Professional Jealousy Podcast: Founder Stories, Brands and Business Innovation

Natasha Jakubowski

What if you could turn career envy into your superpower? Hosted by Natasha Jakubowski, Chief Innovation Officer at Anomaly, Professional Jealousy is a business and career podcast featuring honest conversations with world-class founders, creative innovators, and industry leaders. These are the people whose success makes us wonder: What's their secret? Each episode dives deep into the realities of entrepreneurship, leadership, and personal growth. Discover actionable career advice, inspiration, and lessons from the journeys of top business minds so you can elevate your own career.

  1. Sep 8

    20,000 to 300,000 Cases: How Joey Wölffer Built a Hamptons Wine Empire

    Wölffer Estate Vineyard started on Hamptons potato fields in the 1980s, when Christian Wölffer's dream of a Long Island vineyard was such a long shot that he had to lure his own winemaker across the Atlantic with a small exaggeration — Roman was told the estate was "20 minutes from New York City." (It's closer to four hours in traffic.) The winery's first rosé, released in 1992, was so pink and so sweet that Zinfandel drinkers called it disgusting. Today, that rosé's descendant — the now-iconic Summer in a Bottle — is one of the most copied labels in wine, and the business has grown from 20,000 cases a year to 300,000. In this episode of Professional Jealousy, host Natasha Jakubowski talks with Joey Wölffer, Chief Brand Officer and co-owner of Wölffer Estate Vineyard, about the hungover, middle-of-the-night decision at 27 that led her to buy into her father's struggling business instead of selling it, how she and her brother rebuilt the brand around the "soul" of the Hamptons rather than the wine itself, and why she recently turned down an acquisition offer from a much bigger company to protect what she'd built. A Hungover Decision Not to Sell When her father died, Joey was 27, building a career in fashion, and leaning toward selling the family winery. Her mother and older brother, Marc, talked her out of it. "I remember the moment I was lying in bed — I was, to be honest, hungover," she says. "My mom and Max were like, you're not selling... you're just doing it because you think it's what's right, but in the end you'll really regret it." Marc, whom she barely knew growing up, told her, "Nothing would make me happier than being your partner." Looking back, she credits naivety as much as conviction: "If that happened to me now, no way I would have taken that chance. The business was not making money." Designing the Brand Around a Place, Not a Product Rather than starting with the wine, Joey built the brand around the Hamptons itself. "We need to make the soul of this brand the history of the area," she says. "What does this area mean? It's creativity, it's curiosity, it's artists." Summer in a Bottle came out of a three-hour conversation at a pub in East London with a designer her husband tracked down: "We sat there talking about the area and the brand and my family and the history, and became so connected. And he just got it." There was no research behind it — "There was no board. There was no industry research. It was just: cider is big in England, and Wölffer is summer in a bottle." The Label Everyone Copies but No One Can Replicate Summer in a Bottle's floral artwork became one of the most imitated designs in wine. "I've seen a version of that bottle everywhere," Joey says, "but nobody can actually do the artwork, because it's actually printed on the bottle." Her advice for tuning out the copycats flooding the rosé category is blunt: "Don't try to be them. Don't even look at them. Don't even engage with them. You keep doing what we're doing." Turning Down a Buyer to Protect the Brand As Wölffer scaled from a boutique tasting room into Whole Foods and California's Pavilions grocery chain, Joey says she's had to actively guard against consolidation. "We had somebody come to us recently... they were like, well, we're huge," she recalls. "This is my brand, and I have to protect it. Would you hurt my brand? Yes. Is it worth it for what comes of that? Probably not." Rejecting the "Founder Is Sexy" Myth Joey pushes back on how entrepreneurship gets marketed online. "I think social media is such b.s. in the way that they present these founders," she says. "Why don't you present the other side — the tears, the fights — that makes a lot of founders feel a lot better?" Asked about the single biggest misconception about being a founder, her answer is one word: "That it's sexy."

