I've bootstrapped a telecommunications product[1] to low 6 figures in ARR. It's the most successful venture I've had. I started the very first version in 2018, and released the first version of the app in 2021 (before that it was entirely done using off-the-shelf tools). I'm mid-40s now, and have been either freelancing or trying to launch products since I was mid-20s. I still have a job, but it's a good one that I enjoy doing and it leaves time for my business stuff. I would be better off financially if I had just focused on a traditional engineering career path and invested regularly in broad based, index fund ETFs after finishing university in my mid-20s, but whatever. I own a house in Australia which is an achievement on its own. I have a lovely wife and 2 teenage kids. We're all going on a 2 week holiday to Greece later this year. I have 2 new cars (financed) and a nice office in the city. I have always been the primary income earner for my family of four. Life gets more expensive as my income goes up so I don't wind up with much left over even though I'm earning considerably more now than I ever have. I'm pretty happy with how things turned out and I've always enjoyed the various challenges I have attempted, but on the other hand I look like I'm about 60 and I've lost a lot of sleep!
Ask HN: Entrepreneurs, how long did it take you to succeed?
41–50 of 65 posts
Re: Ask HN: Entrepreneurs, how long did it take you to succeed?
#42I started coding AddonInteractive/AddonChat in 2001 shortly after graduating. A simple Java-based chat SaaS. When I felt it was good enough I put up a web site and started marketing.
Within six months of starting development I had my first customer- who hated my product's bugs, but helped me find and offered ideas for improvements. A year later I was at $30k ARR. That doubled year after year for some time before leveling out. It was enough to live comfortably for ~15 years, but nobody mistook me for wealthy.
No exit opportunities.
I didn't start by dwelling on ideas. Some parity has to come first, then add value. I looked at companies building things of interest to me that I knew to be attainable wrt time and money. I emulated in my own style what they did best, I avoided or improved upon what they did poorly and I shouldered my way into the market. Above all, I listened to my customers and followed their lead.
Re: Ask HN: Entrepreneurs, how long did it take you to succeed?
#43You should almost always stick with an idea for longer than you think. I've had 3 successful projects (one making over 100K MRR[0]) IMO the main differentiator between winning and losing is how fast you are iterating based on customer feedback. I think about it like throwing a dart at the dartboard. You might hit the bullseye in one shot but usually you'll just hit somewhere random then it's up to you to iterate and…
were your projects in spaces you were familiar with? I feel like that makes the dart less random. Also I feel like it's hard to get customers/users on calls
well they were all websites so they had that in common but not much else. I would recommend starting off with an app store of some kind since getting initial customers is a real pain unless you already have some lined up due to past work experience / networking. That said, with enough time and screaming into the void you will get someone to walk through the door. Best to ask them as many questions as you can while they are hanging around!
Re: Ask HN: Entrepreneurs, how long did it take you to succeed?
#44Overnight with a really solid idea with good timing where I understood the space. The same idea with bad timing (rentry after a fantastic exit that I juiced with a condition to not renter the space for 3 years and a subsequent launch just prior to covid), never, because I'm not going to spend my own money on getting it off the ground again post covid. I've got 3 things working now that are 10 years in the making if t…
Can you clarify more on your "overnight success"?
Yeah, I worked for a company in a relationship/middle man space that solved a major discovery problem at the time.
Due to some perverse incentives in the industry as well as some protectionism and legal chilling none of the players actually solved their customers fundemental problem. They got stuck as these weird tweener lifestyle companies.
I quit, moved to a cheap studio apartment in Brasil for 3 months (we still had a bully in the space put together a bs packet and used their connections to get some FBI agents to show up on our doorstep only to drop everything after our little interview), coded out a marketplace play and launched it.
Ycombinator flew us out but declined and a group in a smaller market gave us the only money we ever had to raise. Due to the fact that we built a legitimately fun marketplace play that solved a lot of frustrations in the space Scott Hanselman tweeted us out to his followers and that was all we needed to get the exposure and google juice ball rolling.
Due to the industries continuing perverse incentives, I could start the same company again tomorrow except it would take a big ad words dump of cash and I don't want to pull out of my own pocket yet again (I did just prior to covid but it's an industry that was totally shut down during covid and I no longer have the appetite.)
So by overnight I mean, we started generating huge buzz in the industry and 10x traffic of established players overnight and middlemen don't have motes so we never really had to raise, it was just the time to code out the platform and get it populated with data at the MVP level.
Re: Ask HN: Entrepreneurs, how long did it take you to succeed?
#45What do you mean by succeed? To me, it's very specific. It is to live without debt or a mortgage in a safe place where I can afford medical insurance (which currently costs me $65,000/year). It also meant being able to spend as much time with them as my children required. I guess you could say it took me from ages 21-38. If you count study as a child, 12-38. However by the time I was 23 I was already super happy. I h…
Can you give more details on the business you purchased? Any resources you found useful to learn this process? It’s something I’d like to do after waging away
Re: Ask HN: Entrepreneurs, how long did it take you to succeed?
#46I started cdbaby.com in my bedroom, just me, fulfilling orders myself. It got an immediate great reception from a few people, very thankful, happy to pay for the service, and telling all their friends. So that's how I knew it was worth sticking with. But still, it was very VERY slow going, like even after 9 months I was only getting a few orders a week. After a year it was a few orders a day. That's when I hired my f…
what a cool business. were you in the music world before starting this?
Re: Ask HN: Entrepreneurs, how long did it take you to succeed?
#47I'm not an Entrepreneur, but I will probably become fairly well-off, slowly by following the Bogleheads strategy.
There is a huge assumption here that being an Entrepreneur, the only desire and success definition is to become well-off. Assuming your statement in good faith, it is not the only outcome. So offering Boggleheads strategy as an alternative or get the same outcome as Entrepreneurship is misinformed. I've come across a few friends when I shared I was building something or working for a startup, their immediate question was "Did you not get a job at Google?" :)
There are many people out there who enjoy building. Even if it gets very low traction and doesn't make them life changing fortune, people enjoy it. Along the way, they might make some money. Of course, there are also a lot of people who get on to this journey with the primary goal of making it big. We should not look at the "side-effects" and think that is the cause.
Re: Ask HN: Entrepreneurs, how long did it take you to succeed?
#48What do you mean by succeed? To me, it's very specific. It is to live without debt or a mortgage in a safe place where I can afford medical insurance (which currently costs me $65,000/year). It also meant being able to spend as much time with them as my children required. I guess you could say it took me from ages 21-38. If you count study as a child, 12-38. However by the time I was 23 I was already super happy. I h…
> farm in town
Genuinely curious where this might be, the only place I can think of might be Tillamook, OR!
Re: Ask HN: Entrepreneurs, how long did it take you to succeed?
#49Earlier quoted context omitted.
Unironically, living on a boat and working on my own thing is my dream right now.
There's gotta be a ton of people in their 20s working remotely and living on a boat right now. They don't have to bust their ass like an entrepreneur either. They're just normal employees. What is it with boats anyway?
They are RVs for the water. Pull up anchor and bring your living space with you.
Re: Ask HN: Entrepreneurs, how long did it take you to succeed?
#50Been working on something since 2020. Working on another thing for the past three. Just soft launched the later. Will launch the older project later this year. Been using it daily since 2020 as a way to dog food it. If you take the long way there it’s more fun.