2025-W11

Business Strategy & Positioning

Positioning Beats Intelligence
Shane Parrish made this clear in his book “Clear Thinking” – you can be the smartest person with all the right attributes, but if you’re in a bad position, good decisions are nearly impossible. People we consider successful are often just well-positioned, getting easy decision after easy decision. I’ve never quite shaken this insight since hearing it. Andrew Mellon, for example, deliberately positioned himself to be insulated from market crashes.

What Would It Take?
When negotiating, if your first offer gets rejected (or even before making it), ask “what would it take?” I like this approach because it’s open-ended. From “Never Split the Difference,” I learned you get more information with open-ended questions that start with “what” and “how.” These questions yield much richer insights than closed ones.

Finding the Smallest Win
I heard the founder of Lindy AI discuss the importance of breaking problems down to find something that could ship that day – not something that takes days or weeks. Finding the smallest leverage point and iterating to solve progressively larger problems while realizing value quickly seems powerful to me. I’m trying to apply this more in my own project planning.

Format Drives Engagement
The Patreon CEO mentioned how he struggled for seven years with stagnant growth until he experimented with a “song per week” format. People get attached to formats – they know what to expect, with that sweet spot of novelty within stability. We’ve seen this with Tim Ferriss’s “5-Bullet Friday” and our own “Founder Finds” at Trends.vc – having a consistent format creates expectations and loyalty.

Decision Making & Mental Models

Clarity Through Constraints
I’ve been thinking about constraints a lot lately – how they simplify the problem space and make challenges easier to solve. For example, when buying businesses, defining what price or multiple you’ll pay, which markets to avoid, etc. Through constraints, you create razors that cut away noise and complexity. Steph from Obsidian emphasized this, and initially I thought he overstated it, but later I realized constraints weren’t emphasized enough. They create focus.

North Star Metrics Matter
It’s fascinating to see how companies organize around a single goal – Perplexity optimizing for queries per day, Groq focusing on 25 million tokens per second. What interests me is going upstream of revenue. Revenue isn’t a great single metric because there’s something driving it. I want to identify the most upstream possible metric to track and organize around. But the question is always: what’s the counter-metric to ensure we’re not gaming our primary metric?

Trust Your Own Judgment
I used to shift much of my decision-making to “experts” or “models” or people I looked up to. I still get inspiration from them, but I now see these as experiments. If something doesn’t work for me or needs tweaking, I adjust it, even if it looks odd. I’m less concerned about doing something different or counter to conventional wisdom. What matters is: does it work for me?

Opportunity Cost Awareness
When thinking about decisions, considering opportunity cost is crucial. Some people become expert naysayers, identifying risks or downsides to every option. They’re missing the point. Yes, identifying risk is important, but so is recognizing the risk of inaction and delay. I don’t like unnecessary risk, stress, or anxiety – but some risks are necessary. It’s more important to make a move than no move at all.

Process Over Outcomes
I listened to Leila Hormozi discuss frameworks for fast, smart decisions, which reminded me of Annie Duke and Howard Marks. They all emphasize judging decisions by the process, not the outcome. Duke talks about “resulting” – don’t judge a decision based on what happened, but on the quality of thought that went into it. Whether in investing, sports, or business, focusing on developing quality processes matters more than obsessing over individual outcomes.

Pain + Reflection = Progress
Ray Dalio discussed this formula, and it resonates with my approach to courage challenges. These challenges create discomfort and even psychic pain, but I follow them with meditation for reflection. It’s a barbell approach – intense periods of challenge balanced with extremely peaceful periods of meditation. For me, courage challenges are a proxy for pain, meditation is a proxy for reflection, and together they equal progress.

Personal Growth & Mindset

Competition as Necessary, Not Desirable: Similar to suffering, competition isn’t something I seek for its own sake, but to some degree, it’s necessary. I don’t like unnecessary competition just like I don’t like unnecessary risk. A lack of competition can lead to complacency.

