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Interesting stuff, thanks for sharing.

Losing $50k and a college friend may seem like a lot but I think it is at the beginning of your career. But good that your learn these lessons before you have a $$$ home, a wife and kids -- then losing it all is a lot more serious.

I would not be surprised the hard nootropics played more of a role than you give it credit for in taking you down such a path. Hyperfocus drugs and anxiety-inducing drugs are not conducive to globally optimal decision making in a diverse and rich environment that is critical for running a successful business.

There is a nootropics curve: do the light stuff and you'll probably come out ahead, do the hard stuff (e.g. adderall, aka meth) and you ... are literally doing meth.
I still don't get why he was taking nootropics when he wasn't doing anything technical. In fact I'm not entirely sure what he was doing, at all. He seemed to want to "start a startup" without knowing what he was building, for whom, to solve what problem, or what kind of value he was aiming to create.

The biggest red flag to me was that they tried start a startup to which (as far as I could tell) neither founder brought any actual useful skills. You can get away with that sometimes if you have huge funding and can work the hype machine, but not as a pair of self-funded kids.

(As an aside, point 8 'Go Lean' is basically saying "push your risks/costs onto others, exploit your workers, better yet partner with someone who has skills so they can do the work for you." I've met guys who (try to) work like that and they're leeches.)

The nootropics angle was disturbing for me. If you take so much (and I guess this can be a slippery slope) that you get anxiety problems then those substances are a problem for you.
> Don’t limit yourself to starting only what you think could be a billion dollar company

Small comment about valuation vs return. A lot of business types have really rotten valuation yet provide a somewhat steady income stream for the owners. The valuations are crummy because the potential passive income stream is too small. However these businesses can be lucrative for an active investor/manager.

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Attempting a start-up is like learning how to walk. You will fall, and it's really hard to teach someone. You have to learn on your own in your own way.

For me two important points 1) always surround yourself with people smarter than you 2) it's all about money. Hit the ground and start making money

All in all this is a very good post. I cringed at the first line when I read he was non techie. That explains most of the failure. Plus his choice of co-founder.

My startup doesn't even have a good logo, or confirmed co-founders or is registered but with focus on earning revenues we are making money

I kinda agree that it's very difficult to start a tech and not being a techie, but you can compensate by having deep domain knowledge. Especially in b2b.

That said, we now have a dev on our team and we can do a lot more. It does pose the danger of feature creep. We try to be very aware of that.

It's unfortunate and I sympathize with the author. But that said most of, if not all, the lessons-learned points he makes could have been potentially avoided if he had just spent some time reading even one or two startup-how-to books. There are hundreds of those now.

There are many many founders who have been through the exact same situation in almost exactly the same fashion. And they have shared their experiences. So why not read up or ask advice from them before jumping head first? It doesn't take long; 2-3 weeks tops.

This is my advice to future entrepreneurs -- read on a variety of topics before you jump in head first. No matter what your idea is or area of expertise gain some understanding of at least some areas of running a business including but not limited to marketing, sales, technology, finance, incorporation, financing, growth, hiring practices, legal, equity, etc. etc..

It's almost as if lessons in building a startup are more often than not, learned the hard way. Even people who have read blog posts and how-to books fail to recognise when the lessons/advice they are reading are applicable to them.
The problem is that most startup books tell you what not to do, not what to do. Actually finding an underserved market that can be serviced by something a founding team can build is a bit of a black art. Anyone who finds one is busy building that startup, because the financial returns of actually serving the niche are so much better than that of telling someone else about the niche.

Before anyone mentions Lean Startup or Startup Owner's Manual - I've read them, lent them to friends, actually put them into practice, and that startup (startups, actually) still failed. And I've got a half dozen or so friends and acquaintances who have done it too, and their startups all failed too. The advantage of that methodology is that you fail fast, oftentimes before you quit your day job, but if founding a startup is something you really want to do, knowing a few dozen ideas that aren't viable businesses is only marginally useful.

> The problem is that most startup books tell you what not to do, not what to do.

This is actually better. Because it means that the authors have had their failures (hopefully?) and are telling a practical story. It's subtractive but it works, re. Ten Commandments, via Negativa style.

It's actually much worse to tell somebody who'll probably be halfway across reading your book to jump x metres when the wind speed is just under y mph to achieve some z business effect.

Point is your context may not be somebody else's context, so it's much better to harp on universal principles which you violated in business than to show us a sequence of events which leave out the role of timing, chance and other unknown unknowns.

It seems you're confusing what's undoubtedly an art, to come up with a good idea, with the mechanics of being a startup, the latter being a more-repeatable motion, that is well-described in the literature that I believe people here are referring to. Of course there's also plenty of testimony on what were bad startup ideas, but obviously it'll be up to the entrepreneurs in question to come up with their own brilliant startup ideas.
Agreed, 100%. My co-founder and I read all of Paul Graham's essays before starting our current company [1], and it really helped us get a good intuition for the kind of work that gets you closer to product-market fit. (Good work: direct sales, building MVPs. "Play" work: branding, getting coffee with people outside your industry, spending time on HN.)

