrepreneurs.

Some thoughts I had:

* You are spot on in concluding that this is a tool that would be used a few of times in a year. A lifetime payment is the solution, with an appropriate price bump of course.

* Regarding the users that signed up for free: You should have allowed them to keep using the service for free. They are your implicit marketing team. They got in early, they deserve gratis access for that.

* Regarding the recurring scheme of cancellations: Do contact the users, ask them why they are leaving. This will help you either validate my first thought above, or iterate on the service to become what they expect to get out of it.

VE @vessenes Peer Contributor

My three comments

a) Payment friction is a big problem here; reviewing comments, I love the idea of overcoming that with an app, but there are also other marketplaces like google chrome apps, etc. Nothing to say you can't sell a web app through one of those right now.

b) Don't email survey your customers, call them. Well, in your case, email them and say you're the founder, you want to know what they liked / didn't, and do they have 10 minutes to give you some advice? This will get you far more than automated surveys

c) I'm kind of thinking a nice "Before / After" with someone's actual inbox would be nice, then they could just click to pay once they see how great it will look.

XS @xsive Peer Contributor

I'm unsurprised people are unwilling to pay for this service: InboxCleaner provides very little added value on top of a service which is free.

Further: it's trivial for a competitor to undercut your app with a free alternative. I suggest you give this away for free to (a) build goodwill and (b) attract people to your other products.

Another thought: you mess with your pricing an awful lot. If I was your customer, and recommending your product to my friends, I'd be pretty pissed to find out the price has changed and made me a liar.

HISTORICAL ERA Web 2.0 Genesis (2007–2013)
COMMUNITY SCORE ★ 152 points
TOTAL DISCUSSIONS 58 comments
TOPICS & TECH STACK: