The Messy Parts

When Emi Nietfeld landed her dream engineering job at Google after Harvard, she thought she’d found her forever family. Then she reported sexual harassment, and the company ejected her. Now a journalist writing on work culture, Emi sits down on the blue couch with Maryam for Part 2 of their discussion to dissect why the corporate ladder is officially dead for Gen Z.

In this episode, Maryam and Emi discuss:

→ Why "bringing your whole self to work" is a trap

→ How reporting harassment revealed the dark reality of "corporate family"

→ Why today’s college grads can’t name a single company they want to work for

→ The shift from corporate status to running your own show

→ Why the economy feels like a casino to young workers

If you’ve ever wondered why an entire generation is quitting the corporate rat race, this conversation explains it.

Make sure to check out Emi’s recent NY Times article about Gen Z and work, her 2021 NY Times article about working at Google, and her book, “Acceptance: A Memoir.”

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Key Moments:

01:08 - The Recurring Google Dream 💤
Emi shares her reoccurring dream about going back to Google, missing the camaraderie and purpose, despite knowing she can never actually return.

01:53 - Reporting Sexual Harassment at Big Tech 🚨
After landing her "dream job" as an engineer, Emi faces months of HR investigations that force her to confront past traumas she thought she’d escaped.

05:06 - "Bring Your Whole Self to Work" is a Trap 🪤
Emi and Maryam unpack how casual tech cultures blur emotional boundaries, making it hard to separate your work identity from your personal life.

08:18 - "Chief People Officer" is Pure PR 🏢
Maryam and Emi discuss HR’s true purpose and why transactional workplaces can actually feel more honest.

09:07 - Staking Hope in Prestigious Institutions 🏛️
Emi reflects on why she trusted places like Harvard and Google after being let down by child protective services and the family court system in her youth.

11:51 - Choosing Computer Science for Dental Insurance 🦷
Forget chasing a passion: Emi admits she pursued tech and corporate life over graduate school because she desperately needed salary stability and dental care.

14:08 - Writing Her Way Out of the "Overcomer" Myth 📖
Emi details how a Google goal-setting class kicked off her book writing journey, and why her editor forced her to ditch the sanitized "triumph" story for the messy truth.

17:23 - The Financial & Ego Shock of Leaving Tech 💸
Emi opens up about the tough identity transition after quitting Meta to write full-time, going from having a high-status corporate badge to being an unknown author.

18:34 - Why Gen Z Fell Out of Love With Work 💔
Emi explains her research with recent college grads who refuse to climb corporate ladders and can't name a single company they actually dream of working for.

19:46 - "The Economy Feels Like a Casino" 🎰
From wanting to be entrepreneurs to chasing influence, young workers view career stability as random, rendering incremental corporate effort pointless.

26:12 - Why Gen Z Feels Less in Control Than 1960s Prisoners 🔒
Emi breaks down the "locus of control" concept and how post-COVID instability left young people struggling with learned helplessness and a loss of agency.

29:57 - Rapid Fire: Sunscreen, Crying, and Perpetual Back Pain ☀️
Emi answers the signature closing questions, reflecting on the physical cost of success, dealing with corporate anxiety, and her baseline advice for life before 35.

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“The psych ward was the best place I’ve ever been.” Not because it was good, but because home was worse.

Emi Nietfeld grew up in Minneapolis in a house so full of her mother’s hoarding that the first rule was “don’t open the door” when the social worker came. Then her dad came out as trans. By 13, Emi was in a psych ward for the first time. On the way to Harvard she lived in a foster home, stayed on sofas and in a shelter, and slept in her car.

In Part 1 of this two-part conversation, Emi sits down on the blue couch with Maryam to talk about:

→ Why she liked the psych ward better than home
→ The doctor who said “you could go to college early,” and then changed her mind
→ How the staff took away her ACT book, and why it made her want it more
→ Being asked to “package your trauma” for the college essay

You may know Emi from her recent New York Times piece on ambition and Gen Z. This is the story underneath it.

⚠️ Content note: this episode includes conversations about suicide, self-harm and eating disorders. Please take care while listening.

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Key Moments

01:24 - Her Dad Comes Out as Trans 💥
Emi describes a controlling father and a mother who coped by clearance shopping at Target, until her dad came out as trans and her parents’ marriage ended.

03:03 - The Hoarder Who Thought Her Daughter Was Disorganized 😳
After the divorce, Emi’s mom takes her to the doctor convinced she has ADD, which starts years inside the child psychiatric system.

04:42 - A “Chemical Rollercoaster” of Prescriptions 🎢
Adderall leads to Xanax, antidepressants and antipsychotics, with each new drug prompted by her reaction to the last.

07:06 - “The Best Place I’ve Ever Been”: The Psych Ward vs. Home 🚿
With mice and mold at home, Emi finds the psych ward so clean and quiet that she fills 10 notebooks.

10:22 - The Doctor Who Said “You Could Go to College Early” 🌟
After being treated as “crazy,” Emi is stunned when a psychiatrist asks where she wants to go to college. The hope falls apart within two weeks.

11:36 - “I’m Trying to Escape My Problems, Duh” 📚
When staff at her residential treatment center take away her ACT prep book, Emi decides she has to go to college and starts picturing a “book life.”

14:13 - Leaving Treatment for Foster Care “Under Duress” 🏡
Emi’s mom is pushed into a “voluntary” placement, and Emi lands at a foster home near an amazing high school. It’s her first unbroken year of school since sixth grade.

17:29 - She Thought “Rock Hard Apps” Was About Abs 💪
Emi checks out a library book expecting a fitness guide. Instead she learns that getting into college isn’t only about grades, because you have to market yourself.

19:44 - Yale Said No, So She Edited Her Story ✂️
Being upfront about her hospitalization earns Emi a “big reject” from Yale. She cuts it from her Harvard application and learns she can edit her story and keep it “technically true.”

21:10 - Couches, a Car, and a Shelter 🚗
With nowhere to go during boarding school breaks, Emi stays in a stairwell outside her mom’s apartment, with a mentor, on many sofas and in a shelter, and sleeps in her car for a few days.

