Making It with Jess Ekstrom

In this episode of Making It with Jess Ekstrom, Jess sits down with former sports agent, author, and leadership expert Molly Fletcher. Molly shares how she went from sleeping on a friend’s couch in Atlanta to recruiting athletes in an industry that often did not expect a woman to be the agent in the room. She and Jess talk about being underestimated, asking for what you want before you feel ready, and building confidence from small wins along the way. Molly also explains why success means more to her now than the next big contract, and how boundaries, support, and a clear sense of purpose help women keep growing without running themselves into the ground.

• What’s at Risk If You Don’t Ask? Molly shares the question that helped her pursue opportunities before she felt ready.

• Being Underestimated: From a golf clubhouse that would not let her eat with her client to players who assumed she was someone’s assistant, Molly explains how she earned trust through preparation and knowledge.

• Confidence Comes from Evidence: Jess and Molly compare the ways they save reminders of past wins for moments when they doubt themselves.

• Protecting Your Energy: Molly talks about delegation, boundaries, and her “alignment audit” for spotting the gap between what matters most and where your energy actually goes.

• Redefining Making It: Twenty years ago, success meant signing the next player or negotiating a major contract. Today, Molly measures it by the impact she can have on others.

Learn more about Molly and The Edge at https://mollyfletcher.com

In this insightful episode of Making It with Jess Ekstrom, Jess sits down with Sabina Osorio, Senior Director of Growth Marketing for TED Conferences, to explore what transforms an idea into something people can understand, remember, and share.

Sabina reveals the preparation behind a powerful TED Talk, including why speakers must edit ruthlessly, rehearse extensively, and resist the urge to sell from the stage. She also explains why TED receives thousands of submissions each week and what an idea needs to stand apart.

Jess and Sabina also discuss the dark side of going viral, building genuine professional relationships without feeling transactional, and why being helpful is more valuable than chasing the largest possible audience. Sabina opens up about overcoming perfectionism, navigating imposter syndrome at TED, and redefining success as protecting her joy, family time, and life outside of work.

EPISODE HIGHLIGHTS

• What Makes an Idea TED-Worthy: Sabina explains why a strong idea must be original, carefully researched, easy to understand, and relevant to people around the world.

• The Work Behind a TED Talk: Discover why speakers can spend more than 100 hours editing, fact-checking, rehearsing, and refining a single talk. 

• Why Going Viral Shouldn’t Be the Goal: Sabina shares how viral content can attract the wrong audience and pull creators away from the community they actually want to serve. 

• Stop Letting Perfectionism Hold You Back: Sabina reveals how she replaced the pursuit of perfection with an 80/20 mindset that allows her to act, learn, and grow.

• Build Relationships Before You Need Them: Learn how genuine curiosity, consistent connection, and offering value helped Sabina build the relationship that eventually opened the door to TED.

• Let Your Team Find Their Own Way: Sabina explains why leaders should resist stepping in too quickly and give capable people the space to solve problems differently.

• Redefining What It Means to Make It: Ten years ago, success meant climbing the corporate ladder. Today, Sabina measures it by joy, family time, hobbies, and a career that supports her life.

In this inspiring and eye-opening episode of Making It with Jess Ekstrom, Jess sits down in person with disability advocate, social entrepreneur, and author Tiffany Yu. Tiffany reflects on acquiring her disability at nine years old after a traumatic car accident that permanently paralyzed her arm. She opens up about the cultural shame, silence, and assimilation tactics she navigated for over a decade before eventually pivoting toward disability pride and community building. Tiffany breaks down the concept of the "assumption funnel" that systemically locks disabled people out of job markets and opportunities, while dismantling popular tropes like the "hero's journey" or "overcoming" disability. She also reveals how, at age 37, she began chasing joy by tapping into the interests of her nine-year-old self—a journey that ultimately led her to join the USA Paraclimbing Team with her eyes set on the LA 2028 Paralympics.

