robfitz

An extremely eye-opening comment, thank you. I haven't played with the image generators for ages, and hadn't realized where the workflows had gotten to.

Very interesting to see differences between the "mature" AI coding workflow vs. the "mature" image workflow. Context and design docs vs. pipelines and modules...

I've also got a toe inside the publishing industry (which is ridicilously, hilariously tech-impaired), and this has certainly gotten me noodling over what the workflow there ought to be...

It's all about that value-per-word ;)

There are plenty of river ports/quays with power and water hookups. If you want to houseboat it, you really only need to move when you want to dump the septic tank (and in some areas, not even that).

The "good" spots are highly desirable and usually privately owned (or on a very long-term lease), and you often need to buy a boat to get the mooring spot beneath it. (A buddy of mine in London ended up with 3 boats while upgrading his mooring spot.)

Another options is to vagabond it, where you move your boat to a new area every week or two -- this is usually unserviced, so it's more like camping, but lets you use unofficial spots and is free.

(The last option is to find goofy loopholes. E.g., in some areas of the Thames, you can create a nesting habitat for an endangered bird on your boat, and then once the bird settles in, they can't force you to move, since doing so would destroy an important habitat. Sounds stupid but a surprising number of permanent city boats are there on some sort of loophole.)

I do ~$15k/m in royalties from 3 nonfiction titles[1] which mostly sell via word of mouth (as opposed to hands-on marketing and/or author platform stuff). So it's definitely possible, if you approach it properly.

It's true, as another commenter mentioned, that the expected result of most nonfiction is zero. But in my opinion, that's largely because most nonfiction today is built like software in built like software in the 90s, without proper user-facing iteration and refinement. I wrote a whole thing about it[2].

Books created as a cynical cash-grab are already negative value in terms of time investment and opportunity cost. I think they're only worth getting into if you care enough about it (either the end result or the activity) to do it regardless of the money. And then, only once that's true, perhaps start looking for ways to optimize it as a process and product.

[1] https://www.amazon.com/stores/author/B00J77JH5G/allbooks [2] https://helpthisbook.com/robfitz/useful/

Any chance you've written more about the system design and incentives side of it somewhere (whether about medium in particular, a previous biz, or just the mechanisms in general)? If so, I'd absolutely love to dig in... It's got big overlap w/ some stuff I'm trying to figure out for building useful communities, and it's not so common to find folks with a deep view on it ;)

I got into the fifth batch (s07) and remember my other startup friends staging an intervention to dissuade me from accepting because "the valuation is really bad."

Interesting to see how long even the industry insiders failed to take YC seriously. And then once it was working, they flipped immediately to complaining that YC was too powerful and too influential (unbeatable network effect, seed/A valuation inflation, and so on).

I also remember the constant naysaying about scalability and batch size. Our batch was ~19 companies. People kept naysaying, "Well this model is fine for now, but it will never work past 20 teams."

PG would always reply with something like, "Yeah, they said that when we had fewer than 10 teams also. We aren't thinking too far ahead; each batch, we just find the next bottleneck and solve it, and we'll see how far that gets us." Which evidently got them pretty far. A lovely example of doing things that don't scale.

Aw, you're a star, Andrew. I really appreciate (and admire) the sentiment and thoughtfulness. (Although I still think that I dropped a bit of an unsalvageable mess on your lap!)

As a side note since you're here, I'm super psyched that you've taken the time to share what you've learned in your new book -- it's the next one up on my list for serious study, and I couldn't be more excited about it. Based on the reviews so far, it looks like you've written something really special and that I'm in for a real treat. Can't wait :)

The mundane answer is that there's some stuff that I worry about optimizing and other stuff that I don't, and this little personal site is the latter ;).

To a lesser extent, I also didn't exactly expect this to hit frontpage, so I'd sort of assumed that the only people who would see it were people who already knew me.

I'm still not sure about the answer to that, but this has at least prompted me to give it a proper think and decide whether I want to try to appeal to "the world" or just stay focused on my own little orbit. No idea where I'll end up, but it's an interesting question, and I appreciate you giving me the nudge to take it seriously.

Exactly. Really opens up some beautiful coastal areas to explore where the tides are big.

It's also quite nice to know that if you happen to run into an unmarked sandbank, you'll only have to sit there, and not sit there sideways ;)

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.)

The user is always right ;). I'll keep working on it. Thanks again.

I don't have a proper answer (because it's a good and difficult question), but I sort of think of it as a context-dependant thing.

E.g., During a customer interview where I'm trying to understand what they've done (and predict what they'll do), I have vanishingly low confidence in their self-predicted behavior. So I prefer to try to look at what they've actually done in the past, talk to them to understand why they did it that way instead of some other way, tease out the invisible data (like what they tried or researched but didn't continue with), and then come to my own conclusion about how that's all likely to extrapolate.

But in terms of understanding and ascribing purpose to my experiences? Or understanding and empathizing with a friend or stranger? Or sending a message out into the world in a way that can stick and spread? In that case, it's kind of a subjective thing to start with, and it's all about the stories. (To clarify: not intentionally fanciful or fictional stories. Just "stories" in the sense of how we tie all these things that happen into something coherent and ordered.)

That was kind of a non-answer, and I'm sorry I can't be more helpful. I only understand a very, very small number of things. (Three, I think, although I'm working hard on understanding the fourth.) Apart from those few narrow domains, I'm just fumbling through it like everybody else.