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One night in 2016, Eliza Reid was cooking dinner for her four young kids when a stranger called the family landline and asked if her husband would consider running for president. Within 24 hours, a tsunami of messages followed. Eliza, a Canadian immigrant, Oxford graduate, and freelance writer, never planned to become the First Lady of Iceland. On this episode of The Messy Parts, Maryam sits down with Eliza, author of “The First Lady Next Door,” for a candid conversation about that unexpected phone call, being overlooked at receptions, and why sometimes you have to be a "nasty woman." Plus: her advice for anyone who's been laid off, feels stuck, or is afraid to say yes to something scary.

Key Moments

01:49 - The Ordinary Girl with Extraordinary Adventures 🎲
Eliza traces her path from wanting to be a flight attendant, then a lawyer, to Oxford and eventually Iceland.

03:53 - "I'll Look Like a Stalker": The Raffle Ticket That Started a Marriage 🎟️
She puts 8 of her 10 raffle tickets in one cup at an Oxford fundraiser, and he draws her name.

05:29 - "He Didn't, So I Did": Why Eliza Proposed to Her Husband 💍
Before moving to Iceland, she decides to ask him to marry her rather than wait.

11:09 - "It Felt Awful": Getting Laid Off in a New Country 💼
Eliza loses her job at a startup and then struggles to get a single interview in Iceland.

13:48 - How a Eurovision Story Launched a Freelance Career 🎤
She turns a conversation with a singer at her gym into her first assignment.

15:27 - "Your Job Is Looking for a Job": Eliza's Advice for Anyone Laid Off 🔍
Apply for things you don't fit, use your networks, and not take it too personally.

20:45 - The Landline Call That Changed Everything ☎️
A stranger calls while she's cooking dinner, and within 24 hours the messages pile up.

24:51 - "What Did You Achieve?": Imposter Syndrome as First Lady 🪞
While riting her book, Eliza doubts herself, then realizes she did her part to nudge things in the right direction.

26:11 - "Sometimes You Have to Be a Nasty Woman"🧣
How she confounded expectations, from turning down “soft” events to meeting immigrants and startup founders.

29:40 - "Life Is Messy": Why We Need to Keep Talking in a Polarized World 🌍
Eliza argues that disagreeing on point A shouldn't stop us from finding common ground.

33:43 - "Why Wasn't I More Assertive?": The Handshake Story 🤝
At receptions, people shook her husband's hand and walked right past her, and she explains the small fix that took her years to try.

36:06 - "You Have a Unique Story": Advice for Anyone Having a Crisis of Confidence ✨
In the rapid-fire close, Eliza says your own narrative can give you the tools to tackle whatever you're facing.

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"I was kicking and screaming, but I didn't have a choice." That's how Maha Abouelenein describes accepting a job as a billionaire's secretary, a role she was sure was beneath her. It turned out to be the start of a career that took her through Google, Netflix, and Gary Vee, and into running her own strategic communications agency. In this episode of The Messy Parts, Maryam talks with Maha, author of “Seven Rules of Self-Reliance,” about the hard-won lessons behind that career. Maha opens up about growing up as the only Egyptian kid in her Minnesota class, caring for her mother with MS from age 14, losing both parents, and starting over from her sister's basement. She also shares what success has cost her, and why she says she has no regrets.

Key Moments

01:31 - "Camel Jockey, Towel Head": Growing Up the Only Egyptian Kid in Minnesota 🏔️
Maha describes being the different kid in a classroom with no internet and no frame of reference for Egypt beyond camels and pyramids.

08:29 - Following Her Family Back to Egypt at 27 ❤️
After years of caring for her mother, who had MS, Maha gives up a coveted sports marketing job at General Mills to move abroad with her parents.

11:45 - The Billionaire's Job Offer She Didn't Want 😤
Overqualified and furious, Maha tells her dad the job is beneath her, and his response changes how she sees the whole opportunity.

13:30 - Turning a Job She Hated Into a Masterclass 📚
Maha explains how she mastered her boss's desk and calendar, and why she vowed to make everyone who walked past her remember her.

16:26 - "I Had to Deliver, Deliver, Deliver, Then I Could Ask" 💰
Maha gets candid about being paid a secretary's salary while executives around her had the big titles, and what it took to finally earn the raise.

18:30 - "What's the Worst That Could Happen?": The Cold Email to a Global PR Firm ✉️
She cold emails the chairman of Weber Shandwick, gets a no, and then gets a call back after September 11th.

19:35 - Where Real Confidence Comes From 💪
Maha explains how being thrown into the deep end, including writing the prospectus for the largest IPO in Egyptian history, taught her what she was capable of.

21:16 - "How Many Things Can Go Wrong for Me?" Her Father's ALS Diagnosis 💔
With her mother already ill, Maha learns her father has ALS and reflects on feeling devastated and far from her sister while building a career.

25:12 - The Midnight Airport Dash That Brought Her Home 🛫
She races to the Dubai airport with her dog, her housekeeper, and her suitcases just before the pandemic shuts everything down.

32:08 - "It Cost Me Never Having Children, But I Don't Regret It" ⚖️
Answering Maryam's question about what success has cost her, Maha talks about choosing to care for her parents over a family of her own.

33:54 - The Book That Changed How She Saw Herself 📖
Reading Gary Vee's “Crush It!” is the first time Maha realizes her work has been a career built on real skills, which leads her to seek him out.

35:24 - "It's Tattooed on My Back Shoulder" — Why She Has No Regrets ✨
Maha shares her best advice for people in their 30s and in the middle of a pivot, and reveals her "no regrets" motto is permanently inked in Arabic.

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"If your goal is to feel completed by success, it's gonna get worse and worse the more successful you get." Comedian and former SNL writer Rosebud Baker joins Maryam for a conversation that goes everywhere — sobriety, motherhood after IVF and miscarriage, growing up the granddaughter of Secretary of State James Baker, and a surprise divorce announcement that even Maryam wasn't expecting. Rosebud talks candidly about learning to operate outside of chaos, what burnout actually feels like once you've hit the goals you thought you wanted, and why she left SNL to build something of her own. Funny, raw, and full of hard-earned advice — including her take on your 30s ("it's your 20s but with more money") — this is a conversation about what's actually on the other side of ambition. Her memoir, "Fully Baked," is out now.

Key Moments

03:38 - "I've Always Operated Well in Chaos" 🌪️
Rosebud explains why calm, happy moments make her spiral while chaos has always felt like home.

05:09 - Tying Shoes Like She's Defusing a Bomb 💣
Rosebud describes the unbelievable adrenaline her body produces for everyday tasks, like getting her daughter out the door.

