August 27, 2020

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 did follow some of my own advice, but not enough of it.  I jumped back into the fray way too quickly. Some exits leave CEOs in a position of never having to work again – those are good in that they give you more time to think about what’s next and more options for what’s next, but no financial forcing function to do anything.  Some CEOs want to work again in the same field, doing another startup or being hired to run a larger company or focusing on serving on boards and mentoring other CEOs.  Some want to transition to a different kind of work entirely.   But no matter what your circumstances are, the most important thing you can do after selling your startup is to downshift and take […]


August 20, 2020

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 with a new owner and new rules for you.  Sometimes you’ll stay on with a strategic buyer as the head of a division, or the head of your product.  Sometimes you leave on Day 1.  Sometimes you leave […]


August 13, 2020

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 long sidebar by my friends and advisors Brian Andersen and Mark Greenbaum from Luma Partners on how to think strategically about an exit and how buyers think.  It’s probably worth buying the whole book just for that. But what I […]


August 6, 2020

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 deal, which conversations you keep private and which you have more in public.  I’ll save the details on that one for the book. But there’s a second topic that’s important as well.  And it’s about due diligence and disclosure schedules.  What fun!  […]


July 30, 2020

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 than being fired!). Personally, there were a range of emotions surging through me when we got to the point of a sale and while the financial reward can be enticing, there are a lot […]


July 23, 2020

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, so nothing in it specifically addresses any of those issues.  In some ways, though, that may be better at the moment since the book is more about frameworks and principles than about specific responses to current events. […]


July 14, 2020

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 edition. First, the new cover art from the publisher is kind of cool: The first question you might have is, “Why a second edition? Didn’t you say everything you […]


July 9, 2020

Back in Business

If you’ve been reading this blog for a long time (amazingly, it is over 16 years old now!), you know that my company and main professional life’s work up to this point, Return Path, was a 1999 vintage email technology company that we sold last year.  I then had a couple other interim leadership roles, first as interim CEO of another tech company in New York, then in March as the founder and interim leader of Colorado’s COVID-19 Innovation Response Team, which I wrote a series of blog posts about (this is the final post in the series, which links […]


April 5, 2020

State of Colorado COVID-19 Innovation Response Team, Part VII – Retrospective

(This is the seventh and final post in a series documenting the work I did in Colorado on the Governor’s COVID-19 Innovation Response Team – IRT.  Other posts in order are 1, 2, 3, 4, 5, and 6.) I’ll start the final post in this series by sharing the overview and retrospective deck that we created my last day and the two days after.  Governor Polis is going to share this with the National Governors Association in case other states are interested in our model or learnings. This pdf, which you’re welcome to download or just view in SlideShare, is […]


April 4, 2020

State of Colorado COVID-19 Innovation Response Team, Part VI – How This Compared to Running a Company

(This is the sixth post in a series documenting the work I did in Colorado on the Governor’s COVID-19 Innovation Response Team – IRT.  Other posts in order are 1, 2, 3, 4, and 5.) As these posts have been running, a few people have asked me to quickly compare this experience to the experience of being a Startup CEO.  And that’s an interesting way to think about it. In a lot of ways, the couple of weeks of getting the IRT up and running felt like starting up a new business, only a lot more intense.  Following the outline […]


April 3, 2020

State of Colorado COVID-19 Innovation Response Team, Part V – Wrapping Up, Days 10-12

(This is the fifth post in a series documenting the work I did in Colorado on the Governor’s COVID-19 Innovation Response Team – IRT.  Other posts in order are 1, 2, 3, and 4.) Thursday, March 26, Day 10 Sarah continuing to take over and stronger by the day Sarah cleared me to go home, only one more person to ask Deep deep dive on Mass Testing – so good to spend that time  Pretty much got the strategy right – shocking we could get that close with so little public health experience – Kyle awesome – EOC leadership briefing […]