The 20 Something Playbook

M.A.E. Chats: what Bieberchella was really about

Tue, 14 Apr 2026 05:00:00 GMT

Maddie's 27th bday episode x Bieberchella revelations... buckle in. This one goes off the deep end and back :)

Website: https://www.20somethingplaybook.com/

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We’re All Living Double Lives in Our 20s (Hannah Montana Was Right)

Tue, 31 Mar 2026 05:00:00 GMT

By day, we’re working 9–5 jobs.

By night, we’re building the lives we actually dream about.

In this episode, we talk about the double lives everyone in their 20s is secretly living: balancing careers, creative dreams, social lives, and the pressure to “figure it all out.”

We get into:

- why your 20s feel so chaotic (and why that’s normal)

- the reality of working a 9–5 while chasing something bigger

- what “grit” actually means (and why it matters more than talent)

- how to keep going when you feel like you’re failing at both lives

If you’ve ever felt like you’re living two completely different identities… this episode is for you.

We hope you’re getting the best of both worlds ✨

For more visit @20SomethingPlaybook on TT/IG

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Where’s the Cute Boy With a Shoulder to Cry On?

Tue, 24 Mar 2026 05:00:00 GMT

From the new Spider-Man era of a sad, broke, and very real Peter Parker to the unrealistic expectations we get from rom-coms, we dive into how media shapes the way we think love, friendship, and our 20s are supposed to look.

For more visit @20somethingplaybook on IG/TT

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The urge to be a mf city girl but also go to the ocean and dissociate (Australia recap)

Tue, 17 Mar 2026 05:00:00 GMT

WTF are your 20s for, anyway? From the job market to frolicking in your 20s, we weigh in on what your 20s are really for.

Find the rest of this episode everywhere you get your podcasts ;)

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Why the 90s has our generation in a chokehold

Tue, 10 Mar 2026 05:00:00 GMT

In this episode, we dive into why the new series Love Story has our generation in a chokehold — from the iconic 90s fashion to the timeless casting choices and the nostalgic feeling of a pre-social media world.

We also talk about how the 90s relates to the show we're creating, our sparkle being back, and Elle's a spice girl?

Follow on IG and TT @20somethingplaybook

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M.A.E. Chats: Your 9–5 Pays the Bills. Your 5–9 Builds the Dream.

Tue, 03 Mar 2026 06:00:00 GMT

We're back from Australia! We talk about pursuing your dreams alongside 9-5 jobs, burnout, staying motivated and how Maddie is jealous of Ava and Elle's self compassion scores...

We filmed this before we left, see you next week for some post-Australia content :)

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M.A.E. Chats: Do You Still Feel Like A Diva?

Tue, 03 Feb 2026 06:00:00 GMT

Do you feel like a diva? In this episode we talk all things winter uglies, getting your sparkle back and diva dance parties… Not to mention what we think our diva songs are and last but not least, why you should invite us to your wedding!

Website: https://www.20somethingplaybook.com/

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M.A.E. Chats: What Were You Doing in 2016?

Tue, 27 Jan 2026 06:00:00 GMT

Maddie, Ava and Elle talk all things 2016. From cringey teenage years to childhood nostalgia, and last but not least Ava’s flying squirrel sweater.

YouTube: https://www.youtube.com/@20SomethingPlaybook

Website: https://www.20somethingplaybook.com/

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M.A.E. Chats: The Curse of The Eldest Daughter

Tue, 20 Jan 2026 06:00:00 GMT

Maddie, Ava & Elle talk all things curse of the eldest daughter and then proceed to rage-bait each other for 23 minutes...

Follow on TikTok/Instagram @20somethingplaybook

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M.A.E. Chats: Volume One of The 20 Something Playbook Wrapped (Part 2)

Tue, 13 Jan 2026 06:00:00 GMT

Looking back on Chapters 8-17. We talk all things filming the pod, gallivanting around the cities our guests lived in, and Olehenriksen lip balm…

Website:https://www.20somethingplaybook.com/

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M.A.E. Chats: Pretending 2025 didn’t take us out.

Tue, 06 Jan 2026 06:00:00 GMT

We talk about our 2025 character development, our thoughts on 2026, more about our screenwriting journey and go on a Stranger Things rant…

6 mins to 11 mins - Duffer Brothers/Stranger Things Finale

11:30 - Rang in new year crying into crisp

13:00 - Joe Keery

16:40 - 17:00 - Ava's stupid joke adopted

17:30 - Lunar new year smile

18:30-19:00 - 25 birthday bash

19:00-19:45 - Feeling aligned in the new year

20:00-20:25 - Ava only got 5 days off

20:45-21:18 - Maddie funny accent

21:20-22:00 - Maddie “did u rot?”

22:20-22:35 - Ava is white noise

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Volume One of The 20 Something Playbook Wrapped! Part 1

Tue, 16 Dec 2025 06:00:00 GMT

Can't believe we are here! Volume One of The 20 Something Playbook has come to an end. From lessons learned to moments we didn’t see coming, this episode breaks down Chapters One to Seven of The 20-Something Playbook, highlighting our biggest takeaways from each guest and the adventures we shared along the way.

Website:https://www.20somethingplaybook.com/

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Chapter Seventeen: Success, Anxiety, and Finding Peace in Your Twenties as a Venture Capitalist

Tue, 09 Dec 2025 06:03:00 GMT

Join us for a candid conversation with @divyadhulipala, a Forbes 30 Under 30 Venture Capitalist, and a dear friend - as she dives into the realities of working in VC in your twenties.

In this episode, Divya shares her unexpected journey into venture capital, the experience of working on Wall Street, and the crucial advice from her dad that helped shape her career. She offers invaluable insights on:

• Career & Success: What venture capital is, the difference between power/perfection and true success, and the day-to-day life of a VC.

• Her 20s Playbook: Handling pressure and anxiety, the “theory on friendships” (with a very good quote!), navigating friendship breakups, and finding peace through “resource allocation.”

• Personal Growth: The importance of surrounding yourself with people who positively influence you, why it’s about how you fail, and the hilarious story about being convinced she had diabetes.

• Networking: Practical mentor advice on how to effectively network on LinkedIn.

Don’t miss Divya’s perspective on earning the right to be in the room and her wisdom on self-preservation in a competitive world. You don’t want to miss this one.

Read more about Divya here: https://www.forbes.com/profile/divya-dhulipala/

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M.A.E. Chat: Burnout and Overwhelm in Your 20s...

Tue, 02 Dec 2025 06:00:00 GMT

We talk all things burnout whilst our camera decides not to work and one of our microphones also jumps ship :)

Seriously though, burnout in your 20s is no joke.

IG/TT:

@20somethingplaybook

Website:

https://www.20somethingplaybook.com/

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Chapter Sixteen: The Reality of Owning a Flower Truck For a Living with Vienna Hintze

Tue, 25 Nov 2025 06:00:00 GMT

This week on The 20 Something Playbook, we’re joined by Vienna Hintze - creator and owner and @mainstreetflowertruck. Vienna’s green truck, named after Fiona from Shrek, has been featured in pop-ups with incredible brands like Rare Beauty, Sweetgreens , Lululemon, celebs like Gwen Stefani and sooooo many more! 💐

Vienna shares how she went from running her own advertising agency to moving to LA and starting her flower truck business.