06:19 - Easter Eggs at the White House 🥚
Rosebud opens up about her grandfather James Baker, Secretary of State, and the unspoken rules of a political dynasty childhood.

08:46 - "That Was the Greatest Night of My Life" 🍸
Rosebud remembers throwing up in the backyard after her first drink and feeling, for once, like the main character.

15:23 - Saying "I'm an Alcoholic" Out Loud 🪞
Rosebud walks through the morning she finally told the truth to herself, then to a stranger, for the first time.

20:52 - IVF, Miscarriages, and Becoming a Mom 🤱
Rosebud gets candid about the road to motherhood and the responsibility that came crashing in the moment it became real.

25:29 - "That's a Lie That's Never Gonna Happen" 💭
Rosebud unpacks why chasing the pinnacle to feel complete only leaves you lonelier the more successful you get.

26:42 - Clinical Burnout, and Learning to Actually Relax 🔥
Rosebud describes hitting "the most depleted" she's ever felt after landing every goal she thought she wanted.

32:42 - The SNL Packet That Changed Everything ✍️
Rosebud recounts the years-long, accidental path from stand-up sets to writing for Saturday Night Live.

36:47 - The Cliffhanger: Announcing Her Divorce Mid-Interview 💔
Rosebud reveals, for the first time publicly, that she and her husband are getting divorced.

39:30 - Her Advice for Your 30s: "Your 20s With More Money" 🥂
Rosebud shares blunt, funny wisdom for anyone in their 30s trying to figure it all out.

39:47 - "F*ck That Job": Advice for Anyone Who Just Got Laid Off 💥
Rosebud's unfiltered response to what to do when you lose your job or your gig.

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Jake Barton worked on the 9/11 Memorial Museum for 8 years. One photo still makes him cry: a young firefighter in the Brooklyn Battery Tunnel, headed toward the towers, in what turned out to be the last picture ever taken of him alive. Jake joins Maryam on the blue couch to talk about the radical choice at the heart of that museum: letting the people who ran out of the burning buildings speak for themselves instead of being spoken for. And about the messier parts of his own story — an outcast childhood, a mentor relationship that shattered after Jake's three-person firm beat him for the biggest commission in the country, and the identity crisis that led him to sell the company he'd spent two decades building. His wife's warning at the peak: "I don't think you'll have a heart attack, but you might have a stroke." It's a conversation about art, impact, and what happens when you finally admit that the thing you built isn't making you happy anymore.

Key Moments

01:30 - The 9/11 Memorial a Quarter-Century Later 🕰️
Jake looks back on what he understands now about the 9/11 Memorial that he didn't grasp while building it.

05:38 - Winning the 9/11 Museum in a Battle Against His Own Mentor 🥊
Jake explains how he beat his mentor Ralph Applebaum for the 9/11 Memorial project and what it cost their relationship.

06:38 - Why Jake Leave His Mentor's Firm 💡
The exact moment Jake realized his mentor didn't see where museums — and storytelling — were headed.

08:31 - The Photo That Was a Father's Last Image of His Son 😢
Jake recounts the emotional story behind a photo that connected a grieving family to their son's final moments.

13:13 - How Middle School Bullying Shaped Jake's Path to Theater 🎭
Jake opens up about being a loner in middle school and how theater became his way out.

14:06 - The "Complete Psychic Meltdown" That Made Him Quit Theater for Pre-Med at 22 🌀
Jake describes the identity crisis that pushed him from a dream Broadway job toward medical school.

16:18 - "Human Decision-Making Is More Emotional Than Cognitive" — Advice for Anyone Mid-Pivot 🧠
Jake's take on trusting your gut over your resume when you're figuring out what's next.

29:29 - "You Might Have a Stroke": His Wife's Warning About His Pace 🚨
Jake shares the moment his wife told him his stress levels were becoming a health risk.

31:54 - "People Who Build Things vs. People Who Run Things" 🏗️
Jake explains the philosophy that led him to sell the firm he built over 20 years.

40:38 - What to Do Before You Turn 35 🎒
Jake's rapid-fire advice: take a real break, even a short one, and go all the way off into another world.

40:54 - His #1 Piece of Advice for Anyone Job Hunting Right Now 🔑
Jake's blunt take on how to build traction experience when you're starting out or starting over.

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He ran Southern Living and top Time Inc. titles with no college degree — then got fired, and calls it a gift. What followed was darker: broke, aged out of media at 50, and homeless. Ron King, now known as "Donkey King," rebuilt his life running a sanctuary that rescues donkeys from slaughter — 220 of them and counting. In this episode of The Messy Parts, Ron opens up to Maryam about hitting rock bottom twice, the hustle that built (and rebuilt) his career, and the simple mindset shift — "things could always be worse" — that carried him through it. A wild, honest conversation about reinvention, gratitude, and starting over at any age.

Key Moments:

00:00:00 - "Homeless at 50 — And It Was Worse Than 26" 😔
Ron opens on his lowest moment: sitting in his car on Mulholland Drive with no job, no savings, and no plan.

00:04:16 - "I Charmed My Way In. I Never Even Read a Magazine." 💫
Ron explains how he landed his first publishing job at 32 with no industry experience and no college degree.

00:07:48 - "I Didn't Lie. I Just Never Graduated." 🎓
Ron recounts confessing to his CEO that he flunked out of college and getting promoted anyway.

00:08:47 - The Diamond Earring That Landed the Impossible Meeting 💎
How Ron got a notoriously unreachable Estée Lauder exec to give him 15 minutes and a beauty section deal.

00:09:24 - Fired at the Top — "It Was a Gift" 🎁
Ron describes getting pushed out of Time Inc. and smiling all the way home.

00:13:01 - "I'd Aged Out. I Was an Old, Print, White Guy." ⏳
Ron on the moment he realized age — not talent — was closing doors after his fall from the top.

00:14:45 - Rock Bottom, Round Two 🚗
Losing his apartment, his car, and nearly his will to keep going at 50, with nowhere left to fall back on.

00:16:13 - "Put One Foot in Front of the Other" 🦶
Ron's advice for anyone in a crisis of confidence: sometimes surviving the day is the whole plan.

00:19:18 - A Random TikTok Video Changed Everything 🐴
How a video about a donkey auction became the spark for Oscar's Place.

