If you’ve ever launched a course, membership, or product and wondered why your people aren’t engaging with the resources you worked so hard to create, this snack-size episode is for you. Pulled directly from a live Q&A inside the Educators Lounge, this conversation with Tayler Cusick-Hollman reveals what really goes on after the sale.

During our call, Tayler highlighted that many of us are facing similar issues in the education space, where we struggle with onboarding, retention, and having to spoonfeed your community—even when it feels redundant.

We also dig into the mindset shift that needs to happen after the sale. Because keeping people engaged is just as strategic—and important—as getting them in the door in the first place.

We put so much effort into launching: building funnels, perfecting messaging, and creating amazing content. Then when that sale comes in, we celebrate!

But what often happens next? Often silence.

And suddenly, we’re in our heads wondering why our new members aren’t as hyped about our program as we are. Why aren’t they showing up? Why aren’t they interacting?

The hard truth: the sale is only the beginning. What comes next is a different kind of work.

The simple but game-changing truth? Just because the thing is there, doesn’t mean people are gonna know it’s there.

While sharing about my own experience with building a membership, I asked our members to also chime in with their own. Tayler is building a membership around a low-cost software product (Enji), which means she’s had to be especially thoughtful about member retention. Her biggest lesson? We all need to be spoonfed.

Yep. Even if it makes your inner educator roll her eyes. Even if it feels redundant. Because people are overwhelmed, distracted, and juggling a million things.

If you want them to experience the transformation you promised, you have to guide them through the process. Step by step.

You might be thinking, “Shouldn’t they just read the welcome email?” or “Isn’t it obvious what to do next?”

But think about your own habits. How many programs or courses have you purchased and never opened? How many community platforms do you ignore because no one is actively prompting you to come back?

This isn’t about being patronizing, it’s about creating clarity and ease. Your members aren’t lazy, they’re just human, and humans need reminders.

So tag them in the group. Send the extra email. Create that “Start Here” guide—even if it feels like you already said it.

Repeating yourself doesn’t make you a bad educator. It makes you a smart business owner.

Tayler dropped a term that more creators need to know: retention marketing.

It’s the marketing that happens after the sale. The nurturing, the reminders, the personalized check-ins. It’s onboarding with intention. It’s engagement that feels personal. It’s all the things that keep people coming back—not just for the content, but for the community and transformation they signed up for.

If your members aren’t engaging, it’s not a personal failure. It is a cue to revisit your systems.

Are you assuming too much? Are you relying on a one-time welcome sequence instead of an ongoing strategy? Are you prioritizing post-sale support the same way you prioritize launch week?

It’s not about doing more. It’s about doing the right things, consistently.

Mentioned in this Episode

layleeemadi.com/educatorslounge

Connect with Tayler

enji.co

instagram.com/enji_co

instagram.com/taylrd_designs

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Ever wonder how conference speakers actually get chosen? I’m pulling back the curtain with one of the most sought-after event hosts in the creative industry.

In this episode, I’m joined by my friend Kellie Penn, founder of The Reset Conference, for a candid conversation about how speaker applications are reviewed, what makes someone stand out, and what instantly lands an application in the “no” pile. Kellie shares her exact selection process (yes, including the color-coded spreadsheets), the role relationships play in getting booked, and how she balances fresh faces with returning favorites. We also tackle the ever-debated topic of speaker compensation for individually run events versus corporate conferences.

The Reset Conference started as a way to help photographers run their businesses without sacrificing their lives in the process. Kellie’s own burnout led her to rethink the “hustle harder” message she kept hearing in the industry.

While The Reset Conference primarily serves women in photography, its content balances creative inspiration with solid business strategy, making it a place where attendees don’t just learn how to take better photos, but how to run sustainable, profitable businesses.

That heart-centered mission influences everything—including how speakers are chosen.

Kellie reviews every single application herself. Here’s what happens:

For Kellie, it’s like a big puzzle. Names go on, come off, and switch around. Considerations include diversity, variety, and what the attendees most want to learn.

One of the biggest myths Kellie debunks? That you have to “know someone” to get booked.

Yes, relationships matter—but not as a gatekeeping tactic. If Kellie knows you’re an active supporter of her event, that you’ve attended before, or that you’ve spoken positively about it in other spaces, it helps. But every year she books people she’s never met.

Her tip for building genuine connection: Attend the event before you apply, introduce yourself, and join the welcome events. Being visible and engaged goes a long way for an event host.

