I remember as I was starting my company, I reached out to a founder of a company you've likely heard of for advice. We grabbed drinks, and he practically begged me to not start a company, for my own sake. I thought he was a dick.
But he wasn't wrong. Write down a list of why you want to start a company. I bet the list involves things like "building something nobody else has," "getting to program and design and do a bit of business-y stuff" or "freedom to work on what I want". That's only true when you start. Pretty soon, you're spending all day in meetings, and only a small portion of your time will go to the things you currently enjoy doing... and you'll feel guilty because there's something more important you should be doing. (Me? I'm currently procrastinating on an investor update, an H1B application and two performance reviews.) You'll spend more time writing emails than writing code. You end up bogged down in organizational issues, not dreaming up cool new features. Rather than having one boss, you now have dozens... investors, customers, employees, etc.
Oh, and the rejection. The non stop rejection. Every single day, hour, minute. Investors, customers, employees, potential employees. It's not personal, but it sure feels personal. Even when things are going great, there's tons of little micro-rejections, non-stop. I wish someone told me that.
It's really hard. I don't know a single founder who hasn't had relationship problems because of their company, or suffered from depression. Hanging out with founders is less like the TV show Silicon Valley, and more like group therapy.
This isn't to say you shouldn't do it. But just be prepared for what being a founder actually entails. Talk to a few founders of medium sized companies about how they're doing. If you're still on board, then maybe you're right for the job. For me, I wouldn't change a thing... I love it. It's incredibly hard, but there's a reason I haven't even thought of leaving. If you're the same way, then go for it!
But don't do it because you want to do it. Do it because you literally can't imagine not doing it.
(If you're doing it now and things are getting hard and you need someone to talk to, my email is in my bio :) )
Yeah, that's how I've always expected the VC-Backed-Startup world to work. It's fascinating to me to watch people going into that, expecting it to work out for them.
It's like watching somebody take up smoking. You can watch the history of people doing this activity as far back as you like, and just hardly ever come up with an outcome that seems to make your life genuinely better. But with lots of examples of it making your life worse.
That's not to say I'm against starting a Business though. I've been into bootstrapping SaaS products for the last dozen-odd years, and that absolutely has made my life better in lots of ways, including those on your list of Reasons To Start A Company.
The big one for me is Free Time. If you stay small, things work out really nicely. Every dollar past breakeven adds to your personal salary. No dividing by 2 or 3 or 10, so a little $10k MRR niche is all you need to be set for life. That's the kind of niche that can be serviced with a few hours of support mails a week (once the thing is built, of course), which means a lot more freedom to go do whatever else you want.
I'm surprised this isn't talked about more. Trading your job for a VC-backed startup is just changing one master for another, with a more uncertain outcome and better upside.
I came to the conclusion I'd much rather own 100% of something small than 10% of a Unicorn. So I changed to part-time work to cover the bills and I'm bootstrapping. I think if I'm ever successful enough to need an HR department, I'll sell the business and move onto the next thing. I don't ever want to spend less than 50% of my day knee-deep in the actual code.
The biggest reason that so pushes me away from VC funding. One Pre-Seed fund reached out, so, and I will most likely pitch the guys. Because VC money allows you to speed things up in ways you can't by relying on free cash flow.
That being said, I'd still prefer the latter becaus I don't want another boss (or multiple ones). Gess it depends on the conditions, so.
And good point about the HR-department moment, that's the thing I fear the most in getting to many customers!
Pre-seed? So that's what maybe $10-$30K investment? Save yourself the trouble and do some contract work for 1-3 months, you can make the same amount with no strings attached.
>Oh, and the rejection. The non stop rejection. Every single day, minute, hour. Investors, customers, employees, potential employees. It's not personal, but it sure feels personal. Even when things are going great, there's tons of little micro-rejections, non-stop. I wish someone told me that.
THIS! You feel like your back is always against the wall and you have to defend every product decision. You are right it's not personal and probably good the feedback(most of the time...) but you ja it's hard getting rejected 24/7.
And even criticism can later be seen as "rejection" :/ Maybe it's best to view these things not in isolation but on a timeline.. Sure many of the things I produce today, might still suck, but I think it sucks less than my products from 8 years ago. Growth is definitely there.
"You'll spend more time writing emails than writing code. You end up bogged down in organizational issues, not dreaming up cool new features. Rather than having one boss, you now have dozens... investors, customers, employees, etc."
why not hire a COO that takes care of it? Don't do jobs that you are not happy with for long. For some short time that is acceptable, but not for long.
