14. Give it A Year
Courageous Dreamers Win
Some years don’t ask for your permission. They just come for you. This episode is Nesha’s most personal yet. After the sudden death of her younger sister and a breast cancer diagnosis just weeks later, she found herself in a year she never would’ve chosen. Grief stacked on top of shock. Radiation appointments scheduled around tears. And somewhere in the middle of it all, a literal FedEx truck. But this isn’t about tragedy. This is about truth. Nesha shares the eight lessons that carried her through the hardest season of her life, from learning that grief and joy can live...
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13. Trust the Fast Yes
Courageous Dreamers Win
Overnight success is a myth, but when alignment shows up, it moves fast. This episode is a reminder that dreams rarely unfold the way we expect them to. Nesha shares how her recent decision to buy a beach condo, a long-held dream quietly sitting on her vision board, came together in a matter of days. On the surface, it looked spontaneous. In reality, it was years in the making. She talks about the role of timing, the slow build behind what looks like fast progress, and the importance of listening to your gut even when the evidence isn’t there yet. What if the thing you've been...
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12. The Courage to Say No
Courageous Dreamers Win
Saying no is one of the most courageous things you can do when you’re done settling for a life that doesn't fit. This episode is a real and honest look at what it takes to stop overcommitting and start making choices that actually feel right. Nesha Pai opens up about her own turning point, when she realized that saying yes to everything was costing her the very life she wanted to build. What happens when your calendar looks full but your soul feels empty? How do you tell the difference between something that’s safe and something that’s aligned? Through personal...
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11. Courage Doesn’t Settle
Courageous Dreamers Win
Most people don’t realize they’ve settled until one day they look around and wonder how they ended up with a life that doesn’t quite fit. Nesha shares what surfaced during her final week in Paris - a mix of reflection, healing, and a moment of clarity that hit her during a mastermind retreat. When asked how she’s shown courage in her life, she didn’t have a tidy answer. But then her coach pointed out something she hadn’t fully seen: she doesn’t settle. And that realization cracked something open. Nesha starts unpacking what settling actually looks like, not just staying in...
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10. Courageous Solo Travel (for Women)
Courageous Dreamers Win
Solo travel can be one of the most radical ways a woman learns to trust herself, hear herself, and build a life that actually fits. In this episode, Nesha Pai shares how a solo trip to Paris turned into part-time living, and why she believes every woman should try traveling alone at least once. She talks about the years of intentional choices that made this possible, from starting her own business to setting aside $25 at a time for a travel fund. None of it happened overnight. But over time, it added up to something bigger: a life designed with purpose. What happens when you give...
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09. The Proximity Effect
Courageous Dreamers Win
Your growth will never outpace your environment. In this episode, Nesha Pai breaks down why proximity is power, and how the people you spend time with are quietly shaping your mindset, energy, and success. If you’ve ever felt stuck, uninspired, or like your dreams are “too much” for the people around you, it might be time to audit your circle. From redefining her own champion circle to building a business rooted in aligned relationships, Nesha shares personal stories and practical steps for finding the right rooms and protecting your energy. You’ll learn how to shift your...
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08. The Alchemy of Clarity
Courageous Dreamers Win
Clarity isn’t about having all the answers; it’s about finally hearing the truth that’s been waiting inside you. What if the fog you keep running into isn’t a barrier, but an invitation? In this episode, Nesha Pai sits down with Emily Paul, the founder of Aum Holistic Healing Arts, to talk about what it really means to come home to yourself. Through her work rooted in Daoism, alchemy, and intuitive guidance, Emily helps people reconnect with their purpose, not by chasing something outside themselves, but by learning to listen inward. Nesha and Emily discuss how clarity...
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07. Build Your Courage Through Fear
Courageous Dreamers Win
Confidence doesn’t come first. You earn it by doing the things that scare you. Fear has a way of showing up right before something meaningful. So how do you move forward when it feels safer to stay still? In this episode, Nesha Pai talks about the power of courage and why doing the hard, scary things is the only way to build real confidence. Through stories of joining an MMA gym, performing in a dance competition, and traveling solo, she shares how pushing past fear changed her from the inside out. You’ll learn simple ways to take action, even when your nerves tell you not...
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06. SELF-LOVE Isn’t Selfish
Courageous Dreamers Win
Self-love isn’t a luxury or a trend. It’s a daily decision to treat yourself with the same kindness you offer everyone else. In this episode, Nesha Pai breaks down what self-love truly means and why it’s central to living a fulfilling life. She reflects on her own upbringing in East Tennessee, where societal pressures made self-acceptance difficult, and shares how learning to turn inward with grace and honesty changed everything. Nesha challenges the idea that self-love is about bubble baths and affirmations. Instead, she reframes it as an ongoing practice built on how we think,...
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05. Getting LIT with Dr. Jeff Karp
Courageous Dreamers Win
Your mind is your most powerful tool. Nesha Pai welcomes Dr. Jeff Karp, a Harvard Medical School professor and author of “LIT: Life Ignition Tools,” to talk about how small, intentional shifts can spark creativity, resilience, and meaningful change. The key to a more fulfilling life isn’t about doing more, but about thinking differently. Dr. Karp explains how simple daily choices—setting an intention, embracing failure, and staying present—can open doors to unexpected growth. He reflects on his own struggles with learning and self-doubt, revealing how they shaped his...
info_outlineThere's very few times where we as entrepreneurs won't face some form of fear. Perhaps it's the fear of stepping into the unknown of small business ownership, maybe it's fear of rejection of proposals, or usually it's the far-too-familiar imposter syndrome that haunts so many. Fortunately for us, today's guest allows us to recognize fear, acknowledge it, and make fear "our homeboy."
Judi Holler is the author of Fear is My Homeboy, as well as a motivational speaker and business coach who has worked with clients from Ford to Sprint to Marriott and many more in between. Judi has coached high-level excutives and their teams to bring their best to the table, using her high-energy dynamic approach to her business, her own personality and life.
Judi Holler joins host Nesha Pai for a candid discussion about many of the common behaviors and patterns that Judi seems holiding so many back, including the aforementioned imposter syndrome. Judi also discusses her experiences being a keynote speaker presenting for hundreds of people at a time, as well as one of her most formative experiences: dropping out of Chicago's famed Second City improv group.
Connect with Judi Holler online at judiholler.com.
Purchase Judi's book, Fear is My Homeboy, here.