Brad Poulos is an educator and consultant in the small business space. He teaches in the entrepreneurship department at Toronto Metropolitan University in Toronto, where he has been on faculty for about fifteen years. Alongside his teaching, Brad consults to small businesses in Canada and the United States, primarily those in the $5–50 million revenue range. He is the author of three books — Most Problems Solve Themselves, The Small Business Operator's Manual, and From Pitch to Payoff — and operates a business planning and cadence system for small business owners at confidentoperator.com.

• Why lean startup replaced the traditional business plan — and what that means for founders today
• The SaaS expansion trap: why staying in your niche beats being pretty good at five things
• The Barbados test for knowing whether you own a business or own a job
• How to delegate outcomes instead of tasks, and what that looks like in practice
• Organic vs. mechanistic org structure — and how to get the right people in the right seats
• When to seek angel funding vs. bootstrapping, and why the VC carrot comes with a stick
• Brad's controversial take: a post-pandemic generation that struggles to solve problems

Brad opens with a story that reframes how most people think about business planning. Early in his career, he raised two million dollars from Bell Canada's board using a thick business plan full of projections — and had never spoken to a single prospective customer before the meeting. That was the old playbook. Today's curriculum is built on lean startup methodology: validate with real customers before you write a single number. The infrastructure shift matters too — what once required custom bank-approval code is now a Shopify checkbox. Entrepreneurship is more democratic, but that cuts both ways.

The episode hits its stride when Brad and Jeremy dig into what it takes to actually own a business versus a high-paying job. Brad's test is clean: "If you can't go to Barbados and sit on the beach and you're making money, you do not have a business. You own your job." The fix isn't hiring more people — it's changing what you hand them. Jeremy's framing lands hard: don't delegate tasks, delegate outcomes. A-players figure out the tasks themselves. B-players need the list. Knowing the difference is what separates a good operator from a frustrated one.

Episode Exerpt:

JEREMY RIVERA

I’m curious what your advice is right now for SMBs in manual services — tree trimming like McAllister Tree Service, installing concrete walls in Florida, doing home repair in Tennessee. If you’re geo-based and doing services, what does that look like from your perspective?

BRAD POULOS

I actually love those kinds of businesses. They’re never gonna go away. A lot of digital tools may come and go, but a tree trimming service will virtually always be here. The thing that’s changed over the past ten years is that the really good players are both good at executing their trade and good at executing digital marketing.

It’s becoming necessary to stand above the crowd and to get the leads first. I’m a member of a group that has a wedding photographer in it, and that wedding photographer is spending...