Your Unstuck Era: Career Change, Side Hustles & Entrepreneurship

Your Unstuck Era
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Your Unstuck Era is an operator podcast about how businesses get built before the success story is obvious. Host Vivian Ly interviews early-stage founders, including the person sitting next to you at the office who is quietly building an entire company, to unpack the decisions, experiments, economics, and tradeoffs behind the build. No celebrity origin stories or billion-dollar hindsight. Just useful conversations with people close enough to the beginning to tell you how it actually works.

  1. 2d ago

    12. Cara Lash: Building a NYC Day-Trip Company While Working in Consulting & Landing Brand Partnerships Like Free People

    How do you know when to keep going with an idea, and when to let it become something else? Cara Lash is the founder of Caravan, a modern day trip company for busy New Yorkers who want an elevated escape: breakfast in the park, a bus out of the city, a hike, then a farm or winery. She built it alongside her consulting job, and about a year in, her trips sell out within seconds of launch. But the first trip involved a janky bus and a lot of begging friends and family to come along. And before Caravan, there were three years spent building a different business. What drew me to Cara’s story is the uncertainty behind something that now looks like an obvious idea. When you care deeply about what you’re building, how do you tell the difference between something that needs more time and something that needs to change? In this episode, we get into the decisions that led her to Caravan, how she designs a day people remember, and what it takes to get brands to partner with a young business. We also explore how she’s finding opportunities to grow beyond selling individual tickets, while still working her consulting job. For anyone turning a passion into a business, questioning their original plan, or wondering where their next opportunity might come from, this is a conversation about staying open to what you discover once you start. (00:00:00) What Does It Take to Walk Away From Three Years of Work?(00:01:12) What Was Plan A Before Caravan?(00:03:17) Why Did Cara Keep Building for Three Years?(00:04:44) What Made Her Flip the Switch?(00:05:53) What Did the First Trip Out of the City Look Like?(00:08:28) Where Did Her Love of the Outdoors Come From?(00:10:23) What Does the Travel Industry Get Wrong?(00:11:36) How Do You Get Strangers to Connect on a Hike?(00:14:42) How Big Is the Brand and Corporate Side of the Business?(00:16:05) How Did the First Big Brand Find Her?(00:19:04) What Do You Charge When You Have No Case Studies Yet?(00:21:25) What Did Brands Care About That She Didn't Expect?(00:22:24) How Did She Know When to Leave Consulting?(00:26:18) How Do You Build a Network Before You Need It?(00:28:19) What Advice Changed How She Runs the Business?(00:29:40) What Is the Next Big Bet?(00:30:12) How Do You Go for the Full Bet, Not a Baby One?(00:30:58) Where to Find Caravan Resources & Links: Explore Caravan→ Visit caravantripplan.com→ Follow @caravantripplan on Instagram and join an upcoming trip Connect with Cara→ DM @caravantripplan on Instagram or connect with Cara on LinkedIn Follow Your Unstuck Era→ @yourunstuckera for more stories from people building something of their own Enjoyed this episode?Share it with a friend, leave a review, or tag us on IG. Your support helps this show reach more people who are ready to get unstuck and build something of their own. Chapters

