I am a voracious reader, which is hilarious because when I was younger and bored, my mom would say “Read a book!” to which I always lamented “But reading is boring.” How we change.
May was no exception to me reading a lot, and actually I read a lot more in May than I have most other months recently. Part of that was due to a cross-country trip in which I had a lot of plane time to read, but I also think that May was an exceptionally good month for good writing.
Here are the articles and books I read in May that I found really impactful.
The Hard Thing About Hard Things
On my trip to New York and Boston I read Ben Horowitz’s incredible book The Hard Thing About Hard Things. Because of some recent professional challenges I have been doing a lot of thinking about management and building a company (see Manager Mistakes), so this book came at exactly the right time for me. Some of the more impactful takeaways for me were:
- No matter how dire the situation seems, there is always a way out. Sometimes you just have to make the really hard call, with minimal information, and execute like hell to figure it out. Sometimes you’ll fail, but often if you go at it this way you’re going to succeed.
- There are two different types of leaders – Type 1 and Type 2. Type 1 leaders move quickly and are comfortable making decisions without complete information. Type 2 leaders want all the information and only then really start making decisions. Often Type 1 CEOs will have a Type 2 executive suite and vice versa, which is why it’s so rare for someone internally to follow as CEO. The power dynamics are all wrong, and will either lead to decisions being made too quickly or not at all. A necessary balance should exist.
- Ben had some extraordinary circumstances and market dynamics when he was CEO, and the way he got through it was by having an amazing team that was just as invested in the company as he was. But, sometimes, you have the make the hard decision yourself. Leadership is lonely.
This book is the best book I have ever read about leadership and business. I highly recommend the read.
Startup CEO Impostor (Phenomenon?)
I’ve always respected Dan Shapiro an an entrepreneur and had the chance to hear him speak at a conference when I was working for Distilled. In this post, he dives deep into the CEO Impostor phenomenon, as one leading thinker on the subject calls it, and about not only how widespread it is but also why it can actually be powerful as long as we do not let the negative sides of it affect us.
Subtle Mid-Stage Startup Pitfalls
Jessica Livingston, at YC, lays out many of the pitfalls she sees startups make once they’ve closed funding. Included in there are:
- It never gets easier. The more successful you are, the more work it is.
- You are going to have to become a manager. You can learn to be a decent manager.
- Don’t hire too fast.
- Don’t talk to corporate development.
Why Jay Z’s Tidal Is A Complete Disaster
An amazing teardown on Jay Z’s entrepreneurial success to this point and some of the reasons why Tidal doesn’t seem to be working. Hattip Michael King on this one.
The Black Art of Saas Pricing
Patrick McKenzie (Patio11) is one of my favorite writers. I always wish that he wrote more, like he did back in the day, and occasionally I come across some of his old stuff that still blows my mind. As I was doing some research this week about SaaS pricing, I came across this incredible post that opened up my eyes to a few very smart areas about how to find the right price for your business. Avoid the race to the bottom (that Google and Facebook will win anyways).
A Few More Reads
Here are the rest of the reads from this month that I recommend.
- The Rise and Fall of Subway (The Star)
- Hiring Your First Product Manager (Learning By Shipping)
- How My Startup Dropped From $100k to $0 Overnight (Medium)
- Dropbox’s Secret For Saving Time in Meetings (Inc.com)