The Good, The Bad, and The Spammy: My 2023 Cold Email Guide

Podcast Episode #292

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Show Notes

Have you ever wondered how technology and communication have evolved over the years? In this episode of “WBE Entrepreneur,” I reflect on this topic and share my insights on the effectiveness of cold emailing. I discuss how my cold email strategy has contributed to the success of my current venture, Podsqueeze, and share my recipe for a successful cold email. Additionally, I explain how email providers determine whether a message is spam or not and the process of warming up a new email server to gain trust from potential recipients. Tune in to learn more about the power of cold emailing in today’s digital age.


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The days before the internet [00:01:21]

Tiago reflects on the times before the internet and computers, and how he used encyclopedias and attended a computer course during his childhood.

The rise of email [00:04:34]

Tiago discusses the introduction of email and how it changed the world, allowing people to send letters in seconds.

Email as a crucial tool for Pod Squeeze [00:09:45]

Tiago talks about how email marketing is the main source for new customers for his current venture, Pod Squeeze, and how cold emailing can be effective with the right product.

Evolution of Cold Emailing [00:10:44]

Tiago discusses the success of cold emailing and how he filtered a list of 5 million emails to 500,000. He also explains the recipe for a successful cold email.

Email Marketing and Spam [00:17:16]

Tiago explains how email marketing works and how SMTP servers communicate with each other. He also discusses how email providers use public and internal lists to filter spam.

Reputation and Deliverability [00:20:34]

Tiago explains how email providers use reputation to determine whether a message is spam or not. He also discusses how difficult it is to get off an internal list once you’re on it.

How email servers determine spam [00:21:23]

Tiago explains the technical indicators that email servers use to determine if a message is spam or not.

Options for sending cold emails [00:29:35]

Tiago discusses three options for sending cold emails: lying to email service providers, creating multiple domains and email accounts, or creating your own server.

Creating your own email server [00:30:42]

Tiago shares his experience creating his own email server using a virtual machine and Mail Cow.

Warmup process [00:31:39]

Tiago explains the warmup process, which involves sending a small number of messages to other email accounts to gain trust and avoid being marked as spam.

Mail Reach service [00:32:38]

Tiago mentions Mail Reach, a service that helps warm up email servers and provides information on how many emails went to spam.

Impact of GPT on education [00:35:25]

Tiago shares his experience introducing GPT to English teachers and discusses how it could change education, including the idea of using it to recreate a student’s room.

Links & Mentions

Emails and Email Services:

List of emails of people that have podcasts: 00:10:44

Gmail: 00:19:26

Yahoo: 00:19:26

Zoho: 00:19:26

SendGrid (email or transaction email service): 00:26:42

Amazon SES: 00:26:42

Mailgun: 00:26:42

Gmail: 00:28:39

Outlook: 00:30:42

Zoho: 00:30:42

Yahoo: 00:30:42

Mailcow (service that uses Docker to install): 00:31:56

Mail Reach (website): 00:32:38

Podcasting Tools and Services:

AI tool to help podcasters repurpose their audio content and generate titles, show notes, timestamps, posts, mentions with just one click: 00:13:50

PodSqueeze: 00:13:50

Mailchimp: 00:28:39

Woodpecker: 00:28:39

Spam Emails:

Public lists for spam emails: 00:20:34

Internal lists for spam emails: 00:20:34

Other Mentions:

“The Warmup” (process): 00:31:39

GPT (tool): 00:35:25

Mid Journey (website): 00:36:17

Tiago’s Twitter handle (@wbe_tiago): 00:37:25

Tiago’s email ( 00:37:25

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