I am (not) a failure: Lessons learned from six failed startup attempts

This line in the article resonated with me:

> First, it sets the stage for what was to come, and second, while it was unquestionably a success, it was not my success.

I used to think that success was being successful the way I wanted and I was often frustrated because things were working but not because of the way I wanted them to. Turns out, it's doubly difficult to make things not only work but also work the way I want.

I've since tried to be more open-minded and see wins that perhaps I didn't expect or want still as wins and it's made me feel a lot more successful. One might scoff and say I should hold myself to a higher standard, but at the end of the day, success is only an intrinsic feeling anyways. It's not a measurable metric so I might as well feel better about the progress I'm making.

In the context of the article, the author could see these all as failures, but it sounds like some of these were pretty successful. In fact, the author concludes as much, finding happiness in the "failures". It's all an arbitrary label anyways.

There is currently a risk asymmetry in startup world that drives away people who could do good work.

Investors know the long odds of success, so they invest in twenty to thirty companies and wait for one to get big.

Founders and employees can't diversify like that, because you only have so many working years. To mitigate this we have decided to award successful founders with huge paydays as a lure to others to throw their hats in the ring. This has some malign effects, namely unsuccessful founders and employees get bupkis. It also attracts the wrong sort of personality to be a founder, selecting for too much risk appetite. (At least what I consider the wrong sort for building a sustainably profitable business.)

I have an idea for how to solve this and I wonder if it's already been tried or if there are holes in it. The idea is to spread the risk of starting a company across something like an accelerator class. If one company in that class gets big, it would be contractually obligated to hire and grant shares from some pool to other members of that class. This would be at the cost of the winning founders' stakes.

The upside for winners would be much lower, but the downside would be lower too. This would attract a different sort of person to this accelerator, and be a differentiator for selecting talent.

My main lesson from running a startup: don't. And if you do, quit when the going gets tough. Perseverance does not pay off.

Obviously it doesn't always end badly. But we get a massively skewed view from survivor bias.

My life turned out pretty damn well once I got a plain ordinary job working for someone else. But I don't kid myself: when it comes to starting a startup, I did fail. The main lesson I learned was that I was always going to.

> But we couldn't figure out a way to procure drivers.

I briefly worked for Grab the company, which was another SE Asia "Uber". Among other things, at one point they procured drivers in Saigon by giving the wives/families free chicken meat. This way, they could prepare the drivers meals to take while they were out on the road all day long.

Kind of a local spin on tech workers free meals.

Of course you're not a failure. You still put food on the table, provide for your loved ones, and have a roof over your head.

You've got battle scars, and stories that are worth their weight in gold. Your experience is probably extremely useful for the right startup.

When going through crazy stuff as a founder, I always thing "this is going to make for a very intersting story some day". Looking back I doubt I'll remember them all and, while keeping things in full throttle, I wonder if I'll ever get to write about anything...

My conclusion is that most interesting stories remain burried and we're lucky to see anythign real (as in true stories) surfacing, because people that are crazy enough to enjoy these pains, hardly have any time to write about them.

Meanwhile we're presented with a somewhat skewed reality that's both less interesting, less real and overly biased towards glamor. The title of a somewhat :) unrelated book keeps popping in my head "Reality is not what it seems".

>Failure #5: “One by one, every bank that had initially responded positively changed their minds. Worse, not a single one of them would tell me why.[…] I never got a straight answer from any of the banks about why they changed their minds.”

Is anybody around with enough insight in that business to make an educated guess as to what happened?

There are many reasons to do a startup, but people should only call it a business when the goal is either a tax deduction mitigation and or rapid entry into profit traction.

1. Don't use some clever or hard to remember name with a weird spelling. While easier to Trademark, the users and customers won't differentiate your site from the sea of attention grabbing garbage.

2. If people have zero paying customers, and zero revenue... than the hard fact is they were never in business, and should have founded a nonprofit instead (common for opensource support service entities.)

3. Often copyright and patents are infeasible for small business, and people simply can't build or defend things like a large firm. Thus, initially design products/services to last maybe a year or simply be disposable... When 270 desperate cloners show up to dilute the market sector... people quickly understand why they can't rely on Android, Steam, or Apple ecosystems to protect their bottom line.

