🎧 In this episode of The Tragedy Academy Podcast, Jay speaks with Jenn Bouler — known on Instagram as “Jenn with two Ns” — about the unseen layers of addiction, the masks we wear to fit in, and what happens when you finally take yours off. 🎙️
✨ Jenn’s story isn’t marked by trauma or chaos, making it resonate even deeper. A happy childhood. A solid career. A beautiful son. And yet, beneath the surface, alcohol crept in not to numb the pain… but to mute the pressure of perfection. In this episode, she shares what it means to hit a “high bottom,” how the wine-mom culture glamorizes escape, and what finally drove her to reclaim her identity from behind the bottle.
With candor, heart, and Jay’s signature mix of humor and insight, this conversation dives deep into the cultural constructs of “normal” drinking, the shame that lingers behind the scenes, and the power of showing up for yourself, one sober day at a time. From grocery store wine planning to white-chip meetings, Jenn’s path reminds us: the real you is always worth meeting.
🔑 Key Takeaways:
🐾 [00:03:22] “Becky” — Jenn’s drinking alter ego — gave her temporary escape, but not real freedom
🍷 [00:16:58] Planning for weekend drinking is a red flag we normalize in middle-class culture
💔 [00:28:38] Friends and family lovingly noticed before she did: “You’re drinking more every time I visit.”
👩‍👦 [00:30:03] Her son, just five at the time, became her biggest reason for change
💡 [00:35:04] “I came for my son. I stayed for me.” — How a support meeting changed her entire frame
👤 Guest Bio:
Jenn Bouler is a Tampa-based mom, sales rep, indoor cycling instructor, and founder of Jen Walks Dogs, a business built on joy and connection. Eight years sober as of 2025, she shares her journey of recovery and self-discovery with refreshing honesty. A Midwest native with a big heart and a contagious smile, Jenn lives her life with passion, presence, and a deep desire to help others feel less alone.
📣 CTA for Guest:
Want to follow Jenn’s journey? Connect with her on:
Instagram:
• @jenn_bouler
• @jenn_b_spin (Indoor Cycling)
• @jenn_walks_dogs (Dog Walking)
Whether on a bike, a sidewalk, or holding space in her community, Jenn radiates truth and transformation. Follow her for daily reminders that growth can be graceful, and joy is always worth chasing. 🐶💛🚴‍♀️
🌀 Conclusion: This episode isn’t just about sobriety but sovereignty. About taking back your life, one intentional breath at a time. Thank you, Jenn, for being a lighthouse.
🎧 Tune in next week for another honest, heart-opening episode of The Tragedy Academy Podcast.
Be cool and keep learning. 🌿🕊️
🚀 Welcome to The Tragedy Academy Podcast 🚀
Discover stories of resilience, redemption, and the human spirit. Hosted with empathy and humor, we share inspiring narratives that blend wisdom and wit, offering insights, laughter, and growth. Join our community and connect through shared experiences.
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"Detention" Warning: Expect offbeat humor, unexpected tangents, and unfiltered fun. This is not your usual Tragedy Academy episode—if you want serious topics, look elsewhere. Listener discretion advised.

In this hilarious episode of The Tragedy Academy Podcast, Jay reconnects with stand-up comedian Hernando Del Castillo—host of I Am Just Gaying—for a "Detention Episode" packed with laughs, real talk, and deep dives into identity, community, and self-love. 🎭💖

From outrageous one-liners to raw reflections, Hernando shares his journey growing up gay and Colombian, coming out twice (once as gay, once as a comedian), and how comedy became his safe space. 🇨🇴🎤 Jay and Hernando tackle everything from pronoun panic to the exhaustion of living behind masks. The episode balances gut-busting humor with heartfelt insights on family, trauma, and radical self-acceptance. 🌈🔥

🎧 Key Takeaways:

💬 [00:15] "Sniffies is the new Grindr, bro!" – Hernando’s hilarious take on hookup apps

👩‍👦 [02:44] "Coming out as a comedian was harder than being gay." 💔 🏳️‍🌈 [10:44] Jay shares his experience of being bullied for gynecomastia in the '90s 🗣️ [17:30] "Give us grace" – A candid discussion on evolving identity language 🏡 [34:27] "I’m a proud Hispanic, Colombian, queer man... and I love making people laugh."

