At 22, Jaclyn Johnson landed her dream magazine job — until she realized it paid less than her rent. That rejection set off a chain of bold decisions: launching a fashion blog, being sued by a former employer, losing a job she moved across the country to take, and eventually starting her own PR/branding agency. Jaclyn tells Maryam how she turned fear into fuel and turned Create & Cultivate from a side hustle into a brand she eventually sold for $22 million. 

Along the way, she learned what women aren’t taught and don’t discuss in business, why women sometimes don’t support one another professionally, and the magic that can happen when they do. Jaclyn doesn’t sugarcoat the toll success can take — panic attacks, burnout, isolation — but she also shows how failure, when faced head-on, can be the greatest creative act of all.

Key Moments

*  “You can’t eat makeup.” Learn why saying no to underpayment was the first bold move that shaped Jaclyn's multi-million-dollar career. 

* If you want to run your own business, you need to understand every role first. An early magazine internship taught Jaclyn Johnson a lesson most entrepreneurs miss: sales runs the show. She realized editorial might look glamorous, but it’s marketing and revenue that keep the lights on — and that knowing how every piece fits together is what makes a great founder. 

* Her advice for anyone just starting out: believe in yourself enough to show up. You might not be the expert today, but you can be tomorrow. Confidence comes from action, not perfection.

* Being the Squeaky Wheel Can Get You Fired — And Set You Free. Jaclyn Johnson shares how being the one who questions, challenges, and moves too fast ultimately got her fired… and turned out to be the best thing that could’ve happened. Her story is a reminder: sometimes getting fired just means you’re meant to be your own boss

* Jaclyn shares the turning point when Create & Cultivate went from side project to full-blown brand. After one breakout event, major clients started reaching out — and she realized the momentum was real. Encouraged by a mentor to bet on herself instead of building for others, Jaclyn took the leap and never looked back

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Think your biggest breakdown means you’ve failed? Journalist Danielle Belton was hospitalized multiple times for bipolar disorder while she was building her career. In this powerful episode, she opens up to Maryam about a childhood riddled with anxiety, falling into a deep depression after a failed marriage, and drinking tequila at work to power through panic attacks. Danielle hit rock bottom in her mid-twenties and moved home to her parents basement, where she started over and got a job folding sweaters at Macy’s. She tells Maryam how writing an anonymous blog during Barack Obama’s first presidential campaign led to other jobs that ultimately landed her a dream gig — editor-in-chief at HuffPost — and why she eventually walked away from it. Determined to defy the mental illness stigma, Danielle promised herself she’d live publicly with her illness no matter what. A raw, honest conversation about mental health, ambition, and resilience for anyone who’s ever thought their worst moment ended their shot at success.

Key Moments

00:00 – Danielle shares her promise to be open about bipolar disorder to show others there’s life after diagnosis.

02:30 – She reflects on her anxious childhood, feeling old before her time and misunderstood by other kids.

10:00– Danielle opens up about leaving a toxic marriage and reclaiming her ambition.

11:30 – Danielle describes the physical ways her anxiety started to manifest

13:00 – A raw confession about masking panic attacks with alcohol during her early reporting career.

15:00 – The first of four hospitalizations for bipolar disorder — a turning point in accepting she needed help.

20:00 – After her breakdown, Danielle describes the humiliation of moving back to her parents’ house and starting over — but also the seed of her comeback.

22:30 – Her anonymous blog goes viral after Obama wins Iowa, launching her back into journalism.

25:00 – A doctor’s advice pushes her to balance ambition and self-care as she tiptoes back into the working world

33:00 – At The Root, Danielle battles depression but still rises to Managing Editor, proving high-functioning illness is complex.

36:00– Danielle explains why she left her job as Editor-in-Chief of HuffPost to protect her team.

40:30 –  Danielle’s closing advice: feel your pain, but don’t live there. Remember who you are, and gamble on yourself.

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What if everything you were told about building a career was wrong? Financial expert and host of The So Money Podcast, Farnoosh Torabi, gets raw about the messy reality behind her success—from being forced to give up her dream schools to avoid debt, to getting fired twice, to drowning in $300K of business debt that forced her to sell her home.

This isn't another "hustle harder" story. It's an honest conversation about the fears nobody admits: waiting for permission that never comes, taking rejection personally, feeling naked without a job title, watching friends with trust funds lap you, and chasing definitions of success that aren't even yours.

If you've ever felt paralyzed applying to hundreds of jobs, ashamed about a layoff, or terrified of financial dependence, this one's for you. We're talking about the career stuff nobody warns you about—and what actually helps when things fall apart.

You're not failing. The game just changed and nobody told you.

Show Notes: 

Guest: Farnoosh Torabi, a financial expert, bestselling author, and host of the "So Money" podcast and “The Montclair Pod.”