No Stasis, Only Growth or Decline
There’s no such thing as staying still – even if you think you’re maintaining position, you’re falling behind due to inflation, competition, or just entropy. Things naturally fall apart. This makes me think about the importance of continuous improvement rather than trying to preserve a static state. You’re either growing or dying.

Technology & AI Reflections

Creativity Shifting to Ideas, Not Execution
Looking at AI tools in the market, the future of creativity appears to be less about execution ability and more about the quality of ideas and narrative. This hit home because when anyone can generate videos, graphics, or prose, the leverage flows to those with quality ideas and stories. Pieter Levels’ flight simulator that reached nearly $1M ARR in revenue quickly exemplifies this – he didn’t know how to build a multiplayer game but used AI for execution. The value came from his idea and narrative quality.

Counter-Positioning in AI
Mike Maples discussed how large companies can be trapped by their incentives – Google invented and published transformers but didn’t act on them. OpenAI had nothing to lose, allowing them to counter-position effectively. Now Google is trying an “all hands on deck” approach, but they’re fighting against their own established incentives. This applies to individuals too – those protecting reputations limit their potential by avoiding the beginner’s mindset or risking embarrassment.

Life Philosophy & Environment

Seek Autotelic Work
David Senra talks about starting businesses that feel natural to your inclinations. I love this approach and it was a key constraint when starting Trends.vc – I wanted something autotelic, something I’d do whether or not there was an audience. His Founders podcast exemplifies this – it’s clearly natural to him. Finding work that feels inevitable rather than forced seems like a sustainable path.

Rich and Anonymous
I heard discussion about being wealthy but anonymous, which resonates deeply with me. I hesitated to do these voice memos or re-establish an online presence because my goal is wealth without public recognition. I’ve experienced micro-fame before – being known by people you respect at conferences is beneficial, but there’s a thin line. Tim Ferriss has a great post on the downsides of fame. For me, fame feels like a violation of independence and peace of mind.

Environment Shapes Behavior
I’m fascinated with how environments shape our behavior – at country, city, neighborhood, and home levels. As a nomad, I’ve seen many different environments and built a mental “swipe file” of features that work for me. Not seeking perfection, but understanding the trade-offs that align with my needs. Having explored the problem space, I feel more equipped to make good decisions when establishing a base.

Tech Boundaries For Sanity
Setting hard boundaries with technology is becoming increasingly important. I’ve used apps like One Sec to delay access to WhatsApp or iMessage, and recently started experimenting with completely blocking access to certain apps. I’m still refining my approach since I’m not disconnecting as effectively as I’d like. Finding the right balance between connectivity and focus remains a work in progress.

Learning & Reflection

Meditation Against Mimesis
I’ve found meditation invaluable as “medicine against mimesis” – especially when on Twitter/X where people get caught in momentary hysteria that doesn’t make sense from first principles. Meditation helps me come back to center and ask “what’s true for me?” without isolating myself completely. It lets me engage with the noise while maintaining the ability to silence it when needed.

Learn Your Own Way
Ray Dalio mentioned learning more from conversations than books, while Charlie Munger emphasizes books. For me recently, it’s been podcasts, though I’m open to deep research being more valuable now with AI models. The key is trusting my personal experience rather than feeling constrained by what works for others. I’ll do what’s true for me rather than following prescriptions from even the most successful people.

Validate First, Build Second
The founder of TypeShare discussed validating ideas before building. While that’s generally sound advice, I’m building tools that solve my own problems first. Even if there’s no market beyond myself, they help me. My voice agent tool already saves me 30 minutes daily – anything beyond that is just gravy. Self-validation can be sufficient for initial development when you’re solving your own problems.

Publish More, See What Works
There’s value in publishing more content to discover what resonates, then doubling down on the winners. It reminds me of the “100 reps” approach – do 100 of something, identify the top 10% that work, and focus there. Having a simple algorithm for reflection and improvement creates a feedback loop that consistently builds on success rather than guessing what might work.