🔥 [37:36] "People left when I became myself" – The price of authenticity ✨ 🎭 [52:07] "Comedy is a magnifying glass" – Jay on humor’s power in deconstructing society 🎙️

Hernando Del Castillo, Miami-based stand-up comedian and co-host of I Am Just Gaying, blends sharp wit and raw vulnerability to tell his story as a proud gay Colombian man. His mission: to make you laugh, think, and feel—all at once.

If you enjoyed this episode, subscribe, drop a ⭐⭐⭐⭐⭐ review, and share with someone who needs a reminder that it’s okay to be real. Jay delivers unfiltered conversations that entertain and transform. 💥

Follow Hernando: Instagram @iamjustgaying | I Am Just Gaying Podcast 🎙️

Authenticity isn’t a destination—it’s a decision. Hernando walks that path with humor, grace, and a mic in hand. Don’t miss next week’s Tragedy Academy Podcast episode where tragedy meets transformation, one laugh at a time. Be cool and keep learning. 💡🎙️🔥

🚀 Welcome to The Tragedy Academy Podcast 🚀

Discover resilience, redemption, and the human spirit through humor and wisdom.

🎧 Podcasting Made Easy: Build your site

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"Detention" Warning: Brace yourself for offbeat humor, unexpected tangents, and unfiltered fun in our 'Detention' episodes. This isn't your typical Tragedy Academy fare – it's a lighthearted listen perfect for those searching for laughter. However, if you're seeking serious topics, look elsewhere. Listener discretion is advised.
In this episode of The Tragedy Academy Podcast, Jay is joined by his long-time friend, Dan. Together, they dive deep into the absurd, exploring everything from hypothetical tattoo nightmares to the very real risk of elbowless dance battles.
From smoking Willie Nelson’s braid to figuring out who the hell tried spaghetti and ranch dressing first, this Detention episode brings you a blend of stupidity, brilliance, and good old-fashioned nonsense that you never knew you needed.
🔥 Key Topics Discussed:
✅ The Willie Nelson Braid Hypothesis – Can a braid be a blunt? Should it?
✅ The #NoElbowsChallenge – What would life be like if elbows just didn’t exist?
✅ Secret Tattoo Roulette – Trust no one when the ink gun is live.
✅ Food Combos: Stoner or Not? – Spaghetti + ranch = a crime?
✅ Things You Should Never Hear in an F1 Earpiece – "Hold this headset, I have diarrhea" is not ideal.
✅ Who Did It First? – Who milked the first cow, and were they okay?
✅ What Would You Smoke If It Got You High? – Einstein’s mustache? Sure. The Constitution? Maybe.
📌 Why This Episode Matters This episode reminds us that not everything has to be deep to be necessary. Sometimes we need a break, a laugh, and an utterly unhinged conversation about tattooing Jaden Smith on your thigh. Whether you’re burning out or tuning in, this Detention session delivers.
🚀 Listen now and ask yourself: “Would I survive life without elbows?”
🔗 Full Episode Available On: 🎧 Spotify | Apple Podcasts | YouTube
🚀 Welcome to The Tragedy Academy Podcast 🚀 Discover stories of resilience, redemption, and the human spirit. Hosted with empathy and humor, we share inspiring narratives that blend wisdom and wit, offering insights, laughter, and growth. Join our community and connect through shared experiences.
🎧 Podcasting Made Easy: Build your site with https://bit.ly/3LSCBh5
📲 Upgrade Your Recording: Riverside.FM https://bit.ly/3ImjNWD
👕 Get the Gear: Loved Jay’s t-shirt? Grab it at Into the AM: https://bit.ly/431MLD5