Episode Highlights

• The "Assumption Funnel": Tiffany breaks down how societal assumptions—like assuming someone with a paralyzed arm cannot type or do an office job—create cascading barriers to employment, book deals, and basic accessibility.
• Moving Beyond Assimilation: How growing up in an immigrant household influenced Tiffany's early decisions to hide her disability and keep track of lies, and what finally sparked her journey toward disability pride.
• Dismantling the "Hero's Journey": Why narratives framing disabled people as "overcoming" their disabilities or accomplishing goals "in spite of" them are harmful, and why language should reflect living with disability.
• Handling Unsolicited Advice & Microaggressions: The mental fatigue of navigating intrusive questions, viral comment sections, and unsolicited medical advice, alongside the concept of trying to be a "sandbag clown".
• Reinventing Yourself at 37: How Tiffany re-engaged with hobbies her nine-year-old self loved, stepping onto a rock climbing wall 19 years after her accident despite internalizing doubts.
• Road to the LA '28 Paralympics: From tying for last at her first competition to earning a spot on the USA Paraclimbing Team and competing globally.
• Play, Fun, Joy (PFJ): Why rest and joy are valid forms of productivity, and how Tiffany balances her professional advocacy work with personal fulfillment.

About Our Guest

Tiffany Yu is a disability advocate, social entrepreneur, speaker, and the author of The Anti-Ableist Manifesto. She is the founder of Diversability, an award-winning ecosystem democratizing visibility, community, and economic opportunity for disabled people. Named to the Forbes Accessibility 100 and a multi-time TED speaker, Tiffany is also a competitive athlete on the USA Paraclimbing Team working toward the LA 2028 Paralympic Games.

In this enlightening episode of Making It with Jess Ekstrom, Jess sits down with Claude Silver, the Chief Heart Officer at VaynerMedia and author of Be Yourself at Work. Claude opens up about her non-traditional path to executive leadership—from struggling with academics and feeling like a failure in her early 20s to finding her calling in transformative psychology and emotional intelligence. She pulls back the curtain on what a Chief Heart Officer actually does, how she helped shift VaynerMedia’s hiring philosophy from "culture fit" to "skillset fit and culture addition", and why feedback should be viewed as connection rather than correction. Plus, Claude shares her perspectives on parenting beyond grades, overcoming workplace gossip, and maintaining irreplaceable human connection in an era dominated by AI.

Episode Highlights:

• Overcoming School Struggles: Claude reflects on how poor test scores affected her early confidence, realizing later in life that traditional schooling tests for the wrong skills while overlooking emotional intelligence.
• The "Kindness Balloon" & Parenting: How Claude teaches her children values like commitment, work ethic, and everyday kindness over simple academic performance.
• Ditching "Culture Fit": Why hiring for "culture fit" creates homogenous teams, and how VaynerMedia shifted to hiring for "skillset fit and culture addition" to foster real diversity of thought.
• What a Chief Heart Officer Does: Defining the role as serving as the emotional framework for a 2,000-person global company, balancing empathy and people-first culture with high-performance accountability.
• The Danger of Shrinking at Work: Addressing the cost of hiding your true self at work, and why "dipping your toe in the water" prevents burnout and mental health decline.
• Reframing Feedback as Connection: Why humans naturally fear feedback, and how managers can deliver specific, kind, current, and actionable feedback that builds trust.
• Analog Moments in an AI World: Why AI will handle data gathering and organizational efficiency, but human curiosity, raw vulnerability, and in-person (IRL) connection will remain the ultimate differentiator.
• Redefining "Making It": How Claude transitioned from working 15-hour weekend shifts to earn validation to prioritizing how she spends her time and choosing experiences that fill her spiritual and relational bucket.

About Our Guest:

Claude Silver is the Chief Heart Officer at VaynerMedia, where she serves as the emotional framework for over 2,000 employees globally. A former advertising executive with a background in transformative psychology, Claude is a renowned speaker and the author of Be Yourself at Work. Her mission centers on scaling empathy, emotional intelligence, and relational connection within fast-paced corporate environments, empowering individuals to unlock their full potential and bring their authentic selves to work every day.

