Introduction: The Question Every Parent Gets Asked
I got a text Tuesday night. It said:
“Chris, my 16-year-old just asked if she should start a business or get a job at Tim Hortons. I froze. I told her to focus on school. But honestly? I have no idea what to tell her. What would you say?”
Then Wednesday morning, another one:
“My son wants to start a lawn care business but I’m worried he’ll fail and get discouraged. Should I talk him out of it?”
Thursday afternoon:
“My daughter asked why she needs to go to university if she could just start selling stuff online. I panicked and said ‘you need a backup plan.’ Did I just kill her dreams?”
Three different parents. Same week. All texting me the same fundamental question: What should I tell my kids about entrepreneurship?
And here’s what got me: These are GOOD parents. They love their kids. They want the best for them. They’re trying to give good advice.
But nobody taught them this stuff. So when their kid asks about starting a business, they default to what THEIR parents told them:
- “Get good grades.”
- “Go to college.”
- “Get a stable job with benefits.”
- “THEN maybe, someday, if you’ve saved enough money and have enough experience, you can think about starting something.”
It’s the same advice that’s been passed down for three generations.
Except that world doesn’t exist anymore.
The Problem: We’re Preparing Kids for a World That No Longer Exists
I live in Sault Ste. Marie, Ontario. I’ve watched the steel mill that employed thousands shrink to hundreds. I’ve watched “secure” government jobs get cut. I’ve watched people with 20 years at a company lose everything in a restructuring.
There’s no such thing as job security. There never really was.
But we keep telling our kids to chase it.
The Numbers Don’t Lie
According to Statistics Canada:
- The average Canadian changes jobs 15 times over their career. Fifteen times. And that number is INCREASING for younger generations. The “get a job and stay there 30 years” model is dead.
- Youth unemployment in Canada sits around 10-12% – double the adult rate. We’re telling kids to get jobs, but the jobs aren’t there.
- According to BDC, 70% of Canadians have thought about starting a business, but most never do. Why? Because nobody taught them how. Their parents told them it was too risky. Their teachers trained them to be employees. And by the time they’re 35 with a mortgage and two kids, they feel trapped.
Meanwhile, entrepreneurship – the thing we tell them is “risky” – is actually the most secure path available.
Because when you know how to create value and get paid for it, nobody can take that away from you. You can’t get laid off from your own business. You can’t get outsourced. You can’t get replaced by AI if you’re the one USING AI.
The Generational Disconnect
Here’s what most parents say when their kid mentions starting a business:
- “Focus on school first.”
- “You need experience before you can start a business.”
- “Entrepreneurship is too risky – what if you fail?”
- “Get a job so you have something stable, THEN think about starting something on the side.”
- “You need to go to college so you have a backup plan.”
And I get it. I really do. These parents are terrified their kid will struggle. They’re trying to protect them. They remember how hard it was when they were young and broke, and they don’t want that for their kids.
But here’s what they’re actually doing: They’re teaching their kids to be employees in a world that doesn’t value employees anymore.
And worse: They’re teaching kids to wait until they’re older, more experienced, have more to lose. We’re teaching them to start a business at the WORST possible time.
So what SHOULD we tell our kids?
I’m going to give you three conversations. Three things every parent should talk to their kids about. Not once – these are ongoing conversations. But if you start them tonight? You’ll give your kid something more valuable than a college fund.
You’ll give them the ability to create value in the world. And get paid for it.
Conversation One: “There Are Three Ways to Make Money”
Most kids think there are two options: get a job, or start a business.
But there are actually three fundamental ways to make money. And understanding all three is critical.
Path 1: Work for Someone Else
You trade your time for their money. This is a job. Hourly, salary, doesn’t matter – you’re renting your time to someone else.
This is how most people make money. It’s totally fine as a starting point. But it has a ceiling – there are only so many hours in a week.
According to Statistics Canada, the average Canadian worker earns $62,000 per year. That’s decent. But to double that income, you’d have to work double the hours. Which is physically impossible long-term.
Path 2: Work for Yourself
You create value directly and get paid for it. This is entrepreneurship. This is starting a business.
You still trade time for money at first, but YOU control:
- The rates
- The clients
- The type of work
- Your schedule
- Your income ceiling
And eventually, you can build systems that work without you.
Path 3: Have Your Money Work for You
You buy assets that generate income whether you work or not. This is investing. Stocks, real estate, businesses you own but don’t run.
