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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

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

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

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

Time To Armor Up — A New Era Of Fundraising Is Upon Us

We guide a lot of fundraises. And we see them across a wide spread of geographies, domains, and... Read more

All-In or All-Out

Let me know if this scenario sounds familiar. You’ve hired someone, ramped them, and set them loose. While... Read more

Working With Vs. Working For — A Musing on How Language Shapes a Company’s Culture

To “work with” or to “work for”? That is the question. Or at least, it’s the question I’ve... Read more

Do → Manage → Coach

In the early startup days, life is a blur. You’re involved in everything. You’re doing everything. You’re building... Read more

Return vs. Remote

There are party lines being drawn. Each side is fiercely self-righteous. Their arguments are persuasive and well-considered. The... Read more

Good vs. Bad Board Members

And How to Vet Them Appropriately A productive board of directors is a beautiful thing. It’s an accelerant.... Read more

Glass Jaw Syndrome

There are so many diseases that afflict the young startup. I’ve written about many of them before: Frantic... Read more

Multiple Personalities

Meet Randall. Randall joined your startup early. He’s been with you for years. He’s been dependable and effective.... Read more

Habits vs Rituals

Does your company have habits or rituals? Habit: a settled or regular tendency or practice, especially one that... Read more