BOOTSTRAPPING ★ 76 upvotes 2021

We've been running a bootstrapped startup for a year

Retrospective Overview & Key Insights

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

Published in 2021, this chronicle by @artembugara 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 (41 total discussions):

JU @Jugurtha Peer Contributor

I like it. I'll expand a bit on the following point:

Be a consulting company

We've been a consulting company for many years, and we built bespoke machine learning products for enterprise from varying sectors and industries. Through these projects, we've had many of the problems people in the field are having, and then with that experience, we built our platform to solve them.

I tweeted a small thread https://twitter.com/jugurthahadjar/status/1310668293305499653 with small pointers for people who might want to do it. Sometimes people post an Ask HN wanting to go freelancing, the twitter thread argues for creating a small consultancy and selling to enterprise instead of doing it as an individual, because of many reasons. It then explains how to extract patterns into a product.

Twitter thread:

0. Form:

0.0. It pays to provide services through a company. Companies write large checks to companies without blinking; not so large for individuals.

1. Contracts:

1.0. Get a lawyer to prepare contracts for collaborations. Someone at some point might disagree or have trouble remembering what they have agreed to pay you, make sure to have a mnemonic device in the form of a clear contract.

1.1. Companies have typical contracts for collaboration: don't sign anything without legal counsel.

1.2. Retain intellectual property to amortize engineering and sell what you make to others.

1.3. Companies might ask that you do not sell to competitors: define them and contain geographic zone and duration. Get paid for the opportunity cost.

1.4. Split project into tranches for which you get paid. This can help cash-flow and reduce risk, especially in the beginning.

2. Presentation:

2.0. Your company solves problems and being open minded about these problems is useful; so it's not much about finding problems for your solutions, but more like finding solutions to clients' problems.

2.0.0 After enough problems you built solutions for, patterns emerge and you can abstract a solution that serves several use cases. See "Abstraction" section.

2.1. General presentation with broad strokes of your capabilities, including previous work with other clients

2.2. Conversation with the prospect on their worries in a given space

2.3. Conversation with the prospect on their worries in a given space

2.4. Extract problems from that conversation and send a list of N problems to solve/ideas to explore.

2.5. The client finds one problem urgent/highest priority/highest value

2.6. You get together and talk about "desirability, fasiblity, viability".

2.7. Once you agree on what to do, prove the concept.

2.7.0. e.g: organizations give us data and ask us to predict something, say customer churn or subway car malfunction. We return predictions, they validate the predictions, and we can then start the project because they have proof we actually can predict what they want us to.

3. Execution:

3.0. Your opinion on what is valuable for the client does not matter. It doesn't have to be valuable to you, only to the client. A client who gets excited by a functionality that took one hour to implement because it solves a real problem is a learning experience.

3.1. Go above and beyond. Some sectors/clients are hard to get in, but once you're in, you're in.

3.2. Listening and assuming the client is smart goes a long, long, long way.

3.3. Send meeting notes to the client. It clears ambiguities during/after the project.

3.4. Press to get the client's domain experts' collaboration. They will actually use what you're building. Get them at the table.

3.5. Some of the most valuable insights are gleaned after a meeting and not necessarily with your "counterpart".

Don't build the wrong thing.

4. Abstract:

4.0. When you solve many problems, some patterns emerge. You built custom products for your clients, but you can abstract functionality and build tooling to scale your services, and enable others to do the same.

4.0.0. e.g: we we built machine learning products for enterprise clients. After many projects, we built iko.ai, our own machine learning platform to "Get Data Products Released".

4.1. One advantage of this approach is to explore the space while being profitable. Some problems exist not for lack of a nice front-end or lack of knowledge of the target audience. Coming at them from a purely "webdev"/"devops" mindset can bring bad surprises.

All the best,

== End thread

AC @acwan93 Peer Contributor

This is a great list. I’m taking over a bootstrapped family business, and a lot of what you wrote echos the founders’ (my parents) sentiment.