This is how wealthy people make money.
The Key Insight
Here’s what most people miss: Path 2 is the fastest route to Path 3.
When you work for someone else (Path 1), you make just enough to survive. Maybe you save a little. But it takes decades to build enough assets to live on.
When you work for yourself (Path 2), you make MORE per hour because you capture the full value you create. You save faster. You invest sooner. And you can build a business that eventually runs without you – which itself becomes a Path 3 asset.
In our previous episode, “How to Make MORE Money,” we broke down exactly how this works. If you haven’t listened yet, start there for the full framework.
What to Tell Your Kid
So when your kid asks “should I get a job or start a business?” the real answer is:
“Start a business. Even a tiny one. Because that’s how you learn to create value. And creating value is the only skill that matters.”
Conversation Two: “You Can Start With $100 – Here’s How”
This is where parents get scared. They think “business” means:
- Business plan
- Investors
- Loans
- Storefront
- Employees
- Inventory
- Legal incorporation
- Accountant
- Website
- Marketing budget
And yes, SOME businesses need those things. But most don’t. Not at first.
The businesses your kids can start need three things:
- A skill or product people want
- Someone willing to pay for it
- The courage to ask
That’s it.
Let me give you the three types of businesses any kid can start for under $100:
Type 1: Service Business (Sell Your Time/Skill)
Startup cost: $0-$50
This is the easiest way to start. You already have skills. You just need to find someone who will pay you to use them.
Examples:
Tutoring – You’re good at math? Tutor younger kids. $25-40/hour. A Grade 12 student tutoring Grade 9 math can easily charge $30/hour. Work 5 hours a week = $600/month.
Lawn care – Mower, gas, rake. Charge $40/lawn. Do 10 lawns every Saturday = $1,600/month working ONE day a week.
Babysitting – Parents pay $15-20/hour for responsible teens. Three evenings a week = $300-400/month.
Dog walking – $20/walk, can walk 3-4 dogs at once. Daily walks for 5 dogs = $2,000/month.
Snow shoveling – Seasonal but lucrative in Canada. $30-50/driveway. 20 driveways after a snowfall = $600-1,000 in a few hours.
House cleaning – $80-100 per house, 2-3 hours of work. Two houses a week = $640-800/month.
Car detailing – $100/car, supplies cost $50 to start. Five cars a month = $500 profit while learning a trade.
The numbers on these are REAL. A kid who mows 10 lawns every Saturday at $40 each makes $400/week. That’s $1,600/month working ONE day a week. More than a part-time job at Tim Hortons, and they control their schedule.
Type 2: Product Business (Make or Resell Something)
Startup cost: $50-$100
This requires a tiny bit of inventory, but the profit margins are often better.
Examples:
Baking – Cookies, cakes, cupcakes for events. Start with one specialty. Birthday cupcakes for $30-50 profit per order. Five orders a month = $150-250 profit. Grow from there.
Crafts – Jewelry, art, custom items. Sell on Etsy or at local markets. Materials cost $50, sell items for $20-40 each with $15-30 profit margins.
Reselling – Buy at thrift stores, sell on Facebook Marketplace or Kijiji. 2-3x markup is normal. $100 invested can turn into $200-300 with smart buying.
Detailing products – Buy car care supplies in bulk, resell to neighbors at markup. Or offer mobile detailing services.
Seasonal products – Lemonade stand evolved. Not lemonade, but iced coffee or specialty drinks at community events, sports games, festivals.
I know a kid in Sault Ste. Marie who buys vintage video games at garage sales for $5-10 and resells them online for $40-80. He makes $500-800/month working a few hours on weekends.
Type 3: Digital Business (No Physical Limits)
Startup cost: $0-$50 (usually just internet)
This is the most scalable. No inventory. No physical limits. But requires more skill development.
Examples:
Social media management – Local businesses need help with Instagram/TikTok. $200-500/month per client. Manage 3 clients = $600-1,500/month.
Graphic design – Logos, posters, event graphics using Canva or free tools. $50-200 per project. Learn on YouTube.
Content creation – YouTube, TikTok, blog with affiliate income or sponsorships. Takes time to build, but scales infinitely.
Online tutoring – Same as in-person but can reach more students globally. Use Zoom, charge the same rates.
Freelance writing – Businesses need blog posts, emails, newsletters. $50-200/article. Five articles a month = $250-1,000.