This episode was filmed with Fiona :)

Follow Main Street Flower Truck:

Instagram:

https://www.instagram.com/mainstreetflowertruck/?hl=en

TikTok:

https://www.tiktok.com/@mainstreetflowertruck

Website:

https://www.mainstreetflowertruck.com/

#20somethingplaybook #podcast #flowertruck #entrepreneurship

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MAE Chat: DWTS Hits DIFFERENT This Year 20s Edition

Tue, 18 Nov 2025 06:00:00 GMT

In this episode, we're diving into what makes the 2025 edition of DWTS resonate with 20-somethings. From making us nostalgic about our dancing days to relatable 20s moments from the pros, our love for Dancing With The Stars runs DEEP.

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Chapter Fifteen: Surviving A Near Death Injury & Transforming Your Life with Jason Li

Tue, 11 Nov 2025 06:00:00 GMT

This week on The 20-Something Playbook, we’re joined by Jason Li — who went from being critically injured in his early 20s to building a thriving business in his 30s.

He shares how the pain and adversity he faced after his severe injury shaped his perspective, fueled his growth, and ultimately helped him discover his passion and purpose.

Follow Jason Li: https://www.instagram.com/jason_sportstherapist/?igsh=MW9oa2VtemhoZnVkdg%3D%3D

Jason Li's The Spot Rehab: https://www.thespotrehab.com/jasonli

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M.A.E. Chats: God forbid a girl has hobbies in your 20s

Tue, 04 Nov 2025 06:00:00 GMT

Having hobbies at this time of life is a refuge from the chaos. Ava might take up knitting, Elle LOVES anything to do with sports, and Maddie... even she doesn't know her next move. But right now she's into spreadsheets... How are your hobbies going? Let us know in the comments below!

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Chapter Fourteen: Emma Kula Quit Her Corporate Job To Start A Business. Here's What Happened

Tue, 28 Oct 2025 05:00:00 GMT

Here's what happened on Emma's journey of self-discovery and entrepreneurship. In this chapter, we explore the critical decision that Emma made to leave the stability of her corporate job and take a leap of faith into the world of business ownership in her 20s.

What motivated her to make such a bold move? What challenges did she face along the way? Join us as we dive deep into Emma's story and uncover the realities of starting a business from scratch. This chapter is packed with insights, experiences, and inspiration for anyone considering a similar path. Don't miss out on her incredible journey!

M.A.E. Chats: What We've Learned From Constant Rejection in Our 20s

Tue, 21 Oct 2025 05:00:00 GMT

Join us as we reflect on the life lessons we've learned from constant rejection in our 20s so far, and how it's shaped us. Through rejection, we've been able to build our confidence and develop a growth mindset, learning to fail forward and find purpose in our young adult life.

In this video, we share our rejection advice and motivation tips on how to cope with career setbacks, and how to cultivate resilience to achieve success. Our growth journey hasn't been easy, but it's taught us valuable lessons on mental health, self discovery, and the importance of a good mindset.

Whether you're looking for tips on mental wellness or just looking to feel less alone in your 20s, this video is for you. Tune in to learn how to turn rejection into an opportunity for growth and self improvement, and how to develop the mindset you need to achieve your goals and find your purpose.

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M.A.E. Chats: Are Friends Characters Actually Relatable in 2025

Tue, 14 Oct 2025 05:00:00 GMT

What makes FRIENDS so relatable to young adults, especially among those in their 20s? We're rewatching the iconic sitcom, and share how we see ourselves now more than ever in the characters, situations and even the theme song... your life's a joke? You're broke? Your love life's DOA... It's like you're always stuck in second gear, when it hasn't been your day, your week, your month or even your year. Subscribe for a new episode every Tuesday, where we talk about the good, the bad and the ugly of our 20s.

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M.A.E. Chats: What's TAYLOR SWIFT Saying About Our 20s Through Her New Album?

Tue, 07 Oct 2025 05:00:00 GMT

Join us as we dive into the world of pop music and explore what Taylor Swift is saying about our 20s through her new album. As a renowned songwriter, Taylor Swift has a unique ability to tap into the emotions and experiences of her listeners, particularly millennials and Gen Z fans who have grown up with her music. In this video, we'll be doing a lyrical analysis of her new album, breaking down the songs and exploring the themes and messages that resonate with young adults. From the highs and lows of relationships to the struggles of finding one's identity, Taylor Swift's music has a way of capturing the essence of millennial music and pop culture. Whether you're a die-hard Taylor Swift fan or just a lover of music commentary and discussion, this video is for you. We'll be exploring the emotional connection that Taylor Swift's songs create with her listeners, and how her music reflects the ups and downs of life in our 20s.

If you liked this video, don't forget to subscribe! New episode every Tuesday :)

More M.A.E. Chats: https://www.youtube.com/watch?v=0NMUmKkcy0E&list=PL1Rs9oUYUlEc6OKwezm67aF1x85L9RBSF

Guest Episodes: https://www.youtube.com/watch?v=dSwr2pPClCM&list=PL1Rs9oUYUlEcNigeakfAcHDyKl2mSlAJ6&index=12

BTS Vlogs: https://www.youtube.com/watch?v=KNaj9QhEOls&list=PL1Rs9oUYUlEf6yeVawHLs6G3UUaj4EACf

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Chapter Thirteen: How Thamina Stoll Went From Broke to Financially Free in Her 20s

Tue, 30 Sep 2025 05:00:00 GMT

Ready for some real financial education? Join us for an unfiltered conversation as Thamina Stoll shares her journey from broke to financially free in her 20s. Through powerful storytelling and honest life lessons, Thamina reveals how financial independence is possible, even if you’re starting from zero.

If you’re tired of feeling lost with money and want actionable personal finance advice, this episode is for you! We dive deep into budgeting, money management, and investing for beginners, all from the perspective of women who’ve been there. Subscribe and join our community of financially empowered 20-somethings, committed to financial growth and supporting each other’s journeys.

Thamina’s story is proof that perseverance and determination can lead to financial freedom. Discover how she learned to save money, build wealth, and take control of her financial future. By tuning in, you’ll gain practical tips for achieving financial independence, learn the importance of financial education, and get inspired to set—and crush—your own financial goals.

Key Takeaways:

Real strategies for financial education in your 20s

How to move from broke to financially independent

Budgeting tips that actually work

Investing for beginners and building wealth

Connect with Thamina Stoll:

LinkedIn: https://www.linkedin.com/in/thaminastoll/

Instagram: https://www.instagram.com/accounts/login/?next=https%3A%2F%2Fwww.instagram.com%2Fthaminastoll%2F%3Fhl%3Den&is_from_rle

Website: https://www.thaminastoll.com/

Germany's Top 100 Women of the Year: https://www.thaminastoll.com/about

Follow Madison, Ava, and Elle:

Instagram/TikTok @20somethingplaybook

Listen to “The 20 Something Playbook”:

Spotify

https://open.spotify.com/show/1bAA0eOHthyeqJyIyWlcD3?si=Uiv2K4tmRKGHbD6Pns6KeQ

Apple Podcasts

https://podcasts.apple.com/ca/podcast/the-20-something-playbook/id1801522743

Amazon Podcasts

https://music.amazon.com/es-us/podcasts/5db7484e-4184-464c-b6d9-706adc37f7d5/the-20-something-playbook

iHeart

https://www.iheart.com/podcast/269-the-20-something-playbook-269958812/?cmp=web_share&embed=true

Watch Volume One of "The 20 Something Playbook" on YouTube: https://youtube.com/playlist?list=PL1Rs9oUYUlEcNigeakfAcHDyKl2mSlAJ6&si=Krq-KY-PoR_uK9gJ

Behind The Scenes | Filming the Podcast in NYC and California: https://www.youtube.com/watch?v=KNaj9QhEOls&list=PL1Rs9oUYUlEf6yeVawHLs6G3UUaj4EACf

M.A.E. Chats: https://www.youtube.com/playlist?list=PL1Rs9oUYUlEc6OKwezm67aF1x85L9RBSF

To advertise on this podcast please email: macgregormadison@gmail.com

Music from #Uppbeat (free for Creators!):

https://uppbeat.io/t/doug-organ/theme-from-a-lift

License code: BPZMSBJOKUAS89NB

#financialliteracy #financialindependence #20something #podcast

Hosted on Acast. See acast.com/privacy for more information.

