What It Actually Feels Like to Be at Founders Weekend: A Weekend Through Lisa Simone Richards' Eyes

There are events you attend, and there are events that change things.

Lisa Simone Richards has been to both. The Canadian founder behind Pearl Spark Pages, a journaling brand built specifically for female founders, attended her first Entreprenista Founders Weekend in 2024. After experiencing the magic in 2024, she didn’t hesitate to come back in 2026. "It really is the weekend of the year for me," she said. "The amount of fulfillment that I felt leaving there, the amount of inspiration…it was just a good all-around 360."

Here's what attending Founders Weekend actually looks like, from the inside.

Before the Doors Open

Lisa is the kind of founder who reverse-engineers outcomes. Before she books a ticket to anything, she thinks about what a win looks like on the other side of it. Founders Weekend, she says, is one of the few events where she consistently walks away having gotten more than she planned for.

But the real win of attending is about so much more than information and sessions. "One of the things I really enjoyed was not only the speakers on stage, but those really small moments, like being in the hallway, catching a quick word with them, a conversation at breakfast," she said. "So I knew when I came to the 2026 event, I was really looking forward to those tiny moments."

What a Day Looks Like

Founders Weekend 2026 featured three full days at The PGA National Resort in Palm Beach Gardens, Florida. There were morning activities, mainstage sessions, breakouts, evening dinners, and activations scattered throughout.

Lisa opted to start her mornings with breakfast, excited by the unexpected opportunities these relaxed moments created. "Going up to a random table at breakfast, not knowing who you're going to sit with, but just being open to whatever happened; those are the moments that things really click," she said

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She appreciated that the 2026 event introduced assigned seating, which she said took the guesswork out of where to land when you first walk in. Between sessions, she moved through vendor activations, sponsor booths she described as genuinely useful rather than just paid placements, and unexpected interactions with other attendees. Those quick hallway exchanges would often turn into something more.

"At one moment, Jess Gleim and I found each other,” she recounted. “We got glasses of wine, ordered some appetizers, sat and talked about our families for 15 minutes. The kind of stuff that doesn't come up in passing."

Evenings were loosely structured. Dinners were coordinated two of the three nights, and Lisa attended them both. The third night was an opportunity to organically connect with other attendees. “Let's just see what happens and not be so obsessed with the perfect schedule," she said. "Those chance encounters were a highlight as well."

The Room No One Tells You About

Ask someone who's never been to Founders Weekend, and they'll describe it as a conference. Ask someone who has, and they describe something harder to name.

Lisa tried to articulate the atmosphere when asked directly, and instead she landed on a story about her interaction with Suzanne Appel, founder of Young CEO Squad, a company that helps encourage entrepreneurship among students. In a previous panel, Lisa watched as Suzanne stood before the crowd and asked, “What are you looking for? What help do you need? Let's see who in the room can help you.” Immediately, half a dozen women stood up with the connections needed to get Suzanne’s program into more schools.

The camaraderie and immediate support made Lisa tear up almost immediately. She knew she had found something special. "I didn't even cry at my own wedding!” she laughed. “So this event made me more emotional than the most important day of my life."

And Suzanne's story wasn't a one-off. "Seeing things like that happen over and over again, it's just the nicest room to be a part of and know that everyone genuinely wants to see you win and it's going to help you succeed," Lisa said.

This thread running through Founders Weekend is difficult to market and easy to underestimate. The Entreprenista community is built on the premise that the most valuable thing you can give another founder is your honest attention and your real connections. In a room of several hundred women, that premise plays out at scale.

The Conversations That Actually Move the Needle

At Founders Weekend, it’s fair to say that one breakfast can change the direction of an entire business.

For Lisa, that’s exactly what happened at this year’s event. She had been weighing whether to pursue angel investment for Pearl Spark Pages when she sat down next to Tisha Thompson, founder of LYS Beauty. "I'm sitting at breakfast with this woman whose products are in all the Sephoras, and you pay thousands of dollars to get coaching with her," Lisa said, "and I'm just talking to her over eggs."

Tisha's advice was blunt: an investment looks shiny, it sounds good, but don't do it if you don't have to. The impact was real and strongly impacted how Lisa plans to fund her company in the future. "That's a meaningful small moment that probably will have a big impact on my exit one day," Lisa said.

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Another major impact the event had on her business? Moving her bottom line. Lisa brought her primary product to the event, journals specifically designed to help female founders reflect as they build. Every single one sold. "I'm about to have my best sales month ever," she said.

What Stays With You

Two years after attending her first Founders Weekend, Lisa has a growing list of relationships that began in that room. Jessica Zweig, whose book Lisa had read years before they ever met, had a real conversation with her at Founders Weekend in 2024. In 2026, they crossed paths again in a hallway.

"I know this woman meets a billion people," Lisa said. "But then I saw her at the event and she was like, ‘I remember you were here in 2024. Of course, I remember. We talked about this…’"

The experience of feeling seen by someone you've looked up to for years is, Lisa admitted, hard to describe. "I don’t know if it's validating, if it's affirming, but it certainly feels good."

Anne Mahlum's closing keynote also stayed with her. Lisa describes herself as a control freak, the kind of founder who finds it difficult to delegate even to people she trusts. Mahlum's framework for building a team that runs without you landed differently in person than it would have as a podcast clip or a blog post.

"One of the things that Anne talked about is that I wouldn't be able to sell my business for as much as possible if I needed to be a part of it. I had to make myself redundant," Lisa recalled. "So it's very impactful for me to remember…give better instruction, lead better, sit back and give people an opportunity."

On the Investment

Lisa is based in Canada, and the exchange rate works against her. The hotel, the ticket, the flights, the meals out; the trip was a significant expense for her to make.

She went anyway.

"I knew that I would walk out of that room feeling like I can do this," she said. "And I needed that. My business genuinely needed that."

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Because attending Founders Weekend is about so much more than static business development. It’s a step toward meaningful growth, built-in mentorship, and connections you never see coming and can’t plan. "My business would be nowhere where it is today without this community,” Lisa said. “It's such a missed opportunity to not be a part of something like this. It doesn't matter what it costs. It doesn't matter where you need to dig and sacrifice. Do it for the end result. I promise it's worth it."

Ready to Be in the Room?

Founders Weekend 2027 is on the horizon. The 2026 event sold out, and the 2027 retreat is expected to do the same.

Founders Weekend is open exclusively to Entreprenista members. Join the community today and be among the first to know when tickets go live.