📘 Expand Your Mind: Check out our favorite reads! https://bit.ly/42pPHcv
✅ Subscribe: https://www.youtube.com/channel/UCEUXqlregig6vcrvuVNGlKg
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In this episode of The Tragedy Academy Podcast, Dr. Adi Jaffe joins Jay for a deep, unfiltered discussion on addiction, transformation, and the illusions of identity that hold us back.
From his personal journey of addiction and incarceration to becoming a UCLA-trained psychologist and best-selling author, Dr. Jaffe breaks down the misconceptions around addiction, the power of shifting perspective, and why breaking free from societal expectations is key to personal growth.
🔥 Key Topics Discussed:
✅ The Truth About Addiction – Why it’s not just about the substance, but about unprocessed pain and survival mechanisms.
✅ Escaping the Illusion of Identity – How early experiences shape our reality and the challenge of breaking free from conditioned beliefs.
✅ Self-Judgment & Humility – Learning to sit with the “monster” within instead of running from it.
✅ From Drug Dealer to Doctor – The journey from rock bottom to helping others redefine their lives.
✅ Why Motivation is a Lie—And Purpose is Everything – What actually drives long-term transformation.
⸻
🔹 Quotes from the Episode
🗣️ “Perspective is everything. The life you think is real is just the version you were taught to see.” – Dr. Jaffe
🗣️ “Most people aren’t addicted to substances—they’re addicted to escaping themselves.” – Jay
🗣️ “The only way to stop running from your past is to sit down and have lunch with your lion.” – Jay
⸻
🔹 About Dr. Adi Jaffe
Dr. Adi Jaffe is a former drug dealer turned UCLA-trained psychologist, TEDx speaker, and author of the books The Abstinence Myth and Unhooked. He is the founder of IGNTD, a revolutionary approach to addiction and mental health that moves beyond outdated recovery models and focuses on empowerment, not shame. Dr. Jaffe has been featured on CNN, The Today Show, Forbes, The Huffington Post, and more.
🔗 Learn More & Connect with Dr. Adi Jaffe:
• Website: IGNTD
• Books: The Abstinence Myth & Unhooked
• Instagram: @dradijaffe
⸻
📌 Why This Episode Matters
This episode challenges everything you thought you knew about addiction, personal growth, and self-worth. If you’ve ever struggled with breaking free from old patterns, self-judgment, or feeling like your past defines you—this conversation is a must-listen.
🚀 Listen now and break free from the illusion of who you think you have to be.
🔗 Full Episode Available On:
🎧 Spotify | Apple Podcasts | YouTube
🚀 Welcome to The Tragedy Academy Podcast 🚀
Discover stories of resilience, redemption, and the human spirit. Hosted with empathy and humor, we share inspiring narratives that blend wisdom and wit, offering insights, laughter, and growth. Join our community and connect through shared experiences.
🎧 Podcasting Made Easy: Build your site with https://bit.ly/3LSCBh5
📲 Upgrade Your Recording: Riverside.FM https://bit.ly/3ImjNWD
👕 Get the Gear: Loved Jay’s t-shirt? Grab it at Into the AM: https://bit.ly/431MLD5
📘 Expand Your Mind: Check out our favorite reads! https://bit.ly/42pPHcv
✅ Subscribe:https://www.youtube.com/channel/UCEUXqlregig6vcrvuVNGlKg
📱 Follow Us:
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💖 Support Us: Please help us continue bringing meaningful content by donating via PayPal or Buy Me a Coffee!

