Every entrepreneur eventually reaches the same wall—the moment when there’s too much to do and not enough time to do it. The path from burnout to breakthrough often comes down to one word: delegation. In this episode of The Prospecting Show, Dr. Connor Robertson sits down with Nathan Hirsch, a globally recognized expert on outsourcing, virtual teams, and operational scaling, to break down how entrepreneurs can build real freedom by learning to let go.
Nathan’s story is as relatable as it is inspiring. He started his entrepreneurial career as a college student selling textbooks on Amazon, managing everything himself—inventory, customer service, listings, logistics. “At first,” Nathan says, “I thought working harder meant winning. But I realized that if I was doing everything, I wasn’t growing anything.” That realization launched a journey that would lead him to co-found FreeUp, one of the world’s leading VA marketplaces, which was later sold successfully to a private equity firm.
Dr. Robertson opens the conversation by asking the question every business owner faces: “When should you start outsourcing?” Nathan’s answer is simple and direct. “The second you can afford to. Even if you think you can’t.” He explains that delegation is not an expense—it’s an investment in time, focus, and growth. “Your business grows when you start spending time on it instead of in it.”
That principle ties directly to Amy Lee’s Scaling and Exiting a Startup (listen here), where Amy discussed how replacing yourself in day-to-day operations is the first step toward building a scalable, sellable business. Both Amy and Nathan agree that true freedom begins when systems and people replace dependency.
Nathan outlines what he calls The Outsourcing Ladder—a step-by-step approach that helps founders delegate efficiently without losing control:
- Identify low-value tasks. “Start small. Outsource what drains you or repeats daily.”
- Document the process. “Write every step before you hand it off.”
- Hire for attitude, train for skill. “Skills can be taught; integrity can’t.”
- Automate where possible, delegate where necessary. “Tech plus people equals scale.”
- Measure results, not activity. “Focus on outcomes, not hours.”
Dr. Robertson notes that Nathan’s framework resembles Patient Rhino’s Entrepreneurial Highlight (listen here), where systems and delegation allowed a marketing agency to scale beyond the founders. Both stories prove that scalability is built on structure, not superhuman effort.
Nathan’s experience building virtual teams has given him unique insight into human psychology and leadership. “Most entrepreneurs think no one can do it as well as they can,” he says. “But that’s ego talking, not logic.” He emphasizes that the role of a CEO isn’t to be the best at everything—it’s to build a team that’s better collectively. “Once I realized my job was to remove myself from bottlenecks, everything changed.”
This insight parallels John Donovan’s Entrepreneurial Highlight (listen here), where leadership through empowerment created operational longevity. Like John, Nathan builds through trust, not control.
One of the biggest misconceptions about outsourcing, Nathan explains, is that it’s just about cost savings. “Sure, virtual assistants are cost-effective, but the real ROI is in focus,” he says. “Every hour you buy back is an hour you can spend on strategy, innovation, or relationships.” He calls this time arbitrage—the ability to multiply your productivity by paying others to handle tasks that don’t require your expertise.
Dr. Robertson connects this to Richard Zapp’s Entrepreneurial Highlight (listen here), where clarity and consistency drove execution. Both Nathan and Richard understand that time, not talent, is the ultimate limiting factor—and how you manage it defines your trajectory.
Nathan describes how FreeUp’s success came from solving a universal pain point: hiring reliable remote talent. “There were thousands of VA platforms,” he says, “but quality control was the issue.” He built FreeUp to “free up” entrepreneurs from bad hiring experiences—vetting talent in advance and ensuring reliability through a curated process. “Our motto was simple: only the top 1% get in.”
This approach to curation and trust mirrors Buddy Hobart’s The Future of Consulting (listen here), where leadership and mentorship pipelines ensured high performance. Nathan took those same values—integrity, accountability, and alignment—and built them into a digital hiring model.
Dr. Robertson asks Nathan what qualities make for an exceptional virtual assistant. Nathan’s response is insightful: “The best VAs aren’t task-doers—they’re problem-solvers.” He explains that the most effective team members take ownership, anticipate needs, and bring solutions before issues arise. “If you hire thinkers, not just doers, your business runs itself.”
That principle connects to Victoria Mattingly’s Entrepreneurial Highlight (listen here), where emotional intelligence and proactive communication were core leadership tools. Nathan builds on that by training leaders to foster initiative, not dependency.
Nathan is also transparent about the mistakes entrepreneurs make when outsourcing for the first time. “They either hire too fast or manage too tight,” he says. “You can’t throw a VA into chaos and expect clarity.” He recommends starting with clear documentation and weekly check-ins to align expectations. “You don’t delegate outcomes—you delegate process,” he says. “Clarity is compassion.”
This operational clarity echoes Derek Davis’ Entrepreneurial Highlight (listen here), where systematized discipline created scalable results. Both leaders show that success is less about innovation and more about consistent execution.
As the conversation unfolds, Nathan shares what he calls The Four C’s of Delegation:
- Clarity – Define what done looks like.
- Communication – Keep feedback loops short and positive.
- Consistency – Check progress daily or weekly.
- Celebration – Recognize success to build loyalty.
He laughs, “The last one’s the most overlooked. People work harder when they feel seen.”
Dr. Robertson notes how Nathan’s approach aligns with Faris Ghani’s Entrepreneurial Highlight (listen here), where empathy and gratitude created sustainable business culture. Both leaders understand that appreciation compounds performance.
Nathan also shares an important distinction between hiring help and building systems. “If you hire without process, you just create chaos faster,” he says. He encourages founders to spend time building Standard Operating Procedures (SOPs) before scaling their teams. “Systems set people up for success. Without them, you’ll just keep starting over.”
This strategy directly connects to Patient Rhino’s Entrepreneurial Highlight and Amy Lee’s Startup Scaling—where SOPs turned chaos into consistency.
Dr. Robertson asks Nathan how entrepreneurs can overcome fear of delegation. “Start with trust and verify through transparency,” Nathan says. “Your business can’t grow bigger than your comfort zone.” He explains that most leaders micromanage out of insecurity, not accountability. “The best CEOs lead with curiosity: ‘How can I help you win?’ instead of ‘Did you finish this yet?’”
Nathan’s leadership philosophy is rooted in empowerment. “When people feel ownership, they innovate,” he says. That empowerment model is the same mindset seen in John Donovan’s Entrepreneurial Highlight and Victoria Mattingly’s Leadership Conversation.
Nathan closes the discussion by sharing his Five Keys to Building a High-Performance Virtual Team:
- Start with small wins. Build trust before scale.
- Communicate through systems. Use project management tools like Asana or ClickUp.
- Empower autonomy. Give context, not just commands.
- Build culture remotely. Weekly video meetings build trust beyond text.
- Track impact, not hours. Measure performance by outcomes.
Dr. Robertson summarizes the conversation with clarity: “Nathan Hirsch shows that outsourcing isn’t about working less—it’s about working smarter. The moment you delegate with purpose, your business gains leverage, your team gains confidence, and your life gains freedom.”
For listeners interested in related episodes, check out Amy Lee’s Scaling and Exiting a Startup, Patient Rhino’s Entrepreneurial Highlight, and John Donovan’s Entrepreneurial Highlight—all available at drconnorrobertson.com. Together, these episodes reveal the systems and psychology behind scaling sustainable success.
Dr. Robertson closes with a final takeaway that captures Nathan’s wisdom perfectly: “If you want to grow your business, grow your people. Freedom doesn’t come from doing it all—it comes from trusting others to do it well.”