If you had to stare into a camera or two, and share a lesson with someone who’s just getting started in your career or business, what would you say?

I’ve been a “business owner” officially for over 13 years now, when I first incorporated my agency in the spring of 2013. Before that, I was already figuring things out as a sole proprietor, freelancer, and nonprofit founder — so I’ve spent a lot of time learning business lessons along the way. And I’ve had a chance to share through various events, classes and one-on-ones.

Over the years, my work has become focused on B2B: serving businesses that support other businesses.

One of the best parts of that work is getting to know other business owners, up close.

Not just seeing what they sell, but understanding what they’re building. The problems they’re trying to solve, the decisions they’re carrying, the risks they’re taking — and the things they keep doing because something about the work still feels worth it.

It’s why I’m hosting The Founder Signal event for Toronto Tech Week in a couple weeks.

Small businesses are often thought of as a minor character in our economy, but they’re actually most of the story.

Canada had 1.10 million employer businesses as of December 2024, and 98.2% of them were small businesses. They employ 46.6% of Canada’s private-sector workforce.

So when we talk about small business owners, it’s not niche. We’re talking about the people behind local services, growing teams, professional firms, family-run companies, product brands, shops, studios, trades, clinics, agencies, and everything in between.

I had the chance to work with a client called Huumans on a content series built around those people.

The idea was simple: Real advice from real business owners.

The goal was to create something useful, and not just promotional. A searchable library of practical, honest, owner-to-owner advice that other Canadian business owners could learn from.

After going through the interviews, a few themes became very clear.

But first, it began with refining the positioning. I’m a huge advocate of starting with brand strategy first. For context, here’s where we landed:

Part of our work with Huumans includes a video content series.

As I mentioned, they wanted to capture advice that other small business owners could actually use. The kind of advice someone might search for at 11:37 p.m. after a long day running the business. Questions like:

• How do I raise prices without losing everyone?

• How do I know when to hire?

• How do I manage cash flow when everything feels unpredictable?

• How do I decide which projects to say yes to?

• How do I stop trying to serve everyone?

• How do I build something sustainable without burning myself out?

They’re questions that come up when you are the one making decisions, carrying the risk, managing the team, watching the bank account, and still showing up for customers.

That’s the heart of the Huumans Owner Stories series. Short videos built around clear takeaways, not scripted inspiration or overly polished brand content. Each story needed to surface one useful lesson, backed by lived experience.

Clarity Content filmed these over 2 days.
You can see how the series is introduced on the website:

Once you create a free account with Huumans, you can watch the first few videos that are live (with many more to come). Here’s how that looks within the product:

Behind the owner stories series

A lot of business content stops at the advice:
“Know your numbers.” “Niche down.” “Hire slowly.” “Charge your worth.”

But what makes advice land is the story underneath it.

• What did it cost you to learn that?

• What changed after you made the decision?

• What did you misunderstand at first?

• What would you do differently now?

That is where the value is.

Our content format was intentionally simple:
One owner. One lesson. One story behind it.

The interviews we filmed were built around 2 layers:
The tip: What would you tell another business owner?
The story: What happened that taught you this?

The strongest interviews gave us the kind of specificity that generic content can’t fake: owners talking about losing clients after raising rates, ignoring market signals, learning to say no, hiring the wrong people, watching cash flow, narrowing their audience, and building systems after chaos had already taught them the lesson.

What do owners actually want to know?

What came through

The owners came from different industries and business models, but the themes were surprisingly consistent.

The visible business is only part of the job.

Customers see the haircut, the bouquet, the cookie, the therapy session, the product, the service, the finished work.

The owner sees the rest: Payroll. Pricing. Cash flow. Hiring. Customer acquisition. Systems. Late-night decisions. Emotional weight. The quiet pressure of knowing that most decisions come back to you.

One of the clearest patterns across the interviews was that many owners start as makers, practitioners, or operators. They are good at the craft. Then the business grows, and the job changes.

Suddenly, being good at the work is only one part of running the business.

You also have to become good at leading, planning, deciding, selling, hiring, adapting, and sometimes saying no to things that look good on paper.

That shift is rarely glamorous. (I’ve gone through it).

