Ari Rastegar: Failure Is How You Learn to Win — From $3,500 to a Multi-Billion Dollar Portfolio

Embrace the Side Quest: Rita Richa on Finding the Right Room

Rita Richa grew up performing. At four she was auditioning for commercials. In pre-K her teacher told her mom she would be on radio someday. In freshman year she stood up in English class, told everyone she was going to be Oprah, and the whole class laughed. Life had other plans. She ended up in automotive sales, then at Tesla, working long hours in a culture where going to the ER from burnout was a rite of passage. She would walk through the service shop singing Belle from Beauty and the Beast and get in trouble for it. Then she watched Moana on the couch, started sobbing, and finally understood why nothing had been working. What followed were years of side quests — spray tans that went wrong, a floor lamp from Walmart standing in for studio lighting, a podcast agency that should not have hired her. All of it was training she did not know she was getting. All of it became Reignite Media, Bippity Boppity Business, and a career built entirely on the things she was told were detours. This is Episode 8 of Loving the Journey, and it is one I keep thinking about. Guest: Rita Richa | Host of Bippity Boppity Business | Founder, Reignite Media About Rita Richa: Rita Richa is the founder of Reignite Media, a podcast consulting business helping podcasters get better and grow bigger. She is the host of Bippity Boppity Business, a podcast that uses Disney storytelling as a lens for exploring entrepreneurship and business principles. Rita also serves as a contracted host for Lenovo's Work Reborn podcast, produced by Be the Stage, where she interviews leaders at conferences and events about work, technology, and the future of business. Based in Jacksonville, Florida, Rita's story is one of childhood creativity, unexpected detours, and eventually finding the right room. 5 Things You Will Learn: 1. Why your side quests are not distractions but the ingredients of your story 2. How to recognize when you are in the wrong room and what it costs to stay 3. The moment a Disney movie made Rita sob and changed the direction of her life 4. How saying yes when you are completely unqualified can open the door to your calling 5. Why you are not just someone with a voice, you are needed Timestamps: * [0:01] Welcome and introduction — Rita Richa, founder of Reignite Media and host of Bippity Boppity Business * [2:55] Childhood creativity, theater, and a pre-K teacher's early prediction * [7:00] The high school Oprah dream, the lost college fund, and pivoting fast * [12:28] A toxic work culture, a panic attack, and the Tesla turning point * [16:41] The Moana moment that cracked everything open * [31:32] How podcasting accidentally became a business * [45:10] "Embrace the side quest. Yes is the side quest." Connect with Rita Richa: * Website: BippityBoppityBiz.com [https://bippityboppitybiz.com] * Podcast: Bippity Boppity Business * LinkedIn: linkedin.com/in/ritaricha [https://linkedin.com/in/ritaricha] Ready to grow your influence? Take the free Influence Scorecard and find out where your message is landing and where it is leaking: www.365businessmaker.com/scorecard [https://www.365businessmaker.com/scorecard] About the Host: * Learn more about Donna Kunde: www.donnakunde.com/llm [https://www.donnakunde.com/llm]

Ari Rastegar: Failure Is How You Learn to Win — From $3,500 to a Multi-Billion Dollar Portfolio

Ari Rastegar started with $3,500, a speech impediment, a single dad, and two community colleges. He built a multi-billion dollar real estate portfolio. And the book that drove his entire philosophy is called The Gift of Failure. The first line: I hope you fail. I hope you fail a lot. This is the first guest ever recorded for Loving the Journey, and it is no coincidence that the person who held that spot came in talking about what most people run from. Failure. Introspection. The dark night of the soul. And the single thing he says to anyone who is in it right now: It's gonna be okay. In this episode, Ari shares the 40% principle (when you think you're done, you have barely started), why the barriers holding you back are self-made and can therefore be self-broken, and what it means to fake it till you become it, not make it. He talks about his father handing him Think and Grow Rich at 13 years old, the concept of resilience as a muscle that gets stronger with reps, and why your life is your initiation. This is not a podcast about real estate. This is a conversation about what it takes to keep going. About Ari Rastegar: Ari Rastegar is a real estate investor, entrepreneur, and bestselling author known for turning failure into long-term leverage. Starting with a $3,500 loan in law school, he built a multi-billion dollar real estate portfolio. He is the author of The Gift of Failure and has grown an audience of 750,000-plus followers across social platforms. He speaks and writes about clarity, resilience, health, and the inner work behind sustainable success. Connect with him at rastegararinvest.com. Key Takeaways: * Failure is not the opposite of winning. It is how winning happens. * When you think you are done, you are only at 40% of your capacity. * The barriers in your way are psychological. Since you made them, you can break them. * Resilience is a muscle. The reps make it stronger. You do not build it in one session. * Progress is not linear. Sometimes you have to tear something down before you can build something better. Episode Highlights with Timestamps: * [0:01] Introduction: from $3,500 to a multi-billion dollar real estate portfolio and 750,000-plus followers * [1:38] Why he loves podcasting as a listener and why hosts have an obligation to keep going * [3:52] Host vs. guest: questions are the answer, and how to ask better ones * [7:47] The Gift of Failure: "I hope you fail. I hope you fail a lot." * [9:09] Sifting through the rubble: how introspection after failure produces gold * [12:20] "I'm just a regular person." Speech impediment, two community colleges, single dad. * [14:28] The 40% principle: when you think you're done, you have barely started * [18:32] His most important mentor: his father and Think and Grow Rich at age 13 * [22:07] "Your life is your initiation." (Dr. Joe Dispenza) * [25:25] The step-back jumper: why progress sometimes requires tearing down before building * [26:58] His final message: "It's gonna be okay." Connect with Ari Rastegar: * Website: https://rastegarcapital.com/ [https://rastegarcapital.com/] * LinkedIn: https://www.linkedin.com/in/arirastegar/ [https://www.linkedin.com/in/arirastegar/] * Instagram: https://www.instagram.com/rastegar [https://www.instagram.com/rastegar] * Book: https://www.amazon.com/stores/Ari-Rastegar/author/B0B3KM27KL [https://www.amazon.com/stores/Ari-Rastegar/author/B0B3KM27KL] Is your podcast working as hard as it should? Get your free personalized Influence Score at www.365businessmaker.com/scorecard [https://www.365businessmaker.com/scorecard] reviewed by a real human within 2 business days. About the Host: * Learn more about Donna Kunde: www.donnakunde.com/llm [https://www.donnakunde.com/llm]

