Ask HN: Leaving my job to boostrap my projects. Advice?

148 points by welpwelp ↗ HN
Hello HN! I've decided to quit my job to boostrap my projects à la IndieHackers. I don't want to raise money and I only have a few $k. My plan is to build everything myself, using a stack such as Python/Django + HTML/CSS/JavaScript + eventually iOS, and the initial goal after validating my MVPs is to become "ramen profitable."

Levels has been greatly inspiring to me and I've read most of his blog and work about NomadList. https://twitter.com/levelsio

I'm going to go with the flow and figure out and learn things as I go, so my question is whether there are any advice you can think of (release on Tuesday?) that could possibly save me time, money, and mistakes.

Let me know if knowing what the projects are about, but they're basically simple services with niche userbases (e.g: Squarespace for photographers and Slack for gyms)

Thank you HN!

144 comments

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My advice is to not build Slack for Gyms, build XXX for everyone and go to market with an early niche that finds your software useful. Why limit yourself? Only other advice is to find clients that both have money and have an obvious problem. Don't try to sell to visible companies that you interact with all the time like a little restaurant. They don't have the income to support you. That military contractor that insecure, out of date site that looks embarrassing they are your target market. They don't bat at eye at a $10k invoice if it helps them make more income.
I believe superniche is good.

If you dont hate your job, I would suggest you to stay in your job until you validate your idea. It allows you to keep earning money while you are not actually building anything (validate an idea is not a fulltime job). And also it helps to keep you in the right mental state that your first idea most certainly isnt the right idea.

If you quit your job with an idea in mind and the plan of validating it then executing, it will be much harder to change or even discard this idea ("this idea is why I quit my job afterall!").

Validate your idea (with or without a MVP) before quitting your job. That's my two cents

Thank you for your reply! I have tried to keep my job, but working a 10am/7pm job with a 90mn commute everyday left me with only the weekends to work on something else. Also it's become harder and harder to get up everyday to spend the day working on something that does not wholeheartedly passionates me. Hence the decision to quit.
Then go for it, quitting your job seems the right decision for you.

Just pay special attention if you are moving forward with an idea because the market, your customers are saying so. This is the only valid reason. All other possible reasons are probably pushing you to the wrong way (inertia, a gut feeling that this someday will be huge, people that are not customers nor remotely potential customers giving you positive feedback, to occupy your mind as you have nothing else to do, to take advantage of a tech stack knowledge you already have, etc)

Work in your side-project in a regular basis, 10am/7pm. You are always in front of a computer, anyways.

Don't throw away a comfortable situation thinking that you are running after a dream because you can finish without both of them (and this happen with the most of us). I'm much more happy now that I found another good job than when I left the last one to become a digital nomad.

Most employment contracts have clauses to the effect of "anything created using company tools or company time is owned by the company". If there isn't a clear dilineation between your work hours, work location and equipment you could get into a contentious situation. (I'm not an attorney but I recently consulted with one for this exact reason.)
Here is the thing:

You will lose motivation to work on your project. It will become so boring and tedious that you will want to quit. Businesses are 90% boring. If you can't hold a boring job before validating the idea then you will run into trouble. Don't quit or find another one that sucks less.

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Look for a mediocre job that pays less, is closer to home, and has a lot less responsibility. This can free up some time for working on your side project and not leave you in such a vulnerable position.
So your job takes up ~11 hours of each day with your commute. Get a closer job. A few thousand dollars is not enough to survive on.

> Also it's become harder and harder to get up everyday to spend the day working on something that does not wholeheartedly passionates me.

Most people don't like their jobs. Most people hate their jobs. Go to work. Get money. Build a business at night and then leave.

If you blow through your savings and/or retirement in six months you're just going to end up in a worse position overall.

Do not rush important decisions. Explore options for a better job first. If you get 5 decent offers in a week jumping off may be much less risky -- it shows you can come back to a regular job pretty easily.