But it is where a lot of the real growth happens.

Lessons for You

Producing this video series, there have been a few recurring tips and takeaways that I’ve observed, which I’m passing on to you…

Focus is usually learned the hard way.

Focus isn’t easy, I know. It’s about not trying to serve everyone, not saying yes to every project. Not building for every possible customer, and not chasing every growth path at once.

A lot of clarity in business comes from subtraction.

The owners who sounded the clearest were often the ones who had learned what to stop doing. That is a hard lesson because saying yes feels productive. Saying no feels risky. But at some point, every owner has to decide what kind of business they are actually building.

Pricing is emotional before it becomes strategic.

Pricing came up again and again. Early on, pricing is often tied to fear. Fear of charging too much, losing people, of being judged, or of not being worth it.

Over time, the stronger owners started talking about pricing differently. Pricing became connected to value, sustainability, margins, demand, positioning, and the kind of business they wanted to run.

The collective lesson was not simply “charge more.” It was more grounded than that: Price based on reality, not insecurity.

Hiring is about character, not just credentials.

When owners talked about team, they rarely focused only on résumés. They talked about attitude, work ethic, trust, fit, willingness to learn, ability to handle pressure, and alignment with the business.

In a smaller company, every person has an outsized impact. The wrong person does not just affect a department. They affect the culture, the customer experience, the owner’s time, and sometimes the future of the business.

Skills matter. Character travels further.

Systems are what make growth survivable.

You’ve heard “work smarter, not harder” before. The better lessons were not just about working harder, they were about building structure. Project management, approval processes, customer journeys, financial tracking, meeting rhythms, AI tools, automation.

Simple rules for making decisions.

The early stage of a business is often powered by energy. Sustainable growth needs repeatable systems. That came through clearly in the interviews. The owners were not talking about what it takes to make the work more manageable, more consistent, and less dependent on constant improvisation (not romanticizing hustle).

The market gets a vote.

Several owners described a version of the same experience:

They had a vision, they believed in an idea, and they built something. Then the market responded.

Sometimes the market confirmed the idea. Sometimes it challenged it, sometimes it pointed them somewhere better. That is one of the more humbling parts of business ownership.

You need conviction, but you also need to listen.
You need a point of view, but you also need feedback.

You need to keep going, but you also need to know when persistence is becoming stubbornness with better branding.

There’s more where this came from, but I can’t give it all away here…

Why this kind of content works

What makes the Huumans stories valuable is specificity… you can’t Google it all. Especially things like:

• What really happened?

• What changed?

• What did the owner learn?

• What did the owner stop doing?

• What would the owner tell someone one year behind them?

That is the kind of content that becomes useful beyond the campaign itself.

It can help someone make a better decision.
It can give language to a challenge they are already feeling.
It can help a business owner feel less alone in the messy middle.

From a content strategy perspective, it shows why human experience still matters so much.

There is no shortage of business advice online.
There is a shortage of advice that feels earned.

The content and learning takeaway

The series is more than a collection of owner profiles for Huumans. It’s a way to document the practical knowledge that already exists inside the small business community.

There’s a content strategy lesson here.

Sometimes the best content is not about saying more.
It is about asking better questions, listening closely, and packaging the answers in a way that helps someone else.

For small business owners, the lessons were clear:

• Know your customer.

• Protect your cash.

• Narrow your focus.

• Price with confidence and context.

• Hire for trust and fit.

• Build systems before chaos forces you to.

• Listen when the market gives you information.

• Keep learning faster than the business changes.

Different businesses. Same hard lessons.
That’s part of what made the project feel so human.

There are thousands more stories to be told. I’m looking forward to continuing the series for Huumans and their partners.

What’s your story? What would you tell other owners?

If you’re a business owner and want to be featured in the series, you can apply now for our next set of videos.

Huumans has an owner, too. That’s Bill Murphy. He founded several startups and exited successfully (and unsuccessfully). He says he’s doing this to help other owners save time, save money and “become human again” — it’s humans helping humans.

Huge thank you to the team at Huumans and to Jason Goodman, who’s been an awesome collaborator on this project, and of course to Javon, who filmed every video with Clarity Content.

Until next week,