Learn More About Farnoosh: https://farnoosh.tv/

Follow Farnoosh on Instagram: https://www.instagram.com/farnooshtorabi

So Money Podcast: https://podcast.farnoosh.tv/

The Montclair Pod: https://podcasts.apple.com/us/podcast/the-montclair-pod/id1785567683

Topics Covered: 

• The Debt-Versus-Dreams Trap
• The Comparison Trap on Social Media
• The Paralysis of Permission-Seeking
• The Rejection-Is-Death Mindset
• The Job Application Black Hole
• The Financial Dependence Fear
• The "Shiny Object" Definition of Success
• The Layoff Shame Spiral
• Ending a Job Without Closure 
• Entrepreneurial Debt Disaster

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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.

Fast forward to his twenties, and his credit was ruined. He had to resort to payday loans. As he says, "I was in survival mode." He walked to work because he couldn't afford the subway fare. His boss had to give him a raise just so he could dry clean his suits. Kelly understood he needed to solve his problems, so he tried various side hustles to make ends meet.

One of those side hustles was starting a blog called The Points Guy. In a single day only a short time after he began the blog, Kelly made $125,000. Six months later, he hit his first million. Somehow, this hobby-turned-side-hustle had made him a multi-millionaire at 28 years old.

It was a challenging, messy road. In this discussion, Kelly reveals the reality behind his meteoric rise: the toxic friendships, the fraudulent interior designer who stole from him, and the loneliness that comes with sudden wealth. 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 Takeaways From This Episode

Identify Your Strengths and Double Down: When Brian realized he couldn't compete on analytics with Ivy League graduates, he focused on what he was best at - relationship building - which became his competitive advantage throughout his career.

From Financial Rock Bottom to Millions in Months: Brian went from taking payday loans and walking to work to making $125,000 in a single day through affiliate marketing - showing how quickly fortunes can change with the right strategy.

Turn Your Biggest Expense Into Income: Brian transformed his company's travel expenses into personal profit by volunteering to put all recruiting trips on his credit card, earning massive points while helping colleagues.

Side Hustles Can Scale Beyond Your Day Job: What started as a $500-1000/month blog became a million-dollar business in six months - Brian shows how to test ideas without quitting your main income source.

Leaving Jobs on Good Terms for Future Opportunities: The Points Guy stayed three extra months at Morgan Stanley to properly transition his responsibilities, maintaining relationships that served him throughout his career.

Research Hiring Managers, Not Just Job Requirements: Brian's interview success came from connecting personally with interviewers rather than just reciting qualifications - he'd research their backgrounds to find common ground.

Build Senior Mentors as Career Insurance: When a colleague tried to sabotage him, Kelly's senior mentor at Morgan Stanley protected his job - provin

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If you’re job hunting, eyeing a promotion, or just feeling burnt out—this conversation will remind you that your path doesn’t have to be traditional to be powerful. 

From bossy kid to bold career coach, Sam DeMase is redefining what leadership and success really look like—with empathy, authenticity, and purpose. 

In this episode, Sam shares her unconventional journey: from managing 70 people at a fast food chain straight out of NYU to building a business that empowers women to ask for more—more money, more respect, and more balance.

Shaped by her experiences with toxic bosses, anxiety, and corporate pushback, Sam empowers others to navigate their careers with confidence, clarity, and self-trust.

We dive into bridging generational gaps, debunking myths about Gen Z, and why empathy is essential in today’s workplace. Sam introduces “parallel pivoting,” the power of side hustles, and how to turn nontraditional paths into professional superpowers.

Show Notes: 

Guest: Sam DeMase, Career Coach, author, and public speaker public speaker with a fast-growing community of 800,000+ followers on social media

Follow Sam on LinkedIn: https://www.linkedin.com/in/samdemase/

Follow Sam on TikTok: https://www.tiktok.com/@apowermood?lang=en

Follow Sam on Instagram: https://www.instagram.com/apowermood/

Topics Covered: 

• Growing up with strong female role models
• Being called a bossy kid was her being a leader
• A good manager means showing up authentically, making connections and having empathy
• Working for One Fine Day, she moved into HR and found her superpower in people
• Parallel Pivoting
• Find your superpower - ask your friends/family and take assessment tests
• Messy Part of management is letting friends down if you can’t make change or firing people
• Sam bridges the gap between Gen Z and Gen X
• Sam starts a side hustle and gets written up for urging people to fight for equality
• Social Media as a job - being authentic garners the right audience and clients
  • Not forcing yourself to push through, and instead being honest makes people feel seen 
• Job hopping is common - what matters is your impact at a company, not amount of time
• Journey with anxiety and depression showing up in insomnia and trouble breathing
• Side hustles are a great way to build your dream career while having security 
• Dealing with Toxic Bosses - document everything and focus on communicating what will make your work better

Mentioned: 

Gap, One Fine Day, NYU, Columbia, StrengthsFinder Assessment, Clifton Strengths, authenticity, leadership, HR, TikTok, Instagram, ZipRecruiter, Forbes Business Insider, NBC Time, toxic bosses,

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What happens when your toxic business partnership implodes and nearly 20 years of work vanishes while you're getting your hair done? Gwen Whiting, co-founder of The Laundress, opens up about the brutal reality behind building a successful brand, selling it to Unilever—and watching everything she created collapse.