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2025-W10

Mindset & Philosophy

• Independence Over Wealth: Charlie Munger viewed wealth primarily as a means to independence, not as an end in itself. This aligns with what I’ve always talked about with founders in the TransPro community.
• Money Is Storytelling: The further you get separated from hard assets like gold and silver, the more money becomes a story. Makes me think about Yuval Noah Harari’s point that money is just a story we all agree to believe.
• “Genius Has The Fewest Moving Parts”: Charlie Munger’s emphasis on simplicity resonated deeply with me. I remember the first time I heard this a few years ago, and it’s something I want to embody more fully.
• All Models Are Wrong, Some Are Useful: Every model has exceptions and limitations, but some models still provide value. This applies to business models, mental models, and theoretical frameworks.
• All Misery Stems From Dependency: Morgan Housel connected misery and dependency, reinforcing my preference for building businesses without investors. I’m always suspicious of absolutes, but this resonates.

Business Strategy

• Brand-Ethos Misalignment Causes Friction: The name “Trends.vc” has been misleading for the community, as it suggests venture capital while the ethos is about independence and bootstrapping. I’ve considered changing the name several times.
• Single Metrics Can Drive Focus: Perplexity focuses on “queries per day” as their single metric. I’d like to experiment with having a single north star metric for products in my portfolio.

Personal Development

• Set “Failure Goals”: Rather than stopping after success, consider setting goals based on accumulating a certain number of failures, like making 100 failed sales calls. Nir Eyal talked about this, but it reminded me of furniture company founders I heard about 6 years ago.
• Choose Whose Opinions Matter: Instead of wondering what the world would think, create a short list of whose opinions you actually value. You can always find someone who will be critical—draw a short list of people whose opinions you respect.

Risk Management

• A Personal Risk Management Framework Reduces Fear: After analyzing aspects like reversibility, survivability, risks, rewards, and expected outcomes, nebulous fears become concrete and easier to act upon. I bear a lot less anxiety once I’ve addressed these questions.
• Movement And Momentum Matter More Than Finding The Perfect Mountain: Rather than obsessing about climbing the highest mountain (ideal business model), maintain momentum by climbing shorter mountains first. Dharmesh from HubSpot talked about this—the global maximum might feel impossible, so you do nothing.
• “Aggressive Patience” In Investing: During bubbles, maintain some slack in your system (capital) to aggressively pounce on underpriced assets when the bubble bursts. This makes sense for investors, but I’m less sure about the parallel for entrepreneurs.

Team & Culture

• Decentralized Team Planning: I’m thinking about organizing our team differently – giving them an extremely clear long-term vision but letting them determine the next tactical steps. They have the most context being in the weeds, and honestly, it would move planning off my plate and onto theirs.
• Direct Outreach Can Be More Effective Than Audience Building: Even with a large audience, direct outreach (like Loom videos) to ideal customers can be very effective for offerings like masterminds. This was from Greg Isenberg’s podcast.
• Responsiveness Matters In Sales: This creates tension with my established boundaries like deep work time and only doing meetings on Mondays. I’m thinking about how to create my own style of sales that doesn’t interrupt those boundary systems.
• Counter-Metrics Prevent Gaming: All metrics can be gamed, so design counter-metrics by asking “how would you hack this metric with $10M?” Having paired metrics helps control for manipulation.

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2025-W09

Productivity & Learning

• The 100 Reps Principle: Do 100 repetitions of any activity (sales calls, content creation, product iterations), analyze the top 20%, find common factors, then do another 100 focusing on those factors. Alex Hormozi puts this twist on the exercise, and it showed up in a Mr. Beast interview too.
• Change Behavior Before Mind: Changing your behavior is often easier than changing your mind. I’ve seen this firsthand with my habits and using progressive overload. Confidence starts with action, not the other way around. Tim Ferriss said something similar—through evidence, you gain confidence.
• Risk Is For Managing: Risk isn’t something to be avoided, but something to be managed. On the other side of risk is often reward. Howard Marks said something like this.
• Find Your Bottlenecks: Focus on weaknesses (or bottlenecks) for the highest ROI. Consider using your strengths to solve your bottlenecks—I’m great at building systems, so why haven’t I applied that to publishing and personal branding?
• Opportunities Are Rare: Opportunities are rarer than you think. When you recognize one, you may need to accelerate other plans to seize it before the window closes.
• Busyness Destroys Greatness: A busy calendar and a busy mind destroy your ability to do great things. That’s why I put all meetings on Mondays and have other days for deep work.
• Complete Key Tasks Early: Consider completing your most important task by 1 PM each day. It’s become aspirational for me to finish work by 1 PM and have the rest of the day for exercise and relaxation.

