Weekly Q&A: Audience Growth, SaaS Emails, and Building Kraken
Greetings from Amsterdam 🇳🇱
Welcome back to another weekly update where I start with answering the questions you submit in the replies, then take you behind the scenes of growing my AI Writing Skool community to 10,000 members.
Today we’re going to cover:
Audience questions about platform saturation and email frequency for a SaaS business
The current bottlenecks in our business and what we’re doing to remove them
Key metric growth across our social media & email lists
Building Kraken, our internal AI agent, and my current YouTube content flywheel
The latest Invest Like the Best episode with Cliff Sosin
And if there’s anything you want me to cover or questions you want an answer to, make sure you leave a reply down below so I can cover them in the next update.
Also if I end up answering your question, I’ll send you over a Starbucks gift card as well.
Now let’s get into it.
Audience Q&A
This week’s Starbucks gift card winners:
Daniel Urdaneta from YouTube
Matthew Harrington from YouTube
If you’d like your question answered in the next update (and get a Starbucks gift card for doing so), leave it in the replies below.
Now, let’s get into the questions.
1. Are X and LinkedIn reaching a saturation point?
Loving the Rays shirt!
Question for you: Have you and your team considered that both you and Cole might be reaching a saturation point with your audiences on LinkedIn and X?
If the goal is to hit 333 new subscribers per day, my hypothesis is that the growth needed to get there might actually come from platforms like Instagram and TikTok.
I completely understand that those platforms require significantly more effort, especially when it comes to filming content consistently. But if you're already approaching a ceiling on LinkedIn and X, I feel like expanding to new platforms would be the logical next step, rather than just producing more and better written content for the same two channels.
So I'm curious about your reasoning: Is there something about Instagram and TikTok that makes you believe they wouldn't be effective channels for reaching that goal? Or is there another reason, beyond the additional effort required, why you haven't prioritized them?
Here’s how I am thinking through the ways we can accelerate our email list growth:
Do I think Daniel is right that our Start Writing Online email course has hit “saturation” with our current followers on X and LinkedIn?
Well, we’ve been running that exact same email course, with precisely zero updates to the landing page or funnel, for about 4 years now.
While we still continue to collect email subs on those platforms, the pace of collection is definitely lower. So this is definitely a possibility, though it’s hard to measure quantifiably.
Let’s assume that the answer to this is “yes” meaning we will need to do something different to hit our email goal.
So the next question then becomes: what should we do to accelerate? I think there are three options:
We could invest more in creating even better content on X & LinkedIn to see if that alone accelerates things.
We could create a new, refreshed email course and resume posting on our current platform.
We could keep our current email course and expand to Instagram/TikTok which will involve learning an entirely new platform.
When I look at these three options:
The first one is the least amount of additional work and change to our process. We would just build a better system for tapping into what is “working” on these platforms more effectively than we are doing now.
The second requires some upfront work, but ultimately little change in our process afterward.
The third requires signing up for net-new ongoing work to create standalone video content, which would be a bigger change to our process.
Ultimately, I think the answer will be we need to do all three.
I think first we need to invest more time specifically on our LinkedIn content, which has primarily been a repurposing cadence for the last year or so. This would require about 4–6 hours of research to see what is currently working best across that platform, then applying it to our niche.
Then, we would gauge the impact of that additional investment. There’s a world where just creating better posts gets us close to that goal. But if we don’t see much acceleration in conversion (but we get an increase in views), that would suggest the email opt in has been seen too often by that audience. This would suggest updating our email course for the platforms we’ve been publishing the longest, primarily X and LinkedIn as Daniel suggests.
Then after doing those two things, we would then reevaluate to see how close we are to the goal. My hypothesis is that we could get somewhere close to 200-250/day if we made both of those upgrades, but would struggle to hit 333/day without adding in an additional platform. But I would rather squeeze the most juice out of what we’re currently doing before signing up for something new.
So to summarize:
We can only know we’ve hit “saturation” of an opt in if we first look to accelerate the growth on that platform and find that email subscribers do not keep pace with the growth in views (meaning the viewers have already seen the email course).
From there we would create a fresh opt in (which we are already planning to do), creating a fresh conversion mechanism for everyone on that platform.
Once we’ve done those two things, we would evaluate whether or not we need to expand hard into short-form video (which we do plan on doing anyway, as that is our most underserved audience).
