In this episode of Booked Out with Bre, I have the absolute honor and privilege of sitting down with a true legend, Lesley Pyle. Lesley is the founder of HireMyMom, and I truly consider her the "godmother" of the virtual assistant industry. She has been pioneering the work-from-home movement for 30 years—long before "hybrid work" was a buzzword or social media even existed!
Lesley shares her incredible story of transitioning from a corporate PR career to becoming a freelance trailblazer after her first daughter was born. We dive into the "old school" days of the industry, where newsletters were printed and licked by hand, and interviews were done over hardlined phones. Lesley’s longevity in this space is a masterclass in reading the market, trusting your gut, and staying committed to a mission that is bigger than yourself.
Here is what I dive into with Lesley:
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The catalyst that shifted her from a corporate-driven mindset to a "mom on a mission" to work from home.
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What the day-to-day of a virtual assistant looked like in the 90s (you won’t believe the technology gap!).
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Why moms are the ultimate business asset due to their innate drive, resourcefulness, and deep appreciation for flexibility.
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The 20-year evolution of HireMyMom and her "Match.com" vision for connecting talent with founders.
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Her honest reflections on the struggles of building tech, including finding web developers with true integrity.
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Where the virtual assistant industry is headed and why the rise of AI actually makes human connection and authenticity more valuable than ever.
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The role of faith and prayer in sustaining a business for three decades.
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A fun rapid-fire round where we talk Tex-Mex, skincare, and her favorite business leaders.
If you are a virtual assistant or a founder looking to understand the roots of this amazing industry, this conversation is pure gold. Lesley has paved the way for so many of us to have "yes lives" in motherhood, and I am so excited for you to hear her wisdom!
Episode Outline:
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Introduction: Meet Lesley Pyle, the Godmother of the Virtual Assistant Industry (00:02)
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Lesley’s Backstory: From Corporate PR to Realizing Daycare Wasn't an Option (01:04)
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The Early Days: Starting a Virtual Assistant Business Before Social Media and Email (02:49)
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The Evolution of Home-Based Working Moms and the Birth of HireMyMom (03:20)
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Virtual Assistant Life in the 90s: Hardlined Phones and Physical Newsletters (05:32)
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Why Motherhood is the Ultimate Training Ground for Business Owners (07:06)
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The Invaluable Worth of Freedom and Flexibility for Modern Moms (07:53)
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Navigating 20 Years of Growth and the Struggle of Web Development (09:19)
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Launching a Custom Web App in the Age of AI (11:10)
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The Shift in Hiring: What Companies are Looking for in Virtual Talent Today (13:02)
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Specialization and Niche Roles within the Virtual Assistant Industry (15:08)
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Crystal Ball: Where the Virtual Assistant Industry is Headed Next (16:53)
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AI vs. Human Connection: Why Authentic VAs are the Future (18:18)
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The Secret to Longevity: Prayer and Resilience through the Valleys of Business (20:47)
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The generational ripple effect of helping moms work from home (24:12)
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Leadership Lessons: Appreciation, Communication, and Avoiding Micromanagement (25:40)
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Rapid Fire: Favorite Books, Clean Skincare, and Tex-Mex (28:45)
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Final Words of Wisdom: Following Your Passion as a Virtual Assistant (30:52)
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How to Connect with Lesley Pyle and the HireMyMom Community (31:55)
Connect with Lesley:
Website:
https://www.hiremymom.com/
LinkedIn:
https://www.linkedin.com/in/lspencerpyle
Ways to Work with Me:
Follow Me on Instagram
https://www.instagram.com/heyitsbrecain/
Mom X VA Free Facebook Community
https://www.facebook.com/groups/momxva
Apply for the VA Leadership Academy
https://caincollectivellc.com/valaapplication
Book a Free Dream Team Design Session (for founders building with Team)
https://www.breannacain.com/iconandlightningbookacall
If you enjoyed this episode, I would love it so much if you left a rating and review! This helps us reach more women looking to become a virtual assistant, book out their business, and scale beyond their wildest dreams.