It took us 5 pivots and a year before we saw any meaningful revenue, and it would've probably taken us three times as long w/o those essays. Three pieces of "book knowledge" really helped in making hard decisions on the journey so far:

1) As an entrepreneur, you have the ability to make excuses and, say, welch on a sales call. ("I am not feeling well; I had better sleep in.") You can exercise free will in this manner, but doing so is a complete moral failing. (Steli Efti)

2) Never buy risk unless you're being adequately compensated. Before you have product-market fit, the riskiest thing to do is to work on a project with a long feedback loop. Structure your projects so that you can learn if it's working or not ASAP. (Alfred Sloan)

3) Keep track of your runway, and don't forget to exercise :) (PG)

[1] We read them because they were super fun to read - it didn't feel like homework or due diligence! PG's Twitter is also wonderful.

Overall rule of everything in life: nothing is worth it if it stress you out.
I so would love to believe in that, but I'm old enough to know that it's not true.

I'm still upvoting your comment, just for its optimism. ;)

Yep. My kids stress me out to high heaven. But I'd still say they are worth it.
I counter with: Nothing worth having is easy to get.
I'm going to guess you don't have kids? If you do, I'd love to know your secret to a stress free life.
I think there should be a word for the particular kind of bikeshedding that happens when the first task undertaken is to make a name and logo, which is, at the start of a project, literally the least important thing.

I think it's some kind of signifier that a project is doomed when logo-making happens so early; maybe it's because it means that no one wants (or doesn't know how) to do actual work. I've seen it happen multiple times.

What about mar-a-logo

Actually there doesn't seem to be much that sounds good with logo applied.

playing house, make believe, idea men. whenever i hear this kind of behavior or talk i'm pretty quickly ending the conversation.
> Great guy, but he had no idea about marketing, no dev/design skills, wasn’t investing any money, and was just willing to help. ... Lesson — if you are going to get a co-founder, actually choose one for the right reasons. Avoid friends/family if possible.

But... but... how was he even supposed to contribute and pull his weight without any crucial competency in an area that directly impacts the product's success? The issue, here, is not that he was a friend/family. He was simply not useful.

Yes, if he had to match the author of the post in terms of financial commitment (or even throw in a non-trivial-to-him sum of money), he would have taken the startup more seriously and have been less likely to just walk away. The issue wasn't that he was a friend/family
Regardless of whether that was the primary issue or not, I think the trap most people fall into is to simply work with somebody only because they are comfortable with them. Or perhaps the other person even insisted on it, but the founder didn't have proper experience to realize that was a bad idea. Comfort is an easy trap to fall into.
Honestly aside from the $50k I'm having a hard time seeing what the author was contributing, let alone his tech bro. It seems like this whole operation was a ready-fire-aim situation, probably why it failed.
> I Lost Everything

I doubt that a person who can post about it on the internet did actually lose everything. Most likely he leads quite a luxurious life: he is a wealthy (compared to other parts of the world) American, most likely wrote his story from his MacBook and has a place to live. A lot of people can only dream about a life like his. His expectations is what makes him believe that he "lost everything".

P.S. Clicked on the link after writing this post. Yeah, the guy actually wrote it from his MacBook.

If you read all the way through, you'd see that they have since started and sold another startup. At least, that's their story.
> If you read all the way through

Why would I though? His story already sounds like something not very true and interesting. The guy exaggerates a lot and quite out of touch with reality. There're plenty of other interesting things to read on the internet.

Why would you bother commenting on something you can't even be bothered reading?
I did read enough of it and feel no need to read any further. If I saw an article titled "Why we should abort all boys before they are born", I wouldn't read it, but would infer that it was most likely written by some crazy feminist, who was out of touch with reality. Pointing out that this guy is out of touch with reality here on HN, where most of you are wealthy white Americans, just like that guy, is akin to commenting about that imaginary article on a feminist forum.

You recognize yourself in that guy, that's why you feel the need to defend him, that's where all those downvotes are coming from. But what I see in that guy is not myself. I see yet another whining American, who thinks that losing everything means losing something.

I had a loving girlfriend, friends and a job, and now I have none of that, but I don't claim that I lost everything, because I saw people who actually did that. They have no hope, no money, no future, nothing to wait for, only cold and real, true despair, which only to some extent can be alleviated by drinking vodka.

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That is the part of the story that sounded made up. A few months later he founded another company the right way and sold in it in 9 months.

Judging by the comment that he would never pay by the hour instead using a flat salary he would simply assign expected tasks and deadlines. Not sure that strategy attracts the type of developer who could build the next facebook.