In this raw conversation, Gwen reveals how early tragedy shaped her resilience; surviving on credit cards for over a decade; why her career path was not marriage; and the devastating moment she became "the adopted child nobody wanted" after acquisition. From being dismissed as "too small to care about" to rebuilding what she believed was a tarnished legacy, Gwen shares the messy truth about starting over.

If you've ever felt like you're building on shaky ground or wondered if you have the strength to rebuild after betrayal, this episode will remind you that sometimes losing everything reveals your true strength.

Topics Covered: 

• Armoring up and fighting for myself. 
• Acting authentically/not transactionally, being honest.
• How to do very uncomfortable things and while knowing that your result isn't always gonna be good (and it may even hurt), and then go back the next day and do it again. 
• Relationships are the key to my success.
• My career path was not getting married.  I wasn’t going to marry myself off.
• Lesson learned: have your own financial independence Keeping control, 
• What gave me confidence
• White man chinos: my worst nightmare.

Show Notes

Guest: Gwen Whiting, co-founder, The Laundress, founder, The Fill

• Follow Gwen on LinkedIn: https://www.linkedin.com/in/gwenlwhiting/
• Follow Gwen on Substack: https://thelaundrylist.substack.com/
• Follow Gwen on Instagram: https://www.instagram.com/gwenlwhiting/?hl=en

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Job opportunities in her industry faded away slowly and then all of a sudden. So Emma Rosenblum committed to her side hustle and found a way to pivot into a new career altogether – she wrote a book.  A literary agent rejected it as "too mean,” but she found a way through. Then, when her manuscript accidentally leaked to her real-life community (the location of the book) with real residents' names still in it, the small-town drama was intense. Now a full-time novelist obsessively checking LinkedIn daily, Emma reveals how her competitive nature and insider-outsider perspective fuel both her satirical writing and her ongoing anxiety about what comes next.

Show Notes: 

Guest: Emma Rosenblum, Author, Editor in Chief

Follow Emma on LinkedIn: https://www.linkedin.com/in/emma-rosenblum/

Topics Covered

• Anxiety, Financial Insecurity, Health Worries, Motherhood, Work-Life Dramas, Side Hustles, Writing and Publishing, Being Competitive

Mentioned

Glamour Magazine, New York Magazine, Elle Magazine, Bloomberg, Bustle/Bustle Digital Group, Google, CAA, Meta

Kevin Kwan, Lucy Foley, Alexandra Machinist, Sarah Jessica Parker,
Natasha Bedingfield, Allison Roman, Carlos Alcaraz 

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Tony Awards, Grammys, a Pulitzer Prize, Emmy Awards. Next to Normal, If/Then, Hell's Kitchen, and NY State of Mind. Tom Kitt traded a Wall St. job offer (and paycheck) to follow his passion, a life making music, but that decision didn't come without great cost. He spent five years developing his first Broadway show, "High Fidelity," and it closed after just 10 days, sending him into months of depression and self-doubt. In this raw conversation, Kitt reveals how creative heartbreak became his greatest teacher, why collaboration and his relationships saved his career, and how saying "yes" to risky projects—including an epic pandemic Times Square performance—keeps him creating against all odds. From getting fired from his first music job to creating Next to Normal. Kitt's story is a masterclass in resilience. He shares hard-won wisdom about navigating brutal Broadway reviews, managing creative input overload, and why failure at any age can still become your greatest launching pad.

Topic Covered (with timestamps):

05:27 – The Morgan Stanley choice: Nine interviews and choosing art over finance 

07:19 – Early career struggles: Getting fired as a pivot moment 

09:49 – Meeting collaborators: Brian Yorkey and Rita's introductions 

12:18 – High Fidelity development: Five years from BMI workshop to Broadway 

16:41 – The garage band approach: Cabaret performances and producer discovery 

18:38 – When things go wrong: Boston reviews and Broadway closure after 10 days 

20:00 – Recovery and community support: Friends reaching out after failure 

21:14 – Next to Normal beginnings: Getting back on the horse 

22:16 – Saying yes during pandemic: Times Square performance and Billy Joel collaboration 26:05 – Billy Joel impact: Childhood hero and Emmy-winning "New York State of Mind" 

