Subscription Stories: True Tales from the Trenches

Robbie Kellman Baxter

Subscription models are crazy powerful. Savvy small companies can easily deploy them to knock huge Goliaths off kilter. We’ve seen it in entertainment, software, hardware, news, retail, hospitality—the list goes on. In her podcast series, Robbie Kellman Baxter interviews the leaders of this revolution about how they’re using subscription pricing and membership models to redefine the biggest industries and generate predictable recurring revenue along the way.

  1. 05/07/2025

    Building Evergreen Companies with Dave Whorton, Founder of the Tugboat Institute and Author of Another Way: Building Companies that Last…and Last…and Last

    Something I've noticed over the years is that there's a natural membership economy mindset among many family-owned businesses and organizations, not on the venture-backed IPO acquisition path. Companies that aren't on a tight timeline to an exit have the ability to invest in long-term, trusted relationships with customers and with employees. After a career as both a founder of multiple successful companies and a venture investor with Kleiner Perkins, Dave Whorton decided he wanted to work specifically with what he came to call Evergreen leaders, the ones who combined sound business principles, extraordinary purpose, and a desire to share their success with their employees. His Tugboat Institute researches these organizations to identify best practices, and then he brings together these leaders to teach and support one another. Now, he's written a book, “Another Way: Building Companies That Last…and Last…and Last”. It's a playbook for entrepreneurs seeking an alternate path to success. In my conversation with Dave, we discussed how venture capital has changed the face of entrepreneurship, what it means for founders, the 7Ps that are the guiding principles of Evergreen companies, and the two key constituencies that matter most to your organization's long-term success.   Love the show? Rate us ⭐️⭐️⭐️⭐️⭐️ and leave a review on Apple Podcasts! Here’s How » Join the Subscription Stories Community today:     robbiekellmanbaxter.com Twitter Facebook Robbie Kellman Baxter on Instagram Subscription Stories: True Tales from the Trenches on Apple Podcasts

    40 min
  2. 03/05/2025

    A Behind-The-Scenes Look at Adobe’s Journey to Subscriptions with Mark Garrett, the CFO Who Architected That Transformation

    In today's episode, we're exploring one of the most ambitious and successful business model transformations in modern corporate history, the shift of Adobe from a traditional software company selling packaged products to a thriving subscription powerhouse. And who better to walk us through this journey than Mark Garrett, Adobe's former chief financial officer and the architect behind this transition?    When Adobe first announced its move to a subscription-based model in 2011, there was plenty of skepticism. Analysts questioned the financial impact, customers worried about cost increases, and internal teams faced the daunting task of restructuring their entire go-to-market strategy. Mark and his team remained steadfast, not just in their belief that subscriptions would create more predictable revenue, but also that they would allow Adobe to serve customers better with continuous innovation and improved accessibility. Since those early days, Adobe's market cap has skyrocketed from around 16 billion before the transition to well over 200 billion, proving just how powerful a well-executed subscription strategy can be. In this conversation, Mark shares the behind-the-scenes story of how Adobe made the leap as a public company, maintaining exceptional financial performance while also enhancing customer satisfaction. We'll discuss the key strategies behind their transition, the biggest challenges they faced both internally and externally, and what other companies can learn from Adobe's playbook. If you've ever wondered how to execute a high-stakes business model transformation, how to balance Wall Street expectations with long-term customer loyalty, or how to design a subscription offering that truly delivers ongoing value, this episode is for you.     Love the show? Rate us ⭐️⭐️⭐️⭐️⭐️ and leave a review on Apple Podcasts! Here’s How » Join the Subscription Stories Community today:   robbiekellmanbaxter.com Twitter Facebook Robbie Kellman Baxter on Instagram Subscription Stories: True Tales from the Trenches on Apple Podcasts

    41 min
  3. 02/19/2025

    How to Build a Strong Subscription Business While Maintaining a Compelling Free Tier with Chess.com CRO Adam Mayer

    Chess.com is one of the most popular freemium platforms in the world, offering millions of users free access to an engaging online chess experience. But how do you encourage players to upgrade to a paid tier when the free version is already so compelling? Adam, with his extensive background in revenue strategy and subscription growth, has played a critical role in designing and optimizing Chess.com's premium offerings. In this conversation, we'll dive into the challenges and opportunities of building a successful paid tier within a thriving freemium ecosystem, how chess.com balances free and premium value, the strategies they've used to convert free users into loyal subscribers., and the key lessons Adam has learned from his experience leading revenue at a fast-growing digital platform. If you're interested in learning how to drive revenue without alienating your free user base, how to craft subscription tiers that meet diverse customer needs, and how to foster long-term loyalty in a competitive market, then  you won't want to miss this episode.   Love the show? Rate us ⭐️⭐️⭐️⭐️⭐️ and leave a review on Apple Podcasts! Here’s How » Join the Subscription Stories Community today:   robbiekellmanbaxter.com Twitter Facebook Robbie Kellman Baxter on Instagram Subscription Stories: True Tales from the Trenches on Apple Podcasts

    40 min

Trailers

5
out of 5
115 Ratings

About

Subscription models are crazy powerful. Savvy small companies can easily deploy them to knock huge Goliaths off kilter. We’ve seen it in entertainment, software, hardware, news, retail, hospitality—the list goes on. In her podcast series, Robbie Kellman Baxter interviews the leaders of this revolution about how they’re using subscription pricing and membership models to redefine the biggest industries and generate predictable recurring revenue along the way.