In this insightful episode of Fail with Fire, Jessie Healy, founder of the UK-based eCommerce growth agency Webtopia, shares her remarkable entrepreneurial journey. Jessie’s experience spans spending $50 million on digital advertising for major brands like Etsy, Farfetch, and Candy Kittens, leading to the creation of her agency. Throughout the episode, Jessie discusses the challenges of running a fully remote agency, her decision to sell Webtopia, and the lessons learned from overcoming obstacles, such as navigating iOS 14’s impact on digital advertising. This episode is a must-listen for anyone looking to scale a business, balance personal and professional life, or understand the realities behind successful entrepreneurship.

In this insightful episode of Fail with Fire, Jessie Healy, founder of the UK-based eCommerce growth agency Webtopia, shares her remarkable entrepreneurial journey. Jessie’s experience spans spending $50 million on digital advertising for major brands like Etsy, Farfetch, and Candy Kittens, leading to the creation of her agency. Throughout the episode, Jessie discusses the challenges of running a fully remote agency, her decision to sell Webtopia, and the lessons learned from overcoming obstacles, such as navigating iOS 14’s impact on digital advertising. This episode is a must-listen for anyone looking to scale a business, balance personal and professional life, or understand the realities behind successful entrepreneurship. 00:00 Introduction 01:57 Connecting with Women in DTC 03:37 How Family Views Jessie’s Work 05:48 Introduction to Failures and Growth 06:24 Moving to New Zealand While Running a UK Agency 10:01 Remote Leadership Challenges 12:05 The Impact of iOS 14 14:09 Isolation and the Weight of Leadership 15:15 Balancing Agency Life and Motherhood 16:19 Realizing the Need for Change 17:58 Selling Webtopia 19:39 Hurdles in Selling an Agency 20:43 Post-Sale Life and Business Shift 21:14 Realities of Running an Agency 23:32 iOS 14 and Shifting Consumer Behavior 25:01 Reflections on Agency Growth 28:07 Advice for Aspiring Media Buyers 30:08 The Role of a Modern Media Buyer 33:48 The Balance of Creative, Data, and Client Management Overview of this episode of Fail With Fire Introduction to Jessie Healy Jessie’s background in digital advertising and experience working with major brands, leading to the creation of her agency Webtopia. Building Webtopia How Jessie founded Webtopia in 2018, scaling it to seven figures, and the unique value proposition of offering creative-focused strategies in a competitive eCommerce space. Challenges of Running a Remote Agency The challenges Jessie faced when managing a remote team from New Zealand while her agency was based in the UK, including time zone difficulties and balancing work and personal life. Navigating iOS 14 & Client Challenges Jessie shares how the iOS 14 privacy update and changes in consumer behavior during the pandemic made it harder to maintain clients and deliver results, pushing her to rethink her business model. Decision to Sell the Agency Jessie’s realization that she wasn’t happy running the agency, and the process she went through to sell Webtopia in 2023, along with insights on the challenges and lessons of selling a business. Life After Selling the Agency How Jessie has transitioned into consulting and running an accelerator for eCommerce brands, plus the personal and professional transformations she experienced. Hot Takes: Media Buying Today Jessie shares her thoughts on brand PMAX traffic and incremental growth, questioning whether Google’s brand traffic is truly driving new customer acquisition. Connect With AdBeacon! www.AdBeacon.com https://www.instagram.com/adbeacon/ https://www.facebook.com/OfficialAdBeacon/ https://twitter.com/ad_beacon https://www.tiktok.com/@adbeacon