I just got back from Create & Cultivate in Los Angeles, and I have A LOT to debrief.

If you followed along on social media, you probably saw Team Retainly at our booth in the Small Business Marketplace. You also may have seen some of the conversation happening online after the first day of the festival.

So… was Create & Cultivate worth it? Would I sponsor it again? What actually worked at our booth—and what would I completely change next time?

After experiencing the festival as both a sponsor and, on Sunday, an attendee, I walked away with plenty of thoughts about sponsorship ROI, booth strategy, swag, logistics, attendee experience. And because I cannot turn off my lawyer brain...the contracts and legal issues business owners should be thinking about when they participate in or host events.

Here’s my full Create & Cultivate 2026 recap.

Why I Chose to Sponsor Create & Cultivate

I don't say yes to every sponsorship opportunity that comes my way. For this one, I was really intentional.

I had followed Create & Cultivate for a long time and had watched other brands and people in my industry attend. Before committing, I talked with people who had participated in previous events and asked about their experiences. I wanted to understand whether the opportunity actually made sense from a business perspective rather than saying yes because it sounded exciting.

At the same time, I was personally ready to get back into in-person events.

I typically have a spring and fall travel season where I keynote, sponsor, teach breakout sessions, network, and spend time meeting people face-to-face. But I hadn't traveled for work since around spring 2025.

A lot happened during that time. My team was preparing for two important team members to go on maternity leave, we were heading into the fall and Black Friday season at The Legal Paige®, and I was DEEP in building Retainly.

Retainly officially launched on December 23, 2025, and by September 2026, I was ready to start introducing it to a larger audience in person.

Create & Cultivate's focus on women entrepreneurs, founders, investing, tech companies, product businesses, personal brands, and building brands felt aligned with where I was headed. Then I found the Small Business Marketplace.

The $5,000 Small Business Marketplace Sponsorship

Traditional large-scale activations at a festival like Create & Cultivate can be expensive, and those simply weren't in our budget.

Retainly is still a new software company, and spending tens of thousands of dollars on one activation wasn't something I could justify. The Small Business Marketplace was different. It was available to businesses doing under $1 million in revenue, and our booth cost $5,000.

That's still a LOT of money for a small business.

Retainly and The Legal Paige® ultimately split the expense. Our booth was officially a Retainly booth but realistically, the businesses overlap. Many people already knew me through The Legal Paige®, while other people needed Retainly, the law firm, or some combination of those resources.

Our biggest goal, though, was clear: put Retainly in front of new people and introduce the brand in person.

Planning a Booth When You Sell Digital Products and Software

Here's where things got interesting.

We were given a four-by-two-foot booth.

FOUR BY TWO.

When you sell jewelry or another physical product, you can put the product right on your table and let people interact with it. We sell digital contract templates and a digital contracting, invoicing, and CRM platform.

Not exactly something you stack beautifully on a table.

We also weren't allowed to bring a backdrop or cover the booth with our own signage. Create & Cultivate had its own visual aesthetic and branding for the Small Business Marketplace, so we had to get creative with the space we were given.

The question became: What actually makes someone want to walk up to a booth?

I had already spent years paying attention to booths and activations at events. I talked with people who had experience in corporate events, influencer activations, and large conferences.

And Team Retainly decided to go all in on what I lovingly called…

Sick swag.

Our Event Swag Strategy

I did NOT want to hand out stuff people would throw into their hotel trash can before they even flew home.

I wanted useful things. Things people actually wanted to take. Things they might continue using after the event.

Some of our biggest hits included:

• High-quality velvet scrunchies

• Regular hair ties

• Hand sanitizer

• Legally Legit® mini legal pads

• Retainly gel stylus pens

• Legally Legit® campfire mugs

• Stickers

• Small lens and phone camera cleaners

A lot of the swag wasn't covered in logos. Instead, we incorporated Retainly's dark green and gold brand colors so the pieces still felt connected to the brand without looking like traditional promotional products.

And then there were the giveaway bags.

