For Better Or Best Podcast

Behind every level-up is a cost. In this week’s episode, Charles and Shireen get real about the sacrifices, career moves, loneliness, trust, parenting, and partnership required to build the life they enjoy today. From relocating for opportunities to balancing family and ambition, this conversation explores what success really demands behind the scenes. 00:33 - 04:45 Relationship Shaping Success Ch...

It’s birthday season on the pod! Charles and Shireen get real about milestone birthdays, birthday-trip etiquette, money, marriage, and what it really means to feel celebrated. Then things get vulnerable as Charles opens up about wanting to become a dad again, the financial pressure behind that dream, and what matters most when building a family. 00:00–03:39 - Birthday Boy Energy  Charles kick...

What does it really look like to be in a secure relationship while still having a life of your own? In Episode 44, the Kuykendolls are talking love while lit; from Crop Over in Barbados and dancing with strangers to opposite-sex friendships, boundaries, trust, independence, and the freedom that comes from knowing your partner always has your back.  2:25–4:22 - Our First Crop Over Together Shi...

Episode 43 brings up one the Kuykendolls’ most emotional and impactful conversations yet. After discussing the case of Nolan Wells, they reflect on what it means to raise Black boys in America, the difficult conversations Black parents eventually have to have with their children, and the tension between teaching kids to “shine their light” while also preparing them for moments when they may need t...

In this energetic and revealing episode, Charles and Shireen reflect on the whirlwind year of building the Oxtail Off tour from a house party into a multi‑city cultural event, sharing the highs, the financial risks, the team effort, and the emotional moments behind the scenes. They close with a candid story about landlord life, late rent, and unexpected tenant drama; because real life doesn’t stop...

The Kuykendolls are BACK and they’re celebrating 10 years of marriage! After a 6 month hiatus, Charles and Shireen recap their unforgettable anniversary weekend in Barbados; 200+ guests, surprise performances with a live band, a foam pool party/fete, and a live podcast all accompanied by hookah and stop shelf liquor😂 This extravaganza also sparked some real conversations about friendship, recipro...

Episode 40 of the Better, Best Podcast live from Revolt House at SXSW was one for the books! This conversation with Jack Howard, Head of Money Wellness at Ally Financial, was bigger than budgets and credit scores—it was about the emotional relationship we all have with money. From “poverty PTSD” to credit card cycles, from first-generation wealth building to marriage, entrepreneurship, and generat...

Marriage isn’t just the highlight reel, it’s the quirks, the compromises, the petty debates, and the deep love that keeps two people choosing each other every day. In this episode, Charles and Shireen pull back the curtain on ten years of partnership, from fur‑coat miracles to thermostat wars to the art of minding your business in your friends’ relationships. It’s honest, hilarious, and a reminder...

The holidays get real when you’re hosting two full families, juggling gift expectations, assigning rooms, and trying to keep the peace. In this episode, the Kuykendolls break down their first big Christmas in the new house — the joy, the chaos, the “Hunger Games” sleeping chart, and the sweet moments that made it all worth it. If you’ve ever tried to host during the holidays, you can relate!  0:00...

***Please excuse the audio glitch in the beginning of this episode*** In this Meta World Peace episode (number 37), Charles and Shireen sit with close friends/chosen family Bridget Kelly and René Daniela for a warm, funny, and honest conversation about real friendship in your 30s - showing up, building a village, and celebrating each other through every season. 00:00 - 03:18 Charles opens the show...

This week we welcome our first guest of the season: beauty creator, lifestyle blogger, mom, and digital OG It’s My Raye Raye. From her Tumblr beginnings to becoming one of YouTube’s early success stories, Raye breaks down how the creator landscape has evolved, how she protects her peace, and why authenticity still wins in 2026. We also get into the wild story of how we met and became friends, pare...

This Christmas‑Eve episode starts with jokes and ends with real life. Charles and Shireen are no strangers to silver linings, so the two open up the "Kevin Durant episode" talking about about grief, friendship, entrepreneurship, mental health, and the wild ride that was 2025. If you’ve been waiting for a sign to stop delaying your dreams… this is it. 3:19 - What If It All Works Out?  Reflecting on...

