Penny Linn Podcast

Krista LeRay

From the desk of our CEO & Founder Krista LeRay we welcome you to the Penny Linn podcast. Tune in every Friday to hear about all things needlepoint, Penny Linn, running a small business and more.

Episodes

  1. From College to Canvases: Meet Our VP of Growth, Amanda | Penny Linn Podcast

    6D AGO

    From College to Canvases: Meet Our VP of Growth, Amanda | Penny Linn Podcast

    In this whirlwind episode of the Penny Linn Podcast, Krista pulls back the curtain on one of the biggest transitions in Penny Linn history: turning on their brand-new warehouse fulfillment system — and surviving the chaos that came with it. After years of shipping orders out of the back of the Rowayton flagship store, Penny Linn officially flipped the switch to warehouse fulfillment. What was supposed to be a seamless backend update quickly turned into a two-hour Shopify scramble, manual SKU-by-SKU inventory updates (all 5,000 of them), and a crash course in what it really means to be the final decision-maker. Krista shares the surreal moment of realizing, “Wait… I’m the one who makes the call,” and the pressure (and power) that comes with it. The stress paid off. The warehouse launch weekend became the biggest sales weekend in Penny Linn history — bigger than Advent, bigger than Black Friday — fueled by the ongoing needlepoint boom and months of inventory planning that positioned Penny Linn as one of the few brands fully stocked when demand skyrocketed. From stretcher bars to tacks to in-demand designer canvases, timing turned out to be everything. Krista also opens up about: - The emotional push-and-pull of entrepreneurship (celebrating wins vs. immediately fixing the next problem) - The tension between handmade, small-business values and Amazon-speed expectations - Rebuilding the back office now that packing tables are gone - Restoring international shipping - A serendipitous potential collaboration with ASHA - A heartfelt Zoom call with the Stitching in Color community - Preparing for the major Tootsie licensing launch - Handing over inventory buying (gulp) and learning to invest in growth Plus, a peek at what’s on Krista’s desk: finished Playbill canvases, a mysterious “Potato Gate” Valentine, a Chanel-inspired custom-stitched bag, upcoming New York-themed souvenirs and needle minders, Eric Carle samples, and a massive restock in motion. The episode wraps with the first installment of a new behind-the-scenes employee series, featuring Amanda Caldwell (Cosgrove) — Penny Linn’s very first employee. Amanda shares her journey from working at The Eye of the Needle in college to building AC Designs with her now-husband John, and how both of them left traditional corporate paths to help build what they proudly call a “needlepoint lifestyle brand.” It’s an honest, funny, deeply transparent look at scaling a creative business in real time — imposter syndrome fading, risks increasing, and heirlooms being built one stitch at a time. Big wins. Big inventory. Big feelings. And, apparently… potatoes.

    1h 2m
  2. Wicked Good: Meet Collective Designer Kaitlin Lane | Penny Linn Podcast

    FEB 6

    Wicked Good: Meet Collective Designer Kaitlin Lane | Penny Linn Podcast

    Krista opens up about how overwhelmed she’s been lately and what it’s taken to get the Penny Linn Podcast and business back on a more regular rhythm. Fresh off a visit from her mom (Penny Linn’s unofficial team MVP and resident mahjong/needlepoint queen), she shares a peek into the Penny Linn universe: candy collabs inspired by her mom, new Tootsie finishing arriving in the shop, upcoming Eric Carle pieces (including a “very full” caterpillar), and the chaos of licensing deals, product development, and a new warehouse coming online right before Chinese New Year shutdowns. She also gets honest about burnout, the emotional weight of what’s happening in the world, and how she uses needlepoint as both escape and anchor—especially in the 5–8 p.m. “survival mode” window with two little kids. Krista talks about taking life one step at a time, doing what you can (calling reps, donating, voting), and then coming back to stitching as a place that never judges you for stepping away. In the second half of the episode, Krista sits down with one of Penny Linn Collective’s newest designers, Kaitlin Lane of Kaitlin Lane Designs. They dive into how Kaitlin fell into needlepoint in 2023 after the viral Calder Clark Christmas tree, why she started designing her own canvases when she couldn’t find what she wanted, and how her background in fish and wildlife management (!) and love of “old stuff” like The Beatles, Lord of the Rings, and classic cars all show up in her work. Kaitlin shares the story behind her hit Wicked Queen playing card canvas (and the full five‑card series), her Lord of the Rings fellowship design, vintage car lineup, Anthropologie-inspired icon glass coasters, sweet nursery-friendly geese, SEC + MLB city rectangles, and her new Beatles coaster set—plus her very relatable confession that she’s stitched almost exclusively in DMC floss so far. They talk Stitchly vs. painting, designing by “stitching it into existence,” and what’s coming next from her Penny Linn collection. If you love process talk, honest small business updates, and pop‑culture‑meets‑nostalgia needlepoint, this one’s for you.

