I cofounded a startup that was eventually sold for $64 million. My cofounder forced me out of the company and stole all of my equity from me, costing me nearly $13M. So cofounders are not all they're cracked up to be.
As for the general negative tone, businesses fail - you don't, unless you quit trying. My advice: work on something with a short path to revenue for now, and stop taking yourself so seriously. After the thing with my cofounder, I had several ambitious ideas to make millions again, but those were failures and I was basically emotionally destroyed. So I finally made something with less potential, that was less interesting to me, but with a clear and simple value proposition for customers. I also developed a way to market directly to my potential customers for free. That business is now doing quite well, and the mere fact that people are paying for something I created has completely turned around the depression I was in.
Remember this: Walmart makes billions selling inexpensive crap that they buy from other people. Their innovation? They charge more for their products than they spent buying them. At least until you can afford to take risks on interesting, swing for the fences kind of stuff, get rich doing boring things. It's easier and faster.
This is very much part of my frustration. I put my pseudo-resume on CFL and got blasted with dozens of requests, so many that I had to put assholish "don't contact me unless" prerequisites on my profile. But here's the thing I've realized (and maybe you did, more painfully): I know not to get involved with a stranger or even an acquaintance that I haven't known for years. Finding someone who can produce at an obsessive, passionate level like you (hopefully) will is extremely difficult and riddled with risk. Heck, just finding someone who is a net positive is hard enough.
If you co-found with a non-bestie, not only are you taking all that risk on yourself, but investors are going to look the other way. They know it better than anyone: startup teams are like marriages. It can get ugly really, really quickly, completely obliterating the business in the process.
I have an unhealthy envy of some cofounding teams that just were, no work involved at all. It's like they took the undisputed hardest part of starting a company and just sidestepped it. Digital Ocean is a team of brothers, for example. Many big startups were formed out of happenstance high school or college buddies. But guess what? When you grow up in a tiny town in flyover country where entrepreneurship is unheard of, those people don't exist. I did go to a top-10 university, but it wasn't particularly entrepreneurial like Stanford or Berkeley. Everyone I knew there is now a banker, lawyer, doctor, etc. My only engineering buddy from college has been at Microsoft for 12 years and has two kids, and even still, I've made several unsuccessful runs at him (and others).
I'm allowing myself to be a little whinier than I would under a real account, so sorry if it sounds ultra-negative.
Meh, in for a penny...
Dear God I hate the concept of marriage. It has stolen all my friends and all my potential co-founders. I secretly celebrate divorce.
I knew him very well....for about 5 years beforehand, and there are few entrepreneurs that come with a better resume and bankroll (which is why I agreed to take 20% of the company as a cofounder - he put up all the money and his history and contacts all but assured a successful exit).
What I didn't really know about was his temper and emotional issues when it came to business. He was essentially a completely different person. I thought I knew him well, and it turns out I wasn't even close. The beginning of the end turned out to be when one of his 7 ex-fiances (not exaggerating here btw) started flirting with me at a party and kept contacting me even after I told her it was a bad idea. I didn't reciprocate, but it didn't matter. After that, it all went downhill.
I co-founded a company with my best friend in high school. He screwed me 6 months into the biz. As an individual, the fires of entrepreneurship completely changed him.
Seriously. There are some niches where a given amount of work can reliably produce $100, $200, $500 in recurring income. It's not going to let you retire, but who wouldn't say no to getting that much extra per month?
And then you can repeat the effort, and it adds up.
I don't love that term, but people know what it means. You can make a business that doesn't depend on traction and scale.
Find a prosaic need, and serve it. Could start with consulting, or products. Start small, stay small by Rob Walling is an excellent primer, as is the four hour workweek. The latter glosses over how much effort is actually required to make a "muse", but the mindset is spot on.
I'm currently doing this. I'll never get a $10 million payout, but I've built good revenue streams and have complete freedom of time.
And I did it without knowing programming. You've basically got a superpower in the internet world. You can program AND you have a baseline of entrepreneurial knowledge.
Just shift out of startup mode. As long as you've got enough money or time that you can work on something new without starving, it's not THAT hard to make a business that gives you freedom.
(No guaranteed success, but the odds are significantly better than in a startup. This talk by DHH is a good overview)
1. Small business - Bakery, barber shop, golf store 2. Lifestyle startup - Unique product, smallish market, little chance of liquidity event 3. Venture - Startups with the potential for massive, fast growth
Every time I think about starting #1, I dismiss it immediately. I see it as merely the illusion of freedom.
A girl from my hometown opened a Pure Barre. Sure, she doesn't have a "boss", per se, but she's still working like a dog to send most of her money to the .1% -- the rent she pays in the shopping center, the utility bills, the franchise fees, the Gatorade she sells from the fridge, the fridge itself, etc... and probably makes <$30k for herself.
There are exceptions, but generally I think the same thing is true of restaurants, bars, computer repair shops and franchisees of all stripes.
Having experienced #2, first-hand, I can tell you that it's much harder to do than it sounds. I think the universe wants growth or death in all things. Hanging out -- safely -- in equilibrium between them is a rare feat.
