Failed for the past 12 years as an tech entrepreneur | Hacker News Reader

Failed for the past 12 years as an tech entrepreneur

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Back when I was 24, I pretty much hated my 9-5 job because of lack of control over my destiny, the limit of earnings and growth and the idea of going to the office every single day. I realized I could start something of my own.

So I started to look for something easy to do work on that would not consume a lot of my time. Blogs were a rage back then and multi-million dollar exits were quite common. I bought a domain and installed WordPress and started blogging after my working hours. I started a technology blog in the hope to replicate the success of Mashable and Techcrunch. I spent about 4 hours every night covering tech news about companies and social media in general.

2 years passed and I burned out myself. Traffic to the blog was flat and I was not making any meaningful money. I shut it down.

A few months later, I started a website that pulled information from Amazon and displayed dresses in a fancy and intuitive website. I opened a Facebook page, spent a lot of time marketing it and eventually made a grand total of 2 sales in a span of 3 months.

I decided to give up.

The very next year, I decided to build a note-taking web app that was a mash of Google calendar and a to-do list app. The idea was that people would see today's schedule by default and they would easily add and manage tasks.

I hosted it for a few months and lost interest due to a lack of customers.

After taking a break for a year or so, I decided to do something ground-breaking. I built my version of Facebook Groups/Slack that would allow people to share something interesting with others. You could create groups and add/remove people from them. The UI was fancy and a few of my friends and family loved it.

A few months after running it, I shut it down. I found it hard to justify its existence since everybody else was using Facebook groups and with the rise of mobile apps that allowed seamless sharing, my application made no sense.

Sensing an opportunity in media space again, I then started a news aggregator website that aggregated news titles from hundreds of outlets storing thousands of news articles per day. The website was smart enough to cluster the news articles based on topics which, Google news does well. People loved it and it got great reviews, but it was not growing fast enough.

And like earlier, I ran out of patience after 6 months and I shut it down.

After multiple failures, I decided to take a longer break. I had pretty much given up my entrepreneurship journey knowing there was no way I could build a reasonably successful business.

A year passed and I started to feel uneasy with myself and my day job.

So, I built a stupid web app that cleaned new articles by stripping them off of ads and showing only the relevant content. I shared it and got no real feedback from others. Nobody cared.

That's where it hit me, why not pivot to and a link management platform? I thought it's so easy to build and manage it. I could feel the tingling in my body. I built https://blanq.io/ with the excitement of a toddler.

I was so wrong.

I spent the next 1 year building the landing page, the entire web app plus some extra features in a hope that it will take off.

For the first 18 months, I had no paying customers. I put everything into this. All my previous experiences of failures and learning went into building this platform. "How could I fail?" I thought.

I then decided to stick to it and give myself 3 years to decide its fate.

On the 19th month, my efforts started to pay off. I landed my first customers then 2nd and then 3rd.... and so on. It's been 8 months since then and I now have 10 paying customers using my platform almost every day and growing every month.

My learning:

1.Don't quit too soon and don't be too hard on yourself.

2.With each failure, you do get better at not failing.

3.You improve at everything as time passes - marketing, programming, sales, operations.

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I’m sincerely not trying to be mean, but it’s possible you were previously simply bad at entrepreneurship.

There is this dominant narrative that entrepreneurship is primarily about raw willpower and persistence despite the odds. As a 20+ year entrepreneur I do not believe this to be the case.

I believe the primary skill is observation. Yes, we need to try different ideas, but what really makes a product work is listening to the market and identifying opportunities to create value. You’re not fixed on a product/solution ahead of time, but are just paying attention to needs and how those needs intersect with our unique abilities to create value.

When this is working well, it looks like luck. Over time we develop multiple viable business options and we get to choose the very best ones. Instead of a slog, success comes relatively easy.

Right, and that is totally okay. Maybe try going in with someone else for your next project. OP has the technical chops to deliver, doesn't mean they are good at solving problems that people want to pay money for.

Or maybe the products are indeed great, but your marketing is weak.

Either way, get help.

I guess so. Besides tech, I did not have any other skills to market my product. Since then, I have learnt a bit of Sales, cold out reach, marketing channels, distribution and a lot more. In my 20s my primary focus was to look and do something cool than think about selling the product.

I worked on a project with a big time art director from a big time ad firm. His go-to saying, “build it and they won’t come”. He was making the point that publicity is what makes a product. Of course I had to learn it the hard way a few more times after that.

I’d suggest reading “Traction”. Even if you are getting help with the publicity on your next venture, Traction describes a great framework for focusing your efforts and knowing when it’s time to swap out the old techniques for new ones.

Kudos for knowing how to take a feedback man, this is extremely important for entrepreneurs!

I'm in the hustle as well and one thing I noticed is that it's not uncommon for entrepreneurs to incorrectly evaluate the potential of an idea. I wouldn't have bet in a few of your projects in which you're were trying to jump on the bandwagon making something that already existed in the hopes that your implementation would be better than established ones.

I personally believe you've got to innovate to succeed, you've got to have an edge over your competitors, make something different, address a market need, solve a costumer pain. And most important of all, validate an idea before compromising to it, to make sure you don't end up a victim of wishful thinking.

For what it's worth your latest project seems innovative to me, a tool which I had never heard before, targeted at a niche market. Wish all the best and luck.

Yes, I have had a bit of entrepreneurial success. I started off contracting, but looked at the needs of my contracting customers and also their customers. After a while there were too many decent ideas to execute. I could choose the ones that appealed, get a purchase order that paid for development and then sell the developed product to other customers.

How did you go about getting purchase orders for products? My contracting work has always been on a time and materials basis. Have always felt it felt rude / awkward to offer the building of a product on different terms to the rest of the work I was doing, but it is something I'd like to try.

Good question!

I would just quote a fixed price to each prospect. Then they may come back with an hourly rate proposal….

But of course any company that sees your work as a part of their intellectual property will not be interested. So I could never do this if I was working on a product that the customer was going to sell.

Where I was able to charge a fixed price and own the IP was instrumentation software for Biotech companies. They were not interested in IP for obscure instruments. Also I found that small engineering companies who were struggling with their software capability would be very interested in a fixed price + royalty deal. Because they struggled to hire software talent.

So the key is to find customers with “non core” needs. Eg if they need a time tracking program they are unlikely to care who owns the IP. But if you are working on a search algorithm for a search engine company they will only employ you on a time and materials basis.

Have you had multiple significant business successes?

Yes, and to the point where I no longer care about business success. I just continue to practice creating value for others.

Piggybacking: just seems OP more interested in success than identifying problems that stir their passion.

> I believe the primary skill is observation

This. But you also need to be good at evaluating your ideas in the harshest light before executing them.

None of the ideas presented are unique or good enough (also not trying to be mean, just honest), the first thought that comes to mind with each is "Doesn't this already exists in some form, if so what's the USP? and is it strong enough"... That doesn't mean it's impossible to make something of them, but it will probably be incredibly difficult and not be worth your time, something that is a variation or combination of existing products is not usually a strong enough idea, and executing it is a punt. Equally, something that is entirely unique but there is little demand for will also be incredibly difficult to and not worth your time.

It sounds as though you made a lot of MVPs, but there is a stage before this which has a less tangible process: Minimum Viable Idea - trying out an idea even as an MVP has a cost (as you well know), and you cannot afford to try everything randomly.

The fact is that most people are not good at evaluating their own ideas - it's a learned skill - you need to move past the initial emotion of "I came up with this amazing idea", then evaluate it in an unbiased light regardless of who originated it, be completely detached from it and able to drop it as soon as you realise it has no legs (which most ideas don't). I'm kinda good at doing this (shooting down ideas), but, I absolutely suck at generating unique and executable business ideas... if you can do both, you will probably do great things... if not, maybe pair up with someone who has the things you lack.