  2. Sep 29

    11. Mary Bemis: Selling Non-Toxic Activewear Years Before Anyone Believed They Needed It

    Mary Bemis spent eight years building Reprise Activewear, a non-toxic activewear brand, while working full-time in advertising. This year the business grew 4x, closing in on its first seven-figure year. But growth wasn't guaranteed. For years, Mary had the mission right and the positioning wrong — a message that made sense to her but didn't move anyone to buy. COVID very nearly ended the business before it had a real chance, and for a long stretch, being early didn't feel like an advantage. In this episode, we unpack what it actually takes to build a mission-driven brand years before the market is ready to care, how Mary kept going through a stretch that didn't reward her for being right, and the numbers behind an eight-year "overnight success." In this episode, we talk about: Why her positioning, not her mission, was the real obstacle for years What happened when Reprise's factories stopped making her product overnight How eight years of staying the course turned into a 4x year How to keep believing in a mission before the market is ready to pay you back for it This is a conversation about building something you believe in before the world agrees it matters, and what it takes to stay in the game long enough for that to pay off. (00:00:00) Intro(~00:00:30) Who Is Mary Bemis, and Why Has Reprise Activewear Suddenly Taken Off?(~00:01:30) What Made Her Quit a Finance Job With Nothing Lined Up?(~00:03:30) What Did the First Version of Reprise Actually Look Like?(~00:05:30) Why Didn't Talking About Microplastics Actually Sell Leggings?(~00:11:00) What Does "Non-Toxic" Actually Mean, and How Do You Prove It?(~00:14:30) What Did She Wish She'd Understood About Her Margins Sooner?(~00:17:30) How Do You Keep Selling When Your Factories Stop Making Your Product?(~00:21:30) What Was the Signal That Told Her It Was Finally Time to Go Full-Time?(~00:23:00) How Did Reprise Respond to the Lululemon PFAS News?(~00:24:30) Why Does Email Outperform Social for Reprise?(~00:26:00) What Is Reprise Still Trying to Figure Out?(~00:28:00) What Would She Tell a Founder Ready to Give Up Too Soon?(~00:29:15) Where to Find Reprise Activewear Resources & Links: Explore Reprise Activewear→ Shop Reprise Activewear: repriseactivewear.com→ Follow @repriseactivewear on Instagram Connect with Mary→ DM @repriseactivewear — Mary reads these herself and personally connects with listeners there. Follow Your Unstuck Era→ @yourunstuckera for more stories from people building something of their own Enjoyed this episode?Share it with a friend, leave a review, or tag us on IG. Your support helps this show reach more people who are ready to get unstuck and build something of their own. Chapters

  3. Sep 10

    10. Hibi Chan: Building a Luxury Skiwear Brand Alongside Your 9-5 Without Losing Yourself

    Hibi Chan launched Vallesoir to bring the glamour of vintage ski style back to the slopes without the traditional luxury price tag. Within weeks, boutiques in Vail and Aspen found the brand and placed orders. But behind those early wins was a much messier first season. Tariffs nearly stopped the launch, inventory assumptions proved wrong, and building the business began to change Hibi in ways she hadn’t anticipated. In this episode, we unpack what it actually costs to build a fashion brand, why Hibi is willing to give herself five years to make it work, and the moment she realized chasing growth was pulling her away from the reason she started. In this episode, we talk about: • How Vallesoir landed retailers in Vail and Aspen• The inventory mistake that reshaped how Hibi understands her customer• Why she gave herself a five-year runway to build the brand• How to pursue an ambitious dream without losing yourself in the process This is a conversation about betting on yourself, learning through action, and deciding what you are willing to sacrifice without sacrificing who you are. (00:00:00) Intro(00:01:28) What the Ski Industry Gets Wrong About Women(00:02:43) Bringing Back the Golden Age of Ski Style(00:03:18) Cutting Open a Vintage Sweater to Understand Its Construction(00:04:21) Why Each Vallesoir Sweater Takes Eight Extra Hours to Make(00:05:02) The First Purchase Orders From Vail and Snowmass(00:06:31) How SEO Helped Boutiques Discover the Brand(00:07:03) Wholesale vs. E-Commerce(00:07:27) The Meta Ad That Generated Her First Sale(00:10:06) The Not-So-Glamorous Side of Building a Fashion Brand(00:10:51) When Tariffs Nearly Stopped the Launch(00:11:33) Why Hibi Launched Into an Uncertain Market Anyway(00:12:29) Refusing to Pass Tariff Costs Onto Her Customers(00:14:24) The Inventory Mistake She Would Never Repeat(00:16:45) Why She Gave Herself Five Years to Make It Work(00:18:04) Treating the Business Like Her Version of Business School(00:19:19) The Personal Sacrifices Behind Funding the Brand(00:21:07) What Building Vallesoir Changed in Her(00:21:42) When Chasinglomer Virality Stops Feeling Like You(00:24:24) Remembering Who You Are Building For(00:26:43) Why Off Piste Became Vallesoir(00:28:42) The Person Hibi Wants to Be Four Years From Now(00:30:12) Where to Find Vallesoir Resources & Links: Explore Vallesoir→ Shop Vallesoir→ Follow @vallesoir on Instagram Connect with Hibi→ @hibieatssushi on Instagram Follow Your Unstuck Era→ @yourunstuckera for more stories from people building something of their own Enjoyed this episode?Share it with a friend, leave a review, or tag us on IG. Your support helps this show reach more people who are ready to get unstuck and build something of their own. Chapters