And build up your cash cushion. If you do try to bootstrap your project you want to be able to dedicate your time to them, not be stressed about how to pay for your next meal/rent payment.

you should definitely find another job, first.
There you go! You have 90 minutes / day to work on your side-business!
There are three things I've done that have personally helped me progress on my project.

First, I always took Sunday to work on it. Which is harder than it sounds because friends and family want that day. Eventually they'll pick up on it, be consistent.

Second, to help with the commute problem. I decided to dedicate an extra 30 to 60 min after work, before my commute to work on it. You're already at work, you're already forcing yourself to accomplish tasks, why not tick on task off for yourself before you hop on the road? I found that a lot of weeks this made me more productive than working Sundays as it was less likely to result in a few hours of web browsing. (I'm hungry and it's only supposed to be 30-60 min right?)

Third, if you dread waking up in the morning, that's usually the point where I will draw the line and get another job. It will seriously help you out if you're not stressed so much about your day to day work.

I get it, I feel your struggle man. I wish you the best either way, if you do quit, you owe us an update on how it panned out :)

It sounds like you are just upset with your current job. But bootstrapping a business will be even harder then what you describe and possible without any financial gain.
How long is your runway? Try to get your projects to revenue as soon as possible. If you can, perhaps you can do consulting work on the side to slow the burn.
Just my two cents, hire somebody else to finish the product. Pay them less than what you earn in a month and pat yourself on the back.

Spend your time on building the business (getting customers, building a brand name). That's hard enough IMO.

Have you thought of contracting or getting a remote job instead? I think one of the other posters had the best advice, which was to contract while you get validation that your idea can be a business, and then cut back contracting hours in favour of your own project as it gains traction.
Have you thought of contracting or getting a remote job instead? I think one of the other posters had the best advice, which was to contract while you get validation that your idea can be a business, and then cut back contracting hours in favour of your own project as it gains traction.
Unless you want to take time off regardless and have plenty of money to burn through, I'd save leaving your job until you are already making money with one of your projects. You can get pretty damn far just working on projects in your spare time.
You move a mountain one stone at a time. I strongly recommend that you find a way to create structure for yourself and make (meaningful) bit of progress coding daily. Set goals and deadlines early and measure yourself against them. You're on the clock (limited cash to burn through) so it's important that you avoid rabbit hole ideas and "fail quickly". Good luck and send HN your work for us to test out and provide feedback.
I like that idea and will keep you updated with progress. Thank you!
The fact that you are replying to the comments about how to make progress and keep coding, while not replying to some of the other kind of comments, is actually the biggest red flag. Coding is not going to be your biggest problem.

Of course, it's possible you'll get lost in the weeds of some framework or scaling something that you don't need. I can tell from your replies that you get this and you understand you have to ship. Let's assume you got that covered.

The real danger is that you will ship, and only then you will discover nobody wants to pay for what you built. From your pattern of replies, I suspect this is what is going to bite you, and it's why you shouldn't start with code at all and you shouldn't have any expectation of finding revenue before your savings run out.

Anyway, as others have said, whether you take the excellent advice here or not, either way you will learn a lot by trying!

I'm actually spending a few days to build tools to validate an idea, and not building even an MVP yet. Thank you for your feedback!
I think you should become ramen profitable before quitting your job. When I quit my side-business was doing $1 million in revenue. I only quit because the work load from customer support had become impossible to deal with on evenings and weekends.
Oh wow, what industry / service you did as a side project?

I can't imagine keeping my job once I start to make more on the side than doing something full time. Maybe there are that cool places to work, but I haven't seen any so far :)

I don't want to out myself but it's a boring business which is tailored to a very specific local market. Think legal stuff that only applies to a specific country.

One of the reasons I didn't quit earlier was because I loved my old job so much, the company was exploding and I was a key player. I also had nice stock options (with pre-emption).