In this energizing episode of Making It with Jess Ekstrom, Jess sits down with Claire Coder, the visionary founder of Aunt Flow. Claire shares the exact moment at age 18 that inspired her to drop out of college to make tampons and pads just as free, dignified, and accessible as toilet paper in public restrooms. She opens up about the evolution of her company—from packing subscription boxes in a U-Haul storage unit to raising nearly $17 million in venture capital and stocking Aunt Flow dispensers across 70,000 bathrooms worldwide. Claire provides a candid look at the realities of being a B2B founder, including why she considers entrepreneurship a "genetic defect," navigating the surprising pushback she gets from female decision-makers, and why balancing a world-changing social impact requires owning a unapologetically capitalist mindset.

Episode Highlights:

• The "Quarter Dispenser" Moment: Claire recalls her monumental 18th-period story that exposed the lack of basic period care in public restrooms and sparked the idea for Aunt Flow.
• Dropping Out for Menstruation: Navigating the awkward, bold conversations with parents and advisors when leaving Ohio State University after one semester to build a period care empire.
• From U-Haul to B2B Leader: The scrappy early days of running a subscription box out of a 3rd-floor apartment and storage unit before pivoting to patented B2B bathroom dispensers.
• A Shift in Policy: Celebrating the legal and cultural shift across 27 states that now mandate or fund free period products in school bathrooms.
• "No Mission Without Margin": A raw masterclass on why purpose-driven startups must maintain for-profit discipline and high performance to create true long-term impact.
• Selling Tampons to Men vs. Women: Why heads of facilities (mostly men) are often an easy sell, and the unexpected challenge of overcoming internalized taboo from female decision-makers.
• Handling 86 VCs Rejections: What Claire learned while pitching investors, raising $17M, and how she gives direct, constructive feedback to the next generation of founders.
• The Art of "Playing the Game": Why context-switching and matching the energy of any room—from janitorial trade shows to Manhattan rooftops—is a essential founder superpower.

About Our Guest:

Claire Coder is the founder and CEO of Aunt Flow, a B2B company that designs and installs patented, free-play dispensers packed with organic cotton tampons and pads in public and corporate bathrooms. After dropping out of college at age 18 to solve period poverty and bathroom inequality, Claire has built Aunt Flow into a global brand operating in over 70,000 bathrooms across all 50 states and multiple countries. She has raised nearly $17 million in venture capital, donated over 7 million period products to communities in need, and continues to champion menstrual equity worldwide.

Jess sits down with Libby Ward, the creator behind the viral movement Diary of an Honest Mom and author of Honest Motherhood. Libby shares her personal evolution from a self-described people-pleasing "plate spinner" to a fierce advocate for maternal mental health. She opens up about the crushing shift from the "baby parade" celebration of pregnancy to the overwhelming isolation of postpartum depression and medical emergencies. Libby also details her decision to step back from teaching, how viral TikTok success changed her relationship with content creation, her choice to keep her children's faces off social media, and how she unlearned decade-long habits of self-doubt to proudly own the value of her work and story.

Episode Highlights:

• The "Baby Parade" Trap: Libby unpacks how society showers pregnant women with celebration, only to leave mothers feeling invisible once the baby arrives.
• The Postpartum Reality Check: A raw reflection on navigating a newborn medical emergency and mastitis in a hospital recliner, realizing how quickly a mother's basic needs are sidelined.
• Sociology & "Cycle Breaking": How returning to university in her 30s introduced Libby to terms like mental load and patriarchy, revealing that her burnout was systemic rather than a personal failure.
• Finding Community on TikTok: The origin of Diary of an Honest Mom and how going viral provided a safe testing ground to dismantle maternal shame.
• Protecting Kids in the Digital Age: Why Libby strictly keeps her children off camera, respecting their autonomy and avoiding the pressure of converting family life into content.
• Overcoming the Fear of "Selling": How years of therapy helped Libby transition from endlessly giving free content to confidently owning the life-changing value of her book.
• Redefining "Making It": Why success today isn't about the next book launch or viral video, but the rare, grounded ability to be fully present in the moment right in front of her.

