Rob Levin is the co-founder of Work Better Now, a company that provides full-time, high-performing virtual professionals from Latin America to small and midsize businesses across the US. A longtime serial entrepreneur and former media owner, Rob has helped thousands of business owners scale by freeing them from low-value tasks and building talent-driven cultures. He’s also host of the Great Talent Great Business podcast and author of The New Talent Playbook.
“Buy Back 2 Hours a Day: How Rob Levin Uses Virtual Assistants to Help Small Businesses Scale Faster” isn’t just a catchy title—it’s the core lesson of this episode. Virtual assistants for small businesses aren’t just a productivity hack—they’re a competitive weapon. In this conversation, Freddy D sits down with Rob Levin, co-founder of Work Better Now, to break down the exact systems and strategies that helped him escape 60-hour weeks, reclaim his life, and build an Inc. 5000 company powered primarily by referrals and Superfan clients.
Rob reveals how his partnership with his first assistant, Jessica, reshaped his calendar, expanded his strategy time, and ultimately transformed his entire business model—from one VA to a multi-role talent engine supporting sales, marketing, finance, customer service, and even construction estimating. You’ll hear how Work Better Now’s talent-first culture, frictionless hiring process, and commitment to relationship over transaction create unstoppable momentum for small and midsize businesses ready to get out of the weeds, scale faster, and finally start playing offense.
[00:00] Introduction – From New York stories to virtual assistants for small businesses
[01:12] Rob’s backstory – From Big Six accountant to serial entrepreneur and media owner
[02:54] The first Latin American assistant that changed everything (Jessica’s impact)
[06:05] Buying back two hours a day – Shifting from admin to high-value activities
[10:20] Why every business owner should have an assistant
[12:05] How Work Better Now’s model works: consult, role design, and 3-candidate precision match
[15:25] Talent-first philosophy and building an employer brand in Latin America
[19:08] Creating Superfans among talent and clients through relationships, not transactions
[22:55] Case studies: construction estimating, logistics, and professional services
[28:40] Culture, uniforms, and first impressions—why “director of first impressions” matters
[34:15] Remote recognition rituals and the power of public praise
[40:10] Rob’s book, podcast, and where to connect
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This conversation with Rob Levin is a masterclass in building a championship roster, not just filling seats. Rob didn’t just hire a virtual assistant—he rewrote his playbook. By delegating calendar chaos, travel details, and admin to Jessica, he freed up time for strategy, selling, and family—the true MVP activities for any owner.
What started as a single assistant evolved into Work Better Now, a talent engine that now supports over 40 roles, from sales and marketing to finance and estimating support in industries like construction, logistics, and professional services. The real edge? A relentless talent-first mindset—treating virtual talent like valued teammates, not disposable contractors. That’s how they’ve become #114 and then #642 on the Inc. 5000, powered largely by referrals and word-of-mouth introductions.
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The Action:
Document and delegate 20 recurring tasks to a virtual assistant within the next 7 days.
Who:
Business owner or senior leader of a small/midsize company.
Why:
Because you can’t fix what you won’t face. This simple move turns rumors into data, breaks the silence, and signals that you’re serious about improving company culture—not just giving speeches about it.
How
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