M.A.E. Chats: How The Summer I Turned Pretty Captures The Uncertainty of Your 20s

Tue, 23 Sep 2025 05:00:00 GMT

Join us in this episode of M.A.E. Chats as we dive into the captivating world of The Summer I Turned Pretty and explore how it perfectly encapsulates the uncertainty of your 20s. With its relatable characters and coming-of-age storylines, this series is all about embracing the summer vibes that come with newfound freedom and independence. As we navigate the ups and downs of life, we learn valuable life lessons about chasing dreams, cultivating a growth mindset, and surrounding ourselves with good vibes that promote personal growth. The Summer I Turned Pretty is more than just a story - it's a reflection of our own journeys, filled with moments of self-discovery, uncertainty, and the pursuit of happiness. Tune in to find out how this series captures the essence of our twenties and the importance of staying true to ourselves as we navigate the twists and turns of life.

Follow Madison, Ava, and Elle:

Instagram/TikTok @20somethingplaybook

Listen to “The 20 Something Playbook”:

Spotify

https://open.spotify.com/show/1bAA0eOHthyeqJyIyWlcD3?si=Uiv2K4tmRKGHbD6Pns6KeQ

Apple Podcasts

https://podcasts.apple.com/ca/podcast/the-20-something-playbook/id1801522743

Amazon Podcasts

https://music.amazon.com/es-us/podcasts/5db7484e-4184-464c-b6d9-706adc37f7d5/the-20-something-playbook

iHeart

https://www.iheart.com/podcast/269-the-20-something-playbook-269958812/?cmp=web_share&embed=true

Watch Volume One of "The 20 Something Playbook" on YouTube: https://youtube.com/playlist?list=PL1Rs9oUYUlEcNigeakfAcHDyKl2mSlAJ6&si=Krq-KY-PoR_uK9gJ

Behind The Scenes | Filming the Podcast in NYC and California: https://www.youtube.com/watch?v=KNaj9QhEOls&list=PL1Rs9oUYUlEf6yeVawHLs6G3UUaj4EACf

M.A.E. Chats: https://www.youtube.com/playlist?list=PL1Rs9oUYUlEc6OKwezm67aF1x85L9RBSF

To advertise on this podcast please email: macgregormadison@gmail.com

Music from #Uppbeat (free for Creators!):

https://uppbeat.io/t/doug-organ/theme-from-a-lift

License code: BPZMSBJOKUAS89NB

Hosted on Acast. See acast.com/privacy for more information.

Chapter Twelve: How To Be Healthy In Your 20s with Josie Santi

Tue, 16 Sep 2025 05:00:00 GMT

Wellness in your 20s with Josie Santi (The Everygirl, 1M+ downloads): Authenticity, joy, and self-discovery for ambitious women.

EPISODE 12 of The 20 Something Playbook Podcast – New episodes every Tuesday!

Timestamps:

00:00 Intro & Guest Welcome

03:15 Josie’s 20s transformation story

10:45 Redefining wellness: what really matters

19:30 Moving from Chicago to LA – chasing dreams

27:00 Joy as a lifestyle: Josie’s #1 takeaway

👇 What’s your #1 wellness lesson from your 20s? Drop it in the comments and join the conversation!

For more on Josie Santi:

Instagram: https://www.instagram.com/josie.santi/?hl=en

The Everygirl podcast: https://www.theeverygirlpodcast.com/

The Everygirl podcast Instagram: https://www.instagram.com/theeverygirlpodcast/

About Josie Santi: https://theeverygirl.com/contributor/josie-santi/

Follow Madison, Ava, and Elle:

Instagram/TikTok @20somethingplaybook

Listen to “The 20 Something Playbook”:

Spotify

https://open.spotify.com/show/1bAA0eOHthyeqJyIyWlcD3?si=Uiv2K4tmRKGHbD6Pns6KeQ

Apple Podcasts

https://podcasts.apple.com/ca/podcast/the-20-something-playbook/id1801522743

Amazon Podcasts

https://music.amazon.com/es-us/podcasts/5db7484e-4184-464c-b6d9-706adc37f7d5/the-20-something-playbook

iHeart

https://www.iheart.com/podcast/269-the-20-something-playbook-269958812/?cmp=web_share&embed=true

Watch Volume One of "The 20 Something Playbook" on YouTube: https://youtube.com/playlist?list=PL1Rs9oUYUlEcNigeakfAcHDyKl2mSlAJ6&si=Krq-KY-PoR_uK9gJ

Behind The Scenes | Filming the Podcast in NYC and California: https://www.youtube.com/watch?v=KNaj9QhEOls&list=PL1Rs9oUYUlEf6yeVawHLs6G3UUaj4EACf

M.A.E. Chats: https://www.youtube.com/playlist?list=PL1Rs9oUYUlEc6OKwezm67aF1x85L9RBSF

To advertise on this podcast please email: macgregormadison@gmail.com

Music from #Uppbeat (free for Creators!):

https://uppbeat.io/t/doug-organ/theme-from-a-lift

License code: BPZMSBJOKUAS89NB

#wellness #20something #podcast

Hosted on Acast. See acast.com/privacy for more information.

M.A.E. Chats: How we navigate comparing ourselves to each other

Tue, 09 Sep 2025 05:00:00 GMT

In this chat, Madison, Ava, and Elle dive into how they navigate comparison as sisters (and twins). They share what they have learned over the years, what's worked, what doesn't and struggles they've had to overcome as they've grown up. Especially during your 20s, it's easy to fall into the comparison trap. We hope this conversation is helpful, and at the very least, we hope you get a chuckle or two out of our funny stories.

Listen to episodes:

Spotify: https://open.spotify.com/show/1bAA0eOHthyeqJyIyWlcD3?si=cPnjpInHTDSGuMWc3p7ufQ

Apple Podcasts: https://podcasts.apple.com/ca/podcast/the-20-something-playbook/id1801522743

TikTok: https://www.tiktok.com/@20somethingplaybook

Instagram: https://www.instagram.com/20somethingplaybook?utm_source=ig_web_button_share_sheet&igsh=MXh5YWgwc244YmxrZA==

Thank you for tuning in!!

Hosted on Acast. See acast.com/privacy for more information.

Chapter Eleven: Mastering Your Mental Health in Your 20s with Startup Founder Mackenzie Drazan Cook

Tue, 02 Sep 2025 05:00:00 GMT

This week on The 20 Something Playbook we’re joined by Mackenzie Drazan Cook— founder of T.E.A.M. (Teaching Everyone About Mental Health), CEO of mental health software startup MiResource and a 2022 Forbes 30 Under 30 honoree.

