It’s good that my friend Brad Feld‘s new book (co-authored by Dave Jilk, who I’ve also known on and off over the years), is divided into 52 chapters and is designed as a bit of a devotional, to be read one chapter per week. Each chapter of The Entrepreneur’s Weekly Nietzsche: A Book for Disruptors is, as the authors write in the Introduction, worth “chewing on a while.” The structure of the book is laid out as: The book contains fifty-two individual chapters (one for each week) and is divided into five major sections (Strategy, Culture, Free Spirits, Leadership, and Tactics). Each chapter begins with a quote from one of Nietzsche’s works, using a public domain translation, followed by our…
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Entrepreneurship
How to get the most out of working with a CEO Mentor or CEO Coach
(This is the third in a series of three posts on this topic.) In previous posts (here, here) , I talked about the difference between Mentors and Coaches and also how to select the right ones for you. Once you’ve selected a Mentor or Coach, here are some tips to get the most out of your engagement. Starting to work with a CEO Mentor is fairly easy. Give them some materials to help understand your business, and then come prepared to every session with a list of 1-2 topics that are keeping you up at night where you want to benefit from the person’s experience. Kicking off a CEO Coach engagement is more in-depth. I always recommend starting to work…
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…
How to Select a CEO Mentor or CEO Coach
(This is the second in a series of three posts on this topic.) In a previous post, I shared the difference between CEO Mentors and CEO Coaches. I’ll share with you here how to select the Mentors and Coach who are right for you. First, you need to find candidates. Whether you’re talking about CEO Coaches or CEO Mentors or both, getting referrals from trusted sources is the best way to go about this. Those trusted sources could be your VC or independent board members, friends, fellow CEOs — or of course Bolster, where we have a significant number of Coaches and Mentors and have made it our business to vet and vouch for them. Selecting a CEO Mentor is…
The Difference Between a CEO Coach and a CEO Mentor and Why Every CEO Needs Both
(This is the first in a series of three posts on this topic.) Harry Potter was lucky. He had, in Albus Dumbledore, the ultimate wise elder, in his corner. Someone who could teach him how to be a better human being (er, wizard), how to be more proficient with his wand and spells, how to think strategically and defeat the bad guys. All of us would benefit from having an Albus Dumbledore in our lives. But most of us don’t — and most of the people we’d call on to be that wise elder in our corner aren’t capable of the full range of advice and counsel that Dumbledore is. Why work with a Coach or a Mentor? I’ll start…
Soliciting Feedback on Your Own Performance as CEO
(Excerpted from Chapter 12 of Startup CEO) As a CEO, one of the most important things you can do is solicit feedback about your own performance. Of course, this will work only if you’re ready to receive that feedback! What does that mean? It means you need to be really, really good at doing four things: Asking for feedback Accepting feedback gracefully Acting on feedback Asking for follow‐up feedback on the same topic to see how you did In some respects, asking for it is the easy part, although it may be unnatural. You’re the boss, right? Why do you need feedback? The reality is that all of us can always benefit from feedback. That’s particularly true if you’re a…
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…
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 Job is Your Customer Hiring You to Do?
My friend George, one of our co-founders at Return Path (according to him, the best looking of the three), has a wonderful and simple framing question for thinking about product strategy: what job is your customer hiring you to do? No matter what I’m working on, I am finding George’s wisdom as relevant as ever, maybe even more so since I am still learning the new context. Why is this a useful question to ask? It seems really simple – maybe even too simple to drive strategy, doesn’t it? It’s very easy in technology and content businesses (maybe other spaces too) to get caught up in a landslide of features and topics. In a dynamic world of competition and feature…
OnlyOnce, Part XX
I realize I haven’t posted much lately. As you may know, the title of this blog, OnlyOnce, comes from a blog post written by my friend and board member Fred Wilson from Union Square Ventures entitled You Are Only a First-Time CEO Once, which he wrote back in 2003 or 2004. That inspired me to create a blog for entrepreneurs and leaders. I’ve written close to 1,000 posts over the years, and the book became the impetus for a book that another friend and board member Brad Feld from Foundry Group encouraged me to write and helped me get published called Startup CEO: A Field Guide to Scaling Up Your Business back in 2013. Today is a special day in…
Sometimes a Good Loss is Better than a Bad Win
I just said this to a fellow little league coach, and it’s certainly true for baseball. I’ve coached games with sloppy and/or blowout wins in the past. You take the W and move on, but it’s hard to say “good game” at the end of it and feel like you played a good game. And I’ve coached games where we played our hearts out and made amazing plays on offense and defense…and just came up short by a run. You are sad about the L, but at least you left it all out on the field. Is that statement true in business? What’s an example of a “bad” win? Let’s say you close a piece of business with a new…