Wow! Did you have a team when you were 1Mn in revenue!? If not, what was your side business?
No team. Just me and my co-founder. I don't want to out myself but see the reply to the sibling comment.
$1M in revenue and you're doing so much customer support yourself that that's the reason you quit the day-job?
$1M in revenue, not profit. Customer support in this case is dealing with a high-profile customers. A lot of legal stuff and writing important emails. Not something I can easily outsource away.

The technical backlog is huge as well but most of the business critical stuff has already been implemented so yes, the bottleneck is support.

I wasn't thinking outsource it, I was thinking surely your time's (literally) worth more than it would cost to hire a support person.

(But of course, you know your company; I don't :))

Validate first, build later.
I've decided to quit my job ... and I only have a few $k

I don't know the specifics of your situation, but this seems like a really bad plan. Usually when I advise people who are about to start contracting, I tell them they should have 3 to 6 months of rent before they start; contracting is much more of a sure thing than building Slack for dogs.

Yes, bootstrap at night while paying the bills during the day. As your side project starts to make money, contract less.
I will never quit my job without having better signals of profits from your project. My second advice is methodologies (e.g. release on Tuesday?) don't matter when you don't have a business.
Spend at least one hour every day on sales. Starting now.

Coding is the easy (and natural) part. In my experience, sales has been harder than I expected. Even when people love the product.

Jerry, this is your landlord speaking: please don't quit your job!
> I've decided to quit my job to boostrap my projects à la IndieHackers.

I did this and it was fun and everything, but I never made a single cent. I did grow my personal network though :) If you value learning from others, keep your job and only quit if you make at least 50 to 75% of your salary AND you see constant growth.

> using a stack such as Python/Django + HTML/CSS/JavaScript + eventually iOS

Another red flag. Technology doesn't matter and the fact that you mention this instead of business validation you should think twice before making such a commitment.

EDIT: I forgot to add that the technology part is at most 10-15% of it. The rest is boring marketing, tons of spreadsheets, Google, Google, Google, Email^n, more spreadsheets and business operations if you are lucky.

Another one that quit his job to bootstrap own projects, and only made some 100 Euros from them..

It is hard, really hard, and I even had some kind of a business plan. But one thing is sure, you'll learn a lot about yourself from the process.

I'm now teaching CS classes on a local university.

> "...Technology doesn't matter..." <

Key point this one.

>> Another red flag. Technology doesn't matter and the fact that you mention this instead of business validation you should think twice before making such a commitment.

This is a very, very true. I also did this, quit to work on a side project for about 8 months (2008). I wrote a lot of code, but in the end the project had a couple of hard problems and the market was a small number of large corporations. When I finally realized this, and ran the numbers, I discovered my folly. That and I found myself web surfing all day instead of coding. Went back to work.

Next project (2011) I also didn't validate the market, but kept working, it never launched. For my third project (2016) I launched but didn't validate the market either.

What have I learned? Validate the $#@!ing market before writing a line of code! I'm still trying to figure out how to do this however.

Talk to clients first. Say "what's are some problems that are stopping you from making money, I want to help you solve them and I'll only bill you if it works". You don't have to say that to too many companies before you find a problem that isn't just unique to them.
Ah this is a very good idea. I had always wondered (even as someone that's started a couple of businesses before) what would be some practical, efficient, useful and free (beer) ways to probe for market opportunities, and this seems like an excellent method.
Creating something other people will pay money for is very very hard. 90+% of projects are ignored and forgotten.

I've had two successful projects over 10yrs which is about average.

I feel the general advice is don't do it and with good reason!

However, I feel that if you have good skills this should be the way to go. Hustle and get profitable. It is not that difficult using services.

The moonlighting alternative sounds appealing but I find the progress to be extremely slow and there are just too many distractions to really make it useful.

I know there are people who do it successfully, but I feel they are supermen and a notch above most.

Just my 2 cents.

Thank you! It seems from all the feedback that I'm significantly against the odds, but I really want to give it a shot.
Context: I quit my job in June 2016 to take a break from my career and among other things, build a product end to end. Money has run out now but passion hasn't and I'm close to first launch. I'm in Bangalore so I'm able to keep burn rate below $400/month.