    20,000 to 300,000 Cases: How Joey Wölffer Built a Hamptons Wine Empire
  2. Aug 25

    Only 3 Products in 12 Years: How April Gargiulo Built a Cult Skincare Brand, Vintner's Daughter

    April Gargiulo, founder and CEO of Vintner's Daughter, joins Professional Jealousy to share how growing up in a Napa Valley winemaking family shaped her approach to skincare — and why she's released just three products in twelve years, each one taking three to six weeks to formulate from whole plants. April walks host Natasha Jakubowski through the early days of building Vintner's Daughter: convincing skeptical labs to break from decades of standard practice, hand-packing the brand's first 500-bottle run herself, and growing an entirely word-of-mouth following — "girlfriend to girlfriend" — with no paid advertising, ever. She also explains why Vintner's Daughter's nutritional skincare formulas reject the beauty industry's "anti-aging" and "fix and correct" messaging, what it takes to scale a luxury brand without compromising quality, and her vision to build a heritage skincare company meant to last for generations, not one built to sell. They close with a look at what's next for the brand — the limited-edition Understory scent and the new Active Renewal Cleanser — and April's honest answer to the question: who is she professionally jealous of? In this episode: How a wine country upbringing shaped Vintner's Daughter's three-to-six-week formulation processWhy April built a cult beauty brand on just three products instead of constant new SKUsThe word-of-mouth growth strategy behind one of skincare's most talked-about brandsWhy Vintner's Daughter avoids "anti-aging" and "corrective" beauty marketing languageWhat's next: the Understory scent and the new Active Renewal CleanserWho April Gargiulo is professionally jealous of Full show notes and timestamps at professionaljealousy.com. Professional Jealousy is hosted by Natasha Jakubowski, Chief Innovation Officer at Anomaly, a global marketing agency, featuring candid conversations with the founders, CEOs, and creatives she's lucky enough to talk to — and a little envious of. New episodes every week.

    Only 3 Products in 12 Years: How April Gargiulo Built a Cult Skincare Brand, Vintner's Daughter
  3. Jul 28

    From Celiac Diagnosis to 20,000 Grocery Stores: Feel Good Foods CEO Vanessa Phillips

    Vanessa Phillips, co-founder and CEO of Feel Good Foods, joins Professional Jealousy to share how a celiac disease diagnosis in college — and a doctor's advice to give up on food entirely — became the origin story for one of the fastest-growing gluten-free frozen food brands in the country. Vanessa walks through her path from growing up in her family's New York bagel and Chinese restaurant business, to opening the gluten-free café Friedman's in Chelsea Market, to mailing homemade gluten-free pot stickers to Whole Foods in a Ziploc bag and landing a regional launch just months later. In this conversation, Vanessa gets candid about the early bootstrapped years demoing product in Whole Foods aisles for months on end, the manufacturing mistake that nearly derailed the brand's first production run, and how she built a company culture around grit, generalist skill-building, and staying close to the consumer. She also opens up about the mentor who shaped her mindset, the tools she uses to stay grounded as a founder, and who she's most professionally jealous of today. Whether you're building a CPG brand, working in food and beverage, or just love a founder story rooted in personal struggle turned purpose, this episode is packed with real, tactical lessons on category creation, scaling from founder to CEO, and building a brand that can grow with you instead of boxing you in. In this episode: Building a gluten-free frozen food brand from a personal health diagnosisCreating a new grocery category from scratchBootstrapping a CPG brand without outside capitalLessons from a costly early manufacturing mistakeMentorship, mindset, and staying grounded as a founderHow the gluten-free consumer has evolved into the mainstream "curious consumer"Who Vanessa Phillips is professionally jealous ofWatch, subscribe, and follow Professional Jealousy on Spotify, Apple Podcasts, and YouTube for more conversations with founders, CEOs, and creatives redefining their industries.

