What common founder mistakes happen with subscriptions?

Oisin O'Connor is the CEO and co-founder of Recharge, the leading subscription management platform powering 75% of all Shopify subscriptions. Under his leadership, Recharge has become a critical infrastructure partner for over 30,000 brands, reaching 100 million subscribers and $100 million ARR.

In this episode of DTC Pod, Oisin pulls back the curtain on what it really takes to win with subscriptions in today’s DTC landscape. He shares insider strategies for subscriber growth, optimizing retention, and leveraging Recharge’s newest AI-powered tools to minimize churn. Oisin also shares specific benchmarks every brand should measure, real-world examples of subscription funnels that convert, and actionable experiments operators can run to unlock long-term profitability and scale.

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On this episode of DTC Pod, we cover:
1. Evolution of subscriptions in physical product e-commerce
2. How to spot and create product-market fit 
3. Differentiators that set Recharge apart from early competitors
4. The compounding power of subscriptions for long-term growth
5. Unit economics, LTV vs CAC, and why retention is king
6. What best-in-class subscription brands do differently
7. Optimizing conversion funnels for subscriber growth
8. Subscription benchmarks: churn rates, retention, and second order metrics
9. Reducing churn with data, cancellation flows, loyalty, and rewards
10. Automations and integrating Recharge with supply chain and 3PL operations
11. Leveraging AI Concierge for customer retention and support
12. Evolving customer experience and the need for seamless subscription management
13. How Recharge guides merchants with data, support, and innovation
14. Experiments and mistakes founders make launching subscription brands

Timestamps
00:00 Oisin’s background, founding story, and early agency experiments
04:06 The rise of Shopify and the breakthrough with Recharge
05:19 The subscription model: initial skepticism and quirky early adopters
06:47 Technical challenges in enabling subscriptions on Shopify
09:00 First major subscription brand success story
10:15 Compounding growth through subscriptions
11:36 Legacy brands and decades-long customer retention
13:06 Building DTC businesses with sustainable unit economics
14:37 Lessons from TV advertising history and the narrowing of scalable models
16:29 Key traits of successful subscription businesses
17:09 Product, recurring need, and conversion strategy
18:27 Understanding subscriber value and optimizing acquisition
19:26 Retention: keeping customers post-acquisition  
19:52 High-performing brands and funnel design
20:05 Subscription by default, offers, upsells, and cross-sells
21:39 Conversion tactics from PDP to post-checkout
22:38 Benchmarks for healthy churn and retention
23:06 How top brands reduce churn and track performance
24:58 Recharge tools: analytics, cancellation flows, Klaviyo integration
26:41 Rewards and automations to boost retention
27:33 Automate flows for backend fulfillment and logistics
28:20 Launching AI SMS concierge for subscriber experience
29:40 Reducing customer service friction and delighting shoppers
32:15 Customer experience as a core differentiator
34:04 The competitive subscription landscape: Recharge’s position
35:41 Product innovation, support, and actionable guidance
37:16 Data-driven product innovation and merchant success
38:04 The future of subscription, retention, and platform innovation
40:38 Biggest mistakes founders make with subscriptions
41:58 Experiments founders should run with Recharge
42:58 Where to connect with Oisin for advice and mentorship

Show notes powered by Castmagic

Past guests & brands on DTC Pod include Gilt, PopSugar, Glossier, MadeIN, Prose, Bala, P.volve, Ritual, Bite, Oura, Levels, General Mills, Mid Day Squares, Prose, Arrae, Olipop, Ghia, Rosaluna, Form, Uncle Studios & many more.  

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Oisin O'Connor - Co-Founder and CEO of Recharge
Blaine Bolus - Co-Founder of Castmagic
Ramon Berrios - Co-Founder of Castmagic