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EP314: How to Hire Your First Virtual Assistant (Without Getting Burned) with Lesley Pyle

BootstrapMD - Physician Entrepreneurs Podcast with Dr. Mike Woo-Ming

Release Date: 10/08/2025

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BootstrapMD - Physician Entrepreneurs Podcast with Dr. Mike Woo-Ming

This episode is sponsored by . Lightstone DIRECT invites you to partner with a $12B AUM real estate institution as you grow your portfolio. Access the same single-asset multifamily and industrial deals Lightstone pursues with its own capital – Lightstone co-invests a minimum of 20% in each deal alongside individual investors like you. You’re an institution. Time to invest like one. _____________   This Episode is also sponsored by Ryze Health Every minute counts in medicine—so why waste it on clunky admin work? With Ryze Health, practice management becomes effortless. Our all-in-one...

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This episode is sponsored by . Lightstone DIRECT invites you to partner with a $12B AUM real estate institution as you grow your portfolio. Access the same single-asset multifamily and industrial deals Lightstone pursues with its own capital – Lightstone co-invests a minimum of 20% in each deal alongside individual investors like you. You’re an institution. Time to invest like one. _____________  This Episode is also sponsored by Ryze Health Every minute counts in medicine—so why waste it on clunky admin work? With Ryze Health, practice management becomes effortless. Our all-in-one...

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BootstrapMD - Physician Entrepreneurs Podcast with Dr. Mike Woo-Ming

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BootstrapMD - Physician Entrepreneurs Podcast with Dr. Mike Woo-Ming

This episode is sponsored by . Lightstone Direct LLC connects you to institutional-quality real estate investments backed by a $12-billion AUM firm that co-invests alongside you—your partner in building lasting wealth. All investments involve risk.  Please visit for a full list of disclosures. _________ This Episode is also sponsored by Ryze Health Every minute counts in medicine—so why waste it on clunky admin work? With Ryze Health, practice management becomes effortless. Our all-in-one platform streamlines scheduling, patient communications, and insurance verification,...

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BootstrapMD - Physician Entrepreneurs Podcast with Dr. Mike Woo-Ming

This episode is sponsored by . Lightstone Direct LLC connects you to institutional-quality real estate investments backed by a $12-billion AUM firm that co-invests alongside you—your partner in building lasting wealth. All investments involve risk.  Please visit for a full list of disclosures. _________ This Episode is also sponsored by Ryze Health Every minute counts in medicine—so why waste it on clunky admin work? With Ryze Health, practice management becomes effortless. Our all-in-one platform streamlines scheduling, patient communications, and insurance verification, giving you...

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BootstrapMD - Physician Entrepreneurs Podcast with Dr. Mike Woo-Ming

This Episode is sponsored by Ryze Health  Running your own practice shouldn’t mean struggling with rising health insurance costs. That’s why a physician designed Ryze Health Premium Insurance—exclusive coverage crafted for independent doctors, their teams, and families. Imagine lowering costs while gaining the freedom to focus fully on patients and the people who matter most. Discover how much you could save at ryzehealth.com and join the growing network of doctors choosing smarter coverage.  Follow @RyzeHealth on Instagram and LinkedIn. _________________    Can...

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BootstrapMD - Physician Entrepreneurs Podcast with Dr. Mike Woo-Ming

This Episode is sponsored by Ryze Health  Running your own practice shouldn’t mean struggling with rising health insurance costs. That’s why a physician designed Ryze Health Premium Insurance—exclusive coverage crafted for independent doctors, their teams, and families. Imagine lowering costs while gaining the freedom to focus fully on patients and the people who matter most. Discover how much you could save at ryzehealth.com and join the growing network of doctors choosing smarter coverage. Follow @RyzeHealth on Instagram and LinkedIn. __________ Why do physicians work 60-hour...

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BootstrapMD - Physician Entrepreneurs Podcast with Dr. Mike Woo-Ming

This Episode is sponsored by Ryze Health  Running your own practice shouldn’t mean struggling with rising health insurance costs. That’s why a physician designed Ryze Health Premium Insurance—exclusive coverage crafted for independent doctors, their teams, and families. Imagine lowering costs while gaining the freedom to focus fully on patients and the people who matter most. Discover how much you could save at ryzehealth.com and join the growing network of doctors choosing smarter coverage. Follow @RyzeHealth on Instagram and LinkedIn. __________________ How can physicians make the...

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This Episode is sponsored by Ryze Health 

Running your own practice shouldn’t mean struggling with rising health insurance costs. That’s why a physician designed Ryze Health Premium Insurance—exclusive coverage crafted for independent doctors, their teams, and families. Imagine lowering costs while gaining the freedom to focus fully on patients and the people who matter most. Discover how much you could save at ryzehealth.com and join the growing network of doctors choosing smarter coverage. 

Follow @RyzeHealth on Instagram and LinkedIn.

_________________

 

 Can hiring a virtual assistant transform your entrepreneurial journey? 

In this episode of Bootstrap MD, Dr. Mike Woo-Ming sits with Lesley Pyle, as she discusses her 30-year evolution in remote work, starting from 1996 as a freelancing mom. Drawing from her experiences in PR, motherhood, and building virtual networks, she explores barriers entrepreneurs face—time constraints, trust issues, and hiring fears—and how platforms like hers connect businesses with talented remote professionals. Lesley offers practical ways to outsource tasks, create SOPs, and build efficient teams, fostering growth through delegation and work-life balance. 

Top 3 Takeaways: 

  •  Identify and Outsource Time -Draining Tasks: Track daily activities like email or scheduling, estimate hours spent (e.g., 10 hours/week), and hire a virtual assistant to handle these, freeing time for patient care or strategic growth.

  • Leverage Trusted Platforms for Hiring: Use services like HireMyMom.com to find vetted professionals with skills in bookkeeping, social media, or project management; conduct interviews and trial periods to ensure alignment with your practice’s needs.

  • Prevent Burnout Through Delegation: Regularly assess where you’re overextended, consult family or mentors for perspective, and outsource non-core tasks to maintain faith, family, and personal well-being alongside business success.



About the Show:

Bootstrap MD is the ultimate podcast for physician entrepreneurs looking to escape traditional healthcare and control their financial futures. Hosted by Dr. Mike Woo-Ming, a successful physician, entrepreneur, and investor, the show delivers actionable insights on starting businesses, creating passive income, and navigating healthcare entrepreneurship. Featuring interviews with industry leaders, physicians, and experts in telemedicine and digital health, it’s your guide to building a profitable, fulfilling career. 

Tune in weekly at  http://bootstrapmd.com 

About the Guest: 

Lesley Pyle is the founder and CEO of Hire My Mom, with a Master’s in Public Relations and Marketing. Named one of 50 Women Entrepreneurs Who Inspire Us by Self-Made Magazine, she has 30 years of experience helping moms find remote work and small businesses hire virtual talent. Starting with Home-Based Working Moms in 1996, she empowers professionals to balance career and family through flexible opportunities. 

 Connect with Lesley Pyle:

 Website: HireMyMom.com 

LinkedIn: linkedin.com/in/lspencerpyle

Instagram: https://www.instagram.com/lesleypyle 

 

About the Host:

Dr. Mike Woo-Ming has over 20 years of experience as a physician entrepreneur. He’s built and sold multiple seven-figure companies and now leads Executive Medical, a group of clinics specializing in age management and aesthetics. Through BootstrapMD, he mentors physicians in business, content creation, and autonomy.

Let’s Connect: www.https://www.bootstrapmd.com 

 Want to start a podcast? Check out the Doctor Podcast Network!