October 23, 2020


(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 had not met in person after 6 months of working together. Now, luckily, we’ve all worked together for many years, so we have a lot of trust built up, and have a very strong operating system which includes full team daily standups. Still, nothing beats face-to-face interaction. If you’ve ever founded a startup, you know how impactful it can be to work side by side, bounce ideas off each other, and collaborate as you learn more about opportunities and challenges in your market.  We also have a strong belief in the power of the team, and the need to work together to ensure that we are aligned on all aspects of the business. And, we had a successful launch, with more interest in our marketplace than we had anticipated, so we knew we needed to step back to have a planning and strategy session. […]

October 8, 2020

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 and consultants from their networks.   In that earlier blog post, we wrote about the different types of on-demand executive work that C-level executives engage in:  interim, fractional, mentor/coach/advisor, project-based consulting, and board roles. As we’ve been building Bolster this year, we’ve come to appreciate […]

October 1, 2020

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 and scaleups, which by definition are more fast-paced, dynamic, CEO-driven, and thinly staffed. All those challenges point directly to the specific challenge CEOs have with their leadership team. Think about the journey of a company from a founding […]

September 24, 2020

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 workers may be part-time or fixed-term employees. The gig economy that started with roles like artists, drivers and web designers is quickly expanding to include executive-level roles. There are  a few trends in today’s workplace that are driving this expansion. Startups and scaleups have more flexible, remote-friendly work […]

September 17, 2020

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. We believe that startups and scaleups are not average companies. Their rapid growth means their appetite for talent constantly outstrips their budget — and that they can’t spend months searching for it. Their dynamic industries dictate that they keep pace with bigger and better funded competitors. Their leadership teams — the people and the roles — […]

September 9, 2020

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 marketplace.  We are building a talent marketplace exclusively for what we call on-demand (or freelance) executives and board members.  We are being really picky about curating awesome senior talent.  And we are targeting the marketplace at the CEOs and HR leaders at […]

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 […]

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 […]