top | item 42771676

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

547 points| lisper | 1 year ago |blog.rongarret.info | reply

313 comments

order
[+] kevmo314|1 year ago|reply
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.

[+] robomartin|1 year ago|reply
Sometimes wins are not necessarily measured with financial success. A company can utterly fail and still represent a win. I had one of those.

I started a self-funded tech company around 1998. This was hard tech, hardware and software. And I was the sole engineer doing all the work. This meant 18 hour days, 7 days per week to get the plane off the runway. Two years later, after booking lots of sales, we finally moved out of the garage and I started to hire people. Yes, I ran this beast entirely on my own for two years. A few years later a large well-known company expressed interest in acquiring the technology. The number being floated was in excess of $30MM.

What happened?

Well, 2008 happened. The economic implosion caused this company to second-guess entry into the market we had pursued --which they intended to do by acquiring us. The deal went from being a couple of meetings away from an acquisition to evaporating in front of my very eyes.

The bad news was that the economic downturn truly hurt us over the next couple of years. I had to shut it down in 2010 and lick my wounds.

This thing went from pouring all of our savings and an incredible amount of very hard work into a crazy idea, executing well enough to get a $30MM+ offer to closing the doors and nearly losing it all in the process.

At the time this felt like an abject failure and a waste of ten years of my life. It took me months to get my head back on straight. Today, looking back, I see it as a success. I took an idea from nothing to close to a massive life-changing exit and did so mostly on my own through hard work, grit and determination. That's a success story nobody can take away from me. I learned a lot along the way and most of those lessons were part of success in future endeavors.

Life can be funny and cruel sometimes. You might think you are going through your darkest hours when, in reality, you are growing a solid backbone that will support the rest of your life.

Entrepreneurship is hard. Very hard.

[+] jebarker|1 year ago|reply
Ugh, I know this feeling too well. I've been pretty successful in life so far by societal standards but have always felt inferior and like I'm failing. Always. I think partly that's responsible for the drive that enabled earlier success, but it gets old. My first defense when those feelings bubble up is to remember we're all playing a game we can't win!
[+] ChuckMcM|1 year ago|reply
Yeah, the "success definition" trap is real. For me I was having coffee with a former co-worker who was now a VC because they had been at one of the same companies I had been but had joined "pre-IPO" and so probably had a net worth of 20 - 30 million. They asked what I was looking for and I said "To be successful like you!" and they said, quite seriously, they would prefer to be successful like me. And at that point we talked about the parent's point of how do you define success? This person had money but had lost their their spouse to divorce over 'working too hard' and were now alone. Meanwhile my third kid was on the way and I was doing okay but certainly not "FU money" okay. And yet from their perspective, that was more successful than they felt. That really threw me for a loop.
[+] morgante|1 year ago|reply
Also interesting that it seems like his relatively minor 1 year stint at pre-IPO Google was successful enough to pay for many other endeavors.

It's a great example of the power laws in startups: it's much more lucrative to have a minor role in a major success than a major role in anything minor.

[+] ErigmolCt|1 year ago|reply
It’s liberating when you realize that the "arbitrary label" of success or failure is often just a narrative we construct around events
[+] slashdev|1 year ago|reply
I remember an old Steve Jobs biography titled “the journey is the reward”.

Overtime, I’ve come to appreciate that statement more and more. I think it is an incredibly profound insight about life.

[+] hinkley|1 year ago|reply
I’ve had a lot of coffee breaks with highly placed peers who expressed concern because our boss was sure our success came down to one or two attributes and seemed completely blind to all the ways we saved him from himself. If apathy ever took over the team, we would burst into flames because of all of these details.

There’s a great old aphorism that sounds like sarcasm if you don’t understand this: “Take care of the little things and the big things will take care of themselves.” Any halfway sane team is dominated by people who are all too happy to jump on the Big Things. But for want of a nail, the kingdom can be lost. And if you cannot see his importance, and fire the farrier to hire more knights, then everybody loses.

[+] jackcosgrove|1 year ago|reply
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.

[+] tptacek|1 year ago|reply
This idea comes up here every once in awhile (often in the form of "a batch of startups where some % of the stock is shared across the batch).

I'm not saying it can't work, what do I know, but a challenge you'll have to address here is:

* By the time you're at the first big-money investment, the priced A round, you're dealing with investors who make just a couple investments a year.

* Despite that, the most promising startups are chased by VCs, not the other way around.

* If you're one of those promising startups, what would motivate you to take money from the investor structured the way you propose?

Most returns in startup investment come from a small fraction of breakout successes. Even if you got, like, 25% of startups to join this kind of funding compact --- which would be a huge, a momentous achievement on the same scale as the creation of YC --- the math here might not work out to where the shared-fate component of the deal was meaningful for any of the failed startups.

[+] andix|1 year ago|reply
There's your startup idea: communist ycombinator. ;)
[+] yobbo|1 year ago|reply
What if startup founders and employees are paid in shares of the investment fund?
[+] joe_lin|1 year ago|reply
Well, having been in an accelerator there were folks (startups) in my class who shouldn't have been there. i.e. their startups failed but it was blatantly clear why -- mainly immaturity and not listening to advice.

I think your idea would only work if there were rigorous selection process, but also some mechanism to "fire" founders who aren't contributing or insist to make terrible decisions.

[+] hiAndrewQuinn|1 year ago|reply
I'm not really sure I would feel comfortable investing in an accelerator class concept like this. Seems like it would suffer heavily from adverse selection.