  4. Aug 27

    9. Belen Tenorio: Why a Spotify Design Lead Left to Build the Spotify Wrapped for Journaling

    Belen Tenorio helped design Spotify Wrapped, one of the most anticipated product experiences of the year. Now she’s using that same instinct to reveal patterns in how we think. Before Pillowtalk, Belen built an AI startup that made it to the Y Combinator interview stage. She ultimately chose not to pursue it. In this episode, we unpack why a promising idea is not always the right company to build and how to recognize when you have found something worth committing to. Pillowtalk began as a personal solution to Belen’s insomnia. But once people started using it, their behavior revealed a possibility she had not anticipated. Following that signal changed the direction of the product and the larger vision behind it. It has also become one of the rare examples I’ve seen where AI and human connection are designed to support each other. In this episode, we talk about: • Why Belen walked away from an idea that reached a Y Combinator interview• How to recognize whether an idea is actually worth building• The launch strategy that generated 30,000 app preorders without paid marketing• How to design around emotion and human connection This is a conversation about following the signals people give you, designing for how you want someone to feel, and imagining technology that brings us closer to ourselves and one another. Chapters (00:00:00) Intro (00:01:00) From Pro Tennis To Apple, Nike & Spotify: Belen's Design Career (00:02:00) What Is Pillow Talk, Really? (00:03:00) The Two-Year Insomnia Battle That Sparked The Idea (00:04:00) Building The First Version — Just For Herself (00:05:00) When Does A Personal Tool Become A Company? (00:06:00) Convincing Her Co-Founder To Quit Her Job (00:07:00) The Startup She Walked Away From — And Why (00:09:00) The Real Signal: Friends Sharing It Without Being Asked (00:10:00) The App Store Trick Behind A 30,000-Person Waitlist (00:11:00) Beating Strava, Whoop & Oura To #1 (00:12:00) The Unbranded Social Experiment That Went Viral (00:13:00) How Many User Interviews Do You Actually Need? (00:15:00) "We Used To Be A Society, Now We Are A Network" (00:17:00) Can AI Actually Help You Feel Less Alone? (00:18:00) A Concrete Example: The New-Parent Identity Crisis (00:20:00) The Design Principle Behind Every App She's Built (00:21:00) Pinterest vs. Nike: How Color Creates Feeling (00:22:00) The James Turrell Installation That Shaped Pillow Talk (00:23:00) Inside The "Yep" Feature: Designing For 2am (00:25:00) Designing Through A Female Gaze vs. A Male-Centric One (00:26:00) "Designing For The Corners" (00:27:00) Is Pillow Talk Reading Your Diary? How Building This App Changed Her (00:29:00) Where To Download Pillow Talk & What's Next With Circles Resources & Links: Find your people with Pillowtalk Circles→ Join the waitlist Explore Pillowtalk→ Download the app→ Visit the website→ Follow @talkpillowtalk on Instagram Connect with Belen→ Instagram→ LinkedIn Follow Your Unstuck Era→ @yourunstuckera for more expander stories, bold pivots, and behind-the-scenes moments Enjoyed this episode?Share it with a friend, leave a review, or tag us on IG. Your support helps this show reach more people who are ready to get unstuck and build something of their own.

