Pickles & Pasta with Steph and Jay

Welcome to Pickles & Pasta , a podcast about living creatively, loving boldly, and staying grounded in a world that often feels anything but. Steph and Jay met (or as Jay says “reconnected”) just before the pandemic and have been building a life, and a creative partnership, ever since. Together, they live, work, and support each other’s ventures while navigating the messy, beautiful chaos of modern life. No agendas. No sides. Just real conversations,sometimes deep, sometimes hilarious, always honest. This is their space to talk about creativity, connection, relationships, and everything in between. Pull up a chair. Let’s dig in. About Steph Stephanie Rado Taormina is the CEO and founder of Have Some Fun Today, a lifestyle brand inspired by her late father's mantra to live boldly and joyfully. With over 25 years of experience in branding, fashion, interiors, and entrepreneurship, she brings a sharp creati

Pickles & Pasta with Steph and Jay is a arts podcast hosted by Steph, with 54 episodes on record and a Required Pod Score of 80. PitchCentric scores this show on Booking Probability, Listen Score, and live audience signals refreshed every 24 hours.

Steph hosts Pickles & Pasta with Steph and Jay, a arts show with 54 episodes published.

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  Pickles & Pasta with Steph and Jay

  What "Making It" Actually Looks Like (And Why It Never Feels Like Enough)

  Aug 20, 202648 min

  What does "making it" actually feel like once you think you've arrived? In this episode of Pickles & Pasta, Steph and Jay dive into one of the most misunderstood aspects of creative and entrepreneurial life: the disconnect between how success looks from the outside and how it feels on the inside. Steph shares her journey, from graduating from Parsons to working as a designer at Andrew Marc, launching Have Some Fun Today—a brand that unexpectedly caught the attention of A-list celebrities like Halle Berry and Mila Kunis—and transitioning into fine art, with her paintings showcased in public works at the GoggleWorks. Despite magazine covers, celebrity endorsements, and gallery recognition, she reveals why none of it has ever truly felt like "making it." Instead, she discusses why she defines success by financial independence and staying true to herself. Jay offers a different perspective, recounting his own career highlights, from earning a spot on the U.S. Davis Cup team through sheer determination, to working with Andre Agassi, to being featured on HBO and in Sports Illustrated. He reflects on why external recognition rarely aligns with the internal satisfaction of achievement. Their conversation takes a philosophical turn as they explore whether "making it" is defined by financial milestones, public perception, or quieter achievements like raising great kids, doing meaningful work, or helping others in small but impactful ways. Along the way, they examine Taylor Swift's billionaire status as the ultimate case study, how people's behavior shifts once you're perceived as successful, and Jay's long-term vision for Village. This episode explores: The "moving goalpost" phenomenon and why dedicated creatives constantly redefine what "making it" means The difference between feeling successful and being seen as having "made it" by others Why financial success, more than critical acclaim, is often the cultural marker of "arriving" How people's attitudes toward you change when you're perceived as successful, even if you feel the same The Davis Cup story: earning a spot on the U.S. team through an unplanned trip to Mexico Why Steph considers raising her daughters her greatest accomplishment, more than any career milestone Why Jay doesn't see Village as his "making it" moment, even as it reshapes the industry The idea that helping others in simple, unglamorous ways might be the truest form of success And more! Takeaway: "Making it" isn't a fixed destination—it's a goalpost that keeps moving for those who are passionate about their work. True success might not be about accolades at all; it could be about showing up for others in small, meaningful ways every day. Subscribe so you never miss an episode of Pickles & Pasta, and share this with someone who's still waiting to feel like they've "made it." Chapters 0:00 Cold Open 0:33 Welcome to the Show 1:16 What Does "Making It" Really Mean? 3:16 Steph's Career Journey & the Moving Goalposts 10:53 Is Money the Real Measure of Success? 15:05 Why Overachievers Never Feel Done 17:03 A Friend Who Truly "Made It" 19:55 How Fame Changes the Way People Treat You 21:40 Taylor Swift & Undeniable Success 22:50 Steph's Real Proudest Achievement 26:40 Single Motherhood & Authentic Art 32:22 Jay's Tennis World Milestones 34:53 Building Village: Redefining Success 40:50 The Power of Helping Others 45:32 Closing Thoughts Learn more about your ad choices. Visit megaphone.fm/adchoices

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  Pickles & Pasta with Steph and Jay

