OnlyOnce

A first-time CEO writes about entrepreneurship and email

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Bolster’s Founding Manifesto

(This post also appeared on Bolster.com and builds on last week’s post where I introduced my new startup, Bolster) Welcome to Bolster, the on-demand executive talent marketplace. We are creating a platform that is the new way to scale an executive team and board. verb: bolster; 3rd person present: bolsters; past tense: bolstered; past...

Introducing Bolster

As I mentioned earlier this summer, I’ve been working on a new startup the past few months with a group of long-time colleagues from Return Path.  Today, we are officially launching the new company, which is called Bolster.  The official press release is here. Here’s the business concept.  Bolster is a talent marketplace, but not just any talent...

Startup CEO Second Edition Teaser: Thinking about Your Next Step

As part of the new section on Exits in the Second Edition of the book (order here), there’s a final chapter around you as CEO and thinking about what you do next.  I’ll start this post by saying, while am really happy with where I am now (more to come on that!), I am not happy with the way I handled my own “next steps” after the Return Path exit.  I...

Startup CEO Second Edition Teaser: Transition and Integration

As part of the new section on Exits in the Second Edition of the book (order here), there’s a specific chapter around handling the post-sale transition and integration process.   No two transitions are exactly the same.  If the buyer is a financial sponsor, you may have the same job the day after the deal closes that you had the day before, just...

Startup CEO Second Edition Teaser: Preparing Your Company for an Exit

As part of the new section on Exits in the Second Edition of the book (order here), there’s a specific chapter around Preparing Your Company for an Exit.  That’s pretty different than Preparing Yourself (last week’s post).   This chapter really focuses on two things.  One is how to think about who within your company knows about the possible...

Startup CEO Second Edition Teaser: Selling Your Company – Preparing Yourself for an Exit

One of the new sections in the Second Edition (order here) that I’m excited to share is a deep dive with several chapters on selling your company.  The next few blog posts will share some of my thinking on the subjects as they’re arranged into chapters in the book.  For many startup CEOs the culmination of their life’s work is an exit of some kind (other...

New book from Brad Feld: The Startup Community Way

My long-time friend and former Board member Brad Feld has become a prolific writer on the startup world over the years and is the person (other than me) most responsible for me getting into that scene as well. Startup CEO is part of his Startup Revolution series, which followed me writing an essay for Do More Faster, and then writing a series of sidebars...

Startup CEO, Second Edition Teaser: The Importance of Authentic Leadership in Changing Times

As I mentioned the other day, the second edition of Startup CEO is out.  This post is a teaser for the content in one of the new chapters in this edition on Authentic Leadership. As I mentioned last week, the book went to press early in the COVID-19 pandemic and prior to all the protests around racial injustice surrounding the George Floyd killing,...

Startup CEO, Second Edition

I haven’t taken a poll to figure out the overlap between people who read this blog and people that bought the first edition of Startup CEO, but I’m guessing there’s a high degree of it. If you are familiar with the book, I don’t want to bore you with a recap of what I wrote, but I thought I would devote the next several blogs to new ideas in the second...

Startup CEO Second Edition Teaser: The Sale Process

As part of the new section on Exits in the Second Edition of the book (order here), there’s a specific chapter around the sale process itself.  There are some interesting things in it — the arc and timeline of a deal, working with and through advisors vs. principals dealing with each other directly, optimizing for different stakeholders, and a wonderful...

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