Do you have suggestions on how to best observe in the age of covid?

Saying you're a bad entrepreneur because OP isn't listening to the market is too harsh. Yes, OP does need to build products that already have a demand.

But, that's more of a lesson than a sign they're doomed as a "bad Entr" and should give up.

Having the energy to build something instead of just talking about it shows potential. Just start building with the market in mind first.

OP, I'd recommend some books from bootstrapped entrs to avoid making common mistakes in the future, since this is a pretty common one. Makebook.io and Zero to Sold are great, good luck on your journey. I believe you can do it!

I'm not an entrepreneur, so by all means you know far more than me. But it does puzzle me that a lot of your ventures seem very...generic. Like you made a tech blog in 2008. Great, but why is your blog special? That's like making a Twitter account now. There are some people who receive massive success from Twitter, but they're very rare.

Then you created a note taking app. I don't know if note taking apps were that huge in 2010, but it seems like they were since Evernote was founded in 2000. Ditto with a social media platform, with a news aggregator, with a link manager. Don't get me wrong, massive kudos to you for launching and working hard on these products. It just seems to me that you've been making stuff that already exists and doesn't have any differentiation. Even if you had a new feature or two, to quote Steve Jobs, that's a feature, not a company.

I was naive back then and had very little understanding of how things work. I jumped into things because I felt they were cool and not really worrying about solving a problem.

And I wish I could share some pics of my failed ones, I did try my best to differentiate.

So how is your current project different?

It feels like you're jumping on trends when they have existed for years already without bringing anything new to the table. That'll never get you anywhere.

> It feels like you're jumping on trends when they have existed for years already without bringing anything new to the table. That'll never get you anywhere.

With all due respect, who the fuck are you? And who the fuck do you think you are telling anyone they won't get anywhere? OP's current project has paying customers. That's more than most people ever get to.

Much respect to the persistence, and please ignore these naysayers. I have no doubt you know your space and customers better than they do.

It's undoubtedly got to be hard for the "entrepreneur" without novel ideas or an ability to notice market shortcomings and imagine patches to them. Like you, I read this post with a bit of incredulity - sure, you might want to "be your own boss" and "launch a successful product" but in order to actually do that... you kinda have to do something novel. I don't want to crap on OP's dreams, but I don't see the link manager thing turning into a billion dollar unicorn.

I feel like this is the same thing that happens with musicians and artists - it's trend hopping and hoping to get a second of the spotlight for what's in vogue. One year it's brostep, then it's NFT, then its your vanlife miniseries on Youtube, then it's your hyperpop EP, then it's your "metaverse" art project, etc. I know a lot of people like this and few of them seem to find lasting success because they either aren't sticking in a certain domain long enough to really excel, or have no real passion other than chasing "success" which results in ventures that are half-baked and obvious clones of things that already exist.

> but I don't see the link manager thing turning into a billion dollar unicorn.

I suspect for every $1000M unicorn, there are 1000x $1M businesses.

1. Many of those 1000 $1M businesses can be very derivative, but with some focus that is just too specific for competition (vertical, market, # of clients, feature focus, whatever). That link manager could easily be a yummy small business.

2. I suspect one can make as much money *adjusted-for-risk* with a $1M businesss as one can trying to make a $1000M business (cap-table and yearly profits are also often ignored, and one might make little especially if one is not the founder of a unicorn).

Sure, then I guess the question is how likely any of that is and if we’re adjusting for risk, what’s the opportunity cost vs just working for someone else? My guess is that in 10+ years of saving or investing zero dollars, each subsequent year of dream chasing is going to have an opportunity cost so high that the big payout ending would be the only thing that could balance the scales

The “unicorn plan” is highly leveraged, high risk, and founders ignore the Kelly Criterion for their costs (especially their time).

I would love to see the average return for the founders of ycombinator startups. Given the power law (Pareto) distribution, it can probably be calculated by knowing the number of founders from 2005 to 2010, and some rough estimates of returns for the major ycombinator success stories.

VC as an fund category has poor returns (“the Cambridge Associates U.S. Venture Capital Index averaged just 5.06% per year between 2000 and 2020”). Also VC returns compared with founders equity: have higher seniority (preferential), lower volatility, diversity, and the chance of getting the necessary outlier success story returns.

The median/average founder in the market is a loser.

Do a funded startup for social status, to learn, to gamble, or for kicks. Don’t become a funded founder because it makes financial sense for an individual.

I'm 16 years in and have followed a similar path. I graduated college in 2004, started my business in 2005 and never took a job.

Consulting has gotten me here and I've had up to 4 direct hires with me, but my dream has always been to run a product business. I must have attempted 3 dozen different ideas by this point.

But on Friday last week, we reached our 100th subscriber. Combined with other free products, we now have over 130k daily active users which sounds more impressive than it is. The MRR is still tiny and we still rely heavily on consulting projects that have been more and more difficult to line up.

It's been difficult, sometimes extraordinarily so, but we have such happy customers with huge amounts of positive feedback. It feels like this could really go somewhere. The fire still burns brightly within me though I don't know how. I'm determined not to let opportunities pass me by again.

I have never shared this anywhere.

how you bootstrapped yourself?

he says in the post. Consulting

This is an underrated path, IMO.

Consulting is an excellent way to hone the non-coding skills necessary for bootstrapping a company: Scoping projects, timeline estimation, choosing tradeoffs, finishing things, selling things, presenting products to others.

It's also helpful to be able to get out and talk to other businesses and people on a regular basis. Bootstrapping can be extremely lonely in a way that is hard to understand if you've only ever worked inside of companies with people to talk to.

VCs actively dissuade founders from doing professional services.

VC’s don’t want you distracted from their one shot at your next 18 months. They’d rather you go for broke and flame out rather than building a 5-year runway that allows you to slowly tune your ideas.

Neither is better than the other, but one might be better for a given situation.

Sure! If you're dumping a bunch of capital into something, you want to see that capital put to work immediately growing something to scale-- not for founders to be worried about stretching the capital by picking up nickels off the street.

That is, being capital efficient is good, but being distracted by other non-core things excessively to try and conserve capital is bad.

But that doesn't mean that bootstrapping with a consultancy isn't a viable path. It's only when you do it when you have capital sitting around that's not put to good use that it's a problem.

Because they don't want you helping near-domain competition with the application of the special sauce they just paid for. They didn't buy your app, they bought your time.

I guess it's because VCs are are after the exponential growth that is possible with a hit B2C product but not realisticly possible with B2B. B2B can generate pretty solid incomes though. My previous employer had 15-20 clients, around 2M EUR yearly revenue, a solid 20% margin, with 30 employees. Fintech.

Lots of B2B products sell into huge growing markets that leave a lot of room for a high CAGR for many years (e.g. exponential growth).

Although they should not dismiss it at all as it can lead to extremely successful companies. I have Dataiku or UIPath (they did it for years) as good examples. They leveraged their existing customers to test their first product, with success.

There is kind of a conflict of interest here, no? Providing professional services can raise capital very quickly. Connects you to potential buyers. Provides guidance. Sounds like the same thing a VC gives you, but you retain all the ownership of your company.

Consulting is a great way to make money, period. A decently talented software developer can amass enough projects to overtake their salary at any desk job. However, I would not recommend using consulting income to supplement entrepreneurship nor to expose yourself to product ideas. The best product ideas come from experiencing some pain point yourself (as the "buyer") and meeting other buyers who, like you, know exactly what is painful and why. This is something that you cannot really experience as an outsider.