An important moment and transformation, well-described. Thanks for sharing it :)

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 :)

It's far less dramatic than you'd hope.

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.

Westerley Centaur 1972 bilge keel, 7.9 meters, with interior layout A: https://sailboatdata.com/sailboat/centaur-26-westerly

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?)

And I want you to get one ;)

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.

Hey mate, congrats!

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.

It's a positive thing, just written weirdly.

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.

I had been wondering why/how so many startups had suddenly "figured out" the transcript-first editing interface, and it seems that Gentle was the answer.

Such a transformational piece of invention that has enabled a whole wave of powerful and valuable products (e.g., descript.com for video/audio editing, buildbetter.app and grain.co for custdev/PM interviews, callin.com for podcasts, etc.).

Amazing and impactful work here, and it's striking how non-commercially the creator approached it all. Thanks for sharing.

Haha oh man, when did I even publicly mention that?

I doubt I'll ever release it as a book (since it needs a full rewrite and my enthusiasm for it was very tied to that moment in my life), but maybe a couple of the ideas will slip out eventually.

A few of the ideas, yes, but not the whole thing. But you could probably get those ideas just as easily from the linked summary.

In particular, stuff like digging beneath requirements & feature requests to understand the root cause and their current behavior. And probably also the general idea of opening up a safe space for open learning at the beginning of each conversation (which is also a common idea in other sales approaches like SPIN Selling).

Also, it would be more useful while scoping out a new product/market, and less useful for products that are already mature/defined.

So my guess is that you'd get a couple useful ideas, but not a book's worth.

If the problem is well-defined, you can get a fairly strong signal on intent-to-purchase by asking for commitments (i.e., time, reputation, money, or secrets about an enterprise buying process). You start with the smallest ones (weakest signal but easiest to ask for early) and then move up toward money (and eventually full price) as you make progress with the overall business.

But if the problem is undefined/unknown (like much future tech), or if the product is a nice-to-have or "10x improvement" (like many B2C apps or UX improvements), then you basically have to validate via a prototype (or some other sort of creative v1).

(You can still do your discovery/understanding via conversation in either case, of course.)

I think it depends very much on your goals. For me, after going through YC with my first company and having a difficult four years chasing scale, I realized that I was oriented more toward lifestyle/reliability/freedom, and I've been fairly focused on that for the last 10 years (although it really only took a couple years to achieve once I was clear on my goals, and has been pretty relaxed since then).

So with that caveat out of the way, my top-of-mind career advice for entrepreneurial introverts is:

1 // Learning how to talk to (and listen to) people is probably the highest-leverage career skill you'll ever learn, even if you only go from "terrible" to "functional." There's a tremendous amount of discomfort while learning it, but that discomfort is temporary. I'll never "like" talking to strangers, and I'll always need to manage my energy levels, context, and recovery time. That being said, the ability to do so when useful to my career (like custdev or sales or fundraising) or life (like making friends in a new city or negotiating with an angry plumber) has been transformational. The pain is temporary and the benefit is profound.

2 // Journal each morning. Braindump your frustrations/goals/fears onto paper. Your brain likely works differently from most "successful" people, which means that the common advice won't fully resonate with you, and you'll need to chart more of your own path. This requires thinking, and for a lot of introverts, writing is the clearest way to think (but if you're different, use what works for you). Similarly, run every piece of advice you hear (well, the compelling bits anyway) through a personality filter, normalize it for personality/context, and then decide whether it's likely to be right you. Common example: "Go to that conference and meet some customers!" Maybe that works for other people, but it has a 0% chance of working for me. But there's a valuable core concept to that advice (go engage with new customers) that can perhaps be adjusted to a context I'm comfortable in.

3 // Cultivate relationships with strong potential cofounders long before you need them. You'll never be as quick on the draw in conversation as others, so you need the important relationships built ahead of time. For potential cofounders (the most important network available), the way to do that is by collaborating on small, time-constrained side projects. Allows both parties to evaluate what each other bring to table outside of an "urgent" situation, and without relying on quick talking.

4 // Don't let anyone press you into "right now" negotiations or decisions. Use live conversations to gather data, and then use your time alone to process it and come to a decision about next steps. Repeat if necessary. Nobody will give you this time by default, but nobody will deny it to you once you ask (and if they do, you probably shouldn't work with them anyway).

There's probably more, that's just top of mind, but it's what feels important to my brain right now.

I always love summaries that are publicly posted (like this one, no matter how detailed), and I only dislike the (relatively rare) ones that are repackaged as "new" books on Amazon and then resold at a profit (it feels bad in general, but especially since I already work pretty hard to make my books as short as possible).

My feeling has always been that if a book can be sufficiently summarized in a blog post, then it should be a blog post ;). And if someone reads the summary and fully "gets it," they probably would have been frustrated by the full book, since they probably already had a lot of the foundational knowledge in place. So it's better if they don't buy it in the first place. And different people will read the summary, want the extra detail, and grab the full book, which is great too.

Even with piracy of the full book (which is currently #1 on google for various fairly guessable searches), I still feel that it ends up coming back to me via word of mouth. Piracy probably hurts "bad" books that are propped up by PR, but it definitely helps books that people find useful, since they end up recommending it to other folks who may pay.