In May 2023, Fred Wilson wrote a post about being approached by a company that had trained a large language model on all 9,059 of his AVC blog posts. They wanted to offer a chatbot called “Ask Fred.” He said no thanks. His reasoning was sharp. He’s fine with anyone using his content to train AI. He put a Creative Commons license on his blog from the start. But he didn’t want a bot pretending to be him. The whole point of his blog is the humanity — the daily conversation, the thinking out loud, the relationship with readers. A chatbot that mimics Fred Wilson isn’t Fred Wilson. It’s a parlor trick. I read that post and agreed with Fred…
Category
Leadership
Meet Chatgipity: a Unified AI Platform for Our Company
A little over a year ago, my friend Dan Shapiro, CEO of Glowforge, showed me what his team had built internally with AI tools. Not one-off ChatGPT experiments. Not an AI pilot program. A real, unified infrastructure where the whole company was using AI through a common platform with shared agents, shared memory, and shared integrations. I walked away from that conversation knowing we needed to do the same thing. A few weeks later, our VP of Technical Operations, Martin Hempstock, stood up an instance of LibreChat — an open-source AI platform that brings together all the major LLMs into a single, customizable interface. Martin had it provisioned under a new subdomain within days. It’s changed the way we work….
Why I am Writing About AI (and Why It’s Not Just About My Company)
My marketing team has been asking me to write more about Markup AI — what we do, why it matters, where we’re headed. And I will. I’m the CEO of a company that builds Content Guardian Agents to help enterprises scale AI-generated content smartly and safely. I love what we’re building. I believe in it deeply. And I’ll reference it when it’s relevant. I also love how we’re building things, since we are hardcore practitioners using AI to build our business at decent scale. But if you’ve read this blog over the years — through my two decades at Return Path, my time building Bolster, and three books on startup leadership — you know that’s never been what this space…
Announcing the launch of the Startup CXO mini-books for CFOs, CROs, CMOs, CTOs, and CPOs
I’m thrilled to announce that we created mini-books (about 80 pages long and only $9-10 on Amazon) out of five of the major functional areas covered in Startup CXO: A Field Guide to Scaling Up Your Company’s Critical Functions and Teams, part of our series along with Startup CEO: A Field Guide to Scaling Up Your Business and Startup Boards: A Field Guide to Building and Leading an Effective Board of Directors. I’ve always said that while I love all three books, in some ways Startup CXO is the best because it’s a “book of books.” While I’d still encourage all CEOs and senior executives (CXOs) to read the full manuscript, my friends and co-authors and I are happy to…
Why Executive Searches are So Slow, and What You Can Do About That as a Candidate
It’s been a big break between posts – as many of you probably know, I moved to Board Chair and left the CEO role at Bolster last summer (it’s now in the very capable hands of my friend and co-founder Cathy Hawley), and I’m now CEO of a super cool AI company called Acrolinx. So yes, that means I went through a job search – and I found my ultimate job as a result of an inbound cold email from a headhunter! The rich irony in that as someone who founded an executive search platform is not lost on me. So when a good friend of mine who is also between CEO gigs and looking at several opportunities asked me…
New Podcast – Something Old, Something New, Something Red, White, and Blue
I’ve been uncharacteristically quiet since April (I still hate non-competes and while I respect the right of the Chamber of Commerce to sue the FTC, I hope common sense prevails). Between then and now, we switched things up at Bolster, and my co-founder Cathy Hawley is now the CEO. Things are great there, and if you need any executive search help (Director to C-level or Board/Advisory/Fractional), let me know. I’ve been hard at work on a passion project while I’ve been between things professionally, and I’m excited this week to announce the launch of my new podcast mini-series, Country Over Self: Defining Moments in American History. That link is to the web site where you can see the whole plan…
Decisions
Happy Leap Day! One of the better books I’ve read in the last 6 months is James Clear’s Atomic Habits: An Easy & Proven Way to Build Good Habits & Break Bad Ones, which provides a great framework around habits. It’s worth a read, whether you’re talking about business habits/routines or personal ones. This isn’t a book review, but quickly while I have you – here’s a summary of his “laws”: HOW TO CREATE A GOOD HABITThe 1st Law: Make It ObviousThe 2nd Law:Make It AttractiveThe 3rd Law: Make It EasyThe 4th Law: Make It Satisfying HOW TO BREAK A BAD HABITInversion of the 1st Law: Make It InvisibleInversion of the 2nd Law: Make It UnattractiveInversion of the 3rd Law:…
Book Short: Less is More
Subtract: The Untapped Science of Less, by Leidy Klotz is a great read, and in concert with the philosophy of the book, this will be a short blog post. The book’s basic premise is that less is more, addition by subtraction. The author’s examples range from the genius of the Strider Bike (bike without pedals) that allows 2-year olds to ride bikes to the Embarcadero in San Francisco. Many people don’t remember that that road used to be called the Embarcaro Freeway, a massive, ugly, two-tiered structure that blocked out the views and waterfront, and that the opportunity to tear down the whole thing following the massive 189 earthquake left San Francisco with a much simpler, beautiful, liveable waterfront by…
How I Engage with the CBDO
(Post 4 of 4 in the series on Scaling CBDO’s- other posts are, When to hire your first Chief Business Development Officer, What does Great look like in a Chief Business Development Officer and Signs your Chief Business Development Officer isn’t Scaling) Other than the weekly executive meeting, your day as a CEO rarely has an entry of “meet the CBDO.” Because of the infrequency of deals it’s critical to engage with the CBDO with a regular cadence so that when something does come up you’re not getting to know each other again. Anyway, a few ways I’ve typically spent the most time or gotten the most value out of CBDOs over the years are: One way to engage with…
Signs your CBDO isn’t scaling
(This is the third post in the series… The first one When to Hire your first CBDO is here, and What does Great Look Like in a CBDO is here). The metrics for understanding whether or not your CBDO is scaling differs from other functions like Sales, People Ops, Customer Service, and Finance because throughout the scaling process the CBDO team is likely to be small. So how do you know if your CBDO is scaling if they’re essentially the same size regardless of what the rest of your company is doing? I have found that CBDOs who aren’t scaling well past the startup stage are the ones who typically operate in the following ways. First, a CBDO who isn’t scaling is…
Fighting Confirmation Bias
I was mentoring a first time founder the other day who asked me, “How do you know what advice to follow and what advice not to follow?” (For the record, it’s a little ”meta” to answer that question!). I talked about looking for patterns and common themes in the advice from others and exercising judgment about how to pick and choose from competing pieces of advice. But then he asked me how I fight confirmation bias when I’m exercising judgment and incoming advice. Fighting confirmation bias is both incredibly important and incredibly difficult, and I’d never articulated my thoughts on that before, so I thought I’d do that here. The way you have to train yourself to fight confirmation bias…