I really believe in consulting if you are bootstrapping a business - the income gives you runway.

However, take care to not let the consulting income misdirect your incentives (founder or business). A common trap is to chase good consulting income, and ignore the recurring SaaS income that creates a stellar business.

Consulting income: 1. leads to highly variable income, 2. is often dependent on you or a few star employees, 3. creates tiny businesses that get sold for small amounts, 4. misdirects the product direction, 5. strongly misdirects the sales team if they get a commission on consulting fees.

SaaS income requires discipline to chase, but often creates a business with far more long term value (yearly dividends, and market value, hopefully plus a $$$ growth rate bonus).

I have a similar long history of failures, though my failures did generate income - just nowhere near enough to give up the day job. €20k a year at their highest point, €5k a year at other times.

I notice similarities in what you're describing, particularly when it comes to your target market and products.

B2C not B2B.

And generic, anyone products, rather than targeted niche products.

A lesson that took me a long, long time to learn. Targeting consumers over businesses is doomed to failure unless you strike the Facebook / Instagram lottery.

Consumers don't buy software or pay for SaaS apps, businesses do. Netflix and Spotify are exceptions, not the rule. Building a generic app for consumers is futile.

Far better to build a targeted app for a niche business use case.

Yes, this is so true. B2B and targeted niche product is what I did after successive failures. Yesterday a business bought a premium $50pm plan after a quick discussion with the founder. There is so much money lying around with businesses that they don't mind spending on a tool that solves their problems.

Agree. I would add the Netflix/Spotify are more in the content business rather than software (a huge chunk of Spotify revenues actually goes to paying royalties, and Netflix spends substantial amounts on original productions).

So indeed, consumers do not buy software - they buy other things (that businesses do not buy): Services and solutions to "real-world" problems.

The primary exception to consumer targeting (other than entertainment as you mentioned) is in the ecommerce space where consumers do spend very large amounts of money (Netflix falls under that broadly, though I'm speaking more towards traditional retail goods, shops, clothes, just about anything and everything that can be sold online to consumers).

Aren’t physical products a whole different ball game? I imagine the B2C app market may be an exception as well

Is it not a lot easier to market and sell to consumers instead of businesses? The CaC is lower correct?

Depending on the niche, this can be true. But it's also generally true that low CaC equals low per-unit pricing and margins. Very difficult to run a business at a consumer-friendly price point without getting to really substantial scale.

For example, Netflix has all the benefits of scale, low cost of capital, etc. and their profit margin is 11% on a service that starts at $9/mo. So if your service has similar pricing power to Netflix, you might need order of 10,000 individual customers to cover a single engineer. And that's after the frequently massive investment required up front to build a product to B2C standards.

In B2B, it's often easier to find some niche that a) is underserved or not served at all, b) is relatively valuable to some set of customers, and c) can be served with a lower quality of finish because it's a business app.

In the B2B space, it's much easier to charge $49/mo, $99/mo, or higher because businesses tend not to be price sensitive in that range. Also, businesses often will need SSO or other "Enterprise" feature and so then you have a $10k+ annual contract for the same service. In this band of self-service B2B SaaS, there is typically not much of a "sales" process. Just post the info on the site and let prospects choose. You can do demos when it makes sense. But nothing like a 1-year intensive sales process. The sales process is closer to B2C, but for more money and less churn.

It's much easier to build a business when you only need to make 50 or 100 sales (and support 50 or 100 customers) to get to profitability.

Honestly, having bootstrapped & sold a SaaS myself, I would not consider bootstrapping anything with a starting price point of less than about $49/mo. And I would only go that low if customers were encouraged to land on a plan at $99/mo or higher.

> Building a generic app for consumers is futile.

But can this really be true? Plenty of B2C software companies make good and continuous revenue. Take for instance the German company Ashampoo. Their products are not exceptionally original and they were always in a crowded market. Yet this company is everywhere in the low-cost consumer desktop software space. I know this company even though I've never even used one of their products. There are many companies like that. Remember OO Defrag? Well, I just checked, OO Software is still around, located in Berlin, Germany. Ever written a novel in German? Papyrus Autor is used by enthusiasts and professional writers since the 80s. These are just examples from Germany off the top of my head but there are similar companies in nearly every country.

Perhaps what you say is true for "web apps" with subscription model, it seems very hard to reach private users and convince them to pay a monthly fee. But I doubt it's true for desktop applications and I'm also not sure it's true in general for mobile apps.

Too much "I built", not enough "I asked".

You didn't build things people want, you built things you thought people want.

I hope you find success but really after 12 years I'd suggest you get coaching/mentoring/YC startup school, because while you definitely gained experience from your failures, it looks to me that you haven't learned the right lessons from your mistakes. Even if your current startup is making some revenue.

I'll add on to this, though I don't really want to — my entrepreneurship experience pales in comparison to OP.

However, I think I have a key insight.

What OP thinks is marketing is not marketing. Marketing is all about finding out what problems your customers are facing and making them aware of how your solution can help them solve said problems (ideally, you do this truthfully and your product is actually helpful, and it's even better if your product is the best solution available). Marketing is not simply throwing your product "out there" and hoping that customers will buy it, even if you slap a big label on it that says "this solves problem X."

Talk to customers. If the only two things you ever do is learn about people's problems and build things to solve them, you have a better chance of success versus someone with a billion dollar budget who does not do both of these two things.

Glad you kept at it and finally created something with traction.

Here's what I learned via trial and error.

A long time ago, when investors and accelerators and MBA programs began to dominate the startup scene, founders got distracted.

I saw (and sometimes created) half-baked apps and websites, useless market research, chasing trends, chasing vanity metrics, investor pitching contests, startup theatre, and "build it and they will come" BS.

Build something people want and will pay for.

Not just say they want.

Not just say they'll pay for.

Make something that they see and will immediately take out their cash/cc/paypal/venmo and pay for on the spot.

If you can get that far, things start to fall into place. As others have noted, consulting may be necessary to keep things going.

This may not be applicable to capital-intensive fields, regulated industries, enterprise SaaS, but it works for a lot of B2C and even B2B startups.

> Build something people want and will pay for.

> Not just say they want.

> Not just say they'll pay for.

Thanks. From my point of view these are the most important points.

Also listen to your customers and pick the things that meet your goals of the product but avoid including features that are very likely not scalable/adaptable/useful for other customers.

It does also not hurt if you are convinced about your product and stick to it for an even longer period (years in my case). But sometimes it is necessary to jump off much earlier (months in my case) e.g. when the market is not big enough or competition is too crazy or similar.

I've never understood the drive to own my own business.

My parents were both entrepreneurs and it always felt so tenuous and stressful compared to other jobs.

What percentage of small businesses actually end up making you more money than a traditional job? If my parents had worked at Walmart with their business degrees, they would probably be making way more $$ at a much more stable company than if they had run businesses.

Of course, I say this as a person who has been very fortunate to decide on the right degree and career at the right time ( Software Engineer ), and has always been in enough demand to hold a well paying, steady job.

My significant other has a less fun job. She works as a DBA at a museum. Every day I hear a new horror of being tech in a non-tech place. You don't realize how essential agile is until you see what it is trying to solve. [0]

- 0: In my opinion, agile is about forcing stakeholders & product to commit to plans and communicate with tech in a timely manner, in order to avoid blame shifting.

Just my personal anecdote. I find it much less tenuous and stressful compared to most jobs. The key may be that I'm doing consulting and not trying to market a product.