Instant Green Flags:

Instant Red Flags:

Running an individually owned conference is a financial risk. There’s no corporate budget or membership fees—it’s one person (and their family) signing venue contracts and covering costs. This plays into the overall budget for the event and determines financially what’s an option for the event.

When it comes to speaker compensation at The Reset Conference, here’s how it’s handled:

“It’s not just about a check,” Kellie explains. “The value comes from connections, visibility, and the ability to make the most of being in the room.”

If you want to one day speak at Reset, Kellie’s advice is simple:

When you align your message with the heart of the event, you don’t just increase your chances of being booked, you also ensure that your time on stage truly serves the people in the room.

Want to become the kind of speaker event hosts are excited to put on stage? My Sought-After Speaker System shows you how to craft irresistible pitches, build relationships with organizers, and create signature talks that make you the obvious choice.

Mentioned in this Episode

The Reset Conference

Sought-After Speaker System

Connect with Kellie

The Reset Conference

instagram.com/theresetconference

acrossthemilesphotography.com

instagram.com/kelliepenn

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Ever feel stuck trying to decide if your membership should be monthly, six-month, or annual? In this snack-sized episode, I’m sharing a real coaching moment from inside The Educators Lounge where we unpack how to confidently set your membership commitment length and how to communicate it so potential members feel supported, not trapped.

This conversation started with Brooklyn Grotte, a Lounge member preparing to launch her first membership, and her question about choosing a timeframe sparked a deeper dive into the strategy and psychology behind it.

This episode one was pulled straight from a recent live Q&A inside The Educators Lounge—our monthly gathering space for business-minded educators who are building programs, memberships, and education-driven offers with intention.

Mentioned in this Episode

layleeemadi.com/educatorslounge

Connect with Brooklyn

brooklynphotomn.com

instagram.com/bizwithbrooklyn

instagram.com/brooklynphotographystudio

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From $40K a month on Etsy to $1.3M a month in coaching and education, Dylan Jahraus has figured out what works for her audience.

I met Dylan Jarris at a mastermind in Nashville, and within five minutes, I knew her story needed to be on this podcast. She’s an e-commerce powerhouse with 13+ years of experience who turned a wedding DIY project into a seven-figure Etsy business—and then scaled into a multimillion-dollar online education company.

In this episode, we talk about what really goes into scaling, the mindset that sets successful educators apart, and why burnout wasn’t a mistake, but instead a catalyst. Dylan shares how her corporate background shaped her Etsy success, why long-form content is non-negotiable, and what most educators get totally wrong about audience growth and sales.

Mentioned in this Episode

Hayley and Doug – americandreamrevival.com

Sunny – sunnylenarduzzi.com

Alex & Leila Hormozi – acquisition.com

Connect with Dylan

dylanjahraus.com

instagram.com/DylanJahraus

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Are you offering too much inside your program or membership and still wondering if it’s “enough”?

If you’ve ever found yourself piling on more calls, more downloads, more content just to prove your value… this quick conversation with Geily Romero is your permission slip to stop the overwhelm, both for you and your members.

This episode one was pulled straight from a recent live Q&A inside The Educators Lounge—our monthly gathering space for business-minded educators who are building programs, memberships, and education-driven offers with intention.

Geily asked what advice I’d give to someone one year behind me in the membership journey and we had a great conversation about practicing patience, avoiding burnout by over-delivering, and letting your data guide your next move.

In the beginning stages of building my membership, I did what so many of us instinctively do: I packed it with everything. Weekly calls, downloadable resources, bonus trainings, templates. You name it, I added it.

Why? Because deep down, I was afraid people wouldn’t see the value unless I over-proved it. But here’s what really happened:

More wasn’t more. It was too much.

The moment things shifted was when I started asking myself a different question: What if this was already enough?

When I stopped “stacking” my membership with content just for the sake of it, three things changed:

Geily echoed this in our Lounge call. She shared that she initially planned to offer everything under the sun, but when she paused and simplified her structure: just two calls a month and a few core resources—she realized that no one was asking for more.

That’s when it clicks. People didn’t need more. They needed clarity.

Another piece of advice I offered? Track what your people are actually doing.

Because your gut will lie to you. Your inner perfectionist will whisper, “It’s not enough.” But your metrics will show you exactly what’s working and what’s not.

So before you make your next move, pause and look at the numbers. Let them guide you instead of your worry or assumption.

One of the most important things I’ve learned over the last year is this: patience is not passive. It’s a strategy.