The $1,000+ Giveaway Bags That Brought People Back to Our Booth

We put together six larger giveaway bags and gave them away throughout Saturday. They were Lands' End bags filled with things like comfort sweatshirts, Loop earbuds, leather padfolios, Legally Legit® mugs, hand sanitizer, scrunchies and hair ties, a free year of Retainly, white-glove Retainly onboarding, and a contract from The Legal Paige®.

People entered using a QR code, and we announced winners throughout the day.

The reactions were SO fun. People screamed when they won, and that energy helped attract even more people because everyone nearby wanted to know what was happening and how they could enter.

It worked. But, naturally, I now know about ten things I'd change next time.

Lesson #1: Bring More Swag Than You Think You Need

Then bring more.

We ran out.

We talked with roughly 400 to 600 people, if not more, and our table stayed busy throughout the day. I wish we had shipped more products in rather than trying to fly with everything inside two 70-pound suitcases.

Next time, I'm shipping the heavy stuff and bringing MORE.

Lesson #2: Plan Swag Around the Season and Setting

We knew Los Angeles would be warm. We did not fully anticipate how hot it would feel spending an entire day outside around so much concrete.

My biggest missed opportunity? Paper fans.

Imagine a branded paper fan with Legally Legit® on it being carried around the festival by attendees who desperately needed something to cool themselves down. People would actually use it, and every person carrying one would also be increasing brand visibility.

Next time, I am thinking much harder about what people physically need in the environment I'm walking into.

Lesson #3: Always Bring Bags

I don't care how many times an event tells me there will be bags.

I'm bringing bags.

People at Create & Cultivate were collecting swag from activation after activation—and they needed somewhere to put it. We had six large Lands' End bags for our giveaway, and people repeatedly asked if they could have one.

They wanted the actual giveaway, yes. But they also just needed A BAG.

Next time, I'm bringing hundreds. Canvas bags, foldable reusable bags, something easy to carry around.

Because imagine thousands of people walking through an event while others ask them, “Where did you get that bag?” That conversation can lead straight back to your booth.

Lesson #4: Have Handouts for Every Type of Person You Serve

This became especially obvious for our businesses.

Someone would walk up and need Retainly. The next person needed The Legal Paige®. Someone else had questions that connected more closely with Griffith Law.

We needed:

• A Retainly handout

• A Legal Paige® handout

• A Griffith Law Firm handout

• Something explaining all three together

• Clear information about where to connect with us online

Not every lead needs the same information.

Next time, I'm treating those handouts almost like a little brochure station so people can grab exactly what applies to them.

Lesson #5: Make Your Social Handles Impossible to Miss

So many people asked, “Where can I follow you?”

That shouldn't have required a conversation.

I want our social media handles sitting front and center at future booths. For us, that means making accounts like @thelegalpaige and @getretainly incredibly easy to spot.

Because the in-person conversation is only the beginning. You also need to give people a simple way to continue interacting with the brand after they leave the event.

Lesson #6: Think More Strategically About Swag and Social Engagement

This is one of the things I'm most disappointed we didn't do.

We were hyper-focused on collecting emails through our big giveaway, and that part worked. But I wish we had created different levels of swag tied to different interactions.

Maybe basic swag is simply available. Maybe someone who wants the higher-value scrunchie, mug, or notepad follows the brand. Maybe an even higher-value item is connected with taking a selfie at the booth, posting a story, or tagging us.

For Retainly especially, this could have created a much bigger social connection with people who had already met us in person.

Lesson learned.

QR Codes Aren't Always the Answer

Another thing I'd change? I might go more old-school next time.

Everyone was using QR codes, and we used one for our giveaway too. But internet and cell service were extremely unreliable on Saturday.

We had a physical sign-up method as a backup, and in hindsight, I kind of wish we had leaned into it.

There's something personal about physically writing down your name and information. It also could have made it easier for me to jot down a quick note about someone I'd just spoken with.

There are people I can still picture from the festival, but I don't remember their names. After hundreds of conversations, that's inevitable.

