I was co-founder of my last startup at age 38. Exited at 48. Started with a wife, three kids, two dogs, one mortgage, and an IRA account. Exited with the most important things still intact (minus one dog and an IRA). The company's exit was a member acquisition deal and a fire sale of our IP. Far from glamorous. Far from a fairytale ending.
The whole experience was the hardest thing I've ever done.
It was also one of the most fulfilling professional experiences of my life.
I intentionally stepped off the corporate ladder to pursue this dream. But because of my prior commitments/obligations, I wasn't able to drop everything and go all in. That was a hinderance. It made things harder. It put a strain on my family. But it was doable. And even though we didn't achieve our ultimate goal, these complications were not the reason for failure.
I became an independent consultant that gave me an income with some flexibility to allow me to asynchronously lead our startup. I called the time outside of my consulting work "the nightshift". We raised a seed round that allowed my younger and less encumbered co-founders to work as FTEs. We took in more funds that added another six FTEs and an offshore team. Over the 10 years we existed, I never took a salary. When the chips were down and I needed to be 100% dedicated, I emptied my retirement account.
This arrangement was far from ideal, nor do I fully recommend it, but it gave us a shot. We built, tested, and learned our way to a product that served several million (non-paying) customers. We made plenty of mistakes. But we learned from them. We learned to be so frugal, so resilient. So incredibly nimble and innovative. I yearn for that kind of creative power again. It has prepared me to take on anything in life. I've never been to war or faced death with my comrades on a daily basis, but in business terms, I imagine startup life is as close as you can get. The experience has made me a better husband, father, friend, and colleague.
I've since returned to corporate life (for now). There I am invincible. None of it scares me. Corporate politics, bureaucracy, and general bullshit pale by comparison. My startup experience has become my superpower. Because I know I can help raise our game, knowing how to bring out the best in our people and to keep perspective on what is truly "hard" and how to get things done with less and under far less ideal circumstances.
So I say go for it. But go in with your eyes open. The odds are long no matter what. Might as well take your shot. At the very least you'll learn a lot. And someone with your talent, as long as you continue to hustle, rarely go hungry in this world. And if you succeed, well then, you might get a book deal in the process.
I once pitched a fairly well-known Bay Area VC in 2015. We were looking to raise a $2.5M Seed round. The VC looked at me through his steepled fingers and said: "This is great. I'm just trying to figure out if you're a $100M business or a $1B business..."
And while it was flattering to be considered either, there was only one business they were going to invest in.
I understand the mechanics involved in some of these funds and the myriad of considerations that go into their investment theses, but it was also sad and frustrating that a lowly "$100M business" (with 4.5M registered users, mind you) couldn't get funded.
Don't hear me bemoaning the fact that we didn't get funded or that we somehow didn't receive our due. I'm just adding my experience with the gap that Neil is citing. And just like in broader societal terms, I think a healthy startup "Middle Class" would make for a healthier overall economy.
Dare I say no one has done more for the blog form than Mr. Kottke. His humble, almost monkish 24-year commitment to not only the pursuit of knowledge and meaning in the world, but his absolute insistence on sharing that pursuit with anyone who wants to ride along in that journey is one of the all-time greatest contributions to the web.
Godspeed, Jason. Be well and see you on the flip (in whatever way you deem fit).
I can’t believe it’s been 24 years. I remember exploring 0sil8 way back when and being inspired by the cool things you could do with html. How time flies.
I wish therapy were more accessible and better regulated. You shouldn't have to still be so upset about a normal early adopter experience 27 years later that you unload on strangers like this.
> I wish therapy were more accessible and better regulated.
Those are incompatible wishes. More regulation automatically leads to higher costs. Enforcing the “right” training and hence ideology also doesn’t help when the only thing that has an effect on therapeutic effectiveness is the extent to which a therapist and client vibe with each other.
Describing someone else's success as messed up while riding the line between venting and emotional dumping. Blogging was seen as a weird nerd thing until the 2000s and got the usual response. I doubt Jason Kottke was spared the same experience. I sure wasn't! But I went a healthier path and took the chain of failures and small wins as learning experiences that have served me well in the years since.
Some people get bitter about failure, and then dump it in places where no one asked without any of the grace and introspection that might turn it from obnoxious to something others can learn from. That's the problem.
