Category

Bolster

Signs your critical functions aren’t scaling – three webinars

This is a topic we write about obsessively in Startup CXO: A Field Guide to Scaling Up Your Company’s Critical Functions and Teams — in fact, it’s basically the whole point of the book! I’ll write some more specific posts here in the coming weeks that take some excerpts from the book, but Bolster is putting on three free and open webinars we’re calling our “Bolster-up Series” over the coming weeks that I want to share with everyone who reads StartupCEO.com. In this series, I’ll be doing short interviews with CEOs who we work with at Bolster on the different aspects of scaling specific functions, how they diagnosed those problems, and how they leveraged on-demand executive talent to solve those…

My new Startup Board Mantra: 1-1-1

Last week, I blogged about Bolster’s Board Benchmark survey results, which really laid bare the lack of diversity on startup boards.  There are signs that this is starting to change slowly — one big one is that of all the board searches we are running at Bolster, about ⅔ of them are open to taking on first-time directors; and almost all are committed to increasing diversity on their boards.   This is also something that I would expect to take some time to change.  Boards are small.  Independent seats aren’t necessarily easy to open up.  Seats don’t turn over often.  And they take a while to fill, as CEOs are thorough in their recruitment and selection process. My new mantra for…

The Startup Ecosystem Needs More Independent Board Members – That’s the Clearest Path to Having Better and More Diverse Boards

I love having independent directors on my Board.  They are a great third leg of the stool alongside a CEO/Founder and VCs.  They provide the same kind of pattern matching and outside point of view as VCs — but from a completely different perspective, that of an operator or industry expert.  The good ones are CEOs or CXOs who aren’t afraid to challenge you.  Equally important, they’re not afraid to challenge your VCs.  At Return Path, I always had 2 or 3 independent directors at any given time to balance out VCs, and some have become great long term friends like Scott Petry, Jeff Epstein, and Scott Weiss.  At Bolster, we’re already having a great experience with our first independent,…

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 a couple of eBooks. Once all of that is done, I’ll put some digests up here on StartupCEO.com as well as make the eBooks available for download. But the gist of it is that we are working hard to break the logjam of diversity on startup boards, and we’re starting to meet with some great success with our clients.

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 is our whole founding team.  When Jack and I started Return Path, we were 29.  This time, we were 49 — and the average age of the founders was probably 46 or 47.  The bottom line is that we don’t know everything about the business we’re building, but we know what we’re doing in terms of building…

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 on-demand economy for executives. More than ever before, executives are seeking out roles that distinctly aren’t full-time for a variety of reasons – they’re in between full-time roles and want to stay engaged and meet a wide range of potential employers; they’re retired or semi-retired/post-exit and want to keep working, just not full-time; they’re fully employed but are looking for advisory opportunities to…

Introducing the Bolster Board Benchmarking Survey

Over the years,  I’ve had a list of nagging questions every time I’ve contemplated my board, but didn’t have anyone I could turn to who had deep, broad advice on this topic. Those questions were: How big should my board be at this stage?   How many independent directors should I have?  What is the right profile of an independent director?  How many options should I give a board member?  How do I find the best, diverse, talent for my board openings? That’s why Bolster is excited to announce the launch of our first CEO tool: Board Benchmarking. This application (which is free!) is the first of a series of tools that we’re designing to help CEOs understand the performance, design,…

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 companies — and that there’s a high degree of correlation between more independent boards and higher performing companies as well. There’s also a lot of research out there that shows that teams which have diversity of gender and race/ethnicity perform better. And everyone who has ever been on a high-functioning board of directors knows that a board is…

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 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…

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 that not only are there different types of gig economy roles…there are several different archetypes of gig economy executives, too. …

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 team to 50 employees. My long time friend and former board member Greg Sands once compared the phenomenon of companies…