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What can one question change? For Episode 150 of The Rapport by LilyGrace Podcast, I’m going solo to reflect on what 150 episodes, hundreds of conversations, and approximately 2,250 questions have taught me about the art of asking better questions. I started this podcast in 2020 during COVID, and what began as a creative project has evolved into something much bigger: a way to build rapport, create meaningful relationships, learn from people, and connect ideas across business and life. Over 150 episodes, I’ve learned that asking the right question can open a door, deepen a relationship, uncover an opportunity, change the direction of a conversation or even change your life. In this episode, I’m talking about: Why asking better questions is one of the most powerful communication skills you can develop How asking questions has shaped my personal and professional relationships Why the best salespeople aren’t necessarily the ones who talk the most—they’re the ones who listen and ask the right questions The importance of follow-up questions and why the fortune is in the follow-up Learning to recognize reciprocity and understanding who deserves access to you Attracting vs. chasing relationships, opportunities, and success How asking questions has helped me become more strategic in business and in life What happens to human connection when we can ask AI almost anything Why AI can provide answers, but it can't replace the human connection created when you genuinely want to understand another person Why you should never be afraid to reach out, ask a question, and start a conversation After 150 episodes, I’ve realized that the art of asking questions isn't about having the perfect question. It’s about being curious enough to listen, ask the follow-up, and see where the conversation takes you. Because one question can start a conversation. A conversation can create rapport. Rapport can create a relationship. And a relationship can change your life. What is one question that changed your life? Instagram @rapport.by.lilygrace @lilygraceyork Show Notes www.lilygraceyork.com Purchase BRAND[ED] The Road to Influence Course https://www.lilygraceyork.com/branded Code BRANDED15 for 15% Off

What if the key to becoming a better leader, entrepreneur, and high performer isn't doing more, but doing less with intention? In this episode of The Rapport by LilyGrace Podcast, I sit down with Katie McDonald, speaker, executive coach, and founder of the b.nourished planner, to discuss why self-care isn't selfish; it's your responsibility. After experiencing severe burnout that impacted both her physical and mental health, Katie left her corporate career and completely transformed the way she approached work, wellness, and success. Today, she helps high-achieving women and leaders break free from the burnout cycle by creating intentional habits that lead to greater energy, focus, and fulfillment. Together, we explore the difference between surviving and truly thriving, why so many ambitious professionals wait until they're completely exhausted to make a change, and how small, foundational habits can create extraordinary transformation over time. We also discuss the power of vision boarding your future, setting healthy boundaries at work, clearing out the excess that drains your energy, and asking one simple question each day: "What do I need today?" In this episode, we cover: Katie's personal burnout and recovery journey Why self-care is essential for leadership and long-term success How to prevent burnout before it happens The stigma surrounding self-care in today's culture Setting healthy boundaries at work and at home Building foundational habits that improve your life The philosophy behind the b.nourished planner Why future leaders must prioritize their well-being Clearing mental and physical clutter to create more focus How intentional living leads to a more meaningful legacy Whether you're an entrepreneur, executive, business owner, or someone who constantly feels overwhelmed by the demands of life, this conversation offers practical tools to help you reclaim your energy, protect your peace, and lead with greater purpose. Because the most impactful leaders don't sacrifice themselves for success—they build a life that allows both to coexist. Purchase the Planner:  https://shop.bnourished.com/pages/products  Connect with Katie McDonaldWebsite: https://katiemcdonaldspeaking.com/ If this episode inspired you, be sure to subscribe to The Rapport by LilyGrace Podcast for more conversations on leadership, entrepreneurship, personal growth, mindset, wellness, and building a life and career with intention. Instagram @rapport.by.lilygrace  Show Notes www.lilygraceyork.com Purchase BRAND[ED] The Road to Influence Course https://www.lilygraceyork.com/branded Code BRANDED15 for 15% Off

