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[00:00:00] Renga: Welcome to episode 4 of the Letter Stack podcast. If you're scaling a newsletter business, you'll eventually work with email outreach and cold emailing.

[00:00:05] Renga: When you do cold emailing, the key is email deliverability—making sure your emails land in the primary inbox.

[00:00:12] Renga: Newsletter businesses are no different. Anthony from Mission Inbox knows this well.

[00:00:19] Renga: Anthony has spent a decade in sales and cold emailing, building an email infrastructure platform called Mission Inbox.

[00:00:32] Renga: He understands that everyone wants their emails to reach recipients’ inboxes.

[00:00:44] Renga: We’ve seen platform outages, and while providers promise deliverability, let’s explore what happens behind the scenes to guarantee inbox placement.

[00:01:10] Renga: Anthony will take us through what it takes to ensure reliability and how you can do it for your own use.

[00:01:23] Renga: Thank you, Anthony, for making time for us. Welcome to the podcast.

[00:01:28] Anthony: Thank you for having me.

[00:01:36] Renga: Before we dive into technical details, can you tell us about your background before Mission Inbox?

[00:01:48] Anthony: I’ve been in sales roles for almost a decade, starting as an SDR. I focused on high-volume cold emailing with good deliverability, making sure lack of responses was about my outreach, not infrastructure.

[00:02:11] Anthony: I built a lead generation and a deliverability consulting business, which we later sold to a customer.

[00:02:22] Anthony: My co-founder and I realized deliverability was getting tougher. Since October 2023, Google has suspended accounts, and last July, Yahoo, Google, and Microsoft rolled out new updates for B2B and personal recipients.

[00:02:48] Anthony: We built Mission Inbox to give users control and visibility over deliverability. Unlike plug-and-play tools, we show what’s happening in the backend.

[00:03:11] Anthony: Mission Inbox lets you manage cold, transactional, and marketing emails in one place, competing with SendGrid or Mailgun, but reducing suspension risks.

[00:03:45] Renga: Many newsletter platforms use SendGrid as the backend. So ultimately, their deliverability depends on SendGrid’s reliability.

[00:04:18] Renga: Can you explain, in simple terms, what happens when an email goes out from G Suite to Outlook? What prevents it from reaching the primary inbox?

[00:05:12] Anthony: First, distinguish cold emails from marketing or transactional emails. Cold emails are mailbox-to-mailbox. Marketing or transactional emails are sent through APIs like SendGrid or Mailgun, authorized by DNS SPF records.

[00:05:54] Renga: Could you explain SPF and other technical terms simply?

[00:06:07] Anthony: Yes. The three key authentication protocols are SPF, DKIM, and DMARC.

[00:06:19] Anthony: SPF is like the mail carrier. I authorize UPS to deliver my letters—like authorizing SendGrid to send emails on my behalf.

[00:06:54] Anthony: DKIM is the seal on the letter, ensuring content wasn’t tampered with. Without it, bad actors can spoof domains.

[00:07:31] Anthony: DMARC is the guard checking SPF and DKIM. It has three settings: None (do nothing), Quarantine (send to spam), or Reject (block entirely). Reject is strict and risky if DNS isn’t configured properly.

[00:09:39] Anthony: So: SPF is the sender, DKIM protects the content, DMARC ensures everything matches.

[00:09:58] Renga: Great analogy. Now, even if these are correct, why do emails still land in Promotions instead of Primary?

[00:10:05] Anthony: Authentication is just the baseline. Deliverability also depends on content quality, list hygiene, unsubscribes, and avoiding spam triggers like “free,” “buy now,” or over-promotional language.

[00:11:00] Anthony: Content should read naturally, like writing to a friend. Domain age, warm-up, and reputation also matter.

[00:12:10] Renga: What about links, images, or HTML-heavy content? Do they affect inbox placement?

[00:13:15] Anthony: Yes. Heavier emails—with images, attachments, or link tracking—are less likely to hit inboxes. The more weight, the higher spam scores.

[00:13:53] Anthony: Google also hides images in new senders’ emails, adding a “show images” banner, which increases the chance of being marked spam. That’s why plain text often performs better than HTML-heavy designs.

[00:15:23] Renga: Good point. But if we can’t reliably track opens because of Apple or Yahoo sandboxing, what should businesses track instead?

[00:17:02] Anthony: Click tracking works better than opens, though it’s not perfect. Some use local setups with custom tracking, but my recommendation is reputation monitoring.

[00:18:20] Anthony: Warm-up tools like Warm.io simulate engagement, boosting domain reputation. They let you test placements across providers—Gmail, Outlook, Yahoo, etc.—so you know where your emails actually land.

[00:20:40] Anthony: That’s more reliable than open rates. You track placement and engagement, not vanity metrics.

[00:20:50] Renga: Makes sense. How bad can it get if a sender skips warm-up and proper setup?

[00:22:14] Anthony: It’s like driving with a foggy windshield—you risk crashes quickly. Without warm-up, spam complaints hurt reputation fast. For example, 10 spam reports out of 100 emails = 10% spam rate. With warm-up and more volume, that percentage drops.

[00:23:40] Anthony: Warm-up also offsets spam reports by simulating positive engagement, improving deliverability over time.

[00:24:49] Renga: Domains also have authority scores. How are those calculated?

[00:25:36] Anthony: Spamhaus provides a tool to check domain reputation. Factors include where you registered the domain, age, blacklist status, and nameserver setup.

[00:27:02] Anthony: Cheap registrars often hurt deliverability. I recommend moving nameservers to Cloudflare. Also, older domains (6–12 months minimum) build more trust than newly registered ones.

[00:28:20] Anthony: Spammers usually buy new domains, so providers score young domains lower. That’s why aged domains perform better.

[00:28:49] Renga: That’s valuable. Now, what tools would you recommend for early newsletter creators who can’t yet invest in Mission Inbox?

[00:29:42] Anthony: It depends. For e-commerce, use Klaviyo—it integrates with Shopify or Magento. For SaaS, info products, or courses, Beehive is a good start.

[00:30:46] Anthony: Beehive uses SendGrid, and while you share reputation with others, it helps beginners who don’t have strong domains. Pair it with placement testing tools like MailReach or GlockApps to monitor deliverability.

[00:32:27] Anthony: Don’t overcomplicate early on. Once you hit 10,000 subscribers, start worrying about advanced deliverability.

[00:32:51] Renga: True. But platforms like Beehive have also had outages. How often should businesses check deliverability?

[00:33:34] Anthony: Between 0–10,000 subscribers, once a month is enough. Personally, I recommend weekly tests—it only takes 10–15 minutes and helps you catch issues before sending.

[00:34:35] Renga: That’s a healthy amount of paranoia for business owners. Any parting advice?

[00:35:01] Anthony: Three things:

1. Set up DNS authentication (SPF, DKIM, DMARC).
2. Warm up domains unless using Beehive.
3. Keep emails text-friendly, avoid spammy words, and run placement tests weekly.

[00:35:44] Anthony: With these, 90% of users will avoid deliverability issues. Advanced tools come later as you scale.

[00:36:00] Renga: Amazing. Thank you for breaking this down simply. We’ll be back with more guests soon.

[00:36:32] Renga: Thanks again, Anthony.

[00:36:39] Anthony: Thank you.

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