The problem with trying to figure out what your product is by actually developing it is usually solved by designing what you want with pen and paper first.

Most successful businesses start with a product idea and the difficult part is getting funding to built it. It sounds like the author started with money but no vision.

With this line of thinking, no one is entitled to feel bad about anything unless they live in a mud hole and eat bugs for breakfast.
There's a deeper trend here that the author is still unaware of, and that is - being delusional and not having any friends/family who will point out your head is really far up your own ass.

The issue is when you're in your 20s and you had some financial success, you can use that to justify not listening to anyone and even feeling like you are eligible to give anyone else advice!

Reality is, in your 20s, there are things you don't know know that you don't know. That's how little you know :)

This is a subtle point - you don't even know, the types of things you don't know, you are not aware. That's what being delusional is about - it makes you write blog posts that you genuinely feel will help others, and all the while you are VERY much lost.

Anyhoo :)

On point. He says some ok things. But I have no indication he really gets it, so not who I would listen to advise from.
Why would anybody invest in a startup without #4 and #5? I simply don't understand spending a huge amount of money like that without knowing what you are spending it on.
I ended up taking a couple months off before starting another SaaS with a couple friends, and with less than $1k invested between us, 3 months in we were live with sales and it was acquired 6 months after that.

No it wasn't, you fraud. source?

So basically take a year of business courses to not be a moron. Got it.
Please don't post snarky comments here.
This poor guy actually did get fleeced.

Sure, there are people who aren't very technical and don't have any MVP to speak of, but most of those people know to stop before they've blown through $50,000 and have shredded their liver with "brain drugs" (which are just drugs btw, there is literally no pill for hard work)

I'm glad he eventually got a start up going elsewhere, but I'm genuinely worried for this guy. His writing is all over the place and he was ripped off by shovel sellers during a gold rush. He couldn't see any fault with paying thousands of dollars for legal services and developers when he had barely any customers and no discernable product?

Yikes, poor guy.

> ...he was ripped off by shovel sellers during a gold rush.

Good luck trying to convince the prospector that there isn't actually gold in them hills.

Yeah maybe he got fleeced by some opportunists, but he also dove head first into making a "epic company" with no idea what he was actually selling (at least that's how it sounds). It's not the shovel seller's job to vet the skills of the prospectors, and even if it was, do you really think the prospector would listen?

Sadly I can only agree with you my friend!

A businessman probably shouldn't be judged by the success of his customers.

You can sell the horse some directions to the nearest watering hole, but you can't be judged on its drinking ability ;)

> Investors were like LOL, have a nice day (especially if you have poor traction). And yah it’s just something I avoid now.. if you’re going to make something that helps people, charge for it.

This times a million. I've been burned so many times I use as few "free" services as possible, and nothing critical ever goes on one.

> Note: I’m gonna get crap about this probably.. I’m not saying this can’t work, obviously it has worked for a lot of companies and continues to.

It continues to work because the bubble is still holding. Eventually when privacy regulations finally go into effect, that decades worth of millions of users data that every startup trades around in back rooms is going to be effectively worthless. I suspect a lot of companies will be shifting to subscription models once we finally end open season on spying.

>"My startup had to deal with payment processing (at least initially before I pivoted) so I thought I needed it."

You generally don't need a payment processor when starting out. The first ~200k in revenue can be done manually. Payment processing is something that takes time to do and most likely you will need to tweak it a few time as you figure out your business model.

>Paying for dev/design work by hour for a new startup is an insane concept to me now. There are always gonna be bugs, something that doesn’t work, something that needs to be added, etc.

Tech products are very complex. There are thousands of bugs and edge cases that needs to be resolved for a high quality product.

>And ideally, especially if you’re a non-tech founder like me, PARTNER.

One of the worst idea is to have non-technical people try to create a tech business without a strong technical co-founder. Imagine starting a dentistry office without any prior knowledge or a partner who is a dentist. Imagine trying to start a restaurant without a chef, etc. Creating a tech business is not a get rich plan. It takes a lot of skill, knowledge, and luck to get a business off the ground. Unfortunately, the media stories that we read make creating a great product or fundraising millions of dollars super easy. The reality is that running a start-up is probably one of the hardest things that one can do.

> The first ~200k in revenue can be done manually.

What do you mean by 'done manually'? Could you elaborate for the curious? How does one handle CC transactions manually?

No idea what his business model is. That said, my b2b saas company ran our first 5 customers with old skool paper invoices and checks, doing 6/12 month pre-pay. CC processing fee's can really eat into early revenue like this even.
Sure, but does high volume low value transactions necessitate CC processors?

If I want to use CC transactions is there a 'manual' way? Can I collect the numbers and 'process' them myself?

