From Driveways to Five Companies: The Entrepreneurial Origin Story
Cory Blumenfeld was supposed to be a doctor. His grandfather was one, his aunt was one, and his family had mapped out a path that involved medical school and about ten more years of formal education. What actually happened was a final-year entrepreneurship course at Wilfrid Laurier University, a professor who had built and sold his own business, and a realization that Cory had been running informal operations since he was a kid washing cars in the summer and shoveling driveways in the winter. He dropped the pre-med track, built a business digitizing hospital patient education materials without any prior industry knowledge, and called those six years his real MBA. Two exits and nearly five million dollars raised later, he is now running BlueMoso from Mexico, matching business owners with virtual assistants based not just on skill sets but on communication style, personality, and how people actually work. His business partner and first VA, Shah Romero, runs operations from the Philippines. The whole thing started as a side hustle when other founders kept asking Cory why their VA relationships kept falling apart while his worked so well.
The Matching Problem Nobody Was Solving
What makes BlueMoso’s model distinct is the premise Cory kept returning to throughout the conversation: skill is not the hard part. You can find a technically capable virtual assistant without much trouble. What consistently breaks these working relationships is misalignment in personality, communication cadence, and work style, things that no job description captures and no resume reveals. BlueMoso runs assessments on both sides of the equation, interviewing and testing their talent pool while also profiling incoming clients to understand what kind of person they actually need around them, not just what tasks they want handled. Cory gave a sharp example from the week of recording, where a VA told a new client directly that it sounded like he needed someone to mother him and hold him accountable. The client’s reaction was that this was exactly what he needed to hear. That moment of trust, built in the first few days, is precisely what the matching process is designed to make possible. Every client also gets a team lead and access to BlueMoso’s executive team, with monthly feedback loops built in so mismatches get caught before they become expensive problems.
The Psychology of Letting Go
The most honest part of the conversation was about what actually stops business owners from getting help, and it is not the task list. Robin Ayoub, who has been running his own company and this podcast simultaneously for years, put it plainly: he could not have managed everything without his own virtual assistant, Sylvia, who has been working with him for more than three years from the Philippines. But the decision to bring someone into your working life at that level requires something that goes beyond logistics. Cory framed it with a question he now asks founders directly: could you take a sick day tomorrow and have things still run? Could you take a full week off without the business collapsing? If the honest answer is no, that is not a time management problem. That is a trust and control problem, and the only way through it is starting small, handing off the smallest possible thing first, and letting the relationship prove itself incrementally. He was equally direct about what BlueMoso is trying to fix on the other side of that equation, because virtual assistants have frequently been burned too, underpaid, ignored, or dropped without notice by clients in other countries who calculated that distance made accountability optional. Cory named that problem without softening it, and said changing it is a core part of why BlueMoso exists.
Where AI Fits and Where It Does Not
Cory pushed back against the easy narrative that AI will eventually make virtual assistants redundant. His read is that AI is actually expanding the outsourcing market by raising the capacity ceiling for small businesses. If you can work faster and take on more clients, you need more operational support, not less. What he sees BlueMoso’s talent pool doing is becoming the humans in the loop, managing AI tools, running systems, and handling the relationship work that no model is going to replace anytime soon. He was blunt about it: every time he ends up in an automated customer service flow, the first thing he asks for is a human. That instinct, he argued, is not going away. The episode is available now in full.
If this conversation made you think about how you are spending your time and whether the people around you are actually the right fit for how you work, the full episode is worth your time in either format. Watch on YouTube to catch the full exchange including the moments where Robin and Cory go well beyond the standard founder interview, or Listen on Simplecast if you prefer to take it in on your commute or, like our friend Esteban in Barcelona, on the treadmill.
Robin Ayoub 
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