Trigger Warning: This episode of The Tragedy Academy Podcast addresses serious and potentially distressing topics, including sexual abuse and trauma. The content may be triggering to those who have experienced similar events or are sensitive to discussions of abuse and trauma. We urge listener discretion and recommend that individuals affected by these topics consider their comfort and well-being before listening.
Throughout the conversation, we explore deeply emotional stories of overcoming childhood sexual abuse and breaking the chains of generational trauma. These narratives, while ultimately grounded in hope and resilience, involve graphic discussions of abuse and its long-lasting effects.
Please prioritize your mental health and seek support if needed. Resources and help are available; you don’t have to face this alone.***
In this raw and enlightening episode of The Tragedy Academy Podcast, Jay is accompanied by a remarkable guest, Cindy Benezra, a survivor and advocate who faced the darkest shades of human experience. Together, they unravel the deeply emotional narrative of overcoming childhood sexual abuse and the journey towards breaking the chains of generational trauma. 🎙️
Walking through the shadows of her past, Cindy Benezra bares her soul, shedding light on the stark reality of living with a pedophile and enduring the agony of childhood abuse. Join Jay with his unique blend of introspection and empathy as he uncovers the pivotal moments that steered Cindy towards a life of empowerment. This conversation is more than just a tale of survival; it's an inspiring testament to human resilience and the transformative power of self-love. Don't miss this episode, where the heights of hope and healing counter the depths of despair. 🌟✊
Key Takeaways:
🔑 [00:10:09] The scars of childhood trauma are deep, but acknowledging them is the first step towards change and healing.
🔑 [00:32:02] Embracing your darkest thoughts can be daunting, but doing so is crucial to personal growth and finding your path to recovery.
🔑 [00:43:25] Authenticity is powerful—being true to who you are can be your anchor in the tumultuous sea of life's challenges.
🔑 [00:56:20] Despite living in close quarters with our inner 'lions', we hold the strength not to let past traumas define our present or future.
🔑 [End] Love yourself unconditionally, for it is the bedrock upon which we can build a foundation to encourage the same in others.
Guest Bio: Cindy Benezra is a resilient individual who has not only survived the terrors of sexual abuse but has emerged as a staunch advocate for those who have faced similar predicaments. Her experiences, though deeply saddening, are laced with her unwavering spirit to overcome and help others do the same. The insights she imparts are rooted in her battle and triumph over the debilitating effects of her trauma.
If Cindy's story has moved you or Jay's in-depth conversations resonate with your quest for understanding the human experience, subscribe to The Tragedy Academy Podcast. Please leave us a heartfelt review and share this episode with anyone who might find strength in Cindy's journey. 🎧 Be cool and keep learning. 💡
To discover more about Cindy Benezra and her advocacy work, we urge you to dive deeper into her narrative. Visit her website, follow her endeavors on social media, and immerse yourself in her ongoing projects that illuminate the path for countless others. Let's amplify her voice and extend the ripples of her influence. 💪🌐