    From Celiac Diagnosis to 20,000 Grocery Stores: Feel Good Foods CEO Vanessa Phillips
  4. Jul 14

    Creating A Luxury Brand Dedicated to Radical Pleasure, Richard Christiansen, Flaming Estate

    In this episode I chat with Richard Christiansen, the founder of Flamingo Estate. Richard shares his journey from running Chandelier, a high-end fashion and luxury advertising agency in New York City, to building a global lifestyle brand almost by accident. After facing severe burnout, Richard escaped to Los Angeles just as COVID-19 hit. What started as a chaotic effort to help a local farmer sell her vegetables out of his bookstore quickly transformed into a thriving bath, body, and agricultural empire. Richard discusses the grueling reality of raising capital, the deliberate choice to choose pleasure over his successful marketing business, and what it takes to protect the intimacy and authenticity of a brand as it scales. As we chatted, I was inspired and also increasingly convinced that Richard is savvily building a new type of luxury lifestyle brand that could become of force globally. Key Themes: 1. Fiercely "Acting Small - Big brands often lose their magic because they get too self-conscious and safe. Richard keeps Flamingo Estate intimate by writing all company copy himself, rejecting AI in customer service, and managing operations internally. Staying intentionally small protects the brand's soul. 2. Selling Pleasure, Not Sustainability - Consumers quickly tune out dry environmental lectures. Flamingo Estate uses strict regenerative sourcing, but hooks customers through design, hedonism, and sensuality. The brand wins by framing pleasure—not sustainability—as a basic human right. 3. Rewriting the Scaling Playbook - Scaling a business that mixes low-margin agriculture with high-margin beauty means ignoring traditional venture capital advice. Richard survived 162 investor rejections, triple-mortgaged his home, and ignored pressure to drop the food items to protect his multi-dimensional vision. Richard was professionally jealouse of Jane Goodall who met after reading her book and cold-calling her foundation to offer her pro-bono services. Richard admired her work, and how she ran a massive global organization dedicated to changing the world, all while leading with unparalleled grace, kindness, and quiet power. In fact, it was Jane Goodall who delivered the final push for Flamingo Estate, telling Richard to take everything he learned from "selling people shit they don't need" and use it to do something genuinely good for the planet. Check out https: https://flamingoestate.com/

    Creating A Luxury Brand Dedicated to Radical Pleasure, Richard Christiansen, Flaming Estate
  5. Jun 16

    Beyond Doom-Scrolling: How The States Project Built a Movement Around Grassroots Social Networks

    If you are completely exhausted by national political noise and panic-driven fundraising spam, you are looking at the wrong political map. On this episode of Professional Jealousy, Anomaly’s Chief Innovation Officer Natasha Jakubowski sits down with Daniel Squadron (former NY State Senator, Co-founder and Executive Director of The States Project, and author of the new book The Fourth Branch) and Melissa Walker (Head of Giving Circles at The States Project) to explore how true political power can be reclaimed from the ground up. As Melissa puts it: "We work not where the glamour is, just where the power is." 💡By bypassing traditional, top-down political gatekeepers and focusing directly on community grassroots, The States Project has engineered a model that allows everyday friend circles to completely shift the balance of power in state capitols. They have taken complex, intimidating political systems and turned them into a simple, collaborative math problem that trusted social networks can solve together. Tune in to discover how a former state lawmaker and a novelist teamed up to demystify power, break right-wing supermajorities on razor-thin margins, and prove that real change starts right within your own social circle. Key topics include: 00:00 – Intro: The Illusion of Federal Power 04:15 – Why Daniel Left the State Senate to Build a Movement 11:30 – Enter Melissa Walker: Translating Politics into Human Stories 18:45 – What is a Giving Circle? (And Why It Beats Traditional Campaigns) 27:10 – The ROI of Grassroots Dollars: State vs. National 36:15 – Overcoming Cynicism: How to Build a Brand People Trust 44:30 – Outro & How to Take Action Check out: https://statesproject.org/ And look for 'The Fourth Brand: How State Governments Can Save Our Union' by Daniel Squadron, Co-Founder of The States Project https://statesproject.org/fourthbranch/

    Beyond Doom-Scrolling: How The States Project Built a Movement Around Grassroots Social Networks
5
out of 5
8 Ratings

About

What if you could turn career envy into your superpower? Hosted by Natasha Jakubowski, Chief Innovation Officer at Anomaly, Professional Jealousy is a business and career podcast featuring honest conversations with world-class founders, creative innovators, and industry leaders. These are the people whose success makes us wonder: What's their secret? Each episode dives deep into the realities of entrepreneurship, leadership, and personal growth. Discover actionable career advice, inspiration, and lessons from the journeys of top business minds so you can elevate your own career.

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