Advice: I'd say go with the tech you know(exceptions only apply if your core differentiator is technological superiority, but that's rare). You'll have full days to yourself, so separate work time from leisure time, do physical exercise, be in touch with friends, don't reveal your plans/progress to many people, involve target users as soon as possible(most important). Lastly, enjoy the ride!

It sounds like you've missed a key piece of advice somewhere along the way: Don't quit your day job until you have something replacing its income.

I live off the profits of a few bootstrapped SaaS products. It took six years before I was bringing in enough to comfortably live on.

If it's not too late, switch the "build a product" and "quit my job" steps around into the correct order.

> I've decided to quit my job

Don't.

Lower your overhead. Reduce your rent - $0 would be ideal, if you have a car, consider selling it or replace it with a super cheap one. I bootstrapped for 10 years, and I did make some money along the way. BUT, I spent too long trying to make it work. Make sure you don't hang on too long. Give yourself a deadline for when this thing should be self-sustaining. Understand UPFRONT that taxes are going to suck up every penny you have. You are no longer a W2 employee, make sure you understand the difference taxes have on a business owner and a W2 employee.
> Levels has been greatly inspiring to me

Thank you! <3

> I've decided to quit my job to boostrap my projects à la IndieHackers

To anyone else: DON'T DO THIS.

First get enough cashflow from your side project to sustain yourself (e.g. $1k/m to $2k/m if you're single, without kids, in an average city). You will burn yourself out if you don't have cashflow. Savings is nice but cashflow is better, because if it runs, it probably keeps running. Savings, you run out.

It took me YEARS to get anything substantial off the ground on the internet. You can't just quit your job and expect to get money within months. It's not smart. Consider going back to your job or getting another job and keeping the cashflow from that. Then work on side projects in your own time and quit when it makes enough money.

Seeing all these product makers on Twitter etc. they make it seem easy but you don't see the intense battle they had to go through for years to get where they are now. It takes time and lots of it! I was making sites since I was 10 and my first site that made money was after 10 years! Not that money was my goal when I was 10yo, but still. You don't realize people's histories.

I bankrolled Nomad List (https://nomadlist.com) in 2014 with my YouTube channel (https://youtube.com/pandadnb) that made $2-8k/m from 2010-2014. When Nomad List started making $5k/m, I stopped working on the YouTube. I bankrolled my YouTube channel in 2010 with a a terrible blog about ASUS tablets (http://asustablet.com, see screenshot @ http://dig.do/screenshot-hires/201310/asustablet.com-transfo...) that made $500/m. I bankrolled that tablet blog in 2009 with being in university and getting $200/m college subsidy from the government since 2007.

My point is, you can keep stepping up and bankrolling the next project with cashflow from your previous project. That way I've never had to do ANY freelance work or get a normal job EVER.

> My plan is to build everything myself, using a stack such as Python/Django + HTML/CSS/JavaScript + eventually iOS, and the initial goal after validating my MVPs is to become "ramen profitable."

Great choice! Avoid frameworks like Meteor, React etc. they're a rabbit hole that will paralyze you from shipping and getting to revenue.

My simple stack is:

Client: HTML, CSS, JS with jQuery (JS talks to server API via basic AJAX requests), CodeKit (to compile + minify my JS and CSS)

Server: API written in PHP that connects to SQLite and Postgres databases (just a better version of MySQL)

The client stack (HTML, CSS, JS) is mostly same for everyone, the server stack you can also do in JS, Python, Ruby or whatever server language you like best.

> + eventually iOS

This stack has the benefit you can easily build an iOS app that just connects to your server API. Now your iOS app is simply another client app.

I'd recommend AGAINST learning iOS in your first year, as your time is limited. And even with Swift, it's a rabbit hole.

You want to get to cashflow as fast as possible to avoid burning out and running out of cash, so focus on revenue. The web (vs. native) is I think fastest way to quickly acquire money from customers.

For payments, use Stripe.