It's our Shaq/Scottie Pippen episode y'all! This week the Beloveds needed to keep spilling the tea about the chaotic blessings of their big move, sharing how much transparency and patience was required both at the bank and driving the streets in Houston. 00:02:17 – Kuykendolls recall their most stressful season while moving. 00:04:25 – Triple financial strain: From Airbnb rent, old mortgage, and n...

We're back! Season 4 opens with a healthy dose of chaos and comedy: Essence Fest highs, a big move to Houston, scammy movers, bird invasions, trap house apartments, and finally a realtor’s offer. Episode 33 is a rollercoaster of "broke" dreams and big laughs. 00:20 – Season 4 kicks off live from Houston ; Charles and Shireen make their grand entrance, joking about budgets, brokenness, and the glow...

Season 3 finale! We did it, Joe! Every season there's a moment of questioning whether or not to continue the pod, but the outpouring of love, support and encouragement has grown more and more, so we will keep the party going. Shireen and Charles circle back to the Oxtail Off and how they forgot to mention their silent partner; ChatGPT. Shireen says she and Charles were early on the AI bandwagon, a...

It's giving double date! We've got our first married guests, close friends and chosen family Jessica and Marcus Cromartie on today's episode. Charles kicks it off by sharing how he met Jess in NYC many years ago, while she was building her influencer profile. Now 10+ years later, they've been apart of each other's journeys into marriage/parenthood. Marcus joined the friend group 5 years ago, citin...

Take it easy! We're all coming down from the high of the Oxtail Off this weekend, and this time EP BK is in the guest seat! Charles and Shireen both share their gratitude, relief and exhaustion that comes with pulling off such an awesome event. Shireen explains how the joining of cultures is so important to her, since Charles is African American and Shireen is second generation Antiguan. Charles s...

Back in full effect, Charles and Shireen are joined by their long time friend, music manager and visionary Gordan Dillard. They kick off talking about being a transplant in NYC and hustling. Coming from the Bay, Gordan was motivated by the music industry culture on the east coast. NYC provided lessons and pressure for him, when he was living in his aunt's basement, interning at a label and working...

This week has been nonstop! Charles and Shireen kick off the episode with fatigue, citing their son CJ's recital, a Netflix screening and of course the Cowboy Carter concert. Shireen breaks down the process of paying top dollar for floor seats for Beyonce and the discovering how much more they spent compared to the website. After a bunch of calls, hemming and hawing and submitting evidence to AmEx...

This week is all about that cash money! Shireen comes in hot, saying that Charles is having an existential crisis. Charles pretends not to know what that big word means so Shireen explains how introspective Charles has been in 2025, trying to establish the work/life balance. Charles still can't believe how much money he made in 2024, both of them have reached new heights in their careers. He also...

Ok so we know we said no guests this season but an exception had to be made for Chi Town Tina, the queen mother of Charles Beloved himself! They go back to the 80's when Shontina and Charles' father were 19 and 20yrs old, married and working. Shontina explains feeling older than she was, even before kids, because life was moving fast. Enter Charles' brother and the birth of Beloved. Their parents...

Charles and Shireen are fresh off the plane from Dubai, and it's spring break! Every year they take a family trip, last year was Paris and this year their son CJ had been mentioning the Burj Kalifa nonstop, so Dubai was the choice. Charles says Mexico City was his initial pick, but after pricing it out, surprisingly Dubai made more sense. Shireen was anti Dubai because she was supposed to be pregn...

Goes to Trinidad Carnival once: and now we're being introduced to Bacchanal Beloved. Clearly the brand is strong and expanding! Shireen being of Antiguan and Jamaican descent, she's always had ties to the experience "on di road" as Charles says. His good friend Kareem is Trinidadian and wanted to experience his first carnival at home so Charles went with him. Shireen breaks down the costs of carni...

Charles and Shireen are back in their fashion bag, Charles kicks off the episode giving Shireen her flowers for not only looking good but also getting in her own corporate bag; hosting panels in tech spaces. She acknowledges enjoying moderating/interviewing, as Charles takes credit for encouraging her(2:01-5:26). Shireen revisits the sensitive subject of IVF, and shares the challenges of the proce...

Your favorite couple is back for season 3! Initially Charles was so busy with work last year that he wasn't sure he'd make the return for another season. Luckily someone approached him at AfroTech to remind him how valuable the show is so he decided to give it another go(1:12-2:45). We pick up right where we left off, sharing a recap of EssenceFest last summer, where Shireen put in extra effort to...