Buying The Future

It’s no secret that I’m a huge fan of having a coach.

I’ve had one in most phases of my entrepreneurial journey.

But recently, I’ve expanded that to other parts of my life, and today I want to share with you where I’m getting coaching, why, and what it’s provided me in return.

Existing CEO Coach

Just for background, I’ve been working with CEO coach Mike Del Ponte for about a year and a half and he’s great.

Mike has a lot of “range” as a coach. He focuses with me a lot on mindset, limiting beliefs, and strategy.

But he can also get into the weeds and give feedback on a cold email sequence, a pricing change, or team member dynamics.

One thing I realized through starting to do my own coaching, is that the times I’ve been stretched in terms of giving feedback or helping a founder through a situation that I’m not extremely familiar is the realization that:

I’m not the best person to be helping you here.

Sure, there’s a lot of benefit to having a One Stop Shop kinda coach. I think I’m that to a lot of my coaching clients, and Mike has been that to me.

Any question that I have, he’s really well versed to answer it.

But the reality is that I’m not (and Mike would probably say that he’s not) the absolute expert on every subject out there…even within the business realm.

So, I’ve been looking at where I have blind spots or shortcomings both in my business life and outside of it, in my personal life.

And over the past few months I’ve added a few more coaches to my team of experts.

Wellness Coach

This one comes first because without good personal health the rest is a moot point.

It doesn’t matter what our MRR is or how much money I make if I’m not healthy, not able to be present for my wife and kids, and not rocking on into my 80s and 90s.

So, on the recommendation of many of my founder friends I hired a coach through MyBodyTutor.

My coach’s name is Chris, and he’s amazing.

Interestingly, he’s “just up the road” from me in CT, and is just a few years older than me.

What Chris and MyBodyTutor provide me is:

• Accountability: I log everything I eat, how much I sleep, how much water I drink, how much and what types of workouts I do. Everything goes into the app, and Chris provides feedback on it every day.
• Sounding Board: Chris is an ex professional athlete and full time personal/wellness trainer, so he knows his shit. Any kind of food or workout question goes to him and I know that I’m getting the right answer (for me).
• Consistency: Anyone who’s ever tried to lose that last 10 lbs knows that it’s easy to get started, but you eventually get derailed. With someone who’s on your side, as an impartial support member (that is not your spouse), I’m much more likely to stick with any kind of program he comes up with.

Since starting with MBT I’ve lost 6 lbs (i was in pretty good shape already), and am nearing my all time low. 4 lbs left to go as of today.

Outbound Coach

At Castos, we’ve relied on inbound marketing to generate leads and prospects for us kinda forever.

And it’s worked out pretty well.

But, there’s no accelerator petal to step on when it comes to Inbound.

All the moves are slow, trudging along in months and years.

So, to compliment the inbound work we’re doing, I started doing some cold email prospecting.

I quickly saw that I was terrible at it, and found myself struggling with many of the aspects of defining my target audience, writing good emails, managing the aspects of the technical setup of cold email.

I was going to hire an agency to “just do this for me”, but thought that this went in the face of the advice that I give to every founder:

You can’t abdicate the responsibility of growth….you as the founder have to own it, and figure it out. Only then can you hire.

Me, in most every coaching call

And so I went looking for someone to help me with this.

And did I ever get lucky.

I started working with someone who runs a cold email agency (can’t say who, sorry), and am able to pay him a couple hundred dollars an hour for his time.

Here he downloads everything he knows about running cold email to me, and I’m able to then run with it.

In this, I’m literally shortcutting years off of my learning curve, all for a relatively small amount of money.

Still early in our campaigns, but we’re getting solid open rates and conversations are flowing. More than I could’ve said about the same efforts when I was doing it alone.

Sales Coach

What?! I thought Craig was supposed to be “the sales guy”.

Yep, I’m pretty good at it.

But you know what I’m also: Humble.

And Realistic.

I know that I don’t know everything.

I’ve never built a 10 person sales team.

I’ve never scaled to $50M ARR.

I’ve never built a robust pipeline generation system.

And so I went out to find someone who’s done all those things, and hired them to show me how.

This one is a cool double-bonus.

One: I’m becoming a better sales operator for my work at Castos.

I’m designing a better customer journey. I’m doing prospecting better (irrespective of my work with my Outbound Coach). And I’m operationalizing my sales efforts.

Two: I’m able to take the things I’m learning and pass them on to my own coaching clients.

My sales coach works with companies like Amazon, Verizon, and some of the biggest names in tech you’ve definitely heard of.

And I get to pick his brain for an hour every week to dial in my sales process.

Again, all for a couple hundred bucks.

Leveling Myself Up

I know some of you must be yelling at your iPhone now saying, “why don’t you just hire for these roles?!”.

And I hear you, to some extent.

But for one, nobody can make me healthy, I gotta put in the work (mentally and physically). So that’s all on me.

On the work front, I think that there’s probably not higher ROI move you can make than to invest in yourself.

So the time and money I’m putting in now with each of my coaches are probably going to pay off something like 100x in the next 6 months.

Because as the founder, I’m already the biggest lever in my business. And getting these specific functional-area coaches are just making me a bigger, stronger, and faster lever.

What’s not to love?