Content Creation

• Reduce Mental Effort: Reduce the mental effort required to consume your content. Intelligence is clarity and simplicity, not complexity or bigger words. I go down to the level of syllables when giving feedback on copy.
• Create What You’d Consume: Create content you want to consume. This was a huge unlock for me from Leila Hormozi. I plan to build a checklist before any content goes out, with this as one of the key questions. Build for yourself. Create things you would want to use.
• Trust Over Size: Trust and relationship value matter more than audience size. Alex mentioned an art dealer making $1M in annual sales with just a 1,500-person email list.
• Daniel Priestley on Daily Writing: Writing a tweet a day. I saw a lot of progress when I was publishing a blog post a day.

Personal Development

• Stretch Without Snapping: Push yourself, but not to breaking. This connects to progressive overload—maximum stretch without snapping.
• Start Below Threshold: Using progressive overload means starting below your resistance threshold—like beginning meditation with just 10-30 seconds. Now I meditate for two hours a day. Lower the bar for your goals to reduce activation energy.
• Trust Your Experience: Trust yourself over the opinions of experts. If something doesn’t work for you despite an honest attempt, it’s not true for you, regardless of who recommends it. Like with Naval’s reading is faster than listening claim— It’s true for him not for me.

Health & Fitness

• Compliance Over Optimal: Choose exercises you enjoy—Lane Norton talks about compliance over optimal being better. If you enjoy it, you’ll do it.
• Lactate Benefits: Lactate, contrary to what we’ve been taught, isn’t just a waste product. High-intensity interval training and lactate buildup may improve sleep. This has been a huge step function in my own sleep quality.

Business & Branding

• Personal Brand Value: A big mistake I made was working with a marketing consultant and choosing to build my business around the business brand rather than my personal brand, partly due to valuing privacy. Looking back, this contributed to the decline of the business.
• Monetize Individuality: Create unique content through personal experience. Naval talks about monetizing your individuality. “Escape competition through authenticity.” Be your unique self.
• Media Is Not Free: When people like Gary V talk about social media being “free,” I disagree. You’re spending time, energy, and attention—resources often more valuable than money. Value and cost are multidimensional.
• Small Business, Big Thinking: Running a small business often requires as much work as running a large one, so think big. Naval mentioned this.
• AI Application Value: Harvey AI is proving that the application layer of AI can be valuable.
• Time Deflation: Dan Shipper talks about “time deflation”—as AI tools improve, waiting may make certain tasks much easier in the future. By doing certain things today, you may be wasting effort.

Mindset & Philosophy

• 10,000 Iterations: Naval talks about 10,000 iterations rather than 10,000 hours—it’s about the number of tries, not just time spent.
• Jiu-Jitsu Insights: You can learn more about a person by rolling with them in jiu-jitsu for five minutes than working with them for a month. Morgan Housel made me think of this when he said people reveal their true colors in crises.
• Principles Require Sacrifice: Real principles must cost something. If there’s no trade-off, is it even really a principle? I heard this related to a company resisting Australia’s attempt to outlaw encryption.

Interesting Concepts

• Ad Testing: Steven Bartlett mentioned testing book titles, covers, and concepts through ads before fully committing.
• Luxury Goods Future: Sam Altman expects AGI to reduce prices for many things, but for luxury goods and resources like land, he sees prices increasing.