Many subscription entrepreneurs lament their lack of fancy software and dashboards to allow them to better manage their business. But if you know your ideal member and understand their pain points, and if you're always tinkering and adjusting your offering to better align with the needs of those members, you can build a powerful recurring revenue business.

Even as a solopreneur, this week's guest, James Schramko has developed a unique model to help consultants and experts earn more while working less. And while he has been an early adopter of technology, many of the tools and tactics are flexible enough to be used by large or even very small businesses.

More importantly, James has succeeded in building his subscription-based business by focusing on his members and their desired outcomes. Ultimately, membership is about trust and relationships, and James is an expert in both.

In today's conversation, you'll learn why bundling too much into your subscription can cost you members, how to use technology to support a global community, and why a tiered ascension model sometimes leaves money on the table.

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One of the great mysteries for me is why so many otherwise sophisticated companies don’t focus on involuntary churn. Also known as passive churn or accidental churn, involuntary churn happens when a payment issue raises a flag that causes a merchant to cancel a customer’s subscription. In 70% of these cases, there is no fraud, so the company is literally turning away excellent customers.

Involuntary churn routinely impacts about 10% of Annualized Recurring Revenue (ARR), according to some estimates. In today’s episode, Vijay Menon, founder and CEO of Butter Payments, and I discuss what drives involuntary churn, why so many companies underinvest in this problem, and some key tactics to drive revenue growth through better payment management.

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Loyalty programs seem to be at a crossroads. Industries including hospitality, financial services, and retail are going beyond the points-based programs we're so familiar with and exploring more personalized, emotionally engaging programs. Some, like CVS, Inspirato, and of course Amazon with Amazon Prime have even incorporated paid loyalty subscriptions which provide benefits in exchange for an annual fee instead of requiring customers to earn benefits through their spending and behaviors.

Today's guest, Nadia Popova of Euromonitor International, follows the loyalty trends and provides insights across industries regarding best practices in building long-term relationships with customers.

In this wide-ranging conversation, we talk about how consumer expectations have changed since COVID, why personalization is so important, and where subscriptions fit in the broader loyalty landscape.

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Loyalty programs have been around forever. Points, cashback, branded credit cards, and now increasingly, we're seeing paid subscription loyalty programs, like Amazon Prime or CVS Care Pass. The goal is the same, to smooth out the lumpy buying behavior common in consumer packaged goods, retail, and hospitality, and to drive habits and engagement.

Today's guest, Justin Honaman, leads the worldwide retail and CPG go-to-market team at Amazon Web Services. He also hosts the popular podcast, ContenderCast, where I was a guest a few years ago.

In this conversation, Justin and I talk about the changing landscape of loyalty programs, why loyalty is so important right now, and what's driving the rise in these subscription programs.

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Building a new subscription model in a large, successful company is hard enough, but when your company's core competency is manufacturing and the subscription involves content and software, you have to do more than build the new business model. You have to change the way the organization thinks about product management.

With experience, both at PlayStation and at Ford, today's guest, Ross McGregor, will shed light on how to build a service orientation across a product team. Something critically necessary if you're going to build a forever transaction with your customers. In this conversation, he talks about how to put together the business case that merits a strategic bet on subscriptions, how to build support across the organization from the beginning, and when it's time to scale the experiments.

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You're in for a special treat today. My guest, Dr. Tacy Byham, is the CEO of Development Dimensions International, or DDI, a global leadership consulting firm that helps organizations hire, promote, and develop exceptional leaders. A few years ago, I worked with Tacy and her team as they incorporated subscriptions into their business model. The results have been extraordinary. Three years into the launch, over 50 percent of DDI's revenue comes from subscription clients.

I've been asking Tacy to share her journey for quite some time, and I'm thrilled that she finally agreed. In today's conversation, we'll talk about how subscriptions can smooth out the lumps in B2B services, how to put together the right team with the right mindset for subscriptions, and how to keep up the momentum after the initial experiments with subscriptions are over.

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The world of B2B subscriptions has changed a lot since companies like Salesforce first paved the way for what would become known as Software-as-a-Service. And while there are hundreds of marketing and sales-oriented SaaS products, it's taken a lot longer for the subscription model to be fully embraced in the CFO's office.

Randy Wootton has seen the evolution of SaaS and understands the changing role of the CFO better than most. He's led businesses focused on sales and marketing solutions at companies like Salesforce, Microsoft, and Rocketfuel, but more recently took over the CEO role at Maxio, a leading provider of billing and financial ops solutions for B2B SaaS companies.

In this very rich and full conversation, we talk about why pricing and packaging of subscriptions is so hard, the power of a pricing council, and the changing role of the CFO in a SaaS world.

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If your subscription uses a freemium model, it can be tricky to decide what’s always free, what’s free for a while, and what’s always behind the paywall. Knowing how to manage people at each stage of the funnel can be really challenging.

Today’s guest, Ken Houseman, is an expert on both the strategy and the technology required to monetize the funnel for acquisition, upsell, and retention. Today’s conversation isn’t based purely on Ken’s work as VP of Product for The New York Times, and in no way represents the editorial perspective of the organization. Ken’s experience there, as well as his work with organizations, including Oracle, Nike, and even the US military, have shaped his perspective on managing the customer relationship.

In this conversation, we discuss why retention is the next obsession for subscription leaders, what needs to be different about how to optimize your ERP for subscriptions, and a few of the less obvious things that can go wrong on the path to conversion.

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