The Community Whisperer: How Jenna Ostrye Built Success on Skool

🎙️ Based on a podcast between William Renner and Jenna Ostrye

🔥 Join Jenna's Masterminds community HERE

In the rapidly evolving landscape of online community building, Jenna Ostrye stands out as a quiet powerhouse in the digital education space. Ranked #5 on Skool's all-time leaderboard, Ostrye has carved a unique niche for herself within the community-building platform created by Sam Ovens and popularized by Alex Hormozi. Her successful communities, "Admins" and "Admins Mastermind," help people monetize their presence on Skool in 90 days or less—all while maintaining a faceless presence online that proves you don't need to show your face to make money online.

I recently sat down with Ostrye to discuss the culture of Skool, effective online community building strategies for beginners, and what it takes to create a thriving digital education community that consistently generates income in today's competitive online landscape.

𝐅𝐢𝐧𝐝𝐢𝐧𝐠 𝐘𝐨𝐮𝐫 𝐅𝐢𝐭 𝐖𝐢𝐭𝐡𝐢𝐧 𝐭𝐡𝐞 𝐏𝐥𝐚𝐭𝐟𝐨𝐫𝐦

When asked about her journey making money online through Skool, Ostrye is refreshingly candid. "Most people talk about the beginnings of them being on Skool, and they'll say 'I'm all in,' but there's a shift right around the three-month mark," she explains. "It's where you thought you'd have success with what you were going to do, and then you get into Skool and start really connecting with the community-building culture that makes this platform unique for online education."

This pivot point is crucial for new online community builders looking to generate income through digital education. Ostrye notes that many newcomers approach Skool with a mindset better suited for traditional social media—"talking to people rather than talking with people." This fundamental misunderstanding of the platform's community-centric design leads many to struggle with monetizing their knowledge and expertise.

"If a community was on Facebook, you can talk to people as if it's a social media platform—not super community-based. It will still work, but it's not going to be the best. On Skool, that's not going to work for you if you want to make money online through community building," Ostrye points out.

What makes Skool different from other online education platforms, according to Ostrye, is that community isn't just a marketing buzzword—it's built into the technology itself, creating opportunities for authentic engagement that traditional course-based platforms simply can't match.

𝐓𝐡𝐞 𝐓𝐡𝐫𝐞𝐞-𝐌𝐨𝐧𝐭𝐡 𝐑𝐮𝐥𝐞

For those serious about building profitable online communities on Skool, Ostrye recommends giving it a solid three-month commitment. "You've got to be consistently persistent, and you need to be the one showing up in your digital education space," she emphasizes. "It's not on your people in the beginning—that's key to eventually making money online through community building."

This commitment period is where many community builders falter. "Those people just gave up. They went hardcore for maybe the first couple of days, waiting for other people to come and engage. But why would someone join your community if you're not going to be engaged in it yourself?"

She recounts how someone once reviewed her Skool community, saying it "would not survive without her"—but Ostrye sees this differently. "While I want to be a good portion of the community, I shouldn't be the heart of the community. A good thriving online education community should not be dependent on me alone. That's not sustainable for making money online long-term."

𝐌𝐨𝐧𝐞𝐭𝐢𝐳𝐚𝐭𝐢𝐨𝐧: 𝐌𝐚𝐤𝐢𝐧𝐠 𝐭𝐡𝐞 𝐏𝐥𝐚𝐭𝐟𝐨𝐫𝐦 𝐖𝐨𝐫𝐤 𝐟𝐨𝐫 𝐘𝐨𝐮

One of Ostrye's core missions is helping community owners monetize effectively through Skool's unique online education ecosystem. "I don't want anybody to join my community and not make money online within the first couple of months," she states firmly, highlighting her commitment to practical, results-oriented community building strategies.

She observes that many people approach Skool as a funnel replacement rather than a true community-based online education platform. "You don't need a website to use Skool to make money online. You don't need to have a newsletter. You don't need to do emails—you can, but the platform is designed to streamline the entire community building and monetization process."

This perspective shift is critical. Instead of seeing Skool as just another marketing channel, successful community builders understand its unique value proposition: creating spaces where people genuinely want to engage and, as a result, are willing to pay for access to deeper connections and knowledge.

Balancing Vision and Co-Creation

When building an online education community, there's often tension between the founder's vision and allowing members to shape the direction of the learning journey. Ostrye has a nuanced take on this balance that directly impacts monetization success on Skool.

She disagrees with the approach of "starting a community on Skool and letting it be mostly whatever the community needed," particularly for newcomers trying to make money online. This approach might work for established online education creators who "already have plenty of knowledge and have proven that they have plenty of knowledge," but it can be disastrous for those without an existing audience or clear community building strategy.

"To have somebody come into your online education community and say 'I'm going to create this with you,' and they're like 'Create what?'—it's confusing," Ostrye explains. "I thought you were going to be teaching something specific that helps me make money online through community building."

Rather than inviting just any three friends to start your Skool community—a common piece of advice on the platform—Ostrye recommends inviting only your most supportive friends who understand your online education goals and what you're trying to build. Even then, you need to give them a reason to show up consistently, which builds the engagement foundation needed for monetization.