  5. Jan 20

    8. What Actually Builds Real Founder Confidence When You’re Figuring It Out as You Go, with Louisa Li of Shanti House

    Founder confidence does not come from clarity. It comes from action. Louisa Li spent nearly a decade at BCG before leaving to build Shanti House, a profitable, community-first wellness events business. In its first year, she launched over 50 events and is redefining how founders connect and build real relationships in what can often be a highly transactional city. This episode explores how confidence is built in real time when there is no roadmap, no external validation, and no guarantee you are doing it right. This conversation is not about walking away from corporate life with certainty. It is about what happens when you leave structure behind and have to build self-trust from scratch. After traveling to Bali, completing her yoga teacher training, and reconnecting with her intuition, Louisa returned to New York and began experimenting. She hosted small wellness gatherings. Tested ideas in real time. Paid attention to what worked and what didn’t. Over time, those experiments evolved into Shanti House. In this episode, Louisa shares what she learned along the way: What actually builds real founder confidence when you’re figuring it out as you go Why confidence is a byproduct of action, not clarity How intuition becomes a practical tool when there is no playbook The behind-the-scenes reality of building a profitable wellness events business Why founders need spaces rooted in presence, not performance How to balance passion with practicality while still trusting yourself This is the story of how a wellness events business was built and evolved in real time. It is not a story about having it all figured out. It is a grounded look at how confidence is built through repetition, experimentation, and staying in the arena long enough to believe in yourself. Since this conversation was recorded, Louisa has launched Urban Iron in Austin, and Shanti House has entered a new chapter with plans for a physical space to house its events and deepen its community. Resources & Links:Connect with Louisa  →  On Instagram Learn more about Shanti House Follow Your Unstuck Era:  → @yourunstuckera for more expander stories, bold pivots, and behind-the-scenes moments Enjoyed this episode?Share it with a friend, leave a review, or tag us on IG. Your support helps this show reach more people who are ready to get unstuck and come home to themselves. Timestamps: 00:00 Introduction to Louisa Li and Why This Story Matters 01:01 From BCG to Wellness: Louisa’s Corporate Foundation 01:37 The First Experiment: Hosting a Fitness Event 04:03 Leaving Structure Behind and Stepping Into Entrepreneurship 04:58 Discovering Yoga, Spirituality, and Intuition 13:11 What Actually Builds Real Founder Confidence 19:34 Launching Shanti House 23:35 The Highs and Lows of Building in Public 26:30 Learning Through Mistakes and Course-Correcting 28:22 Shanti House Takes Shape 29:18 Growing from Yoga Classes to Full-Scale Events 30:09 Monetization, Profitability, and Expansion 31:45 Navigating the Founder Ecosystem in a Transactional City 33:56 Balancing Passion with Practicality 41:12 Staying Resourceful While Scaling 45:35 Why Real Connection Is the Foundation of Community

  6. 10/16/2025

    7. 3 Why a Former Amazon Product Exec Left to Co-Found the Strava of Creativity

    What if the path back to feeling alive wasn’t about doing more, but about creating space to play again? After nearly a decade leading product at Amazon, Lakshmi Narayanee began to question what success was costing her. What started as a short mental health break became a ten-month sabbatical in Bali that sparked a deep exploration into what makes people feel alive. Through creative experiments like failure parties, blind drawing circles, and idea jams, she began to rediscover her spark — and what it truly means to build with joy instead of burnout. Those experiments became the foundation for NoomaLooma, the “Strava of creativity,” a platform designed to help people practice creativity in small, everyday moments that fit the rhythm of real life. In this final chapter of the series, we cover:  • How Lakshmi met her co-founder and defined their shared mission • What it takes to build a community-driven company from the ground up • Why creativity is the key to accessing untapped ideas and energy • How to build daily creative rituals that fit your lifestyle • How to spark creativity in under two minutes This episode closes the arc of untethering, experimenting, and finally building — turning inner transformation into something tangible. It’s a reminder that creativity isn’t reserved for artists. It’s how we reconnect with ourselves, one small act of creation at a time. Resources & Links:Connect with Lakshmi  →  On Linkedin →  On Instagram Learn more about NoomaLooma → Join the waitlist Follow Your Unstuck Era:  → @yourunstuckera for more expander stories, bold pivots, and behind-the-scenes moments Enjoyed this episode? Share it with a friend, leave a review, or tag us on IG. Your support helps this show reach more people who are ready to get unstuck and come home to themselves.

