Connecting the Dots with Jessica Caresse

Hosted by Jessica Caresse

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Aug 2026

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About the show

Becoming your best self is a life long journey with ups, downs, challenges, and the unknown. On Connecting the Dots, we discuss our life journeys to show the different challenges we had to overcome to get to where we are today. Sometimes discovering our purpose brings you back to a special place in your life that you didn't think had any significance. We touch on mindset, wellness, business, dreams, goals and spiritual journeys. Let's start connecting the dots in your life and see how you can transform into your best self. #connectingthedots #Inspiration #motivation #clarity #mindset

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60 recent

August 14, 202652 min

She Was Fired While Bedridden — Then Built an Empire on Her Own Terms with Suzzanna Ravenlight, PhD ·

She was bedridden for 9 months, working from her bed just to keep her job. They eliminated her position anyway.In this episode of Connecting the Dots, Jessica sits down with Dr. Suzzanna Ravenlight — organizational psychologist, executive leadership coach, and founder of Ravenlight Leadership Coaching, LLC — for an unusually candid conversation about intuition, burnout, corporate culture, and what it actually takes to stay yourself under pressure.Dr. Suzzanna shares the coin-flip exercise she teaches clients to distinguish fear from real intuition, opens up about being fired while seriously ill, breaks down why return-to-office mandates and micromanagement are backfiring on the very leaders enforcing them, and gets personal about the health battles — including six miscarriages and an ongoing autoimmune condition — that shaped how she coaches leaders today.This is a conversation about sovereign leadership, authenticity, and refusing to let any one chapter of your life define you.Dr. Suzzanna Ravenlight is an organizational psychologist, executive leadership coach, founder of Ravenlight Leadership Coaching, and author of The Space Between Thoughts. Through her work, she helps leaders and high-achieving professionals quiet the noise, reconnect with their inner wisdom, and lead with greater clarity, confidence, and authenticity.Drawing on more than 20 years of experience in organizational efficiency, leadership development, and human behavior, Dr. Ravenlight combines science, self-awareness, and transformational insight to help individuals navigate change, overcome limitations, and create lives and careers aligned with who they truly are.💼 LinkedIn: linkedin.com/in/suzzanna-ravenlight-phd 📸 Instagram: instagram.com/dr.suzzanna.ravenlight

July 3, 202658 min

The Cupcake War That Made Her Quit Baking Forever (True Corporate Story)

She's been "ruining the workplace" since 1997 — and she has zero regrets. Lori Lalonde spent nearly three decades in corporate tech, including senior leadership roles at Microsoft and Manulife, before walking away to build her own executive coaching practice for women.In this episode, Lori and Jessica dig into the moment a CEO told Lori to choose between her job and her kids, the town hall confrontation that got her called into a boardroom for an "apology," the cupcake incident that ended her office baking career forever, and the specific, practical boundaries — like refusing to answer messages immediately — that changed how she operates as a leader. They also unpack why so many women in corporate are burning out, why "office politics" isn't a dirty word, and what it actually takes to navigate power inside an organization built by people who don't look like you. Lori Lalonde is the CEO and founder of Her Executive Ascent, an executive leadership advisory practice for senior women in high-stakes organizations, and host of the podcast Leadership Recalibrated. Connect with Lori: Website: www.herexecutiveascent.com LinkedIn: Lori Lalonde https://www.linkedin.com/in/lorilalonde/ Podcast: Leadership Recalibrated (Spotify & Apple Podcasts) https://podcasts.apple.com/us/podcast... Follow Connecting the Dots with Jessica Caresse for more conversations on leadership, entrepreneurship, and building a career (and life) on your own terms.

May 1, 2026Episode 31 hr 26 min

The AI Platform Built From a Rooftop Conversation in Miami — The Indrasy Story

What does it actually take to build an AI platform from the ground up — for the people everyone else is ignoring?In this episode of Connecting the Dots, Jessica sits down with the full leadership team of Indrasy — CEO Kyle, CTO Rose, and CRO Athena — three first-generation Americans building an AI operating system designed specifically for small businesses.They get into how they met, what makes their platform different from ChatGPT and Claude, why South Florida's tech community is so fragmented, the real reason small businesses fail (hint: it's not the service), and what it actually means to build something that adds value instead of just extracting it.Whether you're a small business owner, aspiring entrepreneur, or just curious about where AI is really headed — this one's for you.🔗 Find Indrasy: https://indrasy.com 💬 If this episode resonated with you, like, subscribe, and share it with someone building something.

