Entrepreneurship Is a Hedge, Not a Risk

AI is hollowing out the entry-level ladder—and waiting for “safe” jobs might be the riskiest bet of all. In this episode, I make the case that entrepreneurship isn’t a leap off a cliff; it’s a hedge against uncertainty. We start with why doing beats studying: real skills—focus, math-in-action, communication, selling, project ownership—grow faster through small businesses and gigs than through lectures. Youth (and career-changers) should learn by shipping, reflecting, and iterating with a mentor—more like a trade than a theory class.

Then we track how once-stable white-collar roles (fitness coaching, accounting, creative services, even analysis work) now reward entrepreneurial abilities: building relationships, marketing yourself, collaborating, packaging outcomes, and selling solutions. These aren’t “nice to have”; they’re the new prerequisites.

Finally, we explore entrepreneurship as a practical hedge. Instead of graduating into debt, degree, and delay, you can earn while you learn—stacking micro-projects, building a network, and compounding skills that can’t be automated or taxed away. Whether you go full-time or keep a job, a small business gives you agency: more ways to make money, more optionality in downturns, and a faster path to confidence and competence. Don’t wait for permission. Start small, start now, and let experience be the teacher that sticks.

Connect with Chris Cooper:

Website - https://businessisgood.com/

Most service companies start the same way: a great practitioner opens shop and sells their own time—hairdressers, trainers, dentists, therapists, lawyers. That works… until it doesn’t. Quality depends on the founder; hiring “clones” leads to uneven results and micromanagement; SOPs multiply; and the business becomes a mini-bureaucracy. In this episode, I explain why the “be the best and do it all yourself” approach traps you—and how to scale without wrecking your brand.

We walk through the five most common growth models (rent-a-chair, senior-junior-novice ladders, HQ services platform, affiliate/license, and “big fish + aux team”)—what they do well and where they stall. Then I lay out a practical move from practice to platform: productize outcomes (not just services), define roles and tiers, keep marketing/sales centralized, and build continuity revenue (memberships, cohorts, retail) while letting intrapreneurs grow under your brand. Finally, we add leverage backstage with AI—intake, plan drafting, comms, QA—so your team spends more time on human moments and outcomes.

If you’re stuck between being the best in town and working 70-hour weeks, this is your path out: a platform where good people can do great work—and your brand gets stronger every time they do.

Connect with Chris Cooper:

Website - https://businessisgood.com/

Canada’s tax problem isn’t just slow phones at the CRA—it’s a century of bolt-on rules that made filing confusing, subjective, and expensive to administer.

A new review found CRA contact centres gave accurate answers only 17% of the time during the 2025 tax season window, echoing long-standing issues flagged by earlier audits (including millions of dropped and blocked calls).

This complicated tax system creates unnecessary bureaucracy, wasted money, unpaid taxes, and a subjective audit process that means you can pay more (or less) taxes depending on how well your auditor slept the night before.

Hiring more agents won’t fix a tax law that’s impossible to interpret. Simpler rules will.

In this episode, I sketch a path to simpler, fairer, faster taxes. First, a quick history lesson on why we have income taxes, and how they became a Frankenstein's monster of laws that no one can understand. This will show us that the problem is getting worse, and will keep getting worse until we have a major system overhaul. Then I'll get into solutions.

I explore proven options from abroad:

Pre-populated / return-free filing (pioneered by Denmark; now used in most OECD countries) to slash time, phone calls, and errors—already being piloted in Quebec for simple returns.

Flatter, broader bases with minimal carve-outs (think Estonia’s ultra-simple system) and NZ’s broad-base/low-rate GST—models that raise revenue with less friction.

Withholding-as-final for straightforward T4 earners, so most people don’t file at all unless their situation is complex—borrowing design cues from the Nordics.

Look, nobody wants to talk about tax until they have to. But when they do - and they have to every year - they hate everything about our tax system. It creates unnecessary frustration and anger. Nobody wants to deal with the CRA, and nobody wants to work for the CRA either. Why would they?

Many people who don't pay taxes do it out of frustration - they just give up. They're not evil; they're just overwhelmed. Tax filings have become a game.

I’m not anti-tax; I’m anti-waste. My companies happily pay millions of dollars in corporate taxes annually. Its employees add another 1M in income taxes to our society, and you can add HST on top of all of it.

What I want is less money burned collecting taxes and more money spent on services. If Canadians want better healthcare, safer streets, and a clearer deal with citizens, we should push for tax simplification, not just bigger call centres.

Sources:

CRA call centres: 17% accuracy (Feb–May 2025); prior audits on access/accuracy. Investment Executive+1

Canada’s income tax history (1917 “temporary” tax). The Canadian Encyclopedia

Provincial/territorial corporate tax—CRA administers most; exceptions Quebec & Alberta. Canada.ca

Pre-populated returns (Denmark origin; 28 OECD countries). Tax Policy Center

Quebec simplified / pre-filled return pilot (2025 filing for 2024 year).