Building a Winning Hand: The 8 Email Types That Drive Growth
Introducing the Business Growth section of Timeless Leader
This is the first post in a weekly deep-dive into the systems, strategies, and frameworks that drive sustainable business growth. As I’ve said earlier, "2025 is the Year of the Email" (and you’re probably seeing this as an email), therefore I'm kicking off with an 8-week series on email as a growth lever – before expanding to other business growth and organizational leadership topics.
In Tuesday's post about moss, I explored how time may be money, but money isn’t time. Email follows similar laws: Trust compounds slowly. Permission can't be purchased. Organic beats synthetic. But when you respect these principles, you build something that works while you sleep.
This is the first post of an 8-week special on email strategy to kick-off the “Business Growth” section of this Substack. You can manage your subscription settings to individual sections by clicking this button:
The Random-Card Problem
Most small businesses are playing email with random cards, hoping for a winning hand. They might send newsletters, or bursts of cold outbound, or use the default transactional confirmations. There’s little automation, limited opt-in and segmentation, and there’s a lot of manual work.
Small wonder why email isn't the growth engine of their dreams.
The problem isn't that email doesn't work.
It’s that it’s done haphazardly, inefficiently, and it’s probably missing entire suits of cards that could fit perfectly to the situation.
I've learned this lesson repeatedly over the past 15 years – from newsletters for my first company and Game-Based Learning NYC, to mapping customer journeys at Box with Lauren Vaccarello, to working with startups and coaching founders and agency owners in Alex Berman's cold email mastermind.
What does it look like playing email with a random hand?
One founder I worked with had >40K contacts in her CRM but only 900 were actually marketable after cleaning. That's 97% waste – and a massive missed opportunity.
Email isn't just another marketing channel. It's the backbone that ties everything together. You still need calls, meetings, and social media. But email is where you build systematic, scalable relationships that compound over time.
It's where leaders create leverage.
The 8 Essential Email Types
To begin building a more strategic hand (and to start this series), it helps to have a comprehensive cataloging of all the email types that businesses need.
Lucky for you, I’ve compiled the list:
Cold Outbound First-contact emails to prospects who don't know you yet. Built to start conversations, not make sales. Follow-up sequences (2-5 emails, occasionally more) nurture until they're ready to engage.
Marketing Emails Regular communications to your opted-in audience. Newsletters, educational content, announcements. These build brand loyalty and keep you top-of-mind.
Sales Sequences Strategic series nurturing prospects through your buying journey. Each email builds on the previous, addressing objections and creating urgency.
Automated Lifecycle Emails Behavior-triggered messages: welcome sequences, onboarding flows, abandoned carts. Highest ROI because they hit at exactly the right moment. Welcome sequence recipients yield 51% more revenue than single email recipients, according to Mailchimp.
Transactional Emails Order confirmations, shipping updates, password resets. Recipients expect these, giving them high open rates. Smart businesses incorporate extra value-delivery and subtle cross-sells to make these higher impact.
Personal Emails One-off, manually crafted messages for high-value relationships. Thank you notes, check-ins, congratulations. In an automated world, personal touch creates exponential impact.
Survey & Feedback Emails Post-purchase surveys, product feedback, review requests. Double benefit: gather intelligence AND show you care.
Community & Event Emails Invitations, webinar notifications, community highlights. Essential for businesses building relationships beyond transactions.
Each of these email types serves different purposes, and looks different to implement.
We’ll spend more time digging into them in coming weeks.
But first:
The Permission Foundation
Before implementing any email type, understand: Permission is everything.
Warm relationships need explicit opt-in. Cold outbound operates under "legitimate business interest" – but relevance is non-negotiable. CAN-SPAM and GDPR aren't just compliance – they're good business. Nothing kills sender reputation faster than complaints.
No matter what email type you’re considering, investing in the 2-way relationship and explicit opt-in is essential. It’s even the entire focus of Tarzan Kay, an email marketing leader I deeply admire.
Your Next Move (Based on Where You Are)
Like moss, a healthy email ecosystem takes time to grow. You can't blow up someone else's list and transplant it to your business. But unlike moss, email compounds and accelerates – each permission you earn, each relationship you nurture, multiplies your future impact.
Here are three options for how to proceed, based on where you are today:
If you're just getting started: Set up a newsletter with clear opt-in and simple maintenance. This builds your list AND the habit of communicating regularly. Don't overcomplicate it – one email type done well beats eight done poorly.
If you have an emerging program (2+ types shipping consistently): Audit before you add. Pick one existing email type that's critical to your business and ensure it's running as intended. Consider temporarily pausing less important emails to focus on perfecting your core ones (especially transactionals – they're non-negotiable).
If you have a mature program (4+ types consistently driving measurable outcomes): You've got two paths:
Add another email type strategically
Optimize what's working (tool upgrade, improved messaging, tighter segmentation, or better integration between email types and other channels)
Pick ONE improvement and create a 6-week project plan to implement it.
The businesses crushing it in 2025 aren't sending the most emails. They're sending the RIGHT emails at the right time to the right people.
So – which stage are you at, and what's your next move?
Email me. ;)
-Joe
PS. Next week I’m running a special promotion for our Basecamp membership for the July 4th weekend. Keep an eye out for it! 🇺🇸