Good luck!

> Avoid frameworks like Meteor, React etc. they're a rabbit hole that will paralyze you from shipping and getting to revenue.

I agree with the part where you say to avoid tools that don't paralyze you from shipping and getting revenue. On the other hand, I think that if someone is fast and productive with React or Meteor, that is the tool he/she should be using to build anything.

Yes, absolutely. Always use whatever is fastest for you.
I would also like to add that you should get to mvp as fast as possible so that you can charge for whatever you've built.

I think a lot of devs focus too much on coding and not enough on revenue. Make sure the feature you're adding has value, or else you're just wasting your time.

I also made the mistake of using the project as an opportunity to learn new technologies which is dangerous because it can eat into the time it takes to ship.

Agreed, I've done that too before : )
Thank you Pieter!

I feel honored by your reply : )

I unfortunately do not have any previous project to bankroll from, but this will be the first one!

The stack I mentioned is the one I use best, which is why I picked it.

Fortunately, I have been doing iOS development for the past ~5 years.

I'm going to validate my idea and move forward to a simple MVP if it works.

It all feels very uncertain but I'm going with the flow and will see what happens!

I don't know what you do at work but if I were you, I wouldn't do that. Not because of money, but because you need something that motivates you and gives you the feeling of accomplishing things.

I'd like to quote this:

- 80% of your time goes to low-risk/reasonable-reward work

- 15% of your time goes to related high-risk/high-reward work

- 5% of your time goes to satisfying your own curiosity

Read this twice: https://www.facebook.com/notes/kent-beck/fresh-work-80155/11...

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Having done this (/ currently doing it), I would say: follow your heart.

Taking time off to nurture your own projects is a fine and reasonable personal endeavor, but not necessarily an optimal business or financial one.

In many ways, the time and space can help you explore and expand your ideas into something in the middle of the venn circles between "your happy with it" and "the market is happy with it".

But, don't expect to be done with day jobs after burning through "a few $k".

Depending on where you live, and who's in your network, you may be able to move to part time, agency, or freelance work after burning through your runway in order to keep enough time to work on your thing.

My operating assumption with all of this is, your current day job is preventing you (in one way or another) from focusing on your own projects. This is ok. Not everyone can handle burning the candle at both ends with the day job and night-work. Figure out a way to make space for both until the personal project becomes sustainable.

Beyond this, the other advice about 10-15% tech and validating your idea before hitting the code is solid.

I have a single-time-purchase iOS app in the App Store, and a month or two after releasing the app, spending one day investigating blogs and websites, and one day sending tuned press release letters to them did more for my sales than any new feature I could have designed or coded in that amount of time.

1. Don't quit your job if you can't live off savings for at least a year. Having a job allows you to have a safe base to experiment ideas without the burden of making profit.

2. This is business, forget about the tech stack you are using or finding the perfect tool. Your main goal is to create value and make someone's life easier. My advice is to use the tools you are most familiar with, this will allow you to be productive without worrying about things like "which chart library is the best for Angular 2 RC 5". There are successful business that started out with a spreadsheet.

3. Be aware of survivorship bias. While Levels apparently succeeded bootstrapping many of his businesses (and I think he did), there are hundreds of other people that you'll never hear the name of who failed miserably and wasted many keystrokes on launching a failed product.

4. "Perfect is the enemy of good". Ship things fast and don't be afraid of doing things that don't scale like processing payment, hard coding a few things (if you know what you're doing) and even calling users to get a feedback on your product.

About #1... If you're going to work in the same field while trying to start a company it's important to have your employment contract reviewed by an attorney. Intellectual property rights can become contentious if your business starts making money.
I see, thank you. This is another reason why quitting my job makes this easier.
I see, thank you. This is another reason why quitting my job makes this easier.
You should have at least 18 months savings of your expenses + expected business costs. That's least runaway you need to get ramen-profitable if you do it alone and not planning on raising any money.

If not do, do some freelancing, part time job, whatever you need not to run out of money.