Starting Your Journey to Making Money Online Through Skool

For those just getting started with community building on Skool, Ostrye suggests treating the initial period as an educational experience rather than rushing to monetize.

"Use the 14-day trial to cram information like you're studying for a test," she advises. "Really try to understand what they are trying to teach about online education and community building, network with successful creators, and decide who you want to be your mentor for making money online."

Instead of clinging to the idea of building the perfect online education community on the first try, Ostrye encourages newcomers to be flexible and willing to start over when learning the Skool platform. "There's too many people that continue to pay the $99 because they think 'I'm going to make that one community work,'" she notes. "Just go ahead and cancel it, learn more about effective community building strategies, and be okay to be wrong before committing to a monetization path."

𝐍𝐞𝐭𝐰𝐨𝐫𝐤𝐢𝐧𝐠 𝐟𝐨𝐫 𝐒𝐮𝐜𝐜𝐞𝐬𝐬 𝐨𝐧 𝐒𝐤𝐨𝐨𝐥

As a master networker on Skool, Ostrye's approach to community building centers on genuine engagement rather than strategic positioning. "Being ultra-observant allows you to pick up on the subtle things that most people miss in online education spaces," she explains. "There is so much power in moments where people have missed out on being able to show up and make sure others feel seen, heard, and remembered—this authentic connection is what ultimately helps you make money online through community building."

She criticizes inauthentic engagement tactics in online education communities, like using automation to be the first commenter on posts. "To successfully network on Skool and build genuine relationships that lead to monetization opportunities, you need to read with purpose—to understand—and then be able to clearly communicate your thoughts and feelings about community building topics."

Ostrye likens Skool to high school social dynamics, where there are popular figures and different social circles within the online education ecosystem. But unlike stereotypical high school hierarchies, "the popular kids on Skool are very happy, welcoming, and focused on helping others succeed with their community building efforts and making money online."

However, she cautions against following someone just because they're popular in the Skool ecosystem. "I would much rather be associated with people whose mission is to make meaningful impact through their online education communities," she says. When choosing community building mentors, she advises looking beyond personality to results: "Are they actually helping their community members make money online? I don't know that that's going to happen for you unless you're willing to really observe their actions and do the same things they do with your own Skool community."

𝐇𝐨𝐰 𝐭𝐨 𝐂𝐡𝐨𝐨𝐬𝐞 𝐭𝐡𝐞 𝐑𝐢𝐠𝐡𝐭 𝐒𝐤𝐨𝐨𝐥 𝐂𝐨𝐦𝐦𝐮𝐧𝐢𝐭𝐢𝐞𝐬

For newcomers unsure which online education communities to join on Skool, Ostrye offers practical advice for aspiring community builders: "Go see how they show up in their free community and whether they're actually teaching effective strategies for making money online."

She suggests evaluating potential community building mentors by their free offerings on Skool: "If you can't get a win from their free community, how likely are you going to get a win from their paid online education community when it's probably somewhat similar? Look for mentors who deliver genuine value about making money online even in their free spaces."

Ostrye also recommends looking at the success stories a community shares. "What are the success stories that they have? Sometimes the success story you can take with a grain of salt," she cautions. "Is this something that I could actually duplicate? If not, then don't do it."

𝐓𝐡𝐞 𝐅𝐮𝐭𝐮𝐫𝐞 𝐨𝐟 𝐌𝐚𝐤𝐢𝐧𝐠 𝐌𝐨𝐧𝐞𝐲 𝐎𝐧𝐥𝐢𝐧𝐞 𝐰𝐢𝐭𝐡 𝐒𝐤𝐨𝐨𝐥

Looking ahead, Ostrye is excited about upcoming Skool platform developments, particularly the affiliate program that will enhance community building opportunities. "People are going to be able to be rewarded when it comes to referring the online education communities that they love," she explains. "That's going to make monetization so much easier for those committed to authentic community building principles."

She believes this feature will encourage more sustainable, retention-focused online education communities on Skool. "The ones that are going to succeed and actually be leaders and affiliates in the community building space are those recommending communities that make a difference, that provide on the promise of helping members make money online through authentic engagement and valuable knowledge sharing."

𝐅𝐢𝐧𝐚𝐥 𝐓𝐡𝐨𝐮𝐠𝐡𝐭𝐬

Throughout our conversation about effective community building strategies, Jenna Ostrye repeatedly returns to themes of authenticity, meaningful engagement, and patient persistence on Skool. In a digital education landscape often dominated by quick-fix solutions and flashy personalities, her approach to making money online offers a refreshing alternative focused on sustainable community development.

"If anybody's wanting to know how to build a better online education community on Skool, whether you're an owner or in a supportive role looking to make money online through community building, I would love to have you in Admins," she concludes. "I'm okay growing slow because I want the right people to be in there who are truly committed to creating value-driven communities."

As Skool continues to evolve as a leading platform for online education and community-building, Ostrye's insights serve as a valuable roadmap for those looking to create digital spaces where authentic connection translates into sustainable success and reliable income generation.

🔥 Join Jenna's Masterminds community HERE

or 𝗪𝗮𝘁𝗰𝗵 𝘁𝗵𝗲 𝗶𝗻𝘁𝗲𝗿𝘃𝗶𝗲𝘄 𝗵𝗲𝗿𝗲 👇

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