Ask HN: How and when did you decide and start your startup?

52 points by talhof8 ↗ HN
I've been thinking quite some time now about making the move of quitting my fulltime job as a software engineer, and pursue my dream of founding a startup.

I'm 23 y/o and don't have much to lose really (except rent), and yet I'm still STRUGGLING to just make that move and start.

I'd love to hear your stories about when and how did you decide to do it? How did you start? How was it going to sleep knowing that you probably not going to have an income in the next upcoming weeks/months?

41 comments

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Just start it. Asking and reading others' stories is just another delay in starting. You don't have to quit, you can start working on it and if you continue to stay passionate then eventually make it your full-time focus.
it will be more difficult to do later when you have a family and when you are on mortgages.

It is also more difficult to convince a friend to become a co-founder when they have mortgages and a family.

I'm 41 and just started working on my thing a couple of months ago. I'm married but we don't have kids nor a mortgage because we've been digital nomads for the most part of the last 10 years. My wife is doing well economically so we decided together it was a good time to start working on something that will not generate income in at least 2 years.

After 20+ years in dev I got tired of making projects for others and finally decided on an idea that could work financially. Not to grow to millions of users, but to at least support myself.

I couldn't start anything from scratch so I bought the damn thing. That was my MBA. If I failed, I would consider it a sunk cost of education. People spend 100K on a good MBA. I spent less than that on the business I bought. Happily running it for 6+ years now with a bootstrapped team of 15 of us. Ok, some advice now:

There are 3 ways:

1. Join a startup and go from there. Learn how things work in the startup world. You are only 23. It wouldn't hurt to work for a startup for 2-3 years and you may get somewhere after that.

2. If you strongly believe in a specific idea, then try to execute on it now. Like you said, you don't have much to lose. What an awesome position to be in. However, you will most likely fail based on statistics and the fact that you don't know what you don't know yet. You are 23. You have to learn a lot of things in the world.

3. Buy an existing business like I did. This obviously requires capital but you could buy a small say 1K MRR SAAS product/side project. You will have some things already setup at a small scale and you can go from there. Very hard though for someone who has never run a business BUT frankly, this is one way to force yourself into it.Think of the capital/investment as the cost of an MBA.

I would say 1 is the easiest, 3 is easier relatively but needs capital and 2 is the hardest.

Also, don't beat yourself up for not being able to start. Instead, find out what you can do TODAY to get to that destination of doing your own thing. If that thing today means joining an existing startup, do it. If that thing today means hanging out with similar minded folks who are already doing this, do it. If that things today means learning how to code, do it. Do something TODAY. How do you eat an elephant ? One bite at a time. Surround yourself with people who are doing what you want to do. It is hard to find them but try. Good luck!!

What kind of business did you buy? I've been looking into that, but it's tough for me to pull the trigger just due to fear of the unknown (e.g. if I buy an ecommerce business and the supplier immediately goes out of business, will I be able to find a new one?).
SAAS business. I don't understand the physical e-commerce business so I unfortunately am not the right person for those questions.
Out of interest, how much capital would one roughly need to buy a 1K MRR? I'd assume the valuation would be some multiple of the revenue with some combination of growth rate?
If you want to check out pricing on some low-revenue businesses, try Shopify's marketplace: https://exchangemarketplace.com/. Much more ecommerce than SaaS, and there's some crap in it, but it'll give you an idea of multiples (which are very low at that size).
For very small businesses, I would generally not go beyond 2-3 years of multiple on revenue max. But there are many other factors. For example, how old is the business and what is the track record ? There is a big difference between doing 1K MRR for last 18 month vs even 3K MRR for last 2 months.

I personally want to see at least 3 years of hard work. Anything less is too risky since the business hasn't gone through the ups and downs enough and frankly it is not enough grinding for me. But thats my criteria. There may be some gems out there that are younger and still worth a look.

I have a lot of interest in the business buying/selling space and one day I will be doing this professionally :). For now, trying to grow my bootstrapped SAAS to 5 million in ARR.

Actually I currently work at a small startup (just got thru the 1-year cliff), and kind of saw it crash. Not only business-wise, but also management-wise. The shit kinda hit the fan to the point that the atmosphere got really toxic. The stuff I witnessed opened my eyes for the less sexy, more mean things happening in the tech world. It got me to worry I could easily repeat those same harsh mistakes, making me question whether it's worth it.
I started a dog treat company very recently (a couple of months ago), and it was definitely a combination of circumstance and everything I'd learned that made me decide I was ready to go for it.

