Last Wednesday, I did something I’ve never done before. Instead of hosting one of my usual legal webinars or online masterclasses, I threw an online party for the Retainly reveal.

There was no traditional slide deck, no scripted sales webinar, and no basic “here’s your Zoom link” experience. Instead, we had curated invitations, giveaways, actual confetti, a custom webpage that walked everyone through the Retainly story, a live platform demo, and our lifetime founding member offer.

And we ended the night with a 30% conversion rate.

I actually had to look it up because I thought I was losing my mind. But as exciting as that number was, I don’t want to tell you only about the great parts. Almost immediately after the webinar ended, we also ran into tech issues, onboarding challenges, capacity problems, and some very real growing pains.

So here’s what happened behind the scenes—what we did differently, what worked, what absolutely did not go according to plan, and what I’m taking away from the experience.

Why I Didn’t Want to Host Another Traditional Webinar

If you’ve been around The Legal Paige® for a while, you’ve probably attended one of my legal webinars or online masterclasses. Those are usually educational classes where I teach about a very specific legal topic. We can have anywhere from around 500 to 1,500 people attend, and I typically don’t pitch anything beyond possibly mentioning a free legal guide or a small clause that could help solve the issue we’re discussing.

But the Retainly event was different. This was the finale of a seven-week sprint, and I knew we were going to reveal Retainly in a much bigger way.

My original idea was still pretty familiar: teach a legal class about sending contracts online and some of the legalities surrounding it. Then my friend Jamie challenged that plan. She basically told me to stop hiding behind the class and make the Retainly reveal a BIG deal.

Think about the people in the TLP world who would champion it. Invite the VIPs. Bring in people who would be excited about the platform and want to tell their own communities about it.

And instead of treating it like another webinar? Throw a party.

That idea felt much more like me.

We Made the Invitation Feel Like an Actual Event

One of the first things we changed was the invitation. Instead of simply sending people a Zoom link, we created a cute digital invite that felt more like something you’d receive for a birthday party—think glitter, sparkles, and Great Gatsby party vibes.

We also intentionally reached out to people who were already deeply connected to the TLP world, including people who had purchased a lot of TLP contracts, longtime members of my community, and major affiliates.

The message was simple: come to the Retainly reveal party. It’s actually going to be a party, and there will be giveaways throughout.

That tone carried into the entire event.

Why I Skipped the Traditional Webinar Slides

The next big change? I didn’t use slides.

Earlier in the year, I joined Jessie Jean’s Yap Challenge. Part of why I joined was to get better on camera, but I was also very interested in watching the marketing happening behind the scenes. One thing that stuck with me was how the presentation itself worked.

Instead of moving through a normal slide deck, she presented using a webpage that she could scroll through. I loved that because it felt like a pattern interrupt. People are used to seeing slide after slide during webinars, so a webpage immediately feels different.

So I built my own.

I Built a Webpage That Took People Through the Retainly Story

I created a custom webpage for the event using ChatGPT Codex coding and a plugin, and then designed the experience myself. There was a little green road with a gold dot that acted like a car, and that road became the visual path through the Retainly story.

We essentially drove down the road together.

I included photos, the founder story, different stages of the journey, and the pieces I wanted to discuss throughout the webinar. It took me roughly an hour and a half to two hours to build, maybe a little longer.

And one of the biggest benefits was that because I built it myself, I knew the presentation inside and out. I didn’t need a script. The webpage itself guided me through the story, which made me feel incredibly comfortable during the event.

We Started With Reflection Before Getting Into Retainly

The beginning of the event felt a little like a mini mastermind or group coaching session. I asked people to think about their big wins from 2026 so far.

One practice I’ve learned through masterminds and group coaching experiences is to intentionally spend a few minutes writing down everything you’ve already accomplished. That can help you see how much you’ve actually done instead of moving into Q4 completely focused on everything you still think you need to accomplish.

From there, we talked about doing one thing, why you’re running your business in the first place, who you’re doing it for, and the reality that failures and difficult seasons happen. Then I shared more of my own founder story.

The Founder Story Behind Retainly

I walked everyone back about two years to when I first started having the idea for what I wanted Retainly to become. The goal was connected directly to the business owners already buying contracts from The Legal Paige®.

I wanted them to have a place where they could house those contracts and easily send them to their own clients.

During the webinar, I explained why I built Retainly, who I built it for, and how the idea developed. Then we moved into the actual platform.

I Did My First Live Retainly Demo

During the event, I gave a live demo of Retainly and showed people some of my favorite features along with features that were coming soon.

The webinar replay shows things like:

• The contract editor

• Lead forms

• Questionnaires

• Clients and third parties

• Shareable links

• The refer-and-earn program

• How the platform brings client and project information together

I also explained the philosophy behind Retainly. It’s intentionally simple.