What separates business owners who build scalable companies from those who stay trapped working in their business? In this episode of The Rapport by LilyGrace Podcast, I sit down with Michael Rabinowitz, attorney, executive coach, mentor, father, husband, and board member of International Business Solutions, one of the largest small business consulting organizations in the United States. This conversation is a masterclass on the parts of entrepreneurship that aren't glamorous, but determine whether a business succeeds or fails. We dive into the "business of the business": finance, accounting, taxes, legal strategy, valuation, leadership, risk management, and why so many entrepreneurs are overenthusiastic but undercapitalized. Michael shares the mindset shifts every entrepreneur must make to stop letting their business run them and start building a company that creates freedom, wealth, and long-term impact. Beyond business strategy, we discuss mentorship, lifelong learning, intelligent conversations, leadership, and why success is built on integrity, healthy boundaries, and surrounding yourself with trusted advisors. The formula for scaling a business Why most businesses fail to grow The financial foundations every entrepreneur should understand How risk, liability, valuation, and capital affect growth Why education without action creates no results The importance of building a trusted team of advisors How to make better business decisions with confidence The difference between playing to win and playing not to lose Why lifelong learning is one of the greatest competitive advantages in business As a bonus, Part Two features Tyler Burgess, President of International Business Solutions, and Tonia Etoh, CFO, who share the remarkable legacy of their father—the founder of the company—and how they've carried that vision forward while leading one of the nation's most respected small business consulting firms. Whether you're launching your first company, growing an established business, or simply want a practical business education, this episode is filled with actionable insights that can change the way you think about entrepreneurship. If you've ever wished someone had taught you how to actually run a business, this conversation is for you. https://www.isi-services.com/  Instagram @rapport.by.lilygrace  Show Notes www.lilygraceyork.com Purchase BRAND[ED] The Road to Influence Course https://www.lilygraceyork.com/branded Code BRANDED15 for 15% Off LISTEN AND WATCH HERE Youtube Video Podcast

#147 In this episode, I’m joined by Chief Product Officer MaiLinh Ho of Gateway to discuss her journey into entrepreneurship and building in the fast-paced world of AI startups. At Gateway, the mission is simple: smarter training, faster growth. As an enterprise AI learning platform, Gateway transforms SOPs and tribal knowledge into short, interactive learning journeys helping teams reduce ramp time and improve performance across onboarding, training, and customer education. MaiLinh shares how her Vietnamese background and personal experiences shaped her path into tech, what it’s like working alongside her sister as cofounders, and the realities of scaling an AI-driven business in today’s evolving landscape. We also explore the future of work, the evolving role of AI in business, and what it truly takes to grow a startup from the inside out while staying grounded through it all. If you’re interested in entrepreneurship, AI, startups, and building something meaningful with impact, this episode offers an insightful and honest perspective. REFERENCES MaiLinh on  Linkedin https://www.linkedin.com/in/mailinhtranho/  Visit Gateway to learn more: https://careergateway.io/  Instagram @rapport.by.lilygrace  Show Notes www.lilygraceyork.com Purchase BRAND[ED] The Road to Influence Course https://www.lilygraceyork.com/branded Code BRANDED15 for 15% Off

In this episode we explore how AI is shaping the future of business, marketing, and everyday life through three distinct expert perspectives. This conversation brings together leaders across industries to share how they are integrating AI into their workflows, decision-making, and long-term vision and what it all means for the future. Lucas Machado: Exploring how AI can enhance lifestyle, streamline small business systems, and improve efficiency. From building agents to integrating tech into everyday workflows, Lucas shares how innovation can support both productivity and wellness. Connect with Lucas:www.curbsinc.netLinkedIn: https://www.linkedin.com/in/lucas-machado-857903134/https://www.modernwellspa.com/ Instagram: @curbsstudio @modernwellspa_ma Monique Lecomte: Offering a global leadership perspective on how AI is transforming daily workflows, independent business ownership, and experimentation. She shares the reality of building a business solo and how AI can act as a powerful tool for thinking, creating, and scaling. Connect with Monique:https://moniquelecomte.com/https://www.the-expert-generalist.com/ Instagram: @moniquelecomte_elevatingothers Dawn Gagye: Diving into the psychology of AI through a marketing lens. As a strategic marketing consultant, Dawn breaks down how AI is shifting the marketing industry and how individuals and businesses can thoughtfully embrace it. Connect with Dawn:https://www.tracerstrategicmarketing.com/ Linkedin: https://www.linkedin.com/in/dawngagye/ Instagram: @dawngagye Take The AI Readiness Assessment: http://marketing.wsiworld.com/ai-readiness?utm_source=podcast&utm_campaign=dawn-gagye&utm_medium=podcastnotesLG In this episode, we cover: How AI is impacting business operations and personal productivity The role of AI in solo entrepreneurship and decision-making The psychological and strategic implications of AI in marketing How to thoughtfully integrate AI without losing human connection What the evolving future of AI means across industries If you’ve been curious about how AI is actually being used and where it’s all heading this conversation offers real-world insight from three unique perspectives.

