How Winning Edge Grew to 100 Members on Autopilot

Ben Wolfe grew up in the 90s playing the sports that every kid played: baseball, basketball, and football. He was so bad at all of them that he got cut from every single team.

That’s how he found tennis.

He didn’t know what tennis was until high school. Never took a lesson. Just picked up a racket and fell in love. Today, he’s a self‑taught 5.0 player, a 15‑year science teacher, a 20‑year high school coach, and a certified mental, fitness, health, and tennis coach. He runs the Winning Edge Community, where he helps adults and juniors improve their game off the court.

But his journey to building a thriving online community wasn’t a straight shot. It was a story of big dreams, spectacular fails, and a lesson that every creator needs to hear.

Let’s get into it.

First Set: The Grand Slam Failure (Free Community, 100% Effort, 0% Engagement)

When Ben first decided to build a community, he did what most passionate creators do: he poured his entire soul into it.

“I had a vision,” he says. “I wanted to help people remotely, give them quality content they could actually use to improve their tennis game.”

So he created a ton of courses. A ton of videos. He put everything together, made it all free, and hit “launch.”

He expected a flood of grateful players.

He got crickets.

“It didn’t quite go as well as I thought,” he admits now, laughing.

I remember talking to him back then. I warned him: “Ben, just start small. I don’t know if you’re going to get this huge audience you think you’re gonna get.”

He didn’t listen. (He’s allowed to admit that now.)

He had built everything, the courses, the structure, the content, and then threw people in. But there was no reason for them to stick around. No engagement. No community. Just a pile of free stuff that nobody asked for.

“I wasted a lot of time,” Ben says. “But I’m glad I went through it. I’m a better person and business person because of that.”

That failure taught him the first big lesson: don’t build everything before you know what people actually need.

Second Set: The Break Point (Start Small, Build as You Go)

A year later, Ben restarted. But this time, he did it differently.

Instead of building a full library first, he started with a few people. Some were friends, some were paid clients. He told them, “I’m going to build this as we go. You’re going to be my guides.”

He set a deadline: he had to have content ready for them each week. That pressure forced him to create what they actually needed, in real time.

“It helped because in real time I was like, oh, they need this, they need that,” he says. “This was helpful for me to build something that is actually high quality rather than doing it all at once and then throwing them in and realizing that was not the great experience that they needed.”

He started with one‑on‑one coaching. Then he added small group calls. He built his first paid program on GroupApp: a three‑month course with one group call per month. The content dripped week by week. He added assignments so people had to do something before moving on.

And slowly, something magical happened.

People started talking to each other in the discussion boards. They started sharing wins, asking questions, and supporting each other. The community began to feel like a community, not just a content dump.

Ben had discovered the secret: build with people, not for them.

Third Set: The Winning System (Automation, Scalability, and Your Time Back)

Once Ben had a system that worked, he did something smart: he automated the hell out of it.

In GroupApp, he set up workflows so that when someone enrolled in his first course, they automatically got:

• Weekly reminders
• Access to the next course at the right time
• A warning before their three months ended, with an easy option to renew

“I don’t have to go, ‘Okay, so‑and‑so was onboarded on January 5, now February 5 I put on a Google calendar to onboard them on the next program.’ It’s already there,” he says.

He also uses assignments to force check‑ins. Before a member can move to the next lesson, they have to complete a short reflection or action. Ben gets notified, reviews it on his phone (he did it on a plane once), and comments back.

“It’s super easy for me to do that. I can do it on my phone,” he says. “That’s the remote life, right?”

Now, Ben can scale his community to 20, 30, 50, or even 100 members without adding hours to his week. His time is protected. His members still feel supported. And the community runs itself.

“Time is always going to be everyone’s bottleneck,” he says. “You have to make sure the system allows you to scale and not take more time.”

The Playbook: How to Build a Scalable Community (So You Can Steal It)

Ben’s journey wasn’t magic. It was a repeatable process. Here’s his exact playbook:

• Step 1: Start with a few people you trust. Friends, existing clients, and anyone willing to give honest feedback. Let them in for free or at a steep discount. The only ask: they engage and tell you what they need.
• Step 2: Don’t pre‑build everything. Instead, build as you go. Let the first cohort’s needs guide your content. Set a weekly deadline, so you stay accountable.
• Step 3: Create a simple onboarding. Give them a clear “Start Here” guide. A short video, a few bullet points, and a direct link to book a call if they get stuck.
• Step 4: Structure your program into small, digestible steps. Ben went from “here’s everything” to “here are two things to focus on this week.” Less overwhelm = more action.
• Step 5: Use assignments to force accountability. Make members do something before they move to the next lesson. A reflection, a practice video, a short quiz, anything that proves they engaged.
• Step 6: Automate the journey. Set up workflows so that when someone finishes one module, they’re automatically enrolled in the next. Use drip content to release lessons on a schedule.
• Step 7: Build in natural endings. Give members a clear timeline (e.g., three months). When they’re about to finish, send an automated reminder with renewal options. If they don’t renew, automatically remove access.
• Step 8: Create spaces for connection. Separate discussion boards for different groups (adults vs. juniors). Use them to share wins, answer questions, and let members support each other.
• Step 9: Run regular live events. One group call per month keeps people connected. Record them and store them in the library for members who can’t attend.
• Step 10: Keep iterating. Ben’s community is never “done.” He’s always tweaking, testing, and improving. The system is flexible enough to evolve.

Ben’s One Big Piece of Advice

When I asked Ben what he’d tell someone launching their first community, he didn’t hesitate.

“Start with your friends. Tell them what you want to do. Let them in for free, but ask them to engage with you. When you bring other people in, they’ll know how to engage and what it looks like.”

He also stressed that community only works when people feel safe.

“You need to open up,” he says. “Share your struggles. Show them you’re human. That builds trust.”

And trust is everything. “Everyone doesn’t have trust anymore in the online world,” Ben says. “So how do you build trust? Give them value and don’t ask for anything in return.”

Finally, he warns against the money‑first mentality.

“If you go from, ‘I want to build this up to make a lot of money,’ so you charge a lot, and it’s going to be amazing, nobody’s going to sign up,” he says. “Start small. Get people in there. Your vision will become more solid. Then you’ll understand what you can charge and how to scale.”

Turn Your Skill Into a Community Today

Ben started with nothing but a vision and a willingness to fail. He bombed the first set, pivoted hard, and built a system that now runs itself. His members feel connected, they get results, and Ben gets his weekends back.

If you’re sitting on a dream to help people, stop building everything in advance. Start with a few friends, ask them what they need, and build as you go. Let them shape your vision.

When you’re ready to put it all in one place, courses, community, automation, and a way to protect your time, see what GroupApp can do for you.