About Our Guest:

Libby Ward is a digital creator, speaker, maternal mental health advocate, and the author of Honest Motherhood. Known digitally as Diary of an Honest Mom, Libby launched her platform to break cycles of shame, martyrdom, and perfectionism in parenting. With millions of followers across social platforms, she provides a refreshing, unfiltered look at mental health, division of labor, and the realities of modern motherhood, empowering women to prioritize their well-being and own their inherent worth.

Jess sits down with Carly Zakin and Danielle Weisberg, the brilliant co-founders of The Skimm. Proving that cold DMs can actually work , Jess dives deep into their 14-year entrepreneurial journey — from meeting during a study abroad program in Rome and quitting their dream jobs at NBC News to building a massive news media empire and raising multiple rounds of venture capital. Carly and Danielle share the raw realities of navigating burnout , maintaining a strictly objective newsroom during highly polarized elections , and drafting a business "prenup" to protect their relationship. They also pull back the curtain on what it actually looks like when a massive acquisition deal closes — bathrobes included.

Episode Highlights:

• The Art of the Cold DM: Jess shares how she booked the co-founders of The Skimm simply by taking a chance and shooting her shot in their inbox.
• The "Hated by Both Sides" Metric: Carly and Danielle reflect on the early challenges of writing unbiased news, revealing how getting angry mail from both sides of the political aisle proved they were doing their jobs right.
• Ditching the Coastal Bubble: How The Skimm took on the responsibility of representing millennial women across the entire country, balancing an audience split down the middle politically.
• The Reality of Founder Burnout: A vulnerable look back at the chaotic pandemic era when business metrics were booming, but the sheer stress of remote management had them ready to walk away.
• The Co-Founder "Prenup": The exact advice they received from a lawyer that saved their friendship, and how keeping strict boundaries between "friend time" and "work time" preserved their 20-year bond.
• An Anti-Climactic Acquisition: The hilarious behind-the-scenes story of closing their life-changing acquisition deal over an early morning Zoom call while Danielle was still in a bathrobe.
• What Money Actually Buys: A candid conversation on why the narrative that "money doesn't buy happiness" is flawed, and how capital buys crucial support networks, childcare, and peace of mind for working mothers.
• Adapting to the AI Revolution: Carly explains why women must build agency in their careers by staying up to date on technology as AI reshapes the global job market.

About Our Guests:

Carly Zakin & Danielle Weisberg are media entrepreneurs, journalists, and the co-founders of The Skimm. After meeting in college and working together as producers at NBC News , they left their corporate trajectories to launch a daily newsletter from their couch. Together, they scaled The Skimm into a dominant multi-platform brand that fundamentally changed how millions of millennial women consume news and manage their civic, financial, and professional lives. Through their platform, they have registered over two million voters and championed massive structural transparency around paid family leave. Following their successful acquisition , they continue to advocate for technology education , career autonomy , and structural workplace support for women.

Recorded on location in Austin, Texas, Jess catches up with long-time friend Jessica Honegger, the visionary founder of Noonday Collection. Jessica shares the raw, inspiring origin story of how she pawned her grandmother’s gold jewelry to build a website and launched Noonday as a simple fundraiser to finance her son's adoption from Rwanda. After scaling Noonday into an explosive powerhouse and one of Inc.’s fastest-growing companies, she faced a massive crossroads when post-COVID market shifts triggered an industry-wide collapse for traditional direct sales. Jessica pulls back the curtain on why she chose to stay and reinvent the company rather than liquidate, her experience hiring her husband as her operational partner, and how she completely dismantled the "mom guilt" narrative while raising a family alongside a globally integrated business.

