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Leadership lessons from 30 years of building and coaching.
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How to Write a Company Manifesto
And Why Every Founder Needs One. Includes a template for you to use.
The CEO Loneliness Problem
The CEO role is structurally isolating. Here's why it happens, and what actually helps.
Culture Doesn’t Just Happen. You Must Build It.
If you don't, you're building a bad one....
The Friday Update Template Every CEO Should Steal
A practical CEO weekly update template with real examples, the full structure, and how to make it a leadership habit.
Should you rethink everything?
Why you should question...everything.
You Need to Try Claude Code
... or why "I'm not technical" is no longer an excuse.
It’s January and You Still Don’t Have a Plan?
You don't need a consultant. You need the right questions. A simple framework for founders stuck on strategy.
What Founders Get Wrong About Traction
Founders chase "traction" but don't know what it means. This breaks it down into 5 clear rungs of evidence that actually matter. Growth hide
Clarity is a Two-Way Street
You think you're being clear. Your team thinks they're hearing you. You're both wrong. Why clarity breaks down in both directions, and how to fix it.
How to Stop Reacting and Start Responding
or… why you shouldn't reply "F YOU!"
Consensus Kills
Who Owns This Decision? Why Speed, Clarity, and Accountability Beat Consensus Every Time. A decision making framework for start-ups.
The Case for Daily Stand-Ups (Yes, I Mean You)
A ten-minute daily stand-up with your leadership team builds clarity, focus, and urgency. Here’s why I learned to love them.
Clarity First
Everything starts with clarity. As a CEO, your job is to remove doubt--about goals, expectations, and what success looks like. Clarity. Clarity. Clari
You Fucked Up, Now What?
A simple framework to fix when you mess up. Everyone makes mistakes, but not everyone knows how to recover from them. Mark Josephson shares a simple,
The Dangers of Autopilot
A story about a deli’s “Acai bowls” sign becomes a lesson for CEOs on the dangers of leading on autopilot. Learn how to spot when you’re going through
How to Make Your To Do List
Learn how CEOs can cut through overwhelm and set clear priorities each week. This simple system--Now, Next, Later, Always--connects to the Friday Upda
More! Faster! Now! Forever?
What used to look like micromanagement might be the CEO's operating system for the AI era.
Why You Should Send Friday Updates
A practical guide to writing effective Friday updates as a CEO -- how to build trust, align your team and investors, and create a rhythm of clarity, a
How to Have Hard Conversations
Avoiding hard conversations is easy, until it blows up. Here’s a simple 4-step framework I use with execs to make those moments clear, honest, and hum
Brad Feld’s Give First and the Long Game of Generosity
Brad Feld’s book Give First is about mentorship, but it’s really about something broader.
SaaS Math Doesn’t Work in an AI world
or "don't hate the player, hate the game....because it has changed."
When CEOs Should Be Involved
The First Ten and Last Ten framework from HelpScout’s Nick Francis is a smarter way to align teams, build great product, and avoid last-minute chaos.
What Do You Need From Me?
Lack of clarity kills momentum. This 4-question tool can fix it. RealTalk™ for CEOs, co-founders, and teams who need to get aligned fast.
Tapas for One
What we can learn from Clara Ma’s sabbatical, burnout, and business breakthrough.
You Don't Have to Pretend to Be "The CEO"
or "the armor we put on for other people." Authentic leadership starts with dropping the act. Reflections from a three-time CEO and executi
When Losing Your Voice Leads to Finding Your Purpose
Rap legend The D.O.C. shared his rise, crash, and new mission at the 2025 Yale Ventures Summit. New album and documentary arrive in 2026
Getting Back to It
Back to it after a busy graduation weekend. Lots on the plate and more on my mind. How do you organize your work?
Double Opt In Warm Intro
How to write a forwardable intro request note
Free Workshop: Prompt Engineering for Humans
Why do we speak more clearly to AI than we do to our teams? We'll discuss what makes a good prompt for people and how it translates = to being a bett
How to Interview a CFO
Hiring a CFO at your venture-backed startup? You don’t need creative--you need correct. Here’s how to interview a CFO who can do the job and help buil
Prompt Engineering for People
Why your team keeps missing the mark--and how better prompts (yes, like AI) can help you lead with clarity and finally get the results you want.