Video editing – Content creators need editors. $20-50/hour or $100-300 per video. Learn on YouTube using free software.
According to Statista, the creator economy (people making money from content online) is worth over $100 billion globally. Your kid doesn’t need all of it. They just need $500/month to start.
The Math That Changes Everything
Let’s do real numbers. Because parents worry about “is this worth it?”
Scenario 1: Job at Tim Hortons
- $15.50/hour (Ontario minimum wage)
- Work 12 hours/week (after school/weekends)
- Gross: $186/week = $744/month
- After taxes: ~$650/month
- Skills learned: Show up on time
Scenario 2: Lawn Care Business
- Mow 10 lawns/week at $40 each
- Work 10 hours/week (including travel)
- Gross: $400/week = $1,600/month
- Costs: $100/month (gas, maintenance)
- Net profit: $1,500/month
- After taxes: ~$1,300/month
- Skills learned: Customer service, marketing, pricing, problem-solving, reliability, money management
Your kid makes DOUBLE the money in FEWER hours. And they’re learning skills they’ll use their entire life.
What About Startup Costs?
“But Chris, what if we can’t afford to give them $100 to start?”
Then they start with a service business that costs $0. Tutoring. Dog walking. Babysitting. Snow shoveling.
They use the profit from that to fund a product or digital business later.
This isn’t about you funding their business. It’s about teaching them to fund it themselves.
Conversation Three: “Failure Is Cheap When You’re Young – Expensive When You’re Old”
This is the conversation most parents avoid. Because we don’t want our kids to fail.
But here’s the truth: Your kid IS going to fail at something. The only question is when, and how much it costs.
Would you rather they fail at 16 with $100? Or at 35 with a mortgage?
When You’re Young (The BEST Time to Fail)
Advantages:
- You live at home (no rent, no mortgage risk)
- You have energy (can work evenings/weekends without burning out)
- Stakes are low (losing $100 not $100,000)
- You recover fast (decades ahead to rebuild)
- Failure is a story, not a tragedy
- Parents can help guide and support
- No dependents relying on your income
- Can pivot quickly without consequences
Example: A 16-year-old starts a lawn care business. Gets 5 customers. Makes $800 total over the summer. Learns that marketing matters, referrals are everything, and showing up on time is crucial. Next summer, gets 15 customers by asking for referrals. Makes $3,500. Hires a friend to help. Summer 3, has 30 customers and teaches younger sibling the business.
That’s not a failure story. That’s a success story that started with $100 and 5 customers.
When You’re Older (The WORST Time to Fail)
Disadvantages:
- You have a mortgage, car payments, family depending on you
- You’re exhausted from your day job
- Stakes are terrifying (can’t afford to lose savings)
- Recovery takes years
- Failure feels like the end
- Social pressure and judgment
- Risk of losing everything
- Less time to rebuild
Example: A 38-year-old quits their job to start a business. Drains $50,000 in savings. Business fails after 18 months. Now has to find a new job while explaining the gap in their resume, with depleted savings and family stress. Takes 5+ years to financially recover.
The Real Story About “Failure”
The parents who texted me are worried their kids will fail and get discouraged.
But here’s what actually happens:
Most “failures” in youth entrepreneurship aren’t failures at all. They’re learning experiences that cost $50-500 instead of $50,000-500,000.
Your kid starts a baking business. Bakes 20 cupcakes for an event. They’re good but not great. Makes $40 profit. Realizes they need to improve their recipes and presentation. Next order, they’re better. Third order, people are asking for their contact info.
That’s not failure. That’s iteration.
Compare that to: Going to college for 4 years ($40,000+ debt), getting a degree, realizing you hate the field, and NOW having to figure out how to make money while servicing student loan debt.
Which scenario is actually riskier?
What About School?
Parents always ask: “Should they skip college to start a business?”
My answer: School and entrepreneurship aren’t opposites. They’re complementary.
Let them start the business NOW. While they’re in high school or college. It doesn’t have to be 40 hours/week. It can be 5-10 hours on weekends.
Scenario A: Start now, keep going to school
- Test business ideas with minimal risk
- Build real-world skills
- Generate income
- If business takes off, they can choose to go full-time (college will still be there)
- If business fails, they learned valuable lessons and have a degree
Scenario B: Wait until after college
- $40,000+ in debt
- No business experience
- No idea if entrepreneurship is right for them
- Now have to start a business while servicing debt and needing immediate income
- Pressure is 10x higher
The worst-case scenario isn’t “my kid skipped college to start a business.”