  Creative Identity Isn't Built Alone: The Relationships Behind the Work

  Aug 13, 202646 min

  How much of your creative identity is shaped by the people in your life? In this episode of Pickles & Pasta, Steph and Jay explore the ways relationships—family, romantic, professional, and social—influence an artist's confidence, identity, and body of work. Steph reflects on her artistic roots, growing up as the eldest grandchild in a large Italian family, where early encouragement for her creativity became a cornerstone of how she viewed herself. She and Jay discuss a pattern many creatives will recognize: being praised for artistic talent as a hobby, but subtly discouraged from pursuing it as a career—often by family members who equate responsibility with financial stability rather than creative risk. The conversation deepens as Steph shares how embracing a more public and evolving creative identity on social media after her divorce came at a cost—some relationships she once relied on became strained. She talks about the impact of being confined by others' expectations and the personal and artistic transformation that followed when she broke free of those constraints. Jay offers an outside perspective, highlighting Steph's resilience and her unwavering commitment to painting, regardless of external validation, as key to the growth evident in her recent work. Together, they delve into the role of environment, physical space, and community in shaping an artist's process, and why gratitude—even if it takes years to emerge—can profoundly impact both the art and the artist. This episode explores: How early encouragement in childhood can shape creative identity for a lifetime The family dynamic of celebrating art as a hobby while discouraging it as a career Reinventing yourself creatively and navigating public scrutiny after a major life event, like divorce Why true self-worth comes from knowing yourself, not from likes, followers, or external approval The influence of environment and physical space on an artist's work How to identify relationships that fuel your creativity versus those that drain it The connection between resilience, gratitude, and long-term creative growth And more! Takeaway: Creativity doesn't happen in isolation. The people in your life either nurture your creative work or hold it back—and learning to tell the difference is one of the most valuable skills you can develop. Subscribe to Pickles & Pasta so you never miss an episode, and share this with someone who might be limiting their creativity to meet the expectations of others. Learn more about your ad choices. Visit megaphone.fm/adchoices

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  Pickles & Pasta with Steph and Jay

  The Internet Isn't Your Therapist

  Aug 6, 202645 min

  Is sharing your creative journey online an act of courage, or a cry for help? This week, Steph and Jay dig into one of the most debated questions in the creator economy: should you build in public? Steph traces her own start back to 2008, posting as an interior designer, painter, and newly single mother in a small town, years before "personal brand" was even a phrase, and talks about the early community pushback that taught her to pull back before she knew how to lean in. Jay, a self-described private person, pushes on the harder question underneath all of it: are you inspiring your audience, or are you using them as a therapy session? They get into why sharing your process isn't the same as oversharing your wounds, how the gatekeepers who used to decide which artists the world got to know are gone, and why Steph's rule for the comments section comes down to three phrases: block freely, engage genuinely, follow no one's rule book. This episode explores: The difference between authentic sharing and using social media as unprocessed therapy Steph's path from 2008 early adopter to visual artist building a brand before the term existed Why early pushback from her small-town community taught her about resilience and knowing your audience The artist's case for transparency: when someone buys the painting, they're buying a piece of the person who made it Jay's Life Magazine and Jackson Pollock parallel, and why the gatekeepers of discovery no longer hold the keys Building a personal content framework before you hit publish, so you know what's in and what's off limits Steph's philosophy on trolls and the block button, and why she believes creepy interactions have become rarer The Permission Effect: how one person's openness quietly gives everyone else around them permission to be brave Whether radical online transparency deepens human connection, or eventually pushes everyone back toward privacy Key takeaway: Pushback is part of the game. If you're not prepared for criticism, you're not ready to build in public. You can't eat ice cream all day and expect not to gain weight. Pick your lane, know your boundaries, and let your openness do the rest. Subscribe to never miss an episode of Pickles & Pasta, and share this episode with someone still deciding what they're willing to let the internet see. Pickles & Pasta is hosted by Steph and Jay presented by ephelants & Have Some Fun Today 00:00 Introduction – Is Building in Public Brave or Broken? 00:55 Steph's Early Social Media Journey (2008, Divorce, Small Town) 05:05 Getting Pushback for Being Ahead of the Curve 06:30 Don't Pull Back Due to the Pushback 07:30 Being Brave vs. Using Social Media as Therapy 09:49 Think Before You Post 11:10 Sharing Your Work as an Artist – Building a Personal Brand 19:53 Social Media Changed Everything for Artists 22:10 Setting Boundaries on What You Share 26:13 If You Want to Grow, You Have to Think It Through 28:21 Advice for Getting Started as an Influencer/Content Creator 33:20 Engaging with Your Audience & Handling Creepy Comments 42:35 Forming Real Bonds Through Online Openness 45:35 Accepting People Who Think Differently 43:06 Wrap-Up – Think Before You Post, Be Authentic Learn more about your ad choices. Visit megaphone.fm/adchoices

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  Pickles & Pasta with Steph and Jay