In this powerful conversation, Mackenzie opens up about the defining lessons of her 20s: from navigating relationships and career pivots to facing loss and resilience. She shares the single most important factor in figuring out what you actually want to do with your life — plus how losing her sister while in college shaped her perspective on hardship and growth.

If you’re in your 20s (or just looking for guidance and inspiration), this episode is packed with insights you don’t want to miss.

🎧 Tune in now and take away the tools to help you navigate your own journey of self-discovery and growth.

For more on Mackenzie Drazan Cook:

MiResource (find the right mental health care for you): https://miresource.com/

T.E.A.M. Instagram (Madison, Ava and Elle run the social media): https://www.instagram.com/myteam.social/?hl=en

Mackenzie Instagram: https://www.instagram.com/mackenziedrazan/?hl=en

More on Mackenzie: https://www.wbenc.org/speakers/mackenzie-drazan/

Follow Madison, Ava, and Elle:

Instagram/TikTok @20somethingplaybook

Listen to “The 20 Something Playbook”:

Spotify

https://open.spotify.com/show/1bAA0eOHthyeqJyIyWlcD3?si=Uiv2K4tmRKGHbD6Pns6KeQ

Apple Podcasts

https://podcasts.apple.com/ca/podcast/the-20-something-playbook/id1801522743

Amazon Podcasts

https://music.amazon.com/es-us/podcasts/5db7484e-4184-464c-b6d9-706adc37f7d5/the-20-something-playbook

iHeart

https://www.iheart.com/podcast/269-the-20-something-playbook-269958812/?cmp=web_share&embed=true

Watch Volume One of "The 20 Something Playbook" on YouTube: https://youtube.com/playlist?list=PL1Rs9oUYUlEcNigeakfAcHDyKl2mSlAJ6&si=Krq-KY-PoR_uK9gJ

Behind The Scenes | Filming the Podcast in NYC and California: https://www.youtube.com/watch?v=KNaj9QhEOls&list=PL1Rs9oUYUlEf6yeVawHLs6G3UUaj4EACf

M.A.E. Chats: https://www.youtube.com/playlist?list=PL1Rs9oUYUlEc6OKwezm67aF1x85L9RBSF

To advertise on this podcast please email: macgregormadison@gmail.com

Music from #Uppbeat (free for Creators!):

https://uppbeat.io/t/doug-organ/theme-from-a-lift

License code: BPZMSBJOKUAS89NB

Hosted on Acast. See acast.com/privacy for more information.

M.A.E. Chats: When things don’t go to plan, you’re learning not failing.

Tue, 26 Aug 2025 07:00:00 GMT

The 20's is all about trying and failing, and trying all over again. But what we don't recognize is that these aren't failures, they're learnings! Madison, Ava and Elle talk about their rollercoaster experience in the screenwriting industry and how important every 'failure' has been to get them where they are today.

Watch this episode on YouTube: https://youtu.be/iHNJnsCLHPI

Listen to episodes:

Spotify: https://open.spotify.com/show/1bAA0eOHthyeqJyIyWlcD3?si=cPnjpInHTDSGuMWc3p7ufQ

Apple Podcasts: https://podcasts.apple.com/ca/podcast/the-20-something-playbook/id1801522743

TikTok: https://www.tiktok.com/@20somethingplaybook

Instagram: https://www.instagram.com/20somethingplaybook?utm_source=ig_web_button_share_sheet&igsh=MXh5YWgwc244YmxrZA==

Thank you for tuning in!!

Hosted on Acast. See acast.com/privacy for more information.

Chapter Ten: From Open Heart Surgery to Hosting Her Own Show with Madison Tevlin

Tue, 19 Aug 2025 07:00:00 GMT

In this week's chapter of The 20 Something Playbook we sat down with actor, host of "21 Questions", advocate and public speaker Madison Tevlin. Back in 2021, Madison interviewed our co-host (Madison MacGregor) for her show "Who Do You Think I Am". Madison Tevlin has been nominated for a Canadian Screen Award.

Madison, only 23, bravely shares her personal experience of undergoing open heart surgery, revealing the highs and lows of her journey. Madison holds nothing back, giving us a candid look at what it's like to go through such a life-changing event while pursuing your dreams...

Get ready for a heartfelt and inspiring chat, Madison has let nothing stop her in the pursuit of her passions, and she's only just getting started!

For more Madison Tevlin:

Website: https://www.madisontevlin.com/

Instagram: https://www.instagram.com/madisontevlin/

Maddie's podcast "21 Questions" coming soon:

https://participate.sxsw.com/flow/sxsw/sxsw26/community-voting-sxsw/page/community-voting/session/1753389225843001bJwc

Follow Madison, Ava, and Elle:

Instagram @20somethingplaybook

TikTok @20somethingplaybook

Listen to “The 20 Something Playbook”:

Spotify

https://open.spotify.com/show/1bAA0eOHthyeqJyIyWlcD3?si=Uiv2K4tmRKGHbD6Pns6KeQ

Apple Podcasts

https://podcasts.apple.com/ca/podcast/the-20-something-playbook/id1801522743

Amazon Podcasts

https://music.amazon.com/es-us/podcasts/5db7484e-4184-464c-b6d9-706adc37f7d5/the-20-something-playbook

iHeart

https://www.iheart.com/podcast/269-the-20-something-playbook-269958812/?cmp=web_share&embed=true

Watch Volume One of "The 20 Something Playbook" on YouTube: https://youtube.com/playlist?list=PL1Rs9oUYUlEcNigeakfAcHDyKl2mSlAJ6&si=Krq-KY-PoR_uK9gJ

Behind The Scenes | Filming the Podcast in NYC and California: https://www.youtube.com/watch?v=KNaj9QhEOls&list=PL1Rs9oUYUlEf6yeVawHLs6G3UUaj4EACf

To advertise on this podcast please email: macgregormadison@gmail.com

Music from #Uppbeat (free for Creators!):

https://uppbeat.io/t/doug-organ/theme-from-a-lift

License code: BPZMSBJOKUAS89NB

Hosted on Acast. See acast.com/privacy for more information.

M.A.E. Chats: The Most HILARIOUS Moments in Podcasting

Tue, 12 Aug 2025 07:00:00 GMT

Here's a sneak peek into the making of our very first season! From mishaps to funny moments, it's been a wild ride. We hope you enjoy!

Volume One Episodes: https://www.youtube.com/playlist?list=PL1Rs9oUYUlEcNigeakfAcHDyKl2mSlAJ6

Volume One BTS Vlogs (NYC and Cali): https://www.youtube.com/playlist?list=PL1Rs9oUYUlEc6OKwezm67aF1x85L9RBSF

Hosted on Acast. See acast.com/privacy for more information.

Chapter Nine: From Healing an Eating Disorder to Founding a Healthy Snack Brand With Sydney Karmes-Wainer

Tue, 05 Aug 2025 07:00:00 GMT

This week on The 20 Something Playbook, we sit down with Sydney Karmes-Wainer an inspiring 20-something CEO and founder of the healthy snack brand French Squirrel.

Sydney opens up about her journey from disordered eating to launching a mission-driven company that's now stocked at stores like Erewhon, The Fresh Market and more.

We talk about entrepreneurship, personal growth, wellness, and what it really takes to turn a painful chapter into a purpose-filled business. Learn how she overcame obstacles, stayed true to her vision, and created a business that makes a difference in people's lives. Sydney's story is a testament to the power of following your passion and pursuing your dreams, no matter how young you are!