Day to day I'm not really a part of the team. If the project ultimately fails I don't have to deal with the aftermath, or the project has already failed by the time I'm brought in and I'm just cleaning up a mess. Regardless, it's not really my neck on the line. It's ultimately the company's fault and I will do my level best to help them, but that's the end of it. Switching to consulting REALLY helped my mental health in this way: If the company makes a bad decision, I don't care anymore. I feel like many (most) employees feel a lot of negative emotion when they believe management is making a bad decision. That's totally gone now.

Regarding tenuous, I feel like I have much more job security compared to a regular employee. More people want my time than I have time. So if one of them bails on me, I just go down the list of relationships. In effect, I have multiple "employers." Worst case scenario I just get a regular job somewhere for a few years. If you're a person who doesn't interview well or is otherwise not confident in your ability to go back to a regular job easily I can see why this would be stressful.

For me, it's mostly about independence. Living my life on my terms, on my own time, and on my own agenda is priceless. I don't have to ask anyone for permission to go for a walk or have a 3-hour long lunch if I want to. I can slack as much as I want as long as I keep the lights on.

Oh, and I passionately hate alarms. Don't want to wake up every morning just because someone decided for me that I have to be somewhere.

Sidenote: Good decision-making matters a lot. You can work for thousands of hours without having anything to show for it, or you can work for an hour and make more money than you've ever made in your entire life. Scary but exciting. See Taleb's Mediocristan vs Extremistan: https://people.wou.edu/~shawd/mediocristan--extremistan.html

> I don't have to ask anyone for permission to go for a walk or have a 3-hour long lunch if I want to.

Me neither and I work at a FAANG.

I think a lot of those serial entrepreneurs that have never worked in companies have a very skewed idea of what it actually looks like once you're in a decent company.

Most companies aren't decent, far from it. And I doubt most people have a fair chance of landing one of those decent jobs.

Even putting all that aside, working for someone entails doing what you're told even if you don't want or agree with it. That's not how I want to spend my waking hours.

So you're telling me that if your customer wants the button in blue and you want it in yellow, you won't put it in blue?

Being your own boss is a construction of the mind. If someone else is giving you money, they are your boss.

> So you're telling me that if your customer wants the button in blue and you want it in yellow, you won't put it in blue?

If I don't feel like making the button blue, I won't. If they don't agree with my decision, they are free to take their business elsewhere.

> If someone else is giving you money, they are your boss.

It is true in some respect, but when you're employed, you only have a single or handful of bosses. When you run a business, you have tens, hundreds, or even thousands of customers. You can say NO to any one of them when the push comes to shove.

As the saying goes, "Entrepreneurs are willing to work 80 hours a week to avoid working 40 hours a week." It depends on what motivates you I suppose, some people don't mind working all the time as long as they get a feeling of ownership.

It's also easy to look at the richest people alive, notice that they're all entrepreneurs and then conclude that starting a company is the path to riches. This suffers from massive survivorship bias of course, but humans are how they are.

There are personality types that don't mind the extra risk and also personality types that put high value on being at the top of a hierarchy

Both my parents are entrepreneurs as well. My father a couple times over. My older brother also set out that way, and had a couple businesses, and I actually worked for his IT company for a few years, until he shut it down (and he now works for at tech company in SF).

There was always the idea that being my own boss would be cool, but also a lot of angst about what if I succeed and have to deal with the stress of not knowing how things will be month to month if it's not a breakout success? Most businesses I've seen are not startups that get huge investments. They're small businesses where people struggle much the time, even if they have comfortable stretches.

Eventually I settled on what I would want for any business of my own, which would be a side business or lifestyle business to supplement or maybe supplant my day job. I mostly stopped pursuing that, but am always open to the idea. Through introspection I've realized that were I even to somehow have become the founder of some startup, I probably would have wanted to exit with money ASAP as it grew, because that level of instability is just not what I'm looking for, and not what I think I should be subjecting my family to.

Now, I'm fairly happy with a good job and more free time. I don't necessarily regret all of my attempts at side businesses, but I also feel like I missed more of the youth of some of my children than I should have. That doesn't feel like it was the right trade to make, and that's without even missing a huge amount. That's just not something you can get back, so it doesn't take too many nights a week of being absent for a couple years to add up. But there's freedom in dropping expectations for yourself to be doing more, and trying to make it for yourself. There's a reason people lament the loss of the middle class factory jobs of the last century, there's immense freedom in leaving work at work and having that provide enough money to live somewhat comfortably. There's no shame in that, nor in letting go of dreams of making it big yourself, if you decide that you're happier doing something else.

Some of us just hate having bosses. Being subject to someone's whims is such a repulsive feeling for me that I will go to great lengths to avoid it.

I actually even hate having dominant customers. My ideal model of business is a ton of smaller customers, with none of them having more than 10 per cent share of the total revenue.

Also, finding more ways to grow your business is rewarding - both psychologically and financially. I like "hacking" the question of "how can I introduce product X to more people who might be interested in buying it?"

The big difference between consulting and in-company roles for me is that if I have to deal with a stakeholder being foolish I'm aware they're gitting billed directly for the time I'm spending dealing with it.

This isn't connected to how much -I- make each month either, it's a primarily psychological difference.

Agree absolutely that ending up with a dominant customer can make you effectively in-company in terms of your incentives, though, and isn't the experience I want out of my work.

Spoiler alert: as a small business owner, you're EVERYONE'S b_tch. Your customers, your employees, your critics... Being mindful of what everyone cares and distilling the actual value delivered is both skill and constant practice.

It probably depends on the business. I don't feel like everyone's you-know-what, pretty much the opposite. It gave me lot of freedom to send somebody to hell if they start behaving obnoxiously.

Not that it happens much. Even customers are more respectful if they feel that you aren't too dependent on them.

I think for some people working for someone else is akin to selling off a piece of your soul daily. It's not about the money - it's about having autonomy, excitement and risk in your career. Money is just the scorecard.

As an entrepreneur you get to hand pick who you work with, what you work on and how you get it done - something basically impossible working for someone else. If you think about it, in no other time in history has it been normal to work in distributed, mega corporations.

This path definitely isn't for everyone and there's a lot of real downsides. Personally I grew up telling my Soviet parents that I want to be an entrepreneur - and them telling I need to choose a "real" job. Well after trying the "real job" thing, I vowed to stay as far as I could from corporate life and couldn't be happier. I guess it's just a matter of taste.

> As an entrepreneur you get to hand pick who you work with, what you work on and how you get it done - something basically impossible working for someone else. If you think about it, in no other time in history has it been normal to work in distributed, mega corporations.

You do? I've owned my own consulting firm before. We took the clients we could get, and not all of them were our first choice. But we needed portfolio work and money to keep the lights on.

Good clients are worth their weight in GOLD, and are comparatively rare to the "Oh hmm... I thought I was buying a website from you? I have to do stuff?" clients we would constantly see

Your comment reminds me of all those imigrant entrepreneurs who run a business for a generation that pays for their children's college so they never have to get stuck running their own business.

Well done for persevering, but it sounds like you missed the obvious. If you want to start a business, study business (and marketing).

Since you spent time marketing there are 2 conclusions: nobody cared, or you didn't manage to find people who would have. Learning marketing should have taught you both those things.

The classic marketing line is: find a gap in the market or an undeserved niche, understand their needs better than the competition so you can solve their needs better. Then tell them and they should be delighted, becoming your customer. Then work hard to maintain their custom.

Coders think they just need to spaff out products, but you need to build something people actually want if you want to start a business.

It's not too late. Seriously, take some marketing courses at a university.

I agree, I focused too much on technology side and completely sidelined marketing and sales. It took some time but I have learnt my lesson now. I spend a week marketing/sales and a week on building features. I wish I could have known this much before.

