I love business.

When I was a kid, I’d buy rugby league cards before school and resell the popular ones at a markup. Sometimes I’d put a bunch of packs in a plastic bag and charge people to pick one or two at random, like a lottery.

As a teenager, I watched my single mom run a singles club. She’d place ads in the newspaper, people would leave messages on our answering machine, she’d filter them, then host parties in our apartment or in restaurants so they could meet.

At 15, I worked for a guy who ran major under-18 dance parties in Sydney. At 19, some friends and I put on a couple of Asian dance parties. The first drew hundreds of people to a club on Oxford Street. The second ended with an extortion attempt by a gang that later became notorious in Australia, a fight with the Lebanese security crew running the venue, and about 50 police officers shutting it down.

At 20, I started what became the first full-colour hip hop magazine in the Southern Hemisphere. I worked in agencies by day and on the magazine at night. I expanded into distributing CDs, vinyl, and merch. I put on conferences and events. I designed the posters, printed them at Kinko’s, then walked around Sydney putting them up while hauling boxes of magazines around the city.

That work felt real. Every sale mattered. Every mistake stung.

I’d approach some of those businesses differently now, but back then there were very few people to talk to about work like that.

That feeling of having no real peer to think with is something I now hear from people running all kinds of businesses, big and small.

Common Challenges That Face Business Owners

On my travels, I love hearing about different business cultures.

In Medellín, Colombia, the local Paisa population is known for their business acumen. A lot of the earlier wealth came through farming - often coffee - and, yes, possibly illegal means, and there’s so much wealth in the hands of a few pockets of Medellín that one of the biggest financial conglomerates in Latin America - Sura - was born there.

In Saudi Arabia, people I meet often have multiple businesses - yes, something to do with oil, real estate, perhaps a jewlry or fashion brand. There’s a love of business and growth and sense that they want more access to the kind of thinking that a lot of us have done in agencies for years. My friends there pester me: “When will you start a business here? I’ll call the government right now.”

In Kenya, there are a lot of micro SMEs - think hair braiding, selling hair, selling imported sneakers, but also there are organizations like E4I who work with small coffee farmers, and people trying to create the next M-PESA (the main payment gateway in Kenya, owned by the main telco Safaricom).

And I’ve also worked with independent businesses in the USA (like Poo-Pourri).

The settings are different. The cultures are different. But the underlying challenges are often surprisingly similar.

And here’s what I hear:

1. “I don’t know what I don’t know.”

This is a truism but how I interpret it is as follows: “I want to take the next steps with my business but I’m stuck.”

2. “I’ve brought in outside help but it doesn’t go anywhere.”

This is usually a combination of outside help over-engineering the work they do (eg massive research projects) as well as the need for many SME owners to be the author of their own world while not knowing how to put hired help to the best use.

3. “I don’t have peers around me - it can feel lonely.”

Sometimes, the business owner is such a dominant personality that they struggle to get honest thinking of their growing teams. Or they spend so much time in the business that they struggle to find and form community for themselves.

4. “Do I need to put myself onto the Internet as a personal brand?”

This stresses out most business owners because their days are predominantly operational.

5. “I’m not sure how to expand.”

For a business that is mostly clicking - i.e. decent systems in place and profitable - that next step can seem difficult. Do you keep things simple and repeat the business in another location or country? Do you add new products or services and risk complicating your business?

6. “”I’m too close to the business to see it clearly.”

This might be the deepest challenge of all.

A lot of business owners do not need more information. They need perspective.

Why Strategists Fantasize About Working With Small Businesses

When I left corporate America, I tried to solve a dilemma for myself:

I loved doing strategy but I hated the bureaucracy and politics of doing it in large companies for large clients. It felt like nothing happened.

I’ve watched many strategists leave the big agency world and try to solve this problem for themselves. Perhaps they move client-side or they fantasize about working with start-ups and small businesses, hoping they can make a bigger impact. And they become addicted to a new drug called “consequence”.

For any of you thinking through these things now, I guarantee you’ll feel consequence by starting your own business. It might take a few years for you to shift the rhythm of your weeks, to ween yourself out of needing to intellectualize everything, and for you to become a good operator, but, with the way the world is going right now, it is worth considering.

After leaving corporate America, I took on a few consulting projects with small businesses, and I found that doing strategy with small businesses presents its own set of challenges:

Many business owners want to be the author of their entire business. This makes sense but it can also make a business owner un-coachable.

Business owners might share the work you do with a coach or a friend and it all falls apart.

Business owners might not be set up to implement your recommendations and default back to business as usual. Change is difficult and many business owners might require frequent coaching to push change through but a coaching business is very bitty to run unless you charge a lot of money.

Business owners aren’t sure how to value the work you might do as a strategist or creative mind unless they have spent time in or working with the agency world.

Over time, if you focus on working with business owners, you can tighten up your offer and how you work with them, while attracting people who are better set up for what you want to do.

The promise of being close to the business and the daily decisions is powerful. Consequence is addictive.

What Small Businesses Actually Need From Strategy

When I speak with small business owners, often what they need help with is this:

• Help working out what the business actually is
• Understanding basic business and marketing concepts
• A push to simplify how they communicate
• Understanding how to make their message about their customer
• Someone to untangle whether the real issue is brand, product, team, pricing, or focus

This is one reason strategy can feel so different in a small business. The work is usually less about “big ideas” and more about clarity.

Not many business owners are set up for what they themselves would call “out of the box” thinking. For example, I love the work my friends do at Vacation Inc - sunscreen that comes in a whipped cream format is incredible. Most business owners are trying to operate their business - making sure their farm survives bad weather, that deliveries happen on time and without theft, dealing with employees and contractors. Lobbing in wild ideas can give us strategy types a dopamine hit but they are difficult to pull off and many business owners don’t exist in such a three-dimensional world.

What This Means

This, to me, is the fantasy and the reality of working with small businesses.

The fantasy is closeness to consequence. Less theater. More reality. A chance to do work that actually changes something.

The reality is that most small businesses do not need a strategist to arrive like a magician. They need someone who can help them see their business clearly, describe it simply, and decide what to do next.

That kind of work can be incredibly satisfying. It can also be hard.

Follow me on Instagram @markpollard.