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“Founder Mode” Is a Dangerous Red Herring

Love the conversation. Disagree with the implied conclusion. I won’t summarize Paul Graham’s essay on founder vs. manager... Read more

R.O.S. Return on Safety

When do employees share opinions freely? When do they call attention to system frailties? When do they jump... Read more

You Might Want to Sit This One Out

In 2022, a massive correction began in the startup ecosystem. Rising interest rates led to plummeting startup valuations... Read more

How to Raise Early-Stage Capital in Any Market

Raising early-stage capital is easy, right? It must be. It seems virtually every other tech-related article to grace my screen... Read more

Management Debt Series: Learn How To Deliver Feedback

It's been said time and again that people don't quit jobs; they quit managers. And why do they... Read more

From Founder / CEO Client To General Partner, Why I’m Joining Enjoy The Work

In early 2017, I was feeling pretty on top of the world. I had left my role as... Read more

Management Debt Series: Learn How To Run a @#$#@ Meeting

There are two separate paths to startup success. The first and far more celebrated path is the one... Read more

Does Everyone Know What We’re Supposed To Do Next? An Introduction To Internal Communications For Startup Founders.

When you start a company, your job is to sell a vision. Then you have to go build... Read more

How to Raise an Inside Round. And How To Know if You Should.

Since 2015, the General Partners at Enjoy The Work (ETW) have advised the founders of more than 125... Read more

Navigating the storm: A startup founder’s guide to layoffs.

Founders spend so much energy on hiring. They read about it. They practice. They build rituals. They do... Read more

A Financial Plan You’ll Actually Use

Since 2015, the General Partners at Enjoy The Work (ETW) have advised the founders of more than 125... Read more

There Is Life After Being a Founder — I’m Joining Enjoy The Work!

I identify as an entrepreneur. I’ve been in the startup world since the 1990s, have started three very... Read more

Raising Series B: Forget Everything You Think You Learned From Your Earlier Raises. It’s Time to Think Like a Banker

Since 2015, Enjoy The Work (ETW) has guided more than 300 separate transactions, ranging from $1M seed rounds... Read more

Management Debt – The Perilous Cost Of Not Knowing How To Run A Larger Org

I have a neighbor. Name is George. Marine veteran. Early 70s. Built like a mountain carved down into... Read more

From Founder to Master Operator

How it started: In 2015 I became obsessed with a simple question: How do founders get better at... Read more