When Rob Cherun started his career at Morgan Stanley and McKinsey, he was on the fast track to a high-powered corporate career. But instead of climbing the well-worn path of investment banking and consulting, he took a leap into entrepreneurship; one that would see him transform a small video surveillance company into an industry powerhouse.
In the latest episode of The Next Moves Podcast, Rob sat down with host Joe Diubaldo to share how he navigated career pivots, scaled a business from $5M to $150M in revenue, and is now investing in the next generation of entrepreneurs through search funds.
Taking the Leap: From Finance to Founder
Rob’s career began in the world of finance and strategy, first as a consultant at McKinsey and later as part of Morgan Stanley’s executive office, restructuring the firm’s wealth management division. But despite the prestige, something was missing.
“Everyone I looked up to was a business owner or entrepreneur,” Rob recalled. “I realized that the real risk was not taking the risk.”
So, instead of taking a lucrative hedge fund job post-MBA, Rob raised a search fund, an investment model where backers provide capital for an entrepreneur to acquire and run an established business. That business? A Toronto-based video surveillance company called UCIT, which would later become Stealth Monitoring.
Scaling a Business: The Strategy Behind 30X Growth
Under Rob’s leadership, Stealth Monitoring grew from 50 employees to over 2,000 and expanded from a single Toronto office to 40+ locations across five countries. But how did he scale so effectively?
“The key was focus,” Rob explained. “Our competitors tried to be everything to everyone, but we specialized. We started with video monitoring for construction sites. Nothing else. That focus allowed us to become best-in-class.”
From there, Stealth expanded strategically, moving into industrial and commercial real estate, but always maintaining a clear value proposition. “We had to say no to big opportunities that didn’t fit our model,” Rob said. “That discipline allowed us to scale sustainably.”
Another major factor? Building the right team.
“You can’t do it all. The biggest mistake entrepreneurs make is not knowing how to delegate,” Rob noted. “Every year, I would ‘gift’ myself time by hiring someone better than me in a certain area. That freed me up to focus on what was next.”
Selling the Business and What Comes Next
After more than a decade of growth, Rob and his team made the decision to sell Stealth Monitoring in two stages: first to a private equity firm, and later to a strategic buyer. For investors, the return was staggering; over 9X on their initial capital, with compounding returns continuing to grow post-sale.
Following his exit, Rob faced a new challenge: what to do next.
“When you step out of the CEO role, you go from getting 500 emails a day to almost none. It’s a shock,” Rob admitted. “I realized I needed to figure out what the next mountain to climb was.”
For Rob, that next challenge is investing in search fund entrepreneurs, helping the next wave of ambitious operators buy and scale businesses just as he did.
Lessons for Founders & Leaders
Reflecting on his journey, Rob shared a few key takeaways for those looking to build and scale businesses:
🔹 Specialize and focus: Don’t try to be everything to everyone. Be the best at one thing first.
🔹 Hire smarter: Find people better than you, delegate, and empower them to lead.
🔹 Think ahead: The best returns come from patience, discipline, and compounding growth.
🔹 Be ready for change: Exiting a business isn’t just financial; it’s personal. Know what’s next.
Rob’s journey is proof that taking calculated risks can lead to outsized rewards. Whether you’re a founder, investor, or aspiring entrepreneur, his insights offer a roadmap for scaling with purpose.
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