In this throwback episode of The Tragedy Academy Podcast, Jay reconnects with Edison Jakupi, a man whose journey embodies resilience, reinvention, and the power of never giving up. From fleeing war-torn Kosovo to building a thriving career in the U.S., Edison’s story is a testament to what it means to start over—and win. 🎙️
🎧 Now remastered with upgraded audio & video, this episode brings back one of our most powerful conversations.
What You’ll Hear:
🔥 [07:45] “I watched my family lose everything overnight—and that’s when I learned what really matters.”💡 [14:20] The unexpected lesson Edison learned from rebuilding his life in a new country.🎵 [21:05] How Kosovo-Albanian culture shaped his music & creative journey.💰 [30:40] The mindset shift that took Edison from survival mode to success mode.🌎 [45:10] Why hardship doesn’t define you—how you respond to it does.
🎙️ Thinking of launching a podcast? Let us handle the editing, production, and branding so you can focus on telling your story. Check out TragedyAcademyStudios.com to get started today.
Guest Bio:
Edison Jakupi is an entrepreneur, artist, and storyteller who brings his rich cultural heritage into everything he does. Growing up as a refugee, he experienced firsthand the struggles of displacement, adaptation, and perseverance. Today, he’s a successful business owner, blending creativity with strategy to build something meaningful. His story is a powerful reminder that no matter where you come from, you have the power to shape where you’re going.
CTA for Show:
🚀 Join the journey. Subscribe to The Tragedy Academy Podcast for real stories of resilience, raw truth, and the lessons that come from life’s toughest moments.👉 Watch & Listen Now: TragedyAcademyStudios.com💬 Leave a review & share! Help us amplify these stories.
CTA for Guest:
🎤 Follow Edison Jakupi to see how he continues turning adversity into opportunity.📲 Find him on Instagram: @EdisonJakupi
Tragedy Academy Studios – Custom Media & Production Services
Looking to launch your own podcast, create a unique sound, or get high-quality production work? Tragedy Academy Studios offers professional services to elevate your creative vision.
✅ Podcast Production & Editing – Full-service solutions for creators.✅ Voiceover & Audio Work – Professional recording, mixing, and mastering.✅ Video Production – Cinematic, engaging, high-quality visuals.✅ Custom Music Tracks & Promos – Original intros, background music, and branding for your podcast or business.
📲 Book a session or learn more at TragedyAcademyStudios.com
Conclusion:
Life knocks you down. Edison’s story proves you can always stand back up.💙 Be cool and keep learning.
🎧 Podcasting Made Easy: Build your site📲 Upgrade Your Recording: Riverside.FM👕 Grab the Gear: Into the AM📘 Expand Your Mind: Our Favorite Reads✅ Subscribe: YouTube Channel
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Facebook: TragedyAcademyStudios
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💖 Support Us: Donate via PayPal or Buy Me a Coffee
Twitter: @TragedyAcademy
TikTok: @TragedyAcademyStudios
💖 Support Us: Donate via PayPal or Buy Me a Coffee

Susan Gold—a woman whose journey from a tumultuous childhood to becoming a transformational coach is nothing short of inspiring. This video edition brings a fresh perspective to an episode that resonates deeply with the show’s core themes: breaking generational cycles, reclaiming authenticity, and embracing self-transformation.

Susan shares her raw and powerful story of growing up in a dysfunctional home, navigating the entertainment industry, confronting personal trauma, and ultimately stepping into her truth. From escaping a toxic marriage to finding her voice as a coach and author, Susan’s path is a testament to resilience and self-discovery.

This episode serves as a reminder that no matter where we come from, we have the power to rewrite our story. Whether you’re healing from the past, seeking clarity, or just looking for an insightful, heartfelt conversation, this is an episode you won’t want to miss. 🌟

🌟 Key Takeaways:

💬 [00:06:44] "Abused and hurt children raising abused and hurt children" – Breaking generational trauma.

📖 [00:13:09] How Susan closed a major talent deal by understanding human nature.

🎭 [00:16:29] Leaving a toxic marriage—choosing self-worth over survival.

🌍 [00:25:49] The victim mentality & why breaking free is harder than we think.

🎙️ [00:40:24] How writing her book became an unexpected healing journey.

👤 Guest Bio:

Susan Gold is a transformational coach, speaker, and author of Toxic Family: Transforming Childhood Trauma into Adult Freedom. With a background in the entertainment industry and years of personal experience overcoming trauma, Susan now helps others break free from limiting beliefs, step into their power, and create a life of authenticity and joy.

🔗 Learn more at SusanGold.us

📣 Watch & Listen:

🎥 Video Edition Available on our website and major platforms🎧 Listen on: Apple Podcasts, Spotify, Google Podcasts, and more. 📢 Subscribe & Leave a Review! Help us grow the tree of knowledge 🌳TheTragedyAcademy.com

💡 Connect with Susan Gold:

📌 Website: SusanGold.us 📖 Book: Toxic Family: Transforming Childhood Trauma into Adult Freedom 📲

Thank you for tuning in to this special episode! Share, subscribe, and let’s keep growing together. 🚀 Be cool and keep learning.