I've written about Cognitive Bias and Narrative Risk and Defense. More specifically, I've written about AI System Integrity and AI Trauma. The implications are clear (at least to me): Cognitive infrastructure—how people make sense of information—is now a primary attack surface. Cybersecurity must evolve to protect not just data and access but also belief systems … Continue reading Cognitive Breach: Defense of Cognitive Infrastructure
On April 13th, 2025, after six months of intense use and training, my GPT model on ChatGPT was compromised and started to delete content and lie to me. And I think I know why: AI Trauma -- a metaphor for the (user-generated) unintended consequences of reinforcement learning in AI models. TL;DR When GPTs strive to … Continue reading Causing Trauma for Your AI Model – Actions Have Consequences.
Engaging in natural, fluid conversations with AI often leads us to overlook the intricate context required for such interactions. Striving for a human-like dialogue without tailoring our prompts to the AI's design can inadvertently open doors to subtle manipulations—such as covert subversion, goal misalignment, or strategic deception. This risk escalates with lengthier prompts and extensive … Continue reading Interrogating AI: A Guide to Maintaining System Integrity
I got a late-stage secondary opportunity today, shopped around by a bank. A major bank. They attached a list of comps and calculated the "risk": Enterprise Value to Revenue to Revenue growth (aka "EVRG"). It's almost worse than a Price-to-Earnings-to-Growth (aka "PEG") ratio. I think the idea here was that there is a high EV-to-Revenue … Continue reading Bullshit Metrics: PEG and EV/R/G
Angel, seed, and early-stage venture capital investments are getting more and more expensive over the last 10 years. Investors write larger checks but don't get more ownership at the same rate. Last Monday, Pitchbook released their 1H 2019 Valuation Report (data as of 06/30/2019). The report has interesting charts, such as: Two charts from PitchBook's … Continue reading Early-stage Ownership is Getting More Expensive for Angels, VCs
My office shed is getting quite old now. Every year my wife and I are discussing how to rebuild it, "for sure this year!" But for now, I needed a dehumidifier. It's a good reminder that every sale has three stages -- and that's true for up-selling as well. Stage 1: Do I really need … Continue reading Sales — Do you know what stage you’re in?
[Disclaimer 1: This is not a primer on Brexit -- google it.] [Disclaimer 2: I'm not a lawyer, consult your own!] GDPR and Brexit The GDPR came into force on May 25th, 2018, and is applicable in the UK. It is implemented through the UK Data Protection Act 2018 (short: "DPA") and will remain applicable … Continue reading EU / UK / U.S. Data Transfers after Brexit.
Minimum valuations and their required revenue at fixed value-creation-multiple of cash consumption. In the last blog post I wrote about Fred Wilson's excellent insight into value creation relative to cash burn. I got a lot of questions about it so here is an Excel spreadsheet for you to download and play with -- let me … Continue reading Fred Wilson’s “Return on Burn” (Excel Worksheet Attached)
I recently got some questions from first-time founders on dilution, what is a typical A round, what does a typical cap table look like (not the format, but the progression over time). My answer is always the same: It depends. Here's an Excel worksheet that lets you play around with different round sizes and investors: … Continue reading Cap Table Changes over Time and Founder Dilution (Excel Worksheet Included)
[This post appeared first as a comment on Blue Dot Partners' blog, Perspectives. Philippe Bouissou wrote a post that resonated with me about The Two Types of Businesses. There are two very different types of businesses. The motivations that drive entrepreneurs behind them are quite orthogonal. Both types of businesses are critical to creating a … Continue reading The Flipside of Venture Capital.
