Get Paid More Than Once—Move Beyond Single Sales Using Recurring Revenue

Hard - Requires significant effort Recommended

When running a small business, chasing one sale at a time quickly wears you out. Subscription services—where customers pay regularly for ongoing value—shift the game. Instead of wondering, 'Will anyone buy today?', your attention goes to keeping subscribers happy and steadily growing their numbers.

Imagine a friend who launches a 'Cupcake of the Month' club. Instead of baking when she gets orders, she now knows that each month, fifty subscribers are counting on her box of mini-treats. Payments arrive automatically, and her focus can move from sales anxiety to delighting loyal members.

Psychologically, recurring revenue creates a positive feedback loop for both business owner and customer. Research in behavioral economics notes consumers are more likely to stick with subscriptions they enjoy—and more willing to buy further products later. For entrepreneurs, recurring income boosts resilience, simplifies planning, and scales easily—even if the initial numbers are small.

If you’re tired of hustling for every single sale, take an evening to brainstorm what your followers or clients might want on a repeating basis—something useful, fun, or supportive. Design a simple plan: explain the perks of joining, make sign-up and cancellation easy, and send a note to your past customers inviting them to try it. Even a handful of subscribers can transform your motivation and stability, giving you breathing room to invest in quality and creativity. Start small and be ready to tweak the offering as you learn what keeps members coming back.

What You'll Achieve

Build predictable, scalable income and financial stability while increasing customer loyalty, freeing up mental energy for higher-value projects.

Design Your First Subscription or Continuity Offer

1

Brainstorm a service or product people want regularly.

Think about what your customers use up, need to refresh, or benefit from ongoing—like advice, content, treats, or tools.

2

Package it as a monthly or quarterly plan.

Create a simple subscription—such as access to exclusive tips, scheduled deliveries, or ongoing support. Make joining and quitting transparent and easy to build trust.

3

Upsell or cross-sell to your existing customers.

Offer the subscription to your current buyers, explaining how it saves them time, brings extra value, or simplifies their life.

Reflection Questions

  • What product or service could I deliver repeatedly?
  • Why might customers want ongoing value instead of one-time help?
  • What systems or changes would make recurring service easy to offer?
  • How could I test this idea with just a few people first?

Personalization Tips

  • A personal trainer offers a discounted monthly plan for ongoing video advice, instead of just single sessions.
  • A craft seller creates a 'handmade-of-the-month' box with themed gifts for subscribers.
  • A web designer delivers routine updates, backups, and 'mini fixes' on a small monthly retainer instead of per-project fees.
The $100 Startup: Reinvent the Way You Make a Living, Do What You Love, and Create a New Future
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The $100 Startup: Reinvent the Way You Make a Living, Do What You Love, and Create a New Future

Chris Guillebeau
Insight 6 of 8

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