  Every Path Not Taken Still Shaped You

  Jul 30, 202643 min

  What happens to the version of you that never became reality? This week, Steph and Jay dig into a question most people avoid asking themselves: do you honor the person you used to want to be, or do you secretly resent them? Steph traces her path from advertising at Penn State to fashion design at Parsons to interior design and eventually to Have Some Fun Today, and makes the case that her core identity as a designer never actually changed, only its form did. Jay talks through his near career as a professional tennis player and the nightclub he almost opened before the funding fell through, and explains why neither path left him with any real regret. They get into the difference between regret and reflection, why creative energy is a finite resource worth protecting, and why the same piece of advice can bounce off you one year and land completely the next. Steph shares where she is six months into a self-imposed two-year plan to build a new body of work, and what it took to trust that timeline instead of rushing it. This episode explores: What it really means when a dream, career, or identity does not pan out the way you planned Steph's path from advertising to fashion design to art, and why the throughline never broke Jay's near career in professional tennis and why he has zero regrets The nightclub deal that fell apart in one conversation Why creative identity does not have to stay fixed to stay intact The difference between regret and analysis, and using the past as data instead of a wound Why the timing of advice matters as much as the advice itself Jay's ongoing tension between building custom tools and using what already exists Protecting finite creative energy while developing new work Trusting a two-year timeline instead of chasing faster, more visible output Key takeaway: The version of you that didn't make it was not a failure. It was a contributor. Every path you left, sprinkled a little magic into who you are now. Subscribe to never miss an episode of Pickles & Pasta, and share this episode with someone still figuring out what to do with the dream they let go of. Pickles & Pasta is hosted by Steph and Jay presented by ephelants & Have Some Fun Today 00:00 – Intro: The Version of You That Didn't Make It 01:30 – Do You Honor or Resent Who You Used to Be? 07:00 – Steph's Journey: From Advertising to Fashion to Design 12:00 – Not Getting "Permission" to Be an Artist 18:00 – What If the Brand Had Taken Off? (CEO vs. Creative) 24:00 – Jay's Athletic Dream & the Nightlife Path Not Taken 30:00 – Learning from Every Business & No Regrets 35:00 – Setting Timelines & Giving Yourself Grace 38:00 – Resisting Advice & Knowing When to Listen 40:30 – Closing: Letting Dreams Sprinkle Magic Into Your Journey Learn more about your ad choices. Visit megaphone.fm/adchoices

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  Pickles & Pasta with Steph and Jay

  Loving Someone Who Creates Differently Than You

  Jul 23, 202645 min

  Can two people with completely opposite ways of seeing, thinking, and creating actually build something remarkable together? This week, Steph and Jay tackle one of the most relatable challenges in creative work: collaborating with someone whose process is entirely different from your own. Steph relies on intuition, guided by feelings and visual instincts. Jay thrives on systems, driven by logistics and structure. Both see their approach as a superpower, but they admit it took trust to stop viewing the other's method as wrong. Jay introduces a baseball manager analogy to argue that the "best person for the job" isn't always the right choice. Tt's sometimes about finding someone who delivers, not just someone impressive on paper. Steph counters with the Dropbox folder moment, a humorous example of two people organizing the same project in completely incompatible yet equally valid ways. They also dive into emotions: Steph paints while crying, channeling her feelings, while Jay keeps his emotions in check to support those around him. Despite their differences, they agree on one key idea: alignment on the destination matters more than alignment on the process. This episode explores: How curiosity about someone else's process can turn friction into collaboration The contrast between Steph's intuitive creativity and Jay's systems-driven approach, and why both are essential Jay's baseball manager analogy for building a team that delivers The Dropbox folder moment and what it reveals about different yet valid perspectives How Steph and Jay handle emotions in their creative work—and why their differences complement each other Lessons from Abbott and Costello, and Lucille Ball and Desi Arnaz, on opposite creative pairings How trust allows constant disagreement without real conflict Why letting go of control (even over tea sandwiches!) can lead to better outcomes And more! Key takeaway: You don't have to create the same way to create something amazing together. Friction isn't a red flag, it's often where the best ideas are born. Subscribe to never miss an episode of Pickles & Pasta, and share this episode with someone who creates a little differently than you do! Chapters 00:00 - Intro: When Different Creative Styles Collide 01:41 - Episode Topic: Loving Someone Who Creates Differently Than You 02:43 - Curiosity as the Key to Creative Collaboration 06:56 - Jay's Superpower: Building Systems So Creatives Can Fly 09:47 - Steph's Superpower: Intuitive Vision and Creative Permission 16:28 - The Tea Sandwich Incident: A Masterclass in Letting Go 22:00 - The Balance of Great Creativity Throughout History (Abbott & Costello, Lucille Ball & Desi) 22:45 - The Baseball Manager Analogy: Right Person for the Right Moment 25:40 - What Is Your Creative Language? 36:00 - The Dropbox Folder Moment: Visual vs. Systematic Thinkers 41:09 - Trust as the Foundation of Creative Partnership 43:30 - Closing Thoughts: Be Open, Find Complementary People, Share the End Goal Learn more about your ad choices. Visit megaphone.fm/adchoices

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