BOOTSTRAPPING $50/mo ★ 236 upvotes 2020

I got my first $50/mo customer

Retrospective Overview & Key Insights

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

Published in 2020, this chronicle by @Malfunction92 details the mechanics of building a profitable, self-funded business without venture backing. Key verified financial milestone: $50/mo.

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 (183 total discussions):

JL @jldugger Peer Contributor
I tried many things. Reddit. Facebook Groups. Quora. LinkedIn. Direct Sales. Twitter. ... On the 21st of April, completely unexpectedly, a tweet of mine blew up big time.

"Fortunate favors the prepared." The highly random nature of internet karma should probably be more well publicized by now. If ten years ago, I gave myself all the blog posts I'd write over the next ten years, I would not have predicted correctly which ones would be most popular. Not that I write for the pageviews, or even write all that often. If you think of it as a multiarmed bandit problem, you kinda have to publish without a goal in mind in order to have enough arms to pull to find and iterate on the few good ones. This is why IMO, it helps to have a few input goals as well as outcomes.

AFAICT, content marketing is basically posting good stuff and hoping some of the traffic rubs off on your sales funnel. Like that Sparkfun rotary cell phone from way back when, though obviously it helps when you sell the parts to your ironic nobody-would-buy-this product online.

I smashed my infamous $500 MRR goal. It was a huge mental barrier for me. The sad thing is that once again I was tricked. I was chasing this goal for more than two years, and now it means nothing to me. It's dead. Cold. Meaningless. Like it was never there in the first place.

Elsewhere on his site Alex describes his goals as 'humble' but that may be part of the psychological problem here; even he believes they're not the same as even modest success. $500 MRR feels meaningless because it _is_. Why does 500 MRR matter? If you borrow the OKR framework, perhaps he would reframe the Objective (goal) as 'build a business capable of sustaining my preferred lifestyle', and then the MRR target would have meaning as a key result?

The Objective/Key-Result framework provide two major benefits:

First, it gives you the means to tie your metrics to something meaningful, and the ability to fact check your assumptions. Make more money isn't necessarily meaningful, but 'quit my day job' or 'send my kid to art school' can be. Perhaps the $500 MRR goal feels meaningless because the lifestyle goal _is_ the real Objective, but the $500 MRR Key Result is insufficient to meet it.

The second thing it does is provide a process for breaking Big Problems into smaller ones. You'll probably need multiple strategies to reach any important Objective, and the KRs help you break them into smaller steps. Which themselves can be treated as Objectives with their own KRs. Using https://stripe.com/atlas/guides/business-of-saas#the-fundamental-equation-of-saas as a guide for how to break down the 'big number' can help, but there is no predictive formula for maximizing it.

TH @thisisbrians Peer Contributor

So, I checked out Cyberleads[1], and...this dude is just literally (and brazenly) selling a list of startup executives' emails without their permission or consent. Not sure if that's even legal, but it's definitely scummy, and I hate when I get cold (and frequently, also technically SPAM) emails like the ones this guys is enabling.

Here's a direct quote from the site[1]:

``` Every day, we scour the web and find every single startup that just raised money. We collect information about these companies, like revenue, size, LinkedIn and Twitter profiles, CEO information, emails, and much more.

We then further investigate, and verify manually every entry on the list. Every single data point is checked, every single email is verified. Manually. By a human.

``` 1. https://www.getcyberleads.com/

Edit: added quotes.

RY @ryanwaggoner Peer Contributor

I like this. I like the writing style, I like the humility and the openness, and I like the recognition that chasing goals is ultimately an exercise in futility. You spend almost all your time unhappy because you're not yet at your goal, and then as soon as you achieve it, you're unhappy because you're not at the next arbitrary goal. It's madness, but it's basically the way almost all of us live.

I've been spending more time meditating and reading about mindfulness recently, and it's helped me become aware of just how infrequently I'm truly happy and present. I can be in the most idyllic setting and situation, and part of my brain is wondering how I can improve it, or what I can do to feel that way all the time, etc.

Why is it so difficult to turn off the past- and future-oriented parts of my brain and just be? To just enjoy this?

MI @michaelbuckbee Peer Contributor

This is going to sound weird but there's this great interview with Seinfeld and Obama where they talk about the "answer" to "why do you keep doing this stuff when you're so successful and have 'made it'"?

Which I think is the real question OP is asking: "Why if I've hit this goal do I keep doing this? Why does it feel so unsatisfying?"

I've linked to the spot in the interview but the answer is to really enjoy the work and the process.

I feel this myself (as someone with a decent sized SAAS), that I still really enjoy helping people, answering support emails, getting on calls with them. It feels more satisfying than arbitrary revenue goals.

https://youtu.be/UM-Q_zpuJGU?t=884

EN @encoderer Peer Contributor

There is sentiment that goals are bullshit and somewhat destructive. My take is, it comes down to setting the right goals.

I've bootstrapped a moderately successful SaaS and have enjoyed many revenue milestones along the way but those were milestones not goals. The goals are lifestyle based. Things like "I want to never have another traditional job" or "I want to be debt free" are much more powerful than "I want to hit $2000 MRR".

That said, look, building and selling things is amazing and I suggest everybody do it. If you only have a little time, build small things and sell them cheaply. But there is a self empowerment that comes from creating your own income that has an impact far beyond the actual dollars themselves.

Congrats Alex, good goal or not, it's a notable achievement.

HISTORICAL ERA Pandemic Bubble (2020–2022)
COMMUNITY SCORE ★ 236 points
TOTAL DISCUSSIONS 183 comments
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