Honestly friend?? You know now and you’ve already shared the benefit of your hard experiences. Writing this openly is a wicked gift and I bet this thread had already helped a bunch of entrepreneurs learn.

It sucks for you that it took you so long to learn, but it gives your words a real authority. I’d wish you luck but it sounds like you’ve already got this.

Good run rates. :)

I don't mean spending time on marketing as in advertising, I mean market research, segmentation, positioning... The things you should do before you write any production code if possible.

I hear Blue Ocean Strategy is a good book to help find a vacant position.

Interesting, I will check that out. Thanks a tonne.

What are some good courses/books for understanding marketing and business?

Especially interested in anything that focuses on tech or SaaS specifically.

"Marketing for Entrepreneurs: Concepts and Applications for New Ventures" by Crane is outstanding.

Alternatively find a university doing remote courses and pick modules you'll benefit from.

Prioritizing and learning about marketing is important.

But I think it is a leap to go from there to taking formal business courses.

Many MBAs (I suspect most) will tell you that what they learned there doesn't remotely make up for the cost in time or money of attending. (Most of those pleased with their experience will focus on the networking and career opportunities that opened up to them).

In my experience, most business knowledge is acquired much faster by combining actual practice with learning and a good feedback loop (and in many cases, practice and a feedback loop alone outperform formal education).

I believe that this is especially true of many aspects of marketing. You learn things when you are ready to learn them. Important marketing lessons that are found in textbooks will go in one ear and out the other without experience that allows you to recognize their importance.

I suppose this is why the case method remains popular in many business schools, although I have no confident opinion about its effectiveness.

Bottom line: Its is important to prioritize marketing. But taking courses on it has far lower returns that teaching yourself: so low that I do not recommend it at all.

Some authors claim many markets are winner takes all, where the dominant firm takes 75% or more of the profits, with the rest split between one or two followers.

So if you want to learn how to start one of those I think strategy is critical, not trying to retrofit one onto an existing product.

It's like any architecture. Better to do the thinking before the building.

But yes, it's far easier to learn anything when you're applying it too. Sure you could learn by trial and error but why not take advantage of the collective learning of an industry?

Marketing is a vital skill for entrepreneurship. An MBA is the polar opposite, it would mostly just be a waste of time.

By all means improve your marketing and sales skills, it will only help. Half the battle is building something people want, the other half is communicating it to them in a way that they understand why they want it quickly and concisely.

I know extremely successful people and all of them made huge mistakes in their lives. But I don't believe you are using a good strategy here and find your advice is bad:

1. You should quit as soon as possible is you are getting nowhere. We don't need more miserable entrepreneurs. Entrepreneurship is probably not for you if you fail consistently. Don't waste your live doing something you are miserable at.

2. Each failure can really hurt you, no different from making a mistake while skiing or driving. It can destroy your life: Your relationships, your wealth and health.

3. You don't automatically improve as time passes. Specially if you learn on your own without good teachers. You will acquire "bad practices" or "vices" like if you try to learn to play tennis on your own: It will take you longer to "unlearn" your vices than if you learned from good teachers.

The first thing I would recommend is that you make friends that are entrepreneurs so you learn from each other and support each other.

I sense a very individualistic behavior from your writing but I see customers as friends and that helped me a lot. I give them way more value that what I extract to support my business, and that is the secret. People are not stupid, in the same way children "sense" who really loves them fast, customers could sense very fast the value you give them.

You also develop over time a good intuition on the value you are creating if you know how to listen to your custommers. You don't need 12 years for that, 1 or 2 years is enough.

I understand that "what does not kill you makes you stronger" but I have experienced what failure feels, and it really can kill you, emotionally, mentally, socially and finally physically.

The way to success is making mistakes frequent and small, so small that it can't hurt you: Instead of risking a million dollars you risk a thousand and escalate.

Instead of making mistakes you meet the people that have done what you want and you learn from THEIR mistakes, so you don't need to repeat them.

They will help you and love to do so. Dozens of entrepreneurs have helped me when I just asked them and some of them are good friends now.

> I see customers as friends and that helped me a lot. I give them way more value that what I extract to support my business, and that is the secret. People are not stupid, in the same way children "sense" who really loves them fast, customers could sense very fast the value you give them. You also develop over time a good intuition on the value you are creating...

I see it this way as well. I serve a small niche, and some specific problems therein. I really want the people with these issues to have my solution. It sounds lame but that is more of a motivation to me than the money. Broken thing turns into fixed thing that resumes generating value for the customer. That endpoint is my goal.

I won't devalue my efforts by underpricing, people should pay a fair price. But the money is not the primary driver. If either profit or passion were not there I would probably just do something else.

My equation seems to be that if I get at least a few customers, enough to cover my out-of-pocket costs, then I'll take a risk on my time getting eventually paid for.

I am very proud of you, of what've you've accomplished, and happy to see that your latest venture is getting some growth. There's nothing more powerful in this world than someone who is determined to do something. Slow and steady wins the race!

Also glad to see many others sharing similar stories about not giving up. Since we are on a christmas mood already, big hug to all of you.

Regarding me, I've been making and breaking stuff for about 15 years with moderate success. On 2017, I went to KAUST (flagship uni at Saudi Arabia) as it was offered to me as a place that was looking for talented people, to help them develop and thrive. I drank the kool-aid and gave it a try. It wasn't that great but not bad either, I was enjoying what I was doing so I decided to stay. Time goes by and on 2020, my daughter gets kidnapped by some of the staff there, after I refused to let my wife work for some guys who were doing some pretty questionable stuff. With (not so much) help from my embassy I was able to leave the country and put myself and my family safe again. Almost 4 years of work down the drain plus the psychological damage inflicted to us. That event truly, 100%, burned me out.

But, ..., came back right before the pandemic started, and that turned out to be a blessing for me. The world stopped so I didn't have much to do anyway. I spent time on me, doing things I enjoy, connecting with old friends, taking care of my parents, resting, etc. Earlier this year, the urge to make stuff came back and I launched a climate-related startup that is doing quite well. I have people who work with me (that's a first!) and they keep me moving, focused and motivated. We are about to start working with a HUGE client next January and that is making us feel quite excited. Highly recommend this to everybody, it's common for hackers to tend to "solve everything by themselves", but try to get more people involved, whether they're associates, coworkers, mentors, you-name-it, there's people out there that can make your journey much more enjoyable.

And, as other's have said, don't give up on your dreams, no matter what. If you have to start over, then start over, it won't matter, you will make it in the end!

Thank you so much for your kinds words. Your comment made my day.

Regarding your story, I mean wow, that must have been a scary and stressful situation. I am glad you are in a better place now.

I think the problem was that you mainly entered typically saturated (product) markets. All those ideas have been on the 101 "first product" lists to programmers, for as long as you've been trying.

And the fact that you worked alone(?) just makes things even more difficult. You have entrepreneurs in SF with networks and capital to launch products in mere months - hell, their marketing budget the first months would be more than your revenue the first x years. Point is, it's incredibly hard to compete against players like that, and if you have some easy / low-hanging fruit idea, there's a good chance you'll be playing against those. Remember to do your market and product research!

OP here: Due to HN limit on the length of post, I had to cut down the details to about 4000 characters. I skipped tech used, a lot more details about the applications and the timeline.

Now I am 36 year old and as stated in the post, I am giving yet another shot with https://blanq.io with a hope of succeeding this time.

I did this for a couple of years as well.

I think the experience was invaluable, and I don't regret it, but I arrived at the conclusion that doing a startup is largely overrated.

