Even Steve Jobs Had A Coach… You Should Find Yours
Entrepreneurship is a mental game.
After funding over 70 startups at the earliest stages, and running The House Fund for almost six years, I have learned that ensuring strong mental fitness is not only important, but in my opinion a must for founders.
While entrepreneurship is a lonely journey, you don’t have to do it alone. There are seven types of business coaches in the world (read below), and you can find the one who fits what you need best. Even Steve Jobs had a coach... you should find yours.
Coaching & Me
As a Founder/CEO, it can feel isolating carrying the weight of your company and its people on your shoulders. You have to believe you can build the future, through thick and thin, but that doesn’t come without pain. Ben Horowitz captures this masterfully in his poem The Struggle. It can feel like you are the only one in the world that feels this burden.
Personally, I have been working with an executive coach for over three years, and The House Fund wouldn’t be where it is today without the support of various types of coaches since inception. These partners have helped me stay focused, build mental fortitude, pushed me, and helped me push myself, to believe and achieve — especially when the going got tough.
I am not alone in this pursuit to grow as fast as possible. In fact, some of the most successful serial entrepreneurs we work with have coaches and/or therapists, and unsurprisingly, it played a pivotal role in their growth.
Growing up in LA, I heard stories of the epic John Wooden (UCLA) and watched the “Zen Master” Phil Jackson (LA Lakers); two of the greatest coaches in history, who motivated the best teams in the world to achieve greatness. I went on to play and coach youth sports and applied their lessons to motivate my teams.
I recently spent a day with a professional soccer player and saw what coaching looks like for top physical performers. He had a coach beside him in life for each aspect tied to performance, including nutrition and strength. There are similar business parallels in business with coaches and CEOs.
Types of Business Coaches
So how do we apply this to business?
There are different types of coaches, and it is important to consider building your inner circle in a way that works for you.
The Trusted
The first call
There to support you and be a sounding board, with no judgement
Willing to go above and beyond to ensure your success
Someone you trust
This is the role I play, especially with first-time founders
The Brain
Thought partner who helps you navigate your mind, brain, biases, and make better decisions
Often has a background in psychology
Helps the entrepreneur in “the struggle” press forward with a clear mind
This is the type of coach I leverage to help make better investment and operating decisions
My favorite type of coach and perhaps the most underutilized
Example: Torch is a great platform to find your coach
The Tactician
Specializes in teaching specific skills
These could be one or a bucket of the skills required to run a company: management, operations, public speaking, hiring, etc
Best suited for the CEO who is always trying to get better at certain things, who feels confident in themself but uncomfortable with what they don’t know (or aren’t good enough at)
Your classic executive coach
The CEO
CEOs who have successfully built and sold startups, who can share direct experiences on what it takes to be great
I defer founders to The CEO when faced with some key tactical decisions (e.g. how to negotiate this make-or-break enterprise deal)
We love The CEO coach at The House Fund, and have had Part-Time Partners since the beginning — some of Cal’s most successful founders — here to support CEOs
These people are often busy, so leverage them tactically and be willing to find them where they are
The Wise
History has often valued the older for being wiser; These are mentors who have had wealth of experience
This individual need not have directly relevant experience, since they have a toolkit built over decades for navigating decisions, emotions, and life
Someone you can always count on when you need someone to call, like a parent
It is a must to find a mutual click at a personal level
May also have more time to share, as well as more interest in paying it forward
The Peer
CEO who is only 1-2 steps ahead of you
Empathy is a powerful force and feeling
Sometimes their advice is better than The CEO or The Wise because they have been there more recently; It’s possible the game has changed since The CEO or The Wise was in your shoes
This is the value of The House, our startup space. Founders can walk down the hall or bump into other founders at the water cooler to compare notes
The Therapist
Mental Health matters
A Founder/CEO is also a person. Taking care of the full self, personal and professional, is a must
Most founders sacrifice the personal to some extent, and that can affect their quality of life, significant others, physical health, and more
Therapy is stigmatized in society — especially for Founder/CEOs who can be hard headed, thinking if they have a therapist, they are weak
I believe this is one of the most underrated resources in life
What Secret Did Steve, Sheryl, and Eric Have in Common? Bill Campbell, Super Coach.
Some of the most successful and impactful entrepreneurs and executives of our time had a coach, including Steve Jobs, Sheryl Sandberg, and Cal alum Eric Schmidt. Interestingly enough, they all shared the same one — Bill Campbell. His leadership lessons can be read in the popular Trillion Dollar Coach. Prior to coming to Silicon Valley, Bill happened to be a college football coach.
One of our Cal alum advisors who started a unicorn startup was coached by Bill. What was unique about Bill is that he seems to have been a Super Coach; meaning, he encompassed all six of the coaches noted above (the only exception being, he wasn’t a licensed therapist).
While not all of us will find our Bill, we can find something that works for our specific needs. Most professional coaching costs money and it can be, or at least feel, inaccessible (e.g. The Brain, The Tactician, The Therapist). But if you are willing to do the homework, and/or be the entrepreneur you are and negotiate, you can and will find a solution.
Where Coaching Matters Most
For years, The House Fund has been paying for an initial bucket of coaching sessions for our founders in two particular cases: first-time founders and distress.
For first-time founders, we enable faster growth by identifying solvable areas where founders were holding themselves back.
For distress cases, coaching prevents fatal business errors, individual mental breakdowns, and co-founder blowups. Coaching put these same Founder/CEOs on a road to success (or at least closure).
There was one particular case where two founders were in deep disagreement about the direction of the company. The business was at a halt. They had different communication styles and were starting to feel hatred toward one another. Coaching as a mediator helped the founders get to the root issue — a lack of understanding between what the CEO (BD/Sales) and CTO (Software Development) were actually doing on a day to day basis. Trivial! They were able to communicate through it, diffuse the bomb, and get back to work.
Coaching and COVID
My coaches have been instrumental in helping me think through tough situations and continued to do so during this wild, new, quarantined world we live in today.
Mental health and fortitude are all the more important in this world. We are experiencing changes that neither The Wise, nor The Trusted has lived through. It’s going to take some true mental jujitsu to get through these hard times.
It is time to find your coach.
-Fiance
Special shout out to my Dad who coached me in sports growing up and was the first to show me what a good coach looks like. Special congrats to my Mom who recently became a licensed therapist. Special thanks to my coaches — you know who you are!