The people who build long-term, intentional, value-rich memberships aren’t the ones sprinting to over-deliver from the start. They’re the ones testing, learning, adjusting, and letting their community shape the evolution of the offer.

Your membership isn’t static. It’s a living, breathing project. And that means it’s okay to start small, to simplify, and to grow over time.

This might be the most freeing realization of all.

You don’t have to prove your worth with excess. You just have to deliver what your people actually need—clearly, consistently, and without burning yourself out.

Less can be more. And more importantly: it can be enough

Mentioned in this Episode

layleeemadi.com/educatorslounge

Connect with Geily

cuttingedgefinancialsolutions.com

instagram.com/cuttingedgefinancialsolutions

cuttingedgefinancialsolutions.com/the-profitable-circle

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What really happens when you launch your first a membership with no expectations? In this episode, I take you behind the scenes of The Educators Lounge, my very first membership space, for a full one-year recap.

I launched this community with zero expectations (and a ten-member goal!) and ended up with over 80 signups in the first week. Since then, it’s been a journey of learning, restructuring, and intentional growth, not scale. I get real about what worked, what flopped, what I’d do differently, and what’s next.

Before The Educators Lounge, there were courses, coaching programs, and my annual conference. Every single time, the same pattern emerged: everyone would come in energized, collaborative, excited, but then left with no real way to stay connected.

I knew educators and creative leaders like us needed something ongoing. A space that wasn’t just about learning, but belonging. Somewhere we could show up as both experts and learners. Somewhere we didn’t need to pretend we had it all together.

That’s where The Educators Lounge came in. It wasn’t just another content dump, but a container for connection.

When I opened the doors, here’s what members got:

It was stacked. It was generous. And it was… a lot.

First, let’s talk about what went well!

My goal was to welcome 10 founding members. I ended up with 84. That initial traction showed me there was a hunger for this kind of space. While I was thrilled for the success, I was also terrified, because I take this responsibility seriously. These weren’t just “signups,” they were people entrusting me with their growth and connection.

Despite all the trainings and perks, our surveys told a clear story: people joined for the relationships. The best parts of the membership happened in our group calls, community posts, and peer shoutouts. The people made this space what it is.

We created a suggestion box and made it part of our system. When members asked for changes (less content, more networking, new formats), I listened. When we couldn’t implement a request, I explained why. That transparency built a lot of trust.

Out of our 84 founding members, 74 stayed through the full year. And we gained more members by word-of-mouth alone, without any relaunches. That kind of retention means more to me than any flashy growth stat.

Weekly calls, constant new content, spotlighting members—it sounded like a dream on paper. In reality? It created content fatigue. People felt overwhelmed. I felt overextended. So I stripped it down and swapped some of those content-heavy sessions with networking calls—and the results were night and day.

I loved the idea of inviting members to lead sessions. When everyone’s schedule is packed, volunteer-led trainings just don’t land the same. We paused this format and are now experimenting with new ways to showcase member expertise that doesn’t rely on live teaching.

I wanted the community platform to feel alive between calls. The reality is: when a platform isn’t part of someone’s daily routine, it’s easy to forget. I’m working on gamification, reminders, and challenges to nudge that consistent engagement, but it’s still a work in progress.

We’re not scaling fast. We’re scaling right. Here’s what’s staying, shifting, and evolving:

What’s Staying:

What’s Evolving

Still Testing:

The suggestion box? It’s not going anywhere.

One thing I did when launching The Educators Lounge was set a one-year commitment for myself. I gave myself the permission to shut it down if it didn’t feel aligned. That safety net helped me stay creative and flexible without being locked into something that might not work.

One year in, I can say with complete confidence: this is working. This space matters. And it’s not going anywhere.

We’ve seen members land speaking gigs, grow their businesses, collaborate on events, and support each other in ways I couldn’t have imagined. And the ripple effect of that will only keep growing.

If you’re ready for this type of community, we’d love to see you inside The Educators Lounge!

Mentioned in this Episode

The Educators Lounge

Kajabi

Creative Educator Conference

Sought-After Speaker System Course Waitlist

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Want to land your dream speaking gig? It starts with your pitch.

As someone who coaches and curates speakers, I’ve seen what works—and what totally misses the mark. In this snack-sized solo episode, I’m breaking down what makes a speaker pitch stand out in a sea of applications. This topic is especially top-of-mind because applications are now open for the Creative Educator Conference—my own annual event—and I’m getting an inside look at what people are doing right… and wrong.