Episode Highlights

• The $0 Scrap Business Blueprint: Jessica opens up about the financial desperation that led her to pawn her grandmother's jewelry just to build her first business website.
• The Adoption Rooted Mission: How a desire to bring home her son from Rwanda turned an organic, one-night living room trunk show into a sustainable global marketplace.
• Surviving the Direct Sales Extinction: A transparent look at how post-COVID changes caused a collapse in direct sales, forcing Noonday to transition to wholesale partnerships like Nordstrom and boutique retailers.
• Hiring Your Spouse as COO: Jessica reveals what it was like to hire her husband as a turnaround partner and the unique boundaries they navigate to separate boardroom talk from their marriage.
• Defeating the "Mom Guilt" Trap: How leaning on empirical data and aligning her career with global female economic empowerment helped her realize that working was a benefit, not a detriment, to her children.
• Integrating Work and Family: The philosophy of building a "family vision" rather than a solo venture, including bringing her children on international sourcing trips.
• Ditching "Point of Arrival" Living: A masterclass in letting go of constant comparison, embracing plateaus, and changing your posture to one of daily gratitude rather than chasing future metrics.

About Our Guest

Jessica Honegger is an author, speaker, podcaster, and the founder of Noonday Collection, a socially conscious fashion brand that partners with artisans across the globe to create sustainable economic opportunities. A passionate advocate for international development and human rights, Jessica is the author of Imperfect Courage: Live a Life of Purpose by Leaving Your Comfort Zone. Over the past 15 years, her brand has mobilized thousands of ambassadors, built a sustainable middle class for dozens of international artisan communities, and emerged as a leading voice in ethical entrepreneurship.

In this special live episode of Making It with Jess Ekstrom, recorded in front of a live audience at Mic Drop Live, Jess sits down with Allyson Felix, the most decorated track and field athlete of all time. While her medal count is legendary, her true legacy lies in her resilience off the track. Allyson opens up about her bold decision to train for the LA 2028 Olympics at age 40, defying societal expectations for women in their 40s. She shares the raw details of navigating a traumatic pregnancy, being dropped by a major sponsor, and turning that adversity into a powerful crusade for maternal health protections for female athletes. Plus, Allyson pulls back the curtain on the world of entrepreneurship, explaining why she and her brother co-founded Saysh—a footwear brand explicitly designed to fit the unique anatomy of the female foot.

Episode Highlights

• Defying Age Narratives: Allyson discusses her decision to train for the LA 2028 Olympic team at 40, challenging the traditional limits placed on women as they age.
• Finding Your Voice as an Introvert: How a self-described quiet people-pleaser evolved into one of the world's most outspoken advocates for working mothers.
• The Turning Point with Nike: The painful reality of being offered a 70% pay cut after becoming pregnant, and how it sparked a New York Times op-ed that forced corporate policy changes across the industry.
• Overcoming a Traumatic Birth: Allyson reflects on her severe preeclampsia diagnosis, her daughter's month-long NICU stay, and how the experience amplified her passion for addressing maternal health disparities for women of color.
• The Reality of Being a Founder: Why being a female founder is harder than running the 200 meters, overcoming imposter syndrome, and facing the harsh statistics of venture capital funding.
• The Gender Bias in Footwear: Uncovering the industry secret that most major brands design women's athletic shoes using molds of men's feet, and how Saysh is changing the game.
• Redefining "Making It": How Allyson’s definition of success shifted from winning singular gold medals to creating lasting systemic impact and having the courage to try.

About Our Guest

Allyson Felix is an iconic American track and field athlete and the most decorated competitor in the sport's history, holding 11 Olympic medals. Beyond her unparalleled athletic achievements, she is a fierce advocate for maternal health, gender equality, and working mothers. Following her historic break from Nike over pregnancy protections, she co-founded Saysh, a community-centered footwear brand that designs athletic shoes specifically engineered for the female form. Allyson continues to break barriers as an entrepreneur, activist, and mother.

