Bootstrapped Giants

How to Change Your Life: Get a Coach

Published 3 months ago • 5 min read

Last week, I told you how working with a coach enabled me to grow my business, find my true purpose, and even make me a better husband.

Of course, the follow up question on every founder’s mind was:

How do I get RESULTS by working with a coach?

This email answers that question. But before I start, there are two prerequisite questions:

  1. How do you find and select a coach?
  2. What do coaches do?

How do you find and select a coach?

Let’s start there.

The best way to find a coach is to ask around from other founders you know who have very positive things to say about their coaches. If you don’t have other founder friends with recommendations, I’d recommend finding one on The Conscious Leadership Group’s website. Just like any service provider, find 3-5 different coaches at different price points and meet them.

Coaches can range from $1k on the low end to $10k on the high end, per month which usually includes 2-4 sessions, offline support and maybe shadowing or 360 reviews. One issue most bootstrapped founders have is: THIS IS MY OWN MONEY, IS IT REALLY WORTH IT?!

Yes, it is. Trust me. If you pick the right coach and do what I'm about to show you. Try it for 3-6 months and see for yourself. Very low downside with huge upside.

Selecting a coach depends a bit on what you’re looking for. I made this 2x2 matrix when I selected a coach.

If you’re a younger founder and a first-time CEO, I suggest going a bit cheaper and more towards a business-oriented coach (they'll help you delegate, org, think about strategy) and maybe in between on the experienced founder vs professional coach front. Because…

If you’re more experienced, go towards someone who is experienced but more “spiritually” focused (meaning more helping you grow yourself, face your demons, etc. vs. giving you business advice). Because…

My coach, Dave Kashen, started me between spirituality and biz. He taught me a ton about running meetings, feedback, etc. He even ran Ampush’s offsites to help my team.

Over time we shifted right on this matrix toward more spiritual growth than business help. He’d started companies before becoming a coach and that experience was important to me.

Critically, the x-factor of CHEMISTRY is super super important. Do you like this person, do they fit your style, do you see yourself being vulnerable with them? That is very important. If they look right on paper, but you don't feel the chemistry, don't force it. Keep looking.

Ok, so you selected a coach. What does a coach DO exactly?

I’ve found at least 4 major things:

1) Self-awareness - Coaches act as a mirror to you to help you build self-awareness. When I first started coaching, Dave was like “You use the words SHOULD, MUST, NEED a lot… do those feel like energizing/inspiring words to you?” I had never noticed that. It was a small change but changed my communication with my team and my wife! "Should" got replaced with "Like to.: I’d LIKE to BEAT this year's revenue target is so much more inspiring than I SHOULD beat this year's revenue target. That’s a tiny example but a coach will notice and share back patterns across how you work with people, what you stress about, etc. It is an amazing resource.

2) Accountability Partner - As a Founder/CEO (especially bootstrapped), there really isn’t anyone in your life to help you with your “TO DOs.” If you’re like me, you have a million things either in your head or on random lists you want to do. Some dates, maybe. But they never get done. At the end of most coaching sessions, you will say “I want to do xyz” and the coach will say: OK great, by when? Then write it down and help hold you to it.

3) Teacher - A good coach has lots of clients, sees a lot of things, and reads a lot. They are usually personal growth-focused themselves. So they bring a TON of frameworks, examples, dot connections, and its hugely valuable to grow as a leader. I’d guess close to HALF of what I share came from Dave teaching it to me.

4) Therapist - They are the only person in your life you can share ANYTHING with and there are no judgments. Co-founder issues, family issues, personal stuff… whatever. Sometimes it's just great to have a place to share those things. They are typically amazing listeners and question askers and that is so valuable to process the insane journey of building a company.

One FAQ I often get is what’s the difference between Therapist and Coach? I’ve never done therapy but my understanding is that Therapy tends to be more backward-looking with a focus on understanding. Coaching is forward-looking with a focus on action.

That brings up a potential 5th thing: “Vision enabler” - Coaches often start with “so what is your dream in 1 year?” and really help you do all the things to accomplish that vision.

OK, so we know how to select a coach and what a coach does. HOW do you get the most out of your experience?

Here are my tips:

1) Take Responsibility. A coach is there to Support - This is the one I see many people get wrong. They walk into a coaching session, don’t have much to ask or share, and then feel like there isn’t much value to coaching. Coaches are taught to MEET you where you are and SUPPORT you. So if you don’t have items you want to work on or goals to achieve, the coach isn’t going to tell you what to do. (THEY ARE NOT AN ADVISOR.) So be prepared with a few items, have a vision for yourself and YOU drive the sessions. Even upfront, know what you want to get out of coaching. My early topics were to be a better leader and have less emotional ups/downs.

2) Be Vulnerable/Candid - Another classic mistake. You pay someone a ton of money and then you hold back 50% of your truth, your thoughts, etc because you’re afraid they’ll judge you. Then you get little value. Of course, it takes time to build trust with someone but push yourself to share as much as you can and get 20% out of your comfort zone. If not, it's like going to a Golf Pro and being like “Sorry I don’t want to swing in front of you” - they just can’t help.

3) Commit to it - I mean this in multiple ways. Do it for AT LEAST 6 months. Pay upfront if you don’t like the meter running. Don’t reschedule, this is your time to invest in you. And talk to your coach between sessions, communicate with them, explain the business, and bring them along. Make them part of your workflow.

4) Do the work - that relates to committing and it shows up in 2 primary forms: 1) Read the books, videos, etc that your coach suggests. If you don’t educate yourself, you won’t actually internalize how this works. And 2) When you say you will do something, do it. Tough conversations, waking up at a certain time, no longer criticizing your team. whatever it is. Do the work.

5) Increase weight and reps - like weightlifting, if you don’t keep ticking up on the amount of weight and reps, you won’t grow. What that means is as you get your first few things solved, take on bigger and different challenges. Push yourself and your coach to help you get to the next level.

So there you have it. A practical guide to using coaches.

If you’ve had a coach, tell me something I missed and I’ll share it with the whole community.

Have a great week everyone!


Bootstrapped Giants

Jesse Pujji

Bootstrapped to an 8 figure exit @ampush. Now building a $1B+ bootstrapped venture studio @GatewayX and sharing everything I learn along the way.

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