I also share a little behind-the-scenes update on my upcoming course for speakers, The Sought-After Speaker System. Whether you’re pitching for my event or anywhere else, these tips will set you up for success.

This might sound obvious, but you’d be shocked how many people don’t do this. A pitch should feel like it was written for me, not just sent to me. If you’re applying to an event, mention the name of the conference, reference their mission, and align your values with their audience.

Example: “The Creative Educator Conference’s emphasis on community and authentic teaching is exactly why I want to be part of it.”

That single sentence shows me you’ve done your homework and that you care about my audience, not just the opportunity.

Your talk might be amazing, but if you can’t clearly show why it matters to this specific audience, you’ll be overlooked. Hosts are scanning for fit—make their job easier.

Instead of: “I want to speak about scaling a creative business.”

Try: “I want to share three actionable strategies for scaling a creative business without sacrificing creative integrity—something I know your audience of educators and artists values deeply.”

That’s a fit. That’s a match.

You don’t need a TEDx talk under your belt to be taken seriously. Hosts just want reassurance that you’re confident and capable on stage. If you’ve done workshops, podcast interviews, webinars, or even saved Instagram Lives—share those. Include a link to your speaker page or attach a short clip if the application allows it.

Proof builds trust. Even if it’s informal, it’s better than nothing.

Too many pitches end with a mic drop—or worse, a stiff “thank you for your consideration.” Don’t close the door. Invite the host to explore with you. If there’s an optional field on an application, use it to show personality, flexibility, or enthusiasm.

Something like: “I’d love to chat more about how this topic could be shaped to serve your audience best. I’m open to collaborating on format or content to make it a perfect fit.”

Warm, human, and memorable.

Let’s rapid-fire through a few common mistakes that will instantly tank your pitch:

Here’s the truth: pitching is a numbers game. For the Creative Educator Conference alone, I get between 80–110 applications each year—and I only select 6–8 speakers. That’s not to scare you. It’s to emphasize how important it is to treat pitching as a consistent, intentional part of your business.

Don’t pitch once and give up. Pitch often. Pitch thoughtfully. Reuse and revise your core message for each new audience.

Every speaker you admire once got ignored or passed over or told “not this year.”

The ones you see on stages… they kept going.

I know pitching can feel vulnerable. It can sting to hear “no,” especially when you poured your heart into a topic, but your voice is needed. There are audiences who will be changed by your perspective, your story, your style of teaching. Don’t let rejection stop you from showing up.

Mentioned in this Episode

Creative Educator Conference

Sought-After Speaker System Course Waitlist

Episode 208: The Speaker Page Checklist Every Creative Needs to Get on More Stages

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Feeling burned out by marketing? You’re not alone. In this episode, I’m joined by the brilliant Dakota Hersey of More Than Creative to talk about a refreshing and sustainable take on content strategy by implementing a “marketing ecosystem.”

As a photographer turned marketing agency founder, Dakota shares her approach to building a cohesive system that actually works with your strengths and goals. We unpack why execution, not information is the real struggle, how to make your content work harder across platforms, and why repurposing starts before you ever hit publish.

Mentioned in this Episode

morethancreative.co

More Than Creative Podcast

instagram.com/morethancreative.co

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Feeling overwhelmed by the weight of the world and still expected to show up online? You’re not alone. In this snack-sized episode, I open up about the very real tension many of us feel as personal brand entrepreneurs when life gets heavy (globally or personally) and we’re still expected to keep the content coming.

Whether you’re a coach, speaker, educator, or creator, you’re likely no stranger to the pressure of front-facing marketing. I’m sharing a heartfelt reminder that it’s not only okay, it’s necessary to take a step back sometimes and it won’t erase all the hard work you’ve done.

The online business space often glamorizes productivity and constant output. But the truth is, building a sustainable business requires rest just as much as it requires action. Your humanity isn’t a liability—it’s your strength.

For so many coaches, speakers, educators, and creatives, our businesses depend on front-facing marketing. We’re the face, the voice, and often the whole brand. The hustle culture in the online space tells us consistency means showing up daily. But here’s the truth: showing up consistently doesn’t mean never resting.

If you’re scared that taking a break means everything will crumble, you’re not alone. I’ve felt that too. But fear of disappearing shouldn’t dictate your mental health decisions.