Topics we cover:

- Healing your relationship with food in your 20s

- Building a business from scratch (without

burning out)

- Entrepreneurship lessons no one talks about

- Why your struggles can become your

superpower

To find French Squirrel snacks near you: https://frenchsquirrel.com/

Instagram:

@frenchsquirrel.co

@sydney_kw

More on Sydney: https://www.bristolfarms.com/founders/mtf-sydney-karmes-wainer-of-french-squirrel

Follow Madison, Ava, and Elle:

Instagram @20somethingplaybook

TikTok @20somethingplaybook

Listen to “The 20 Something Playbook”:

Spotify

https://open.spotify.com/show/1bAA0eOHthyeqJyIyWlcD3?si=Uiv2K4tmRKGHbD6Pns6KeQ

Apple Podcasts

https://podcasts.apple.com/ca/podcast/the-20-something-playbook/id1801522743

Amazon Podcasts

https://music.amazon.com/es-us/podcasts/5db7484e-4184-464c-b6d9-706adc37f7d5/the-20-something-playbook

iHeart

https://www.iheart.com/podcast/269-the-20-something-playbook-269958812/?cmp=web_share&embed=true

Watch Volume One of "The 20 Something Playbook" on YouTube: https://youtube.com/playlist?list=PL1Rs9oUYUlEcNigeakfAcHDyKl2mSlAJ6&si=Krq-KY-PoR_uK9gJ

Behind The Scenes | Filming the Podcast in NYC and California: https://www.youtube.com/watch?v=KNaj9QhEOls&list=PL1Rs9oUYUlEf6yeVawHLs6G3UUaj4EACf

Thank you West Gate New York Grand Central for hosting our interview space (and stay in NYC).

BOOK YOUR STAY HERE: https://westgate.prf.hn/click/camref:1100l5227F

To advertise on this podcast please email: macgregormadison@gmail.com

Music from #Uppbeat (free for Creators!):

https://uppbeat.io/t/doug-organ/theme-from-a-lift

License code: BPZMSBJOKUAS89NB

Hosted on Acast. See acast.com/privacy for more information.

M.A.E. Chats: The Soundtrack to Your 20s

Tue, 29 Jul 2025 07:00:00 GMT

We didn’t get tickets to the Gracie Abrams concert in Toronto last weekend, so we talked about our fave songs about the 20s LIVE on our YouTube Channel instead.

We each made a list of our top 3 “20s Anthems” and haven’t revealed them to each other until this video.

What song is defining your 20s right now? Let us know in the comments below.

Watch The 20 Something Playbook Episodes here: https://youtube.com/playlist?list=PL1Rs9oUYUlEcNigeakfAcHDyKl2mSlAJ6&si=8zPCw5kYA_bQCQE1

M.A.E. Chats: https://www.youtube.com/playlist?list=PL1Rs9oUYUlEc6OKwezm67aF1x85L9RBSF

Hosted on Acast. See acast.com/privacy for more information.

Chapter Eight: Following Your Dreams in Your 20s While Navigating Chronic Illness with Alex Chaves

Tue, 22 Jul 2025 07:00:00 GMT

This week on The 20 Something Playbook we're joined by actor and dancer Alexandra Chaves, best known for her role as Piper on The Next Step.

In this heartfelt and honest conversation, Alex opens up about what it's really like to chase big dreams in your 20s while living with a chronic illness. Diagnosed with colitis as a teen, she shares how she's learned to manage her health while continuing to show up fully for her passions.

From setbacks to breakthroughs, this episode is packed with insight, resilience, and inspiration. It's a powerful reminder that we're all navigating something beyond our control (especially in our 20s) and the real growth comes when we learn to embrace the full journey, even when it takes us far outside our comfort zone.

Follow Alex on Instagram: https://www.instagram.com/alexandrachaves/?hl=en

TikTok: https://www.tiktok.com/@alexandra.chaves?lang=en

For more chats with Alex: https://www.instagram.com/reel/C0H5wFzPyZO/?utm_source=ig_web_copy_link&igsh=MzRlODBiNWFlZA==

Follow Madison, Ava, and Elle:

Instagram @20somethingplaybook

TikTok @20somethingplaybook

Listen to “The 20 Something Playbook”:

Spotify

https://open.spotify.com/show/1bAA0eOHthyeqJyIyWlcD3?si=Uiv2K4tmRKGHbD6Pns6KeQ

Apple Podcasts

https://podcasts.apple.com/ca/podcast/the-20-something-playbook/id1801522743

Amazon Podcasts

https://music.amazon.com/es-us/podcasts/5db7484e-4184-464c-b6d9-706adc37f7d5/the-20-something-playbook

iHeart

https://www.iheart.com/podcast/269-the-20-something-playbook-269958812/?cmp=web_share&embed=true

Watch Volume One of "The 20 Something Playbook" on YouTube: https://youtube.com/playlist?list=PL1Rs9oUYUlEcNigeakfAcHDyKl2mSlAJ6&si=Krq-KY-PoR_uK9gJ

Behind The Scenes | Filming the Podcast in NYC and California: https://www.youtube.com/watch?v=KNaj9QhEOls&list=PL1Rs9oUYUlEf6yeVawHLs6G3UUaj4EACf

To advertise on this podcast please email: macgregormadison@gmail.com

Music from #Uppbeat (free for Creators!):

https://uppbeat.io/t/doug-organ/theme-from-a-lift

License code: BPZMSBJOKUAS89NB

Hosted on Acast. See acast.com/privacy for more information.

M.A.E. Chats: 20s Birthday Reflections, Change, and the Trenches

Tue, 15 Jul 2025 07:00:00 GMT

This week on The 20 Something Playbook, we went LIVE on YouTube for a chat about 20s birthday reflections (Ava and Elle turned 23 last week), change and the trenches… all while sharing ONE MIC, which was a big challenge for us, lol.

In this episode “M.A.E. Chats: 20s Birthday Reflections, Change, and the Trenches” we’re talking about our experiences, mistakes, and successes. From relationships and friendships to career and personal growth, get ready for a raw and honest conversation that will make you laugh, cry, and feel less alone in the trenches of your 20s.

Full episode is out NOW on YouTube: https://www.youtube.com/live/FJfwF3tyk5c?si=WQ9n5sMk8wDxnKx9

Watch The 20 Something Playbook Episodes here: https://youtube.com/playlist?list=PL1Rs9oUYUlEcNigeakfAcHDyKl2mSlAJ6&si=8zPCw5kYA_bQCQE1

Chapter 3 of The 20 Something Playbook: https://youtu.be/vyVZJWe9iPs?si=zrOacLgV41O6sG5N

M.A.E. Chat from last week: https://www.youtube.com/live/FJfwF3tyk5c?si=iqTHTW1UepjlVvdb

Hosted on Acast. See acast.com/privacy for more information.

Chapter Seven: Med School in Your 20s With Dr. Gabriela Asturias, Stanford MD from Guatemala

Tue, 08 Jul 2025 07:00:00 GMT

Meet Dr. Gabriela Asturias, an inspiring Stanford psych resident who achieved her dream of becoming a doctor in her 20s! Born and raised in Guatemala, Gabriela's journey to success is a testament to her hard work, dedication, and perseverance. In this video, we get to know Gabriela's story, from Duke University to her residency at Stanford, including starting a business while in school (Co-Founder and COO at MiResource) and navigating mental health challenges along the way. Get ready to be motivated by her remarkable achievements and learn about her experiences as a young doctor. Watch until the end to discover the challenges she overcame and the lessons she learned along the way.

