Have you ever had a dream job—the kind people tell you is the "coolest job in the world"—only to realize that your identity has become so wrapped up in it that you don’t know who you are without the title? How do you walk away from a legacy to build something entirely your own?

Welcome to Making It with Jess Ekstrom. This week, Jess sits down with Lindsay Shookus, the legendary former producer and head of the talent department at Saturday Night Live. After 20 years of discovering stars and managing the chaos of live television, Lindsey made the "wobbly" decision to leave 30 Rock and redefine what success looks like on her own terms.

In this candid conversation, Lindsey opens up about the grit required to survive 20-hour days, the lonely reality of hyper-fame, and the epiphany that led her to co-found Women Work Fing Hard*—a community built on active support rather than just "mentorship."

Tune in for:

• The SNL Hustle: How a girl from Buffalo with "Southern-adjacent" roots at UNC-Chapel Hill landed a job at SNL and worked her way from assistant to talent mogul.
• The Fame Pedestal: What Lindsey learned about success by watching the world’s most famous people up close, and why "street cred" isn't all it's cracked up to be.
• The "Wobbly" Transition: The identity crisis that follows leaving a high-profile career and how to navigate the "data" of who stays in your life when the power of your position is gone.
• Receive the Motherfing Data:* Lindsey’s viral-ready advice on relationships and business—how to stop "waiting to be chosen" and start looking at people's actions as objective information.
• Women Work Fing Hard:* The accidental origin story of her women’s community and why the goal is always "How can I help you?" rather than "Who can help me?"
• The Curse of the Good Girl: Why Lindsey normalizes "bombing" for her 12-year-old daughter and the importance of being uncomfortable to get better.
• Building a Boat: What it’s like for an ambitious woman to find a partner who asks, "How can I best support you?"
• The Art of the Question: Why being a curious mind is the most undervalued skill in networking and life.

About Lindsay Shookus:

Lindsay Shookus is an Emmy Award-winning producer, speaker, and coach. Best known for her two-decade career at Saturday Night Live, she now uses her expertise in talent and trust to advise hedge funds, produce documentaries, and empower women through her community, Women Work F***ing Hard.

Resources & Links:

• Lindsay Shookus’s Website: https://lindsayshookus.com
• Women Work Fing Hard:*
• Follow Lindsey on Instagram: @Shookusshookus 
• The Curse of the Good Girl by Rachel Simmons:
• Making It with Jess Ekstrom is produced by Walk West and brought to you by Mic Drop Workshop.

How to "Receive the Data" in Your Career

Lindsey talks about treating feedback-and even rejection-as objective data. This shift moves you from an emotional participant to a strategic scientist of your own life.

Visit walkwest.com to see more!

Have you ever felt like you had to mute your personality, change your style, or "fit the mold" just to be taken seriously in business? What if the very things people told you to tone down were actually your greatest superpowers for building a $100M empire?

Welcome to the premiere episode of Making It with Jess Ekstrom. This week, Jess sits down with Anne Mahlum, the visionary founder of [Solidcore] and Back on My Feet. Anne famously raised $210 million from private equity while wearing see-through crop tops, proving that authenticity isn't just a buzzword—it’s a high-stakes competitive advantage.

In this raw and uncensored conversation, Anne pulls back the curtain on her $100 million exit, why she refuses to be a "one-hit wonder," and how she transitioned from a "starving founder" to a fitness mogul. They dive deep into the "hustle muscle" fueled by early pain, the importance of "happy endings" in business, and the biological shifts of entering her next big chapter: motherhood.

Tune in for:

• The story behind the see-through crop tops and why Anne refused to change her hair or style for private equity partners.
• Why "fake it till you make it" is bad advice and how trying to fit in actually makes you feel smaller and less confident.
• Anne’s three core values—Authenticity, Transparency, and Winning—and how they guided her through $100M negotiations.
• The "Chip on the Shoulder": Why many high-performing entrepreneurs are fueled by a need to prove themselves and the realization that achievement doesn't equal love.
• The $100 Million Exit: How Anne planned her last day years in advance to ensure a celebratory, "non-messy" transition.
• Financial Leverage: Why Anne advises founders to take money off the table early so they aren't "starving" when it's time to negotiate an exit.
• Radical Responsibility: Why claiming "it's my fault" for everything from low energy to a stalled career is the ultimate power move to regain control.
• Relationships and Polarity: Anne’s take on settling into a partnership with her husband as an ambitious, breadwinning woman.
• How to find a "game you can win" by sharpening your unique 8, 9, and 10-level skill sets.

About Anne Mahlum:

Anne Mahlum is a speaker, investor, and the founder of [Solidcore], a boutique fitness powerhouse she scaled to 100+ locations before a massive exit. She is also the founder of the non-profit Back on My Feet. Anne is a dedicated advocate for financial literacy and empowers founders to build businesses that reflect their truest selves.