4. There is zero loyalty without treasure. The only people that care if your firm goes into the red is you, and maybe the small-time shareholders. Most people can't take the constant adversarial posture with problematic staff, opinionated shareholders, and high-demand customers. Everyone thinks a CEO is lame till you become a CEO for a year or two... Every conversation from that point on is about money or marketing, and most people keen on building things tend to burn out of the role eventually due to social isolation.

5. No company lasts forever, if the operation is a projected liability it is your job to respond accordingly. Even if that means executing an exit strategy, and firing the entire problematic division.

6. Ask business people about their memorable experiences, and not about their money source. The superficial apparent function of a business is usually very different from the actual revenue model.

Best of luck, =3

Very entertaining!

I'm always struck by the sheer serendipity of these stories. It appears that everything after Google was possible because of the safety net created by Google's IPO, and the author's time at Google itself ultimately came about because he and Urs hit it off over Lisp and Smalltalk. What would hace happened if the author had been allergic to dogs and had ended up at JPL because of their Fortran skills?

> Why don't the banks care? Because they treat the cost of fraud as just another cost of doing business, and they pass it along to you, the consumer. And they do it in a diabolical, stealthy way that you don't notice. But that's another story.

Desire to know more intensifies

It's interesting how at least several of the failures were good ideas with bad timing/execution that others have replicated successfully.

iCab: Uber obviously was very successful with this ~same premise

Smart Charter: I assume you can easily book a private jet online now?

Founder's Forge: linking record-keeping and payment is what makes Ramp great; 10 years of fintech innovations made executing this much easier

Spark Innovations: this is basically the premise of Airtable

That was a good read. What impressive perseverance, and also a positive outlook. But, reading it made my FOMO worse. I guess one has to experience it fully to apply it. Or maybe not.

I quit my job a year ago to pursue my own ideas. Like the author, I had made some money from a IPO. The post-IPO environment with heavy bureaucracy killed the vibe and I quit. Note that it wasn’t a Google tier company, but I made enough money that I could take a risk for some years without income.

For me it has only been a year. But I feel like a huge loser at times. In no scenario will I give up until I’m utterly defeated or captured the castle - I’m not a quitter. But this feeling gnaws at my soul.

I have failed to find a co-founder. Most of my friends are not interested in startups. So, I have had to look elsewhere. Between people who screwed me over equity, people who didn’t want to do the work, and my own imposter syndrome (I’m from a low ranked state college, and people I meet in SF are elites), I feel horrible and alone. I tried and even successfully built some projects over the past year, but ultimately nothing worked out.

Now, I’ve decided screw it. All the advice about sell first and get a co-founder - sounds great on paper. And I have some doubts around that whole belief but that’s not important.

I know actual pain points I’ve faced in my decade long career. I’ve done both highly technical and highly functional work. I’ve talked to enough people and validated my idea. I wish this thing existed and that I’d worked on it sooner instead of trying something different with randoms.

So, I’m just going to go and build it. I like building things, and I’ve gotten enough recommendations and performance reviews that point out that I’m good at delivering value for the customer and making sure my team succeeds.

So I’m building a product. I am able to dogfood my own product as I build it which is great. It’s a somewhat complex, b2b AI enterprise product, and having built multi-billion dollar enterprise software and delivered multiple multi-million dollar implementation projects, I feel that there is really no rush. Most enterprise software and organization processes are awful and not well engineered nor well thought out.

If this fails, whatever. I tried. If it works, amazing. I like building good things and have a track record of doing so, albeit for others.

But I fear I will keep feeling like a failure until it is successful. On the other hand, it would be very cool to build a solo founded enterprise product and deliver actual success.

Anyway, thought I’d share my thoughts it feels good to type it out. Thanks to the author of the article for sharing.

The difference between a failure and a success when starting a business is if you can afford (monetarily) to fail. if you can afford it just keep failing till something sticks. If you're not well off, well, too bad.

You're definitely not a failure, but maybe startups aren't your thing. There's no shame in that. I know I would never be able to start my own startup. You tried 6 times and every time it has failed, and it's clear that things like living close to the beach is a very high priority for you (I wish I could pull that off). Maybe it's just the universe telling you to get a good paying job and give your family some stability until you retire?