00:25:05 - "I Decide Who Lives and Who Goes to Slaughter" 💔
The hardest part of running a donkey rescue: choosing which animals he can afford to save.

00:34:09 - "Things Could Be So Much Worse" 🙏
Ron's tactical approach to gratitude and why he thinks about everything that isn't going wrong.

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Jeff Jones spent his career as one of the most respected CMOs in America — Coca-Cola, Gap, Target — before making the leap to run Uber's global ride-sharing business under founder Travis Kalanick. Seven months later, at the height of Uber's pre-IPO valuation, he walked away from it all: no job lined up, no stock, no plan. On this episode of The Messy Parts, Jeff sits down with Maryam on the blue couch for his first real interview about what actually happened inside Uber during one of its most chaotic and scandal-plagued years. He also opens up about growing up in West Virginia, attending military school, becoming CEO of H&R Block, and what success really cost him — in family time, health, and friendships. This is a conversation about knowing the value of your own values, and having the courage to walk away at the top of your game.

Key Moments

00:00:00 - "Travis Was on the Cover of Every Magazine in the World" 🌍
Jeff opens with the moment he walked away from Uber's presidency less than a year after taking the job.

00:02:46 - Target Fame: Strangers Pitching His Wife in Parking Lots 🎯
Jeff recalls the surreal side of becoming Target's third-ever CMO and the scrutiny that came with it.

00:07:10 - From a 42-Kid Graduating Class to Military School 🪖
The coach's offhand comment that sent Jeff to Fork Union Military Academy and changed the trajectory of his life.

00:14:41 - Susan Fowler, Delete Uber, and a Waymo IP Scandal ⚠️
Jeff lists the crises unfolding behind the scenes at Uber that hadn't yet gone public.

00:19:20 - The New York Times Story That Made Him Quit 📰
Jeff learns about the grayballing investigation while flying home, and tells Travis in person that he's leaving — the next day.

00:25:34 - "You Can't Play Defense With Your Career" 💼
His advice for anyone navigating a layoff, pivot, or professional reinvention.

00:35:34 - What Success Actually Cost Him 💔
Jeff gets candid about the toll eight years as CEO took on his family, his health, and his friendships.

00:39:25 - "Just Jeff" — Life After the Title 🎧
How Jeff wants to be introduced now that "CEO" is no longer part of his name.

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Fired at 24. Turned down her dream job at Nike, then took it anyway. Walked into HSN as the eighth CEO in ten years. Mindy Grossman built one of the least likely careers in American business, and in this episode of The Messy Parts she tells Maryam how: leaving college at 19 to move to New York with $1,800, landing her first job by admitting she couldn't take shorthand, buying 2,000 Aeron chairs to prove a broken culture was changing, and converting 30,000 Weight Watchers meetings to virtual in six days at the start of COVID. Plus the one question about her daughter she still can't answer.

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Key Moments

00:00 - "Here's What Success Cost Me" 💭
Mindy opens up on whether all she's achieved came with a personal price.

02:18 - "My CEO Journey Started When I Was Three Days Old" 👶
Mindy traces her drive back to the story of her adoption and parents who raised her to believe anything was possible.

07:07 - "I'm Breaking My Engagement, I'm Not Going to Law School" ☎️
At 19, Mindy makes the phone call to her parents that redirects the entire course of her life.

13:37 - "That Woman at the Front Desk—I Want Her to Work for Me" 👀
A designer notices Mindy filling in as a receptionist and gets her promoted before she even knows it happened.

16:18 - "I Need to Thank You for Firing Me" 🏈
Years after getting fired at 24, Mindy runs into her old boss at the Super Bowl and flips the story on its head.

24:00 - "I'm Going to Employee Orientation" 🎬
On day one as HSN's new CEO, Mindy skips the executive playbook and shows up where the real culture lives.

27:41 - "2,000 Aeron Chairs, Delivered the Same Day" 🪑
Mindy explains the small, symbolic move that told an entire company she cared.

29:39 - "That Is Fascinating" 📺
Mindy sees on CNBC that Oprah has joined Weight Watchers—and a new pivot starts taking shape.

30:09 - "It Was Not Easy for Her, and Not Easy for Me" 👩‍👧
Mindy gets candid about the toll her career took on her relationship with her daughter.

34:11 - "We Converted Every Meeting to Virtual in Six Days" 🦠
As COVID shuts everything down, Mindy and her team race to keep the Weight Watchers community intact.

38:23 - "I Have to Be a Lot Better at Self-Care" 🧘‍♀️
Asked what her body knows that her résumé doesn't show, Mindy admits the one thing she's still working on.

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Behind every legendary career is an unfiltered human truth. In this special compilation, 20 of our most notable guests—including Mickey Drexler, Samantha Bee, Blake Mycoskie, Bonnie Hammer, Kim Hastreiter, Sally Susman, Sari Botton, and Baked by Melissa—reveal what happens when the PR guardrails come down. From Bevy Smith’s show-stopping mandate to "have sex, a lot of it," to surprisingly vulnerable confessions about daily tears, imposter syndrome, and surviving a crisis of confidence, these bite-sized moments cut straight to the heart. Equal parts entertaining, profound, and deeply validating, this episode proves that even industry pioneers, Pulitzer winners, and cultural icons are navigating life's inevitable mess.

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Brian Kelly (aka The Points Guy) has been obsessed with credit card and frequent flyer points since childhood. At age 12, his dad challenged him to book a family vacation using only points, and young Brian successfully got his entire family to the Cayman Islands for free. In this episode, Brian tells Maryam about the reality behind his meteoric rise: ruined credit, toxic friendships, launching The Points Guy as a side hustle, becoming a multi-millionaire at 28 years old - and the loneliness that followed. He shares hard-won lessons about leveraging relationships, knowing your superpowers, and why most career decisions aren't actually binary. This is the unvarnished truth about building an empire from nothing.

Key Moments:

00:00 - "$28 Million for a Blog" 🤯
The surreal negotiation that turned a $10 domain into a life-changing payday — and the mind games that came with it.

02:12 - "The Points Kid": Growing Up With a Businessman Dad 🧳
Brian traces his origin story back to childhood and family trips funded by his dad's frequent flyer miles.

04:20 - Booking the Family's First Free Trip at 12 👦
After charging his dad $10 a booking, young Brian figures out the miles, how to fly the whole family to the Cayman Islands - for free!

