As part of my three blog posts to celebrate the 250th anniversary of America’s founding this long weekend, this is the Medium (yesterday’s was the Small). I’ve written about two intersecting topics on this blog over the years. In 2011, I wrote what I called “the beginnings of a roadmap” to fix America’s badly broken political system — a short list of structural reforms framed, as I noted at the time, as “a typical entrepreneur’s approach.” And in 2021 and 2023, I wrote twice about whether CEOs should wade into politics — moving gradually from “only when it directly affects your business” to “also when it indirectly affects your business, including the health of democracy itself.” Fifteen years later, I…
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Culture
July 4, 2026, Post I: Country Over Self redux
I’m going to write three blog posts to celebrate the 250th anniversary of America’s founding this long weekend, one per day. They fall into Small, Medium, and Large t-shirt sizing. Today, the Small. I launched a limited edition podcast series called Country Over Self: Defining Moments in American History in October 2024 – at the time, I blogged about it here. The series had 13 episodes in which I interviewed prominent historians about individual presidencies and critical moments to analyze the premise of presidents choosing country over party or country over self (or not). My hope was that, in some small way, telling some of our shared stories and highlighting some of our shared values as a country might plan…
Chatting with my DNA – a fascinating personal use case and a deep rabbit hole
This one has nothing to do with running a company. But it’s one of the most fascinating things I’ve done with AI, and I fell down such a deep rabbit hole that I have to share it. My friend Chad Dickerson — former CEO of Etsy, now an executive coach — mentioned that he’d uploaded his raw DNA file to an AI and started asking it questions. My reaction was something like: wait, you can do that? You can. Here’s how. If you’ve done 23andMe (or Ancestry.com — the process is similar), you can download your raw DNA data file. It’s just a text file full of SNPs — single nucleotide polymorphisms, the genetic markers that make you you. Upload…
Curated Reading on AI
One of the hardest things about being a CEO in the AI era isn’t the technology itself — it’s the firehose of information about the technology. There’s so much being written about AI right now that it’s almost impossible to separate the signal from the noise. Hot takes, doomsday predictions, breathless hype, vendor pitches dressed up as thought leadership — it’s exhausting. So I thought I’d do something useful and share periodically a curated basket of the most interesting reading I’ve done. Think of it as the reading list I’d hand to a fellow CEO who said, “I know I need to get smarter about AI — where do I start?” This first batch is a bit of a catch-up,…
Family vs. Team?
I used to describe our culture and our employees and our leaders at Return Path as a family. That was a mistake. It was just plain wrong. It served us well in some respects, but it bit us in the ass on others. Great groupings of people at work are teams, not families. You can have a highly functional family. But you don’t have high performing families. Work teams need to be high performing. Here’s what I mean. The family metaphor worked well at Return Path around the principles of caring for people and lifting each other up. Those elements of a culture are absolutely critical. I don’t regret them for a minute. But the downside of that metaphor is…
Should CEOs wade into Politics, Part III (From Tim Porthouse)
I’ve gotten to know a number of Bolster members over the last few years, and one who I have come to appreciate quite a bit is Tim Porthouse. I’m on Tim’s email list, and with his permission, I’m reprinting something he wrote in his newsletter this month on the topic of CEO engagement in politics and current events. As you may know, I’ve written a bunch on this topic lately, with two posts with the same title as this one, Should CEOs wade into Politics (part I here, part II here). Thanks to Tim for having such an articulate framework on this important subject. Your Leadership Game: “No Comment.” Should you speak up about news events/ politics? Most of the time,…
Inquiry vs. Advocacy
My Grandpa Bill used to not want to talk about himself at dinner parties. When one of us asked him why one day, he said, “I already know what I have to say. What I don’t know, is what the other person has to say.” There are a few principles I learned years ago in a workshop that my coach Marc led for us called Action/Design. I’m going to try writing a few posts about them, and you can find some articles on them here. Inquiry vs. Advocacy is simple. Understand the balance of when you ask and listen vs. when you speak in a given conversation. Both are important tools in the CEO tool belt. My rule of thumb…
Bring People Along for The Ride, Part I of II
One of the CEOs I mentor asked me the other day asked me this question: I need to start making my organization think differently – more like a startup that needs to scale and less like a project. People need to start doing more specific jobs and not swarm all over everything. How do I get people to “get” this without freaking out? Every CEO faces dilemmas like this all the time. One of my management mantras over the years has been, “You have to bring people along for the ride.” Fundamentally, that means two things. I’ll write about one of them here today and save the other for next week. First, bringing people along for the ride means you…
Our Operating Philosophy – the Mostly Self Managed Organization (MSMO)
Last week, I wrote about the concept of the Operating Philosophy, and how it fits with a company’s Operating Framework and Operating System and defines the essence of who you are as a company…what form of company you are. While we had a loose Operating Philosophy at Return Path, we never really crisply articulated it, and that caused some hand-wringing at various points over the years, as different people interpreted our “People First” mantra in different ways. So this time around at Bolster, we’re trying to be more intentional about this up front. We have labeled our company a “Mostly Self Managed Organization” or MSMO (pronounced Miz-Moh). We made those up. Our Operating Philosophy – we are a Mostly Self-Managed…
The Concept of the Operating Philosophy
I’ve always been a big believer in the Operating Framework and the Operating System as two of the management underpinnings behind every well run company. The Operating Framework is the company’s Mission, Vision, Values, Strategic Objectives, and Key Metrics. Companies have all sorts of different labels for this, from Balanced Scorecard to Salesforce’s V2MOM to Patrick Lencioni’s 6 Questions. It’s what you have to define up front, refresh annually, and tweak quarterly so that people in the company are aligned and know where you’re going. The Operating System, as I wrote extensively about in Startup CEO, is the collection of practices, meetings, mailing lists, routines/rhythms, and behaviors that your company and team use and depend on to run the business…
Momentum and Confidence: Everything Matters
As I stared at a dugout of dispirited 14 year old boys Saturday afternoon in our tournament championship game, I found myself talking to my fellow coach Mitch about a book I’d read a few years ago (turns out 14) called Confidence: How Winning Streaks and Losing Streaks Begin and End, written by HBS professor Rosabeth Moss Kantor. While that original blog post is pretty specific to something that was going on at that point in time in my prior company, the thinking in the book about momentum and the role it plays in our psychology, about sports, about business, and about life in general, is timeless. Watching this team of teens go through ups and downs within an hour was…