I don’t want to build something stuffed with every bell and whistle imaginable. I want it to handle the legal, client, and lead necessities really, really well.

And I wanted the platform to be user-led and community-backed. Retainly wasn’t built only from what was inside my own brain. Beta testers and founding members have been giving us feedback and helping us shape the platform along the way.

Then We Introduced the Lifetime Founding Member Offer

During the webinar, I pitched the Retainly founding member lifetime rate. Instead of paying monthly or annually for the platform, founding members can pay one lifetime price.

We’re capping that offer at 500 founding members.

By the time I recorded the podcast episode, more than 100 of those spots had already been taken in roughly a week, including beta testers who had previously joined at the founding member rate.

And on the night of the webinar itself, we hit the number I still can’t stop talking about: 30% conversion.

People were still joining afterward, too. But that sudden growth also created the first major problem.

Launch Hiccup #1: Our Development Team Wasn’t Online

Before this event, people had been trickling into Retainly, which meant we had been able to handle customer service issues in a reasonable amount of time.

This was not a trickle.

After the webinar, we discovered an issue where some people’s Stripe payments weren’t syncing correctly with the plan shown on the Retainly backend. That meant someone could pay for a lifetime membership, log into the platform, and see that their account said “trial.”

I was devastated. These people had just made a big investment, and the platform was showing them something completely different.

Our development team is overseas, and it was nighttime for them during the webinar. The event had been on the calendar for a long time, but they weren’t online when the issue happened. And this was something only the development team could fix.

We let customers know what was happening and told them we were working on the issue. It ended up being resolved in less than 12 hours.

But the lesson was very clear: for a big launch, have all the people you may need available—including your development team when you’re launching a tech platform.

Launch Hiccup #2: White-Glove Onboarding Was Bigger Than Expected

The next unexpected challenge came from onboarding.

We had been offering white-glove onboarding for some new members, helping them move over things like:

• Current projects

• Current clients

• Lead forms

• Contract templates

• Invoice templates

• Proposal templates

What I did NOT anticipate was how many people would want to bring over all of their archived projects, too. For some people, that meant hundreds or even thousands of previous clients.

We hadn’t built the onboarding process around moving everything over on day one because I don’t think you necessarily need your entire client history inside the new platform immediately. But it became something we needed to troubleshoot.

We spent about a week working through that issue and making decisions as a company about how to handle it. Ultimately, it was one more reminder that this is what happens when you’re building a startup.

There’s turbulence.

Our Team Hit Max Capacity

The biggest takeaway wasn’t actually about webinar strategy. It was about capacity.

Between Create and Cultivate, our seven-week sprint, launching Retainly 2.0 with a new business-owner interface, preparing the webinar, handling the launch, and addressing the issues afterward, my team went essentially nonstop for three days. We weren’t sleeping enough.

And I realized very quickly: I don’t want this to be the way we operate.

That wasn’t the plan, it wasn’t healthy, and it wasn’t okay. So now we’re reevaluating. Maybe I don’t bootstrap quite as aggressively. Maybe we bring in angel investors or other capital so we can hire additional support.

We’re looking at areas where we may need help, including a fractional chief marketing officer, additional customer service support, and potentially more help on the product side.

Because there comes a point when a team simply cannot keep doing everything.

The Webinar Was a Huge Win and the Aftermath Taught Me Just as Much

I’m incredibly proud of my team. The webinar itself went better than I could have imagined. The party concept worked. People connected with Retainly. We had fun. We threw real confetti. We gave away Venmos, contract templates, and Retainly-related prizes.

But the next few days also made the weaknesses in our systems and capacity impossible to ignore. Both parts matter.

That’s what I wanted to share with this episode—not only the 30% conversion rate, not only the fun screenshots and confetti, but the startup growing pains happening behind the scenes, too.

Want to See the Retainly Webinar for Yourself?

The webinar replay walks through the story behind Retainly and includes my first live demo of the platform.

You can see the contract editor, lead forms, questionnaires, clients and third parties, shareable links, the refer-and-earn program, and more. You’ll also hear more about why I built the platform and the goal of making it a user-led, community-backed tool built by service providers for service providers.

If you’re interested in becoming a lifetime founding member, there are only 500 founding member spots available.

And if Retainly isn’t for you because you already have a platform you love, consider sending the replay or this episode to another business owner in your world who might be looking for a simpler way to manage clients, projects, proposals, contracts, and invoices.

Retainly Webinar Replay: https://getretainly.com/reveal-replay 

Lifetime Founding Membership: https://getretainly.com/foundingmember