As 2025 comes to a close, this solo episode of The Rapport by LilyGrace Podcast reflects on the mindset shifts that shaped my year—and what I’m intentionally carrying into 2026. I share the three things I’m leaving behind: living in constant execution and survival mode, chasing validation instead of purpose, and people-pleasing in relationships that feel draining or misaligned. This episode explores what it looks like to move from hustle to flow, from proving to serving, and from ignoring intuition to fully trusting it. I also unpack the three values I’m taking into the new year: walking away from what no longer serves me, embracing imperfect and evolving relationships, and learning to slow down and enjoy the present moment. From career and business changes to relationships, rebranding, and growth, this year challenged me to let go, trust myself, and step into a more grounded version of success. In this episode, we cover: Execution vs. creation and feminine vs. masculine energy Purpose-driven work and authentic personal branding Releasing people-pleasing and trusting your intuition Letting go of the pressure to be “finished” Shifting from a get mindset to a give mindset Presence, confidence, and enjoying the process If you’re entering a new chapter or craving more intentional growth in your life, career, or relationships, this episode is for you.

In this episode of The Power of Collaboration Podcast, marketing strategist Dawn and creative implementer LilyGrace dive deep into the intersection of strategy, execution, and authenticity in business. From discussing the timing of marriage and career milestones to sharing stories of resilience, relationships, and personal growth, they explore how real-life experiences shape the way they lead and collaborate. Together, they break down their Dynamic Duo Marketing Model—where Dawn crafts data-driven strategies and LilyGrace brings them to life through targeted implementation. Listeners will learn how to bridge the gap between vision and execution, optimize small business marketing through delegation and AI, and leverage collaboration for growth across platforms like TikTok, LinkedIn, and Instagram. Tune in to hear how they turn strategy into results, why authentic vulnerability builds trust in business, and how you can book your own Dynamic Duo Strategy Session to elevate your brand. To learn more about our dual Offer click here to sign up for our 1 hour marketing session for $495: https://marketingblueprint.pro/sdmmhome-page  REFERENCES Instagram @rapport.by.lilygrace @tsmblueprintpro Show Notes www.lilygraceyork.com Purchase BRAND[ED] The Road to Influence Course https://www.lilygraceyork.com/branded Code BRANDED15 for 15% Off

Curious about how to actually use AI as a creative entrepreneur — without losing your originality? This episode is your beginner-friendly blueprint for blending AI with your side hustle to save time, spark creativity, and build a more scalable brand. Whether you’re feeling overwhelmed, intimidated, or just AI-curious, this conversation will help you reframe your relationship with technology and start using it as your creative sidekick. We’ll bust common myths about AI, explore how it enhances rather than replaces creativity, and share specific tools and workflows you can start using today — from content batching to branding to course creation. "AI won’t replace you. But a human using AI might." This Episode Is For You If You Want To: Save time in your side hustle or small business Turn creative blocks into breakthrough ideas Use tools like ChatGPT, Canva AI, or Notion AI but don’t know where to start Scale your marketing without outsourcing your vision Stay relevant in the fast-changing world of digital entrepreneurship What You’ll Learn: Why now is the perfect time to lean into AI Discover the cultural and economic shifts making AI essential for side hustlers and solopreneurs. How AI and creativity work together From writing Instagram captions to brainstorming your next big offer, learn how AI can unlock more originality, not less.  What a “Fusion Strategy” looks like Use AI for structure and efficiency, while preserving the soul and storytelling that make your brand unforgettable. Practical AI use cases for branding and marketing How to batch content, generate brand messaging, create content calendars, and launch smarter — in a fraction of the time. REFERENCES Instagram @rapport.by.lilygrace @lilygraceyork  Show Notes www.lilygraceyork.com Purchase BRAND[ED] The Road to Influence Course https://www.lilygraceyork.com/branded Code BRANDED15 for 15% Off