On the circumstance side, I had actually left the tech industry to start a dog boarding business, but Covid hit right as I was about to close my SBA loan and start construction, so I cut bait rather than take a very large, personally guaranteed loan to start a business driven by people traveling and going into the office. I had decided to go the franchise route for that, largely to give myself the confidence that I would be able to get through all the unknowns with the backing of folks who had done this many times before.

After I called that off, I decided to strike out on my own and sell a frozen dog treat mix that I had been making for my dog. The pandemic circumstances (being at home, collecting unemployment) definitely helped, but the big obstacle for me was honestly less about time/money and more about a lack of confidence (which is weird because most people who know me would probably describe me as confident to the point of vanity). Honestly though, going through the initial part of getting the dog boarding business set up really helped - I had to deal with a bunch of stuff I'd never dealt with before (architect, permits, finding a contractor, leasing a space, getting all the various HR stuff set up to hire someone), and it just wasn't that difficult to deal with each thing as it came up. I think it helps that my background is in product management at early-stage companies, so that entailed a lot of generalist problem solving.

The other thing that helped, quite honestly, was seeing the other people in the franchise. They were, to be charitable, generally somewhat less sharp than the type of people I had become accustomed to working with in Silicon Valley, and most of them were running their businesses reasonably profitably. If they could run businesses, then clearly I ought to be able to.

I guess one last thing I'll add is that I own a few apartments in the Bay Area along with a couple of other folks, and that's been helpful both because they generate income and because that's a very small scale example of running a business (I have a full time property manager, so I don't have to do much), which is, again, a confidence builder. If you're able to start any kind of small scale business while working just to help build your confidence, that might be a good intermediate step even if you're not ready to fully quit and go out on your own.

I was doing some consulting work in an education-adjacent field for about 3 years. Was happy with the 2k MRR it was bringing in (albeit inconsistent at times during holidays etc).

A friend reached out if I could do some work for high schoolers. Kind of kismet with the move to remote education, as I started the program, significant demand for this type of work.

As a 18 years old with fresh finished mechanical apprenticeship. I started a online gaming, irc bouncer, radio streaming company with my first salary.

Why? because I found no good gameserver to play on it at this time and bought myself a physical Server to fix that.

6 months later I quit my full time job and pumped up my business. Best decision ever! I never thought about my personal income. At that time I was still living at my Patents.

As of today, I founded multiple companies and sold them successful in the 8 digits euros.

Just do it, find something you like, focus on it and believe in your self.

I quit my job at 23 to become a startup founder (18 months ago). Quitting wasn't too difficult for me. I started the job with the expectation that I'd work for a year and then do the startup. I had been spending my free time working on my idea(s) for a long time and was excited to go full time on it (I also didn't get much fulfillment from my job).

I was surprised to discover, long after quitting, that working full-time on your own ideas can come with it's own distraction: pressure to make money. Probably the biggest mistake I made from months 6 to 12 (startup idea #2) was being too concerned about structuring things in a way that would (hopefully) make it easier to charge money. I ended up spending a lot of time doing things that in hindsight weren't generating any value. It would've been much better to focus on doing meaningful things, whatever those may be.

I don't know the details of your situation, but that might be something to consider: if you can figure out a way to have a decent amount of time to work on whatever you want while still having an income from elsewhere, it might actually be easier to focus than if you were doing the idea full-time.

On the other hand, I am glad I quit myself. So maybe that advice is just BS.

For income: I might switch the "weeks/months" estimate to years ;). Running out of money hasn't been an issue (lots of savings from my job, my wife worked until recently, then we moved back in with my parents until the pandemic winds down). Opportunity cost of course is large, but that's fairly easy to ignore. I've learned an incredible amount during the past 18 months, so even if I can't get my startup to work, it'll have been a worthwhile investment.

I don't know if any of that is helpful. I'd be happy to chat if you like, my email's in my profile.

First one, was in college, didn't really understand what I was doing, got invited by a friend and I was just really excited about programming real stuff on my free time outside of school. Got out 2 years later, right before my partners graduated and really grew the company.

Second time, almost right after college, I started working as the first employee at another startup, at first it was really exciting, I felt like I was part of the founding team, contributed a lot to the direction of the company and got to work on the pitch as well as go to meetings with investors, but when the company started growing, a line was drawn between founders and employees. That's when I got together with one of the other employees and left to start our own company.

Thirds time, while running my previous company I decided to participate in a hackathon with a friend, we won the local chapter, then the global chapter and then we got funding.

Looking back, I've been extremely lucky and never really planned anything too much, things just happened. Also, if I could go back in time, I might have chosen to just dedicate myself to being a very good programmer instead of playing the startup game.

