Should Startup CEOs Have a Business Coach?

Creating Elite Entrepreneurs and High-Performing Founders

Matt Ward
8 min readMar 2, 2020

Growing up, I played sports… lots of them. I loved basketball and soccer, and my dad always coached our teams. It was the best…

At the same time, it didn’t last. I quickly reached a level (and age) where his expertise and knowledge were outclassed by the players he was coaching. I’d reached the ‘ceiling’ of his ability to help.

And we all go through phases like this: both as the player and the coach. We reach a point in our development (be that personal or professional) where we’re not sure where to go next, or what to do. The guitarist can only get so far by ‘winging it.’ The same is true of the startup CEO the VCs want to replace.

From language to lifting, leadership to business strategy, the best of the best surround themselves with winners able to uplevel their abilities.

You aren’t exactly the average of the five people you spend the most time with, but it’s pretty darn close.

So, what’s your average? And what are your goals?

Learning or dying

Life is dynamic. You’re either improving or getting worse. There’s no standing still. And this is especially true in the fast-paced, hectic world of startups and entrepreneurship. When was the last time you had a day to yourself to think, let alone to evaluate yourself as a founder or leader?

What about the direction of the business? That’s a big problem too. Ever driven for hours only to realize you should have asked for directions? And in business, time is money.

We all waste time pursuing things. It is part of experimentation. But often, wisdom is learning and profiting from those that came before you.

“If I have seen further, it is because I stood on the shoulders of giants.” — Isaac Newton

You don’t know what you don’t know…


What are you learning today? What are you hoping to get better at?

Guess what, hope isn’t a strategy…

When was the last time you wrote down your goals, both for yourself and for your business? And what about the last time you revisited those goals…? Oops.

Goals aren’t destinations, but a compass. Your goals show, not where you’d like to go, but the general direction and timeframe. If an IPO’s on your list, that dictates a specific path your company must take to succeed. The same is true if a profitable, self-funded standalone is your endgame. And what about revenue and company size?

All of these are questions every entrepreneur MUST answer. And don’t forget to add a timeframe.

Goals without deadlines are just dreams. And we forget dreams the moment we wake up…

There’s a reason your meditation app tracks streaks… accountability. And as a startup founder or CEO, that can be hard. We can be our own worst enemies.

So, before you continue, an exercise: Grab a piece of paper and a pen. Take five minutes and write down your 1,3, 5 and 10-year goals.

Where do you see yourself professionally? Personally?

Think about this throughout the day and revisit the goals. Are you sure you really want that yacht, that Gulfstream… Once you’re sure, make a sticky note on your computer so you see them every day, and save a picture to the cloud.

Then, a quick calendar event 1, 3, 5 and 10 years from now for a check-in. What do you have to lose, ten minutes? What might you gain?

Get my free 15 Step Growth Guide to Acquire and Retain Customers here — no opt in needed!

When does it make sense to get a coach:

Don’t know what to do next?

Have you done your darndest to grow your business? Are you topped out at $1M, $10M… $100M in revenue? Feel like you’ve hit a brick wall because your team/management/strategy etc… is failing and you don’t know how to fix it.

The most overwhelming thing about cleaning is seeing the whole mess. And that’s your job as a founder, to have an overview of the entire shitshow that is your company. And it is a shitshow… you’re balancing payroll, emails, suppliers, team, product development… you’re wearing too many hats and unable to see the forest from the trees.

That’s where a business coach comes in. When it comes to complex situations (like building a successful business or taking it to the next level), it often takes an unemotional outsider to see the issues and trends we’re all too busy to notice in the busy day-to-day.

Feeling isolated and alone?

Being a CEO sucks. Everyone looks up to you and looks to you for guidance and support. But what happens when things are rough and you have to keep a brave face? What happens when you can’t make payroll, got kicked off Amazon or have to lay off half your team…

There’s no one you can talk to.

Good luck telling an employee… “What do you mean we’re running out of money? Stock options are half my salary…”

And an investor or board member… you might need more funding.

