Introducing Paid Subscriptions
First and foremost—Happy New Year! 🎉 Wishing you a healthy, happy, and prosperous 2026 ahead.
This blog started as an creative outlet for me 4 years and 3 months ago at 3:15 in the morning and has become a place to think out loud about technology and startups, AI, strategy, VC and PE funding, and the many other realities associated with tech companies. Over this time, I’ve published 544 blog posts, and it’s been a great experience.
I’ve heard from many of you—founders, operators, builders, investors, and academics—who’ve said the most valuable pieces are the latest trends, the “inside baseball” chatter and news, and the hard-won lessons that rarely fit into short posts.
So today, at the beginning of a new year, I’m introducing paid subscriptions.
You may ask: Why introduce paid subscriptions?”
The answer is that paid subscriptions will make it possible to:
Go deeper on complex topics
Share more inside information
Write more thoughtful pieces
Keep the posts focused on quality - especially when I have to purchase research
This isn’t about putting everything behind a paywall. It’s about creating space for the kind of work that’s most valuable to founders and serious builders.
What stays free
Free subscribers will continue to receive:
Posts on AI, startups, and innovation that have been written in broad strokes
Curated analysis and commentary
Occasional long-form posts that are important to everyone
If you’re here for real-time coverage of industry events and trends, new technologies, and key issues in startups and venture funding—you’re still very welcome.
What paid subscribers get
Paid subscribers will receive:
Industry developments, market maps, and structured thinking you can actually use
Deep dives into AI, data, cybersec, blockchain, open source, and go-to-market strategy
Early access to selected posts
Occasional subscriber-only essays and experiments
Think of it as a shift from trends and news toward deeper ideas, analysis, synthesis, and real operating insights.
An invitation
Lessons has helped shape your thinking, influenced your work, helped you avoid a mistake, or spot a more clearly, a paid subscription supports the work and makes room to explore new thinking, technology and approaches to building and running businesses.
And if now isn’t the right time—that’s completely okay. I’m grateful you’re here.
Thank you for reading, sharing, and engaging. More to come.
And once again, Happy New Year 🎉
-Doug