FoundersAt The Helm

“What are you willing to give up to grow?”

James spent years chasing aggressive growth on 16- to 18-hour days, helping clients drive more than $350 million in revenue. Then he asked a harder question: what is generational wealth worth if it costs the time with the people you're building it for?

“Build a business that gives you your life back.”

Success doesn’t have to mean working more. After two decades in big-league sports marketing, Eric launched Mindstone during COVID — and now he’s building a business that’s scalable, predictable and gives him more time with his family.

“From expertise to scale: betting on an idea before anyone else did.”

How much would you bet on an idea you believed could protect people? Matt went from Marine, police officer and security consultant to software founder — backing his first product with his own money, and a second mortgage, before the market proved it would work.

“When the job no longer fits: rethinking work, talent and human potential.”

Sometimes you’re not bad at the job — the job is simply wrong for you. Jan went from top performer to “no longer performing” when her role changed around her, and turned that experience into Better Job Fit.

“Trust is the product: building a security company people depend on.”

In security, the real product is trust. Ariel grew The Draco Group from handwritten schedules into a company serving hundreds of clients — by listening first, understanding the problem, and building the right mix of people, protocols and technology.

“Betting on yourself: building a security company without losing the personal touch.”

At some point, every founder has to decide whether the business is a side project or the real thing. Troy left a guaranteed paycheck, went all-in on WTSA Security and grew it to more than 100 employees — without letting the people behind that growth become just numbers.

“AI won’t take your job — but someone using AI might.”

AI isn’t replacing good marketers — it’s eliminating repetitive work and raising the bar for everyone else. Greg explains how agencies can use AI to get more efficient while keeping strategy, relationships and human judgment at the centre.

“Grow the right way: trust, talent and scaling a security business.”

“You have to grow the right way.” Mike built Premier Risk Solutions from a bootstrapped startup into a multi-state security company, and explains why trust, pricing discipline, strong people and careful expansion matter more than chasing revenue.

“Scale fast, learn faster: franchising, AI and the future of work.”

Bennett helped take Dirty Dough from one location to roughly 100 in about two years — and learned that growth can outrun the systems underneath it. Now he’s putting AI agents to work across his business, and thinks your next employee might manage them.

“Stay the course: building an entertainment business through uncertainty.”

After Sony Pictures, 20th Century Fox and Disney, Brian launched BGE in June 2020 — in the middle of COVID, with no guarantee it would work. Today it connects major brands with entertainment properties across TV, film, licensing and IP.

“People before process: why leadership problems show up first.”

The numbers may look like the problem, but the real issue often starts with people. Dana explains why leadership, character, culture and strong systems decide whether a business can grow without the founder carrying everything.

“Letting go to grow: when the founder becomes the bottleneck.”

The hardest part of scaling may be letting go of the thing you built. Greg talks about perfectionism, founder dependency, building a global remote team, and his goal of a company that can run completely without him.

“Scaling beyond yourself: the people, systems and strategy behind growth.”

The bigger the company gets, the fewer problems should reach the founder. Kara, author of The Revenue Engine, shares what scaling Lead Coverage taught her about hiring, leadership, go-to-market strategy and AI.

“Growth is a system: how founders reach the next inflection point.”

Before you add AI, fix the company underneath it. Stefan explains why growth takes focus, stronger operating systems, the right talent, and the willingness to reinvent the business at every major inflection point.