In this episode of Listen Bitch Presents: Tell Me Why You’re Special, I sit down with Dale Montgomery, Director of Advanced Planning for a virtual family office, to talk about the hidden side of entrepreneurship, business growth, leadership, stress, delegation, tax strategy, nervous system regulation, and what success actually costs people behind the scenes.

Dale breaks down the concept of virtual family offices and explains why many entrepreneurs making $1M+ still feel overwhelmed, overworked, emotionally exhausted, and trapped inside businesses that depend entirely on them.

We discuss scaling challenges, delegation, limiting beliefs, burnout, mental clarity, decision fatigue, work-life balance, ego in entrepreneurship, and why focusing on “who, not how” changes everything for growing companies.

This conversation also dives into nervous system health, brain-heart coherence, stress management, breathwork, personal growth, leadership development, tax planning, liquidity, business independence, and the emotional realities many high performers quietly struggle with.

Dale explains how stress impacts creativity, relationships, problem-solving, and long-term business value — and why entrepreneurs need sustainable systems instead of nonstop hustle culture.

If you’re a business owner, entrepreneur, founder, coach, creator, or high achiever trying to scale without losing your mind, this episode is packed with practical insight and real conversations most people avoid having.

Dale is the Director of Advanced Planning at TRS Family Office and the author of The Virtual Family Office Advantage.

His work is built around a simple reality: the more successful a business owner becomes, the more complex their financial life gets, and complexity without coordination creates blind spots.

Dale helps business owners eliminate fragmented advice and move from siloed decision-making to a fully coordinated strategy. Through a Virtual Family Office and Team-Based Model, he serves as the strategic quarterback, bringing together elite specialists across five core areas, Tax Mitigation, Risk Management, Legal Services, Business Advisory, and Wealth and Legacy planning. The result is proactive, integrated planning designed to uncover opportunities, reduce inefficiencies, and protect long-term wealth.

He also works closely with CPAs across the country who want to evolve beyond the traditional referral model. Instead of sending advanced planning opportunities out the door, Dale helps CPAs expand their advisory impact, increase revenue per client, and deliver higher-level strategies to their A and B clients, all without adding staff or overhead.

By integrating coordinated advanced planning into the CPA relationship, he helps firms deepen client loyalty, elevate their role from tax preparer to strategic advisor, and build a more scalable, value-based practice

https://TRSFamilyOffice.com
Download the audio version of my book, The Virtual Family Office Advantage.
The book explains what coordinated planning looks like and how a Virtual Family Office model brings the right experts together across five key areas: tax planning, risk mitigation, wealth management, legal services, and business advisory. Listeners who feel like their situation is getting more complex will walk away with a clearer way to think about their decisions, and a better understanding of what “coordinated planning” actually means.

Schedule a 15-minute introduction call (optional).
If a listener wants help applying the ideas to their own situation, they can schedule a short call. The goal is not to sell anything on the call. It’s simply to learn what they’re trying to solve, answer a few questions, and see whether it makes sense to take the next step.

In this episode of Listen Bitch Presents: Tell Me Why You’re Special, I sit down with Marcy Axelrod for a deep conversation about fear, presence, emotional disconnection, parenting, authenticity, and how people truly “show up” in life.

Marcy shares her personal story of developing a stutter as a child after a major life transition and how that experience led her to study human behavior, emotional presence, and the ripple effect our energy has on other people. She breaks down her powerful framework of the three levels of showing up — from barely surviving to being fully present and connected.

We dive into nervous system overwhelm, anxiety, shame, parenting mistakes, emotional awareness, fear-based living, and how so many people are physically present but emotionally unavailable in their relationships and everyday life.

This conversation also explores authenticity, self-awareness, human connection, stress, emotional regulation, and the practical ways we can stop living reactive lives and start intentionally showing up for ourselves and the people we love.

Marcy also shares insights from her book How We Choose to Show Up and discusses why true presence changes not only your own life — but every room you walk into.

If you’ve been emotionally checked out, overwhelmed, disconnected, anxious, exhausted, or stuck in survival mode… this episode is going to make you think hard about how you’re showing up in your own life.

, she is a bestselling and award-winning author, TV Contributor, 2X TEDx speaker and visual artist. Her latest book, How We Choose to Show Up, is a #1 Bestseller, was recently awarded the Hayakawa Book Prize and has a cover endorsement by none other than Mel Robbins!.

Marcy has been interviewed in Forbes, Psychology Today, and The Marketing Journal, among others.

Her approaches have been tested and proven through projects with some of the world’s largest high-tech companies (e.g., HP, SAP, Cisco). With a background on Wall Street (Lehman Brothers) and in Silicon Valley, Marcy’s work has been highly praised by professors at Harvard, Yale, Stanford, Columbia, and Cornell.

Based on 20+ years of research, Marcy’s latest book, How We Choose to Show Up, presents in 3-D nature’s model of how humans are designed to Show Up to thrive. The resulting model is helping thousands of people connect more deeply with themselves, others and their experiences, adding meaning to their lives, and helping companies around the world to innovate and grow.

Showing Up integrates neuroscience, psychology, behavioral economics and evolutionary biology with top consulting strategies and leading business practices, to help people, companies and societies succeed.

https://choosetoshowup.com/

In this episode of Listen Bitch Presents: Tell Me Why You’re Special, I sit down with Jayna K. Palmer for a brutally honest conversation about trauma, self-sabotage, healing, accountability, and learning how to stop living trapped by the voices in your own head.

Jayna shares the life-changing moment where she woke up physically paralyzed and realized she had to confront the destructive mindset patterns that were keeping her stuck. We talk about negative self-perception, survival mode, personal ownership, emotional healing, and how faith and self-awareness can completely change the direction of your life.

This conversation dives deep into victim mentality, internal battles, unhealthy coping patterns, and the hard truth that healing starts when you stop blaming everyone else and finally face yourself honestly.

Jayna also shares her upcoming book Out of the Cave and discusses why vulnerability, transparency, and telling the truth about your story can help other people escape their own darkness too.

If you’ve ever felt trapped in fear, shame, depression, trauma, or self-destruction, this episode will challenge you to stop hiding and start rebuilding.

Jayna is not here to motivate you—she’s here to disrupt you.

An international speaker, author, and unapologetic truth-teller, she walks into rooms like a mirror people didn’t ask for but desperately need. If there’s a gap between the life you’re living and the life you keep talking about… she’s already standing in it, calling you out and calling you forward at the same time.

She didn’t build her message from theory. She built it from surviving what should’ve broken her—and then having the audacity to outgrow it. Trauma tried to write her story. She grabbed the pen, rewrote the ending, and now teaches women how to do the same—without excuses, without coddling, and definitely without staying comfortable.

Her work sits at the intersection of identity, truth, and ownership. She doesn’t just ask, “What happened to you?” She asks, “Whose voice are you still listening to… and how much is it costing you?”

Founder of movements that don’t play small and creator of frameworks that hit where it hurts (and heals), Jayna is known for one thing above all:

She will say the thing you’ve been avoiding—
and somehow make you feel powerful enough to finally face it.

“If you don’t like the truth… Change.”

https://www.facebook.com/ByFaithJaynaKpalmer

https://www.linkedin.com/in/jayna-k-p-908117101?utm_source=share&utm_campaign=share_via&utm_content=profile&utm_medium=ios_app