Well, thanks so much for having me, obviously, a huge fan of yours and what you're building at Practice. I know it's going to help a lot of coaches get started and thrive.
First and foremost, it's funny that you use the word trajectory because that creates this image of like moving up — into a certain direction. And I feel like my path has not been a smooth trajectory, per se.
There's been some fits and starts. And we can get into that.
As for a bit about what I’ve done — I spent the first decade of my career as an operator at companies like Microsoft and the New England Patriots. Then, I spent the better part of the last decade as a partner at some of the top VC firms in New York City.
About four years ago, for a whole bunch of reasons, I decided to become a coach.
I've built a small thriving practice which I've been doing full time for over two years now.
And I Iove it, this is my life's work.
I would say, look, it's gonna take time to build a practice.
In fact, if you truly want to be a coach — start on the side.
It is such an amazing side hustle business. You can get started and keep your job and you can coach our nights and weekends.
For me, I coached like that for over two years before I had the confidence to go out on my own.
A few weeks ago, I looked at a financial model that I created when I was still investing. And I've surpassed all those projections far easier than I thought I was going to, but it took me two years of doing this on nights and weekends, going through three or four different trainings and getting my ICF certification — before I really had the confidence to step out on my own.
So I would say those that are looking to start a practice, just get started.
Listen to yourself and look within. And if this is truly what you love to do and you feel like it's your calling, just keep on going.
My first training was with an organization called Leadership That Works.
Their program was called Coaching for Transformation, and it's one of these nine month ICF certifications.
But there are so many amazing resources at our disposal now that you don't have to invest five to $10,000 on going through a training.
Jerry Colonna once said to me there are 84,000 doors to the Dharma — the point is just to choose one don't obsess over picking the right one.
You can start on your own and just see where it ultimately leads you.
There are certain organizations that piecemeal their training. So, for example, there's an organization called Coaches Rising. I'm a really big fan of their online trainings.
They tend to run from $500-$600. They’re not cheap, but they are more accessible. So that's also a great place to start, with some of these new, online training organizations.
Well, I would say first and foremost, there are a lot of people in the world with very little training or no training whatsoever and hang up a shingle and say, they’re a coach. And there are probably some that are very good.
So, I think the person that determines who's who's a coach is yourself.
A month before I started my first training, I was in Boston and I emailed this coach. Who's a 20-year veteran. Former entrepreneur, he's been coaching for over 20 years — gray hair.
He'd been one of the people I had talked to for almost a year before I finally decided to take the plunge and I'll never forget our conversation.
I said to him, “In three weeks when I start my coaching training...” and he's like, “Steve, you’re already are a coach.”
And that shifted my mindset.
I was like, “You know what? I am a coach.”
And then the first weekend of my training, I remember coming home to my wife on Saturday night and being like, “Hey, I really liked this.”
I didn’t know what I was doing, but I kind of instinctively knew what I was doing. Largely because I had already been working with entrepreneurs and helping people.
It's a long way to say, I don't think you're a coach until you believe that you are one.
Well, I should say when I first started coaching, I was coaching friends. And anyone who was coming to me. In fact, my first client was a former camper of mine.
They reached out randomly and asked, “Will you mentor me?”
And I said, “Well, I just kicked off this coaching training. Here's what coaching is and how it's different from mentoring. If this sounds interesting to you, I'd love to work together”
And that’s how it slowly built.
I said to him, “I'm going to make you pay me. I don't want your money, but hear me out. I want you to pay me just enough where you feel like it's an investment in yourself, but not so much that you're going to resent it.”
So you feel like you're making an investment.
Fast forward to today, at any given time, I only work with about 12 clients.
And when I have discovery conversations with new clients, I'm very upfront where I basically give my beginning spiel,
“Okay, there are three things.”
“First is, this is a confidential conversation.”
“Second is, I've seen a lot. It doesn't mean that I'm not going to challenge you, but I'm here with an open heart and I'm going to hold whatever you bring forth.”
“And third, I don't view this as a sales process. I view this as a fit process and the fit is mutual because this is a co-creation.”
“I view this as symbiotic. We're going to grow and learn together. And unless we're both really excited, then it's not worth moving forward.”
And I even say to them, “Listen, I want you to find the best fit possible. So if I can even introduce you to other coaches, I would be honored.”
For me, I want to make sure they end up with a coach they love, and I want to make sure that I end up with clients that I love. And so if it's a fit, great, if not, I'm not attached to it.
A lot of my relationships have been more than 18 months, I have a very low term rate and what I say at the beginning is — I'm not going to lock you into any long-term contracts.
I don't sell packages. I have a standard monthly rate for clients like you. And let's both make an energetic commitment that we're going to do this for a minimum of three months. If it’s working, let's keep on going and if not, let's break. And if something comes up between when we kick off in the three months mark, that's okay too.
I'm really trying to show up in a way where I want this to work for both sides.
I've been working with a range of people from creators to founders, to entrepreneurs, but I don't always have the startup experience or CEO experience to help them as leaders.
I think it's a very personal question because I coach a lot of CEOs and I've never been a CEO myself. I'm a small business owner. I've run a number of small businesses, but never a scaling company.
There is some imposter syndrome that I've experienced related to that.
I would say, feel into who gives you energy.
You might not have all the experience, but if your coaching is something that those in that position are valuing and you're getting great outcomes — then that’s all that matters!
I think there are plenty of great coaches that I work with that have never been CEOs. But they work hard and they do their homework and they study.
I think what matters to a CEO is someone that they feel that they can be like they can trust and that they can grow alongside.
Legal is the least exciting part of a coaching business. But it's important.
We worked with our lawyers to create coaching contract templates, free for any coach to use. Plus, a couple of sample agreements.
Let us know where to send it: