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Hey, I’m Jay.
This is where I post my thoughts & Notes on business and other things that I’m thinking about. Enjoy.

How Small Business And Startup Coaches Can Truly Help Small Businesses And Startups

Truthfully, I roll my eyes when someone tells me they’re a business coach.

And I roll them even further back when they say they are a business coach for “small businesses and startups.”

For the moment, let’s look past how incredibly broad and irrelevant that all-too-common title is—we’ll get to that in a second. I want to start by being somewhat unapologetic for everything I’m about to say.

I don’t apologize for hurting your feelings if you are unqualified to be a business coach for small businesses and startups. If you’re qualified, then the only thing that should hurt after reading this is your neck from nodding in agreement.

Actually, I want this perspective to help the newest coaches as well as any other coach trying to help the small business and startup community.

So even if this hurts to read, stick with it. It’ll pay off to you (and the businesses you want to help) if you do.


Here’s the challenge with coaching.

If you’re one of the good coaches you’ve got to understand that you are in an industry with very low barriers to entry.

It’s easy to become a coach. But it’s very difficult to become a great coach.

The majority of coaches that I’ve met are not qualified to coach small businesses and startups. What’s happened is that they feel inspired to share knowledge they think they’ve acquired. That knowledge comes from business books, podcasts, blogs, academia, and other outside sources.

Sometimes they cite their experience as a small business or startup owner themselves.

When they do, they often draw a false equivalency to what they’re doing to what they’re qualified to teach.

Starting your own coaching business and assuming you’re now qualified to coach startups is like taking your driver’s test and assuming you’re qualified to coach a Formula 1 driver.

Not only is it false, it can be irresponsible for you to do so.


Lives are at stake.

This is overdramatic, I know, but maybe not as much as you think.

In startups, peoples’ livelihoods are at stake. The founders might be putting an incredible amount of their livelihood on the line. The employees have something to lose if the startup flops. The startup’s customers are directly affected by the startup’s efficacy, and the investors are also betting their money on the venture’s success.

While there might sometimes be fewer stakeholders involved with a small business, the effects can be amplified in a different way.

In a small business, the business’s success hits closer to home. Instead of paying out investor dividends, their money is paying for their son’s dance lessons or their daughter’s college education. If they don’t make the sale, then they don’t get the perks. It’s not forgiving.

This is the world you’re jumping into when you say that you’re a coach for small businesses and startups.

It’s absolutely not playtime.


Speaking of startups and small businesses, here’s the difference.

A startup has potential to be something very big financially. Small businesses can do very well financially, but the owner may have no desire to become something huge.

Small businesses can become startups.

Crate & Barrel is an example of a small business that became a startup. They went from a single store with no real desire to become massive, to a handful of stores. After a decade of being a small-but-mighty business, they began massive expansion.

Small businesses can “start up,” but that doesn’t make them a startup.

I can “start up” a lemonade stand on the corner, but that doesn’t mean I’m the next Juicero. While “start up” is synonymous with “begin,” it is not synonymous with “startup.” Here’s another way to talk about it. “Starting a small business” is different than “starting a startup.”

There’s a difference between selling Kate Spade bags at a local market on the weekends and actually being Kate Spade.

Now, for the startups.

Startups have potential to be something very big financially. These are things that have the potential to operate “at scale,” meaning they can serve a whole bunch of people at once. There’s often a need for outside money. 

And the biggest distinction is this: Startups can go where small businesses often don’t...the unknown.

The differences are important, especially if you want to be a coach in this industry.

Helping Jimmy come up with the marketing strategy for his boutique clothing store downtown is much different than helping Rachel close in on angel investors for her breakthrough smart home technology. Guiding Ta’Kena through her new point of sales software for her local juicery is not the same as helping Miguel develop his global distribution strategy for vending machines.

There’s no doubt that there’s crossover between small businesses and startups. But there’s also no denying how dramatic the differences can be.


So, what should you do?


Again, there are plenty of similarities between certain aspects of small businesses and startups. But giving improper advice to your clients will harm them and everyone else they’re taking care of. And it won’t just hurt them. It’ll hurt you.

You don’t necessarily have to choose startups OR small businesses, although I think that’s most responsible in most cases.

What I really encourage you to do is figure out an aspect of business that you know very well, then go as deep into the market as you can with that weapon. Alright, what I’m about to say is unbelievably important for your success in this field. Ready?

Ok, here we go: You don’t know everything, and you don’t have to know everything to be a fantastic coach.

A mistake that we all make—whether we’re the coach or the client—is that we think “not knowing” is always a sign of weakness.

Don’t get me wrong, here. Sometimes “not knowing” is certainly a sign of weakness. For example, the CEO of a publicly traded company should know how the stock market works, how laws and regulations affect their business, and the key proponents of their core product. Not knowing those things would put them at a distinct disadvantage in their market, not to mention the downgrade in reputation within the company.

Employees generally like to know that their CEO knows what they’re doing

But as a coach, it’s ok to not know a single thing about one thing as long as you know a lot about something else.


It’s ok to know nothing about something, as long as you know a lot about something else.

I want to put double, triple, and quadruple emphasis on the second part of that sentence: "as long as you know a lot about something else."

What you know can be very specific or very general.

For example, your knowledge in establishing corporate structures is fairly specific. If that’s what you know how to do, then do it to the fullest. Or maybe you’re very good at seeing how each piece of the market works together at a 10,000 foot level. That’s a broad—but very valuable—skill.

So how do you get to the point at which you know a lot about something?

Let’s tackle that right now.


How to know a lot about something.

To know a lot about something, you must be very close to that something.

You must have done it in the past to a certain degree of success, been alongside someone who has done it to a certain degree of success, or currently be in an environment that is doing it to a certain degree of success.

Personally, I value “closeness to a problem” more than any other form of knowledge when it comes to business coaches.

The best businesses coaches I know have a great understanding of “closeness.”

I know one who has built and (profitably) sold 8 businesses. He knows that he knows a lot about two aspects of business in particular: making small businesses mighty, and teaching men how to take a more holistic family-first approach to their lives.

He knows how to do those things because he has done those things, and he is doing those things, and his clients are reaping the benefits.

You don’t need to have had a resume that looks like his to be super effective, but that is the standard all small business and startup coaches need to hold themselves to.

Including you.


How to truly help small businesses and startups as a coach.

Ok, so you’re ready to do this thing, huh? Good. Here are 10 hard tips on how to really help your clients.

1. Don’t regurgitate information unless you know it works.

Just because somebody wrote it in a book, blog, or article doesn’t make it true. Just because it feels good when you consume it and feels even greater to give it, that doesn’t mean it’s right for your client (this very article included).

Instead of regurgitating what you just read, investigate it. See if it’s credible. Find examples of how it works in the real world. Show your findings to your client. You owe it to your client to give them the best findings, not just the best readings.


2. Forget about branding yourself as an “expert.”

Some coaches—especially new coaches—tend to worry about their branding more than their actual work. That’s a huge mistake, and it can be detrimental to your client.

The title of “expert” is not one we give ourselves. “Expert” is a title given to you by others.

To truly become an expert, do unbelievable work. We’ll spread the word for you.


3. Connect your clients to resources.

Have fantastic resources ready for your clients, then connect them.

This is an especially powerful way to enter the coaching industry when you don’t have a particularly strong resume.

One of the most valuable things you can bring to the table is your network. This isn’t just huge for your client, but it’s huge for you too. If you have people in your network who can do things you can’t, then you don’t have to do everything.

That’s good because you can’t do everything.

There’s a responsibility on your end to be well-connected to people who you’ve vetted, tested, and trust.


4. Get in the trenches with us.


Forget your website for a moment. Rain check your upcoming professional photo shoot (I haven’t yet found the correlation between great headshots and great coaches, but I digress). Pause the YouTube video you’re watching about how to scale your coaching business from $0 to a billion dollars in 10 days.

Instead, pick up the phone and text your client.

Ask them what they’re working on right now, ask them if you can join them, then join them.

In most situations, giving advice is just not enough. Go execute with them. Stay up late with them. Bring the team coffee. Bring the energy. Bring the optimism. Bring the brains. Show them that no level of work is beneath you.

Show us that you truly want us to win.

We’ll work harder, guaranteed.


5. Try very hard to perform free work.

Bluntly, we often can’t afford you even if you’re worth it.

It doesn’t matter how much you talk to us about an “abundance mindset,” that doesn’t magically put money into our bank accounts. I’ve heard some coaches even say things like, “If you really want it, then you’d find a way to pay for it.” Every single penny counts when you’re a small business or when you’re starting up. And to be honest, we probably don’t want you more than we want results.

What coaches should be saying to people in our position is something more like this: “I really want you as a client, and I want to find a way for you to pay for me.” Then proceed to help us make money.

Remember, I’m not talking about becoming a coach in the personal development space or yoga space or anything other than small business and startups. If you really want to “double your rates” with those folks, do it. You deserve the money if you’re worth it. Right now, we’re talking about small businesses and startups. Fragile, often cash-strapped things.

I know we all have to make business decisions, and I acknowledge how naive this may sound. But hear me out.

There’s a fantastic lawyer in the KC area who devotes a ton of time to early stage tech startups in the community. He told me that the vast majority of his work with startups is pro bono, and the majority of his work overall is paid.

In other words, he tends to work with early stage startups for free. But free work is the minority of his overall work.

He also told me that a big handful of his paid clients came from his free work. He helped those companies gain traction, and those companies came to him as soon as they needed a lawyer. That’s how this stuff works.

