The Quest to Be Good at Everything

Henrik Werdelin seems like he has it all figured out.

He’s a co-founder of Bark, a business with over 650,000 subscribers and hundreds of happy employees. He runs prehype, a venture development firm that has helped start businesses like Roman ($176mm raised) and Managed By Q (acquired by WeWork.) He runs a podcast. He teaches entrepreneurship to university students. And he’s a husband and father to a young son.

With a list of commitments like that, it’s pretty easy to wonder: how the hell does he do it all?

And that’s something I’ve personally been wondering for a while as I’ve gotten to see him work up close: prehype‚ the firm he’s built as a home for second-time entrepreneurs, has become a home for me too — and the place I get to explore weird side-projects (like this one!) without pressure or a timeline.

I’ve always been amazed at how much he gets done in a day, so getting to spend time unpacking his system was eye-opening. Here’s what we talk about in this interview:

• How his 8 + 1 system allows him to manage running two companies, teaching, running a podcast, and spending time with his family
• How he hacked his Google Home to help him record those little thoughts that hit right as he’s going to sleep
• How he met his wife and life partner
• How thinks he about creating a purposeful and highly conscious life
• How he uses experimentation to constantly improve himself
• How he uses Trello and paper notebooks to keep himself organized

Let’s dive in!

Tell us about who you are

I build things with people I like in interesting spaces. I have built a number of businesses as a co-founder, and I also run a network of entrepreneurs called prehype where we build new businesses and teach entrepreneurial skills.

I keep myself organized and productive with what I call the 8 + 1 system. It’s composed of eight categories that are important to me in my life that I try to pay purposeful attention to. The categories are:

• Transact
• Invest
• Assist
• Learn
• Health
• Family
• Relationships
• Ego / Self-Kindness

The idea is to think of each category as a box, and different activities in my life fit into one or more boxes. I want to make sure each box is as close to filled at all times as possible. 

Why he developed this system for himself

I do this for a few reasons. Because I’m running two companies, I teach, I have a number of active angel investments, and I have a family, I have a lot of demands on my time. So I’m always nervous I’m missing something. Having a system like this helps me make sure that I’m always on top of my commitments.

It helps me figure out what to do, and also what not to do. And figuring out what not to do, I find, is just as important as the opposite. 

Because for me, I’m interested in and excited by lots of different things — so this gives me a chance to sit down and reflect on whether or not they’re a good idea. If something doesn’t fit into these boxes, it doesn’t fit into my life.

So it allows me to be purposeful and conscious about how I’m spending my time. I think a lot of times we do things because we’re conditioned to do them, rather than because we’ve chosen to do them. So having a system like this allows me to be conscious about breaking out of that conditioning and spend my time wisely.

Another really important part of this is that it allows me to try new ways to improve my life. I think a lot about using experimentation to maximize the return on my effort. Having this system allows me to make sure that I’m constantly experimenting and trying new things in each of these boxes to improve my performance.

On trying to be excellent in every area of his life, rather than just one area

Finally, the 8 + 1 system codifies something a little bit contrarian about me which is that rather than aspiring to be good at one particular area of my life, I aspire to be as good at all areas of my life as I can be.

Being good at all of these areas represents for me, what I think is the best version of myself.

To be clear, that’s not necessarily right or wrong. I think a lot of people want to be good at just one thing, which I think is great. They’ll probably be better at that one thing than I am at it. Neither option is necessarily better. 

It’s just the one that I happen to subscribe to.

So let’s talk about each of the boxes and how they work together to help me live my life.

Box 1: Transact

The first box in the 8 + 1 system is Transact, and it’s about making money. 

Transact is just making sure that you have a job, or advisory gigs, or something that’s bringing in a direct revenue stream to support your life. 

This may seem obvious, but I think for me, particularly in startups, there’s a focus on doing things that don’t necessarily have any immediate-term payoff. So it’s worthwhile for me to make sure that I’m bringing in enough money to support my family and myself.

Box 2: Invest

The second box is Invest, and it’s really about doing things where my input today compounds over time.

Right now, Invest is pretty straightforward because I do seed investing. But it can also be broader than just investing money. For example, I spend a lot of time thinking about how to invest in building a reputation in a particular area so that I’m seen as an expert. 

Or, at the earliest stages of a company, you may invest your time for free with the idea that that input leads to greater output as the company matures.

The idea is that as I pour input into Invest over time — either in terms of money or time or effort — eventually the results of that input will compound over time until I’m able to move whatever it is into the Transact bucket and reap some of the monetary rewards.

Box 3: Assist

The third box is Assist, and it’s about helping people. It’s something I do anyway, but I want to become better at it. Having it as a bucket makes sure that I’m purposeful about doing more assisting, and getting better at it. 

Assist can be anything from writing a book to providing feedback to founders who are just starting out. 

Box 4: Learn

The fourth box is Learn. This box is about being very self-aware of what my output is, and then figuring out what I need to learn to become better at providing that output. 

For example, one of my outputs both at Bark and prehype is knowing how new technology is going to affect our business. Once it became clear that AI and machine learning were going to significantly change the business landscape over the next 10 years, I hired a tutor to help me learn about machine learning from the ground up. 

So over a few months I learned about the most popular machine learning techniques, and even built a few prototypes myself to try to understand things as deeply as possible.