Why stress out for 60 hours a week for years on end watching your savings dwindle when you could have been making great money at a medium or a big company with great benefits that doesn't force you to work on the weekends and allows you to take paid time off? If you land at FAANG or similar, you'll make more money than most startup people ever do anyway.

The startup community loves to talk trash about regular corporations, but for me the work/life/stress balance has been a great trade off.

This is a classic B2C vs. B2B. Simply put B2C is tough without network effect or funding to build it.

B2C - Customer/User has time, not money.

B2B - Customer has money, not time.

B2B has its own set of challenges too. Making a sale can be a lot more complicated and take easily a year.

Not all B2B is like that. In general smaller companies have much shorter sales cycles than large. Also tactical products (oh shit I have to solve this by Thursday) have shorter lead times than strategic products (how are we going to handle this issue for the next ten years).

The revenue per customer is lower but the volumes higher. It is doable.

My biggest problem with B2C is you have to turn around and monetize your users (eye balls) via Ads or otherwise - now you're back to SALES, but only if you can survive to get the users! It's a catch-22 if you're bootstrapping, VC funding helps.

Enterprise sales has a long cycle indeed, but I'll say it depends on the pain you're solving and the target market.

I dont wanna sound negative but for some people giving up makes sense. Entrepreneurship could be extremely isolating and depressig, especially when its not working out, and not everyone wants a decade of failure after failure and missing out on other financial and social opportunities.

Yes, 3 years is pretty much a good way to measure if you have made it or not. Anything beyond that is pretty much a waste of time. Also, surrounding yourself with people of similar interests will keep you going. Currently, I have some great indie hacker friends on Twitter who keep me motivated.

Be sure to pay homage regularly to the gods of chance. Randomness plays a huge role in success and failure in all fields, but especially in entrepreneurial ventures. If you live in a developed country, relax and enjoy the fact that failure rarely means actual death.

A couple thoughts after reading this. They aren't meant to be criticisms, just a reflection on my own experiences as well because I have had plenty of failures myself.

For one, failing is probable. Most small businesses fail. The chances that you get it right on your very first try is low. Sometimes it takes many failed business ventures before you learn all the lessons. A lot of the lessons can be learned from reading books though. The common and cliche things like "identify your target audience" and "researching competitors" and "see if there is an interest in the product" are mentioned in every book but still skipped by so many.

There is a lot of talk about the things being built and the technology, but almost no discussion about the marketing side which is arguably more important. I wonder how much effort was put into that aspect.

It sounds like there was not a lot of product/market research before building the thing. I'm guilty of this too, building a product nobody wanted because I didn't do homework first to see if anyone cared.

Some of the ideas sound like they had no passion behind them. For example, the affiliate site for selling dresses. Was that something that was inspiring, or simply an easy-way-to-make-money thing? I think that can have a huge effect in quitting or sticking with it.

And it also sounds like there was a lot of quitting too early because things weren't growing fast enough. The marketing aspect may have played a factor here, but from my experience...solo startups DO NOT grow fast. Having that expectation in the first place might have been the reason for such disappointment. Running a business is a long-term thing that could even span beyond your lifetime.

Very few entrepreneurs understand that sure, market matters, and sure product fit matters, however the variable of time is an interesting one. Most startups growth looks super slow, then ramps up, and then quickly ramps up. This is very similar graph to investing $$ with e.g. a X% annual return. The key similarity is the concept of compounding. Individual features, marketing campaigns, blog articles, monetization channels probably won't have an immediate impact, but over time can compound. Similarly, entrepreneurs often think that developing a feature will immediately cause users to sign up. In reality, all you've done is "invest" your money, but you need time to work it's compounding magix.

I don't think this is a tale to emulate.

Everything that failed has been built hundreds of times before. None of the "businesses" started with talking to customers.

Stop building inferior versions of things which already exist. Build the things that don’t exist.

Haha, I did not expect that plot-twist, well done.

Nassim Taleb says we should thank founders, successful or failed, for the risk they took, and I agree with him. So here it is, from the bottom of my heart: Thank you!

I'll thank OP for sharing, it always takes courage to admit failures.

There was a thought provoking article (can't find the link) that made the rounds here recently about the "guy who'll never actually build his startup", describing someone who's always going through ideas and says he'll find the perfect idea one day. The article concluded with encouraging people to just build it.

While that type of person exists and there is a harm to overanalyzing, this serves as the converse. Someone who just jumps into ideas without validating them.

At the end of the day, a lot, actually most, ideas are bad, we shouldn't just pretend enough HardWork will overcome that. We should encourage people to brutally validate their ideas early, it'll save you a lot of time.

Just because you've written a blog post or some code doesn't make you an "entrepreneur". Pretty sure AirBnB founders haven't written a line of code for example.

Creating a business is largely about sales: selling your idea to investors, customers, and employees.

So your new business just does link analytics? Who are your potential customers? I.e. how large is your addressable market?

When I see something like this I think of mass emailers. They tend to require link analytics but otherwise I can’t think of another use case. Maybe Twitter or other social media publishing.

Since publishing is an application where link analytics tends to be used I would focus there. I can imagine it would be much easier get customers for that more user-oriented product than for something that is lower in the stack and more abstract and will likely end up being used for that use case anyway.

Just my 2 cents, trying to help.

Currently I have a mix of clients - some startups, job boards, digital consultants, content agencies that want to manage and track clicks. Basically understand their campaign so that they can improve and perform better.

The good thing is that you can basically track anything. One of my clients uses short links on buttons and images to track conversions.

And yes, publishing industry can definitely benefit from this.

No one ever cares about the amounts of times you've failed. You only have to succeed once. Congrats on your journey

Good on you for continuing to try! I am just now seeing ~very meaningful success for my startup I founded about 10 years ago. An important component of my endurance was that I truly care about the mission of the business beyond financial gain...I think this has to be true for runaway success.

Shameless plug: we are using software to combat climate change (https://bractlet.com) and we're hiring (just like everyone else)! Feel free to email me directly (brian at bractlet dot com) if you are interested.

How have you been iterating on your ideas? Generally, this is what I tell other entrepreneurs. It's startling how few actually take a framework like this to heart (doesn't have to be exactly this):

1. Build a hypothesis about how the world works

2. Build things to test the hypothesis

3. Figure out the world doesn't work that way

4. Alter hypothesis

5. Show progress as you repeat 1-4

I also want to call out that spending 18 months to build a landing page and your web app is an extremely long iteration cycle. I don't have all the context about your life, but that seems to be an area where you can get much tighter based off this post at least.

Yup, switched industries from software to advanced composites (like carbon fiber, kevlar, etc.) design & fabrication in 2003. Been up and down ever since, running both as a job shop and always working to design & build products.

Persistence and flexibility, always looking at new opportunities and technologies with an eye to goals (other than what is fun).

Every lap around the field gets a bit better, and now there's some real breakouts in sight.

Have confidence in yourself, work hard, and think well. Seem to have heard something about: Seek and ye shall find...

additional note:

>>Seem to have heard something about: Seek and ye shall find...

also keep in mind that no one ever said finding it would be quick...

(give yourself some runway, and cut yourself some slack when things aren't as expected)

I've been failing for about the same length of time. Had some weird ups, some weird downs, learned a lot, etc. I should probably write a book, but I really can't be arsed to do it right now. The important thing, to my way of thinking, is that I'm still here, still failing. As far as I'm concerned, I haven't really "failed" per-se until I quit (or die). As long as I'm still moving forward, still learning, and still chasing my dreams, I'm "in the game".