Resources & Links:

• Anne Mahlum’s Website: https://annemahlum.com
• Follow Anne on Instagram: @annemahlum
• Brene Brown’s Values Exercise:
• Making It with Jess Ekstrom is produced by Walk West and brought to you by Mic Drop Workshop.

A Note on Radical Responsibility & Starting Blocks

In this episode, Anne and Jess discuss the reality of "starting blocks." While Anne emphasizes taking radical responsibility, she also acknowledges the statistical realities of the business world. For context, women-led startups received only about 2% of total venture capital funding in recent years, and for Black and Latina founders, that number often drops below 1%.

As Anne notes, recognizing privilege or systemic hurdles doesn't mean you stop working; it means you use your position to "lift others up" and change the statistics for the next generation of founders.

Visit walkwest.com to see more!

What if an algorithm could perfectly articulate the unfair advantages men have in business, and what if that knowledge was the catalyst you needed to completely change your career?

In the season finale on Amplify, Jess sits down with LauraAura, host of the wildly popular Gutsy Podcast and an acclaimed speaker. Laura shares the moment a Taylor Swift song drove her to ask ChatGPT a provocative question: "How would my career look different if I were a man?"

The AI's response—listing everything from earning more money to having faster access to "power rooms"—pissed her off, but also activated a plan. Laura breaks down the five core areas where women are often held back and details the specific, gutsy move she attached to each one, creating a powerful blueprint for other women to follow.

Tune in for:

• The exact list of biases ChatGPT revealed, including:
  • Earning more money (complete with stat ranges).
  • Access to more power rooms.
  • Boldness being seen as confidence, not a risk.
  • Outsourcing and delegating faster.
  • Less self-questioning.
• Laura's five "healthy spirals"—a practical, gutsy move for each bias to help women close the gap.
• Why "pitching full price" is the first gutsy move you need to make to fund outsourcing and regain your time.
• The power of "creating the room" or simply showing up in spaces like you belong there.
• The surprising secret to showing up as your full, bold self on platforms like LinkedIn (hint: it involves getting raw and authentic).
• The best advice for overcoming analysis paralysis and the constant urge to overthink your next step: "Do one thing."
• How to use your "evidence bank"—a track record of your past accomplishments—to eliminate self-questioning and own your worth.

About Laura Aura:

LauraAura is a speaker, brand strategist, and the host of The Gutsy Podcast, where she encourages thousands of women to stop overthinking and start doing the thing they can't stop thinking about. She is known for her bold, direct, and deeply encouraging approach to female ambition.

Resources & Links:

• Listen to The Gutsy Podcast:https://lauraaura.com/the-gutsy-podcast/
• Follow LauraAura on Instagram & TikTok: @thatLauraAura
• Amplify with Jess is produced by Walk West and brought to you by Mic Drop Workshop.

Visit walkwest.com to see more!

The world is constantly in a state of chaos—from an unexpected crisis at work to the personal high stakes of having a baby during a global pandemic. How do you find the calm confidence needed to navigate those moments when you feel most exposed?

This week on Amplify, Jess sits down with Caitlin Gardner, a veteran crisis communications expert who is the founder of Blooming Communications. Caitlin's professional life involves helping Fortune 500 companies communicate with calm maturity during crises. Her personal life, however, includes having a baby at the peak of the 2020 pandemic while her husband lost his job—a high-stakes moment that uniquely prepared her for the work she does today.

Caitlin shares how to apply the lessons learned in the delivery room to the boardroom, giving you the practical tools to handle unexpected public scrutiny, internal high stakes, and even the double-edged sword of going viral.

Tune in for:

• Caitlin's incredible story of delivering a baby in April 2020, juggling a crisis communications job in the hard-hit cruise industry, and the power of focusing on one goal in a chaotic environment.
• The concept of the "Reputation Bank Account": making positive deposits so you have the benefit of the doubt when you need to make a withdrawal (like when you fumble publicly).
• The difference between good-intentioned feedback and negative trolling, and the importance of assuming good intent in professional communications.
• Caitlin's take on cancel culture, and why brands and people must define their core values to maintain clarity in polarizing times.
• Why it’s essential to be prepared for the worst-case scenario (the "tabletop exercise") so you can be agile and confident when chaos hits.
• How to handle the urge to jump on viral trends and why every piece of content—even your social media hook—needs a strategic rationale and intentionality.
• A key reminder for leaders: You don't get to choose when the stakes are high for others, so be thoughtful about how you deliver high-stakes feedback.

About Caitlin Gardner:

Caitlin Gardner is the Founder of Blooming Communications, a strategic communications consultancy. She is an expert in high-stakes communications, reputation management, and crisis preparedness, helping clients bring "calm confidence" to moments of unexpected chaos.