I asked him why he does so much free work when he could be doing premium work for much more money.

“I’m passionate about startups,” he said. “But it’s definitely a business decision. I want to be the first lawyer these new companies interact with so I’m the first lawyer they come to when they can afford our firm.”

Play the long game, and find ways to be free. Whether that’s free office hours, sending people your blogs or books, or running workshops at coworking studios.

I promise you, we’ll remember you when we can afford you.


6. Do not charge for “motivation” unless your clients are explicitly asking for it.

Motivation starts businesses, but self-discipline builds businesses.

Imagine you’re a football coach. Motivation is very important throughout the season. But no amount of motivation can substitute for the hours of practice your team has to put in to win the championship. As the football coach, you have to play both roles of motivation and discipline. You have to show up for the games, you have to show up for the practices, and you have to motivate throughout.

Motivation is not worth as much money as you think.

If you were investing in a company, you wouldn’t want them spending your money on things that disappeared tomorrow. Think of yourself as an investor. After all, you don’t get your check unless they get theirs.

Don’t make startups and small businesses pay for motivation unless that’s explicitly what they’re paying you for.

If you charge, charge for work. The motivation is included.


7. Be unbelievably honest about what you know.

Your honesty can make or break their company.

You’re not dealing with Coke. You’re not dealing with Apple. You’re not dealing with Gucci.

You’re dealing with Anil, who runs a new coffee chain. You’re dealing with Jenny, who is working on a smart lamp startup. You’re dealing with Peder, who just created a new line of street wear.

If you don’t know something, admit it. Figure it out. Find someone who knows. Vet the source. Then share it with your client.

Letting your ego get in the way of proper advice could have a major impact on your client that puts both of you out of business.


8. Act as an extension of the company, not the overlord.

This is the major difference between a coach and a consultant.

A consultant doesn’t always have to be rooting for the home team, at least not as much as a coach. As a coach, you’ve always got a vested interest in your client’s success. Always. Or, at least, you should.

I’m not trying to say that consultants are overlords. What I’m trying to say is that I see too many coaches get a client and then act as if they’re the overload. They’ll come into the company with the mindset of a CEO. Remember, you’re at the company’s service, not the other way around. You’re not above the potential ramifications of your advice.

Be an advocate for your client. Bring them business. Pass out their business cards. Network for them.

When you act as an extension of the company rather than its demigod, the quality of your work will go way up. You’re invested, and it will show.


9. Practice what you preach, and be good at it.

This is a simple concept: If you’re coaching people on how to build a business, then have a solid coaching business.

I’m talking about a real business.

My definition of a real business is this: a machine that can run without you for at least a week. As a coach, you’ll be intimately tied to your brand, but that’s not an excuse to avoid putting the pieces, processes, and systems in place that turn you into a true business.

If, on the other hand, you’re not teaching people how to build businesses but how to do something else, then be good at whatever that is. Are you helping people navigate new marketing channels? Then be good at navigating them yourself.

You get the picture.

I once saw someone in a Facebook group who introduced themselves as a “social media marketing” coach who specialized in helping others attract clients via social media.

She had very few followers, very little engagement with those followers, and hardly an online presence at all. None of that is necessarily a deal-breaker, of course. She could have had a ton of experience (and success) from a corporate account instead of her personal account.

But it was her question that eliminated any hope of that being true.

After introducing herself as the social media expert who teaches others how to attract clients via social media, she asked the group this question: “I’m not having much luck finding clients. Anyone have any tips on how to do that via social media?”

Please, don’t be any version that person, not even a miniature replica.

Practice what you preach, and both you and your client will benefit.


10. If you’re no good, then move on from coaching.

This could be a hard pill to swallow, but stick with me.

Becoming a great coach is very tough work. And sometimes it can be very very VERY tough work. It takes more than a nice website with a downloadable ebook to be great. It takes more than professional headshots and fancy memes to be great. It takes more than a free introductory “Discovery Session” to be great.

If you’re working alongside small businesses and startups, you have to put it all on the line every single time.

That’s what your clients are doing.

And just as some people just aren’t cut out to be small business owners or startup founders, some people aren’t the right material to be great coaches.

Be honest with yourself.

It’s not enough to just give advice. It’s not enough to have “breakthroughs” with your clients unless you can also help them execute. It’s not enough to just motivate.

At the end of the day, you have to deliver positive results. If you can’t, then move on.


Wrapping this up.

As much as it might sound like I do, I don’t hate small business and startup coaches. I promise.

Actually, I think fellow entrepreneurs and small business owners probably need you more than we think we might. (We’re headstrong creatures, after all.)

What I’m pushing against is the idea that coaching is light work.

What you’re setting out to do could have a huge impact on a company.

Please make sure that the huge impact is a positive one.

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