In this episode of Women of Wealth, Hawley Woods Gray and Allie Ramo welcome back returning guest Pam Cytron for a powerful conversation about entrepreneurship, creative funding strategies, and why employee benefits should be part of every startup’s growth plan.

Pam is a seasoned financial services leader, wealth tech entrepreneur, and founder of a nonprofit growth accelerator that helps emerging companies scale faster by connecting product builders with product buyers. With decades of experience building and advising startups, she brings a unique perspective on how founders can fund businesses, build strong teams, and think differently about financial strategy.

One of the most fascinating moments of the conversation is Pam’s personal story about funding her first startup using the cash value from her whole life insurance policy. Instead of relying on venture capital or family money, she leveraged the liquidity of her policy to access capital with flexible repayment terms, no dilution, and no outside approval. It’s a reminder that insurance isn’t just about protection—it can also be a powerful financial tool.

Pam also shares why entrepreneurship is a team sport, and why founders often make the mistake of waiting too long to offer employee benefits. Even basic benefits—like healthcare options or retirement plans—can dramatically improve focus, loyalty, and performance inside a startup environment. According to Pam, offering benefits is more than a cost—it’s a signal of leadership and stability.

The conversation also dives into:

• How founders can creatively fund businesses without giving up equity
• Why whole life insurance can become a flexible source of capital
• The mindset shifts every entrepreneur needs to succeed
• Why employee benefits are critical for startup retention and growth
• How today’s founders are learning business from influencers and social media
• The importance of failing fast and starting each day with a clean slate
• Why financial education and insurance planning are missing for many young entrepreneurs

Pam also challenges founders to think bigger about the role of insurance—not just for personal protection, but as part of a broader strategy for building resilient companies, protecting assets, and supporting employees.

For entrepreneurial women building businesses, this episode is packed with insight on how to think like a founder, protect your future, and build companies that support both growth and well-being.

Connect with Pam Cytron
Pam is currently recruiting companies for the next cohort of her nonprofit accelerator focused on helping founders scale faster through strategic relationships and growth support. https://www.pamelacytron.com/

For more awesome episodes visit our podcast website at WomenOfWealth@transistor.fm

Got a burning question or a topic you're itching to hear about? Slide into our DMs on Instagram at @Wowwomenofwealth. Now, let's turn those pennies into power moves!

In this episode of Women of Wealth...

Hawley and Allie sit down with Master Success Coach and founder of Lisa Listen, Lisa Bybee Ferrell, for a powerful conversation about building wealth from the inside out - starting with communication, clarity, and how we show up in our relationships.

With over three decades of experience in sales, broadcasting, and entrepreneurship, Lisa shares how her background in high-level sales shaped her philosophy: if you listen long enough, people will tell you exactly what they need. That skill — true listening — became the foundation of her coaching work with individuals and couples.

Together, they dive into:

• Why most couples avoid money conversations — and how that avoidance creates long-term damage
• The difference between listening to respond vs. listening to understand
• How Lisa rebuilt her voice after losing it in past relationships
• Clear communication strategies for couples who work together
• Setting “house rules” and “business rules” to protect both marriage and mission
• Why conflict isn’t the enemy — denial is
• How high-achieving women can succeed professionally without disconnecting at home
• The power of faith, humility, and vulnerability in leadership and love

Lisa shares practical tools couples can implement immediately, including setting financial discussion boundaries, checking for understanding during tough conversations, and creating intentional time to talk before resentment builds.

For the driven woman who feels successful at work but disconnected at home, this episode is a reminder: wealth isn’t just financial. It’s emotional, relational, and spiritual. And if something feels off, it’s not something to outrun — it’s something to address.

True leadership begins with self-awareness.
Strong relationships require intentionality.
And real wealth is built through clarity, communication, and connection.

🔗 Connect with Lisa

Learn more at LisaListen.com

• Discovery sessions available
• Books, card decks, and companion workbooks
• Personalized signed copies available
• Coaching for individuals and couples

For more awesome episodes visit our podcast website at WomenOfWealth@transistor.fm

Got a burning question or a topic you're itching to hear about? Slide into our DMs on Instagram at @Wowwomenofwealth. Now, let's turn those pennies into power moves!

In this episode of Women of Wealth, we take on one of the biggest financial pressures facing business owners today: rising healthcare costs - and what can actually be done about them. Healthcare premiums are climbing faster than wages. Deductibles are higher than ever. Employees are frustrated by surprise bills. Employers feel stuck in a system that increases in cost year after year with little transparency or control.

Inspired by The Great American Healthcare Heist, we unpack what’s really happening inside the healthcare system - from surprise billing and prescription pricing practices to profit-driven insurance models and the growing disconnect between patient care and corporate incentives. But this episode isn’t just about the problem. It’s about solutions!

We introduce WellthCare - a patent-pending model designed to work alongside existing health plans to reduce utilization, lower claims, and reward preventative care. Instead of waiting for illness to become expensive, WellthCare incentivizes proactive health engagement.

Employees gain access to:
• $0 copays for urgent care, primary care, virtual care, and mental health counseling
• Free lab work
• Zero-cost prescriptions through an owned pharmacy network
• Medical bill reduction tools that lower expenses by an average of 70%
• $1,100+ annually deposited into a SEP IRA
• $1,300–$2,800 per year in wellness-based store rewards
All with no disruption to the employer’s existing health plan and no out-of-pocket cost to the employer or employee.

Designed for businesses with 10+ W2 employees paying into FICA, this model leverages existing tax credits that reward preventative care and retirement contributions - aligning health and wealth in one strategic benefit structure.

If you’re a business owner looking to reduce long-term healthcare increases, improve employee retention, and strengthen retirement outcomes, this conversation is for you. To learn more or explore whether WellthCare could benefit your company email us!

Hawley Woods Gray
📧 hawley@womenofwealth.vip

Allie Ramo
📧 allie@womenofwealth.vip

OR visit https://www.wellthcare.com

For more awesome episodes visit our podcast website at WomenOfWealth@transistor.fm

Got a burning question or a topic you're itching to hear about? Slide into our DMs on Instagram at @Wowwomenofwealth. Now, let's turn those pennies into power moves!