Weekly digest #79
How to love learning again, Breakdown of AI things, The secret to influence
We (Matt and Shray) read hundreds of articles on company building, venture investing, and self-management and curate the best ones into a weekly digest to help founders and operators stay on the top of their game.
Better thinking
Complex systems (1 minute read)
Designing a complex system from the start never works. Layer on simple systems to create something that appears complex is the way to go.
How to love learning again (5 minute read)
We’ve all been absorbed in learning one thing while dreading another, and it turns out the subject isn’t really the problem. Your biology, psychology, and social environment all shape how learning feels. The good news is none of this is fixed. Small experiments with how you learn, rather than what you learn, can completely change your relationship with the process.
A practical breakdown of the AI power situation (10 minute read)
Excellent read if you need to get caught up on all things AI in 10 minutes. All these massive OpenAI deals making headlines come down to one thing, power. AI labs believe scaling up compute makes models smarter, but GPUs are incredibly energy hungry and the US grid wasn’t built for this. Big Tech is now buying nuclear plants and signing deals worth tens of gigawatts because the bottleneck to AI’s is now all about electricity. Spend-galore.
Operational tactics
The best strategy framework (4 minute read)
Strategy is a weird one. Some swear by it, others prefer just doing things. Wherever you sit on the spectrum, having some sort of direction is always good. Here’s a simple three part framework to design a strategy without it becoming work around the actual work. Useful at both the company and personal level.
Lies of churn rates & LTV (8 minute read)
The entire software business model depends on customers sticking around, but most companies are way too optimistic about customer lifespan. Simple churn calculations can hide major problems, especially when high growth masks entire cohorts churning out. Looking at total churn rates might show a 20-year customer life when reality is closer to four. Cohort analysis reveals the truth.
Mental models for building products people will love (90 minute listen)
Stewart Butterfield is the founder of Slack and Flickr, and it seems, mostly retired at this point. Here he shares the product frameworks and leadership principles that most contributed to his success, as well as his thoughts on craft, strategy, and leadership. It’s a refreshing listen, and something I think we need to be reminded of today - take care in what you build.
Refer and we’ll send you our favorite books as a “thank you” for spreading the word.
Venture investing
The Leonis AI 100 (32 minute read)
Leonis Capital analysed a dataset of over 10,000 companies from 2022 to 2025 and identified the top 100 fastest-growing AI-native startups. Team size, sales motion, and revenue velocity look very different from the SaaS playbook. If you’re a founder, this report might serve as a roadmap for building in the AI era and if you’re an investor, the report can help inform pattern recognition and shed light on where value is forming and how to evaluate it.
Venture’s reset and two camps (2 minute read)
Since ZIRP ended, VC has split into two camps. Classic venture purists love Benchmark’s lean partnership model, while crossover players mix incubations, rollups, and public exposure like Thrive. With AI and shrinking headcounts, the pendulum is swinging back to check writers with real track records. Firms want to be lean again, and many investors are getting pushed out or leaving to build.
The Low-Tech Revolution: Why AI Will Transform the Industries Tech Forgot [Markets] (25 minute read)
Investing in AI to disrupt low-tech industries is a winning bet. It’s a rare confluence of technology, capital seeking new homes as SaaS saturates, governments pushing digitisation, and unemployed developers providing low-cost implementation. The winners are sectors with brutal margins and high automation potential. Agriculture, food wholesale, grocery, construction, and trucking are forced-adoption markets creating a multi-billion dollar ARR window within five years.
Career management
The simple secret to Influence (4 minute read)
Great leaders aren’t the loudest voices or the ones proving they’re smartest. They ask insightful questions instead of giving advice, challenge assumptions without condescension, and help you arrive at conclusions yourself. They make you feel smart and empowered. By creating psychological safety, people share more ideas, take more risks, and do their best work. Leaders gain power by making others feel powerful.
The real reason you’re underpaid (it’s not market data) (9 minute read)
Senior executives often command premium compensation through value and influence, not data. This is especially true when benchmarks fail to capture actual worth. Your next decade of earning potential comes down to what you build, what you prove, and whether you have the courage to price that value appropriately. This brief read will help you create a case that makes comparable benchmarks irrelevant.
How to not suck at your job (2 minute read)
Most technology companies would run more effectively and earn more long-term profits if, tomorrow, they humanely fired the majority of their team (eek). They would fire people who cost more than the value they drive. This essay isn’t designed to convince you of the take but hopefully makes you interested in things you can do today to avoid sucking at your job. Read on if you’re a tad bit curious.