February 20, 2026Episode 246 min

⁠How I Quit the Police Force to Build a 6-Figure Assisted Living Business

In this episode of Connecting the Dots, Jessica Caresse talks with Carline Cadet-Francois (founder of FALC) about transitioning from the Sheriff's Office to a 6-figure Assisted Living Facility (ALF) owner. Learn the step-by-step process of starting a senior care business and shifting from an employee to an entrepreneur mindset. Watch this episode to learn: • How to start an assisted living facility in Florida. • The reality of hitting 6-figures in your first year of business. • Why investing in a business mentor is the fastest way to scale. • Overcoming a poverty mindset to build generational wealth. About Our Guest: Carline Cadet Francois is a healthcare entrepreneur and founder of Florida Assisted Living Consulting (FALC), where she helps professionals navigate licensing, compliance, and growth in the ALF industry. She leads the Thriving Circle Community, offering ongoing mentorship and support for ALF operators, and is the organizer of ALFCaregiverCon, Florida’s premier Assisted Living & Caregivers Conference. A former ALF administrator, Carline is passionate about equipping senior care leaders with the tools to build sustainable businesses rooted in quality care. Watch this episode to learn: • How to start an assisted living facility in Florida. • The reality of hitting 6-figures in your first year of business. • Why investing in a business mentor is the fastest way to scale. • Overcoming a poverty mindset to build generational wealth. Connect with Carline Cadet-Francois: • LinkedIn: https://www.linkedin.com/in/carline-c... • FALC Website: https://floridaassistedlivingconsulti... • Conference Website: https://www.floridaassistedlivingcons... • Instagram: https://www.instagram.com/floridaalfc... / alfcaregivercon • Facebook: https://www.facebook.com/share/19PK5W... • TikTok: / floridaalfconsulting • YouTube: / @carlinecadetfrancois

February 13, 2026Episode 11 hr 1 min

Stop Firefighting: How to Scale Your Startup Without Breaking It

Scaling a company is chaotic, but it shouldn't be a constant fire drill. In this episode, Gaby Enriquez (Founder of HRbp Inc.) breaks down how to build a people and compliance infrastructure that bridges the gap between profit and purpose. Whether you are navigating M&A, expanding into LATAM or APAC, or auditing for cost efficiency, this is your guide to turnkey growth and sustainable scaling.Gaby Enriquez is a global People Operations leader with 20+ years of experience helping organizations scale with integrity. As the founder of HRbp Inc., she bridges the silos between Finance, Sales, and HR to ensure every department speaks the language of business. Known as the "not-so-HR company," her team focuses on P&L, labor law, and organizational psychology to make businesses more human and humans more capable of driving profit.Connect with Gaby:Instagram: @hrbp.inc | @thegabriela.enriquezLinkedIn: Gaby Enriquez

November 16, 2025Episode 141 hr 13 min

Escaping the Tech Trap: How Melissa O’Connor Rebuilt Her Firm from the Ground Up

The conversation delves into the emotional journey of recognizing business challenges and the transformative power of investing in solutions. The speaker shares personal experiences of pain and joy associated with financial decisions that lead to business clarity and success. They encourage others to explore their business aspirations and seek help, emphasizing that solutions may be more accessible than they appear.Takeaways• The most painful part was realizing I had a problem.• Writing a big check to get out of a contract was painful.• Paying for a service that works is joyful.• Investing in solutions can lead to business clarity.• It's important to have conversations about business aspirations.• Your business dreams might not be as far off as you think.• Seeking help can make challenges seem less difficult.• Personal growth often involves financial investment.• Understanding how you want your business to run is crucial.• Don't hesitate to explore your business ideas with others.00:00 Introduction04:14 Career Beginnings06:20 Entrepreneurial Challenges14:51 Initial Software Setup25:19 Software Transition Pain32:03 Thoughts on Technology40:45 Working with Richard46:24 Vision for AI58:50 Avoiding Shiny Objects1:10:38 Elder Law Practice

October 21, 2025Episode 1348 min

Why Playing It Safe Keeps You Stuck — A Conversation with Kaila Sachse

In this episode of Connecting the Dots, host Jessica Caresse speaks with Kaila Sachse, founder of Yumari Digital, about her journey from a junior graphic designer to a successful entrepreneur. They discuss the importance of networking, the challenges of transitioning from employee to business owner, and the significance of maintaining high standards in business. Kaila shares her experiences with mentorship, the value of diversifying income streams, and the journey of recognizing one's self-worth. The conversation emphasizes the importance of encouragement and resilience in the face of challenges.• Kaila never thought she would become a business owner.• She aimed to keep as many doors open for herself as possible.• Designing her life to fit her needs was crucial.• Networking played a significant role in her success.• Under promising and over delivering is essential in business.• Self-worth is a continuous journey for entrepreneurs.• Mentorship can provide invaluable guidance and support.• Maintaining high standards is key to client satisfaction.• Flexibility in work is important for personal well-being.• Encouragement and resilience are vital in entrepreneurship.

