Looking Back at Lessons’ Top Posts & Writing in 2025
First and foremost: Thank you, readers, for another great year!
With this post, in total Lessons published 542 posts by the end of 2025, and its readership expanded meaningfully and at an accelerating pace over the course of this year, reflecting increased growing resonance with the audience.
In this post, I’ll review the year’s rankings of posts and highlight the key themes and signals that emerged across the blog—what resonated most, and what it reveals about where technology, markets, and builders are headed.
Post Rankings
Borrowing from Spotify’s playbook, here are the Top 5 most-read Lessons from the past year:
🥇 #1 — The Status of Blockchain 2025
🥈 #2 — Unpacking RSA
🥉 #3 — The State of Bitcoin Adoption in the Enterprise
🎶 #4 — From SEO to AEO to GEO: Optimizing for the GenAI Era
🎧 #5 — Ethical AI Principles
In the Top 25 posts, the topics clustered around: AI with 9 posts, followed by startup and founder themes with 6, VC with 5, and Bitcoin with 2 – with some overlaps. This distribution reflects a strong emphasis on AI-driven change, builder realities, and shifting capital and finance dynamics.
For most of the year these posts ran exclusively on Substack (I discontinued Medium mid-year). Since then, Lessons has grown to 2,200+ email subscribers and expanded its reach to over 25,000 views per post across social platforms, with LinkedIn as a significant distribution vehicle.
I’ve learned that these post rankings reflect a mix of factors: the availability and interests of the Lessons’ audience, my choice of topics, the day and time a post is published, how widely it’s shared by readers, friends, and family, and—inevitably—the beautiful (not fully transparent) mechanics of both Google and Substack.
Key Themes and Signals
In 2025, taken together, the five key themes of Lessons were:
How AI actually works—such as, agents, models, infrastructure, security, and ethics—and how these systems manifest in real products and workflows, from developer tools and search to autonomous systems, alongside a growing glut of low-value applications.
VC and PE investment trends—and exit markets—are navigating a liquidity reset: capital is constrained, conviction is cautious, and firms are rethinking how value is created, defended, and financed in an AI-first era.
A view of the cybersecurity landscape—how the technology is evolving, where the market is moving, and what trends matter most.
Blockchain and Bitcoin valuation, markets and defi have similarly entered a more sober phase, with emphasis on enterprise adoption and post-speculation utility.
Founders and operators sit at the center of this tension, balancing customer discovery, sales leadership, strategic tradeoffs, and the emotional realities of building, while classic strategy frameworks are being reworked for AI-driven competition.
All of this is unfolding within broader institutional and political currents, where trust, governance, and power increasingly shape how innovation is perceived, funded, and allowed to progress.
Notes from the Author
Several posts that did not appear in the readers’ Top 25 nonetheless stand out to me as some of my strongest work of 2025. While they attracted less immediate engagement, they most clearly reflect the timeliness, depth of analysis, and originality I aim to bring to my writing.
In that sense, the following posts represent my personal benchmark for the year’s work:
When Worlds Collide: Bridging the AI Culture Divide — this one arose out of the realization that AI runs on models; companies—including AI-driven ones—run on culture.
What AI Researchers Actually Do Inside Silicon Valley Companies — published in December with great input from friends. This turned out to be especially insightful for both investors and those in tech.
Trump’s Revenge Against Harvard is Anti-MAGA — published in late May, this one calls it plainly. The deliberate actions that has harmed a great institution and the big beautiful response of a great President of Harvard.
The Liquidity Trap: What’s Broken in Venture and Angel Investing Today — published in early May. This one was prescient.
What Does It Mean to Be a Startup Operator? Published December 16th. I really believe the concluding comment: In the end, being a startup operator isn’t a title or a phase. It’s a way of life.
Conclusion: This post is a reminder that I write for the joy of it, not for the clicks. The blog reflects what I consider my life’s work—working with startups, confronting the hard realities of entrepreneurship, solving real business problems, and engaging in the issues shaping technology, finance, and the lives of founders.
Thanks, I always enjoy your writing. I didn’t realize you had been doing it for a long time on medium! Thank you for doing it, I know it’s a lot of work to keep churning out good stuff!