Design the Wave. Don't Just Ride it.
Every pricing model trades growth for stability. The best ones refuse to compromise.
Business Model Logic
Business Modeling, Finance, Valuation, Investing, Operations
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You're Not in a Funk
You are not stuck. You are pointed the wrong direction.
The Difference Between a Line and a Curve
Why software, venture, and a lot of careers are all about to get sorted
The Single Player and the Network
Strava Is the Last Real Social Network.
Getting Hired and Hiring Are Both Broken (and the Fix Is the Same)
AI didn’t break hiring. It dissolved the friction that was hiding how broken it already was.
You’re Not Behind. You’re Early.
Why every powerful new technology takes a generation to become useful, and what to do about it now
Sticks, Stones, and Light Speed
A 250-year arc, and why the safest career path just became the riskiest
How Meetings Got Cheap & What That Cost Us
There was a time when calling a meeting was an act of accountability.
The Focus Spectrum
Not all productivity requires deep focus. Some of it requires the right kind of distraction.
The Compounding Tax
Why awareness is the only edge you have when everything else is compromised
Subprime Collapse 2: The Venture Capital Adventure
How mega-funds and inflated seed caps are recreating the 2007 housing crisis in Silicon Valley.
The Art of Narrative Control: Why Founders Must “Massage the Numbers”
How the leverage of financial translation evolved from bloated banking teams to a single founder armed with AI
The Early-Stage Team You Need: Athlete + Advisor
You need C-suite strategy, but can only afford junior execution. Here is how to fix the gap without blowing your burn rate
The SaaS-pocalypse and AI Margin Inversion
For 20 years, Enterprise SaaS was the greatest business model on earth. Today, the math is breaking. Here is what comes next.
Your Business Model Probably Sucks
Why you need to stop building financial models and start building business models.
The Frameworks You Need to Navigate VCs and Raise Your Next Round
There's more money than ever out there for startups, but it seems harder than ever to get it for the vast majority of founders
Why Startups Fail & Why I Started a Podcast
Successes are unique, failures fit into a handful of categories
Surprising Similarities between Venture Capital and Watches
I have gone deep down the watch rabbit hole recently (Airtable database and all), and naturally I’ve started to ask: do watches and venture capital have more in common than is immediately obvious?
What is NRR and why does it matter?
Taking a step back to take two steps forward: trying to predict the future
Inventing ARR
Sorry Toast, but this just doesn't make sense.