Having a simple system for handwritten notes could have made post-event follow-up much more personal.

The Great Booth Location Saga

Before the festival, the map made the Small Business Marketplace look more front and center than where we ultimately ended up.

Christine and I arrived Friday night and were among the first people there to set up. We picked a booth location on the edge because we thought it would give us more visibility.

By Saturday morning, our booth had been moved farther into the corner. You really had to intentionally walk into that area to find us.

That was frustrating.

But I'm also a silver-lining person, and there WAS a silver lining. Being close to the edge gave us:

• More shade

• A little bit of airflow

• Some protection from the intense sun

And on Saturday, that turned out to matter. A lot.

The Heat, Check-In, Food, Bathrooms, and Other Saturday Problems

This is where I want to be careful.

I was a sponsor on Saturday. I was not experiencing the festival in exactly the same way a general attendee did.

But we experienced or observed some of the same operational problems.

Check-in was difficult. Badges weren't printing smoothly, and the app was difficult to load because cell service and internet were poor. People needed the QR code in the app to get their badges, which made the connectivity issues even more frustrating.

VIP attendees were supposed to get in ahead of general admission, but lines backed up and people ended up waiting outside in the heat.

Once attendees were inside, I also heard and saw concerns around food, bathrooms, seating, shade, and long lines.

For us, food was one of the biggest problems. We had asked in advance whether we should bring food and snacks and had been told there would be plenty.

That was not our experience.

We found lots of drinks and water, thankfully, but very little food. By the end of Saturday, Team Retainly was exhausted. We had been standing, talking, working the booth, drinking water, and barely eating all day.

Sunday Was a Completely Different Experience for Me

Our Small Business Marketplace sponsorship only covered Saturday, and we chose not to pay extra for Sunday.

So Christine and I got to come back on day two purely as attendees. And for me? Sunday was SO much better.

It wasn't as hot. There weren't as many people. And I could actually sit down and experience the content.

I enjoyed speakers and conversations around content creation, money, venture capital versus angel investment, and funding a bootstrapped business. Those topics felt especially relevant to where I currently am with Retainly.

My biggest content criticism was actually that I wanted MORE. Some keynotes were only around 20 or 30 minutes. Panels sometimes had four or five impressive people sharing one short window of time.

I would have loved to see keynotes run closer to 45 minutes or an hour and have more time for deeper panel conversations.

And then Sunday night? Christine and I got to attend a private Cardi B concert. That was a pretty incredible way to end the festival.

So… Would I Sponsor Create & Cultivate Again?

Yes. I would.

There has been a lot of negative conversation about the event, and I think people are allowed to talk honestly about their experiences. There were real problems on Saturday, and I am also genuinely hopeful the organizers address them.

From our perspective as a sponsor, though, the event was still successful.

Our booth had traffic. We generated hundreds of strong leads. We met businesses and people completely outside our usual circle.

We also had conversations about:

• Potential partnerships

• Membership opportunities

• Guest expert opportunities

• Podcasts

• People who could help introduce Retainly to new audiences

There is nothing like face-to-face networking.

Online visibility matters, but it doesn't completely replace meeting someone in person, having a real conversation, and letting them meet the people behind a business.

For Retainly and The Legal Paige®, that part was a major win.

My Biggest Hope for the Small Business Marketplace

I REALLY hope Create & Cultivate continues the Small Business Marketplace.

And I hope they continue improving it.

If the festival is focused on founders and growing businesses, there is an incredible opportunity to give businesses under $1 million in revenue meaningful visibility.

I'd love to see more communication with those small businesses before the festival, including things like:

• How much swag to bring

• What to expect from the weather and physical environment

• Exactly where the booths will be

• How much foot traffic organizers expect

• What attendees may need throughout the day

• What logistics small businesses should prepare for

The bigger activation sponsors may have extensive event experience. A newer business participating in the Small Business Marketplace might not.

More communication could make a massive difference.

My Lawyer Brain Couldn't Ignore the Contract Questions

You knew this part was coming.