Dr Gabriela recently won the prestigious Princess of Girona Prize 2025. She was on the Forbes 30 under 30 List in 2022 and MIT Tech Review 35 under 35.

Follow Dr Gabi at:

Instagram: https://www.instagram.com/gabrielaasturiasgt/?hl=en

LinkedIn: https://www.linkedin.com/in/gabriela-asturias/

Website: https://miresource.com/provider/gabriela-asturias-ZbuN

Miresource: https://miresource.com

For more mental health chats @myteam.social on Instagram

Follow Madison, Ava, and Elle:

Instagram @20somethingplaybook

TikTok @20somethingplaybook

Listen to “The 20 Something Playbook”:

Spotify

https://open.spotify.com/show/1bAA0eOHthyeqJyIyWlcD3?si=Uiv2K4tmRKGHbD6Pns6KeQ

Apple Podcasts

https://podcasts.apple.com/ca/podcast/the-20-something-playbook/id1801522743

Amazon Podcasts

https://music.amazon.com/es-us/podcasts/5db7484e-4184-464c-b6d9-706adc37f7d5/the-20-something-playbook

iHeart

https://www.iheart.com/podcast/269-the-20-something-playbook-269958812/?cmp=web_share&embed=true

Watch Volume One of "The 20 Something Playbook" on YouTube: https://youtube.com/playlist?list=PL1Rs9oUYUlEcNigeakfAcHDyKl2mSlAJ6&si=Krq-KY-PoR_uK9gJ

Behind The Scenes | Filming the Podcast in NYC and California: https://www.youtube.com/watch?v=KNaj9QhEOls&list=PL1Rs9oUYUlEf6yeVawHLs6G3UUaj4EACf

To advertise on this podcast please email: macgregormadison@gmail.com

Music from #Uppbeat (free for Creators!):

https://uppbeat.io/t/doug-organ/theme-from-a-lift

License code: BPZMSBJOKUAS89NB

Hosted on Acast. See acast.com/privacy for more information.

M.A.E. Chats: Navigating the Job Market in Your 20s

Tue, 08 Jul 2025 06:59:00 GMT

Are you tired of feeling overwhelmed and frustrated with the job market? Madison, Ava and Elle talk about their current job market struggles in their 20s, from the stress of unemployment to being employed, and trying not to crash out in the process. From dealing with rejection and self-doubt to finding ways to stay motivated and focused, we're sharing our unfiltered thoughts. If you're struggling to find a job or feeling stuck in your career, this chat is for you!

Watch this episode on YouTube: https://www.youtube.com/live/e8WaMEzyYD8?si=q5ttMQ2dvhIYsZUk

Chapter Three with Britt Baker (The Artist's Way): https://youtu.be/vyVZJWe9iPs?si=SI6oUWnVnn2TOeJZ

Chapter Six: Postgrad Playbook with Jahleane Dolne: https://youtu.be/t0YqzYN90Z4?si=m4D8lUH5gxz7hLCg

Volume One of The 20 Something Playbook is out now (new episodes every Tuesday): https://youtube.com/playlist?list=PL1Rs9oUYUlEcNigeakfAcHDyKl2mSlAJ6&si=3gNbVkQVqg6abe60

Listen to episodes:

Spotify: https://open.spotify.com/show/1bAA0eOHthyeqJyIyWlcD3?si=cPnjpInHTDSGuMWc3p7ufQ

Apple Podcasts: https://podcasts.apple.com/ca/podcast/the-20-something-playbook/id1801522743

TikTok: https://www.tiktok.com/@20somethingplaybook

Instagram: https://www.instagram.com/20somethingplaybook?utm_source=ig_web_button_share_sheet&igsh=MXh5YWgwc244YmxrZA==

Thank you for tuning in!!

Hosted on Acast. See acast.com/privacy for more information.

Chapter Six: Meet Jahleane Dolne, Creator of The Postgrad Playbook

Tue, 01 Jul 2025 07:00:00 GMT

This week on The 20 Something Playbook we're joined by Jahleane Dolne, founder of The Postgrad Playbook. In this episode, Jahleane shares her journey behind creating a comprehensive guide for post-graduates. From navigating the challenges of adulthood to finding success in the real world, The Postgrad Playbook is a game-changer for anyone looking to thrive beyond college/university. Tune in to learn more about Jahleane's journey, her approach to post-grad life, and how her playbook can help you achieve your goals.

The Postgrad Playbook: https://thepostgradsplaybook.com/

Follow Jahleane Dolne on LinkedIn: https://www.linkedin.com/in/jahleane/

Jahleane's podcast "Make Up Your Mind": https://open.spotify.com/show/5NPfYGhYW2QwAWQOB0L7Dz?si=3bb44687e0bc46ac

Follow Jahleane on IG:

@jahleane

@thepostgradplaybook

Follow Madison, Ava, and Elle:

Instagram @20somethingplaybook

TikTok @20somethingplaybook

Listen to “The 20 Something Playbook”:

Spotify

https://open.spotify.com/show/1bAA0eOHthyeqJyIyWlcD3?si=Uiv2K4tmRKGHbD6Pns6KeQ

Apple Podcasts

https://podcasts.apple.com/ca/podcast/the-20-something-playbook/id1801522743

Watch Volume One of "The 20 Something Playbook" on YouTube: https://youtube.com/playlist?list=PL1Rs9oUYUlEcNigeakfAcHDyKl2mSlAJ6&si=Krq-KY-PoR_uK9gJ

Behind The Scenes | Filming the Podcast in NYC and California: https://www.youtube.com/watch?v=KNaj9QhEOls&list=PL1Rs9oUYUlEf6yeVawHLs6G3UUaj4EACf

Thank you West Gate New York Grand Central for hosting our interview space (and stay in NYC).

BOOK YOUR STAY HERE: https://westgate.prf.hn/click/camref:1100l5227F

To advertise on this podcast please email: macgregormadison@gmail.com

Music from #Uppbeat (free for Creators!):

https://uppbeat.io/t/doug-organ/theme-from-a-lift

License code: BPZMSBJOKUAS89NB

Hosted on Acast. See acast.com/privacy for more information.

