I’ve worked at startups from 4 people to 400+ people and invested and advised from incubation to Series D and beyond and it still surprises me how often “how do we hire?” comes up as a topic of discussion. I mean that both in the macro sense (“how do we know if we need to add a new person”) and the micro (“how do we effectively vet people to minimize false positives and false negatives?”).

Lots of web3 projects — web3 games especially — have had splashy launches in the last year, selling millions of dollars of NFTs or pre-selling tokens that will be used as a currency within their game or app. They then trumpet that success to investors and use the momentum to catalyze massive growth fundraises that would normally be reserved for much more established companies. Their central claim is that consumer demand for tokens or NFTs is proof that people want what they’re building — that they have strong product-market fit.

As I’m writing this, the floor price for buying a Bored Ape Yacht Club NFT hovers around 73ETH, or about $185k. That’s pretty wild for a jpg of a cartoon ape that by many accounts isn’t exactly high art. Depending on who you ask, Bored Apes are either a glimpse of the future or a scam, or both. Why are people willing to pay nearly a quarter of a million dollars for a digital picture of a monkey?

Since I’m already in the mode of reflecting on the past year, now’s as good a time as any to start planning for the upcoming one. While I’m going through a more detailed personal reflection and planning process offline (which includes specific goals and milestones so it’s not quite so hand-wavy), I thought the high-level conclusions were worth sharing in case they inspire you!

The new year is a great time to take stock of what worked and what didn’t from the last year of your life. 2021 was year two of COVID, so while we’re not back to how things were pre-COVID, expectations got more predictable and life settled into a new rhythm. Here are the changes I made in 2021 that led to the biggest improvements to my overall health, happiness, and personal fulfillment.

I remember when I was in high school I would get absolutely obsessed with a band. I would buy all their albums (of course, this was back when buying albums was a thing people did), I would go to their shows whenever they were in town, I’d have a t-shirt or two and a sticker on my laptop. I’d scour the internet for live recordings and rarities. I knew the lyrics back to front. I felt like the band’s music spoke to me, that it reflected something real and honest and true about my life. (Which, looking back, isn’t super flattering. Let’s just say I’ve come a long way since then.)

Tesla has the best strategic positioning of any car manufacturer currently operating. It’s easy to underestimate the company on the basis of its relatively small scale in the market: their goal is to produce 80–90k units this year out of a total US market of 17.5M cars sold. Even their 325k Model 3 pre-orders are just a drop in the bucket. But Tesla is several years ahead of all other manufacturers both technologically and operationally, and its competitors are fundamentally unable to respond. If you think about it, the competition has already had 10 years to counter Tesla’s moves, yet they haven’t. What’s going on?

Chief of Staff has been the hottest job in the valley since about 2015. It makes sense to have one if you’re the CEO of a 10,000 person company and you have a 12 person executive staff to oversee, but more and more Seed and Series A stage companies are hiring Chiefs of Staff. If you’re at this stage and are considering hiring a Chief of Staff: don’t. 9 times out of 10, it’s the wrong answer.