Rapport By LilyGrace

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