I'll go back to one of my all-time favorite pg essays:

If you can just avoid dying, you get rich. That sounds like a joke, but it's actually a pretty good description of what happens in a typical startup. It certainly describes what happened in Viaweb. We avoided dying till we got rich.[1]

And truth be told, I don't know how much I even care about the "getting rich" part anymore. I mean, sure, all things being equal, I'd rather be rich than not. But at this point, I'm just happy to be still growing, still learning, still exploring. Just being in the game is its own reward in many ways.

[1]: http://www.paulgraham.com/die.html

First off thanks so much for your transparency. Great article and humility that will certainly help the many others in your same situation (like me).

I share your frustrations, but I see things from a different perspective when doing side projects for a few reasons:

1. I treat innovative ideas as potentially growing to something amazing and see them more as passion projects that help me to grow in many ways, including learning new technologies, learning other trades (e.g. marketing, sales).

2. I use my skills learned in side projects as bolsters to my resume. I can testify that I've been approached by employers and been seen as a better candidate than others based on the side project experience I've done. Further, I've gotten other side-gigs that are paying as a result of the side-gig skills I've acquired. Adding these hard and soft skills to your resume makes you a better candidate overall and opens opportunities otherwise unavailable without.

3. I still work a main gig that I (mostly) enjoy, which enables me financially to be able to spend my off-hours working on and funding my passion projects. This to me feels safer than going all in, although it could be argued things inevitably develop more slowly this way.

4. My reward for hard work is similar to open source development in that I'm creating something for humanity that wasn't available before, which may or may not make money, but benefits me for the reasons stated above.

Perspective helps here, and if it grows into something bigger then all the better. If it doesn't, then there are other benefits to doing it that help shape you and your skillset.

I would like to chip in because I know exactly the feeling of the author. The failure is normal and what makes the difference is the ability to continue trying after one failed and having a believe in yourself, but let’s cut the support bullshit and point out the obvious. The author is a one man army at least from the story that I read. Meaning, the projects that you have done were done individually without much help or partnerships, and such projects for the most part will find failure. Why do people sell shit load of material about building in public, building an audience, connecting and being social? Because this matters for success. Those that teach this approach understood that success of tech startup is in people (and not only tech), inside the venture and outside (customers) and that is also why we are writing such articles, for recognition and visibility. Imagine the number of products that are out there without proper audience? Why do we spent hours and hours writing bullshit engagement posts in Twitter when in reality you could build a product instead? Because without that engagement and community, an internet project will have a hard time for recognition and success. Tech oriented founders usually have a block when it comes to social aspect of the business, we are introverts, the thought of writing pitty tweets and liking other’s comments makes as sick, and that is fine as if you have chosen a path of solo enterpreneur, you need to learn to upgrade other skills. I have failed in more that 20 startups in my life and only when I took a step and overcame my dislike of communication I’ve became successful. The key to big changes is your network, the world is this way and now that you made it to the first page of hacker news, you finally understood how to move your products. Good luck.

Manage your reputation very very carefully.

I do tech for an email security service and we start blocking these very quickly once we see any anything we don't like.

Can you elaborate more on this? I think we are getting blocked :|

A link shortener is a simple way for malicious or spammy email senders to cloak their malicious or spammy link in something which is not yet on a block list.

So what we find is that as new ones come into the market they are eagerly adopted and we start to see evil links. From our point of view the earlier we put in place a wholesale block the better, because otherwise they may become "too big to block" like bit.ly etc... Although even these are blocked by gmail from time to time (for example).

If security software can read email enough to observe the shortened URL, couldn’t it just see what it expands to and then judge the target URL? Link shorteners don’t seem to have any obvious CAPTCHAs.

We have about 500ms to make our assessment so we wouldn't follow a link in realtime and depend on it resolving and redirecting etc.

Instead we expand them later and visit and scan them after the fact. But at that point the email is often already delivered.

But bottom line url shorteners are so abused as to be a de facto sign of spam.

I understand your concerns I personally hate short generic links. They are a big security risk especially phishing ones.

The way I counter this is by not allowing people people to create generic links in the first place unless you are a paid customer. Plus, you need to add your custom domain to do something meaningful on the platform.

That pretty much weeds out 100% of scammers.

Isn't this a Show HN hidden in a story? Either way, congrats on finally sticking to something. I hope to achieve something similar in my life :)

I followed a very similar path for a long time. I am 37 now and have been in tech for over 20 years (I started very young). Over the years, I have worked many places, started my own consultancy, freelanced, and have tried starting many other businesses and online services over the years (invoicing, disposable email, some B2B services, project management, etc.).

Most of my business ideas have failed. Some have had limited success (a few hundred per month at most), and only ONE (my latest one) has been pretty noticeably successful right off the bat.

Just keep trying and pushing forward. It has taken almost 2 years since launch, but my Google Sheets add-on that imports bank transactions called BudgetSheet ( https://www.budgetsheet.net ) is only just now very close to $1k MRR and still growing. It's funny to me because my most successful ideas have never been ones that were new or novel. Just practical, useful, and really well understood things that save people time or make their lives easier.

Nice. I'm glad something worked out. Honestly I did not expect the happy ending here. It sounded like the biggest issue each time was giving up way too early. It's easy to say that though and much harder to continue to grind at your own project/start up when it's been 6 months to a year without any real traction.

I wish you all success. I'm intrigued by people who are determined to take primary control of their money-making, because I'm so different from that. I am so grateful that companies exist that can manage annoyances like medical insurance, taxes, payroll, etc. so that I can just show up, do stuff I'm good at and enjoy, and then go home in the evening and forget about it all until the next day. I have little skill or interest in finding exploitable markets, but in general I get along with people well and have no problem with other people deciding what large-scale projects to work on, as long as I have a bit of autonomy on actually implementing them. Thank God not everyone is like me, or nothing would get done! But I think without people like me, very little would get done as well. Good luck on finding your ideal niche.

You are right, both types are essential! Neither can thrive without many of the other :) Cooperation is the human superpower.

Are you doing this solo? I’ve found it’s good to have partner(s).

Ideally with diverse backgrounds; e.g.

  - marketing

  - engineering

  - sales

  - finance

This way the burden doesn’t fall on you for everything and you can lean on others to do their part.

IMO a lot of tech entrepreneurs take the marketing/sales side for granted.

I’ve shared it here before, but here’s my own similar story. I haven’t figured it out yet.

How to Lose Money with 25 Years of Failed Businesses

https://joeldare.com/how-to-lose-money-with-25-years-of-fail...

I had a corporate job for 9 years, did some freelancing on the side until I got a big client. Now I have a team of close to 20 people, a few good clients (referrals work wonders) and a MRR of 110k after 6 months. I have jumped into entreneurship making also a salary increase from a good corp job. I am saying this because for me consistency and incremental reputation and skills building has been extremely rewarding. There is a culture of leaving jobs fast over here and sometimes that is the right thing to do, but sometimes it is more rewarding to build a carrier over a few years before making the jump. Just consider your options and take the time, not everything needs to go super fast.

Nice perseverance!

I'm not really a business expert, but when I hear about your failed projects it sounds like the marketing and distribution channels weren't really fully fleshed out. It's quite hard to get people to pay for things when you don't know exactly who they are, what they value, or where they hang out. This is a really common problem for developers creating product businesses apparently — you build something and nothing happens because nobody knows about it. I'm glad you feel like you have more momentum now though!

When you reflect on what you were doing in the last 12 years what do you think was going on that you could have improved?

The biggest problem with my approach was not understanding my product well. What was it trying to solve? I had no answer. Besides that, identifying distribution channels and lack of marketing were primary reasons of failure. I wish I could have spent more time learning Sales and marketing giving me a better shot at success.

