Building Digital Belonging and Strong Online Communities with Todd Nilson
The Relentless Pursuit of Winning Podcast
Release Date: 12/09/2025
The Relentless Pursuit of Winning Podcast
🔥 Excerpt "Emotions happen before the thought, and until you release what is stored in the nervous system, strategy stays blocked." ⚡ TL;DR Rochelle Carrington breaks down why founders can know the strategy, keep executing, and still feel stuck. She explains how Emotional Release targets the emotional patterns embedded in the nervous system that shape focus, decision making, sleep, and stress responses. The conversation reframes burnout as a signal, not an identity, and offers practical ways to name emotions, notice triggers, and regulate what you feel so performance comes from safety and...
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🔥 Excerpt “What if the thing you gave up on was never meant to be given up on, and it’s still waiting for you.” ⚡ TL;DR Breaking limiting beliefs requires more than motivation. In this conversation, Rick Torrison shares how faith shaped his understanding of belief systems, identity, and the inner narratives that quietly direct behavior. The episode explores how unchallenged beliefs create ceilings in life and leadership, and how replacing them with truth opens the door to sustainable growth. 📄 Show Notes Breaking limiting beliefs sits at the center of this conversation. I sat...
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🔥 Excerpt Culture isn't an assembly of perks or policies. It is how people experience leadership when things get uncomfortable. ⚡ TL;DR TJ Butler shares how founders build an employee retention culture by taking responsibility for leadership behaviors, communication rhythms, and people systems that scale. This episode explores the benefits of Fractional HR, why retention is rarely an HR problem and how culture lives or dies at the top. 📄 Show Notes Employee retention culture should be part of every company's growth strategy. It is something you either build intentionally or pay for...
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🔥 Excerpt “Motivation will go away. Discipline is doing the work even when you don’t want to.” ⚡ TL;DR Marc Fitzwater, retired Green Beret and founder of I-68 Consulting Group, shares how pride refined by grace, discipline over motivation, and unwavering service shape leadership, entrepreneurship, and community impact long after military service ends. 📄 Show Notes Protector begins as a calling. It's not just a title. Marc Fitzwater joined me carrying the quiet authority of someone who has lived under pressure for decades. Ten deployments shaped his understanding of...
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🔥 Excerpt “Put down the microscope and pick up the mirror.” ⚡ TL;DR Dr. Greg Stewart shares how emotional intelligence shapes leadership, marriage, and personal recovery by helping you name negative emotions, measure what is actually at stake, and do the inner work before you try to fix the people around you. 📄 Show Notes Emotional intelligence is not a soft skill. It is the line between a leader who grows and a leader whose strengths start doing damage. In this conversation, Dr. Greg Stewart and I talk about what happens when identity and worth get tied to outside validation, and...
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🔥 Excerpt "You do not manage people, you lead people." ⚡ TL;DR Jordan Modiano and I talk about what it means to lead people while running multiple missions at once. We break down fear versus anxiety, how values guide decisions when the answer is not obvious, and why clear communication protects teams from speculation. Jordan also shares how his daughter inspired Races for Autism and why founders have to build support systems that keep the plates spinning without losing themselves. 📄 Show Notes Lead people. That is the thread Jordan Modiano kept pulling on, whether we were talking...
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🔥 Excerpt “This framework lowers risk because it starts with knowing exactly who your offering is for and why it matters.” ⚡ TL;DR Greg Licciardi joins the show to unpack the Holy Grail of Marketing, a disciplined framework designed to help founders reduce risk, stop wasting marketing dollars, and build clarity around their unique selling proposition. The conversation explores white space, message clarity, timing, brand purpose, and the importance of maintaining human connection as AI becomes more prevalent in marketing execution. 📄 Show Notes The Holy Grail of Marketing is not...
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🔥 Excerpt Never cheat yourself. If you value what you create you need to get paid accordingly. ⚡ TL;DR Marcel Clarke shares how an entrepreneurial mindset is built through ownership, disciplined pricing, systems, and long term thinking. From franchises to commercial cleaning, real estate development, and investing, this conversation centers on responsibility, discomfort, and building assets that last. 📄 Show Notes Entrepreneurial mindset is not motivational language. It is the discipline to own outcomes, price work honestly, and build systems that hold up under pressure. Marcel Clarke...