Hope it’s helpful to see how I think through something like that!
2. How often should a SaaS business email new users?
Question- what would you recommend for an email sending frequency (especially during the first 30-60 days) for a B2C saas. I learned (and found success) on daily emails in the info space, all with story emails that have a cta. Is daily or even 3x a week too frequent for a SaaS business focused on hyper scaling?
For context the initial sign up is free, purchasing something is an optional activation point but not necessary for usage
Here’s the exact email cadence we use for Typeshare:
We have a 5-day onboarding sequence for all new free users. The goal of this is to show them around the product & soft CTA for them to upgrade to paid.
If someone upgrades at any time during that email course, we pull them out and put them into a separate “paid member” onboarding that shows them how to use all of the paid features
After the initial 5-day email course, if someone has not upgraded, we then have a 3-day “FOMO” sequence where we have a harder pitch to upgrade with more social proof, price anchoring, and feature-benefit breakdowns
After either onboarding concludes, we then drip them into a 2x/week newsletter that roughly sorts into:
New feature announcements
Social proof showing members seeing success with the product
For both of those emails, we use Liquid logic to show the right CTA depending on if that person is a free or paid member:
For free members, we CTA to upgrade
For paid members, we CTA back to the app to keep them using it
This is working well for us at the moment. The next improvements we would make to this would be:
Testimonial gathering sequence. Once someone has been a paying member for 2 months, we would send them a survey asking them to share their feature ideas & feedback + rate their experience on a scale of 1-10. If someone gives us an 8+, we would ask them on the spot to submit a testimonial to use in our marketing. We would then have an agent summarize all of the feature requests and submit them to us on a weekly basis.
Churn winback sequence. If someone churns, we would start a 30-60-day winback sequence where we offer them a free trial to get started again, share some of the features they might have missed, and add more social proof of others who are seeing success as well.
In terms of having a daily email newsletter for SaaS, I can’t speak to whether or not it would work as well as info.
If I were you, I would increase the frequency in stages from 2x/week to 3x/week, then 4x, etc. and gauge the relative improvement with each email send as a percentage of the total subscriber base.
But I would only think about the ongoing newsletters once you dialed in the onboarding sequences for both free and paid
Hope that helps! Happy to answer any more questions on this if you have follow-ups.
Business Bottlenecks
As a reminder, the next milestone in our business is 1,500 active AI Writing Skool members. I talked about how we set that goal in my first weekly Q&A video.
And there are only two things we need to do to make that happen:
Put on periodic, highly-educational, community-exclusive events to both attract new members and retain current ones
Generate a consistent stream of new email subscribers who we can tell about the community
Everything that does not directly contribute to one of these two priorities is a distraction.
Until those goals change, I will keep using this update as a forcing function to talk about what we did to move them forward each week.
Focus #1: Putting on highly-educational live events
This week we started the process for marketing our upcoming Start & Scale Your Newsletter Sprint. We’re up to 64 new trials started for this sprint with 9 more days of marketing to go. We expect this to come in around 250-300 new members while getting at least 2/3 of our current member base signed up to participate, which would be a home run.
Since we’ve already run this sprint ~4 months ago, there is nothing net-new we need to create on the marketing or curriculum side. That allows us to spend more time on the live event that is coming immediately after that we will reveal closer to Black Friday 👀
Then we also generated the first few enrollments for our January Ship 30 for 30 cohort, which is the third upcoming event we have scheduled.
Between these three events, we have plenty on the docket to both attract new members and retain our current ones, which will set us up nicely heading into 2027 where we will expand both the frequency and breadth of topics for our live events. Stay tuned next week where I’ll break down how we’re thinking about approaching that from an operational perspective.
Focus #2: Generating more email subscribers
The target from last week still stands: roughly 333 new email subscribers per day is what gets us to our membership goal over the long run.
Finishing up the curriculum and operational setup for the 3 events we have upcoming frees up a ton of time to reinvest in hitting this goal. Sometimes it’s fine to have a goal but leave it on “maintenance mode” until you have enough time & attention to dedicate toward its pursuit. And that’s what we’ve done for the last ~6 weeks since we started tracking this goal more closely.
I laid out the exact plan we are going to follow in my answer to Daniel’s question in the Q&A section. The first step is to pull our last 120 days of LinkedIn posts, plus some of the best performing posts from others who do well on the platform, and see what we can apply to the content cadence we have set for this week.
