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A first-time CEO writes about entrepreneurship and email

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Should CEOs wade into Politics?

This question has been on my mind for years. In the wake of Georgia passing its new voting regulations, a many of America’s large company CEOs are taking some kind of vocal stance (Coca Cola) or even action (Major League Baseball) on the matter. Senate Majority Leader Mitch McConnell told CEOs to “stay the hell out of politics” and proceeded to walk...

How to Select a CEO Mentor or CEO Coach

(This is the second in a series of three posts on this topic.) In a previous post, I shared the difference between CEO Mentors and CEO Coaches. I’ll share with you here how to select the Mentors and Coach who are right for you.  First, you need to find candidates.  Whether you’re talking about CEO Coaches or CEO Mentors or both, getting referrals...

The Difference Between a CEO Coach and a CEO Mentor and Why Every CEO Needs Both

(This is the first in a series of three posts on this topic.) Harry Potter was lucky.  He had, in Albus Dumbledore, the ultimate wise elder, in his corner.  Someone who could teach him how to be a better human being (er, wizard), how to be more proficient with his wand and spells, how to think strategically and defeat the bad guys. All...

Addicted to Ruthless Efficiency

Last week I wrote about The Tension That Will Come With the Future of Work.  No one knows what the post-pandemic world of office vs. remote work will look like, but there are going to be some clear differences between how people will respond to being in offices or not being offices going forward.  As I said in that post, I think the natural, gravitational...

OnBoards Podcast

My podcast with OnBoards is live, talking with Raza and Joe about the importance of adding independence, first-time directors, and diversity to startup boards, and how Bolster helps companies achieve that quickly and inexpensively. I’m writing a lot about Boards at the moment on the Bolster blog. We’re compiling all of those posts into...

The Tension That Will Come With the Future of Work

The Tension That Will Come With the Future of Work A lot has been written about the Work From Anywhere life that knowledge workers are leading right now due to the pandemic, and what will come next.  Fred has a great post on it, and I’m curious to see how his and Joanne’s “Home Office Away From Home” space called FrameWork does when it opens. ...

Soliciting Feedback on Your Own Performance as CEO

(Excerpted from Chapter 12 of Startup CEO) As a CEO, one of the most important things you can do is solicit feedback about your own performance. Of course, this will work only if you’re ready to receive that feedback! What does that mean? It means you need to be really, really good at doing four things: Asking for feedback Accepting feedback...

Second Verse, Same as the First…Except Way Better

Almost a year into my second journey as a startup CEO at Bolster, and I’m getting more and more questions from other CEOs about what it’s like doing a second startup after almost 20 years at the first one…and achieving pretty good scale by the end.  The short answer is, it’s the same, only it’s way better.  Here’s why. I’m more confident.  So...

StartupCEO.com: A New Name for OnlyOnce

Welcome to the new StartupCEO.com! I started writing this blog in May of 2004 with an objective of writing about the experience of being a first-time entrepreneur — a startup CEO — inspired by a blog post written by my friend, long-time Board member and mentor Fred Wilson entitled “You’re only a first time CEO once.”  The blog and the receptivity...

Use Cases to Bolster Your Team: How to Leverage On-Demand Talent in Your Business

(This post was written by my colleague Bethany Crystal and originally published on the Bolster blog yesterday. While I am still trying to figure out what posts to put on this blog vs. Bolster’s blog since the blogs are pretty similar, I will occasionally run something in both places.) At Bolster, we believe that 2021 will mark the rise of the...

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