Leadership

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. ...

I love the phrase vanishing mediary. This is what I aspire to be. It’s the opposite of a visible intermediary. In our ego-fueled world, many people want to be front and center. Leaders are told to lead from the front, even if all they do is get up on a white horse and exit stage left as soon as the battle starts. We all know the leaders who are more about themselves than about the organizations and the people they lead. Many of us interact with this type of leader on a daily basis and, while it can be invigorating for a while when things are going well and there are bright lights shining all around you and celebrations around every corner, it’s often complete and total misery when things get tough. ...

As the Boulder Startup Community evolved, I started to become inundated with people who wanted to get involved. Some of these were locals while others where people looking to move to Boulder, or who had recently moved here. Some where people known to me while others were new relationships. As the momentum, size, impact, and reach of the Boulder Startup Community grew, I found myself overwhelmed by the amount of requests I was getting to get together, meet, explore ways to work together, and just generally share food and drink in the quest for figuring out ways to work together. ...

Jerry Colonna spent a few hours with me and Amy on Saturday at our house. Jerry is one of our closest friends on this planet so any time we get time with him is a treasure for us. It was a cold-ish, snowy, gloomy Colorado early winter day. Amy and I were pretty off-balance due to my blood clot so it was especially nice to be with him as he always helps rebalance us. ...

In a recent board meeting, at a particularly challenging part of the conversation, I did a retrospective of the past five years as a lead up to making a point. I prefaced it by saying “I need you to take a leader approach, not a victim approach.” I realized no one knew that I meant by this, so I told a quick story, which I first heard from Jeremy Bloom, the CEO of Integrate , retired pro-football player, retired Olympic skier, and someone I adore. ...

I got to spend a lot of time with my close friend Rand Fishkin the past few days. The first was at Denver Startup Week, where we did a panel discussion with Ben Huh and Bart Lorang where we discussed the pact between CEO and Board, the pact between Founder and Investor, and how to be transparent and direct. The next day, Rand led a full day offsite for a number of CEOs in our portfolio. ...

In yesterday’s post Mentors 4/18: Be Direct. Tell The Truth, However Hard , Joah Spearman left a very powerful comment about empathy. “The older I get the more I realize that truth is something that is best coupled with empathy. Ultimately, you have to seek to understand before you can be understood and part of telling the truth is knowing that you’ll never know someone else’s truth until you hear it directly from them rather than assuming you know what someone has experienced or what’s best for them.” ...

I’ve been thinking about the concept of “the duo” a lot recently. Many of the companies I’m involved in have either two co-founders or two partners who partner up early in the life of the business. Examples of founding partners including Andrei and Peter (Kato.im ), Keith and Jeff (BigDoor ), James and Eric (Fitbit ), and Matthew and Cashman (Yesware ). Of course there are many other famous founding duos like Steve and Steve (Apple), Jerry and Dave (Yahoo!), Larry and Sergey (Google), and Bill and Paul (Microsoft). My first company (Feld Technologies) had a duo (me and Dave) and the company that bought Feld Technologies did also – Jerry and Len (AmeriData). ...

I’m on the receiving end of phone calls and video conferences with CEOs all day long. And, at least once a day, I can feel the intense stress on the person I’m talking to oozing through the phone or the screen. The conversation is often calm and rational, but below the surface is a bubbling cauldron of pressure. Welcome to life as a CEO of a fast growing startup. Every day something new and unexpected comes at you. Often multiple things. Some are awesome. Some are ok. Some are bad. And some are awful. ...

It’s really hard to be a CEO. Becoming a great CEO takes a lot of time, work, focus, coaching, and introspection. My very close friend Jerry Colonna is hosting his second CEO Bootcamp from April 2 – April 6. Several CEOs from the Foundry Group portfolio went last year and each had an amazing time. This year I’m going to be attending as a special guest and participating throughout the four day program. ...