BOOTSTRAPPING $5K a Month ★ 647 upvotes 2019

How I Built a $5K a Month Side Project

Retrospective Overview & Key Insights

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

Published in 2019, this chronicle by @jaxsonkhan details the mechanics of building a profitable, self-funded business without venture backing. Key verified financial milestone: $5K a 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 (239 total discussions):

TT @ttty2 Peer Contributor

So how did he got customers?

As I mentioned, my first lead/opportunity came from an introduction. That was made possible when I took a couple friends (who are salespeople) out for drinks to tell them what I was working on. Afterwards they both said they would try to think of people to refer me to.
My next two customers came from a less obvious channel. A friend told me about a service called Growth Geeks and suggested I create a profile for my service. I was hesitant at first because it seemed like a distraction, but I signed up nonetheless.

So basically he sent an email to the founder of that website like this https://static1.squarespace.com/static/5706d181b09f95e331b219de/t/5c37799ff950b7bb44f11390/1547139502227/4+hour+post+img+3.png?format=1000w saying that the author (a bit confusing to figure out as both are called Mike/Michael) can grow your sales with no marketing.

Then this happened:

He responded that day and asked if I had time to speak on the phone.
On the call I learned that he had a customer who needed 2,000 leads a month and they needed 2,000 leads a month for themselves. I used the same sales process as my first call and closed two deals in 30 minutes worth $3,000 / mo (25% of the $4,000 in revenue went to Growth Geeks). Suddenly I went from $1,000/mo to $4,000 / mo.

My question is now, how he manages to make 4k leads?!

Later that week I decided it was time to double down on this side project. I spent a couple nights writing email templates and planning outbound email campaigns. By May of 2015 I had sent over 30,000 sales and marketing emails so I knew how to get high response rates (see play #1).

So now he says he sent over 30000 emails (I assume he has a mailing list of 30000 and sent an email, but that doesn't match what he says, he seems to have sent multiple emails). So let's say he has 30000 email list and a click-through rate of 13.3% (which I think is very very high, maximum I got was around 3-4% and was only once) then he would make 4000 leads.

First thing I think is strange, is how he got 30000 emails? That's kind of the most important part of the guide, without this he couldn't make any lead.

Then he says this:

I sent emails to about 500 people over the course of a month which resulted in ~20 free trial sign-ups. Two of those free trials converted within the month and by the end of June, I had $5,000 in booked MRR.

Note that this is another customer acquisition source. So he has an additional 500 emails.

I mean how can a person reproduce this guide without these mailing lists?

So even if he says how he did it, you can't really do the same unless you have:

- Friends that can sign up for your product or refer other people - Big email lists - Create leads from ???

I feel like all these missing points leads directly to his startup https://getsimpledata.com/ - So I guess is more about marketing.

Anyway, I think the post was interesting, but not too much I can do about it because I probably know about:

- Focus on a problem that already exists - Work on your pain point - Outsource to a cheap country - Positioning in the market

Some types for the author: Philipinnes

DE @derekp7 Peer Contributor

If you don't mind me asking, I'd like some help laying out what my next steps should be on one of my side projects. I had an idea for a side project, ran it by a hand full of friends and associates, expecting to have a bunch of holes poked into it (they have done that to me many times in the past). This time they all think I have something.

Problem is I work full time, as a Linux systems engineer (30 years of Unix experience), with a side passion for C programming, web technologies, and have built a hand full of web apps that are getting a lot of use at work (btw I'm not under any contract prohibiting side projects, and have cleared it with my management).

Next problem: The project itself is relatively simple, has client-side pieces that will be open source, and over all I prototyped it in about a weekend's worth of work, but need probably a month or so to get it more polished and robust. The upshot is that it can be easily replicated by anyone in a similar space. There are similar products that try to solve the same problem, but in a rather backwards and less secure method, but I'm really not sure why other vendors haven't thought of this project first.

Third problem: I'm relatively new at modern advanced web apps, so things like taking payments, handling customers, integrating to a customer's on-premise or cloud based authentication (O365, Active Directory, etc) is something I'm not too familiar with (for my projects I just used ldap bind for authentication against a local AD server).

So for my next step, should I put a prototype / demo site online, and let people create demo accounts that last for a couple weeks? Then if there is sufficient interest, set up something like a Stripe account? Start off with local user account authentication, then later on add the ability for customers to set up users authenticating against their own AD domain or O365 account?

Or would I be better off finding a business partner that has been through all this already?

BU @burtonator Peer Contributor

I actually did this too... I create Datastreamer (http://www.datastreamer.io/) which (when I created it) was an RSS syndication platform as a service.

You gave us RSS feeds and then we would index them and send you the output without having to deal with the insanity of RSS feeds.

This was a decade ago though.

I've been running it since and now it's more of a massive search engine of content - nearly a petabyte at this point.

We have an Elasticsearch API which our customers query. We also have a streaming API if you just want to listen to the crawl data directly.

It's been a wild ride but here's my big takeaway - if your company is profitable it actually might be because you're sitting on something MASSIVE and don't realize it.

Datastreamer was the first company in the content indexing space and we were WAY ahead of everyone else.

I was more focused on enjoying life, traveling, backpacking, etc.

In retrospect when you're sitting on a rocket it might make sense to buy more gas and light up that bad boy.

I'm actually in the middle of a (mild) pivot of Datastreamer right now. We think it might have significant value for the coming 'code war' we're in right now with Russia.

With companies continually looking at social media as a way to manipulate democratic societies these governments need tools (and data) to figure out where they're being attacked and how their citizens are being manipulated.

YE @yellowapple Peer Contributor

I witnessed "Play #3" firsthand. The first startup for which I worked (developing a peer-to-peer learning system that paired up students to learn off one another, whether in person or via video chat) had an uphill battle getting customers and investors because we had to convince them that the problem our product solved was actually a problem they had. Our product happened to chiefly operate by integrating with a different one (Khan Academy), so much of our time "in the wild" pitching to potential customers was spent giving KA free advertisement before we could even explain what our product did.

There were multiple other factors behind why we ultimately didn't succeed and ended up all going our separate ways (and I know I wasn't blameless there), but in hindsight I think this was the central factor. We barely had the resources - sapient or monetary - to sell our own product; trying to sell other people's products upon which ours depended was doomed to fail.

I still think we had an excellent and valuable product, and I stand by the code we wrote and the platform we built; we were just too far ahead of our time :) One of these days, when things like Khan Academy are a bit more mainstream in classrooms, I'd love to (with my old boss' permission, of course) try restarting that particular project and giving it another go.

SY @systematical Peer Contributor

The truth is, there is no 5-10 hour work week for 99% of people. Even if you make something like this person did, if you don't continue investing a lot of time into it, eventually competition will break you to pieces. Why? Because your competitor is hungry and working a lot more than 5-10 hours a week.

I know this, because I've built two side income businesses, sat back and collected money only to find competitors had taken me over. They weren't big by any means but the $3,000 a month I made off one and the $1,000 a month off another was quite nice. I could've quit my job and traveled, but instead I paid down my mortgage and banked/invested the rest. This left me with a lot of money (for me). I eventually sold both businesses when I saw the writing on the wall with various competitors and industry changes.

I did end up traveling for a while though. I did that with a remote job. Sure I had to work during the day, but that left plenty of time to explore whatever city I was in at night and do bigger adventures on the weekend.

TLDR; 5-10 hour work week doesn't last.

HISTORICAL ERA Cloud & Mobile Era (2014–2019)
COMMUNITY SCORE ★ 647 points
TOTAL DISCUSSIONS 239 comments
TOPICS & TECH STACK:
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