I read Ben Horowitz’s The Hard Thing About Hard Things last weekend. This is the third time I’ve read it. It gets better each time. If you are a CEO and you haven’t read it, buy it right now and read it next weekend.
There are endless gems in the book, many of them from Ben’s own experience. My favorite of all time, that stays with me through all the work I do, is his distinction between “peace time” and “war time.”
I think the first time he wrote about this was in his post in 2011 titled Peacetime CEO/Wartime CEO. There has been plenty of commentary on the web about it (see The Myth of the Wartime and Peacetime CEO, which really only says a CEO has to be effective in both wartime and peacetime to be successful.)
Ben has an incredible rant in the post that starts off with:
Peacetime CEO knows that proper protocol leads to winning. Wartime CEO violates protocol in order to win.
The rant is worth reading every single word, but I want to highlight and comment on a few of my favorites.
The first one is:
Peacetime CEO always has a contingency plan. Wartime CEO knows that sometimes you gotta roll a hard six.
BSG fans know about rolling a hard six even though the definition is contested by pilots who think non-pilots confuse planes with dice. In wartime, the odds are often very against you. Sometimes you just have to get lucky.
Another one that I love is:
Peacetime CEO strives for broad based buy in. Wartime CEO neither indulges consensus-building nor tolerates disagreements.
Things during wartime are intense. Decisions have to be made quickly. Many will be wrong, need to be overturned, and new decisions have to be made. Sitting around arguing about what to do simply doesn’t work. Get all the ideas out on the table, but then choose. And then execute like crazy.
Peacetime CEO sets big, hairy audacious goals. Wartime CEO is too busy fighting the enemy to read management books written by consultants who have never managed a fruit stand.
Your big hairy audacious goal in wartime is not to die.
As an investor, I’m involved in some companies operating in peacetime and others in wartime. There’s a lot of emotional dissonance during the day as I go back and forth between them. I’ve learned how to be calm in both modes and deal with my emotions outside the context of interacting with CEOs, founders, and leaders. But, Ben’s metaphor of peacetime vs. wartime has been so incredibly helpful to me as an investor in identifying what mode I’m in that I should probably get him some sort of a gift as a thank you.
On Saturday, I polished off Hot Seat: The Startup CEO Guidebook. I started it last weekend at the tail end of my Weekend Reading on Startup Communities but four books weren’t in me so I didn’t finish it.
It was excellent and is now on my “all startup CEOs must read” list. My recommended book list for startup CEOs is very long, but there are only three books on the must read list.
and now #3: Hot Seat: The Startup CEO Guidebook by Dan Shapiro.
All three are from experienced CEOs. Each is a delightful mix of stories, advice, and experiences. They are all contemporary, highly relevant, and fun to read. Regardless of the number of times you’ve been a startup CEO, from having started ten companies to being an aspiring CEO/founder, you will learn a lot from each of them.
I don’t think I’ve ever physically been in the same place as Ben, but we’ve exchanged emails in the past and he was willing to allow me to republish his classic essay The Struggle in the book I wrote with my wife Amy – Startup Life: Surviving and Thriving in a Relationship with an Entrepreneur. In contrast, I’ve known and worked with Matt since 2001 when I first invested in his company Return Path (well – it’s a little more complicated than just an investment – see my post Return Path Launches Email Intelligence from 2012 where I recounted some of the story.)
Return Path is an extraordinary company that I’m proud to have been involved with for the past 12 years. At our board meeting last week, Matt gave me and Fred Wilson our 12 year anniversary gift – a pair of red Return Path-branded Adidas sneakers. I still vividly remember the phone call Fred and I had where we cut a deal to merge two nascent companies – Veripost and Return Path – in what became Return Path. We cut a deal in 10 minutes – I offered up a 50/50 merger and Fred suggested he wanted a little more since Return Path had raised 3x the money Veripost had. I responded with “how about 55/45″ and Fred said “it’s a deal.”
Matt has become one of my best friends and I treasure every minute I get to spend with him.
Dan is a new friend. The first email I remember getting from him was from 9/3/13, titled My new project: Robot Turtles, and he acknowledges in Hot Seat that it’s the one time he spammed everyone in his address book. I don’t know why I was in his address book, so I asked Dan, and he dug up his very first email to me, which happened to be about the term sheet series that my partner Jason Mendelson and I wrote that lead to our book Venture Deals.
The first substantive email exchange we had was on 3/18/15, as a result of an intro from Ben Huh, the CEO of Cheezburger and another long time friend. We went back and forth on a rapid fire thread about Dan’s newest company Glowforge and the round he was starting to raise. We agreed to terms on a financing on 4/20/15 and closed a $9m financing with True Ventures on 5/8/15, at which point Amy and I went to Paris to celebrate (actually, we just went on vacation for one of our quarterly off the grid vacations.) There were a number of articles around the financing, but the best – and most thorough explanation of the company – was in Natasha Lomas‘s Techcrunch article Seattle’s Glowforge Is Building A Maker Machine To Challenge Amazon Prime.
Suffice it to say that in 75 days, I’ve gotten a good dose of Dan and am having an absolute blast working with him. He’s definitely got a healthy dose of evil genius combined with deep wisdom from being around the startup block a number of times. He’s tireless, intense, but delightfully funny and witty. He’s got extremely broad range as a CEO and entrepreneur, which comes through in his daily activities as well as his writing.
Which brings me back to Hot Seat. Like Matt and Ben’s books, it’s very fast paced. The chapters are short, written in first person, and easy to read. He’s not shy about calling things out clearly, including his own crazy experiences, especially the things he totally fucked up or had no idea about when he first encountered them. His examples are great, including some from mutual friends including Rand Fishkin and Ben Huh. The book is well organized and easy to dip in and out of. He flogs Venture Deals: Be Smarter Than Your Lawyer and Venture Capitalist, which I put in the flattering special bonus category. And – he’s got great footnotes in each chapter which give you a special dose of his sense of humor.
I hope to get to work with Dan for a long time on Glowforge. But, regardless, I know I’ll be regularly recommending Hot Seat: The Startup CEO Guidebook to every CEO I know.