How long should I keep following up with a lead?

Longer than most reps think. Drewbie followed up with one lead for over three years, and it became one of the biggest insurance deals of that career. People buy on their own timeline, so track your leads, stay patient and keep showing up so they call you when their moment comes.

How do I follow up without being annoying?

Bring value every time. Nobody wants to be the person sending 40,000 messages like a crazy ex. Give the lead a reason to respond with each touch, mix up calls, texts, emails and letters, and focus on the relationship. When people feel like you actually care, they trust you with their business.

What do I need to set up a follow-up system?

Start with a CRM, automation, or at least calendar reminders so no lead slips. Build a touchpoint sequence that mixes calls, texts, emails and even letters, and track every lead as it moves. The system keeps you consistent, and that matters because 95% of people aren't ready to buy today.

What if the lead never buys from me?

Ask for referrals anyway. Even if they don't buy, they might know someone who will. People who feel like you actually care trust you with their business and their referrals, so the relationship you built through follow-up still pays off when the sale itself doesn't happen.

follow-up · podcast ·Apr 03, 2025

The "FU" Money Comes From Persistant Follow-Up

by Drewbie Wilson

In this episode of Call The Damn Leads, we’re talking about one of the biggest factors that separates closers from tire-kickers: persistence in follow-up. Let’s be real—most people don’t buy on the first contact. They get busy, distracted, or just aren’t ready yet. That doesn’t mean they’re a lost cause.

Key Takeaways

Only 5% of leads buy right away, so skipping follow-up throws away the other 95% of your potential sales.
People buy on their own timeline, and your job is to stay in their orbit so they call you when their moment comes.
Give the lead a reason to respond in every follow-up and skip the 40,000 desperate messages.
Mix calls, texts, emails and even letters, and track every lead in a CRM, an automation or calendar reminders.
One lead took over three years of follow-up and turned into one of Drewbie's biggest insurance deals ever.

The truth? 95% of people aren’t ready to buy today—but they might be tomorrow, next month, or even next year. Your job is to stay top of mind without being spammy or obnoxious. I break down real-world examples of how consistent, value-driven follow-up can land massive deals, build trust, and make you the go-to person in your industry.

Key Takeaways

🔥 Follow-Up Wins Deals – Only 5% of leads buy right away. If you aren’t following up, you’re throwing away 95% of your potential sales.

🔥 Persistence, Not Annoyance – Nobody wants to be the person sending 40,000 messages like a crazy ex. The goal is to stay top of mind with value, not desperation.

🔥 The 3-Year Follow-Up That Closed Big – I share a wild story about how I followed up with a lead for over three years—and it turned into one of my biggest insurance deals ever.

🔥 Timing is Everything – People buy when they’re ready, not when you are. Your job is to stay in their orbit so that when their moment comes, they call you.

🔥 Relationship Over Pressure – Follow-up isn’t just about sales—it’s about building genuine relationships. When people feel like you actually care, they trust you with their business (and their referrals).

Actionable Steps

✅ Set up a follow-up system (CRM, automation, or at least calendar reminders).
✅ Create a touchpoint sequence—mix calls, texts, emails, and even letters.
✅ Provide value in every follow-up—don’t just ask for the sale, give them a reason to respond.
✅ Track your leads and be patient—your next big deal might take months (or even years).
✅ Ask for referrals—even if they don’t buy, they might know someone who will.

Call The Damn Leads

“By sales professionals, for sales professionals.” Each week, Drewbie Wilson, a sales vet with 20+ years in the game, brings you humor, real-world stories, and powerful strategies to help you excel in your sales career.

Expect a wild mix of:

Real Sales Stories: Tales that entertain and inspire
Proven Tactics: Practical tips for boosting your sales game
Humor and Energy: Fun takes on the ups and downs of sales life
Expert Advice: Learn from seasoned pros across different fields

Whether you’re in sales, an entrepreneur, or just looking to grow your business skills, don’t miss out on these invaluable lessons and entertaining stories. Want to be a guest? Pitch your story here!

👉 Share this episode with someone who needs to hear it! Subscribe, leave a review, and, most importantly… GO CALL THE DAMN LEADS!

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More on this: Dave Molenda on adding value and setting next steps in follow-up. New here? Start with what Call The Damn Leads is.