Coaching — Obvious Startup Advice

July 20, 2026

The Four-Beat Conversation Every Co-Founder Avoids

July 13, 2026

Your Fear Center Is Immune to Logic

July 10, 2026

Don't Lock In the Terms. Go Be Useful.

July 7, 2026

You Haven't Earned Rails Yet

June 24, 2026

Stop Trying to Want It More. Make the Next Step Smaller

June 21, 2026

A Great Month You Can't Explain Is Just a Lucky Month

June 19, 2026

Coaches Don't Deliver Epiphanies, They Deliver the Tenth Repetition

May 26, 2026

Here's Exactly How I Use AI to Write

May 1, 2026

Do Customer Discovery With Zero Goals

January 15, 2026

A Week of Startup Coaching

Coaching

October 15, 2025

Why a Coach Isn't the Same as an Advisor

October 14, 2025

Your LLM Is an Affirmation Machine

September 30, 2025

That Sucks. It Will Get Better.

August 31, 2024

What a Startup Coach Actually Does All Day

Coaching

August 29, 2024

Qualification, Positioning, Proposal: My Sales Playbook

August 28, 2024

How I Doubled My Revenue by Documenting My Sales Process

May 2, 2024

When Advice Works, and When It Doesn't

January 12, 2024

You Can Spot a Fake Expert by Their Lack of Stories

December 15, 2023

How to Get Free Coaching From Experts

August 3, 2022

Assume You Have Ten Good Years Left

August 3, 2022

What Gives Your Life Meaning?

December 9, 2021

The Loneliness of the Long-Distance Solo Founder

December 8, 2021

Go Slow Until You Need to Go Very, Very Fast

November 8, 2021

The Importance Of Admitting You’re Wrong

February 24, 2021

Six Things Every Founder Needs to Know, Part 2

February 17, 2021

Six Things Every Founder Needs to Know, Part 1

Coaching

So you’d like to talk about startups…