#100 Lessons From 100 Newsletters
I bolded a few of my favorite takeaways – if one of these really resonates with you, the numbers align to the articles. You can find the archive of all essays here.
Spend time every week checking in on your community – celebrate members, and pay attention to the sentiment & conversations happening.
List out every assumption you're making in your business about your customers in order to make a research plan to improve your products.
Overwhelmed by ideas? Make a list & prioritize like a product strategist: score each idea by (1) business value, (2) customer value, and (3) level of effort
Leading a community with empathy is good for business, good for the community, and rewarding for you.
Create a culture of safety in your community. When people feel safe, they stay, and they invite their friends.
Spend time in your customer-service inbox & your comments. You’ll build better community-driven products.
Create a community journey map to design an incredible member experience, and upsell at the right moments.
Simplify the community experience through a simple interface, less choices, and less content. You will improve your retention and reduce member overwhelm.
Prioritize community to help you build a long-term sustainable business with more innovation, word-of-mouth growth, and social impact.
Companies that prioritize community are much more likely to be successful.
A sub-community develops when members of a community get creative and come up with other ways to organize, create and support one another. These are powerful – allow them to thrive.
Build personalization into your community experience.
Embody a servant leader mindset. Be willing to throw out your own personal vision to answer the call of your community.
The energy you carry with you and bring to your business and community each day is contagious.
Fostering a community builds relationships that are greater than short-term profits. Serve with integrity.
Treat everything in your business like a product – prioritize, pivot and cancel accordingly.
Understanding and identifying your beliefs is the most freeing feeling in the world. Build community on values & you’ll shift culture.
The key to developing a beloved brand experience is to design consistent, quality experiences.
When you build a community-product you’re creating a social contract with your members.
Community is bigger than online forums or in-person meetups. It's a feeling of belonging. It's smart business development.
True accessible design goes way beyond "compliance". Create experiences that welcome all bodies + people.
Don’t wait for the bad yelp review. Don’t wait for a customer complaint. Experience every aspect of your product as a customer as often as you can.
Make it easy for your members to share their experience in your community.
Give your community something to look forward to so that they stick around – keep things fresh + exciting.
Ascension is a key strategy to grow your revenue and it’s a win-win because it also helps you serve your customers longer, increasing their LTV (lifetime value).
Market the core content & value of your community, but then delight them with complimentary programming & content.
Building a business in service of others isn’t a get rich quick scheme, you’re playing the long game. And community building, my friend, is a long-game.
The biggest risk to your customer retention is that the perceived value of your product doesn’t = the experienced value of your product.
Write a core problem statement for your business – [YOUR CUSTOMER] needs [CUSTOMER NEED] because/so that [INSIGHT OR WHY]
Your product strategy should serve your community at multiple touch points along their transformation.
The more complex a customer journey or product experience, the more points of failure there are.
Do continuous scrappy research – just enough to get you the insights that give you clarity, and ultimately save you time & money.
Add digital products to your service-based business to increase your revenue (at a HIGH margin).
If you can understand your customer's emotional roller coaster, you can better serve them... and in doing so, increase your revenue.
Overwhelming your customers with resources and content so that they don’t leave (it would take ages to get through all this content!) always backfires.
If your product idea is going to have a high business value, high customer value, and it’s easy to do, then prioritize it!
What I've realized about pivots is that every single experience enriches the next, no matter how much of a left turn it is.
The smartest people in the world have more failure stories than fingers + toes.
You can't build a product for your community without involving your community. Build together.
The purpose of mapping your community journey is to recognize the gaps. The gaps help you identify and prioritize your product strategy.
To achieve sustainable growth in your business, it's crucial to focus on serving your customers longer. Do this through additional products, recurring subscriptions, or membership tiers.
You can learn a lot about how to create digital solutions from how people behave in the real physical world.
Gratitude is one of the most important aspects of building a community-driven business. Make people feel heard and appreciated.
Without community features, a membership isn't as sticky and you find yourself on a different hamster wheel ... the content hamster wheel.
1:1s are crucial for understanding the depths of your customer emotions to help you make data-driven decisions.
Don’t build a fan club – build a community.
We are all at risk of our products failing because of our unconscious competence. Don’t forget how much you know – break things down.
Increase your revenue, margins, and build a sustainable business by adding digital products to your service business.
Your members aren’t mind readers and the only person that knows how you anticipate people will behave is you. Set better expectations.
Be wary of bringing in new customers to a subscription product with content or events that aren’t aligned with the core premise of your membership. They’ll cancel quickly.
"When you hit rock bottom in your business, it's your community that gets you through." – Eddie O’Keefe
When you pivot your products or services, a dip is typical. But it’s like anything in life — a little setback can have exponential returns.
The gut feelings with no data behind it are the assumptions that we make in our businesses. Check assumptions with your community to make better decisions.