That comment is hardly in the top 33% of emotional outbursts I've seen on HN. Are people just defensive about their favorite blogger? That comment was nothing personal about Kottke unless you squint and read it literally.
it's about people pressing their will on me simply because they didn't like what I was doing, with a vague follow-through that humanity is doomed because this is just how we are to each other.
it's how humans treat each other that I was saying is "messed up", because it is messed up. we are doomed.
the number of people that can follow the written word is astonishingly small, these days. I'm not a professional author, I don't have that skill, but I was not hiding my meaning in any way.
many readers just ascribe a personality to an author of a comment depending on their own mood at the time, then color their view of the entire passage as if that was the mood intended by the author, and they don't even realize they've done it.
I don't know what to tell you if you can't see how messed up this is in general, but especially as a completely off-topic response. Who asked? This has nothing to do with the announcement, it has no relevancy to the discussion. It has nothing to do with the topic or the comment you replied to upthread. This is you venting and soapboxing.
Let's go back and remember what that comment was:
>> "Dare I say no one has done more for the blog form than Mr. Kottke. His humble, almost monkish 24-year commitment to not only the pursuit of knowledge and meaning in the world, but his absolute insistence on sharing that pursuit with anyone who wants to ride along in that journey is one of the all-time greatest contributions to the web."
>> "Godspeed, Jason. Be well and see you on the flip (in whatever way you deem fit)."
What does your wordvomit about your trauma re: blogging and the human condition have to do with asellke's kind words? You made everything about you.
>> "it isn't about kottke."
Correct. So why did you post it? Don't answer that. Move on.
I think that's entirely valid and happening before our eyes in this thread. But whenever I think like that, a second thought comes to mind: Why do you see the mote that is in your brother’s eye, but do not notice the beam that is in your own eye? Or how can you say to your brother, ‘Let me take the mote out of your eye,’ when there is a beam in your own eye? I find focusing on myself is a lot more productive and genuine to my frustration - it's usually, really about me.
But everyone who ever built anything good, from Newton to MLK to Norman Borlaug, were also humans and suffered from (and enjoyed) human nature.
This has been downvoted, but as someone who has been blogging for 13 and a half years now, I’m sorry you had to deal with that. You did not deserve that discouragement.
I faced discouragement early on when I wanted to get into blogging—in my first attempt, I faced a guy who was effectively trying to cyberbully me—but I eventually found my way in. I’ve been at it ever since. I encourage you to give it another shot, if you haven’t.
> an absolutely endless parade of people said that it's stupid and that I should stop. I was never popular, I don't know if I was any good, but I caved, and stopped.
That is my experience (in different fields), and it's the experience of many. It was before I understood how innovation and creativity work ('first they laugh at you ...') and also before I learned to know and love myself. Now I face the same responses for some aspects of my life, but there is no doubt anymore about what I should be doing.
But doubt or not, it can be lonely and stressful at times. There is a cost and it's not always worth paying. You have to know yourself to know the value of whatever you are doing, the cost to you, and whether that's worthwhile.
The whole experience was the hardest thing I've ever done.
It was also one of the most fulfilling professional experiences of my life.
I intentionally stepped off the corporate ladder to pursue this dream. But because of my prior commitments/obligations, I wasn't able to drop everything and go all in. That was a hinderance. It made things harder. It put a strain on my family. But it was doable. And even though we didn't achieve our ultimate goal, these complications were not the reason for failure.
I became an independent consultant that gave me an income with some flexibility to allow me to asynchronously lead our startup. I called the time outside of my consulting work "the nightshift". We raised a seed round that allowed my younger and less encumbered co-founders to work as FTEs. We took in more funds that added another six FTEs and an offshore team. Over the 10 years we existed, I never took a salary. When the chips were down and I needed to be 100% dedicated, I emptied my retirement account.
This arrangement was far from ideal, nor do I fully recommend it, but it gave us a shot. We built, tested, and learned our way to a product that served several million (non-paying) customers. We made plenty of mistakes. But we learned from them. We learned to be so frugal, so resilient. So incredibly nimble and innovative. I yearn for that kind of creative power again. It has prepared me to take on anything in life. I've never been to war or faced death with my comrades on a daily basis, but in business terms, I imagine startup life is as close as you can get. The experience has made me a better husband, father, friend, and colleague.
I've since returned to corporate life (for now). There I am invincible. None of it scares me. Corporate politics, bureaucracy, and general bullshit pale by comparison. My startup experience has become my superpower. Because I know I can help raise our game, knowing how to bring out the best in our people and to keep perspective on what is truly "hard" and how to get things done with less and under far less ideal circumstances.
So I say go for it. But go in with your eyes open. The odds are long no matter what. Might as well take your shot. At the very least you'll learn a lot. And someone with your talent, as long as you continue to hustle, rarely go hungry in this world. And if you succeed, well then, you might get a book deal in the process.