Welcome to the Rapport by LilyGrace Podcast. I have officially rebranded the show after six years and 141 episodes. I am excited to shift and bring new life to the podcast focusing on bringing value to you and your life and business.  In this kickoff episode of Rapport by LilyGrace, I’m diving into the story behind the podcast rebrand — why I chose the word Rapport and how building authentic connection is at the heart of any successful personal brand. You'll learn why branding is more than just marketing; it's about how you make people feel. I’m also sharing how intentional design, creativity, and real relationships have shaped my business and personal growth. What you’ll learn: ✨ The meaning behind Rapport and why it matters in brand building ✨ How to move from marketing yourself to becoming your brand ✨ The role of authentic connection in growing your business ✨ Why design is a powerful communication tool for your brand ✨ What’s coming next — interviews, solo episodes, and deep branding dives Networking, the fortune is in the follow up, and more tips and tricks. If you’re a creative entrepreneur, brand builder, or lifestyle-driven founder, this podcast is your new go-to space to stay inspired and aligned. REFERENCES Instagram @rapport.by.lilygrace @lilygraceyork  Show Notes www.lilygraceyork.com LISTEN AND WATCH HERE Youtube Video Podcast

Meet Samantha G., founder of Intuition Kicks, a sneaker brand rooted in resilience, self-trust, and the power of listening to your inner voice. In this episode, Samantha opens up about her personal journey—one marked by anxiety, self-doubt, and eventually, radical transformation. From therapy and journaling to discovering strength in a spin class sanctuary, she shares how her healing path sparked the creation of Intuition Kicks. What started as a vision during a spin class turned into a powerful movement—one that encourages women to follow their intuition and live boldly. Within just one year, Samantha turned a soulful idea into a tangible product with impact. We talk about: What it means to trust your gut (even when it's scary) to leave a marriage Building a brand with intention and soul Creating connection and confidence through style The power of movement—physically and emotionally How Samantha brought a product to life from scratch in a year This episode is about more than sneakers—it’s about stepping into your power and embracing your Intuition Era. REFERENCES to pre-order the shoes https://intuitionkicks.com/  Instagram @intuition_kicks @samanthat_gio

Dr. Jia, the Founder of Phyzix PT,  joins me to share how he’s redefining physical therapy by taking a holistic, nervous-system-based approach to healing chronic pain. Traditional PT is great for acute injuries—but when it comes to lingering pain without a clear cause, it often falls short. That’s because the root of the issue is often far from where the pain shows up. At PhyziX, Dr. Jia and his team look at the body as one interconnected system. They help patients identify hidden compensation patterns that develop after injury and often go unnoticed—yet lead to long-term discomfort. Using a 3-Step Method, they retrain the nervous system to restore natural movement patterns, not just relieve symptoms—so pain doesn’t keep coming back. He talks about how to have the right mechanics in this modern era where we are glued to our screen and also talk about how children’s developmental milestones are key to a balanced and healthy nervous system. REFERENCES https://www.phyzixpt.com/  Instagram @dr.jiali  and  @phyzix.pt

