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
Entrepreneurship
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 AI Content Needs a Guardian: Introducing Markup AI
(I realize I’ve been relatively quiet since I started my new job in January…this is what I’ve been up to. It may be the most interesting job I’ve ever had…but more to come on that over time.) I was at a recent Gartner CEO conference on AI in New York City, and one phrase keeps rattling around in my brain: “There is such a rapid pace of development that we are regularly seeing ‘obsolescence before maturity.’” In other words, by the time AI products reach early adoption in the market, they’re already obsolete. But here’s the thing – while everyone’s racing to build the next AI breakthrough, they’re missing a massive problem hiding in plain sight. AI has fundamentally changed…
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…
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…
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…
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…
When it’s Time to Hire Your First Chief Business Development Officer
(Post 1 of 4 in the series of Scaling CPDO’s). For most startups the idea of hiring a CBDO is a pipedream, it’s a role that only global corporations have, right? After all, strategic partnerships and M&A are rare events for a startup and can be handled by the founder/CEO, or potentially by someone in Sales. If a startup is partner or channel heavy, those areas may be the focus of the Sales team in general. Or, if there is sporadic M&A activity that can be handled by external advisors or bankers. So how do you know when it’s time to hire your first CBDO? You know it’s time to hire a CBDO when you are spending too much of…
You’ve Seen One, You’ve Seen One
Like all CEOs and VCs, I’m a big believer in the power of pattern matching. I just wrote a whole blog post about the limits of pattern matching after hearing the quote above at a board meeting recently. But then a little alarm rang in the back of my head, and realized that I wrote about the value and limitations of pattern matching here years ago with an even better quote from my father-in-law: When you hear hoof beats, it’s probably horses. But you never know when it might be a zebra. So rather that rewrite that entire post, I thought I’d just add onto it a bit here with a current example in my head about executive recruiting and…
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,…