Leadership & Coaching

Executive coaching

We coach CEOs, founders, and senior executives one-on-one. Between us, we have spent three decades founding and running companies as CEOs, CTOs, COOs, executives, and operators, so we have sat in the chair you’re in. We work with you on the company, the team, the strategy, the hard decisions, and the rest of your life.

Book with Nick Book with JT

What you work on together.

Vision and values

What you want for yourself and for the company, and how your own values become the company’s mission and culture.

Decisions and focus

Strategy, priorities, hiring and firing, the board. We help you make the call, build a plan, and hold yourself to it.

Leading people

Negotiation, delegation, feedback, conflict, and communication. We role-play the hard conversation with you before you have it.

How you think

It’s hard to see the whole field while you’re playing on it. We help you see how you think, what leads you to act, and what leads you to drag your feet.

Product and technology

We are technologists: product, user and customer experience, design, and engineering. When a decision touches any of it, or what to do about AI, we can go as deep as you need.

The whole person

People come to us for leadership. Then something else creeps in.

I’m so tired. My partner thinks I’m ignoring them. I have no free time. I haven’t seen a friend in months.

We spend most of the time on leadership and the business, and we also work with you on the rest of your life, since that shapes the impact you make at work.

Leaders who let their health, partnerships, friendships, or inner lives erode while they build the company often end up, in their forties or fifties, with a successful business and a life they want to escape.

Performance

Training, sleep, recovery, nutrition, lab work, and the longevity questions that come with a long career. We are both certified personal trainers and long-time experimenters. Plain talk and current research.

Mind

Attention, stress, meditation, mental models, philosophy, and the experience of being a mind that has everything banging around inside it.

Relationships

Partnership, parenting, family of origin, friendship, and the loneliness of the top job. We have run companies together for nearly two decades, so partnership under pressure is a specialty.

Money

Income, equity, wealth, lifestyle, philanthropy, and legacy. Your relationship to money beyond the spreadsheet: what you’ve built, what it’s for, what enough looks like, and what comes after.

Career & identity

Founder identity, exec identity, post-exit identity, the second mountain, and the identity collapse that often follows the outcome you spent ten years chasing.

Meaning

Purpose, mortality, what you’re doing here, and what you want your life to have been when it’s done. We are not in the business of avoiding the big questions.

In practice

We help you build a support team in every city where you spend time, from top physicians and physical therapists to trainers and good sources of food. We pressure-test the plans you already have and ask the second-order questions your other practitioners skip. We also have the conversations with you that you can’t have anywhere else.

Your trainer, your doctor, and your therapist each see one part of your life. We look at all of it at once and help you decide what matters.

Working together

What the coaching looks like week to week.

Sessions run about 50 minutes, weekly or every other week, on the same day and at the same time. Each one starts with the homework from last time. Then you bring whatever matters most that week. You know better than anyone what you need to work on.

Between sessions, you can reach us by text, voice message, or email, and we expect you to.

Every quarter, we step back with you and look at the coaching itself: what has changed, what is working, what isn’t, and what to stop doing.

Engagements run a minimum of six months, and most run for years.

Getting started

How it begins.

  1. Intro session

    A short call to meet each other. You talk about what brought you here and what you want from coaching, and we explain how we work.

  2. Sample session

    A free 50-minute coaching session on something that matters to you. By the end, you both know whether you want to keep going.

  3. Discovery

    A long first session: about three hours remote, or five in person, usually with lunch and an activity. Beforehand you do some pre-work, including the Wheel of Life and a discovery questionnaire. Together you take stock of where you are, decide where you’re going, and agree on how you’ll work together.

  4. Design

    Together we set the cadence, the focus areas, and how we’ll measure progress. Some clients are working through a specific transition. Others are working on the next decade.

What you can expect

We’re not the affirmation-and-manifestation kind of coaches. We believe coaching done well should change the shape of your life, and we work that way. We’re usually the ones willing to say what no one else will.

You can expect honest reflection, a push when you need one, and silence when you need to sit with a question. We follow up and assign homework, and if you blow off your own commitments, we ask why.

What clients say

The reason I chose to work with Nick is simple: he cares deeply. He is someone that truly wants to know the whole person he is working with, not just what they want to do with their lives career-wise, but how that interacts with the other roles we play in life. His superpower is helping you to unlock the answers for yourself. Nothing has done more for my self-confidence than to understand that I actually have answers to my problems. Once you realize that, everything seems possible.

Tech professional · 1:1 coaching client

Some people are bestowed with a bright light and I believe there is responsibility with that brightness: to help others find, facilitate and flip their light on. This is really where I truly believe Nick thrives as a coach.

Actor and filmmaker · 1:1 coaching client

Next step

Meet us.

The best way to find out whether we’re a good fit is to dive right in. The first call is free.

Book with Nick Book with JT