> To this day I'm pretty sure that plan would have worked if we had actually executed it. It was a brilliant plan if I do say so myself. In fact, it was so brilliant that it convinced Richard Branson to acquire the company before we launched for $10M. We started the company as Smart Charter, but we launched as Virgin Charter.

It's noteworthy that he's portraying selling before launch as a failure, and while ultimately the acquirer didn't follow his vision and the business didn't pan out (and perhaps the author never even got to liquidate his shares), it's still arguably more of a success than Loopt (raised $39M, sold for $43.4M), which Sam Altman and his backers had no reservations about portraying as a huge success that springboarded him to YC president and later to AI kingmaker.

What a fun read. I hope you'll try again!

“If at first you don't succeed, try, try again. Then quit. No use being a damn fool about it.” ― W.C. Fields

Winston Churchill's words, “Success consists of going from failure to failure without loss of enthusiasm.”

To everybody reading this and having doubts about starting your own venture: DO IT!

Yes it's a lot of risk, yes most startups fail, and yes you could make more money at FANG. However, this is one of the most exciting times to build a startup, thanks to AI.

The big winners of the all the AI advancements (especially OS) are devs and AI startups:

- No more vendor lock-in

- Instead of just wrapping proprietary API endpoints, developers can now integrate AI deeply into their products in a very cost-effective and performant way

- Price race to the bottom with near-instant LLM responses at very low prices are on the horizon

It's as if your product automatically becomes better, cheaper, and more scalable with every major AI advancement. This leads to a powerful flywheel effect: AI improves product -> better product attracts more users -> users generate more data

Besides the product perspective, AI also allows you to operate your startup a lot more efficiently.

Will we see a single-person unicorn soon? Very likely not.

Will we see very successful small and bootstrapped startups? Yes, already the case.

Very interesting story. Especially the bit about impostor syndrome.. to most people he had already secured enough skills and experience for a lifetime of confidence.. but turns out we all have our own measure of skills and success.

Thanks for sharing

Author here. AMA.

Those with no failures never tried. Now I'm the complete opposite of someone who would usually say that but I believe it to be true. Failure at things is ok, it's just part of doing stuff. Just like death is an outcome of life. Anyone who tells you they have never failed either hasn't ever tried anything or is a liar and protecting their ego. It's ok to admit you made mistakes or failed or that you don't know something.

I thought this was a very powerful meta learning, something that abstracts across all the experiences.

> And I think my current happiness stems mainly from the fact that I like the person I've become, someone who can fail again and again and again and again and still find a way, for the most part, to be happy.

Curious if you have any other learnings that are less specific to a particular endeavour but hold tru/derive from your experiences across all of them

It’s important to think not in terms of success or failure, but in terms of philosophy and mistakes. If you’re focused on the outcome there isn’t much you can improve on, the reasons for failure are many. Mistakes on the other hand stem from flaws in your philosophy, which you can readily revise. In a lot of the cases presented here, the mistake that stands out is working with the wrong people.

Multiple "diabolical" (his word, not mine) plans to fool people about what the business really is (an attempt to get in the door with one pitch, then pivot to the real plan and steal their lunch) did not work out. Sorry about that, but putting out this post won't help this guy execute on similar plans in the future.

Mostly very insightful article, except for one thing: the reference to the early 1990s recession as ‘the first Bush recession.’ Ancient peoples would sacrifice their kings when there was a drought or a bad harvest, and we are not much better. Presidents do not actually control the economy, and neither do governments in general. Granted, they have more effect on the economy than ancient kings did upon the weather. Still, economic cycles move mostly on their own.

And of course that 1990s recession ended in March 1991, in roughly the middle of Mr. Bush’s term (he left office in late January 1993): one might just as well refer to ‘the first Bush recovery.’ Neither moniker is really accurate: ‘early 1990s recession’ is best.

> In the real world, research is not a Platonic quest for objective truth. It is, first and foremost, a human endeavor, deeply intertwined with human ambitions and foibles, including my own.

Such a painful thing to realize, this is also the reason why I never attempted to do a PhD.

-I failed six startups attempts, (btw I'm multi-millionaire)

Americans are weird :)

Also remember that your fail state might be someone else’s success state. Like being part of an IPO that lets you spend the majority of the rest of your career working in your own ideas.