27:52 – Collaboration challenges: Working with long-time partners like Brian Yorkey 

29:32 – Managing creative feedback: Trusting audience reactions over individual opinions 

31:03 – Continuous learning: From SpongeBob to Shakespeare, staying curious 

33:03 – Artistic purpose: Creating physical reactions and inspiring others 

34:41 – Starting later in life: It's never too late, Billy Porter's example 

36:03 – Future dreams: Film scoring and musical television series 

36:24 – Rapid fire: Karaoke songs, reading list, and life advice

Mentioned: 

Hell's Kitchen, Jagged Little Pill, High Fidelity, American Idiot, Next to Normal, If/Then, “New York State of Mind”: https://www.nycnext.org/ny-state-of-mind

Brian Yorkey, Billy Joel, Billy Porter, Amanda Green, Jeffrey Seller, Kevin McCollum, Robin Goodman, Walter Bobbie, Green Day, Alanis Morissette, Times Square, 

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Feel like you're on the “wrong” path? Negin Farsad  (comedian, filmmaker, writer, actor, and activist) went from steady job as a NYC policy advisor to chasing laughs on lonely standup stages across the country.  As one of the few Iranian-American Muslim women in comedy, she’s built a career blending sharp political satire with deeply personal storytelling—using humor to tackle racism, sexism, and Islamophobia. From touring conservative towns with The Muslims Are Coming! to hosting Fake the Nation, Negin shares the messy leap from public policy to punchlines, turning passion into a paycheck, what it means to be a “social justice comedian,” and why she believes laughter is one of the most powerful tools for change.

Topics Covered: 

• Growing up Iranian-American in times of political hostility, and how early exposure to diversity while in Palm Springs shaped her worldview and comedic voice
• The leap from dual master’s degrees and a NYC policy advisor role to full-time comedy 
• Navigating initial disappointment from parents over career pivots before earning their understanding and support
• The pressures and trade-offs of turning a passion into a paycheck—and how that changes your relationship with the work you love
• Balancing motherhood, marriage, and career success while she and her husband both navigate “unstable,” gig-based artistic careers
• Using humor to challenge stereotypes, defuse protests, and reframe Muslim identity in American culture
• Diversifying her creative work across stand-up, film, writing, voice acting, activism, and unexpected gigs (including a psilocybin retreat)

Mentioned: 

• The Muslims Are Coming! (Documentary): https://www.imdb.com/title/tt2788710/
• Once Upon a Mattress (Musical): https://en.wikipedia.org/wiki/Once_Upon_a_Mattress 
• Comedy Central: https://www.comedycentral.com/ 
• Homeland (TV Series): https://www.sho.com/homeland 
• Wait Wait… Don’t Tell Me! (NPR): https://www.npr.org/programs/wait-wait-dont-tell-me/ 
• TED Talks: https://www.ted.com/speakers/negin_farsad 
• The Longest Table: https://www.longesttablecommunity.org/ 

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Ever feel like everyone else has it figured out while you're drowning in chaos? Sarah Personette's journey through Facebook, Twitter, and now Puck as CEO reveals the messy reality behind big-name success. She shares brutal truths about workplace bullies who wanted her gone, the isolating loneliness of leadership, and making gut decisions that horrified her father. From losing student elections repeatedly to navigating public failures at major tech companies, Sarah exposes how kindness became her secret weapon—not weakness, but a "structural force" that brought her back to three different companies. This raw conversation proves messiness and compassion can lead to extraordinary breakthroughs.

Show Notes: 

Guest: Sarah Personette, CEO of Puck

Follow Sarah on LinkedIn: https://www.linkedin.com/in/sarah-personette-4b71125/  

Topics Covered: 

• The childhood challenges that shaped her resilience and risk tolerance
• Why losing multiple student elections didn’t stop her but from chasing leadership roles
• The career move her father called “the worst decision ever,” and why she took it anyway
• How trusting her instincts guided her from job to job 
• Navigating workplace hostility and choosing to lead for the many, not the few 
• Taking a “gap year” to explore, connect, and clarify her goals. 
• The importance of boundaries in balancing C-suite leadership with motherhood and marriage 
• The importance of having a strong value framework 

Mentioned: 

Puck: https://puck.news/ 

Writers at Puck: John Heilemann, Dylan Byers, Julia Ioffe, Matthew Belloni, Baratunde Thurston, and more

Starcom MediaVest Group: https://www.starcomww.com/ 

Facebook (Meta): https://www.meta.com/ 

Twitter (X): https://x.com/ 

Hidden Potential by Adam Grant: https://adamgrant.net/book/hidden-potential/ 

Rotary International: https://www.rotary.org/en 

Whispering Angel Rosé: https://www.esclans.com/ 

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