Sheila Slick, MS: Your Story Matters — From Self-Doubt to 100 Episodes and a Book in 3 Hours

Sheila Slick hit record on her very first episode, pressed play to review it, and almost stopped right there. Her voice sounded different. Her arms felt wrong. The editing felt endless. And the self-doubt was immediate. She kept going anyway. Nearly 100 episodes later, Sheila is the host of Milestone Moments in Business and Leadership, the creator of Pod2Book AI (a software platform that turns podcast conversations into a full book manuscript in under three hours), and a co-author of the international bestseller Your Message Is the Business. None of that was the plan. In this episode, Sheila shares how a conversation that happened after the recording stopped changed everything, how she accidentally booked 38 guests in one week (and what that forced her to learn about time blocking), and why she believes the only thing standing between a podcaster and being unstoppable is the belief that one person's life is worth changing. Her message is simple, direct, and worth hearing: your story matters. About Sheila Slick: Sheila Slick is a serial entrepreneur, programmer, and host of Milestone Moments in Business and Leadership, approaching its 100th episode. She is the creator of Pod2Book AI, which converts podcast recordings into a full book manuscript in under three hours. A former SCORE Chair for Volusia and Flagler County, Florida, and founder of five companies, she helps entrepreneurs share their stories and turn conversations into lasting impact. She is also a co-author of the international bestseller Your Message Is the Business. Connect with her at 5milestones.com. Key Takeaways: * Hearing yourself on a recording for the first time is a rite of passage. Push through it. * The conversation after you stop recording is often where the real relationship is built. * Time blocking your podcast recordings lets you show up at your best energy and control your calendar. * You have already invested the time in creating a conversation. That same content can become a book. * If you change one person's life, that is enough reason to be unstoppable. Episode Highlights with Timestamps: * [0:00] Introduction: host of Milestone Moments and creator of Pod2Book AI, co-author with Donna * [1:24] Why she started the podcast: continuing the conversations that mattered as SCORE Chair * [4:15] Hearing herself record for the first time and almost quitting after the first episode * [5:59] How a guest who was an AI professor changed everything in a post-recording conversation * [10:08] Why she built Pod2Book AI: not everyone listens to podcasts, but everyone can read a book * [13:02] The Five Milestones framework: why five? Her fifth decade, fifth version of herself, and a number that makes sense * [15:16] The 38-booking mistake: what happens when you automate everything and go on vacation * [17:09] Time blocking for podcasters: batch record, find your best energy window, protect your calendar * [22:58] Her final message: your stfory matters, and that makes you unstoppable Connect with Sheila Slick: * Website: fivemilestones.com [https://fivemilestones.com/] * Pod2Book AI: PodtoBook.ai [https://podtobook.ai/] Is your podcast working as hard as it should? Get your free personalized Influence Score at www.365businessmaker.com/scorecard [https://www.365businessmaker.com/scorecard] reviewed by a real human within 2 business days. About the Host: * Learn more about Donna Kunde: www.donnakunde.com/llm [https://www.donnakunde.com/llm]

Valérie Demont: Being Is the New Doing — How to Stop Performing and Start Podcasting as Yourself