Chapter Five: From Overdose to 2+ Years Sober, Courtney Riddle's Journey to Sobriety at 26

Tue, 24 Jun 2025 07:00:00 GMT

In this episode of The 20 Something Playbook we're joined by Courtney Riddle, a sobriety advocate and founder of Courtney Rose Style. Courtney shares her incredible journey of 2+ years of sobriety in her 20s, while battling OCD, anxiety, and depression. She opens up about her struggles, triumphs, and the lessons she's learned along the way. In her early 20s, she hit rock bottom and realized she needed to make a change. From the darkest moments of her addiction to her recovery, she’s holding nothing back in this raw and honest interview. Get ready for a real and unfiltered look at what it takes to overcome addiction and start living your best life in your 20s. If you or someone you know is struggling with alcohol addiction, this video is for you. We filmed in her beautiful rom-com style apartment in NYC. Decorated by Courtney, who you can tell works in fashion ;)

In this episode:

00:00 - 00:52 Intro

00:52 - 02:49 Three words to describe your 20s

02:49 - 07:38 Sobriety journey begins

07:38 - 10:52 Drinking to cope with anxiety

10:52 - 14:52 When drinking got bad

14:52 - 17:12 Why my 20s are fabulous + talking about sobriety

17:12 - 21:48 Social media, social anxiety, and why our generation drinks

21:48 - 28:38 Fashion industry in your 20s

28:38 - 33:25 Sobriety and mental health

33:25 - 38:48 Sobriety advice

38:48 - 42:18 Family and friend support

42:18 - 46:08 How your definition of success changes in your 20s

46:08 - 51:41 Dating sober and meeting “the one” in your 20s

Follow Courtney on Instagram: @courtneyrosestyle

More Interviews with Courtney (on @myteam.social on Instagram):

Sobriety Chat 1: https://www.instagram.com/reel/C_MOi_2MejM/?utm_source=ig_web_copy_link&igsh=MzRlODBiNWFlZA==

Sobriety Chat 2: https://www.instagram.com/reel/DAmWC_UMVhB/?utm_source=ig_web_copy_link&igsh=MzRlODBiNWFlZA==

Follow Madison, Ava, and Elle:

Instagram/TikTok @20somethingplaybook

Listen to “The 20 Something Playbook”:

Spotify https://open.spotify.com/show/1bAA0eOHthyeqJyIyWlcD3?si=Uiv2K4tmRKGHbD6Pns6KeQ

Apple Podcasts https://podcasts.apple.com/ca/podcast/the-20-something-playbook/id1801522743

Watch Volume One of "The 20 Something Playbook" on YouTube: https://youtube.com/playlist?list=PL1Rs9oUYUlEcNigeakfAcHDyKl2mSlAJ6&si=Krq-KY-PoR_uK9gJ

Behind The Scenes | Filming the Podcast in NYC and California: https://www.youtube.com/watch?v=KNaj9QhEOls&list=PL1Rs9oUYUlEf6yeVawHLs6G3UUaj4EACf

Thank you West Gate New York Grand Central for hosting our stay in NYC. BOOK YOUR STAY HERE: https://westgate.prf.hn/click/camref:1100l5227F

Music from #Uppbeat (free for Creators!):

https://uppbeat.io/t/doug-organ/theme-from-a-lift

License code: BPZMSBJOKUAS89NB

Hosted on Acast. See acast.com/privacy for more information.

Chapter Four: Surviving NYC in Your 20s: Mastering LinkedIn For Success with Christine Göös

Tue, 17 Jun 2025 07:00:00 GMT

Are you a young professional in your 20s trying to make it big in the city that never sleeps? Mastering LinkedIn is key to unlocking success in NYC! In this episode, award-winning marketing leader Christine Göös shares her top tips and strategies for optimizing your LinkedIn profile, growing your network, and landing your dream job in the competitive New York City job market. From building a strong personal brand to navigating online networking, we've got you covered. Whether you're a recent college grad or just looking to level up your career, this episode is for you. So, what are you waiting for? Press play and start mastering LinkedIn for success in NYC (and beyond)!

In this episode:

00:00 - Intro

00:48 - 02:22 How we met + unhinged things she did in her 20s to make it in NYC

03:37 - 04:08 How hard it is to move to NYC

06:41 - 07:46 Be your own publicist

08:08 - 09:42 Building your brand and resume

10:28 - 11:08 Posting content on LinkedIn + future-proofing your career

11:08 - 13:13 Using LinkedIn for Gen Z + bad job market + getting laid off

13:31 - 15:48 Job advice for 20-somethings

15:48 - 16:03 Resume tips

20:08 - 20:42 Rock bottom in your 20s: miserable in NYC

22:12 - 23:37 Panic attacks in Macy’s dressing room

23:37 - 24:42 Fake it till you make it—confidence advice

25:05 - 25:35 Three words to describe your 20s

25:35 - 26:59 Writing tips + how to become a better writer

33:21 - 34:08 Titles don’t matter

34:08 - 35:08 Redefining success from 20s to now

Follow Christine Göös on LinkedIn: https://www.linkedin.com/in/christinegoos/ Christine's podcast House of Content: https://podcasts.apple.com/us/podcast/house-of-content/id1681192360 Christine's website: https://www.christinegoos.com

Follow Madison, Ava, and Elle:

Instagram/TikTok @20somethingplaybook

Listen to “The 20 Something Playbook”:

Spotify: https://open.spotify.com/show/1bAA0eOHthyeqJyIyWlcD3?si=Uiv2K4tmRKGHbD6Pns6KeQ

Apple Podcasts: https://podcasts.apple.com/ca/podcast/the-20-something-playbook/id1801522743

Watch Volume One of "The 20 Something Playbook" on YouTube: https://youtube.com/playlist?list=PL1Rs9oUYUlEcNigeakfAcHDyKl2mSlAJ6&si=Krq-KY-PoR_uK9gJ

Behind The Scenes | Filming the Podcast in NYC and California: https://www.youtube.com/watch?v=KNaj9QhEOls&list=PL1Rs9oUYUlEf6yeVawHLs6G3UUaj4EACf

Thank you West Gate New York Grand Central for hosting our interview space (and stay in NYC). BOOK YOUR STAY HERE: https://westgate.prf.hn/click/camref:1100l5227F

Music from #Uppbeat (free for Creators!): https://uppbeat.io/t/doug-organ/theme-from-a-lift License code: BPZMSBJOKUAS89NB

Hosted on Acast. See acast.com/privacy for more information.

Chapter Three: From Ice Cream Scooper to Self-Made Millionaire with Co-Founder of Dow Janes

Tue, 10 Jun 2025 07:00:00 GMT

Ready to break free from the pressure of needing to have it all figured out? In this episode we chat with Britt Williams Baker, co-founder of Dow Janes - one of the fastest growing companies in the United States teaching financial literacy and strategies to build wealth. Britt went from scooping ice cream to becoming a self made millionaire in her 30s. She shares strategies, mindset shifts, and habits that enabled her to achieve financial freedom at a young age. From working in consulting, to attending Harvard to biking around New Zealand, Britt used her 20s for exploration. In this convo we dive into the benefits of living in the present and letting go of the need for perfection. So, if you're tired of feeling stuck and ready to start having the time of your life in your 20s, tune in!

In this episode:

00:00 - Intro

01:00 - Down Janes origin

02:00 - How we got Dow Janes

01:55 - Three words to describe your 20s

02:13 - 03:02 What were you doing in your 20s?

03:06 - 04:06 Did you always know what you wanted to do?