Resources & Links:

• 📖 Making It Without Losing It by Jess Ekstrom: Available now — USA Today bestseller
• 🎤 Mic Drop Workshop: micdropworkshop.com — helping women become seen and paid as thought leaders
• 📸 Follow Jess on Instagram: @jessekstrom
• 🎙️ Making It with Jess Ekstrom: Subscribe + leave a review wherever you listen

Have you ever hit the thing you were chasing — the milestone, the launch, the moment — and felt the goalpost immediately move? Have you ever wondered if ambition itself could be both the engine and the thief?

This episode is a live one. Jess is in New York City at Argent's flagship store for the launch of her new book Making It Without Losing It — officially a USA Today bestseller — and she's in conversation with her longtime friend and founder of Pep Talk Her, Meggie Palmer. You're going to hear sirens. You're going to hear the room. You are, as Jess says, in there with them. And honestly? It makes this one of the most electric conversations in the feed.

They dig into the dopamine science behind why we're never satisfied at the finish line (hint: your brain is getting the hit somewhere else entirely), what it really means to be ambitiously present, and why Jess signed up for stand-up comedy classes five months postpartum just to remind herself it was okay to be bad at things. The room also gets in on it — with questions from the audience about corporate life vs. entrepreneurship, raising kids who know how to fail, and the uncomfortable but necessary exercise of writing your own obituary before you need one.

In This Episode

Jess and Meggie cover the core ideas behind Making It Without Losing It: the difference between anxious ambition and inspired ambition, why the smash is better than the cash, and how Jess went from measuring success by how many stages she could get on — to measuring it by how many stages she could help other women get on. Plus: live audience Q&A, a meditation on legacy, and the one question Jess keeps posted in her office that changes everything.

Highlights From the Room:

• The dopamine study that reframes everything — why your brain rewards the anticipation and the process, not just the result
• Anxious ambition vs. inspired ambition — one comes from feeling behind; the other comes from feeling called
• The piggy bank smash — and why the build might actually be the good part
• Stand-up comedy at five months postpartum — what Jess needed to shock her nervous system back to life after her daughter was born
• "I don't do it all" — Jess's most honest answer to the question everyone asks
• The relay, not the race — what are you doing today that makes enough progress for the person behind you?
• Your obituary, written now — the silent retreat exercise that Jess keeps on her office wall and asks readers to try at the end of the book
• Don't just complete your goals. Outlive them. — the framework for thinking about legacy that doesn't require a crisis to activate

About Meggie Palmer

Meggie Palmer is the founder of Pep Talk Her, a platform and community on a mission to close the gender pay gap — helping women negotiate more, earn more, and get promoted faster. A former journalist turned advocate, Meggie brings the same sharp, warm energy to every conversation she hosts. Find her and her Thank You Thursday practice wherever she shows up online.

Resources & Links

• 📖 Making It Without Losing It by Jess Ekstrom: Available now — USA Today bestseller
• 🎤 Mic Drop Workshop: micdropworkshop.com — helping women become seen and paid as thought leaders
• 💼 Pep Talk Her: Follow Meggie Palmer for salary negotiation resources and community
• 👗 Argent: Premium women's workwear — argentwork.com
• 📸 Follow Jess on Instagram: @jessekstrom
• 🎙️ Making It with Jess Ekstrom: Subscribe + leave a review wherever you listen

Produced by Making It with Jess Ekstrom & Walk West | Recorded live at Argent NYC

🕯️ Soulful Sidebar: What Would Your Obituary Say?

At a silent retreat Jess didn't fully read the fine print for, the theme turned out to be death and dying. She almost left. She didn't. And it cracked something open.

The exercise: write what you'd want your obituary to say. Not as a morbid act — as a compass. Am I living the life that people would say this about?

Most of us wait for a diagnosis or a close call to ask that question. But what if you didn't need the crisis? What if the awareness — right now, today — was enough to course-correct?

You don't just get to complete goals in this lifetime. You get to set goals that outlive you. That's not a burden. That's the whole point.