Coaching

What we’ll work on, from your org chart to your inner patterns. How it works, what it costs, and why we might not be a fit.

Work with me

Cal Brunell, CEO Everyday Speech

Three times the revenue. Same size team.

Cal Brunell is the co-founder and CEO of Everyday Speech. When we started working together his multimillion dollar company was stuck, and he was wondering if he had what it took to unlock the next level of growth.

Today, Everyday Speech has 3x the revenue with the same number of employees, and Cal has no doubt that he is the one who can take the company to the moon.

Cal Brunell, founder & CEO of Everyday Speech, on the best investment a CEO can make.

The work

Three things we work on, in whatever order your company needs them.

01Operational leverage

Out of the weeds, into the big calls.

The company can only move as fast as you do, because you’re in the middle of every decision. Together we build the culture, the systems, the team, and the AI agents that let it scale without you. Clear owners. Efficient meeting rhythms. Problems solved a level below you. The company gets faster, and your time goes to the few calls only you can make.

02Founder & company psychology

Your psychology is your company’s psychology.

Your patterns are holding your company back, and most run below your awareness. The part of you that needs to be right. The one who sources self-worth from accomplishment, or elegantly avoids the hard conversation. We’ll get to know these parts using tools like IFS and NLP, and then shift them. When you change, the company changes with you.

03Purpose

Build the company you were meant to build.

Most founders are too busy putting out fires to ask what lights them up. Or they’ve hit their number many times over, and each time it doesn’t change much. As you reclaim your space, we reconnect with the human underneath the CEO veneer and bring that into your work. There’s nothing more impactful than a CEO who knows what they’re here to build.

How does it work?

A 1:1 coaching relationship is among the most powerful investments you can make in your development and the growth of your company. Here’s how it works with me.

See the three phases
  1. 01Align on a definition of success

    The first step is to define one or more concrete outcomes for the engagement, along with the objective criteria that will tell us you’ve achieved them.

    Coaching spans both your business and your personal life. The mental patterns we’re working on are almost never contained to a single environment.

  2. 02Inquire, execute, and iterate

    Next we partner on radical self-inquiry, bringing subconscious, limiting patterns into conscious awareness so you can design a more conscious life and business.

    We meet every two weeks for 60–90 minutes. I help you dive deep into the specific structures your mind uses to make meaning, and therefore to drive your behavior. I help you design field work that brings that depth work into your life, and I hold you accountable to becoming who you want to be, doing what you say you’ll do, and getting what you say you want.

    You come prepared with the topic most important to you each session, and you choose consciously what field work to commit to between sessions. When you commit to something, you’re unreasonable about completing it. I’m available between sessions by email, text, or phone.

    Over time, often very quickly and compounding, you’ll notice changes in many areas of your life beyond the one you’re focused on. Our work changes and evolves as you get closer to the outcome you want.

  3. 03Finish, or begin again

    At some point you’ll either achieve your goal or decide you actually want something else. Either one is a chance for us to step back and decide what’s next.

    You may end the engagement happy with the change you’ve made, or realize that on top of the first change you want another, and we realign accordingly.

What kind of changes do people work toward?

Everything from “raise a Series B” and “build a high performing culture” to “find a new type of motivation that doesn’t make me feel miserable” and “transition myself out of company operations and into what’s next.”

See what’s in bounds
  1. 01Business and life together

    There’s no limit to what you can work toward. Founders often come to coaching because of a business objective, but the coaching itself spans business and personal (any divide between the two being made up and unhelpful), and you usually have to progress in one to get results in the other.

  2. 02Important enough to justify the cost

    If your objective is do-whatever-it-takes-to-get-it-done important to you, it’s in bounds. If it’s kinda sorta important, it’s best not to begin. Coaching is challenging enough that if you’re not committed, you’ll find reasons to turn away.

What does it cost?

Coaching costs along three vectors: time, money, and effort.

See time, money, and effort
  1. 01Time

    Two 60–90 minute sessions per month. Beyond that, expect to make your field work a priority. Your work in a given two-week cycle might be as simple as a 30-minute, sweaty conversation, or it could take hours. You choose how much time you spend, with the field work you take on after each session. However, the more time you invest, typically the faster the change.

  2. 02Money

    My coaching is a monthly retainer of $5,000, all inclusive (I also keep a limited number of engagements on a sliding scale for high-potential, early-stage founders, as part of making this work accessible to more leaders). Every relationship is month-to-month and you can cancel at any time. That said, my average engagement runs about 18 months and usually involves a few substantive changes in that time.

    For founders in the CEO seat, most of the time, the company pays for the financial cost of coaching, even when the coaching crosses both personal and professional.

  3. 03Effort

    Coaching is challenging, emotional work, that should not be entered into lightly. Even with that warning, most clients are surprised by how challenging and confronting this work can be. I suggest clients leave 30 minutes open after each session for processing.

How do I get the most out of coaching?

I ask for three non-negotiable commitments from every client, which create the container that fuels our work together. I make the same three commitments.

See the three commitments
  1. 01Come prepared

    Before every session, dedicate time to reflecting on what’s most important in your life/business, that deserves to be the focus of our time together. Through this you steer the coaching, which ensures we’re always working on the most important thing.

  2. 02Reveal yourself

    Every human being has a “presentation layer,” the way we consciously or subconsciously present ourselves in non-authentic ways to steer toward outcomes, manage perception, or a thousand other reasons. When you notice you’re presenting, call yourself out and reveal what you’re withholding (as we get to know one another, I’ll call you on this as well). The more we deal with what’s true, rather than our masks, the faster and more effective the process.

  3. 03Be unreasonable about your commitments

    Every session ends with the chance to make one or more commitments to your growth, in the form of field work. They’re all optional, but if you do choose to commit, I ask that you’re unreasonable about completing that commitment. This means you choose your word over your reasons, always. I will support you in maintaining this abnormally high bar, because I’ve seen it is catalytic in getting what you want.

Why you should not work with me

This work fits a specific kind of founder. If any of these sound like you, we’re probably a bad match, and it’s better to know that now.

See the five reasons
  1. 01You want to try coaching and see how it goes

    The work is confronting. If you leave yourself an out, you’ll take the out, and if the goal is only kinda sorta important, you’ll find that out fast. Coaching works when you walk in thinking: “I’m getting this done.”

  2. 02Someone else wants this more than you do

    If your board, your investors, or your co-founder sent you, that’s a fine place to start a conversation and a rough place to start coaching. Coaching works when you’re the one choosing it.

  3. 03You want someone to hand you the answers

    I ask a lot more questions than I answer. When the operating side calls for it, I’ll give you my take straight, but the real work is becoming the person who finds your own answers.

  4. 04You want the company fixed and yourself left alone

    Your psychology is the company’s psychology. If all you want is someone to tell you which company knobs to twiddle, a good business book will be much cheaper.

  5. 05You’re not ready to do the work

    Coaching is 30% about the coach, and 70% about your level of commitment. If you do not have the bravery required to go to places you’ve avoided, and are unwilling to make the time needed for training new skills, this relationship is not for you.

Good news: If I’m the wrong coach for you, I’ll tell you. And I’ve been doing this long enough that I’ll probably be able to refer you to the right one.

If this sounds like the work you want to do, let’s talk.

The first call is a conversation. You tell me what’s going on, I tell you what I see, and we find out together whether there’s something here.

Work with me