Making It with Jess Ekstrom

Jess Ekstrom
  • 5.0 (303)
  • Entrepreneurship
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Making It with Jess Ekstrom is a top rated business podcast designed to help you amplify your ideas, influence and income. We have a special focus on amplifying women's voices, but this show is open to everyone. Tune in every other Tuesday to hear from Forbes Top Rated Speaker, Jess Ekstrom as she talks to speakers, authors and entrepreneurs who are crushing it in their own way.

  1. Oct 13

    Making It to 2.7 Million Girls with Girls on the Run Founder Molly Barker

    In this honest and heartfelt episode of Making It with Jess Ekstrom, Jess sits down with Molly Barker, founder of Girls on the Run, a program that has reached 2.7 million participants. Jess opens with a confession she’s never shared before: she cheated in Girls on the Run. Molly responds with her own childhood story, opening a conversation about competition, comparison, and the pressure girls feel to prove they’re good enough. Molly shares how her journey through addiction and recovery helped inspire Girls on the Run, which began with just 13 girls. She introduces the “girl box”—the expectations that teach girls to shrink themselves into who they think they should be—and explains why moving forward at your own pace matters more than finishing first. Jess and Molly also get candid about motherhood, the pressure to be present, and learning to see other women’s success as possibility rather than competition. From hiring people with different strengths to navigating tension between a founder’s big ideas and an organization’s need for structure, Molly reflects on what it takes to build something that can thrive beyond you. She opens up about leaving the organization she founded, finding her identity afterward, and how her definition of “making it” has shifted toward connection, presence, and being herself. EPISODE HIGHLIGHTS • The Cheating Confession: Jess reveals her unexpected Girls on the Run story, and Molly shares the childhood experience that helped shape her approach to competition. • Beyond the “Girl Box”: Molly explains how girls learn to measure themselves against expectations—and how running helped her reconnect with who she was. • From Recovery to 13 Girls: Molly shares the personal turning point and small beginnings behind Girls on the Run. • The Pressure to Be Present: Jess and Molly discuss motherhood, ambition, and why even relaxing can start to feel like another task to get right. • Building Beyond Yourself: Molly reflects on asking for help, hiring people with different strengths, and balancing innovation with sustainable growth. • “I’m the Boss of My Own Brain”: A memorable finish-line story reveals what confidence and self-trust can look like through a child’s eyes. • Life After Being the Founder: Molly gets honest about leaving Girls on the Run, redefining her identity, and finding meaning in her next chapter. ABOUT OUR GUEST Molly Barker is the founder of Girls on the Run, a program that combines movement with lessons in confidence, connection, and personal growth. With a master’s degree in social work and experience in drug prevention, Molly created the original curriculum and launched the program with 13 girls. A speaker and storyteller, she continues to explore the experiences that shape girls and women through her book, Running Free: Beyond the Girl Box, and her podcast project, Unboxing Girlhood. CHAPTERS 00:00 Jess’s Girls on the Run Confession02:22 Competition, Comparison, and Feeling Enough05:10 Motherhood and the Pressure to Be Present07:24 The Girl Box and Molly’s Origin Story11:06 Starting Girls on the Run with 13 Girls13:58 Building a Team and Letting Go of Doing Everything16:40 Balancing Big Ideas with Sustainable Growth19:48 Being the Boss of Your Own Brain21:16 What Girls Need from the Adults Around Them26:36 Leaving the Organization You Founded30:33 Running Free and Unboxing Girlhood32:14 What Making It Means to Molly Now

  2. Sep 29

    Making It in a Man’s World with Molly Fletcher

    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

  3. Sep 16

    Making It to the TED Stage with Sabina Osorio

    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.

    Making It to the TED Stage with Sabina Osorio

  4. Sep 1

    Making it to the World's Top 10 Paraclimbing Athletes with Tiffany Yu

    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.

  5. Aug 18

    Making it to Chief Heart Officer at VaynerMedia with Claude Silver

    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.

    Making it to Chief Heart Officer at VaynerMedia with Claude Silver

  6. Aug 11

    Making it to Free Tampons in Every Bathroom with Claire Coder

    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.

    Making it to Free Tampons in Every Bathroom with Claire Coder

  7. Jul 28

    Making it to Honest Motherhood with Libby Ward

    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.

  8. Jul 14

    Making it to an Audience of 12 Million with the Founders of TheSkimm, Carly Zakin and Danielle Weisberg

    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.

    Making it to an Audience of 12 Million with the Founders of TheSkimm, Carly Zakin and Danielle Weisberg
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Making It with Jess Ekstrom is a top rated business podcast designed to help you amplify your ideas, influence and income. We have a special focus on amplifying women's voices, but this show is open to everyone. Tune in every other Tuesday to hear from Forbes Top Rated Speaker, Jess Ekstrom as she talks to speakers, authors and entrepreneurs who are crushing it in their own way.

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