Email Marketing Isn’t Dead. But Trust Is Harder to Earn.

The strange contradiction around email

Small business owners want new business. That part has never changed. And many of them still see email as one possible way to generate it.

At the same time, those same business owners often hate their own inboxes.

They’re inundated with messages. Some are legitimate. Some are irrelevant. Some are aggressively promotional. And some are outright scams pretending to be a bank, credit card company, courier, or other trusted organization.

So there’s an obvious contradiction: we want to use email to reach people, while personally wishing fewer people would email us.

That doesn’t necessarily mean email marketing is dead. I think it means the bar has gone up.

Most small businesses aren’t really doing email marketing

In my experience, the bigger problem isn’t that small business owners have tried email marketing and decided it doesn’t work. Most simply aren’t doing it.

They may have heard of Mailchimp or something similar. They may have customer information sitting in QuickBooks. Some have a CRM, although plenty don’t. But very few have a simple, repeatable system for staying in touch with customers or reaching out to prospects.

It reminds me of YouTube. A lot of business owners understand that regularly publishing useful videos could potentially generate business. So why don’t they do it?

Because it takes effort. There’s a learning curve. There’s always something more urgent to deal with today. And marketing gets pushed to tomorrow.

Email is similar. Sending one email is easy. Creating a process for sending the right emails to the right people consistently is something else entirely.

Start with the people who already know you

Before worrying about cold outreach, there’s a much easier place to start: your existing and former customers.

At the very least, I think a business should find reasons to communicate with its customer base periodically — including customers it may not have done business with for a year or even two.

The purpose doesn’t always have to be “buy something.” In fact, it probably shouldn’t be.

Send something useful. Share a helpful tip. Bring something relevant to their attention. Thank them for their business. Send a seasonal message. Depending on the relationship, even something as simple as remembering a birthday can be meaningful.

The point is to stay top of mind without becoming a nuisance.

I’ve seen simple email campaigns work

One of my clients runs an annual hockey draft pool. Each year, I help them send an email campaign to roughly 7,000 contacts inviting them to participate. This year, more than 2,000 people registered. The campaign is promotional in a sense, but it isn’t a hard sales pitch. It’s relevant to the audience, there’s a reason to participate, and there’s a prize-oriented incentive.

Another client sends a simple seasonal message to its customer base around Christmas. It’s essentially a thank-you and a holiday greeting. Again, there’s no complicated funnel behind it. It’s simply maintaining the relationship.

I’ve also used email for New Phase itself in a very straightforward way: asking customers for a Google review. I sent roughly 50 requests and received about 10 five-star reviews. That’s around a 20% response in terms of completed reviews — absolutely worth the effort.

Cold email is a different kettle of fish

Cold outreach is harder because the recipient doesn’t already trust you, they don’t even know you.

I’ve been experimenting with a relatively small-volume approach myself. Typically, I send about 30 to 40 cold emails on a business day, usually Tuesday through Thursday. I use AI to help customize the message and create subject lines that are relevant to each particular prospect.

I don’t think of that as “mass email.” It’s still cold email, but I deliberately keep the volume low enough that I can scrutinize the messages before they go out.

My conversion rate isn’t spectacular. I’m still learning what works. But that’s true of most cold marketing. Cold calling, direct mail, door hangers, and other forms of unsolicited outreach often produce low response rates too.

The real question isn’t whether the percentage looks impressive. It’s whether the economics work.

If one or two new customers have enough lifetime value to justify the effort and cost of the campaign, a seemingly tiny conversion rate can still make sense.

Don’t machine-gun your way through the market

AI creates an enormous temptation here.

If technology allows you to send 10,000 personalized-looking emails, why not send 10,000? Because the ability to do something at scale doesn’t automatically make it a good idea.

I’d rather send 30 thoughtful messages that I’ve actually looked over than cast the largest possible fishing net, annoy thousands of people, and damage my reputation in the process.

There are also real compliance and deliverability considerations around commercial email. In Canada that means CASL (Canada’s Anti-Spam Legislation), and in the US, CAN-SPAM. Businesses need to understand the rules that apply to them rather than assuming that because software can send a message, they’re automatically entitled to send it.

And recipients themselves are becoming better protected. Spam filters are smarter. Inbox tools are increasingly using AI to decide what deserves attention. We’re approaching a strange point where AI may be writing an email on one end and another AI may be deciding whether the human on the other end should even see it. How soon will we hear, “I’ll get my AI to email your AI”?

The real problem is trust

That may be the most important change in email marketing.

Thirty years ago, getting an email was actually exciting. Today, many people are suspicious before they even open one. Some won’t open anything from a sender that’s not in their contact list.

That isn’t irrational. Years of spam, deceptive marketing, phishing, viruses, and outright criminal activity have trained people to be cautious.

Marketers have contributed to the problem too. There’s an old saying that marketers ruin everything. There’s some truth to it. Once a channel works, people exploit it until the audience learns to defend itself.

We’ve seen something similar with phone calls. There was a time when calling someone was completely normal. Now even people who know each other text first to ask if it’s okay to call.

The scarce resource isn’t the ability to send a message anymore. It’s permission to have someone’s attention.

Give before you ask

So how do you earn that attention?

For me, it comes back to value.

Gary Vaynerchuk has popularized a simple idea that I’ve always liked: give, give, give, then ask. The wording may vary, but the principle is solid.

Give people useful information. Help them solve a small problem. Point out something they may not know. Do that consistently enough and you begin to establish credibility.

Then, when you eventually ask for something, make the first ask small. Don’t immediately request a purchase. Ask for a conversation. Ask whether they’d like an assessment. Ask whether the issue you’ve identified is worth discussing.

Technology can help enormously with the process, and AI can make thoughtful personalization much more practical. But technology shouldn’t eliminate the judgment that makes communication human.

At the end of the day, people still deal with people

For service businesses in particular, all of these layers of technology eventually have to lead somewhere.

A CRM can organize the relationship. AI can help write the message. Automation can send it at the right time. Another AI may even filter it on the receiving end.

But eventually, one person has to trust another person.

That’s where most meaningful service-business sales still happen.

So I don’t think the useful question is, “Is email marketing dead?”

A better question is: “Can I use email in a way that gives someone a legitimate reason to pay attention to me?”

For a small business owner, the answer can still be yes.

Just start small. Stay useful. Pay attention to who you’re contacting. Don’t abuse the technology. And remember that the objective isn’t to send more email.

The objective is to earn enough trust to start a human conversation.