I worked a normal 9-5 job after college and knew within 3 months that it wasn't for me. I quit and did freelance work until I'd saved $100k. Then I stopped freelancing and put all energy into a startup. Having a cushion saved is the only way to sleep despite not drawing a salary. I recommend you find someone to start a venture with as it's less psychologically difficult when someone is in the same boat with you.
> making the move of quitting my fulltime job

> How was it going to sleep knowing that you probably not going to have an income in the next upcoming weeks/months?

Do you need to quit your job to start working on a startup?

When I started my company at 23, I spent a full year working long nights/weekends and then quit my day job only after the company had some momentum.

If you can manage a day job and a side hustle, I'd very much recommend that. Although if your current day job expects more than a 40 hour work week from you, that could be a problem.

I’d extremely not recommend this. Everyone is different of course, but there’s no way you can work a full time job, stay healthy, and dedicate enough time to a serious new endeavor. Don’t listen to the hustle bullshit. If you want to do a startup, just quit and jump into it.
> there’s no way you can work a full time job, stay healthy, and dedicate enough time to a serious new endeavor

I agree. I didn't stay very healthy when I was working a day job and also working nights / weekends. It was exhausting.

Unfortunately I didn't have enough savings to be able to quit my job. It was definitely a trade off.

That’s fair, and I assume it worked out ok for you in the end. I imagine people who are able to pull that off know who they are. Definitely understand the trade off.

I just think as general advice for young programmers, “work 60+ hour weeks” is very much the wrong message. Stay healthy and let your passion drive your work.

It wasn't a startup exactly, but I did part-time software dev contracting as a side hustle for about 3 months while I held down a full time job. It was excruciating. But, it did allow me to build up enough cushion to comfortably make the jump to full time contracting. Which was my best career move yet.

I really wouldn't want to go through that again, but it was worth it.

I'm your age :)

I started my current one in college. Since high school I had every intention of making a living starting my own business, so that was the plan all along. I've been on hacker news since my early teens (different accounts) and I've been doing projects about just as long.

I'm working full time on my business. If the times were different, I'd look for a part time job serving coffee or something. I went back to living with my parents after college (probably a mistake), so I don't worry about supporting myself.

By now, I am pretty good at recognizing what a good idea is, and getting from idea to shipping something. I'm working on my marketing skills and being patient.

You say you're struggling to start, I imagine there is something specific that makes you feel that way:

Do you have an idea yet? How far have you gotten? Are you afraid to quit your job? Are you having difficulties putting in the time and effort?

My startup trail started the day I decided to take the summer off from living in NYC, and go to South America for the summer ( Peru ) to learn to surf while working all day on my MVP.

That was 2006. I never looked back.

Once you get used to doing things your way.. it's very hard to go back.

Let go of the golden handcuffs, put on your adventure hat, and consider finding a low-cost city/country to play in while you figure out product-market-fit[1]. If you are lucky you will also find other potential co-founders also on the same journey, and other talented local folk who are affordable. Who knows you may even learn a new language along the way! Worst case you go back to doing what you've been doing. It's not going anywhere soon in this climate.

[1]https://remoteok.io/

Based on my personal experience (SlashMap - fairly successful Slack plugin), I’d recommend trying to verify an idea before giving up your full-time job. For instance, you can start with a landing page to do so. I must confess that combining full-time work with a side project was challenging for me and affected work-life balance heavily in my case, but it may be the best choice if you’re not ready to quit your current job. Working on a side project only in your free time will probably significantly slow down the progress, but you can think of finding a partner to help you with it (if the project succeeds you’ll probably need a partner anyways). Opinion and complementary skills of another person may be keys to success as well. I’d say that if you really believe in your idea, it’s very likely you’ll find a way to verify it before quitting your current job. Good luck!
do you have an idea you could see yourself working on for 5-10 years? If so, quit your job and make the jump. You are going to be too burnt out from having a job and working your free hours towards building a start up on the side. Not having income will inherently drive you to work harder towards finding success quickly.

If you don't have any ideas, would recommend finding some ideas you are passionate about first while keeping your day job

I started after losing custom coding business for a few years to really bad products and decided to make a product. Took about 3 years to replace the custom revenue with product revenue. I agree with all the sentiment here, you don't have to quit your job to do a start-up. You can do lots of validation
I started because I wanted to learn a new skill and I was bored watching TV etc. It was somewhat accidental. My only advice is to do something that is helpful to either you or a group of people or solves a problem that you have or others have.
I found it useful to have cofounders as forcing functions. Also, the end of the previous thing: college->first startup, finishing my PhD->YC startup, being fired->CircleCI, and running out of money->Dark.
Some of my friends asked me whether they should start a company, I typically suggest them to answer these questions first:

- Have you ever made over $10k on your own?