October 15, 2025Episode 113 min

You’re Not Broken — You’re Blocked: The Energy Shift That Changes Everything

In this enlightening conversation, Jessica Caresse and Lorena Anderson explore the transformative power of energy shifting and personal growth. Lorena shares her journey from overcoming personal struggles to becoming a successful life and energy coach. The discussion delves into the importance of self-awareness, breathwork, and the role of unconditional love in fostering personal transformation. Listeners are encouraged to recognize their own energy fields, embrace their authentic selves, and take actionable steps towards empowerment and self-love.Takeaways• Lorena emphasizes the importance of sharing insights to help others find peace.• Personal transformation requires consistent effort and self-acknowledgment.• Understanding one's energy field is crucial for personal growth.• Breathwork can help access and enhance inner energy.• Self-awareness is key to recognizing and trusting one's intuition.• Unconditional love for oneself is essential for healing and growth.• Negative energy can be transformed through conscious practices.• Empowerment comes from recognizing and honoring one's own gifts.• Finding one's voice is a significant step in personal authenticity.• Practical steps and guidance can accelerate personal transformation.

October 15, 2025Episode 101 hr 2 min

From Corporate to Cosmic: How Barbara Alexander Found Her Aligned Path

In this engaging conversation, Jessica Caresse and Barbara Alexander explore the fascinating intersection of business astrology and soul-led leadership. Barbara shares her journey from corporate success to coaching, emphasizing the importance of authenticity, personal growth, and understanding one's astrological influences. The discussion delves into collective consciousness shifts, the role of relationships in personal evolution, and the significance of finding alignment in both business and personal life. Listeners are encouraged to embrace their unique paths and seek guidance in their journeys of self-discovery.Takeaways• Barbara Alexander specializes in business astrology and soul-led leadership.• Astrology can help leaders navigate personal and professional growth.• Collective consciousness is shifting towards self-empowerment and authenticity.• Understanding one's astrological chart can provide insights into personal challenges.• Relationships often evolve as individuals undergo personal growth.• Barbara's journey from corporate success to coaching illustrates the power of transformation.• Astrology can inform leadership styles and decision-making processes.• Finding alignment in business requires understanding one's unique energy.• Deconditioning is essential for discovering one's true self.• Self-discovery often involves seeking guidance from mentors or coaches.

October 15, 2025Episode 91 hr 12 min

Brain Training That Transforms Lives: Inside Dr. Maryna Yudina’s Approach

This conversation explores the intersection of personal growth, neuroscience, and the transformative power of brain training. The host and guest discuss their experiences with golf, decision-making, and overcoming personal challenges, emphasizing the importance of tailored approaches to mental health and performance. The dialogue highlights how leadership and self-discovery can create a ripple effect, impacting not only individuals but also their communities and businesses. In this conversation, Jessica White shares her personal journey of healing and transformation through neurofeedback and psychotherapy. She discusses her skepticism towards neurofeedback initially but later experiences significant improvements in her emotional stability and decision-making. Jessica emphasizes the importance of customized programs tailored to individual needs and the integration of neuroscience with coaching. She highlights the journey of self-discovery, overcoming limiting beliefs, and the emotional richness that comes from helping others. The conversation concludes with insights on learning from mistakes and the value of patience in personal growth.Takeaways• Neuroscience plays a crucial role in understanding brain function and improving performance.• Personal experiences can lead to significant transformations through brain training.• Making tough decisions is essential for personal and professional growth.• Opportunities can arise from challenges, especially during difficult times.• Building a business can create a ripple effect, impacting many lives.• Self-discovery is a journey that often involves overcoming past traumas.• Tailored approaches to brain training can lead to better outcomes for individuals.• Adapting to change is vital for success in any field.• Finding clarity and focus can significantly improve one's quality of life.• Healing starts from within before helping others.• Skepticism can lead to unexpected breakthroughs.• Trusting professionals can lead to significant change.• Customized programs are essential for effective healing.• Emotional stability is crucial for personal growth.• Present-moment awareness enhances clarity and decision-making.• Limiting beliefs can hinder self-acceptance and growth.• Emotional richness is more valuable than financial wealth.• Learning from mistakes is key to personal development.• Patience is necessary for lasting change.