    44 min
  3. What Happens When Everything Hits at Once | Penny Linn Podcast

    JAN 11

    What Happens When Everything Hits at Once | Penny Linn Podcast

    This week’s episode is a candid, behind-the-scenes look at what happens when a high-growth business hits friction—from delayed launches and supply chain strain to team transitions and leadership pressure. Krista opens up about a particularly tough week that forced her to confront the weight of self-imposed expectations. With multiple licensed launches (including Tootsie, Eloise, and Eric Carle) pushed back due to approvals, factory capacity, and Chinese New Year shutdowns, she shares how quickly momentum can turn into burnout when timelines don’t go as planned—and why learning to move the dates (instead of blaming yourself) is sometimes the real win. The episode dives deep into the operational reality of scaling Penny Linn: transitioning to a third-party warehouse, navigating massive order backlogs, managing overwhelmed painting services, and rethinking how launches are scheduled moving forward. Krista explains the shift away from rigid launch calendars toward a more flexible “produce first, launch when ready” mindset designed to protect both the team and the brand long-term. She also addresses broader industry challenges—why inventory shortages are happening everywhere, how restocks are being handled during the warehouse transition, and what collective designers can expect in the coming months. Along the way, Krista reflects on her deeply solution-oriented leadership style and how she’s learning to balance fixing problems with acknowledging how hard things can feel in the moment. Other major updates include: A transition of wholesale canvas ordering to StitchtentEarly exploration into printed canvases for specific use cases (and why she’s softened her stance)Hiring updates, including a new Product Development Manager openingThe decision to stop publicly sharing detailed financial numbers—and whySigning with a PR firm to support press, events, and the New York store launchThe episode closes with an honest reflection on emotional regulation, resilience, and what it means to stay steady through both highs and lows as a founder—plus a reminder that not every week is a win, and that’s okay. This is a raw, unfiltered founder update that feels more like a personal debrief than a polished highlight reel—and one that will resonate deeply with anyone building something big behind the scenes.

    41 min
  4. An Open Q&A on Business, Needlepoint, and Life | Penny Linn Podcast

    JAN 8

    An Open Q&A on Business, Needlepoint, and Life | Penny Linn Podcast

    In this candid, end-of-year episode of The Penny Linn Podcast, Krista LeRay sits down during the in-between week after Christmas to share a wide-ranging update on life, business, and what’s ahead for Penny Linn. From warehouse transitions and restock delays to exciting hires, collaborations, and the upcoming New York City store, Krista offers an honest behind-the-scenes look at what it takes to scale a fast-growing creative brand. She walks listeners through the move to a third-party logistics warehouse, explains why certain bestsellers are temporarily delayed (and reassures everyone they will be restocked), and shares how explosive growth has reshaped inventory planning, wholesale strategy, and day-to-day operations. Krista also announces plans for a Penny Linn mobile app, discusses team expansions across customer service, social media, and design, and confirms major milestones—including officially signing the New York City lease. The second half of the episode dives into an extensive Q&A, where Krista answers listener questions about long-term vision, work-life balance, branding, collaborations, needlepoint trends, finishing, pricing pressures, tariffs, and the evolving needlepoint industry. She reflects on lessons learned, mistakes she wouldn’t repeat, and the realities of running a highly visible business in the age of social media. Thoughtful, transparent, and full of practical insight, this episode is both a state-of-the-union for Penny Linn and an encouraging conversation for anyone navigating growth, creativity, and community in a small business.

    48 min
  5. Introducing the Penny Linn Podcast and The Story of How I Started Penny Linn

    10/31/2025

    Introducing the Penny Linn Podcast and The Story of How I Started Penny Linn

    In the inaugural episode of the Penny Linn Podcast, Krista shares her journey of starting and growing her needlepoint business, Penny Linn. From the initial idea to the challenges faced during the pandemic, she discusses the milestones achieved, including a million-dollar month and successful collaborations with brands like Tootsie and Eric Carle. Krista reflects on the impact of social media on sales, the importance of her team, and her aspirations for the future of Penny Linn. Takeaways: Krista's journey into podcasting began with a desire to share more than just short clips.Penny Linn started as an online store during the pandemic and has grown significantly since.The business celebrated its five-year anniversary with major milestones, including a million-dollar month.Advent boxes have become a popular seasonal product, selling out quickly each year.Collaborations with brands like Tootsie and Eric Carle are expanding Penny Linn's offerings.Social media, particularly TikTok, has played a crucial role in increasing sales and visibility.The importance of customer feedback in product development is emphasized.Krista's personal experiences, including challenges during pregnancy, have shaped her business journey.The team at Penny Linn is described as passionate and dedicated, contributing to the company's success.Future plans include expanding the business and possibly opening a second store.

    1h 2m
4.9
out of 5
27 Ratings

About

From the desk of our CEO & Founder Krista LeRay we welcome you to the Penny Linn podcast. Tune in every Friday to hear about all things needlepoint, Penny Linn, running a small business and more.

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