I don't count my customers as by bosses. And as long as you don't give yourself the trouble, they are not your bosses. However it is important to focus on them, try to think about them and know what they need before they even know it.
Maybe "boss" wasn't the right word – I should have said "Rather than having one boss, you now have dozens of people you're accountable to... investors, customers, employees, etc."
And sure, hiring can make issues go away (I've definitely done it!), but I think you're missing my point – no matter who you hire below you, if you're the CEO, the buck still stops with you. You're the one ultimately responsible.
The lesser known truth is that the CEO role is often tedious "normal" work and not being Ironman. You can give in to that and hire a CEO that actually enjoys the meetings and stuff, or at least a COO to run the company day to day. Just because you founded a company does not mean you have to do everything but sure, the pressure to take responsibility is high..
Oh, and the rejection. The non stop rejection. Every single day, hour, minute. Investors, customers, employees, potential employees. It's not personal, but it sure feels personal. Even when things are going great, there's tons of little micro-rejections, non-stop. I wish someone told me that.
Yep. That's been one of the toughest parts of the whole process to me. Probably the toughest. That and the fact that nobody else (unless they've been through the same process) can really understand what you're dealing with. It results, for me, in a very lonely feeling at times.
It sounds similar to the advice for a number of other disciplines I've seen in my family tree: classical musician and ministry. That is, you do it because you can't imagine doing _anything_ else because the dedication you need to succeed is so great it crushes almost anyone with less than fanatical devotion. But being a successful founder in tech has on average a _lot_ better rewards and social recognition overall than either of the other "tournament" style careers out there, so it's worth the downsides.
The attitude is essentially that of "Find What You Love and Let it Destroy You" quixotic work-centric nihilism that seems both understandable yet ridiculous. For folks that ascribe this worldview though, I do expect them to do fairly well in whatever they do... and to be miserable to be someone unfortunate enough to love them.
> But don't do it because you want to do it. Do it because you literally can't imagine not doing it.
What about because you can't bear the thought of having to work 8 hours a day for the rest of your life? I realize this is probably among the "bad" reasons to start a business (and it probably sounds disrespectful to people who have and will keep on doing that until retirement), but that is how I feel currently.
It may sound like a burnout problem, but there wasn't anything to be burned out by except... having to actually work full-time. I now freelance 10-15 hours per week and that feels doable but I'm not going to have a fun retirement with that (at least living expenses are covered).
It is a valid reason. Some people start companies to actually make money. If that is your motivation it can be very powerful. I would also say that it’s going to be (probably) years of 12+ hour days that might end in failure.
Thanks. Somehow that doesn't sound as bad, as long as there is reasonable (whatever that means) chance of it working out. Although, logically, it's clear to me that it is harder than working a job. Only way to know is to do it, I guess.
And maybe see a therapist, because this dread of having to work sounds weird now that I put it in writing. And I did it for many years without seeming to suffer too much, at the time at least.
You have to at least try to find a path toward self-actualization at your current job. Depends on how your relationships are with your various coworkers. For example my personal experience is this: Last gig was a startup, but I was stuck with the wrong people. It only takes one bad apple in your group of cofounders to generate enough chaos to plunge the whole thing into the ground. Since I bailed, I started working 9-5 at a job that pays me more than I've ever been paid and I split my time here working on 3 different projects which are all exciting and which I have a good deal of creative control over, and I enjoy working with every single one of my coworkers. It is my belief that the most effective way to move yourself toward the working environment that you want to have is to shape yourself in the image of the type of person that you want to work with. In my experience that has something to do with experience and knowledge... so I do not shy away from opportunities in which I can expand my experience or knowledge especially in the topics that I'm passionate about. And it's also important to proactively share your experience and knowledge. That one is the most genuine way to demonstrate that you know your stuff.
The article is specifically about VC-backed startups, so I was speaking to that. If you’re worried about burnout, don’t start a company. I take a lot of time off, but you can never really shut your laptop off.
That being said, a smaller drop shipping company or something similar could work!
Yep, I know someone who did this, but without a FAANG job, living in a relatively low cost of living area. It took 15 years to get to the first million, and roughly 20 years to get to two. You need to be able to handle a lot of ups and downs, like the dot com crash, great recession, and now corona.
A lot of people, quite understandably, can't deal with that sort of volatility. You'll see $100K+ drops in a month. You'll also see 6 figure gains, of course. Some people give up, put it all into bonds. That's not good, either.
">Oh, and the rejection. The non stop rejection. Every single day, minute, hour. Investors, customers, employees, potential employees. It's not personal, but it sure feels personal. Even when things are going great, there's tons of little micro-rejections, non-stop. I wish someone told me that."