Not from your day job salary. Not from public stock market. Making money needs practice. You start a company to make money. You’d better have some experience of making money first. Without working in an established company, are you able to make a meaningful amount of money and survive in this world?

- What’s your longest project?

Have you worked on anything for multiple years? Grit & patience need practice. Building a successful company takes multiple years, even decades. Be prepared.

- When was the last time you were insulted by others?

If you grew up in a very comfortable environment (rich family, great schools — because your parents went to those great schools too, great companies, …), probably you already get used to compliment for your entire life. Now you are going to face a very very diverse set of people who don’t know your family background or don’t recognize your family name. If you are the kind of people who are easy to be upset by very minor things (e.g., people don’t reply your email or people don’t compliment you), you’d better stay in the friendly corporate.

- What happened when you broke up with your ex or your friends?

People relationship is complex. You’ll experience a lot of bad people relationship if you start your own company — breaking up with cofounders, firing employees, fighting evil investors, fighting con man, fighting bad reporters, dealing with malicious users, dealing with competitors (sometimes in person)… All kinds of drama. You’d better practice this kind of things before starting your own company.

10K sounds like a lot of money, do you really set your own bar there? What examples did you encounter of people making 10K on their own while still working at corporate?
I mean $10K it’s like a website w content for US audiences and getting 1K readers a day for a year - depending on the niche you could make even more. It’s not that hard. Not easy. But not hard either. For example posting on relevant Facebook Groups every day a couple of hours a day would suffice.

If you can do that you have a basic grasp of marketing, copy, product market fit, accounting and taxes, financing, maybe design, hiring and outsourcing. Definitely a head start.

This is true not only for software or engineers.

10K is still significant but you definitely need to set your own bar.

Anyone in the 50K to 150K wage market needs to have a deep understanding of whatever it took to bring in 10K without your employer, it's going to take a lot more of that once you no longer have a paycheck from a job there.

Even building success selling used cars on the side can be very worthwhile to engineers who are considering becoming entrepreneurs, when it could be regarded as a career distraction on many other engineering paths.

And however long it took you to bring in the 10K, it's likely to require 5x to 15x as much time to match your employment income, when left to your own devices.

A lot of times when you get far above 150K in wages, any windfall can be based less on productivity and more as temptation so you don't start your own company when you think about it.

At that point you'd really need to independently be able to make a lot more than 10K a lot easier & quicker before it would make sense.

Might have to sell something at a lot bigger scale than a few cars then.

I was about your age when I founded a startup about 8-9 years ago . One thing I did was never went to a full time job and the safety of regular an income . I took freelancing jobs and consulted few odd jobs for about 2 years as I worked to getting a MVP out and get seed funding .

I did have student loans pretty much like anybody else , and it wasn’t easy certainly . Trying to balance working on consulting gigs and building your app at that age there is lot to learn to become better developer and also figure out how a startup works is hard.

My reasoning was financially the older you become more it harder to quit a full time job and do what you want. A house mortgage , family, kids their education etc keep adding up , your lifestyle may make it hard to quit .

The downside to the approach knowledge and experience helps a lot . While I learn a lot fast, with my current understanding I could perhaps do what took 5-6 years in a year or two. However I don’t think I would get remotely same knowledge had I not been working under that kind of pressure .

Would I do it again ? I don’t know. I did a miss lot of typical twenties life , most of my peers / friends are in very different stages of life then I am : financially stable , found their life partners, have kids and settled down on life goals on what they want to do. While my startup is doing pretty well , until there is an exit , financially I am probably not far a fresh graduate, never could spend time in relationships , this despite being perhaps one of lucky ones still in the game and part of something fairly successful, there are many founders who had to face hard truths and try to get back to regular jobs or dig deeper and deeper in still lost in their ideas and having lot tougher time than me.

I was 26; it was the dot-com boom. I had no clear plan but a potential client called me asking for something I could deliver at a price that they were happy with.

I was mostly profitable by about week 5 -- so I only skipped one pay cheque, but I didn't have children then, so it was easier to live cheaply.

But that was a service business: service businesses are easy to get started, but they are hard to scale. If you are thinking of making a product business, you are in for a much longer harder road.

I prefer to experiment with ideas and ideally get an MVP out way before officially deciding that I’m “starting a startup”. I worked on https://divjoy.com for 6 months on the side and only decided to jump into it full-time after validating the MVP (mostly thanks to my Show HN).