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10+ Email Marketing Tips to Warm Up Cold Leads with Jay Schwedelsen

10+ Email Marketing Tips to Warm Up Cold Leads w/ Jay Schwedelsen

You’ve probably heard the email advice: “Don’t use the word ‘free.’” “Keep your emails short or risk going to spam.” “Don’t use emojis in subject lines.” Turns out, a lot of that advice is outdated — and in some cases, flat-out wrong.

Jay Schwedelsen, host of the popular marketing podcast Do This, NOT That, recently joined us on Carrot’s Evergreen Marketing podcast to share updated tips for successful email lead nurturing. Jay is undisputedly one of the top experts in the field and he shared 10+ tips and dispelled some popular myths around email. 

If you’ve left email behind in your lead follow-up, it’s time to dust off your list. 

“Your email list is probably the most important asset you have. Your email database is your owned asset. It is the only marketing channel for basically no money that you can communicate whatever it is you want to communicate at any given moment. There’s nothing else like that.” — Jay Schwedelsen

Even if you are actively sending emails, you might be unknowingly making some mistakes that are hurting your engagement rate.

Whether you’re an investor following up with cold leads, an agent sending out market updates, or just trying to figure out how to get more replies, there’s something in the episode for you. Here’s a sneak peek at three tips Jay discusses.

Tip #1: Your emails don’t matter if they aren’t opened

“A lot of times when we’re sending out an email, we’re worried about ‘oh what are we writing in the email?’ or ‘oh, what’s the offer?’ and that’s backward,” Jay explained. “If you don’t get the email opened, who actually cares what’s inside the email? So we have to get that email opened and the number one thing that’s going to get that email opened is the subject line.”

When people look at their email inboxes, they scroll through quickly and decide what gets their attention. Jay contends that most people don’t read the entire subject line, instead focusing on the first few words.

With that in mind, front-load your subject lines. Jay recommends starting a subject line with all caps or keeping it super short to make it stand out. Better yet, start your subject line with a number.

“If you start your subject line with a number, your open rate will rise about 20%.”

And forget about avoiding certain “spam trigger” words. It’s true that words like “free” or even dollar signs used to send your emails straight to the junk folder, but that’s not the case anymore. Feel free to write the most compelling subject line possible without avoiding important words!

Need help with your subject lines? Check our Jay’s free subject line grader.

Tip #2: Send more emails (yes, you read that right!)

“You’re probably not sending out enough email. In the real estate market I see this a lot. People will get focused on their email sending for a month or two, and then they move onto something else, and they won’t send again for another 2-3 weeks or a month. The most important thing you can do to make sure you’re getting that business is to be sending enough. You need to be at least sending email weekly — at least!”

Why? Because sending email frequently and consistently actually helps keep you out of the junk folder. It all comes down to email engagement, Jay explains.

“If you don’t send enough email — and we see it in all the data — if you don’t send at least a weekly email to your database, you actually cannot generate enough opens and clicks to stay in that person’s inbox. It needs to be relevant stuff, it can’t be garbage. But sending out more email is step number one.”

Since email engagement is actually what matters, Jay has a few tips to make sure people actually read and interact with your email.

  • Paragraphs should never be more than four lines.
  • Start your email with something super attention-grabbing. Don’t save the “hook” for the end … some readers won’t get there.
  • Restate the main point, offer, or action you want readers to take in a PS at the end of the email (to grab the attention of people who just skim).

“When you have a PS with a call to action, a link in the PS, your click-through rates go up on average by about 15%.”

Tip #3: Make your emails valuable

“Don’t push offers until you’ve established the fact that you’re not annoying.”

Let’s be honest, no one likes being sold to. But as real estate professionals and marketers, it’s our natural default to send offers and promotions. If you’re working on a cold list — or a new one — focus your first few emails on offering value to your leads.

“For the first 4-5 sends, don’t promote anything. Nothing you send out should be a benefit to you the sender, it should only be a benefit to the individual you’re sending to. It’s hard to do because our nature is “sell, sell, sell” but you need to show the people in that database that you’re going to give them value.”

Jay shares some ideas of valuable information to send your leads (you’ll have to listen to get his tips), but whatever you send can’t have a form in front of it. Offering value before asking for something builds trust and gets leads used to opening your emails. When you do send something promotional, they’re more likely to pay attention because of the relationship you’ve built.

“It’s like dating. You can’t be just like ‘Hi, nice to meet you. Do you want to get married?’ It doesn’t work, it’s weird.”

Tips #4-10: More gems from Jay

In less than 40 minutes, Jay shares insights on not only how to successfully use email nurturing, but creative ways to grab attention and make your emails better every time. More tips covered in the podcast include:

  • Why the inbox promotions section isn’t as bad as you think
  • The best way to benchmark your email marketing success
  • How to get people to respond to your emails
  • Going beyond basic AI to really make your emails better (including using AI to analyze your competitors’ emails for new ideas)
  • Should you use emojis and memes in your emails?

Stop Overthinking, Start Sending

At Carrot, we talk a lot about building a business of freedom and impact. And email — done right — is one of the most powerful, low-cost tools you have to create conversations that lead to deals.

So whether you’re following up with motivated sellers, re-engaging old leads, or just trying to stay visible, start putting these tips into practice. Then hit send. Test. Iterate. Improve.

And remember: It’s not about perfection. It’s about progress.

Listen to the full 10+ Email Marketing Tips to Warm Up Cold Leads w/ Jay Schwedelsen episode to unpack what’s actually working right now in email marketing. 

PS – You can use these tactics in your automated outreach sequences in Carrot CRM!

Jamie Saine

Jamie has spent the past 15+ years as a content and product marketer, helping companies rank well and build trust online. She specializes in deep research, producing a range of helpful media, and translating technical jargon and complex topics into something anyone can understand.

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