This is the Legally Legit® Podcast after all.

A quick clarification before we get into it: I'm not saying anyone did anything illegal here, and this isn't legal advice about this specific event.

I'm simply explaining how my lawyer brain processes situations like this.

If You're a Sponsor or Vendor, What Does Your Contract Actually Say?

A map can show you where a booth appears to be located. But your sponsorship agreement is where you need to look for what you're actually being promised.

Does your agreement promise:

• A specific booth location?

• Specific visibility?

• TVs or equipment?

• Shade?

• Signage?

• Other deliverables?

And what happens if the organizer doesn't provide those things?

Do you receive a refund? A credit? Something toward next year's event? Nothing?

If something matters to you, get it in writing.

I think sponsorship agreements and vendor agreements need to be incredibly descriptive. And after this experience, I'll be going back through mine too.

What About VIP Ticket Buyers?

VIP attendees paid for a particular kind of experience.

The important question becomes what was actually marketed and what was delivered. Early entry, better access, food, seating, bathrooms, or whatever else is specifically advertised can become relevant when an attendee feels the purchased experience did not match what they received.

Event terms may also contain provisions like:

• No-refund policies

• Subject-to-change language

• Limitations of liability

Those can matter.

But, as I explained on the podcast, they aren't necessarily a magic shield when there is a significant gap between what someone believes was promised and what they experienced.

Event Safety Still Requires Actual Planning

Contracts and waivers do not replace planning for people.

When thousands of people are gathered in one location, things like heat, shade, water, bathrooms, food, and seating matter.

You may have assumption-of-risk or waiver language in your event terms. But paperwork doesn't replace taking reasonable steps to plan for the people attending.

The Bigger Legal Lesson for Your Own Business

Whether you're planning an event, photographing one, coaching, hosting a retreat, teaching a workshop, or delivering another service, the big takeaway is simple:

Make sure your marketing matches your contracts.

And make sure both match what you actually plan to deliver.

If your Instagram, website, or sales page promises something, your client may be able to point back to that marketing outside of the agreement they signed.

So be thoughtful about what you promise. Make your contract clear about what is included. Spell out what could change, and address what happens if it does.

Things WILL go sideways sometimes—especially with events.

The goal isn't to pretend nothing can ever change. It's to make sure your marketing, your contract, and your real-life delivery are aligned as much as possible.

What's Next for Retainly + The Legal Paige®

Create & Cultivate officially kicked off my fall travel season.

Next, I'm headed to the Wild Women Summit in Montana, where we're sponsoring and I'll also be attending.

After that, I'm going to the first OGC Summit in Denver. I'm especially excited about that one because Old Girls Club has been an online tech community for me so far, and this will be my first opportunity to meet many of those people face-to-face.

We're also heading to the Showit Spark Conference, where we're sponsoring and I may be doing a short keynote.

I'm excited to keep expanding my networking bubble. The wedding, event, photography, and coaching industries will always have a huge place in my heart. But I'm equally excited to keep introducing Retainly to people in new business spaces.

My Final Takeaway From Create & Cultivate

Things did not go perfectly. There are plenty of changes I'd make to our own booth, and there are things I hope the festival changes too.

But Team Retainly and Team TLP showed up, adapted, talked with hundreds of people, generated leads, built relationships, and made the most of the opportunity.

And I'm proud of that. For us, the sponsorship was a win.

More importantly, I walked away with lessons I can take into every future sponsorship, conference booth, and live event we participate in.

If you're planning to sponsor an event yourself, remember:

• Bring more swag.

• Bring bags.

• Make it easy for people to follow you.

• Give different people the information they actually need.

• Think about what will be useful in the specific environment you're entering.

• And before you sign the sponsorship agreement, read exactly what you're being promised.

You can DM me on Instagram at @thelegalpaige with questions about event sponsorships, booth planning, or legal topics that came up while listening.

And if you haven't checked out Retainly yet, you can follow @getretainly to learn more about the contract, invoicing, and CRM platform we built for small business owners.