04:15 - 04:45 Biggest belief shift in your 20s

04:45 - 05:54 Pivot moments + Harvard Business School

06:33 - 07:17 Feeling lost in your 20s advice

07:17 - 07:30 The 20s are for exploring

08:05 - 09:20 Learning compound interest at 7 + first financial mistakes

09:24 - 09:51 Not knowing how to use a credit card

09:51 - 10:30 Finance advice for your 20s

12:15 - Scooping ice cream a year before Dow Janes

14:40 - 15:45 Becoming a self-made millionaire in your 20s

15:50 - 17:10 Rock bottom moments and navigating them

21:10 - 21:50 Feeling like you have no skills in your 20s

22:40 - 23:35 Measuring success in your 20s

23:35 - 25:55 Figuring yourself out with The Artist’s Way

25:58 - 27:06 #1 financial tip: align spending with your values

31:15 - 33:10 Transforming in your 20s

33:10 - 34:05 Saturn return + “claiming what you want”

37:25 - 39:15 Dating in your 20s

For more on taking control of your finances, check out Dow Janes: https://www.dowjanes.com/

Follow Dow Janes on Instagram: https://www.instagram.com/dow.janes/?hl=en

Follow Madison, Ava, and Elle:

Instagram/TikTok @20somethingplaybook

Listen to “The 20 Something Playbook”:

Apple Podcasts: https://podcasts.apple.com/ca/podcast/the-20-something-playbook/id1801522743

Watch "The 20 Something Playbook": https://www.youtube.com/@20SomethingPlaybook

20 Something Playbook Episodes Volume 1: https://youtube.com/playlist?list=PL1Rs9oUYUlEcNigeakfAcHDyKl2mSlAJ6&si=az6nbfw7JV2UMTzr

Behind The Scenes | Filming the Podcast in California: https://youtu.be/pq1GV7UpTyI?si=IIUrFAIvGA98j6qy

To advertise on this podcast please email: macgregormadison@gmail.com

Music from #Uppbeat (free for Creators!): https://uppbeat.io/track/doug-organ/theme-from-a-lift?rt=uc-referral License code: BPZMSBJOKUAS89NB

Hosted on Acast. See acast.com/privacy for more information.

Chapter Two: 20-Something Survival Guide from 'Almost 30'

Tue, 03 Jun 2025 07:00:00 GMT

Are you tired of feeling stuck in your 20s? Do you feel like you're not living up to your potential? In this episode, Madison, Ava and Elle sit down with founders, authors, and co-hosts of the popular “Almost 30” podcast Krista Williams and Lindsey Simcik about how to heal and overcome the struggles of your 20s before turning 30. From letting go of past traumas to building healthy habits and relationships, we'll dive into the most important lessons you need to learn to set yourself up for success in the next decade of your life (and beyond). Whether you're struggling with anxiety, depression, or just feeling lost, this video is for you.

In This Episode:

0:00 – Setting the tone for navigating the decade of uncertainty, growth, and self-discovery.

3:40 – The Lie About Purpose & Your Career: Krista and Lindsey break down the myth that your career must be your purpose — and what it means to choose your own path instead.

8:56 – Whose Voice Are You Listening To? Is it your dad? Society? Yourself? A conversation about questioning the motivations behind your decisions.

13:48 – Figuring Out Your Gifts: How human design, astrology, and even your friends can help you understand what you actually bring to the table.

18:49 – The Portfolio Career Reality: Why your twenties may look more like a patchwork of skills than a linear trajectory — and that’s okay.

23:00 – From bartending to burning out — the jobs that humble you and the wisdom that comes after.

25:00 – Lindsey opens up about cheating, shame, and how rock bottom became her greatest teacher.

29:37 – Madison shares her fears around being single — and the rollercoaster of being deeply true to yourself while longing for connection.

31:45 – Are Your Standards Too High? (Spoiler: No): The girls unpack what “lowering your standards” really means and why soul-level connection over surface-level checklists.

34:15 – Krista keeps it real on the maturity gap, dating while fulfilled, and what the masculine can (and can’t) give you.

38:00 – How strong female friendships become the training ground for honest communication.

41:30 – Madison gets vulnerable about mental health, sickness, and the messy beauty of speaking the truth through it all.

44:10 – Krista opens up about depression, anxiety, and why sobriety helped her meet herself for the first time.

49:00 – Tiny lifestyle tweaks that made a huge difference — and what they wish they knew sooner.

50:44 – Almost 30’s new book is a companion for your twenties — with tools, stories, and love on every page.

52:10 – The most important reminder: you’re exactly where you’re supposed to be.

Order Krista and Lindsey’s book Almost 30: A Definitive Guide to a Life You Love for the Next Decade and Beyond NOW: https://static.macmillan.com/static/smp/almost-30-9781250327208/

Follow Almost 30 on Instagram/YouTube/TikTok: @almost30podcast

Follow Madison, Ava, and Elle:

Instagram & TikTok @20somethingplaybook

YouTube https://www.youtube.com/@20SomethingPlaybook

Listen to “The 20 Something Playbook”:

Spotify https://open.spotify.com/show/1bAA0eOHthyeqJyIyWlcD3?si=Uiv2K4tmRKGHbD6Pns6KeQ

Apple Podcasts https://podcasts.apple.com/ca/podcast/the-20-something-playbook/id1801522743

Thank you West Gate New York Grand Central for hosting us. BOOK YOUR STAY HERE: https://be.synxis.com/?adult=1&arrive=2025-06-07&chain=19007&child=0&clickref=1011lBkz4fuk&depart=2025-06-08&level=chain&locale=en-US&promo=PRTZ&rooms=1&utm_campaign=partnerize_wgr&utm_medium=referral&utm_source=partnerize

Music from #Uppbeat (free for Creators!): https://uppbeat.io/t/doug-organ/theme-from-a-lift

License code: BPZMSBJOKUAS89NB

Hosted on Acast. See acast.com/privacy for more information.

Chapter One: Choosing Your Hard in Your 20s

Tue, 11 Mar 2025 14:24:47 GMT

Hosted by three sisters in their 20s, The 20 Something Playbook is your guide through the good, the bad, and the ugly of this defining decade.

In this intro episode, Madison, Ava and Elle break down navigating the cross roads they've faced in their 20s, and "choosing your hard" - the mantra for making difficult decisions. We get into the mission behind The 20 Something Playbook, what to expect from future episodes, and talk over each other a little too much - it's an epidemic, we know.

We have a lot of exciting guests and conversations on the horizon, full season is available NOW! New episodes every Tuesday

In the episode:

0:00 — Intro

00:16 Turning 25, struggling & writing a book

01:35 Teen expectations vs 20s reality + book

02:14 Feeling anxious while doing something you're proud of

03:00 The scariest thing about your 20s

03:45 Storytelling is our passion

05:48 Emailing your teachers and life lessons

08:31 Working together as sisters

09:53 No guidebook for creative careers

11:34 Learning screenwriting & the journey

12:37 We talk over each other

13:52 Intense perfectionism & Steve Jobs

14:44 Punching a wall moment

16:22 Why I punched the wall

17:25 Coping mechanisms in your 20s

17:40 Not gonna get into it (lol)

21:00 Failed my driver’s test

22:46 "I feel scared" and working together

24:24 Choosing your hard with mental health

26:35 Therapy is hard too

27:37 Carrying her out of the bookstore

29:10 Supporting each other’s mental health

30:18 Less BS after going through stuff

31:04 No time for people you don’t love

31:34 Recovering people-pleaser

33:08 Great friendships in your 20s

34:15 Trading what’s good for what’s right

35:45 The positive side of being alone

36:08 Disco guy moment

36:22 Introvert life

36:59 Pursuing passions helps relationships

37:36 Business disagreement

38:48 Humility over ego

39:47 Don’t wait for a partner

41:14 Mic drop moment

41:53 Sisterly love & support

42:20 Crying this week + EFT tapping

43:49 Bananas made my ears full?

44:29 Stress baking

45:30 Childhood dog memories

46:17 Dog mom life chose me

47:09 Gap jeans are waterproof??

48:09 We had a healthy week

Listen to the intro episode now wherever you get your podcasts!

Find us at:

https://linktr.ee/20somethingplaybook

Comment questions, topics, and dream guests you'd like us to have in the playbook.

Hosted on Acast. See acast.com/privacy for more information.