Spam has gotten so bad that many of us hesitate before sending even a good email. We watch junk fill our inboxes all day, then wonder whether our own newsletter will feel like one more unwanted message.

That fear is understandable, but it can also cost us repeat business, upsells, and stronger client relationships. Kurt von Ahnen and Toby Cryns made the case that a smart email list is still one of the simplest ways to stay relevant, stay remembered, and keep revenue close to home.

Spam has made legitimate email feel risky

Many agency owners live in two inboxes at once. One is the inbox we wish we had, clean, useful, and full of real conversations. The other is the one we get, packed with junk, fake invites, shady reminders, and messages that make us distrust almost everything we see.

Kurt described the current state of email in the bluntest possible way. He talked about getting around 200 messages a day that belong in the trash. Some look harmless at first. Others look close enough to real services that we hesitate to click, unsubscribe, or even report them.

A few examples stood out because they feel familiar:

• Fake Zoom invites that say we signed up for a meeting we never joined
• Repeated reminders for that same fake meeting
• Calendar events that appear as if we agreed to attend them
• Suspicious messages that make us nervous to unsubscribe because they may connect to a real service

“I’m afraid to send an email out to people I know because I’m afraid they’re going to call me a spammer.”

That line gets to the heart of the problem. Spam and scam are everywhere, so even honest outreach feels risky. We start treating our own marketing like something shameful, even when we are emailing people who know us, trust us, and have already paid us.

### New spam tricks are harder to spot

The newer scams work because they feel ordinary. Toby shared that calendar events started showing up automatically, and for a while he was halfway into a meeting before realizing he never signed up for it. That is not normal spam. That is inbox confusion turned into a time drain.

We also have to separate shady tactics from basic outreach. There is a big difference between fraudulent messages and a legitimate newsletter sent to a current client list. Yet when the inbox stays polluted, those two things can feel too close together.

That is why list quality matters so much. If we want email to work, we cannot treat it like a batch-and-blast channel. We have to send fewer, better, more relevant messages. Practical guidance in this email deliverability guide for agencies reinforces the same point. Complaint rates, engagement, and list hygiene all affect whether good email lands where it should.

A smaller list can beat a giant one

Kurt’s story about list cleanup is the part many agencies need to hear. He had an old email list from Manana No Mas that had grown to nearly 8,000 people. On paper, that sounds useful. In practice, it was full of people who had no current reason to hear from his agency.

He started looking at who opened those emails. One open came from an older woman he knew from church in Colorado two decades earlier. She was not a prospect. She was not a client. She had no connection to the business. Yet she was still on the list, still getting agency emails.

That was enough to make him delete the whole thing.

Later, he rebuilt the list and got it up to roughly 16,800 contacts. Even then, he still had subscribers who had signed up but felt bothered by the emails. So he stripped it down again. The result is the part that matters: the list now sits at about 420 people, and it regularly gets a 50 to 55 percent open rate. Before that cleanup, open rates were around 2 to 3 percent.

That is the clearest argument for relevance we could ask for. 420 engaged subscribers can beat 16,800 weak ones because the smaller list still wants the conversation.

A huge list can flatter us while doing almost nothing for the business. Meanwhile, a lean list with real interest gives us a much better shot at replies, calls, project extensions, and repeat sales.

What a useful agency newsletter looks like

A good agency newsletter does not need to feel like a campaign. Kurt described sending a newsletter about every two weeks, and the content stays close to what clients already care about.

That includes a few recurring themes:

• A link to a recent podcast appearance or discussion worth hearing
• A shoutout to new client launches or recently published projects
• Social promotion for new clients who would benefit from early attention
• A practical tip, such as a new AI workflow that helps with website reviews or SEO

That last point is more useful than it may sound. Kurt mentioned getting better website audit feedback from Claude than from ChatGPT in some cases. We do not need to treat that as a trend piece. We can treat it as client value. A short note that says, “Here is a prompt we tested for reviewing your site,” gives people something they can try right away. For teams exploring that angle, this guide to using Claude for website SEO analysis offers a helpful starting point.

The key is that every item ties back to the same idea: relevance and purchase intent. If clients want to try the tip themselves, great. If they would rather hand it off, the service is already connected to the message.

Client relationships work like an emotional bank account

One of the best ideas in the conversation had nothing to do with software. Kurt described business relationships as an emotional bank account. Every interaction is either a deposit or a withdrawal.

