The leaps you take again and again (Ricky Weekly #65)

This is where I share 3 things every week with my friends and anyone else interested.

A picture from my life:

I saw this magazine at a co-working space and thought it was funny. The name of the magazine is not actually called HENRY (It’s a SF design magazine introducing the design of an luxury apartment at 1 Henry Adams), but that’d be funny because HENRY is a term marketers use for “High Earner Not Rich Yet.”

A thing on my mind:

I’ve skipped a few weeks of Ricky Weekly because things have gotten too busy at Flow Club, which is a good thing. Harj Taggar once said something like, “doing a startup is about prioritizing which fires to put out, which ones to let burn, and if there aren’t any fires, it means you’re not moving fast enough.” As a veteran team, we know the level we need to perform at, and we’re confident in our abilities. There are still times though when something triggers my insecurity and makes me want to crawl up into a ball. The faster we move, the higher the bar, the more often that happens. That’s not bad. It wouldn’t be fun and worthwhile if we don’t keep raising the bar and setting unreasonable goals that trigger self-doubt. I want the growing pains.

I’ve been thinking about two graphs lately to describe some of the feelings I have as a founder. First one is what I’ve talked about before on what it takes to make the leap into a startup, and why it’s easier in some cultures like Silicon Valley. I also mentioned before that while most people talk about the initial leap, the more interesting thing to me is the series of leaps that you keep having to take over and over after the first one. Here’s a graph of what that kind of feels like. You can go days when you don’t feel like you are equipped to handle the challenge, but then there are days when you do and you act with resolve. The thing with a high-growth startup is that the average confidence level is probably somewhere right below the leap line because you have to keep raising your bar, and constantly take leaps out of your comfort zone to think that you can do it.

That reminds me of a graph Paul Graham once drew at the Y Combinator office called The Process that describes the hero’s journey of a typical startup. It’s famous for how well it captures startups. I’d love one that captures what goes on in the founders’ heads during the various stages of this journey.

The other graph I’ve been thinking of is my anxiety level. Over the years I’ve become a more anxious person, which I’m not so enthused about. One thing with anxiety though is that it just simmers and creates discomfort, and rarely do you feel an “attack” to get you to do something about it. It’s kind of insidious and hard to pay attention to.

I read a really good series of blog posts by Adam Goldstein on the topic of founder anxiety, so I will recommend that in the next section.

A piece of content I recommend:

The Anxiety Algorithm - Adam Goldstein

This is first of a three-part blog post that I highly recommend reading all the way through written beautifully by my friend Adam. Adam describes anxiety as “your mind’s immune system,” and that it works very similarly to your body’s actual immune system. According to him, the reason why I’ve gotten more anxious as I’ve gotten older is because when I was younger, possible future threats to me, my company, etc. were not on my radar. Here are some visuals he made to describe anxiety. If you like it, go read it.


As always, you can find out what I’m thinking in more real-time on Twitter and my essays are on my website. My primary focus (and where I focus) is on Flow Club.