If you are considering launching a membership for recurring revenue... memberships are a lot of work.
A "sticky" product is a product your customers come back to again and again. Consider what makes your product worth coming back to.
Momentum comes from sharing. But your members are much more likely to share once they've had some indicators of success and growth. Help them get a quick win!
Funnels aren't the best tool for growing a community. Sure, funnels will help you get people in the door. But the key to growing a thriving community is retention.
There are two main membership types: (1) content subscriptions & (2) transformational memberships
“The key to having MORE rewards & less challenges is to start tuning into the symptoms you’re feeling and get clear about the root cause.” – Marissa Liesen
Pretend your community member is a tourist. How would you show them around & create a fun experience?
The quality of our relationships determines the quality of our lives. Prioritize accordingly.
If you’re building a business, you don’t have to do it alone. Find your people!
Want to avoid burnout in your business? Price your services and offers appropriately.
The most important community KPI, which is hard (read: time consuming) to track, is sentiment.
You shouldn't build a membership based on one person's experience building ONE community. Just because it worked for their community, doesn't mean it will work for yours.
Marketing is easy if you build the right thing.
The best thing you can do for your business growth is track important metrics (KPIs) every month. You'll see progress you didn't realize was happening, and recognize your gaps.
Curate incredible experiences, help your members connect with one another, and charge for it.
If you want more of your students to “do the work”, consider different learning styles. Are you doing everything you can to help your members be successful?
We need to strike a balance between routine and experimentation.
Develop your community transformation statement to design a better experience. We take members [from A to B].
The overlap between the problem you solve, and the community values you hold, are how you attract aligned members to your community.
One of the biggest mistakes I see with beta programs is that they will provide only part of a course. How will you know if they get the intended results?
Start a conversation with your customers. You might get product feedback. You might get a rave review that you can use as a testimonial. Win, win.
Your messaging matters. “There’s a famous quote that says, “Words create worlds.” and I’d love to amend it to also say “Words create community”. “ – Cheyenne Buttrey
The best way to get active community members for life is to give them immediate and frequent wins when they join.
Strengthen the identity and member experience of your community. When you make these updates you may lose some members... but you'll also attract more of the right members and be on a better path for growth.
Take a vacation. Your community will support one another while you’re gone.
A powerful question to ask your community – "What is one thing that is working really well for you right now?"
Focus on building relationships and your business will grow.
Service businesses have SO much good data to build an incredible digital product. Think: template packs, course, live program, playbook, etc.
After working with founders of all stages and fortune-500 companies launching new products I can confidently tell you that NO ONE gets their product right on the first launch. There is always room for improvement.
Choose the right product experience (course, program, mastermind, etc) by aligning it with your customers' needs, your preferred way of showing up, the time required for transformation, and how it aligns to your customer journey.
Pop-up communities can be a huge word-of-mouth driver for your business or project. Try using one for your program, challenge, events, or grassroots initiatives.
Connecting with your community will lead to stronger customer relationships, repeat customers, the development of better products, and unimaginable growth.
Your marketing funnel is often the first product-like experience with your brand. It's SO important that it is an incredible experience so that you build trust.
If you want a specific type of engagement in your community, you need to set expectations throughout their customer journey.
No one gets their product right the first time. It takes iteration and co-creation with your community to build a winning product.
Your audience size should impact your product strategy... meaning how you detail and price your products.
Scale slow + steady to build a successful membership. Use member feedback to drive programming and updates.
Facilitated workshops, when driven by data, can have HUGE impacts on your business. It creates space in the business for innovation to occur, and creates an opportunity to collect data you're not looking at regularly.
2024 highs: We launched Affinity, I went on amazing retreats, my husband joined the business. 2024 lows: I made a bad hire, we struggled with personal finance, I burned out.
My top predictions for community products in 2025 are that (1) cohort programs are in (again), and (2) In-person events are necessary for any online community.
Maximize "the overlap"—the small group that engages in both content and community—by streamlining the experience, reducing overwhelm, and guiding students to the most essential program elements.
TikTok communities are special because they thrive on hyper-personalized algorithms, niche subcultures, and authentic brand-user interactions, creating a space where anyone can find their people and be part of the conversation. – Guest Jessica Jones
Self-organized retreats are awesome for building relationships, a looser agenda, and for keeping expenses low.
You only need to sell what's needed to make a purchasing decision. Then, blow them away with experience. That’s how you create a word-of-mouth flywheel that grows your product for you.
A well-designed onboarding experience is more than a welcome email—it’s a strategic journey that guides members step by step, builds habits, and helps them reach their first “aha” moment as quickly as possible.
Nothing bad can come from writing 100 issues of a newsletter – you can expect better (+ faster) writing skills, and a whole lot of personal growth.
If you loved this, you can subscribe to the weekly newsletter here for free! I send a bunch of resources & share a bts happenings of my business in the email version.