Yes. Just get a Stripe account, and you can use a 3rd party tool / app to charge any credit card any amount of money.
Stripe + 3rd Party Tool != Manual CC Payment Processing
I'm talking about manually billing cards using a 3rd party tool that works with stripe.
Yes, you've swiped at a square powered iPad, I presume? But that's not manual payment processing.
what? stripe charges 3%. if your margins are beaten up so badly by small fees and you don't have have better things to do than bookkeeping, find another niche.
I think you'll also find that some companies don't want to go to your website and pay with Stripe (or anything). They enjoy the good ol' classic "send a check" method.
very, very few companies fit this description. So few companies want to send a check that id you're product requires it, you should be in a different niche.
Well, I would say that I'm definitely not in a small niche. And can definitely confirm that most companies pay via check and Wire/ACH. Especially in the B2B world. B2C is a bit different where the company price point is low. For example, most software tools (IntelliJ, GitHub, etc) CC is more common. But for larger services where it may be many thousands a month, your claim does not seem to be the case from my experience.
Surely it depends on the business? It takes 30 seconds to raise and email an invoice and many big businesses will only work this way. CC processing is only generally necessary for B2C.
no it isn't.

unless your invoices are so large that paying with a wire transfer is better, most companies want to pay with credit card or ach.

> Imagine trying to start a restaurant without a chef

No sorry, bad example. Having an understanding of logistics, supply chains, and having consultant contacts for things like building a menu and interior design. It is the foundation of how franchises work - they've (even) done that leg work for investors. Often times they already have studies for potential locations. Investors just add money and management of people.

Source: family works in restaurant and independent supermarket supply chain/logistics.

> One of the worst idea is to have non-technical people try to create a tech business without a strong technical co-founder.

The best formula I have seen is one business guy and two strong programmers, where one of the two has some talent in ops.

This doesn't surprise me at all. I'm a BA/Dev. and if it's a team of two, I am going to be much more productive working with a sysadmin/ops guy than I am with another dev.
I concur. Our initial team was just that. We had an myself (Engineer), A sales/marketing guy, A new Engineer, someone in Ops part-time. The combination made the division of labor so much easier, which directly results in a faster go-to-market.
And yah it’s just something I avoid now.. if you’re going to make something that helps people, charge for it. Note: I’m gonna get crap about this probably.. I’m not saying this can’t work, obviously it has worked for a lot of companies and continues to.

So there's this meme:

  1)Make something awesome
  2)???
  3)Profit.
Don't know where along the line we forgot that #2 was simply "sell it to people for money" but it's definitely worth a reminder now and again.
I think was the most important lesson: Get clear on WHO you’re making this for and how they can be reached. This was one of my bigger f ups. Fast forward 8 months to when I had something ready to get my first users.. I knew it was for business owners (B2B) but didn’t realize that they are that much harder to reach (for me anyways) than consumers, and I also had the type of platform that I had to grow city by city (f’ing nightmare). After a couple days of going door to door to businesses I could start to see how this was going to be a problem.. I didn’t account for the time/costs it will take to reach my ideal customers. It was a big smack in the mouth. So figure out WHO you are making this for and how you’re going to reach them before you start. Just take that into account so you have the right expectations and you can plan/budget for it.

If you can't reach the customer you are screwed.

> I think was the most important lesson: Get clear on WHO you’re making this for and how they can be reached. This was one of my bigger f ups.

Probably one of the most common f-ups: not having customers that actually want your product.

> your off to the races

my off to the races what?

> Once I had my idea, I spent about 2 weeks deciding on a name/domain I should choose.

We saw it many times before. And also you spend time setting up email on your new domain, and simple website, and analytics for your launch page, and sign up form and blog etc. Instead you should focus on your business, but it feels that without all of this you don't have a legitimate business.

We started bunch of projects and saw this cycle repeat itself. Now we are trying to help fellow entrepreneurs to get through these initial steps as quickly as possible. For a small fee (that is much smaller than usual annual fee at known website providers) we will do lots of configurations, email confirmations, dns table editing to get you free email, website, blog, analytics. We will even setup Stripe account for you (you'll just need to put your bank info to be able to use it). Check out https://www.ninjalauncher.com. Sorry for the plug, but it seems relevant for the discussion.

Thanks for sharing this, I really enjoyed reading it and while I was lucky to avoid most of these pitfalls this time around, I definitely fell for a few of them on earlier ventures. I can sympathize.
One invaluable thing, especially for first time founders, is to have a mentor who's "been there and done that", to help with direction and important decision making in the young startup company.

You can't win them all, yet there's a lot you learn from failing and the lessons will stick with you.

>"Lesson — if you are going to get a co-founder, actually choose one for the right reasons. Avoid friends/family if possible."

Can someone tell me if the above statement is a mistake of the author? I mean the co-founder should be someone you know from long time that would be your friend or family brother/sister right? I think the author has chosen the wrong friend.