11:54 - Wage Garnishment and a Payday Loan in SoHo 💸
Brian gets brutally honest about being flat broke in his first NYC job: bad credit, creditor calls, and a boss pulling him aside about unwashed suits.

17:11 - The Frugal Travel Guy Lets Him In on the Secret 🤫
A 65-year-old blogger pulls Brian into a side room at a conference to reveal the affiliate-marketing trick that would change everything.

19:27 - A Jealous Colleague Tries to Get Him Fired 😬
Brian recounts a coworker reporting him to HR out of envy and how one senior mentor quietly saved his job.

22:26 - The NYT Article, the Shower Epiphany, and "I'm Pretty Sure I'm Rich" 🚿
A viral credit card offer and a New York Times feature collide, and Brian realizes in real time that his site just made him six figures in a day.

26:39 - Selling The Points Guy for $28 Million at 28 💰
Brian breaks down the whirlwind negotiation and earn-out that turned his blog into a life-altering payday.

29:07 - Betrayed by a Friend Over Money 🏚️
After the sale, Brian describes friends turning on him and a trusted interior-designer friend secretly pocketing money meant for his apartment.

33:59 - "2020 Was the Best Thing That Could Have Happened to Me" 🛑
Brian admits he was on a collision course with burnout as CEO, until the pandemic forced him to step back and rethink everything.

37:53 - Rapid Fire: Advice for Before You Turn 35 ⏰
Brian fires off quick hits: take a great solo trip, never push yourself to exhaustion again, and stop asking for permission to try new things.

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"I don't believe in burnout." That's Laura Mayer, podcast industry veteran and author of Tryhard, explaining why she's never really taken a break: not after a complicated pregnancy, not after quitting a stable executive job at ABC News, not ever. In this candid conversation with Maryam, Laura traces her try-hard tendencies back to a childhood spent tracking her mother's alcoholism, unpacks the false choice between "lean in" hustle and burnout culture, and explains why she walked away from a secure media career to be more present for her daughter. It's a funny, unflinching look at ambition, identity, and the stories we tell ourselves about why we work the way we do.

Key Moments

00:00 - "That's Not the Answer" 😤
Laura calls out how meaningless the word "burnout" has become when people use it as an excuse and then do nothing about it.

02:06 - The McMansion, the Girl Scouts, and the Alcoholic Mom 🏡
Laura paints a picture of her idyllic-looking Chicago suburb childhood, and the reality of a mother who was "present, but not there."

03:36 - The Chart: Tracking Mom's Drinking on the Hurricane Scale 🌀
Laura reveals the five-point system she built as a kid — based on the Saffir-Simpson hurricane scale — to predict her mother's moods.

05:14 - Leaning In, Hard 📘
Maryam brings up Sheryl Sandberg's “Lean In” and Laura admits she read it, believed it, and leaned in harder than almost anyone.

11:08 - Front Row for the Podcast Industry's Big Bang 🎙️
Laura describes being inside WNYC as “Serial” exploded and Gimlet Media launched, kicking off podcasting's first gold rush.

16:16 - "Have You Ever Taken a Pause?" 🏥
Laura's answer: basically no — except one hospital stay, which she jokes might be the only "forced medical vacation" she's had.

17:34 - The Failed Loom and the Two Weeks in Crocs 🧶
After leaving a high-paying media job with a new baby, Laura tries and fails to take an actual break.

21:08 - "I Really Truly Almost Died After I Had My Kid" 🚨
Laura and Maryam swap near-death postpartum stories, and Laura explains how hers cracked open a permission to finally be creative.

22:49 - Breaking the Podcast Industry's Money Omertà 💰
Laura details the economics of the podcast-to-TV option pipeline, numbers she says the industry has a habit of not discussing out loud.

28:08 - Quitting ABC News for Her Daughter 👋
After quadrupling ABC's true crime output, Laura walks away from the stable, high-status job she once dreamed of to be home more.

32:44 - Rapid Fire: Advice for Before You Turn 35 ⏰
Laura fires off her list fast: start your retirement account, wear sunscreen, fix your sleep hygiene, set your meeting alerts 15 minutes early, and don't trust anyone who tells you "it'll be all right."

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"Even your dream job sucks." That's not cynicism — it's the most useful career advice Samantha Bee has. On this episode of The Messy Parts, she tells Maryam what 12 years at “The Daily Show” and running “Full Frontal” actually taught her: that no one hands you management training before you're leading 75 people, that public setbacks feel enormous and matter less than you think, and that the comparison game — "looking in other people's food bowls" — is where careers go to stall. Her rule for anyone under 35: stop worrying what people think of you, because they're too busy worrying about themselves. What's the "dream job" lesson you had to learn the hard way?

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Show Notes:

00:00 - "Every Part of It Was Messy" 💥
Samantha Bee kicks off with a raw reality check about landing The Daily Show: even when you’re living out everyone else’s dream, the work can still suck a lot.

03:11 - "Fearlessness Born from Blind Ignorance" 🎭
Sam recalls trying a theater class just for an "easy A" and discovering that total ignorance gave her the weird confidence to get up on stage while everyone else was throwing up.

04:12 - "You Have to Do the Thing You Like... Just a Little Bit" 🧩
Sam breaks down her go-to career advice for her kids: finding that tiny kernel of joy in what you do, even when there's no plan B and the path makes zero sense.

09:14 - "F*ck Acting, Acting Sucks" 🎬
Sam shares how letting go of corporate approval and putting on sketch shows with friends actually saved her career.

12:21 - "Stop Looking in Other People's Food Bowls" 🥣
A practical masterclass on resisting the urge to compare your career trajectory to everyone else's, especially when navigating a sudden pivot or loss of stability.

15:21 - "Forged in a Fire at The Daily Show" 🌋
Reflecting on 12 years with Jon Stewart, Sam talks about the brutal schedules, looking terrible on camera, and why working with genius minds makes the suffering worth it.

19:23 - "I Didn't Go to Business School" 👔
Sam admits her complete failure at managing a team of 75 people when starting Full Frontal, learning the hard way that you can't be everyone's best friend in business.

21:15 - "I Pushed the Doubts Out Like the Kool-Aid Man" 🍹
A hilarious and honest trick Sam learned for dealing with soul-crushing self-doubt: physically shoving negative thoughts out of your brain and barging forward anyway.

