In this special episode of the Membership Geeks Podcast, I open up about the toughest moments and biggest challenges I’ve faced over a decade of running a membership business. As we kick off a month of anniversary content, I dive deep into pivotal decisions, unexpected setbacks, and the realities that most membership owners rarely talk about publicly. Whether you’re just starting out or have been running your own membership for years, my honest reflections are here to shed light on what it really takes to keep going—especially when things get tough.

In this episode:

• What were the most difficult decisions I had to make in the early days of launching and shifting my business model?
• How did I handle sudden competition from a well-funded, well-connected industry player—and what impact did it have on my mindset and business?
• In what ways did external crises like COVID-19 test my resilience and force me to adapt my membership offer and team structure?
• What was it like to experience internal challenges, such as letting my first team member go and navigating the unexpected departure of a cofounder—and how did these affect my business moving forward?

Key Quotes & Takeaways:

"If you've been listening to us for a while, you'll know that I never shy away from the uglier side of the membership world of business, and I always give it to you straight."

"We couldn't compete with the black book, the huge financial backing, and the fact that they could incentivize others to portray them as this ever knowing, all knowing guru, and fast track them to their place in the industry by paying them a thousand dollars for every customer that they referred."

"A lot of people kind of revealed what their true motivation was. And I've got to be honest, that that made me a lot more cynical about the online business world and the kind of people who were influential within it"

"You can never go wrong just refocusing on your people. Right? Refocusing on your members. Why you're doing it for them? What they need from you? How you can best serve them?"

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