Discover how cold exposure can change your life from the inside out. In this episode, Rachel Lee, founder of Ice Bath Boston, shares her transformative journey of healing anxiety, improving sleep, and boosting performance—through the power of breath and ice baths. Learn how to find safety in your body and mind, explore the science of breathing mechanics, and understand how cold exposure rewires the nervous system to release trauma, reduce stress, and improve relationships. Whether you're an athlete, a high achiever, or someone navigating healing, Rachel breaks down how to build resilience, regulate your nervous system, and live sustainably as a peak performer. Learn what type of breather you are…your breath is your barometer.  Topics covered: Benefits of cold exposure therapy for anxiety, trauma, and sleep Breathing techniques to reset your nervous system How to release stress and boost emotional regulation Living sustainably while performing at your highest level Tune in to learn how to breathe deeper, feel better, and perform stronger—starting with cold. REFERENCES Instagram: @rachellee.health @icebathboston https://icebathboston.com/

Dacey and Rianna are on the podcast to debut their first album together, “And By This, I Live”. Two Berkley musicians fell in love and created a beautiful relationship which blossomed into a music collaboration and new album. Dacey and Rianna perform two powerful tracks from their debut album And By This, I Live and open up about the journey that brought the project to life. In this episode, we explore themes of spirituality, presence, and the courage it takes to fully embrace your creative calling. They walk us through their artistic process—from the spark of inspiration to the final notes—and reflect on how their individual paths intertwined to create something deeply meaningful. Their story is a testament to trusting the process, honoring your gifts, and allowing creativity to lead. The two songs, “Remember You’re Here” and “Blue” are sung by Dacey Black and accompanied by Rianna Kopcho focusing on being in the present and healing your past. This conversation dives deep and tells the story behind the music.  REFERENCES Instagram: @daceyandrianna  Spotify Album: And By This, I Live ⁠https://open.spotify.com/album/1sjdLR2NNxiTBa9IK3uydu?si=wD_GRNMyRIe82vplUKET1w&nd=1&dlsi=298a92c5ffe24920⁠ LISTEN AND WATCH HERE ⁠Youtube Video Podcast

Welcome to BRAND[ED], your go-to destination for personal branding education! Hosted by Samantha Newman and LilyGrace York, this podcast takes you behind the scenes of creating our BRAND[ED] Course: The Road to Influence—a step-by-step guide to building a powerful personal brand both online and in person. If you’re struggling to position yourself, gain visibility, or establish credibility, this course is for you. Whether you're still refining an idea, preparing to launch, or already running your business, we’re here to help you craft a brand that stands out. Through a dynamic, multimedia learning experience, we blend psychology-backed research, strategic storytelling, and actionable insights to help you cultivate influence with authenticity. In this podcast, we’ll walk you through key course takeaways, branding strategies, and what to expect when BRAND[ED] launches in April 2025. REFERENCES Instagram: @brand_ed_course  @rapport.by.lilygrace @sami.newman www.lilygraceyork.com/branded-course-coming-soon  to join the waitlist

Kathleen Burns Kingsbury isn’t your average money mindset coach; she’s a pioneering force in the realm of women and money, setting her apart from conventional counterparts. With over 18 years of specialized experience, she’s dedicated herself to empowering women across finance, business, and entrepreneurship. As a mentor to female entrepreneurs, Kathleen offers invaluable guidance, drawing from her extensive background in wealth psychology and client communication. Her expertise extends to working with financial advisors, helping them navigate the complexities of wealth management while fostering stronger client relationships. Recognized by The New York Times, The Wall Street Journal, and others, Kathleen is the author of Breaking Money Silence®: How to Shatter Money Taboos, Talk More Openly about Finances, and Live a Richer Life, her most recent of five books on wealth psychology and financial communication. And she’s not all business—when she’s not trailblazing the field of women and wealth, she’s conquering ski slopes and exploring the great outdoors in Vermont, living life to the fullest. In this podcast, we talk about money personalities, how to negotiate your value, and how women entrepreneurs can use their uniqueness to become financially successful.   REFERENCES For more information, visit KBKWealthConnection.com “Breaking Money Silence”  bonus chapter https://www.breakingmoneysilence.com/book-bonus/ LISTEN AND WATCH HERE Youtube Video Podcast