Build It. Nail It. Scale It.
A practical framework for startup CEOs to get clarity, align their team, and focus on what matters most. Build It. Nail It. Scale It.
Build the Model. Do the Work. Know the Business.
SaaS CEOs: Stop guessing. Map every step of your funnel to build a model that drives clarity, leverage, and execution--even if it’s wrong on day one.
Find Your Simple Math
Learn how CEOs simplify complexity by finding their core business equation. Track what matters, align teams, and focus on high-leverage startup metric
How to Interview a CTO
Hiring your first (or next) CTO? Don’t just hope you got it right. Here’s how to interview technical leaders--even if you don’t write code yourself.
How to Interview a Product Leader
How to interview a Head of Product or CPO: discover if they’re a builder, operator, or strategist--and hire the right product leader for your startup
How to Write a Job Description for a Senior Exec
How to write a clear, effective job description for a senior exec. Help your next VP or CxO know what success looks like--and why they should join you
Set Goals You Can Fail At
The best goals are the ones you can fail at. Why falsifiable, specific goals drive real progress--for individuals, teams, and CEOs alike.
What It Really Takes to Bet the Company
What CEOs can learn from HelpScout’s shift to usage-based pricing--how to do the work, build confidence, and make bold, high-stakes changes.
Welcome to How to CEO
A practical guide for tech and venture-backed CEOs on hiring, managing, and running every function--from product and sales to finance, HR, and perform
Your career is not a suicide pact
or "You're going to Hollywood! Damn."
Fear Lives in the Unknown. Replace It with a Plan.
or, "Worry less, work more"
When You’re No Longer Who You Were
After selling his company, Nick Gould faced an unexpected question: who am I without the job? A powerful story of reinvention, purpose, and leadership
Shitty First Drafts: The Secret to Getting Unstuck
or "How I Learned to Love the Worst Draft"
Trust Your Spidey Sense
…or, stop gaslighting yourself.
How to Create Real Urgency Without Causing Chaos
or "GO! GO! GO! vs. 'Slow is smooth, smooth is fast!'
Repeat. It’s the CEO’s Job. Repeat.
or "How to get and stay on centerline."
3 is My Magic Number
or "What I learned from De La Soul"
The Power of Mentalization in Leadership: Stepping Into Someone Else’s Shoes
Enhance your leadership with mentalization--build trust, improve communication, and foster collaboration by understanding others’ thoughts and needs.
Winning Isn't The Goal in Cofounder Negotiations
Or, What I Learned Teaching for a Day at Harvard Business School
Kicking the Can: The Cost of Avoiding Hard Conversations
Or, just do it.
It's the Feelings, Stupid!
Or, 🎶 "whoa, whoa, whoa, feelings!"🎶
From Gut Punch to Exit
or "Do You know how to skate?"
The Truth About the Best Talent
Why Clarity & RealTalk™ Matter
You suck AND you rock!
Leadership lessons from Bruce Springsteen
Happiness is a Well-Fed CEO
How to Build a Healthy Data Diet
Why Your First Move in a Crisis Should Be Nothing
What I Learned from Aziz Hasan’s First Day as CEO of Kickstarter
Burn the Boats: Why You Need to Go All In
Or "How an actual elevator pitch changed everything!" 🛗🔥
Take that Call
Should You Take the Leap? Lessons from My Critical Moments Conversation with Michelle Benfer
Embrace Resilience
The Unpredictable Path of Entrepreneurship.
How to Fail: A Masterclass
What you can learn from Sci-Fi Foods’ “graceful exit."
Relationships Matter
What if your boss told you "You're not well-liked!"
Wouldn’t It Be Great if…
Building a start-up is a never-ending sprint for growth.
RealTalk™: The Gift of Honest Communication
Have that hard conversation. Your team will thank you.
Rituals: One Way to Find Balance
Your job, Your family, yourself, pick any two.
How Can I Help?
Why I love coaching and how I approach it.
5 Slides to Clarity: Simplify Complex Business Challenges
Manage up and down and get better results, with this simple framework