27:32 - "When Is Enough Actually Enough?" 🛑
Sam rails against modern hustle culture and endless greed, reflecting on why so many successful people struggle to appreciate what they have and pay it forward.

36:33 - "No One Is Thinking About You That Much" 🧘‍♀️
Sam drops her ultimate piece of advice for anyone under 35: stop worrying about what others think of you because everyone is way too busy obsessing over themselves.

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She dug through filthy sub-basements in the Bowery looking for discarded restaurant ware — and built one of New York's most beloved stores. Julie Gaines, co-founder of Fishs Eddy, joins Maryam on the blue couch to talk about 40 years of messy parts: the husband who cheated and left for Florida (then Thailand), the three CEOs who didn't work out, and the MS diagnosis she now calls a "dignity thief." Julie doesn't sugarcoat any of it. She's blunt, she's funny, and she's still working through it all. If you've ever wondered what it actually takes to survive four decades in business and life, this one's for you.

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00:00 - "Talk About a Messy Part You Have No Control Over" 🦽
Julie opens with a cold, honest gut-punch about her MS diagnosis and the slow shift from cane to walker to wheelchair, setting the tone for an episode that doesn't flinch.

02:41 - How Julie Met Dave and Found Her Store 💘
A chance walk down a West Village street, a movie date, and a shared obsession with funky glassware. Julie recounts the meet-cute that would eventually become Fishs Eddy.

04:48 - Digging Through Bowery Basements for Treasure 🕯️
Julie describes the filthy, dimly lit sub-basements packed with abandoned restaurant ware where she and Dave built the foundation of their business.

09:50 - "It Just Felt Like Opportunity" — '80s New York Nostalgia 🗽
Julie reflects on the grittier, more affordable New York she came up in, and how different that landscape feels from the city today.

14:41 - "What Do I Have to Lose?" The Cynthia Rowley & Caroline Kennedy Collabs 📞
Julie explains her fearless, cold-outreach philosophy that landed her collaborations and a memorably awkward first call with Caroline Kennedy.

19:14 - Three CEOs and the Problem With "We're All Family" 👨‍👩‍👧‍👦
Julie gets candid about burning through outside hires because she and Dave couldn't stop treating employees like family, even the ones who didn't deserve it.

23:07 - Her Daughter's Phone Reveals the Affair 💔
Julie recounts the exact moment her daughter showed her the texts that ended her 30-year marriage, and the phone call to Dave that confirmed it was over.

25:22 - "He Clipped My Wings" ✂️
Her son's blunt assessment of what Julie’s marriage had cost her, and how those words still stick with her today.

29:59 - "I Was Devastated" — the MS Diagnosis 🩺
Julie walks through the early days of her MS diagnosis, the doctor's chilling advice to "go home and enjoy your family," and how the disease has progressed since.

32:21 - Why Julie Shares Her Messy Parts So Openly 🎤
Julie explains why she refuses to hide her MS the way so many women do at work, and how humor has become her survival tool.

40:17 - Julian Schnabel Turned Her Dishes Into Art 🎨
Julie tells the story of a customer who bought bushels of Fishs Eddy dishes to smash and use in his paintings — only to later learn he was renowned artist Julian Schnabel.

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"They cut me from that team." That's how Columbia women's basketball head coach Megan Griffith opens this episode of The Messy Parts — and it's just the beginning of her story. Megan tells Maryam about growing up a Chinese American kid in a homogeneous Pennsylvania suburb, playing for four different coaches in four years as a student at Columbia, and deciding to pursue a professional basketball career across Finland, Sweden, and the Netherlands. Megan gets candid about identity, belonging, getting benched by life more than once, and the leadership lessons she now hands down to her players as Columbia's most successful women’s basketball coach in program history. It's a conversation about turning setbacks into strategy — on and off the court.
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Key Moments

00:00 - "They Cut Me From That Team" 🏀
Megan opens with the gut-punch story of getting cut from her professional team in Sweden — the moment that set off a chain reaction leading her all the way back to Columbia.

01:15 - Growing Up Between Two Worlds 🌏
Megan reflects on growing up in a mostly white suburb of King of Prussia, PA, with a mother from Hong Kong, and how she and her sister came into their Asian American identity later in life.

04:56 - The Recruiting Fluke That Brought Her to Columbia 🎓
Megan explains how a chance connection — not a big recruiting push — landed her at Columbia.

07:22 - Four Head Coaches in Four Years 👕
Megan recalls playing for a program with no brand, no real uniforms, and constant coaching turnover — and the leadership lesson she took from staying loyal through the chaos.

10:25 - The Pencil Skirt That Didn't Fit 💼
Megan describes trying out corporate finance after graduating, and the exact moment she knew it wasn't for her.

12:14 - The Conversation That Changed Everything ✈️
A friend's offhand suggestion to "keep playing" sends Megan overseas to Finland — and into a professional career she never planned for.

16:51 - From Cut Player to Coach 🔑
After coming home from playing abroad, Megan stumbles into coaching almost by accident — and gets told point-blank that "no Ivy League alums coach."

20:27 - Taking the Job Everyone Called "Messy" 📋
Megan explains why she almost didn't take the Columbia head coaching job, and what made her finally go all in on a program everyone else saw as a lost cause.

23:14 - The Recruiting Pitch That Rebuilt the Program 🌟
Megan breaks down her strategy for recruiting talent Columbia had never landed before — including two future WNBA draft picks other programs passed on.

30:43 - The NCAA Snub She Refused to Stay Quiet About 📢
Megan tells the story of being excluded from the NCAA tournament, handed a script for her next press conference, and choosing to advocate loudly for her team — even if it meant blowback.

37:44 - "Feedback Is Food, Failure Is Fertilizer" 🌱
Megan shares the philosophy that drives her coaching, plus her advice on setting boundaries, owning your decisions, and what success actually costs.

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What really happens after a founder sells their company? Blake Mycoskie built one of the most recognized brands in the world at TOMS — and hit rock bottom the moment he walked away. In this episode of The Messy Parts, Blake talks candidly with Maryam about founder identity, the mental health crisis hiding behind big exits, and why more money and more success never made him feel like enough. He also shares the advice he'd give every founder in their 20s and 30s, what Ted Turner told him before he made his first billion, and how healing his "core wound" changed his relationships, his parenting, and the way he builds companies today.
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Key Moments

02:15 - Why Blake Broke His 3.5-Year Social Media Silence 📱
After years of suffering quietly and feeling ashamed, Blake explains what finally pushed him to publish that vulnerable LinkedIn post.

