OnlyOnce

A first-time CEO writes about entrepreneurship and email

Latest articles

The New Way to Scale a Board of Directors

As we wrote in Bolster’s Founding Manifesto, one of the reasons we started Bolster was to create a new way; a faster, easier, and more cost-effective way, for startup and scaleup CEOs to grow their boards of directors and make them more diverse. There’s a lot of research out there that the more independent a board is, the better it performs for...

Zoomsites

(Written by both my Bolster co-founder Cathy Hawley and me) I’ve attended two remote conferences, which Cathy dubbed “Zoomsites” — one here at Bolster and the Foundry Group CEO Summit.  Both hold interesting lessons for how these kinds of events can work well. We founded Bolster two months into the COVID-19 pandemic, and our founding team...

What Kind of Gig Economy Executive Are You?

(This post also appeared on Bolster.com). As we wrote in The Gig Economy Executive, the major societal trend to “gig,” or part-time/freelance work, has reached the C-Suite.  We created Bolster to help organize a talent marketplace out of what is mostly an informal economy today – one where VC- and PE-backed companies find trusted freelance executives...

The New Way to Scale an Executive Team

(This post also appeared on Bolster.com) As we wrote in our Founding Manifesto, Bolster was started in part to create a new way for startup and scaleup CEOs to think about growing their leadership teams. Why do CEOs need help with this? CEOs of any company have too many things to do at all times. This is even more true at startups...

The Gig Economy Executive

(This post, written by my co-founder Cathy Hawley, also appeared on Bolster.com) The gig economy is a labor market where short-term or freelance roles are more prevalent than permanent positions. It’s generally characterized by having independent contractors rather than full-time positions, but in some locations and for some types of roles, gig...

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...

Discover, share and read the best on the web

Subscribe to RSS Feeds, Blogs, Podcasts, Twitter searches, Facebook pages, even Email Newsletters! Get unfiltered news feeds or filter them to your liking.

Get Inoreader
Inoreader - Subscribe to RSS Feeds, Blogs, Podcasts, Twitter searches, Facebook pages, even Email Newsletters!