2. Do not think you/your product/your team/your approach are any different or unique

I have a hard time struggling with this, especially as I’m trying to SaaSify the business and see a never-ending list of competitors and substitutes out there. Maybe that’s being too product focused, but I’m curious to see how you got past this. I think there’s non-product aspects to consider (support, pricing, etc.)

6. Do not be afraid to charge
8. Only those who pay you money have to decide which features to add

These two are so true, and my parents say this all the time. So many prospective/existing clients express interest in a particular feature, only to never follow through with committing to contracts or paying anything.

They usually come with the excuse of one of the three buckets:

-The product should’ve had feature X to begin with

-They’re willing to be a guinea pig to beta test feature X in exchange for the whole product to be free (not a discounted price) since without feature X it’s a dealbreaker

-They can’t afford the price and we’re charging too much

For the latter, we’ve done price analyses across similar products online and found that our price points are competitive, so we can (usually, if the salespeople of our company have backbone) push back.

It reminds me of telling artists and graphic designers to do work “for exposure”, to which I really want to reply with the Goodfellas reference of “fuck you, pay me”.

9. Carefully choose co-founders

Corollary: NEVER choose your spouse or family members as co-founders. I can’t speak about friends as I don’t have personal experience, but the personal and professional get really intertwined even if both sides try to set boundaries. My parents and I still get along fine, but I just don’t like having the burden of mixing professional and personal.

11. Things that no one actually cares about at the beginning

In my experience (which is very likely wildly different), I find the logo and the founders’ background to be important. With our clients I’ve found that I had to name drop a couple times on my background (ex-FAANG) or pull the nepotism card several times to close a deal or reassure a client. A new logo and a new UI also gives a great first impression to our existing clients who’ve seen a 90s style UI.

ID @idlewords Peer Contributor

Congratulations to anyone making even a modest living after one year. That said, I don't understand the section on investment here. The framing is that the startup is bootstrapped, and they don't mention taking any outside investment, and yet they're offering advice on how to approach investors.

The product is also quite expensive ($400 and $700 monthly tiers). Nothing wrong with that either, but the sales experience will be quite different at that pricing level, and having fewer than ten clients limits the number of useful lessons you can draw at this point.

The meta-point is that trying this teaches you some useful lessons, but also exposes you to a lot of randomness (lucky and unlucky) and it's easy to overanalyze that, particularly in early days.

I think the 2 year post will have much more meat on its bones, and wish the authors every success.

DI @diydsp Peer Contributor

I took a year off to start a business and failed. The only thing missing from this list is a sense of how brutally true it is.

As brand-conscious consumers, we swim in daydreams of products and images. "What if BMW made a blender?" But these are playground thoughts. As soon as you want you more than $100 to put something in someone's hands, they vanish to reveal the switchboard of a different system altogether :)

My notion of a craftsmen or artisan doing what they love and getting paid for it is 100% out of touch. It's all about making others have $ by them giving you some of theirs temporarily. No romance or individuality. Save those expressions of personality for the consumer choices you make. Unless you happen to be launching a reusable rocket. Then you may get to choose the payload :)

AL @allendoerfer Peer Contributor

I would add some sort of address to the website, pricing in Euro (or some description how rapidapi handles billing for you). As a European, I would be much more willing to buy something from you, if I would not have to switch to Linkedin to see that you are from Paris.

I think it would give you a little edge in Europe, because people would guess, that you probably know how VAT works. It would also help you get over the small company trust issue, since we would actually have a chance to sue you, in case something goes wrong.

I do not think, that it would cause you harm in the US/rest of the world. I guess it would slightly help there, too. At least they know, that you are SOMEWHERE, even if you are not in the US.

HISTORICAL ERA Pandemic Bubble (2020–2022)
COMMUNITY SCORE ★ 76 points
TOTAL DISCUSSIONS 41 comments
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