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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What do Prince, The Secret, and Colleen Hoover have in common? They all worked with Judith Curr to publish their books. Judith's career has been quite a trip: from selling her brother's engine block to a junk dealer in a very small Australian town. to selling Dior to pharmacies door-to-door, to revolutionizing book publishing—founding Atria Books, discovering tomorrow's bestsellers today, and now steering HarperOne into uncharted territory.  From Sydney to New York, Judith has made a career of calculated risks and bold bets. Ready to peek behind the curtain of modern publishing? Judith spills on talent-spotting, industry shake-ups, and why the future of books is more exciting than ever.

Show Notes: Guest: Judith Curr, President and Publisher of HarperOne Follow Judith on LinkedIn: https://www.linkedin.com/in/judith-curr-a72b80/ Follow Judith on Instagram: https://www.instagram.com/judithcurr/?hl=en

What You'll Discover:

• The career pivot that changed everything—from selling Dior lipstick to selling million-copy bestsellers
• How a gutsy move from Australia to New York launched her American publishing empire
• Inside the creation of Atria Books—the Simon & Schuster imprint that became a cultural force
• Her secret sauce for spotting breakout authors (hello, Colleen Hoover!) before they explode
• Why she fights for underrepresented voices—and how it's reshaping the industry
• Her vision for HarperOne's future in our AI-powered, globally connected world

Mentioned: 

Christian Dior: https://www.dior.com/en_us/beauty 

Simon & Schuster: https://www.simonandschuster.com/ 

Atria Books: https://www.simonandschusterpublishing.com/atria/ 

HarperOne: https://www.harpercollins.com/pages/harperonegroup 

HarperCollins: https://www.harpercollins.com/ 

The Secret by Rhonda Byrne: https://www.thesecret.tv/products/the-secret-book/

Countdown to Riches by Rhonda Byrne: https://www.thesecret.tv/countdown-to-riches/ 

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Irina Novoselsky landed her first CEO gig at just 32 years old. She’s now CEO of Hootsuite, a social media management platform with 16 million users in 175 countries. Even though her career has been a rocket ship, she’s had a lot of messy parts and pivots that’s shaped who she is and how she operates. That includes being out of work for months at a time and really questioning whether she was ever going to get a job again. If you’ve ever felt like you were on the wrong path entirely, this episode is a must-listen. 

Show Notes: 

Guest: Irina Novoselsky, CEO of Hootsuite

Follow Irina on LinkedIn: https://www.linkedin.com/in/irina-novoselsky/

Follow Irina on Instagram: https://www.instagram.com/irinanovoselsky/ 

Topics Covered:

• Growing up as a refugee in NYC and embracing immigrant hustle
• Cold-emailing her way into investment banking at 19
• Leaving prestigious finance roles to find her passion
• Becoming a first-time CEO at 32—and the identity shift it required
• The power of relentlessness, self-belief, and learning out loud
• Why she leads with authenticity (and uses emojis unapologetically!)
• How social media became her leadership superpower
• Finding balance her way—and why she prioritizes sleep over everything

Mentioned:

Hootsuite: https://www.hootsuite.com/
Outlive by Peter Attia https://peterattiamd.com/outlive/

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Discover the real story behind Another Tomorrow with Vanessa Barboni Hallik, who left Wall Street for a mission in sustainable luxury fashion. In this candid interview with Maryam Banikarim on "The Messy Parts Podcast," Vanessa reflects on career pivots, making meaning from hardship, starting a business during COVID, and how purpose and authenticity drive her leadership. If you’re looking for a boost of inspiration, lessons for entrepreneurship, or an inside look at sustainable fashion, this conversation is unmissable.

Show Notes: Guest: 

• Vanessa Barboni Hallik, Co-CEO, Chair, Another Tomorrow
• Follow Vanessa on LinkedIn: https://www.linkedin.com/in/vanessabarbonihallik/
• Follow Vanessa on Instagram: https://www.instagram.com/vanessaanabarboni/
• Follow Another Tomorrow on Instagram: https://www.instagram.com/anothertomorrow/

Topics Covered: 

• Introduction & Vanessa’s early life: growing up in the Midwest
• Coping with family mental health & loss; the impact on resilience
• Shifting from architecture to economics & landing on Wall Street
• Facing imposter syndrome, self-editing at work, and defining success
• Quitting (three times): career pivots, asking for what you want, and lessons learned
• Discovering sustainability and building Another Tomorrow
• Launching a brand as the pandemic hit: how to survive a sudden crisis
• Meditation, slowing down, and evolving as a leader
• Redefining success, working with partners, and closing advice
• Rapid fire: favorite songs, reading list, surprising facts

Mentioned: 

• Another Tomorrow
• Morgan Stanley
• B Corp
• TM (Transcendental Meditation)
• Berkeley
• Cornell's program
• Farm to Closet model

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