Thanks for writing this, I enjoyed every one of these. Something that jumped out at me from these attempts is the lesson that when you want to take on an entrenched business model, you need to do it in a way that isn’t directly at odds with the existing model. Secondly, you seemed to learn that and apply it brilliantly. I would love to know what went on behind the scenes of those banks deciding to pull the pin on your idea for startup forge.

Great article. We hear so much about the unicorns of the world that we sometimes forget about the countless other failed ventures. In these cases, it doesn't mean that the idea was bad, or that the founders weren't good enough. Sometimes it's just that luck wasn't on-side.

This author has never seen failure. Well, their only glaring failure is their lack of self-awareness.

Thanks for the interesting read! How did you support yourself through all of the failed startups?

I learned one of the most important lessons from six (and a half) failed startup attempts:

Brilliant ideas are not enough. You also need a brilliant mindset, vision and execution. And the help of a sensible co-founder if needed along the way.

Failure here too I guess but my downfall per my experiences in dealing with many who made it to the biggest names in tech is my morality. I can't lie/cheat/steamroll over ppl to get to the top.

Do people that create startups have debt in their own name after the startups fail? Or does the debt go down with the company and does the founder walk away debt free?

> Spark Innovations

As I understand it, the competitor in this space is Anaplan.

> ...even a long string of failures in specific endeavors doesn't necessarily translate to failure in life.

I needed to hear that!

There is one other way in which you are not a failure, and I am sure that I am not alone in thinking about it: I have been reading your words for 15 years, from the time I was a baby CS major. That's really true, e.g., here[1] is a comment from 11 years ago where I mentioned that a lisp you wrote for the Apple //e informed a lisp for the Apple //e that I wrote.

Especially in my college years (2009-2013, ish), the world seemed smaller, and to me, a lot of what you wrote was like looking through a keyhole into the real world. Grown-ups can apparently write lisp at JPL[2]! Google was chaotic[3][4][5][6] to work in 2000, especially if you commuted from Burbank. A name change[7]. And, variously, surveillance, more lisp stuff, etc. Now I'm an adult and I still haven't professionally written lisp, but I'm glad to have read about it anyway.

Anyway, it might surprise you to learn that when I think of your writing, though, I think of your HN comments first. There is a kind of influence that you can only get with a steady, unthanked build-up of seemingly-small contributions over a long period of time. In the right place they compound. I probably cite you to other engineers once a month or so.

[1]: https://news.ycombinator.com/item?id=6199857#6200414 [2]: https://flownet.com/gat/jpl-lisp.html [3]: https://web.archive.org/web/20080212170839/https://xooglers.... [4]: https://web.archive.org/web/20090408003924/http://xooglers.b... [5]: https://web.archive.org/web/20090408013612/http://xooglers.b... [6]: https://web.archive.org/web/20090408003913/http://xooglers.b... [7]: https://flownet.com/ron/eg-rg-faq.html

I’d say what actually made his ventures fail is his Google shares.

Having a fallback scenario doesn’t allow for the complete focus and ruthlessness to succeed at company building.

Weirdly I know the SVP Eng at that Virgin charter company.

The great thing about this article is that they talk about startups dying before they even really start …

I think this is the common case that’s never talked about.

One of the failures is selling a business to Richard Branson for $10 million.

Damn, one year at google and the author was basically set for life.

You only fail when you don't learn from your mistakes.

building a business is much more than having a great idea. Its a different skill by itself. Skills PhD's don't prepare you for.

seems his problem is mainly marketing and finding product market fit. I suffer from the same syndrome

With 6 failures and no successes I don't want to k ow what they think, its like some kind brain virus.

So few…..

(n+1)th time’s the charm

you can be a failure depending the time interval used.

I've heard from top investors that the best companies usually get immediate and rapid traction. Sometimes theres a figma story where it takes a while, but thats usually BS. Generally either the product is right, or its not, and you know very quickly.

They usually dont want to tell founders this, they want them to struggle through in the off chance it works

How are any of these not failures?

> Growing up, I had two major life ambitions: to become a tenured university professor, and to found a successful startup company.

why the hell those two?

I eventually - into my thirties- worked out that i wanted to be a good computer programmer, and a good photographer. managed the first, but not the tatter - two bored.

What I mean, is why did you have those ambitions growing up. I don't think most normal young people really can't think what they want to do until later in their lives.