The (Focused) Chaos that was 2023
A look back on the newsletter's first year of existence (#55)
On December 13, 2022 I published my first newsletter post. I had been thinking about getting back into writing for awhile and took the plunge. No real plan or strategy. I published every week (minus last week when I was really sick!) and today is issue #55.
For many, including myself, 2023 was a crazy year. Tough. Many downs, some ups. Lots of lessons learned. Some described it as a “startup reckoning.” Others, “a correction.” It’s a bit of both.
I’ve been through multiple cycles that felt catastrophic: the dot com bust; September 11th; the 2008 housing crisis and today, where the world seems to be teetering on economic and political collapse. I don’t know what the future holds, but I do know this: great startups will be created in 2024. And 2025. And 2026. And 2027. Etc. How do I know? Because great companies are created every year. That gives me hope.
I will forever be in awe of and grateful for people who decide to start companies. Through them, we have a chance to solve some of the world’s most daunting problems and improve people’s lives.
And me? Well, I write…or at least try to.
When I launched Focused Chaos I wasn’t completely sure what to cover. Startups? Sure. Entrepreneurship? Ya. Product management? Why not. But I know that newsletters need focus and a clarity of purpose in order to really take off. I haven’t quite found that clarity, and I’m OK with that. I enjoy talking about, discussing and sharing too many things, with perhaps a single thread going through everything that says, “This is what I’m most interested in right now, and if I can help others who are similarly focused, wonderful.”
Case in point: My first post on venture studios was ~6 months into the newsletter: The Many Flavors of Venture Studios. I didn’t know how people would react, because I hadn’t done anything in-depth on studios before. It’s my most popular post!
Many newsletters do roundups at the end of the year. Given the diversity of topics that I cover (which honestly will continue in 2024), I thought it would be a fun exercise to do the same.
Venture Studios
If you don’t know already, I run a venture studio, Highline Beta. As the popularity of studios explodes, it makes sense for me to share my experiences.
Product Management
I love building products. I still get a jolt of excitement crafting the right requirements, scoping work out with colleagues, testing features before a release and then putting new stuff into users’/customers’ hands. It doesn’t get old.
The Problem with Product Management (to be honest I thought this would do better or stir the pot more)
There’s Nothing Wrong with MVPs (I really thought this would cause an uproar; alas, I’m not a big enough deal to cause uproars!)
How Do You Decide to Build a Feature to Close a Deal? (this hit a nerve, where many people agreed with me and feel this pain regularly, which I guess is a good reminder—write about the problems people are facing)
Interestingly, my post on pivoting (How to Pivot the Right Way) shit the bed. Not sure why.
Building Startups & Entrepreneurship
This is a broader bucket, but has a few of my most popular and in-depth posts.
The Startup CEO Job is Intense, Lonely, Rewarding & Crazy (I ran a survey with startup CEOs to help craft this post and enjoyed the process a lot; I’ll be doing similar survey posts in the future)
Do You Have an Unfair Advantage? (generated a surprising number of subscriptions, which I consider a good sign)
Building a Bottom Up Business Model for Your Startup (comes with business model templates you can use)
Takeaways from Writing Focused Chaos for 1 Year
I continue to experiment & learn, and want to share some of those lessons here:
Practical break downs with tactical how-to information works. The key is using examples and providing lots of detail. The “Breaking Down an Early Stage Startup Pitch Deck” post used a pitch deck we put together at Highline Beta, and I went through it slide by slide. It’s one of my most popular posts.
Honest emotions resonate. Every post doesn’t have to be a “how to guide”—in fact, people enjoy transparent, honest sharing of feelings too. One of my most popular posts is about regret, “One of My Biggest Regrets: Wasting Years of My Life”. A lot of people emailed me and thanked me for writing this so openly.
The echo chamber is real. Pushing controversial topics in an attempt to create buzz / virality is tough; the people reading your content are already believers, so they tend to agree with your position. Those are the people that like and share your content, not the people who think you’re an idiot (they just unsubscribe). Echo chambers might be safe spaces, but they create unnecessary divides, and suddenly everyone’s voice you hear is the same as yours, which isn’t great. You lose diversity of thought, which means very few new ideas emerge.
People will always unsubscribe. Every time I publish a post, people unsubscribe. It bothered me at first, but I try to ignore it now. I’m certain people will unsubscribe after receiving this post! I also know that I cover a broad range of topics, so people may subscribe to get more venture studio specific content, but I might not have anything to say on that front for a couple months. In the meantime, they may unsubscribe.
Coming up with a weekly topic is hard. Every week I want to put something valuable out there, but it takes a lot of work. You don’t want to say the same thing countless others have already said. You don’t want to talk out your ass about things you haven’t lived. Examples and case studies are powerful. One approach is to mix things up with different types of content that don’t take as much work. Interviews are a good example. Personally, I’m a fan, although I know some people don’t like reading them. I’ve done two so far (see here and here), both of which I thought were great—I learned a ton. In 2024 I’ll be experimenting with different content styles: interviews, survey analyses, summary posts, etc. We’ll see how it goes!
Do it for the network. IMO this is the key unlock for Focused Chaos, meeting new people and staying connected to my network. The newsletter gives me a way of reaching people and staying top of mind. That’ll have significant, lasting benefits (and has already created a bunch of value for me, Highline Beta and our portfolio). Simply put, if you give, you get.
On that note, I wanted to highlight the Helpful Resources section of the newsletter. This is where I link to all the tools/resources I’ve built. There are currently 11 resources including: a fundraising playbook, venture studio checklist, PRD template, equity dilution model, assumption tracker and more.
Thank you to everyone that reads Focused Chaos. 🙏 💪
My big ask in 2024: Send me questions and feedback.
What would you like me to write about? Where could I add more details or context into topics I’ve covered?
Happy Holidays! 🎉
(I’ll be back the week of Jan 8th, 2024.)
In a sea of content hurtling at me every minute, along with my focus being constantly torn in many directions while running my business, I find your newsletter relatable, helpful, and worth reading. Looking forward to 2024!
"I will forever be in awe of and grateful for people who decide to start companies." 🙏🏽
It takes great supporters and wizards of knowledge to help steer the ship. Thanks for a great year of insightful reads.