Maybe if the terms were really good, like 20% of the company for $10,000 or something.

[+] WalterSear|1 year ago|reply
Not having to remunerate failed founders and starting employees for their effort is a cornerstone of the VC business model.
[+] tiffanyh|1 year ago|reply
1. This is Socialism

2. You’re not creating the correct incentive system. It creates the opposite incentive you want - it rewards those people who do nothing and let others do all the work. You could easily get in a situation where all people in this co-op do nothing, under hopes someone else hits it big.

[+] jfengel|1 year ago|reply
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.

[+] seany62|1 year ago|reply
> My main lesson from running a startup: don't.

I hear this a lot and I think it is good advice because the only person who should actually start a startup is the one who sees this but still does it.

[+] financltravsty|1 year ago|reply
Always baffled me how little commercial sense HNers had when I was growing up and reading this forum.

It's as if no one taught them -- or they just don't have the sense for it? -- that a startup is just a vehicle to make money. There's nothing special about it. You can make lots of money without a "startup." You can make lots of money doing many different things even without a business entity. It's just an abstraction for linguistic convenience.

My biggest wakeup was finding people much less educated and much less intellectually gifted and much less socioeconmically privileged making a lot more money than what could be considered their betters in more prestigious and, on the surface, well remunerated professions.

If you don't want to make money, don't go into business. Stay at your job and grind a career out. If you have the desire to make money, your senses will naturally sharpen as you use them more to achieve that end. Otherwise, if you go and "build a startup" for any other reason than making money you will fail barring extraneous circumstances.

Baffling that this isn't common sense, really. But my fault. I keep forgetting a professional forum is just a proverbial water cooler, where you get to see a wide mix of people in your profession -- and all the different backgrounds, values, ideas, and ways of seeing the world -- most of which are continuous works in progress that culminate only at death.

[+] edelwiess|1 year ago|reply
I dont understand why starting an enterprise has become such a scary thing in the tech world. So many people start businesses, so many mom and pop shops etc. IMHO startups have become scary to start because we jump too quickly into starting them or have too grand expectations from outset.
[+] satvikpendem|1 year ago|reply
Funny how things change over time on Hacker News, an ostensibly startup forum that now more and more seems to be just another tech forum, and any relationship to YC and startups is now merely incidental, it seems.
[+] cheinic63892|1 year ago|reply
> My main lesson from running a startup: don't.

Worse than failing is not trying.

You will live your life always wondering “what if”.

When you fail, you will have an answer to the above question and can live in peace.

[+] 999900000999|1 year ago|reply
I'm starting to think you really need to be well connected or at least come from an upper class background to win here.

Steve Jobs is sort of an exception here, not only was he adopted , but he was adopted by a very middle-class family .

I find myself really good at developing small apps, but very bad when it comes to the business side. I would love to find someone to work with who's good with business. But so far I've just been time scammed a few times by morons who come up with insanely impractical ideas .

And they never want to let you in for a full cut, they want to give you like 1% of the company in the event that you're able to build the entire thing out from scratch. If you discuss modest technical limitations they'll berate you for corrupting their vision.

[+] duxup|1 year ago|reply
I'm on the ordinary working job track. I like it.

But if you're young, got the time ... I think it's worth a shot, or two, or more.

[+] ErigmolCt|1 year ago|reply
The narrative around startups is so often shaped by the success stories that get the most attention, but those stories are the exception
[+] tschellenbach|1 year ago|reply
Personally I think it's about perseverance, but mostly with an emphasis on learning and growing. You iterate, you learn and you eventually build up a skillset that is hard to stop even if things don't go your way.

It's not for everyone though. Bar is super high, risk is high, long work weeks with little balance are the entry ticket.

[+] icedchai|1 year ago|reply
I agree. Toughing it out usually doesn't pay. I was at a startup from "birth" (first employee and lead engineer) to "death" (acquisition for pennies on the dollar.) The first couple years were exciting, super fun. We built a great team, had an interesting product that solved a niche problem, several early customers. But the business model just didn't work out. It wasn't enough to sustain a real company. The downward spiral began...
[+] mlacks|1 year ago|reply
What happened to Hacker News man
[+] dennis_jeeves2|1 year ago|reply
>And if you do, quit when the going gets tough. Perseverance does not pay off.

Rare, wise words. (in a world, where 'follow thy dreams' philosophy is venerated).

[+] jimbob45|1 year ago|reply
Would you feel the same way if you had effectively infinite money? (e.g. you were Bill Gates' secret daughter he sends a million to each month).
[+] latchkey|1 year ago|reply
> 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.

[+] NickC25|1 year ago|reply
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.

[+] random3|1 year ago|reply
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".

[+] gond|1 year ago|reply
>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?

[+] Joel_Mckay|1 year ago|reply
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

[+] kjellsbells|1 year ago|reply
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?

[+] gruntledfangler|1 year ago|reply
> 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

[+] morgante|1 year ago|reply
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

[+] babyent|1 year ago|reply
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.

[+] superkuh|1 year ago|reply
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.
[+] blindriver|1 year ago|reply
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?
[+] _zagj|1 year ago|reply
> 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.

[+] sinoue|1 year ago|reply
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

[+] justmarc|1 year ago|reply
Winston Churchill's words, “Success consists of going from failure to failure without loss of enthusiasm.”
[+] hubraumhugo|1 year ago|reply
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.

[+] agumonkey|1 year ago|reply
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

[+] lisper|1 year ago|reply
Author here. AMA.