BOOTSTRAPPING ★ 62 upvotes 2023

Bootstrapping to €600k MRR and getting killed by Shopify

Retrospective Overview & Key Insights

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

Published in 2023, this chronicle by @ericthegoodking details the mechanics of building a profitable, self-funded business without venture backing.

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 (30 total discussions):

LE @leteyski Peer Contributor

Hello everyone, I'm the founder of Checkout X and the original post creator - so flattered to see all the engagement here. Thanks for the kind words and the criticism, I totally respect everyone's opinion on the topic. I intentionally waited a couple of years before I wrote the post as I just wanted to share the story of Checkout X for people to see it - without any agenda. Checkout X is a closed page for me and I'm looking forward towards the future.

Some updates from me: - I built another Shopify app ( Vanga AI ) that got acquired this year - I've summarised my thoughts on the current Shopify ecosystem in another blog post: Why I'm leaving the Shopify apps business ( https://www.leteyski.com/why-i-m-leaving-the-shopify-apps-business ) - I've summarised some of the business lessons I've accumulated into a Startup assessment framework called: The Dead Horse Framework ( https://www.leteyski.com/the-dead-horse-framework )

IV @ivanmontillam Peer Contributor

My 2 cents here: It's not always too bad or weak to assume some platform risk to make some business.

Just always keep in mind that, it's not forever and that you should preserve some of that piggybacked money for less risky endeavors. I think business that are mounted over a giant, whilst prone to be killed anytime, can be used for a quick buck[0] as part of a larger plan. In this case, the author was aware of that, but more fore-thinking would have helped.

For instance, I leverage Telegram bots to make some business, but I'm ready for such an scenario where Telegram, decides:

- To make its API paid.

- To copy the features of my bots into product features.

See what happened with Reddit's API. WordPress purchased WooCommerce and it became a happy story, but it could have gone wrong and become a horror story where the purchase could have not happened, and WordPress gone into destroy mode.

I tread lightly.

--

[0]: Do not conflate "quick" with "easy" in this context. The faster, the harder it is.

AT @atourgates Peer Contributor

An interesting take. The only bit I strongly disagree with is this:

One advice we got was to file an antitrust case against Shopify in a European Court.
Theoretically, we could’ve argued that Shopify uses anti-competitive practices to get rid of their checkout competition. Similar to what Spotify & Epic Games did against Apple.
While that might’ve been a viable option, honestly, I don’t have the balls to pick a legal fight with a multi-billion corporation.
On top of that, I believe that crying to the regulator is a bitch move. After everything, I still believe that Shopify built their platform and they should be able to do whatever they want with it.

I have no insight into how the EU's competition laws would or would not apply here, but that's literally the regulator's job, and it's certainly not a "bitch move" to hold companies accountable for anticompetitive behavior (if that's what's happening).

LO @lolinder Peer Contributor

The author set up a business in what they knew was a gray area. 6 months later the ToS were updated to explicitly ban what they were doing, and they got an email that pretty clearly implied that they would need to make major changes but wouldn't be shut down right away, but the author chose to interpret silence as authorization to keep scaling. About 8 months later Shopify's COO told them explicitly that Shopify didn't want them to keep operating, and the author used a technical detail of the way they phrased the ToS to justify continuing to scale.

At that point I lost all sympathy for the author. The COO of the company you've built your product on told you that they don't want you to keep running your business. At that point they shouldn't have to keep playing whack-a-mole with loopholes in the ToS, and the fact that they did does not speak well of the author or their company.

BR @brianwawok Peer Contributor

Well, I can relate as I just got an email that Shopify changed their partner TOS today because of me.

They had demanded that I add a negative keyword "Shopify" to all of my Google ads.

I declined, because - it wasn't in our partnership agreement and I in fact DID want clients who used Shopify to find my business. (I am in the e-commerce space selling a product that works for many marketplaces including Shopify).

Just got an email today about a partnership TOS change. Now I need to put a negative keyword in any Google ad campaign they deem it necessary, despite like I said, Shopify users being great product fits for me.

I am just a little dude. What power do I have? Not really anything, the biggies get to tell me what to do. I either follow the rules of the game or get banned from the platform. Rather frustrating to say the least.

HISTORICAL ERA Post-ZIRP & AI (2023–2026)
COMMUNITY SCORE ★ 62 points
TOTAL DISCUSSIONS 30 comments
TOPICS & TECH STACK:
More Retrospectives by @ericthegoodking