Heya, thanks, it's a new site setup, so it's super helpful to hear about your experience with it -- I'll get that clarified. (I had nestled an about/bio link in the deep bottom-left sidenav, but it's admittedly very easy to overlook.) In the meantime, if you're still curious, the full bio thing is at: http://stuff.robfitz.com/about/
It was the difference between a wikipedia article vs. a biography (i.e., a collection of facts vs. those same facts, but arranged around a narrative).
A specific example came up while trying to explain my first company's pivots through three products (trying to figure out a social/UGC ad stack before Facebook did). If you looked at the business model, our value prop, customer segment, etc. all of that stayed the same. Which was the unifying thread, and which I can now articulate at least semi-coherently.
But when I was describing it to Andrew, it came out as three completely unrelated products, and that we were just wildly changing plans without any coherent vision or direction. I remember that moment due to his look of profound confusion, where he was really trying to figure out how these three things I had just described were related.
I tried a bit of everything, and I did it all at the same time, so it's hard to pin down causation. The only thing that had to happen was to shift my diet away from being primarily composed of alcohol, coffee, and tabasco. Apart from that, a high-end probiotic thing may well have helped, and a good chiro/nutritionist acted as a sort of accountability coach to keep me going.
Also, getting serious about reining in the drinking acted as an anchor habit that led to a bunch of other positive lifestyle changes. (I still probably drink far more than almost anyone would consider acceptable, but it's down to a level where my body appears able to keep up. So still a work in progress, I guess, but at least my energy is back up.)
This is semi off-topic, but I normally write books, which I work pretty hard to edit down into the shortest versions of themselves.
As a weird side-effect of that, I noticed myself starting to hold all of my writing to that same standard, which was stopping me from putting out anything more off-the-cuff.
So part of my motivation with this site (which is only about a week old) was to frame it in a way, at least for myself, where I felt comfortable sharing the stuff-in-progress without worrying too much that it wasn't a finished book.
Which I guess is a long way to say that the rambliness is an intentional decision, since otherwise it wouldn't be doing the job (for me) that it was designed for. I already spend 20+ hours a week doing fairly utilitarian writing for my books, so this little site needs to be something different if I hope to stick with it. And in an ideal world, maybe a few other people will happen to enjoy some bits and pieces along the way :)
I left it moored up at a port along the canal for winter (when the canal gets too shallow to traverse), the folks who were supposed to be keeping an eye on it didn't, uncharacteristic winter storms were blowing rain and muck all over the place, the cockpit drains got clogged, the cockpit filled with water, and things went downhill from there ;)
It was sitting quite happily on the shallow riverbed when I returned, but the inside was a swamp, and I had to tear out and trash the whole interior. At least it was fresh water, so the engine (mostly) survived.
Was the most popular British-made small boat of all time, and some of them have successfully circumnavigated.
Sturdy thing with only 0.9m draft, able to ride into shallow waters and sit happily on its keels when the tide goes out, and surprisingly spacious for its length. Good boat.
Ya, we went in cold after just a quick email exchange, so you're spot on there.
Still, I remember being quite struck by how authentically he was working to get to the heart of it and tease out some value from the mess I was making. It really felt like he was on my side, working with me, despite how difficult I was making it.
I grabbed a copy of his book a couple days back (which is maybe what reminded me of this little anecdote) but haven't gotten into it yet since the pile of interesting reading is just a bit too deep. Very much looking forward to it though, cuz nobody knows it better (except maybe Oprah, I guess?)
Sailing had always been on my "someday bucket list," but I kept putting it off since I could never make the time to take the week or two off to do the course.
But once I started learning, it was so much more deeply satisfying than anything else in my life, that it immediately became a top focus. Before I'd even finished my captain's license, I had already hit "buy it now" on an ebay listing (admittedly reckless and not recommended, but I couldn't wait).
That being said, boats are floating money pits (the rule of thumb is that you spend half the boat's price again, every year, in maintenance and mooring) and take a ton of upkeep, so I think it's only viable if it's a major piece of your life and you're willing to devote considerable time o it. Otherwise, it just sits there, losing money while accumulating chores.
I sold mine during the first lockdown, but I'll absolutely get another someday, once I'm ready to wrap my life around it again.
Yeah, I looked at trailer sailers (although I wanted a cabin), but it wasn't really viable for the types of travel I wanted to do. Now that my life and location are slightly more predictable, a 7m with a small cabin that could go on a trailer would be ideal. (Although I'm sure I won't end up making that sensible choice.)
I hit financial independence in my early 30s (not flashy rich, but sufficient to never work again) and am now 37.
Here's my take:
People get directionless and depressed after winning the lottery. It's a common thing, and you can read a ton of sad stories about it. Also from hitting it big in professional sports, business, whatever. I say that to reassure you that (1) it's not you, it's human nature, (2) you aren't doing anything wrong, and (3) you aren't alone.
Essentially, what has happened (if you'll forgive me for generalizing and guessing) is that you're suddenly suffering *a vacuum of purpose.*
You used to get your purpose from your studies/struggles/work, and now those things have had the legs kicked out from under them.
So on the one hand: fuck! That's a lot of change.
But on the other hand, this was going to happen eventually anyway. Eventually, you were going to retire, or get fired, or get injured, and end up with a lot of time on your hands and the inability to follow the prescribed path. People get bummed out in retirement, too, for the same reason.
So now, what you've got is an opportunity to bring the learning forward: to figure out how you want to live while you've still got maximum optionality.
That's a terrible responsibility and a tremendous luxury.
But it's in no way easy.
The hardest part about your current situation will be the lack of understanding from everyone around you, because they only see the upside. But the downside -- and it's real as hell and hard as hell -- is that you now need to figure out how you want to live, completely unconstrained.
That's a life's work. But it's also a life's meaning. So try stuff.
When I first got free, I learned to sail, bought an old boat, spent 6 months in a boatyard working 10 hour days of manual labor to repair it, and then spent 3 years sailing around the coasts and canals of England, France, and Spain. I thought that was what I wanted. It's what I had always imagined doing if I didn't need to work.
And you know what I learned? That I enjoy working on interesting projects with smart people. And that I enjoy being able to have friends over for dinner parties and board games. So in the years since then, I've been gradually trading off pieces of my freedom for other things that I find more rewarding.
Learning how to live a life is an experimental, experiential, exploratory process. I wish you well with it, though. It's not easy. It's not supposed to be. But it's very, very meanignful.
It's less about deciding how you want to live, and more about discovering how you want to live.
In terms of mundane tips, try to keep the expenses in check for at least a couple years while you give yourself time to explore it. Don't throw yourself into the icy waters of complete overnight lifestyle change. Take your time; the money will still be there. Maybe you'll find new meaning in the journey, and maybe you'll find a new passion in the process. We all need something to be excited about, but sometimes we need to go find it.
E.g., an early employee takes a moderate salary plus X% equity.
Normally that person is stuck waiting until a liquidity event (like an acquisition, IPO, or late-round funding where some private shares can be sold).
But if the startup has shifted from hypergrowth mode to realizing that it's going to be profitable and stable, then that liquidity event won't ever happen.
So Tiny is basically saying, hey, if you've incentivized your people with equity, but you're no longer on the VC exit path, you can set up a deal with us where those people may choose to sell us their little slices of equity, which gives us some ownership and gives them the financial windfall they were originally hoping for.