That was definitely the case with my first startup when I was younger. In my second business that I started 10 years later, I couldn't care less. Most of the time such a feedback is given by people who aren't my target audience and who thus don't have the pain that people I target have. If your target audience rejects you, you have a big big problem.
Not all of them but certainly a few of them. Growing a bootstrapped business slowly meant fewer rejections, less stress about expected growth (hiring, sales) and more control over your role at the company. But eventually you'll hire employees and you will spend less time writing code. I wouldn't necessarily say that's bad though as you might discover that some of those other aspects of running a business are even more satisfying. And you can always make time if you really feel the itch to program something again (once you've hired people to handle support/ sales).
I generally encourage interested people to start their own companies. But I advise against taking VC except for a few use cases that make bootstrapping unrealistic.
I woke up with knots in my stomach for months thinking about the things I would have to do to get customers and the non-stop rejection the day would hold as I worked to get a foothold for my startup.
There was no VC to call me to account, or VC firm to help with areas you I didn't like or couldn't do.
If I hadn't been able to hold myself accountable to do the things that I dreaded my startup never would have gotten off the ground.
I've bootstrapped several businesses. The stress is there but its different and highly depends on the situation (how much money you have saved up, what market you're in etc.)
> you'll feel guilty because there's something more important you should be doing. (Me? I'm currently procrastinating on an investor update, an H1B application and two performance reviews.) You'll spend more time writing emails than writing code. You end up bogged down in organizational issues...
Somewhere out there in the world is someone incredibly excited to do just that. They aren't necessarily an "ideas" person but wrangling org just get's the heart racing. It's a shame that they're as hard to find as good ideas are
Do you think some of these issues could be ameliorated by setting out guidelines in the very beginning such as sticking to a simple business model, saying you won’t scale past a small size, and outsourcing business-related work to 3rd party services? Many engineers probably identify with your quotes about “building something no one else has” and “freedom to work on what I want.”
I think many of us would find guidelines like that useful! Because to a corporate engineer drone like myself, starting something small like Pinboard sounds rewarding.
Yeah! I specifically was using the YC definition of "founder" here (VC backed, etc), since that’s what the article is about. Indie hacking is a completely different ballgame!
I've started a few other companies in parallel (for example, https://startupescape.com/) that collectively earn similar to my company salary, and take a few minutes a week to run. You have a limit on how big you can get and how much of a difference you can make, but if you're cool with that then it's definitely possible! In my mind, the only downside is that you're working alone rather than with a team – and it's really fun to have people to share the journey with!
This excerpt from Lex Fridman's podcast with Stephen Schwarzman provides a fairly good assessment of the situation...it's a rough ride. - https://www.youtube.com/watch?v=jdt4PPY09rQ
Some folks can handle many things at once and have a structured mind for progressing them all forward simultaneously. My wife had that kind of mind. I do not. I struggled mightily managing a company and ultimately tapped out.
Probably projecting here, but the imo the no1 reason to start a business is writing software for others does not scale, while selling software/service is lucrative.
But he wasn't wrong. Write down a list of why you want to start a company. I bet the list involves things like "building something nobody else has," "getting to program and design and do a bit of business-y stuff" or "freedom to work on what I want". That's only true when you start. Pretty soon, you're spending all day in meetings, and only a small portion of your time will go to the things you currently enjoy doing... and you'll feel guilty because there's something more important you should be doing. (Me? I'm currently procrastinating on an investor update, an H1B application and two performance reviews.) You'll spend more time writing emails than writing code. You end up bogged down in organizational issues, not dreaming up cool new features. Rather than having one boss, you now have dozens... investors, customers, employees, etc.
Oh, and the rejection. The non stop rejection. Every single day, hour, minute. Investors, customers, employees, potential employees. It's not personal, but it sure feels personal. Even when things are going great, there's tons of little micro-rejections, non-stop. I wish someone told me that.
It's really hard. I don't know a single founder who hasn't had relationship problems because of their company, or suffered from depression. Hanging out with founders is less like the TV show Silicon Valley, and more like group therapy.
This isn't to say you shouldn't do it. But just be prepared for what being a founder actually entails. Talk to a few founders of medium sized companies about how they're doing. If you're still on board, then maybe you're right for the job. For me, I wouldn't change a thing... I love it. It's incredibly hard, but there's a reason I haven't even thought of leaving. If you're the same way, then go for it!
But don't do it because you want to do it. Do it because you literally can't imagine not doing it.
(If you're doing it now and things are getting hard and you need someone to talk to, my email is in my bio :) )