Ceo

Matt Blumberg has a new book out titled Startup CXO: A Field Guide to Scaling Up Your Company’s Critical Functions and Teams . It’s a follow-up to his previous book, Startup CEO: A Field Guide to Scaling Up Your Business. I’ve been working with Matt since 2000. That year, we merged two companies: Return Path and Veripost. Matt was the co-founder/CEO of Return Path. Fred Wilson was his lead investor. I was the lead investor for Veripost. The two companies did the same thing and were the only two competitors in a nascent category called “email change of address” (Veripost’s original name was IECOA which stood for “Internet Email Change of Address”). They were bashing each other over the head in a non-existent market as the Internet bubble began collapsing. ...

I used to love the Matrix’s Red Pill / Blue Pill metaphor and still use it occasionally to try to make a point around dealing with reality in an entrepreneurial context. Several years ago, I became deeply bummed out about how this metaphor was being used in politics and gender equity situations. It’s gotten worse since then, and I find many of the cases it is used in and the people who use it reprehensible, so I don’t use it much anymore. ...

Seven years ago this week, I posted about a new book in our Startup Revolution series called Startup CEO: A Field Guide to Scaling Up Your Business , by my friend Matt Blumberg, then CEO of email marketing company Return Path in the Foundry portfolio. Today, with more around 40,000 copies sold all over the world and in multiple languages and formats, Matt and our publisher Wiley & Sons in partnership with Techstars have published a Second Edition of Startup CEO, which you can pre-order here . ...

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.” ...

Recently, I was talking to a CEO of a company I’m on the board of. We were discussing a problem in the category of something new Is fucked up in my world every day He gave me a great idea. He apparently plays a game with his young (I think around 10 years old) daughter. When they are sitting around in the evening, she occasionally says “Daddy, give me a CEO problem.” He does, she thinks about it a little, and then gives him a solution. He suggested to me that this often helps break him out of whatever thought rut he is in given how wacky and creative the answers typically are. ...

This showed up in my inbox the other day from a friend of 20 years. He’s been involved in a number of companies that we’ve invested in over the years in different senior and/or co-founder roles, including CEO. It was short and sweet but captured the essence of something I often talk about with founders. Heard you and Jerry on CPR this morning , nice job! What struck me was your point about the gap between expectations in the role of CEO or startup founder, or investor – and the reality of depressive events/emotions that are often present – but no one gets to expose or relinquish. ...

I heard a great line from a CEO recently: “I don’t want to play hurt.” I loved that line. In my world, some companies beat their Q416 numbers. Others made their Q416 numbers. Some missed their Q416 numbers. That’s life. Any VC who says otherwise (e.g. “All my companies are killing it”) is either full of shit or doesn’t have very many investments. It’s especially true by Q4 when a budget was finalized in Q1 since Q4 is by far the hardest quarter to forecast / predict. ...

Lately, I’ve been stewing over increased complexity being generated by companies around their organization approaches. While this activity varies by stage, in many cases the leadership team expands to a large (greater than six) number of people, there become two executive teams (the C-Team and the E-Team), the CEO gets sucked into endless distractions and working “in the company” rather than “on the company”, and I could go on with a 1,000 word rant on the challenges and complexity. ...

I woke up this morning thinking about people who have a desire to please. This is not my personality type, but I encounter it regularly. Amy often describes herself as an “approval-seeking people pleaser” and I’ve learned a lot from my 30 years of interacting with her. With CEOs I often notice the pleaser personality in the context of employees. The pleaser wants everyone around him to be happy. This creates a positive reinforcement dynamic for the CEO – if everyone is happy, things must be good. If employees aren’t happy for any reason, that becomes a priority for the CEO to solve. ...

This cliche, which has uncertain attribution (Winston Churchill, Rahm Emmanuel, M. F. Weiner) is a priceless line that gets tossed out periodically, especially in the middle of a crisis. Over the years I’ve been involved in many business crises. I qualify this, since my crises have never involved life and death or the survival of the human race. But they are still crises. Some have lasted moments while others have lasted months, and I can think of one that went on for three years – or at least took three years to dig out of. ...