Resources & Links:

• Follow Caitlin Gardner on LinkedIn: https://www.linkedin.com/in/caitlingardner/
• Blooming Communications: https://bloomingcom.com
• Amplify with Jess is produced by Walk West and brought to you by Mic Drop Workshop.

Visit walkwest.com to see more!

Have you ever confused a bigger salary with a richer life? What if the key to getting what you truly want isn’t a better tactic, but a deeper understanding of your own values?

 In this Amplify episode, Jess sits down with negotiation expert Kathryn Valentine, a former McKinsey consultant with an impressive background featured in Harvard Business Review and The Wall Street Journal. Kathryn's journey started with a high-stakes failure—a negotiation so bad it ended with a security escort. Still, that experience led her to discover that proper negotiation is a valuable tool for life design, not just a means to secure a salary bump.

Kathryn reveals how to identify your true currency (it’s often not money), the critical research that proves women significantly underestimate their market value, and the simple questions you can ask to strip away societal expectations and define your own "rich life."

Tune in for:

• The shocking story of Kathryn’s first negotiation attempt that ended in her being escorted out of a large company.
• The "Rich Life Design" concept: how seeing the long-term impact of choices from her 70-year-old grandparents taught her to prioritize currencies like time, credibility, and autonomy.
• What you really want is often a promotion (for long-term financial gain) or credibility (for respect), not just a raise.
• The "Magic Wand" question helps strip away fear and societal expectations, revealing what you truly want.
• The "Ask Relationally" formula that virtually eliminates the risk of backlash and moves "no" from a rejection to a piece of information.
• Why assuming good intent is the key to overcoming the fear of being "annoying" when following up.
• Kathryn's personal thoughts on how motherhood has changed her perspective over time and why she now chooses to pursue only projects that bring her "good exhaustion."

About Kathryn Valentine:

Kathryn Valentine is a negotiation expert, speaker, and former McKinsey consultant. Her work has been featured in the Harvard Business Review and The Wall Street Journal, and she advises companies such as JPMorgan Chase. She is dedicated to equipping women with the tools to negotiate for their richest life.

Resources & Links:

• Get the "76 Things You Can Negotiate" List: https://seventysixthings.com
• Watch Kathryn Valentine's TED Talk:
• Follow Kathryn Valentine on LinkedIn: https://www.linkedin.com/in/kathrynvalentine/
• Amplify with Jess is produced by Walk West and brought to you by Mic Drop Workshop.

Visit walkwest.com to see more!

Have you ever questioned if you should quit your career to focus on family, only to realize that constant self-doubt is draining energy you could use elsewhere? What if continuing to work is not just a financial necessity, but a vital investment in your own identity?

This week on Amplify, Jess sits down with Hazel Sy, a Fortune 500 executive, board member, and powerful advocate for working parents. Hazel shares the moment her childcare plan fell through, the panic and guilt that followed, and the eventual mindset shift that allowed her to thrive as both a dedicated professional and a devoted mom.

Hazel opens up about the emotional journey of creating her viral TED Talk, the shocking financial reality of childcare, and the surprising ways that conscious parenting techniques can make you a more intentional and connected leader at work.

Tune in for:

• Hazel's eye-opening story of her childcare falling through and the constant question she asked herself: "Should I quit?"
• Why the high cost of childcare is actually a financial and personal investment that pays off in career growth and a preserved sense of self.
• The "mother AND" philosophy: how to choose a parenting style where your children see you succeeding and failing, not just staying home.
• The subtle societal double standards around working parents, including the "babysitting" comment and the different applause men and women receive.
• How Hazel consciously uses the word "study" instead of "work" around her children to avoid modeling a workaholic lifestyle.
• The emotional journey of getting 67 rejections before landing her TEDx Talk, and the critical moment when she decided to scrap all the feedback and write from the heart.
• How the skills of conscious parenting—like giving two choices instead of a demand—make you a better leader and influencer in the workplace.

About Hazel Sy:

Hazel Sy is a Fortune 500 executive, a board member, a highly requested speaker, and an alumnus of Mic Drop Academy. She is a passionate advocate for working parents and a living example of how intentionality and purpose can allow you to thrive in both your professional and personal life.

Resources & Links:
Watch Hazel's TED Talk: https://www.youtube.com/watch?v=YE-PN4i-eAE

• Find Hazel's Speaker Prep Checklist:
• Follow Hazel Sy on LinkedIn: https://www.linkedin.com/in/thehazelsy/
• Visit Hazel Sy's site: https://www.hazelsy.com/ 
• Amplify with Jess is produced by Walk West and brought to you by Mic Drop Workshop.

Visit walkwest.com to see more!

Have you ever secretly loved being underestimated? That feeling of having nothing to lose and everything to prove. But what happens when you start to succeed, and that pressure of being watched threatens to sabotage your progress?