6:24 - Naming the Core Wound 🔍
Blake identifies the belief that secretly drove every business he ever built: that he was never enough, and that the only way to earn love was to keep proving himself.

10:18 - How TOMS Was Really Born 👟
Blake tells the origin story — a simple idea hatched in Argentina, started out of his Venice Beach apartment with no investors and no business plan, that grew into a huge movement.

12:24 - The Night He Got a Nelson Mandela Award and Felt Terrible 🏆
One of the most striking moments in the episode: Blake describes receiving one of the biggest honors of his career and calling it one of the worst nights of his life.

15:20 - What Blake Would Tell Every Founder Before a Big Exit 💡
Hard-won advice: make sure you have something meaningful to pour your energy into on the other side — because the dopamine drop is real, and snowboarding only lasts so long.

21:45 - What Depression Actually Feels Like 🌊
Blake offers one of the most accessible descriptions of depression you'll hear: like really bad jet lag — knowing you should be awake, but being unable to move.

26:39 - What Ted Turner Told Blake Before He Made His First Billion 🏔️
In a private green room moment at the UN, Ted Turner warned Blake that when he reached the top of the mountain, the chest would be empty.

29:25 - How Healing Changed His Relationship With His Kids 👨‍👧‍👦
Blake reflects on a painful realization: that for years, his own "not enough" wound was being projected silently onto his children.

36:45 - The Advice He'd Give His 30-Something Self 🎯
Blake's closing wisdom: do something you genuinely love in your 20s and 30s, because true financial freedom almost always follows mastery — not the other way around.

37:32 - The Send-Off 💛
Maryam closes with three words that land differently after everything Blake has shared: "You are enough."

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She's a staff writer at The New York Times Magazine, a Yale lecturer, and one of the most celebrated journalists working today. So why does Susan Dominus still feel like she's figuring it out? In a candid conversation with Maryam, Susan gets into the imposter syndrome that nearly stopped her from calling herself a writer, the sibling rivalry that quietly shaped her ambition, and the career regret she wishes she could go back and fix. Plus: what AI has changed about her reporting, why she thinks Substack isn't enough, and the advice she gives every student who wants to break into media. If you've ever played it safe when you knew you shouldn't have — this one's for you.
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Key Moments

01:28 - The Psychology Behind the Byline 🧠
Susan explains why people tell journalists things they've never told anyone else, and why being truly seen is rarer than we think.

03:15 - The Bookish Kid Who Pretended to Read 📚
Susan paints a vivid picture of her Westchester childhood — the youngest of three, already pretending to read before she could, and processing her entire emotional life through books.

09:29 - The Piano Teacher Ultimatum ⏰
Her piano teacher forced a choice: piano or the school newspaper. Susan didn't hesitate for a second.

13:07 - Imposter Syndrome at Yale 😰
Getting into Yale didn't cure the self-doubt — it deepened it. Susan opens up about feeling like a "pretty average suburban kid" surrounded by legacy admits, children of academics, and people she found genuinely intimidating.

14:25 - "I Couldn't Risk It" 😶
Susan admits she avoided Yale's competitive writing classes entirely, not because she wasn't interested, but because she was too afraid to find out she wasn't good enough.

21:13 - The Good Girl Who Waited Until 30 ⏳
Despite always wanting to be a writer, Susan spent her entire 20s as an editor — partly for job security, partly to please her parents.

27:08 - How AI Changed Susan's Entire Reporting Process 🤖
Susan goes from AI skeptic to convert in real time. She breaks down exactly how she used NotebookLM and Google Gemini on her most recent NYT piece, and why she can't imagine going back to the way she did her job before.

30:17 - The Wasserstein Book Origin Story 📖
Susan traces her obsession with the famous Wasserstein family, and reveals the question that consumed her childhood: what would it feel like to grow up in a family where someone tells you "the sky's the limit"?

33:42 - The Limits We Put on Ourselves 🪞
Maryam holds up a mirror: Susan has won Pulitzers, teaches at Yale, and writes for the NYT Magazine — and yet she still talks about herself like someone playing it safe.

40:24 - The Twitter Regret She Can't Shake 🐦
Susan confesses that when the NYT begged her to tweet out her column back in 2011, she was too uncomfortable with self-promotion. Her advice to young journalists: get on the edge of what's new, even when it scares you.

43:11 - What She’d Tell Her 30-Something Self 💡
Susan closes with a deceptively simple piece of wisdom: if something new is forming around you at work, stop wishing it away and get involved.

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In this re-release of one of our favorite episodes, Gary Vaynerchuk opens up to Maryam about fear, self-esteem, forgiveness, AI, leadership, and what he believes is a growing crisis of “late adulthood.” Gary shares why so many professionals feel stuck — not because of burnout, but because of insecurity and unresolved resentment. He breaks down his philosophy on kind candor vs. radical candor, why fear is the real career killer, and how over-coddling may be delaying independence for an entire generation. From parenting teenagers to leading thousands of employees, Gary explains why self-worth is the operating system behind success — and why forgiveness (especially of yourself) might be the most underrated personal development tool of all. If you’ve ever felt behind, afraid to pivot, or unsure of your next move in the age of AI, this episode is for you.

Key Moments

00:00 — Forgiveness Is the Answer We’re Avoiding ❤️‍🩹
Gary opens with a bold claim: most people are emotionally “clogged” because they’re holding resentment. He explains why forgiveness — especially forgiving yourself — may be the most underrated growth tool.

02:46 — “Nice Guys Finish First” 🏆
Gary unpacks the tension between competitiveness and kindness — and why he believes you can be fierce in business without losing your humanity.

05:17 — The Late Adulthood Crisis 🚨
Are we raising adults who aren’t ready to be adults? Gary shares his controversial take on over-coddling, privilege, and why independence matters more than ever.

08:52 — Why He Doesn’t Fear AI (And You Shouldn’t Either) 🤖
Using historical pattern recognition, Gary explains why AI is just the next evolution — not the apocalypse.

14:18 — The Self-Esteem Conversation Nobody Wants to Have 🧠
Gary breaks it down: almost everything — career fear, content paralysis, insecurity — comes back to self-worth.