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🔥 Excerpt “The less I know about something, the more I can create a breakthrough.” ⚡ TL;DR Alan Gregerman explains how innovation is fueled not by having all the answers, but by knowing where certainty limits progress. We explore curiosity, fast experimentation, leadership humility, and how founders can build innovation systems that stay relevant as the future unfolds. 📄 Show Notes Wisdom of Ignorance is not about lacking intelligence. It is about recognizing that real innovation often begins where certainty ends. In this conversation, Alan Gregerman reframes what it means to lead,...
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🔥 Excerpt "If you want to stay in charge of your business and if you want to be hip deep in the day to day details, keep just giving orders and do not let them think for themselves." ⚡ TL;DR Ral West shares how she and her husband scaled a Alaska to Hawaii travel business into eight digit revenue, stepped back from daily operations, and later sold to Alaska Airlines. She breaks down six principles that helped them scale without burnout: systems, measurement, leverage, culture, team alignment, and customer delight. 📄 Show Notes Owner's Mindset is not a slogan. It is the shift that lets...
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“Community is sacrifice. You put a little of yourself into it so people can find belonging that makes their hearts grow.”
⚡ TL;DR
In this episode I sit down with community strategist Todd Nilson to explore what it really takes to build digital spaces that feel human, safe, and alive. Todd shares how his journey from recruiter and lifelong gamer to community architect shaped the way he designs online environments that fight loneliness and deepen belonging. We walk through how to plan a community, enroll early champions, set healthy guidelines, and think clearly about monetization so founders can use community as a long term asset, not a quick campaign.
📄 Show Notes
When I invited Todd Nilson into the studio, I expected a conversation about technology and platforms. What I experienced was a masterclass on belonging.
Todd opened by sharing his path into the community world. Performing arts, journalism, tabletop games and early social media all pointed him toward one big question. How do we create spaces where people feel seen and connected. That curiosity became a career in designing online communities that feel cozy, purposeful, and human.
He described the loneliness he sees in the world and how thoughtfully designed communities give people a place to land. One example that stayed with me was a large quit smoking and vaping community he helps support. Members tell him they are alive because that space exists. They find practical tools, emotional support, and grace when they slip. Hearing that reminded me why our work with founders has to reach beyond revenue into real human outcomes.
We then dug into the work behind communities that thrive. Todd talked about sacrifice as the core of community building. You invest time, attention, and care before the benefits show up. That means clarifying the purpose of the space, talking directly with the people you want to serve, and shaping a clear journey for their first thirty days.
Todd walked me through a simple way for founders to think about community strategy. Start with a very specific niche. Speak with early members and let their needs inform programming, events, and even platform choice. Invite a small group of committed people first, your willing co conspirators, and build momentum with them before opening the doors wider.
We also talked about norms and safety. Todd sees community guidelines as a form of hospitality. When expectations are clear and modeled by early members, people relax and share more freely. That is where deeper stories, richer learning, and real loyalty begin to form.
Finally, we explored monetization. Todd encouraged founders to treat community as a long term program that supports the entire customer life cycle. That can include membership fees, courses, or premium circles inside a broader space. The key is to charge in ways that keep the community sustainable while honoring the value people receive.
For founders who aim to build stable, sustainable companies with a real sense of connection around the brand, Todd offers both vision and practical next steps.
✅ Key Takeaways
- Digital communities can ease loneliness and create powerful belonging when designed with empathy and intention.
- Community building requires sacrifice, consistent presence, and clear purpose before results appear.
- Early members set the tone, so recruit people who love the mission and will show up often.
- Thoughtful guidelines and modeled behavior create safety, which opens the door to deeper conversation and trust.
- Monetization works best when it sustains the space and aligns with the long term value members experience.
👤 Bio
Todd Nilson is a community strategist and founder of Clocktower Advisors. For more than fifteen years he has helped organizations design, launch, and manage online communities that deepen connection for customers, employees, and mission driven groups. His work spans tech firms, nonprofits, education initiatives, and large behavior change communities focused on health and wellbeing.
🧭 Chapters
00:01 Welcome and why Todd’s work matters
02:24 From journalism and performance to digital community
06:20 Online connection and the future of belonging
12:24 Games, storytelling, and the spark for community work
18:00 Leaving agency life and launching Clocktower Advisors
21:54 Impact stories and saving lives through community
24:18 What it really takes to keep a community alive
26:47 Designing a founder community from idea to experience
34:05 Guidelines, norms, and healthy responsibility
40:37 Monetization models and making community sustainable
44:03 Final advice for founders on playing the long game