Then there’s EVERYONE else, and they’re always killing it. Meetups are full of founders “just killing it” with things that are “going great.” Everyone is winning. Seems suspicious.

But in our darkest moments, even if you know it’s not just you, it feels like it is. You feel alone and scared, scared of losing the business, losing your baby.

At least that how I did.

That’s where an impartial coach comes in.

Are you overwhelmed?

As a founder, I wore a million hats, working eighty plus hour weeks and dreaming about Amazon. It wasn’t a pretty picture, but it worked… at least for a year. Thing is, if you’re building a serious business (venture-funded or otherwise), it isn’t a one year gig. You can’t afford burnout, you can’t afford failure. You’re in this for the long haul.

And this is one of the hardest things for CEOs to do, to admit they’re failing. It’s hard to manage people, to build systems, to simplify… but it’s also necessary.

“If you’ve got a dream, it requires a team, and if it doesn’t require a team, you’re not dreaming big enough.”

That’s a big part of the reason I got into founder/CEO coaching. I’ve been there, felt the pain, done things all wrong… It almost ruined me and my business.

But there is so much potential in this world, in all of us. Many businesses fail or fail to reach their potential. And oftentimes, that comes down to overwhelm.

The culture, the strategy, the morale, the vision… everything revolves around the CEO. You’re the nexus of creativity and progress. And like a racecar with a crappy motor, no amount of effort and umph are going to outgun a Ferarri V12.

Source: Times of Israel

Need to grow faster?

Growth solves most problems. Sure, it amplifies others (like Facebook), but in general, most businesses are built to scale. Thing is, what got you here won’t get you there.

There’s a big difference between $5M and $25M in sales. Same with 25 and 100, etc etc…

For every level, there’s another devil.

And almost always, the strategy (and often team) need to change to make it work. It’s easy enough to hit $10M a year with a few products, systems and a strong team, but to reach $100M a year, that requires serious management structures, new distribution/sales channels and a whole new way of looking at the business.

You “do things that don’t scale” until you figure it out, and really need to scale. At some point, pitching mom and pops to carry to sugar-free sodas is just a drop in the proverbial bucket… A Whole Foods deal could land you hundreds of stores at once.

The problem many companies face is hamstringing themselves for too long. If you pursue an old model for too long because “it’s working”, without exploring new growth strategies, you’ll forever fight an uphill battle.

And competitors won’t all make the same mistake. Some will. What’s familiar is comfortable. If it ain’t broke… right?

I push founders to constantly be testing new channels and thinking bigger.

Why I became a coach

My background is ecommerce, network effects and growth hacking. I scaled an $8k investment into a 7-figure products business/exit in under 12 months… hence the sleepless nights.

I became a coach to have an exponential impact on the world (also why I started The Disruptors podcast, a long-form TED on the big issues facing all of us).

Working with winners changing the world is the best way I know to improve the world. For you, it is too, hence your company.

But we all struggle from time to time, and could use help to uplevel our skills, strategies and selves. The faster we grow (ourselves), the faster we go, and the more we accomplish. That’s why I ONLY work with leaders and visionaries willing to work hard (on themselves and their businesses) to take their visions to new heights.

It doesn’t take 10x the effort to achieve 10x the results. That’s where I (or any top-notch business coach come in) help founders and CEO expand their potential and reach higher.

If you’re interested in growing your business, without working harder, we should chat. Whether it’s myself or a connection to someone else in my network, if you’re building something awesome for the world, I’d be happy to help.

Learned something? Click the 👏 to say “thanks!” and help others find this article.

Hold down the clap button if you liked the content! It helps me gain exposure .

Clap 50 times and follow me on Twitter: @mattwardio

And if you’re doing something great, getting it out to customers/users is key. Here are a few free resources that might come in handy, in addition to my newsletter.

Go build something incredible!



Matt Ward

Climate Syndicate Lead @ 4WARD.VC | Startup Strategy & Growth Advisor @ | Serial Founder: 3 Exits | Looking to join top Climate/Impact VC Fund

Recommended from Medium


See more recommendations