The idea that one missed post or a skipped newsletter will undo years of relationship-building is a myth. Your audience isn’t following you for flawless consistency—they’re here for authenticity, trust, and value. And guess what? That connection is stronger than any algorithm.

Many of us imagine that taking a break means dropping everything, going silent, and risking our reputation. But stepping back doesn’t have to be that dramatic. In fact, it can be subtle, strategic, and deeply nourishing.

Taking a break doesn’t mean disappearing. It might look like pausing Instagram stories for a few days or rescheduling that weekly email for next week. It might mean resharing old content instead of creating something fresh. None of this is lazy. It’s smart, intentional business ownership.

Unless you want to share what’s going on, you don’t have to. Some seasons call for vulnerability; others call for privacy. Do what feels right for you. And remember—most people won’t even notice you took a break.

When we talk about building a brand that lasts, we often forget that longevity is rooted in sustainability. And sustainability means you have to include margin for real life—grief, exhaustion, overwhelm, and joy.

Every time you push through when your heart is asking you to slow down, you teach yourself that your value is in your performance. But every time you pause and trust your audience will still be there, you build self-trust—and that’s where sustainability lives.

A long-lasting brand doesn’t demand you be a content machine. It supports you through every season—especially the hard ones.

Stepping back now prevents burnout later. It preserves your energy for when you’re ready to show up with clarity and purpose again. And most importantly, it keeps your business aligned with your actual life—not just your marketing calendar.

Sometimes we need a small nudge to reflect and realign. Here’s a question to sit with as you decide how to care for yourself during a heavy season.

Would it be:

Let that question sit with you. You don’t need a five-step plan. You just need the permission—which you already have.

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Want to land more speaking gigs? Start with a powerful speaker page. In this episode, I walk you through the five non-negotiable assets every creative entrepreneur should have on their speaker page. Whether you’re just starting out or refining your presence as a seasoned speaker, these tips will help you stand out and get booked.

If you’re dreaming of taking the stage—virtually or in person—your speaker page is the first thing you need to build. It’s your audition, your resume, and your first impression rolled into one.

Most creative entrepreneurs either overthink this or overlook it entirely. They get stuck waiting for the “perfect” footage, or think they need a completely separate website just for speaking. Spoiler alert: you don’t. I don’t even have one! My speaker page lives right on my main website at layleeemadi.com/speaking, and it works just fine.

Your speaker page should do one thing well: show decision-makers why they should trust you with their audience.

Let’s break down the five essentials.

This is not your business bio from your About page. This is a short, intentional statement that tells event hosts exactly what you bring to the table as a speaker.

Ask yourself:

Keep it focused, keep it punchy, and remember—this isn’t about being everything to everyone. It’s about helping someone say, “Yes, I want you at my event.”

The #1 reason people skip this step is perfectionism. I’m here to tell you: done is better than perfect.

Yes, professional footage is amazing. But in the meantime:

Hosts want to know what it’s like to learn from you. They want to hear your voice, your cadence, your passion. Even rough footage gives them more than nothing at all.

Logos of conferences, links to guest podcast spots, or even a simple bullet list of where you’ve spoken—it all helps build trust. This shows that other people have already trusted you to speak to their audiences.

Don’t have much yet? That’s okay. Start with what you’ve got. Even small workshops, masterminds, or community trainings count.

This one is gold. A glowing testimonial from an event host or audience member can do more for your credibility than a hundred polished photos.

Not sure how to get one? Reach out! Send a short, kind email to a past host or collaborator and ask for 1–3 sentences about what it was like to work with you. Bonus points if they mention your teaching style, professionalism, or audience impact.

And if you don’t have formal testimonials? Go mine your DMs, emails, or video comments for kind words you can repurpose.

This is where you show your range and depth.

List one to three topics you can confidently speak on—and then flesh them out. What makes this talk powerful? What transformation does it offer? Why are YOU the one to deliver it?

Don’t worry if others speak on the same topic. I talk about burnout, productivity, and imposter syndrome—and so do a million others. The key is framing it through your unique perspective, lived experience, and voice.

This is the section I want you to spend the most time on. Get clear. Get specific. Get excited.

If you’re reading this and thinking, “I’m not ready,” you are. The only thing holding you back is overthinking. You do not need a full brand photoshoot, a new website, or polished video content to start getting booked.

You need clarity. Confidence. And a speaker page that does its job.

You can do this in a week. I promise.

Mentioned in this Episode

Elizabeth McCravy’s Speaker Page Template

layleeemadi.com/resources

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