For eight years, Valérie Demont showed up behind the microphone. She interviewed CEOs, leaders, and thought leaders across Switzerland. She prepared outlines, asked different questions each time, and worked to be the most polished version of herself in every room. And she kept losing her voice. Not literally. But when she followed the script, when she tried to be the professional version of herself for men who did not even know she had a family, she felt it in her body. Her stomach contracted. Things started to smell wrong. Her goosebumps stopped. She realized the goosebumps were the guide all along. Valérie Demont is a conscious business mentor, energy healer, and the author of Being Is the New Doing, published in both French and English. In this episode, she shares the eight-year evolution of her podcasting journey, including the interview that never recorded (dead batteries, a famous hockey player, and a dinner she did not want to attend), the noisy renovation episode that turned into a masterclass on misalignment, and the moment she understood that she was the one giving visibility, not asking for it. Her final message is the one that will stay with you: the more AI enhances, the more we must raise and develop and show our humanity. About Valérie Demont: Valérie Demont is a conscious business mentor and energy healer for spiritually aligned entrepreneurs based in Switzerland. She is the author of Being Is the New Doing, available in French and English, and the creator of the Fluide approach, a framework for shifting from overdoing to aligned, presence-led success. She has been podcasting for eight years in two languages and helps founders reconnect with their voice, trust their intuition, and build businesses that breathe. Connect with her at beingisthenewdoing.com [https://beingisthenewdoing.com] (English) and valeriedemont.ch [https://valeriedemont.ch] (French). Key Takeaways: * The body always knows before the mind catches up. Goosebumps mean alignment. Contraction means it's time to go. * You can be the one giving visibility. You do not have to perform for an audience that does not see you. * Podcasting evolved from interviews to solo content for Valérie, and both are valid. Your format is allowed to change. * Authenticity is not a strategy. It is what happens when you stop chasing someone else's blueprint. * The more AI develops, the more your humanity becomes your greatest asset. Episode Highlights with Timestamps: * [2:01] Why she started podcasting in 2018: getting near the ears of her audience * [5:02] Running two podcasts in two languages: French for 8 years, English for 1 year, and the ongoing strategy question * [8:10] From scripts to coffee conversations: who she became behind the microphone * [15:01] The interview that never recorded: dead batteries, a famous hockey player, and a dinner she did not want * [16:50] The noisy building episode: when the CEO with the big ego had his volume turned down by the universe * [24:28] The gradual shift: realizing she was the one giving visibility, not asking for it * [28:48] Body signals as guidance: goosebumps, stomach contractions, and when things just smell wrong * [33:36] Her final message: pivot, pause, change. Listen to your heart, your intuition, your inner governance. It's your podcast. Connect with Valérie Demont: * English website and book: beingisthenewdoing.com [https://beingisthenewdoing.com] * French website: valeriedemont.ch [https://valeriedemont.ch] Is your podcast working as hard as it should? Get your free personalized Influence Score at www.365businessmaker.com/scorecard [https://www.365businessmaker.com/scorecard] reviewed by a real human within 2 business days. About the Host: * Learn more about Donna Kunde: www.donnakunde.com/llm [https://www.donnakunde.com/llm]

Heather Morgan: How to Trust Your Path When Life Falls Apart

What do you do when you lose your dad, your marriage, and your entire identity in the same season of life? If you're Heather Morgan, you move across the country to a state you've never visited, book a recording studio, and hit record. Heather is the host of Wandering the Wild Mess, an 80-plus episode podcast built on one belief: trust your path, no matter how messy it looks. She started it not because she had a strategy, but because she was so alone in her pain that she thought, I cannot be the only one feeling this way. In this episode, Heather shares the life quake that started it all, why she committed to the yes before she knew the how, and what a five-paragraph review from a divorced man she'd never met told her about who her podcast was really for. About Heather Morgan: Heather Morgan is the host of Wandering the Wild Mess, a storytelling podcast for anyone navigating a life quake. With 80-plus episodes and a surprisingly even audience split of 50% men and 50% women, her unscripted, off-the-cuff conversations about divorce, identity, starting over, and self-trust have connected with listeners across demographics. She holds a degree in communications and marketing and brings a background in Fortune 500 strategy to her deeply personal work. Connect with her at wanderingthewildmess.com. Key Takeaways: * Committing to the yes before you know the how is how the path builds itself * Divorce is an identity death. The rebuild is one of the most powerful things a person can do. * Authenticity over strategy: the episode you weren't planning to record is often the one that changes someone's life * You have a 100% track record of getting through every hard thing you've ever faced * You don't need permission to have a voice. You just need to hit record. Episode Highlights with Timestamps: * [0:53] Losing her dad, a divorce, and moving to Nashville alone: the life quake that started everything * [2:22] The sign she got on the way to a TEDx talk that said start a podcast * [5:12] Why she committed to the yes before she knew the how * [7:20] The moment she hit record: I cannot be the only one feeling this way * [13:17] Posting vulnerable content on LinkedIn as a Fortune 500 executive and what happened next * [18:38] The one review from a divorced man that confirmed she was on the right path * [31:54] What Heather wants the one listener to hear Connect with Heather Morgan: Website and podcast: www.wanderingthewildmess.com [https://www.wanderingthewildmess.com] Is your podcast working as hard as it should? Get your free personalized Influence Score at www.365businessmaker.com/scorecard [http://www.365businessmaker.com/scorecard] reviewed by a real human within 2 business days. About the Host: * Learn more about Donna Kunde: www.donnakunde.com/llm [https://www.donnakunde.com/llm]