All the while, we will continue the newsletter, video, and social posting cadence that is keeping us around ~70 email subs per day.
Metric Growth
Email list growth
Last week we averaged just 37 email subs per day, which is way off our long-term goal of 333/day and below our recent average of 57/day.
A few days had particularly low readings as a few of our LinkedIn posts received almost no distribution, so we’re going to dig into that this week and figure out what’s happening.
Social Growth
We continue to chip away toward 500k on X +196 there this week
We continue to chip away toward 200k on LinkedIn +83 there this week
We resumed posting on Instagram with some clips from these weekly updates, so we’ll see what that does to our follower growth over the coming weeks
And YouTube hits its first inflection upward toward 10k as our most recent video is a 1 of 10 on the recent performance scale. Onwards!
AIWS member growth
We made some CRM changes and found some undercounted members, so week over week it looks a little different if you’re comparing it with previous updates. But the change using this new calculation is correct.
Over the last week we net lost 28 members, which we expect to happen as we lap a round of renewals from the current Ship 30 cohort. This is happening simultaneously with our front end promotion being a free trial, rather than a paid $99 subscription.
When this happens, we don’t count the trials as new members until they make their first payment, so we expect net member additions to be negative for the next couple of weeks before inflecting back upward toward the end of November as we resume a normal $99/month paid promotion.
Miscellaneous
Building Kraken, our internal AI agent
This week I started the process for building out an internal operations agent named Kraken.
Long-term, I want to create a team-wide shared agent that is constantly working to identify small operational tasks that it can take over and automate. As our business continues to grow, I expect our operational complexity to increase slightly as we run more events & have different tiers within our community. The goal of this agent is to get out in front of that bottleneck before operational bandwidth limits our growth.
To start, I connected it to our business dashboard so it can answer any questions our team has about any of our business metrics.
Building that simple feature made me realize I need to step back and think holistically about:
Where we store all of our data to make sure all tools can connect it
How we organize our active projects in notion so they know what’s being built
Having some kind of master business context also stored in notion that the agents can read and understand
I’m going to invest time in building this out toward the back half of this week and will update you guys on the progress in next week’s update.
My current YouTube flywheel and the pillar piece method
I’ve reached a point of consistency in my weekly content creation process, which feels great.
I’ve published 1-2 newsletters and YouTube videos every week for 12 weeks in a row now, only missing 1 week when I was moving my entire life back across the pond to Amsterdam.
Now that I’ve built this consistent cadence, my next goal is adding leverage to extract as much as possible from the long-form pieces I’m creating.
A great example is the Q&A & Miscellaneous section of this newsletter. Since I am filming these as YouTube videos, I can immediately slice these sections into 4 standalone shorts, one for each question I answer or point I cover. These went live on my Instagram this week, plus I cross-posted them as YouTube shorts.
The next step is to build the same system for my other weekly newsletter/video, which is typically an educational deep dive. I want to extract a handful of additional shorts from those, some of which will be sliced off clips, and others will be standalone compressed versions of a section or the full video.
We’ll be breaking down this entire process in a live event coming soon over the next few weeks, so stay tuned for that invite 👀
Media I’m Enjoying
I enjoyed this recent Invest Like the Best with Cliff Sosin. A lot of the conversation was focused around what becomes more valuable when intelligence is free, which is a topic I’m thinking a lot about at the moment.
https://www.youtube.com/watch?v=EH6DsNT455M
I also cranked through a lot of work this week with this Marsh set in the background. Pair with a couple espressos for maximum effect.
http://youtube.com/watch?v=oUNvoX8c1Oc&list=RDoUNvoX8c1Oc&start_radio=1&
Thanks for being here!
That’s it for this week’s update - and I’d love to hear your feedback.
Do you enjoy these types of updates?
Any topics / areas you’d like me to cover?
Anything else you’d like to share with me?
Leave a reply and let me know - I read and respond to every one of them.
ALSO - if you have a question you want answered in the next update, please ask it below.
As a bribe, if I answer your question next week I’ll send you a virtual Starbucks gift card as a thank you for asking a good one.
Talk soon,
Dickie
PS: If you want a full guide to writing long-form articles like this on the internet, here’s a free 13,000-word Ultimate Guide to help you get started.
