Welcome to Focused Chaos

(#1) Blogging is so 2006...oh wait, never mind. :)

Dec 13, 2022

ChatGPT be damned.

I’m kidding. ChatGPT is very cool. And I’d be lying if I told you that I haven’t been testing it out quite extensively. But I love writing. And I appreciate great writing. Please note: Those last two statements are mutually exclusive, and I cannot guarantee great writing here, at least not on a consistent basis. But I’ll certainly try.

I started blogging in 2006. I wrote about all kinds of things. The topics evolved as I got into new things, whether it was starting a company, raising capital from angels & VCs, launching an early stage accelerator, angel investing, product management, analytics and more. In the “good old days” I would try and get my posts on digg and watch the traffic surge. It was exhilarating. I joined Twitter in March 2007 and leveraged that to build a decently-sized network (at the time) and “go viral.” Again, crazy fun.

In 2013 I co-wrote the book Lean Analytics with Alistair Croll. It took us ~1 year to write. It was an awesome experience. And then…people bought the book! Alistair and I traveled around doing workshops and consulting gigs, but we never had a real plan for how to turn Lean Analytics into a scalable platform. We didn’t build a community. We didn’t launch paid video learning tutorials or anything else. For years we talked about writing a 2nd edition, but we moved on to other things. Never say never—but writing a book is crazy tough (and remember: ChatGPT didn’t exist, and there were no ghost writers involved.)

(btw, Alistair is a legit genius. You should follow him on Twitter and check out his latest book, Just Evil Enough.)

From lots of content publishing to…

Over the years, blogging and publishing content fell to the wayside. A large reason for that was the founding of my current company, Highline Beta. I started the company with Marcus Daniels in 2016. If you’ve ever started a company you know it’s all-consuming. And Highline Beta has been exactly that. Sometimes when a founder suddenly starts posting a lot on social media, or publishing content (just like this) you wonder to yourself, “Is their company toast? Is this person setting themselves up to figure out what’s next by getting ‘back out there’?” I’ve seen that pattern quite a few times, but in my case that’s not what’s happening. I am trying to re-engage (and then grow) a network that might have faded over time, but that’s not because I’m moving away from Highline Beta. Quite the opposite. This very well may be the last company I ever start.

So now what?

Now, I want to write again. Over the last 6+ years I’ve learned a lot building Highline Beta, a venture studio and venture capital fund. It’s been a very interesting experience, and has given me a perspective from “both sides of the table” as a founder and funder. Not only am I an active startup founder (because I consider Highline Beta a startup), but I’m also an investor (because we invest $$.) And, interestingly, in the venture studio model, you get to participate as a “pseudo co-founder” over and over again. It’s an incredible experience to be there for the creation of multiple startups, sleeves rolled up, ready to create as much value as you can.

As much as things have changed since 2006, some things remain largely the same. For example, most of my blog posts that went viral had catchy headlines, often starting with, “X Ways to…” They also had good images that captured people’s attention. So in that vein, here’s a picture of my dog and cat (yes, I’m shamelessly using cute animals for attention) and 5 reasons to subscribe:

5 reasons why you should subscribe to Focused Chaos

Focused Chaos is a newsletter that will provide actionable advice and insights to founders, startups and investors from my perspective as someone that’s living all of these lives at the same time. Here are the 5 reasons you should subscribe:

You’re an early-stage founder looking for help: Everyone needs help some of the time. I’ll be sharing content about how to raise capital, how to manage your investors and board, how to validate your ideas/assumptions/hypotheses, how to build your initial MVP, get traction and measure progress. There’ll probably be a few more topics in there as well, with the goal of helping early stage founders figure things out. I should point out—this includes people that want to start a company but haven’t yet. That first jump off the cliff is damn scary; if I can help ease that fear a bit, I’ll consider that a win.
You’re curious about the venture studio model: Venture studios are having a bit of a moment. Some think that the explosion of venture studios is a “sign of the top” (i.e. the momentum around startup valuations, the free-flowing funding going into startups, etc.) I can definitely appreciate that point of view. As is the case in all professions, there are good ones and bad ones. We saw similar things happen with accelerators; but I know for certain that there are accelerators that create immense value (and again, some that do not.) After over 6 years of building a venture studio, I’ve got plenty of scars and opinions to share.
You’re an investor: It’s not my place to tell investors how to invest, but I do want to work more closely with more investors, both to fund great pre-seed & seed stage startups, and share knowledge. Investing (particularly venture capital) is still such an opaque business. In 2007-2008, I was raising capital for my startup, Standout Jobs. And a VC at the time said to me, “You think raising for a startup is hard? You should try raising for a fund.” At the time I thought that was a pretty crappy thing to say—after all I was pitching every VC I could find desperately trying to fundraise. It certainly didn’t feel easy. But now that I’ve also raised a fund, I can appreciate that VC’s experience. It’s not easy to genuinely understand life “on the other side of the table.” Until you’ve really walked in someone else’s shoes, you can’t really appreciate what they’ve gone through.
You’re a startup employee looking for help: I’m a founder and investor, but I’ve also worked at a few startups and want to share that experience as well. Early-stage startup employees have some of the toughest jobs out there; they take a lot of the risk, but don’t have the same upside as founders. They join startups that have a ton left to validate and figure out, which can be exhilarating and fun, but also scary as hell. Most of my experience is in building software products, which is where I’ll focus, but I’m sure I’ll branch out into other topics as well.
I know Lenny Rachitsky. OK, shameless celebrity plug now. Lenny and I go way back. He now produces the best content on the planet for startups (early and later stage.) But twelve years ago (almost to the day), I picked Lenny up at the Pierre-Elliott Trudeau Airport in Montreal when he joined a super early stage accelerator, Year One Labs, that I co-founded with Alistair Croll, Raymond Luk and Ian Rae. I helped Lenny buy a winter jacket (he was moving from San Diego!) and find an apartment. It was the definition of “value add investor.” Lenny co-founded Localmind, which was then acquired by Airbnb. The story is much longer than that, with plenty of ups and downs, but I learned a ton from Lenny and enjoyed working with him immensely. And his content has honestly inspired me to get back into writing, sharing and helping as many people as I can. (btw, if you’re not familiar with Lenny’s Newsletter, go sign-up now.)

You know the old saying…

Reid Hoffman (apparently) once said something like, “If you’re not embarrassed by the first version of your product, you released too late.” I’m not embarrassed (I haven’t released anything here!) but I am nervous. Putting yourself out there is scary. Imposter syndrome is real. I don’t know if many people will follow along, learn & benefit from this newsletter, and contribute to growing a community around founders & funders, but if we don’t try, we don’t get to find out. In our Highline Beta Slack we have an emoji (:fuckitshipit), and here it is:

And there you go. Welcome to Focused Chaos. I hope you enjoy it.