Also, add value. A lot of those earlier attempts were derivative ("let's replicate a tech news site") or get-rich-quick-schemes ("let's mash together two services via a script and see if anybody buys it").

I agree with your observation that none were original ideas but I would blame more on poor execution and lack of patience.

I'm trying to be constructive with my thoughts, so my initial thoughts are: I've had a pretty different experience than you, and don't think your recommendations are good for a lot of people. IMHO you're taking too much risk doing what you think is a market need, when you should be offloading risk and making what the market is actively wanting/needing. This sentiment is repeated by quite a few commenters in different words.

Serial SMBer here, looking back at the dozen entities that worked in the past 20 years -- every one of my projects with 7+ figure outcomes had clear successes to validate the idea 3 months in, and I would often times MVP it off a contract with one client/vendor. (A few examples: niche used office furniture circa 2006, iOS app circa 2010, ML-based investing circa 2011, Amazon store in 2013 - so... all over the place.)

Just adding a bit of anec-data since we have quite a few people sharing what worked (and what didn't), the top 3 learnings for me have been:

1) Know people with deep pockets who want a problem solved - this means networking and establishing a niche for yourself as the go-to execution guy for problem X. I went to school near Sand Hill so that made it convenient. This simplifies your customer #1 problem as well as your revenue problem.

2) Know people who are good at solving problems, esp ones you dislike or can't solve. This is how you scale from a 1-person weekend project to a 1M+/yr rev project. You want this because a) problems that need multiple people to solve are a natural barrier to entry for anybody else, which means your solution is more defensible and b) partnerships are fun and when built right promote accountability where the sum of work is greater than its parts.

3) Entrepreneurship is hard work and should only be done as a last resort, if you know what you're getting yourself into, because you ABSOLUTELY WANT IT for whatever reason, whether because seeing something inefficient drives you nuts, that sorta thing. It's absolutely not for glory-chasers which I find kinda frustating, as a lot of (US) society glorifies it as such and sets peoples' expectations totally wrong and I see tons of miserable entrepreneurs burning out all the time in the startup orbit.

You don't have to monetize anything or have customers to be successful. If all the things you built brought you joy as you built them, then you've done amazing.

We don't need web traffic or money streams to be happy. You've done more than anyone else really could on average. Most people are slogging away for a company, afraid to step out of line or build anything. When they are gone, the company will leave their name on nothing.

You've built amazing tools that will always have your name on them. That legacy is one to be proud of.

I’ve found limited success and failure. Here is what I’ve learned.

Business is hard and important. Marketing, sales and strategy are necessary, there’s no “build it and they will come.”

Working at small early successful startup has been huge for learning.

Learning from local startups and building relationships with other entrepreneurs is huge.

Startup accelerators and hackathons help tech people learn business savvy and connect with non-tech cofounders.

For the vast majority, software dev is an arcane art and dev chops can be highly appreciated by a businessey entrepreneur.

I wonder if you considered leaving the previous project(s) running while adding new ones? Of course if you realized there was a reason they would never succeed, then terminate, but if you were unsure why they were not succeeding, maybe let them continue. An unused app is not a lot of work to keep running, right?

You might collect a few users and one of those might give you a great idea. Customers can make great design partners, and the feedback on one app can lead to an improvement on another.

Congrats on the persistence! The lesson: things take time.

Took me about a decade. I also tried a note-taking app (every new developer's rite of passage it seems), an event guide, digital magazine, and an assortment of other projects whose domain names no longer resolve.

Suck as it may, each failure is a lesson in what not to do. If you find yourself back at square one and still have the drive to keep trying then it's only a matter of time before you create enough value to open wallets.

That's amazing. I am an engineer myself and my problems are that I am not that creative to find problems to solve like you do. Much less the persistence that you have that keep trying and trying again. Kudos to you! I hope one day I will be able to do so.

How do you guys support yourself for 12, 16 or however many years it takes to get to net profit?

If you stick with it, I would recommend you spend a lot more time talking to customers, thinking about distribution channels, and getting creative with narrowing your target audience. And build after, not before, you do those things

I agree with you and has been my biggest learning so far.

Just a nitpick (I notice everything, especially when it comes to spelling and grammar), but on your landing page you mention Let's Encrypt but you didn't capitalize it properly.

Thanks, I noted it down and will fix it today.

Wow that's some perseverance I am soon in the fourth year of working on my project and finally starting to see some revenue but I am constantly asking myself if it's worth it.

Thanks, perseverance and patience were the only things going well for me. My key takeaway would definitely to give products at least 2-3 years before shutting them down. Most apps take a long time to get noticed and SEO works only after a year of effort.

By the way, if I were you and if its making some money, I would give myself 1 more year to see where it goes.

Wow you've pushed really hard on your own.

Have you tried to collaborate with people with tangential skills, e.g. someone with excellent sales/marketing background or in a niche like real estate or law or whatever that has a ton of insights?

Even for Blanq, maybe you could find someone that has a strong need for link shortening for their business, whatever it is?

Well observed!

I would recommend startup school by y combinator

My greatest success so far was a product that earned enough to cover its own hosting fees but not much beyond that :)

In that same time period I made over 1 million in take home pay from my developer job which i turned around into residential and commercial rentals which now bring in waaaaay more than my salary. I have the advantage of being on the west coast with rising property values, but still, sometimes there are better ways than just chasing the latest startup fad.

Thank you for sharing. Out of curiosity, how have you supported yourself all this time?

I still have my day job but work on my product in evenings and weekends.

Yes, all of those ideas are bad.

I'm failing as a regular dev, and I'm too burnt out to care.

Do you work on this full time now, or are you still at your day job?

Thank you! Needed this 12 months into a new MVP build.

I dig your tenacity and courage to continue. good luck!

10 years of failure here, finally reached $1.3 mil ARR

12 years of learning. Not of failing!

Thanks, I would very much like to believe that.

thanks for sharing your story, it is inspiring. What is your tech stack? python?

Vue js + Java 13 + Mysql - traditional stuff but works like a charm.

Honestly this seems like hell.

I'd rather work remotely for a US company and move my ass somwhere like Brazil or Nigeria or Philippines or Thailand.

You'd maybe feel the boredom and the lack of power in the decision making and the shame of having to report and reply "yessir" .

But once you clock out you can then be the boss of the hood and recoup all frustration accumulated during worktime, throw the weight of the mighty USD around, which is even more exacerbated by the tech salary as well as the possibility to invest every excess in the S&P500 so that you can keep on keeping on.

The west has essentially very few people (and diminishing by the day) and each and everyone of them have a telegraph pole up their you know what. It should only be used as the money making app

> The west has essentially very few people (and diminishing by the day) and each and everyone of them have a telegraph pole up their you know what. It should only be used as the money making app

What did he mean by this?

The so-called West is slowly starting to de-populate. I believe the parent is suggesting the hyper connectedness + affluence of the West should be taken advantage of to make money, while / for however long it exists in the present lucrative condition.

Just like you have the dating app or the mail app on your phone.

The west is the money making and business app. Strictly business, don't even call or seek people for reasons which aren't business or money making.

Social relationships and genral life outside work app is Africa and South East Asia. Unlike the west they have loads and loads of people who are not spoiled by abundance vis-a-vis the west which has very few people and all with a telegraph pole up their as*hole.

Breathtaking nature accessible for days on end for the price of a burger in Manhattan

latin america too is great from a cultural perspective. Dating prospects being much better as well.

they don't have an abundance of people like the other 2 tho

I'm here in latin america right now. they definitely do. Especially if you are in a city like medellin or bogota

Wouldn’t it be extremely difficult to throw away all your friendships and relationships and move like that? Iirc studies show spending quality time with friends is a key component to happiness

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