🎧 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.

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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
📱 Follow Us: Instagram: https://instagram.com/tragedyacademystudios Facebook: https://facebook.com/tragedyacademystudios Twitter: https://twitter.com/Tragedyacademystudios TikTok: https://tiktok.com/@tragedyacademystudios
💖 Support Us: Help us continue bringing meaningful (and ridiculous) content by donating via: PayPal: https://www.paypal.com/donate?hosted_button_id=YMU9L4TBWX6AG
Buy Me a Coffee: https://www.buymeacoffee.com/tragedyacademy