This week on Amplify, Jess sits down with her dear friend, author, and speaker Mary Marantz, whose new book Underestimated explores how to break free from the fears that hold us back. Mary gets candid about her journey, from being told by a high school teacher that she wouldn't make it, to the destructive cycle of perfectionism and self-sabotage that comes with success.

She shares how she's learned to embrace a new kind of fuel for her ambition and why she believes the very act of facing fear means you're about to do work that truly matters.

Tune in for:

• Why being an underdog is a "role of a lifetime" that can destroy your ambition if you aren’t careful.
• The surprising connection between childhood chaos and the urge to self-sabotage as an adult.
• The "Motivation-Defeat Cycle" and how to break free from the all-or-nothing mindset.
• Why consistency will always beat excellence in the long run.
• Mary’s powerful reframe: Fear isn't a creative force; it's a "boring liar" that uses the same broken scripts on everyone.
• How to identify your "achiever type" and use that knowledge to overcome your unique fears.
• The truth about asking for help and why we’re often our own worst enemies when it comes to showing vulnerability.

About Mary Marantz:

Mary Marantz is an author, speaker, and entrepreneur whose work empowers people to unlock their purpose and do the work they were put on this earth to do. She is a New York Times bestselling author of Dirt and Slow Growth Equals Strong Roots, and her newest book is titled Underestimated.

Resources & Links:

• Get Mary's free first chapter and Achiever Quiz: https://namethefear.com
• Follow Mary Marantz on Instagram: https://www.instagram.com/marymarantz/
• Follow Mary Marantz on LinkedIn: https://www.linkedin.com/in/mary-marantz-726461b/
• Listen to the Mary Marantz Show: https://podcasts.apple.com/us/podcast/the-mary-marantz-show/id1454133596
• Amplify with Jess is produced by Walk West and brought to you by Mic Drop Workshop.

Visit walkwest.com to see more!

Amy Porterfield really wanted freedom, flexibility, and autonomy in her career.

She entered the digital course industry, which allowed her to work from home while still making money. Starting small, her first course made just $267, but she pulled in over $100 million in revenue through tweaks and relaunches.

How did she do it?  How can you leverage digital courses to balance work and family life and generate income while being present for your family?

Let's find out!

And if you’re ready to take the first steps yourself, Amy is breaking it all down inside her brand-new Course Confident Bootcamp. Over 5 days, she’ll walk you through 4 simple steps to turn your talk or story into a course—without the overwhelm.

It all starts September 11.

👉 Join Course Confident for $47

This is a replay from Aug 28th, 2024. 

---

Rate Amplify on Spotify and Apple Podcasts and leave a review for Jess Ekstrom.

Amplify with Jess is produced by Walk West, and brought to you by Mic Drop Workshop

Visit walkwest.com to see more!

Have you ever felt like you're not what meets the eye, with a deep, complex backstory hidden behind a seemingly successful exterior? What if the most difficult parts of your past, the ones you tried to escape, are actually the secret ingredients to your greatest triumphs and your most powerful message?

This week on Amplify, Jess sits down with Adam Tanaka, a founder and speaker who has built and sold companies and now teaches others how to unlock their most creative selves through the power of play. Adam's journey is far from linear and his seemingly picture-perfect success story is built on a childhood filled with trauma and chaos, where a game of hide and seek was an act of survival.

He opens up about his "normal," which included a mother struggling with addiction, his heroic act of saving her from a house fire at age 15, and how that trauma unknowingly followed him into adulthood. Adam shares how his success led to one of his darkest moments, what truly saved his life, and the powerful framework he created to ensure he and others always have a community to fall back on.

Tune in for:

• The childhood trauma that led Adam to seek control and stability by building his own businesses.
• How Adam learned to stop waiting for permission to play and why he believes play is a crucial tool for both creativity and healing.
• The moment a sheep farmer in Iceland changed Adam's perspective on overcomplicating life and rigid goals.
• The importance of building your community before you need it.
• The "Community Tag" framework, a powerful and simple system for checking in on those around you that Adam created after a near-fatal moment.
• Why Adam's mission as a speaker is to help people bring play into the workplace and life.

About Adam Tanaka:
Adam Tanaka is a founder, speaker, and advocate for the power of play. With a background in building and selling companies, Adam's mission is to help people move from rigid, "hustle culture" to a more creative and connected way of working and living. He is the founder of a kids' brand, cavehousesupply.com, and an author.

Resources & Links:

• Cave House Supply: https://cavehousesupply.com
• Adam Tanaka's Website: https://adamtanaka.com
• Follow Adam Tanaka on LinkedIn: https://www.linkedin.com/in/adam-tanaka-7b43a85b/
• Amplify with Jess is produced by Walk West and brought to you by Mic Drop Workshop.

Visit walkwest.com to see more!