15:33 — The Rejection He Was Actually Afraid Of 💔
Despite fearless business moves, Gary admits he was afraid to ask girls out in high school. A revealing look at how fear shows up in unexpected places.

18:38 — Kind Candor vs. Radical Candor 🎯
Gary shares his leadership “kryptonite” — struggling with candor — and why he now believes honest feedback must come with kindness.

28:57 — Walking Away From the Family Business 🏪
After building his dad’s liquor store into a $65M company, Gary explains why leaving wasn’t guilt — it was growth.

31:14 — Maximizing Joy vs. Maximizing Money 🔥
Why Gary doesn’t optimize for profit alone — and how curiosity drives his many ventures.

33:35 — Call Your Mom. Forgive Yourself. 📞
One of the most emotional moments of the episode. Gary urges listeners to make the call — to forgive others or themselves.

43:53 — At What Age Do You Stop Blaming Your Parents? 🧨
Gary poses a provocative question: when do you fully own your life? A raw discussion about responsibility and adulthood.

47:46 — The Jets Jersey Story 🧵💚
Gary shares the powerful story of his mom knitting him a Jets jersey when they couldn’t afford one — and how that shaped his confidence forever.

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What happens when you walk away from the career everyone expected you to have? Chef Ayesha Nurdjaja was on a path toward law school, working at a prestigious law firm and doing everything “right.” But something was missing. In this episode of The Messy Parts, Ayesha shares with Maryam how she left a promising legal career to pursue cooking, even when her parents stopped speaking to her and everyone around her thought she was making a huge mistake. She opens up about growing up in Brooklyn, discovering her passion for food later in life, working brutal restaurant hours for almost no money, and refusing to accept “no” as an answer. Ayesha also reveals the surprising story behind the creation of Shuka and Shukette, and how one bold decision changed the course of her career.
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00:00 - The Lie That Launched Her Career 🚪
Ayesha tells the unbelievable story of sneaking her way into Lidia Bastianich’s legendary restaurant kitchen after being repeatedly told no, and how that gamble changed her life forever.

03:40 - Growing Up Between Two Worlds 🌎
Ayesha reflects on her Brooklyn childhood, her Italian and Indonesian roots, and how family, culture, and belonging shaped who she became.

07:26 - When Religion Tore Her Family Apart 💔
She opens up about her parents’ divorce, the cultural and religious tensions behind it, and the lasting impact it had on her life.

11:06 - The Career Everyone Wanted for Her 🎓
From pharmacy school to business school to a law firm job, Ayesha shares the path her parents hoped she’d follow, and why it never felt right.

16:24 - The Bucket List That Changed Everything ✍️
A train ride, a list of passions, and a moment of honesty helped Ayesha realize she was chasing the wrong dream.

18:26 - Diamonds, DJing & Finding Her Calling 💎
Before becoming a chef, Ayesha seriously considered careers in music and diamonds—and explains how cooking unexpectedly won.

20:21 - The First Dish That Sparked Something Special 🍅
A simple risotto-stuffed tomato became the moment Ayesha discovered the joy of creating food with her own hands.

21:26 - The Day Her Parents Stopped Speaking to Her 📵
After quitting a stable legal career to work in kitchens for almost no money, Ayesha faced the toughest rejection of all — from her own family, who struggled to understand her radical pivot.

25:37 - Why She Never Quit the Kitchen 🔥
Ayesha explains the relentless drive that pushed her through 16-hour days, exhausting labor, and years of sacrifice.

39:33 - The New Year's Eve Party That Created Shuka 🎉
What started as a risky, Moroccan-inspired dinner party became the spark that led to one of New York City's most beloved restaurants.

41:22 - Betting on Yourself Every Time 🎲
Ayesha reflects on risk-taking, resilience, and why she's always been willing to go all-in on the things she truly believes in.

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"No just means not right now." That's the philosophy that kept writer and Oldster founder Sari Botton going through decades of rejection before building one of Substack's most beloved magazines — at age 60. In this episode of The Messy Parts, Sari gets honest with Maryam about the messy middle: the identity searching, the failed attempts, the mean girls that never quite went away, and the moment she finally stopped contorting herself to fit someone else's story. She also shares the writing strategies that got her through a book deal she almost abandoned, and why she thinks the busier you are, the better you write. If you're a writer, a late bloomer, or just someone still figuring it out — this conversation is for you.
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Key Moments

00:00 - "No Just Means Not Right Now" 💪
Sari opens with the mantra that kept her going through decades of rejection, and explains why she refuses to take no for a final answer.

00:53 - Meet Sari Botton 📖
Maryam introduces the writer, publisher, and Oldster founder whose New York Times feature sent her Substack into the stratosphere.

03:35 - The Hustler's Origin Story 👊
Sari traces her work ethic back to her parents, and how watching them juggle everything shaped who she became.

06:28 - The Creative Weirdo Who Never Fit the Mold 🎭
Sari reflects on growing up as a dreamy, performing kid who started writing plays at seven.

08:02 - "Since My Late Forties, I've Been Becoming Who I Really Am" ✨
Sari gets candid about the long road to self-certainty, and why it took decades of peeling away inauthentic layers to finally arrive at herself.

10:58 - The Secret She Was Keeping From Herself 🤫
Sari reveals she never actually wanted children — and the surprising relief she felt when a medical diagnosis made the decision for her.

13:02 - Mean Girls Never Really Go Away 😤
Maryam and Sari dig into the culture of indirect honesty, female friendship, and why being direct is still so hard — even at 60.

21:35 - "The Most Sustainable Situation I've Ever Had" 🙌
Sari reflects on arriving — finally — at a creative life that actually pays, and what it means to build something that works on your own terms.

23:32 - Trusting Your Instincts When Everyone Says No 🔥
Editors and agents said her anthology ideas would never sell — but Sari she did them anyway. Now she has 85,000 Oldster subscribers and counting.

26:24 - On Finding Success Later in Life 🌟
Sari gets emotional about what it means to finally be living proof that good things can happen at any age.

29:42 - The Memoir She Almost Abandoned 📝
Sari opens up about her 3am anxiety spirals while writing her memoir, the Pomodoro method that saved her, and why the first draft just needs to exist.

35:07 - Rapid Fire: Messy Moments, Confidence Crises & Walk-On Songs 🎤
Sari's messiest moment, her advice for anyone in a confidence crisis, and the song that gave her the courage to write her memoir.

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