If you aim at a market that's a bit too large, you're going to get crushed by the big boys. In fact, there are myriad examples of large corporations butting into small markets first discovered by startups because, heck, why not? The big corporation has the resources to inject itself into the small market on the off chance that there's actually something there. It's like buying insurance.
If you aim at a market that's too small, then you don't make any money and you're on your own to pull it off because no (worthwhile) investor should want to get into a small market with MAYBE a $5m buyout years down the road. Ditto good co-founders and employees. If you're able to get investors and rock-star help, you're probably in "venture" territory, not "lifestyle".
What happens with a lifestyle biz is you end up turning a small profit and living on the edge, fearing that something doesn't go horribly wrong. One lawsuit... one legislative change... you, the lifeblood of the company, have a medical emergency... and it all goes poof.
Worst of all, you're stuck. Because it's a middling market, it's difficult to find anybody who could run it in your stead (they're at Google, etc), so it's always and forever on you.
Again, there are many exceptions. Like the guy who runs The Chive or the guy who runs Fark. It's possible, just harder than it sounds. If you're going to take all the risk and invest your time, why would you knowingly aim small like that?
No, for my money, #3, swinging for the fences, is the only way to go. Anything short of that is setting yourself up for years of anxiety and frustration with little chance of making real money. I'd rather put my money on red or black and see how it turns out quickly.
Please email me if this interests you.
It feels pretty stupid to reply to this as a "no", but to offset the incredibly depressing stories of random luck success, I figured I'd go ahead with it anyway.
No, I'm not rich. I'm 33 and dead broke, actually.
> How did you do it?
I started my first company (a video-related SaaS B2B product) at age 22 and it should have been a home run. The idea and timing were perfect and I found product-market fit almost immediately, cold-calling my way to paying customers 10 months after quitting my previous job.
But I fucked it up. I was too young. My engineering was shitty (wasted all my time putting out fires), but more damningly, I tried to grow the business organically. I'd never been exposed to "real" entrepreneurship before and didn't know anything about venture funding. By the time I realized I needed to raise money (and actually going as far as signing a $1M+ term sheet with a group of shitty investors), it was already too late.
The old guard companies in the space I set out to bankrupt did, indeed, go bankrupt, but it was another startup with the same idea and technology as mine that put the screws to them. While I was trying to turn a profit and make payroll, these other startups just passed me by like I was standing still.
>What did it feel like when you first realised it was going to be true that you would never have to work again if you didn't want to?
Re-interpreted as "what did it feel like when success slipped through your fingers?"
The business was doomed by 2006, but I "stuck with it" (following bad advice) and pivoted (more bad advice) until 2010 when I finally gave up. I wasn't exposed to the concept of failing fast until later.
There was no real moment in time I knew the dream was over, but I fell into a deep depression. Thinking funding was imminent, I'd borrowed money and found myself $75k in debt after all the work and sacrifice.
I finally pulled myself out of the depression and was able to pay back most of my debt within 2 years of being in the "working world".
> How old were you?
Company started at 22, on life support by 27, ended at 30. 2 jobs and 2-3 more startup attempts since then (one was a pivot, really). Now I'm 34.
> What was it specifically that made the cash that ended up in your pocket?
Like I said, I found product-market fit. Had I executed properly, as my competitors did, I'd be a multi-millionaire today.
I've tried to start 3 more companies since then, each better engineered and executed than the last, but none of them found the beginner's luck "fit" of the first.
What was different about the first? I experienced a pain point first hand in an obscure occupation. I don't want to get into specifics, but my first job out of college was as a peon in a non-tech industry. I saw a glaring inefficiency in one of the business processes and knew I could fix it with software.
Of my 3 product/usiness attempts since then, 2 solved problems I perceived from outside an industry that weren't really that problematic after all and 1 was/is a consumer product. For the consumer product, the problem I'm trying to solve is really a problem, but it's visible to many, many more people.
When you have a unique vantage point on an obscure problem, your chances of being the guy to solve it are much better.
> Do you feel happy in your life?
No. It gets really dark sometimes.
When I was running my first company, I was energetic and blissfully self-confident. Now I'm a heap of bitter frustration and anxiety with crippling sleep problems.
After I finally gave up pivoting and "persevering" on that first business, I had a 2-year "working world" tenure that was so painful I can't even talk about it under an anon account.
Entrepreneurship courses through my veins and I can't turn it off. But I've gone through my Rolodex of acquaintances a thousand times and can't find a viable co-founder for a new business. No cofounder = no accelerator = constantly stuck in neutral. The thought of going back to a cube job makes me break out into a sweat -- literally. (Echoing an above poster.)
All I can do at this point is try to start new businesses on my own and get traction like I did the first time. There is no other viable path for me.
TL;DR I was a 22-year-old wunderkind whose company crashed, career melted and am now a 34-year-old has-been.
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Epilogue: A friend of mine went to a state university and applied to his dream job at Microsoft upon graduating. He got rejected and ended up taking a position at his backup, Google... in 2002. Made a boatload (but not retirement money) in the IPO, was heavily recruited by the most hyped startup of the late 2000s (he admitted it was only because of the Google name), and is now an angel investor.
Life is fucked up and random, my friends. Signal and noise.