It’s “my kid spent $40,000 on a degree they’re not using and now they’re 25 and don’t know how to make money.”
Start the business now. Keep going to school. See what happens. Give them options.
The Real Goal: Teaching Them to Create Value
Here’s what this is really about.
It’s not about your kid becoming a millionaire at 18. It’s not about them skipping college. It’s not even about the business succeeding.
It’s about teaching them the most important skill in the world: creating value and getting paid for it.
Because here’s the secret: If they can do that, they’ll never be broke. They’ll never be desperate for a job. They’ll never feel trapped.
The Security of Skills Over Credentials
If they lose their job? They’ll start something.
If the economy crashes? They’ll find a need and fill it.
If AI takes their role? They’ll adapt and use it as a tool.
If their industry changes? They’ll pivot to something new.
That’s real security. Not a “stable job.” Not a pension. Not even a degree.
The ability to create value.
And you can’t teach that in a classroom. You can only teach it by doing.
So when your kid says “I want to start a business,” what you’re really hearing is:
“I want to learn how to create value.”
And your job as a parent isn’t to protect them from failure. It’s to say:
“Let’s figure it out together. What’s the smallest version of this idea? What would it cost to try? Let’s test it and see what happens.”
That’s the conversation that changes everything.
Your Golden Hour Challenge: The Dinner Table Business Plan
Here’s your action step. And I mean tonight. Don’t wait. Don’t overthink it.
Tonight, at dinner, you’re going to have The Dinner Table Business Plan conversation with your kid.
Step 1: Ask The Question (10 minutes)
Sit down with your kid. Put away phones. Make this a real conversation.
Ask them: “If you could make money doing anything – anything at all – what would it be?”
Don’t judge the answer. Don’t say “that’s not realistic.” Just listen.
Maybe they say:
- “I want to make videos on YouTube”
- “I want to bake cakes”
- “I want to teach people guitar”
- “I want to resell sneakers”
- “I don’t know”
All of those are valid. Even “I don’t know” is valid – you can work with that.
If they say “I don’t know,” ask follow-up questions:
- What are you good at?
- What do your friends ask you for help with?
- What do you spend hours doing that doesn’t feel like work?
- If money wasn’t an issue, how would you spend your time?
Step 2: Pick ONE Thing (15 minutes)
Help them narrow it down to ONE specific thing they could start with $100 or less.
Not: “I want to be a YouTuber” (too vague) Instead: “I want to make 5 YouTube videos teaching people how to cook easy meals, and see if anyone watches them.”
Not: “I want to start a baking business” (too broad) Instead: “I want to bake cupcakes for 3 birthday parties this month and see if people will pay $30 for a dozen.”
Not: “I want to make money online” (no focus) Instead: “I want to design 5 custom social media graphics for local businesses at $50 each.”
Make it:
- Specific (one product or service)
- Measurable (3 customers, 5 videos, 10 lawns)
- Time-bound (this month, this summer, next 30 days)
- Cheap to test ($100 or less)
Step 3: Do The Math Together (20 minutes)
This is the part most parents skip. But it’s the most important.
Sit down with a piece of paper and actually calculate:
What would they charge?
- Research what others charge (Google it together)
- Don’t undervalue their work
- Start with market rate
What are the costs?
- Materials
- Gas/transportation
- Tools/equipment
- Time investment
How many customers to break even?
- If cupcakes cost $15 to make and sell for $30, they need 7 orders to cover the $100 startup cost
How many customers to make $500 profit?
- Real goal math
- Shows them it’s achievable
- Makes it concrete
Where will they find customers?
- Friends and family first (easiest warm leads)
- Facebook community groups
- Word of mouth/referrals
- Flyers in neighborhood
- Social media (Instagram, TikTok)
- School bulletin boards
- Community centers
Write all this down. Make it real. Make it concrete.
Step 4: The Challenge (15 minutes)
Now you give them the challenge:
“Make your first $100 in profit in the next 30 days. I’ll help however you need. But you have to do the work.”
Then ask them:
- What’s the first step?
- When will you do it?
- What help do you need from me?