  7. 10/10/2025

    7.2 How to Use Design Thinking to Build What’s Next with an Ex-Amazon Product Exec

    What if the next version of your career wasn’t built alone but co-created with the people around you? Lakshmi Narayanee built her career scaling some of the world’s most recognizable products. But what she’s building now looks entirely different. During her ten-month sabbatical in Bali, Lakshmi began using design thinking to explore not just products but people, community, and purpose. She started hosting failure parties, idea jams, and gatherings that helped others connect more deeply and see their own possibilities through shared experience. What started as a pause became a blueprint for how to design your next chapter with curiosity instead of certainty. In the second part of this four-part series, Lakshmi shares how to: • Apply design thinking to your own life to make better career decisions faster • Use community as a mirror to uncover blind spots and surface new directions • Turn failure into data and use it to design smarter experiments • Prototype ideas in real life before committing to a full pivot • Build systems for creativity and connection that spark opportunity This is a masterclass in using design to live with more intention and proof that sometimes, the best way forward is to build it together. In our next episode, we take design thinking a little further and talk about how you can use it and AI to become your company’s design partner. Resources & Links:Connect with Lakshmi  →  On Linkedin →  On Instagram Learn more about NoomaLooma Follow Your Unstuck Era:  → @yourunstuckera for more expander stories, bold pivots, and behind-the-scenes moments Enjoyed this episode?Share it with a friend, leave a review, or tag us on IG. Your support helps this show reach more people who are ready to get unstuck and come home to themselves.

  8. 10/06/2025

    7.1 What It Really Looks Like to Take a “Slow-Battical” with Lakshmi Narayanee

    How do you structure an effective break to figure out what you want to do next? Lakshmi Narayanee comes from a traditional background in India and built what many would call a dream career. As a product executive at Amazon, she spent more than a decade helping launch Amazon in India, expanding Amazon Prime into emerging markets, and becoming the kind of manager people dream of working for. She had massive impact, loved the work, and was genuinely lit up by it. Until the path stopped sparking curiosity and came to a halt. By her own words, Lakshmi was a “certainty mongerer”, someone who thrived on plans, structure, and knowing exactly what came next. Which is why her decision to pause was so striking. What began as a ten-week break stretched into ten months. She booked a one-way ticket to Bali, gave herself space to pause, and started testing what life could look like without the scaffolding of Big Tech. Along the way, she found a framework that helped her name exactly what was happening and why her old definition of success no longer fit. In this first part of a four-part series, Lakshmi shares practical insights from stepping away: ​How to know when it is time to take a break (even if you love your job) ​The difference between a vacation and a sabbatical that actually creates clarity ​Why identity can keep us tied to roles past their expiration date ​How to use liminal space, the in-between, as a tool for alignment ​What Bali and teaching children revealed about presence and play This is not an Eat, Pray, Love fantasy. It is the real-world version of what it looks like when a Big Tech product executive and self-described certainty mongerer pauses to ask: What’s next? Resources & Links:Connect with Lakshmi  →  On Linkedin →  On Instagram Learn more about NoomaLooma Follow Your Unstuck Era:  → @yourunstuckera for more expander stories, bold pivots, and behind-the-scenes moments Enjoyed this episode?Share it with a friend, leave a review, or tag us on IG. Your support helps this show reach more people who are ready to get unstuck and come home to themselves.

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Your Unstuck Era is an operator podcast about how businesses get built before the success story is obvious. Host Vivian Ly interviews early-stage founders, including the person sitting next to you at the office who is quietly building an entire company, to unpack the decisions, experiments, economics, and tradeoffs behind the build. No celebrity origin stories or billion-dollar hindsight. Just useful conversations with people close enough to the beginning to tell you how it actually works.

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