That framing works because it is easy to test against real life. When we send helpful updates, share useful resources, promote a client’s new launch, or point out a problem before it gets worse, we make deposits. When we pitch a new retainer, suggest a hosting upgrade, or recommend a paid audit, we make a withdrawal.

If the account is empty, that sale lands badly. If the account is full, the same ask can feel welcome.

Every useful touchpoint makes the next sales conversation easier.

Toby pushed on the practical side of this. Email marketing is work. Even a monthly newsletter takes time, thought, and follow-through. Still, both of them kept coming back to the same truth: it is usually easier to sell to happy past clients than to spend money chasing strangers.

That matters even more for small agencies. Customer acquisition is expensive, slow, and uncertain. Existing clients already know how we work. They know whether we hit deadlines. They know whether we fix problems. So the newsletter is not only a marketing asset. It is a relationship tool that keeps us top of mind between projects.

That also lines up with broader email practice. This newsletter deliverability guide emphasizes segmentation and relevance for a reason. When lists stay clean and content stays focused, engagement rises and spam complaints drop.

We should sell our own expertise, not only our clients’

The discussion took a useful turn when Toby asked a hard question: if we are good at helping clients generate sales, why do so many of us avoid doing the same work for ourselves?

Kurt used his own product as the example. Powersports Academy is now in its sixth year, and after a slow start it is generating about $60,000 in annual revenue. He nearly shut it down before deciding that he had to prove the model to himself. If he helps people build e-learning businesses, he should be able to run one too.

That is an honest tension inside many agencies. We spend our best thinking on client work, then leave our own offers underdeveloped. We tell ourselves we are too busy, or that our idea is too niche, or that somebody else is better positioned. Meanwhile, the client work keeps the lights on, but it also absorbs every spare hour.

Toby pushed back on the fantasy that online education is passive income. He was right to do it. A course business takes moderation, updates, new content, support, and sales work. In other words, it is still a business.

E-learning businesses need more than course videos

This part is worth expanding because many agencies underestimate how much sits behind a serious learning product. On WordPress, the core course platform might be only the beginning. A real training business may need courses, memberships, recurring payments, reporting, quizzes, assignments, private areas, student groups, social learning features, and email integrations.

That is one reason platforms like LifterLMS have such a wide support library and add-on ecosystem. The core plugin can do a lot on its own, but many projects also need payment tools such as Stripe, PayPal, WooCommerce, or Authorize.Net, plus marketing connections like Mailchimp or ConvertKit, and extras for advanced videos, forms, continuing education, or private-site access. Once we build those systems, we are not shipping a website. We are running an education business.

The payoff can still be real. Toby mentioned a LifterLMS customer who built a successful course about balloon animals. That example matters because it cuts through a common excuse. Plenty of niche topics can sell if the offer is clear and the audience exists.

So the question becomes sharper: should we keep building learning products for clients who may never follow through, or should we put more of that effort into our own products? There is no universal answer, but the conversation made one thing clear. We should at least take our own ideas as seriously as we take our clients’ ideas.

A weak website can cost more than monthly maintenance

One story in the conversation should make every agency owner wince. Kurt helped launch a site for a business with strong potential, built it as an MVP, trained the client on updates, and kept suggesting small monthly services to keep the site alive. Those nudges were ignored.

A year and a half later, the business lost a prospective customer worth about $100,000 a month because the prospect visited the site and thought the company looked weak. The content looked stale. The site looked neglected. The assumption was simple: if the website is outdated, the business might be too.

That lost deal puts low-cost maintenance in perspective. A monthly update package in the $500 to $750 range felt optional until it cost far more than that.

We see this often with agencies and freelancers. We treat launch as the finish line. The client treats the site like a brochure. Then a prospect visits, sees an old blog post, outdated events, or no signs of activity, and chooses the competitor with the better online presence.

A site does not need to be flashy. It does need to look active, current, and cared for.

Better proposals and better pricing change the conversation

Kurt said something that many agencies learn late: wish-list proposals work better than we expect. Instead of pitching only the bare minimum, he now presents tiers that show the smallest possible build, the recommended level, and the full-service version he would choose if the goal were results, not simple launch.

