Writing

Notes from the Edge

A weekly newsletter on strategy, funding, and what I'm learning from the work — written from every side of the table: founder, investor, and operator. New essays land here first.

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2026

Other Side of the Table · Part IV

Part IV: Nobody Believes Your Forecast

I met a founder friend for coffee last week, an hour after he came out of an investor meeting.

Other Side of the Table · Part III

Part III: You're Pitching the Wrong Rooms

I recently met a founder I haven't seen in a while.

Other Side of the Table · Part II

Part II: Why Investors Worry About Passionate Founders

I have a weakness. I love passionate founders.

Other Side of the Table · Part I

Part I: You're Fixing the Wrong Thing

A founder I work with forwarded me a rejection email last month.

You're Not Charging Too Much

A founder I work with is about to launch.

What Athens Reminded Me About Tel Aviv

The first founder I talked to at the Panathēnea conference in Athens was building for the shipping industry.

The First Customer Problem

A founder called me a few weeks ago.

The Question I Used to Wait to Ask

I'm three or four sessions into a new advisory engagement.

The Cracks You Can't See Yet

I've been doing some match-making these last couple of weeks.

The Advisory Board Illusion

I got a call last week from a founder in the pet space.

You Don't Have a Moat Yet

A health-tech founder reached out a few weeks ago.

Everything Is Up to You (Except When It Isn't)

A founder I work with sent me a message last week.

To AI or Not to AI

Last week I had a call with a founder building in HR-tech.

What Investors See in Second-Time Founders

And How First-Timers Can Close the Gap

Getting In Isn't the Hard Part

What founders actually need to ask before joining an accelerator

Build Slow, Move Fast

The strategic preparation founders skip - and regret

Building a Board That Actually Helps

What Founders Get Wrong About Boards

Saying No (The hardest word in fundraising)

Two founders I'm working with got a term sheet last week.

Solving the "Distribution vs. Product" Paradox

How Great Startups Actually Find Traction

Why I Stopped Telling Solo Founders to Find Partners

I'm working with two solo founders right now.

2025

Learning Velocity

Last month, a founder I'm mentoring killed a feature 72 hours after shipping it.

The Efficiency Trap

Last week I wrote about founders stuck in the middle - companies with real traction but not enough to raise a Series A in today's funding environment.

When the Next Round Isn't Coming

A pet-tech company in our portfolio raised their seed round in 2022.

What Advice Actually Means

Last week I gave a workshop at a health-tech accelerator.

What Your First Hires Actually Do

I'm helping a client recruit a COO.

Beyond Product-Market Fit: The Four Fits Every Startup Needs

TL;DR: The Critical Framework

What Founders Negotiate

When They Should Be Negotiating Something Else

What to Send Investors (Before They Ask)

I get this question more than almost any other: "Should I send the deck in my first email or wait for them to ask?"

Why Consumer Hardware Needs a Different Playbook

A couple of weeks after I published "The Startup Playbook is Dead", I sat down with founders building a wellness device.

Inside Corporate Innovation

I was sitting in a board meeting for one of our portfolio companies.

Knowing When to Fold

A friend called me last week. Three years into his startup.

The Niche Market Trap

“The market is too small.”

The Generalist's Revenge

The Impossible Elevator Pitch

When the Rules Change

Last week I published a piece here called The Startup Playbook is Dead.

The Startup Playbook Is Dead

Why Everything You Learned About Building Companies Is Now Wrong