Maybe the first step is:
- Post in a Facebook group offering lawn care
- Bake a sample batch and take photos
- Message 10 people offering tutoring
- Film the first YouTube video
- Create 3 sample designs to show potential clients
Whatever it is, make them commit to a date.
“I’ll post in the Facebook group by Wednesday.” “I’ll bake the samples this weekend.” “I’ll message 10 people by Friday.”
Your Role as Parent
Your job isn’t to do it for them. Your job is to:
Remove barriers:
- “I’ll drive you to buy supplies”
- “I’ll help you set up a PayPal account”
- “I’ll share your post in my Facebook groups”
Give feedback:
- “Let’s practice your pitch”
- “How can you make that better?”
- “What would make you want to hire you?”
Hold them accountable:
- “Did you post yet?”
- “How many people did you message?”
- “What did you learn from that?”
Celebrate attempts (not just successes):
- “I’m proud you tried”
- “That was brave to ask”
- “What will you do differently next time?”
The Agreement
Make this deal with them:
“If you try this for 30 days and genuinely put in the effort, I won’t care if you make $10 or $1,000. I care that you TRIED. Because trying is the only way you learn.”
Take the pressure off perfection. Put the pressure on effort.
And then actually follow through. Don’t criticize. Don’t micromanage. Just support.
Because here’s what’s really happening:
You’re not just helping them start a business. You’re teaching them that they can create value in the world. That they’re not helpless. That they don’t need permission or a perfect plan.
They just need to start.
And 10 years from now, when they’re 26 and everyone else is complaining about their jobs? They’ll be starting their third business. Because you taught them how.
Summary: Three Conversations That Change Everything
Three parents texted me this week asking: “What should I tell my kid about entrepreneurship?”
Here’s what you tell them:
Conversation 1: There Are Three Ways to Make Money
- Work for someone (job) – Path 1
- Work for yourself (business) – Path 2
- Have money work for you (investing) – Path 3
Path 2 is the fastest route to Path 3. Entrepreneurship isn’t the risky option – it’s the secure one. Because the ability to create value can never be taken away.
Conversation 2: You Can Start With $100
Three types of businesses any kid can start:
- Service business (sell your time/skill) – $0-50 startup
- Tutoring, lawn care, babysitting, dog walking, snow shoveling, house cleaning, car detailing
- Product business (make/resell something) – $50-100 startup
- Baking, crafts, reselling, seasonal products
- Digital business (infinite scale) – $0-50 startup
- Social media management, graphic design, content creation, online tutoring, freelance writing, video editing
The math is better than a part-time job AND they learn skills they’ll use forever. A lawn care business makes double what Tim Hortons pays in fewer hours.
Conversation 3: Failure Is Cheap When You’re Young
Would you rather they fail at 16 with $100 or at 35 with a mortgage?
The best time to start is when:
- The stakes are low
- The recovery is fast
- They have decades ahead
- They live at home
- Parents can guide them
Starting young isn’t risky. Waiting until they’re older with more to lose is what’s actually risky.
Your Golden Hour: The Dinner Table Business Plan
Tonight:
- Ask: “If you could make money doing anything, what would it be?”
- Pick ONE thing to start with $100 or less
- Do the math together – real numbers, real plan
- Challenge: Make first $100 profit in 30 days
The goal isn’t to make them millionaires. It’s to teach them the most valuable skill in the world: creating value and getting paid for it.
Because if they can do that? They’ll never be stuck. They’ll never be desperate. They’ll never feel trapped.
And that’s real security.
Related Episodes
- What IS Money? – Understanding money as a measure of value (foundation episode)
- How to Make MORE Money – The three paths to building wealth explained in detail
Resources for Parents and Kids
For Learning Business Basics:
- SCORE Mentors (free business mentoring)
- Junior Achievement Canada (youth entrepreneurship programs)
- Your local Chamber of Commerce (youth programs)
For Finding Customers:
- Facebook community groups
- Nextdoor app
- Community bulletin boards
- School networks
For Managing Money:
- Youth bank accounts (most Canadian banks offer them)
- Simple bookkeeping apps (Wave is free)
- PayPal or e-transfer for payments
Books to Read Together:
- Rich Dad Poor Dad for Teens by Robert Kiyosaki
- The Startup Squad series (for younger kids)
- kidpreneurs by Adam Toren and Matthew Toren
Connect with Chris:
- Website: businessisgood.com
- LinkedIn:
- Instagram: @coachchriscooper
