Open Coaching: $100,994 in 18 months as a part-time executive coach (3 hours/week)

When I started coaching, I had no idea what to charge, which clients were right for me, which ones were not, and whether I was going to be able to help deliver any results (aka. imposter syndrome).

Now that I’ve learned those lessons, I want to pass them along.

Let’s jump into it 👇🏼‍

Article Contents

• How I started coaching
• What my coaching business looks like today
• How I price my executive coaching
• The different types of executive coaches
• How I run my client sessions
• Lessons learned after 18 months as an executive coach

How I started coaching

The idea of coaching as a profession was available to me from a really young age. My father was a career coach for 40 years, well before coaching was as mainstream as it is today.

After leaving my last company to start Practice, I decided to put up my coaching shingle to help other first-time founders. This also allowed me to be the first customer of our product, giving me first-hand experience of how helpful (or not) it was, as a coach.

Being a first-time CEO for 7 years, plus my dad being a coach of 40 years — it felt like enough credibility for me to say, “Hey, I’m willing to take on one person to try this out”.

So I put it out to my network and on Twitter, and that’s how I got my first couple of clients.

Some of those early clients are still with me today. The power of referrals is unmatched in coaching.

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What it looks like today

As the title of this article suggested, this is what my coaching business looks like today — $100,994.61 USD of revenue, coaching 2-3 hours a week, for 18 months.

Since I have a full-time gig as CEO of Practice, I’ve determined that my ideal client load is 4.

I’ve worked with as many as 6, but it felt too overwhelming and I wasn’t able to deliver at the level that I want to for each client.

With twice-a-month sessions for each client, that makes my coaching about 2.5 hours per week, which totals to ~200 hours of coaching over the last 18 months.

How I price my executive coaching

Like many new executive coaches, I had no idea how much to charge initially.

I guessed and put a number out there to get started. Only when I talked to other executive coaches, did I realize that I was significantly undercharging.

Here’s how my pricing progression went:

Over time, I began to feel a difference when I was working for the $450 vs. $300 client.

It felt like I cared less given the value exchange — which caused a problem.‍

I knew I needed to raise everyone’s rate to the same place.‍

Here’s what I said to my clients:

You got a great deal. I didn’t understand the market yet, but I do now, and we’re going to this new rate.

A few months passed, then we raised our round of funding from a16z and Tony Robbins and I raised prices for the 3rd time to what it is today — $600/hour.

Here’s what I said to do that:

I just raised $10m. To justify me keep doing this, I gotta increase my rate again.

It sounds crazy, but $600/hour puts me in the middle of the pack of the executive/CEO coaches that I know.

• My first CEO coach charged $300/hour.
• I know coaches who charge $500-1,500 per session.
• One coach I know charges $10,000/month as a retainer.
• Sometimes coaches will end up investing in the companies of their coachees. Essentially, coaching can become lead generation for their investment portfolios.

I’ve since learned that pricing is about the cost of the problems that you’re helping your clients solve. For example, what’s the cost of your next fundraising round? Is it worth it to pay $2k in order to raise $5m?

That’s an easy yes.

The different types of executive coaches

Executive coaches fall on a spectrum of what I call left vs. right brain approaches.

Skills vs. feelings.

On the left-brain/skills side, it’s more about “do it for me, because you’ve done it before”. An extreme example of this is a coach who takes over your company for a month to get a real understanding of how they would improve things.

On the right-brain/feelings side, it’s more about “help someone solve their own problems”. An extreme example of this would be a coach who makes you cry every session.

I sit somewhere in the middle-left, fluctuating depending on what’s going on in a client’s world — i.e. if they’re fundraising, I’d move further to the left to help guide them to success because it’s an area that I understand very well, having raised multiple rounds of funding myself.

I like to quote Michael Bungay Stanier on this,

Stay curious for as long as possible before moving to solutions. But solutions and advice are part of your offering, so don’t stay away from that entirely.

How I run my client sessions

All my clients’ sessions are done on the phone, with no video intentionally

This makes it easier for me to focus on the conversation and take notes, without worrying about how I’m visually presenting to my clients.

I also write notes by hand, so there are no typing sounds in the background. Reducing these small distractions allows me to focus more intently on the work I’m doing.

Before a session, I go through notes from the last 3-4 sessions.

Then, each call starts off with a few of the 7 Essential Coaching Questions from Michael Bungay Stanier’s book — The Coaching Habit.

This is a great way to structure client calls, and I’d recommend it to any coach. Questions include:

• What's on your mind?
• And what else?
• What's the real challenge here for you?
• What do you want?
• How can I help?
• If you're saying yes to this, what are you saying no to?
• What was most useful for you?

When I’m working through a specific situation, one of the tools that I like to use is 6 Thinking Hats by Edward de Bono.

It allows you to ask questions and probe about the same issue, in different ways.

When you pair these coaching tools with the power of silence, it can produce tremendous breakthroughs.

Topically, most of my client sessions are helping first-time founders navigate their human relationships:

• Management of team members
• Creating and evolving the culture of their business
• Managing c-suite relationships and conflicts

In specific scenarios (i.e. the middle of fundraising), our calls move further towards the left-brain/skills side of the spectrum — like doing a review of their investor deck, or practicing their pitch live.

🔑 My clients also have a special VIP booking link that they can use to book a call at any time, each call is 30 mins long and counts as a full session. This is most often used in critical periods when the timing is important, like a fundraise.

Lessons learned after 18 months as an executive coach

• Be really specific in who you serve, and only serve those people. There are a couple of reasons I’ve landed on first-time venture-backed founders:
  - There is an urgency for venture-backed founders, one that I’m both familiar with and can connect with.
  - People don’t mind higher coaching costs in venture-backed businesses. People outside of venture are more price sensitive.‍
• Impostor syndrome subsides once you start seeing results.  When one of my clients raised $40m over the course of 10 months — I was like, “Okay, I think I’m providing value to these people.”‍
• The internal struggle as a coach doesn’t stop, even after 200 hours. For example: My client really likes a candidate for an important hire. I have reservations about this candidate. They have more information about this person, but I have more pattern-matching as a CEO — I struggle with how much to push in those scenarios.‍
• You’re going to spend a lot of time with these people. Ideally, you should like/respect them.

I hope this coaching exposé has been insightful and most importantly, helpful. Becoming a coach has been an incredibly fulfilling journey and I’m excited to see where it goes from here.

If you’re a coach (or an aspiring coach) and you're interested in simplifying your coaching business and consolidating the number of tools that you use, we might be able to help.