This is the proposal structure he described:

Proposal option	What it includes	Investment level
Bare minimum	Basic setup to get the project live	Lowest
Recommended	The level the agency believes is justified	Mid-range
Wish list	Full-service support, ongoing execution, broader growth work	Highest

The surprising part is how often clients choose the bigger option. Many do not know what is possible until we show them. Once they see a version where they can focus on running the business while we handle the website, content, updates, and marketing support, the higher price can make more sense than the stripped-down option.

Toby added another pricing lesson that many of us need to hear. Agencies often lowball projects, then resent the work, avoid follow-on conversations, and miss the chance to expand the account. A project that should have been priced at $9,000 gets quoted at $4,200, negotiated to $3,000, and then abandoned after launch. Later, the client hires someone else for SEO, CRM setup, graphics, or automation, and that new vendor criticizes the original work.

Upsells work best when they solve the next problem

The strongest upsell example came from a meeting about an e-learning project. The client had scripts but still needed production help. Once Kurt asked whether the team needed support with curriculum and video production, the whole conversation changed. The client felt relief because one more operational burden came off the table.

Then came the pricing reality. If a course needs six hours of finished video, production could take five times that amount in planning, shooting, editing, and review. That moved the proposal upward fast, and the client understood why.

That is how good upsells work. They are not random add-ons. They are answers to the next problem the client already has.

Toby shared a similar experience from The Mighty Mo. A brand copy project led to a pitch for social media help, then strategy, because the person doing the work saw the larger gap. We do not always need a giant service ladder. We do need to keep listening for the adjacent needs that a client may not know how to name.

Conversion tracking helps, but user recordings often tell the clearer story

The episode also touched on conversion tracking, and the takeaway was refreshingly practical. Yes, we can set up conversion tracking in Google Analytics for forms, downloads, and e-commerce actions. Yes, that can help us show movement after changes. But raw conversion data often falls flat for low-traffic B2B sites.

Toby’s point was sharp: if a site only needs a handful of sales a year, it may never generate enough volume for clean trend analysis. Ten conversions across twelve months will not tell the same story as a high-traffic consumer site.

That is where session recordings become more useful. Toby said his team uses Microsoft Clarity, which gives them playback of real visits and heatmap-style data. The heatmaps are less helpful when traffic is thin. The recordings, though, can be excellent. Sitting with a client and watching a real visitor spend two and a half minutes on the site can surface confusing navigation, missed calls to action, and weak page structure much faster than a spreadsheet can.

That work also creates follow-on opportunities. A short review session can produce several hours of new implementation work because the next steps become obvious.

Kurt raised a different but fair use case for conversion tools. Sometimes the data is more useful for the agency than for the client. It helps us show progress, reinforce the value of ongoing work, and make the relationship stickier. He gave a similar example with Patchstack, where monthly security reports help reassure clients that hosting and maintenance are doing real work behind the scenes.

Agency growth is a choice, not a default setting

The final stretch of the conversation moved from tactics to business design. That shift matters because many agencies act as if growth has only one form. More clients, more staff, more projects, more stress. Kurt and Toby both argued, in different ways, that we have choices.

Sometimes we need only a few big wins. Kurt described the relief that comes from landing two or three home-run projects in a year. Once those are in place, the pressure changes. The team can breathe. Project selection gets easier. Saying no becomes possible.

Toby made the same point from a different angle. One agency can be built around many short, efficient projects. Another can run on fewer, larger, longer contracts. Both can work. They are simply different businesses with different staffing models, cash flow patterns, and stress levels.

Kurt’s answer about his current preference was especially clear. He wants fewer, bigger opportunities, enough revenue to keep the team healthy, and enough margin in life to enjoy mountain biking, trail building, and a calmer schedule. That does not mean he ignores smaller jobs. He mentioned taking on a $900 e-commerce project in the same week. It means the business no longer has to say yes to every stressful opportunity that appears.

That is a useful place for many of us to aim. We do not need to become the loudest agency in the room. We need a business model that supports good work, steady revenue, and a life we still want to live.

Final thoughts

The strongest lesson here is not that every agency needs a huge email machine. It is that we need a relevant way to stay in touch with the people who already trust us.

A clean list, useful updates, better proposals, stronger pricing, and a sharper eye for upsells all point in the same direction. We grow faster when we stop treating past clients like closed accounts and start treating them like ongoing relationships.

Spam may have made email feel unpleasant, but that does not make email weak. For many agencies, it is still one of the simplest ways to stay remembered before the next good opportunity appears.