Management

The post is aimed at CEOs of startups who have at least 15 employees. If you don’t have a VP Finance on your team reporting to you, do yourself, your team, and your investors a favor and go hire one right now. While it’s trendy to outsource your accounting to a third party, once you hit a certain size it’s dangerous. I know there is a lot of advice going around right now – especially in the bay area – that you should focus on your product, start getting customers (or users), make them deliriously happy, and not worry about the rest of stuff for a while. The tone of the advice is fine, but it creates a total mess if you follow it without pondering the implications as you actually start to scale up revenue and expenses. ...

The phrase “dedupe your processes” was created at a board meeting I was at last week. If you know our portfolio, you probably can figure out which board meeting it was based on the use of the word dedupe. It was part of a conversation where the goal of “Simplify Simplify Simplify”, which had been turned into “Simplify Simplify Simplify“, was finally listed as “Simplify”. It sounds so obvious. But it’s so fucking hard. ...

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. ...

By definition, as a company scales rapidly, it adds people quickly. There are many things about this that are difficult, but a vexing one has to do with the leadership team. Often times, the wrong people are in senior positions. The faster a company grows, or the less experienced the CEO is (e.g. a first time founding CEO), the more likely it is a problem. Per Fred Wilson’s famous post What A CEO Does , this is one of the three key responsibilities of a CEO. ...

If you are the CEO of a VC or angel backed company, will need to raise more money in the future, are doing more than $100,000 of revenue a month, and are growing more than 25% a year, then this post if for you. In January, you finalized your budget. Unless something went horribly wrong, you made your plan in January, especially if the plan was finalized in February. Assuming things were on track, you made March and declared victory on Q1. ...

For your Sunday video watching, I encourage you to spend ten minutes of your life and watch Chris Moody ‘s Commencement Address to the Auburn 2016 graduates. His message is simple: Work Hard. Be Kind. Having worked with Chris for many years, it’s a great summary of how he lives his life. And he ends with a magnificent Dalai Lama quote. “Be kind whenever possible. It is always possible.”

As I procrastinate from going for a run this morning, I started writing a post titled The Pro-Rata Gap Myth. After two paragraphs, I got tired of writing it and hit the “this is bullshit ” wall – it’s too complicated to explain a myth that I’m not sure even matters. So I deleted the post and decided to tell a story instead. This is a story I roll out occasionally with CEOs to help them explain how their words can easily be misinterpreted by their teams, especially as the teams get bigger. But it’s also a way that CEOs misinterpret what their investors or board members (or chairperson) is saying. And it creates endless organizational waste and misalignment when the CEO / investor / board member / leader isn’t clear about what she is saying and who her audience is. ...

Jon Hallett , a prolific angel investor and successful entrepreneur who I’ve gotten to know over the past few years, dropped a major knowledge bomb on me yesterday afternoon when he sent me a post from David Politis titled This is How You Revolutionize the Way Your Team Works Together… And All It Takes is 15 Minutes . I remember having a meal in December 2011 with David at the Plaza Food Hall in New York and talking about BetterCloud which we foolishly passed on investing in. So I wasn’t surprised to have the reaction I had after reading the post, which I said out loud to myself. ...

I had a great interaction with a friend several months ago. The question he asked was: “How do you beat Michael Jordan at sports?” I thought about it for a second. I knew Michael Jordan was a good golfer and I don’t play golf. I figured he was in better shape than me and could beat me on a track. There is no way I could ever beat him at basketball. And baseball – well this video kind of says it all. ...

I was catching up on a bunch of reading on the web from last week and came across a post by Lars Dalgaard titled Thoughts on Building Weatherproof Companies . I don’t know Lars, but know of him as the founder/CEO of SuccessFactors and now a partner at A16Z, and was curious after recently reading a Forbes article about Zenefits a few weeks ago titled ‘A Lot Of Things Went Wrong’: Lars Dalgaard On Zenefits Scandal . ...