Nicole Stump works in venture capital, but her path there started in rural West Virginia, meandered through shelter work and high school teaching, and eventually became a study in how people find enough safety, structure, and capacity to show up for each other.

Brian and Nicole talk about what sustainable community actually looks like when people are busy and burned out from parenting, building companies, or simply trying to survive the season they are in. Nicole shares how nature, presence, birding, coffee walks, and low-friction local gatherings can help high-achieving people remember the "living" part of life-changing wealth.

The conversation moves from coal towns and Austin neighborhoods to classrooms, parent groups, founders, front porches, and communities that are allowed to end when they fulfilled their purpose. At the center is a practical invitation: you do not need permission to make something local, useful, and human.

Nicole on LinkedIn: https://www.linkedin.com/in/nicoleharbertstump/

Michael Kauffman is the founder of Catskill Crew, a local newsletter that has grown into a media company, events engine, product lab, and community platform for the Catskills. For Michael, the newsletter is only the beginning: a way to support local businesses, create reasons for people to gather, and build something that feels deeply rooted in place.

Brian and Michael talk about what it means to build a local media company that is community-led. Michael shares the winding path that brought him there, from startups and health tech to an existential reset on a fly-fishing trip that pushed him to stop chasing market opportunities and build something he wanted to run for the rest of his life.

The conversation ranges from rebuilding a Catskills town to matching venues with musicians, from seed swaps and local farms to the pressure of AI and screens. At the center is a simple argument: humans need nature, social life, and work that actually lights them up. One friend in the real world beats any number of connections in the metaverse.

Learn more about Michael's work at https://catskillcrew.com/ and https://thenewsletter.club/.

Tori Hanson has built her work around a simple but urgent idea: people need help finding each other again. After moving from the UK to New York and leaving a media career that included the New York Times, she found herself without the founder community she needed, so she started hosting co-working days for other entrepreneurs. Eight people showed up to the first one, and that small gathering eventually grew into The Knowledge Shop and the foundation for her event networking platform, Meet in 10.

Brian and Tori talk about how real community often starts through shared effort, whether that is working late shifts in a bar, moving overseas, building a company, or simply showing up to a room full of strangers. Tori shares why event hosts do some of the most stressful and underappreciated work, and how better tools can help people walk into events with more confidence, context, and permission to connect.

The conversation also explores why in-person experiences feel more valuable in an increasingly digital and AI-shaped world. Tori makes the case that events are becoming a kind of modern luxury: not because they are exclusive, but because choosing to be physically present with other people is becoming one of the most meaningful investments we can make.

You can connect with Tori on LinkedIn

And learn more about her passion projects at

Amanda Black is the founder of the Solo Female Traveler Network, a global community of more than half a million women saying yes to themselves, their dreams, and the kind of friendships that can form when people step into new places together.

Brian and Amanda talk about why travel creates such fast, deep connection: shared adventure, vulnerability, unfamiliar cultures, and the freedom to show up without the usual labels from back home. Amanda shares stories from her community, from women bonding around a table in Romania to an online network mobilizing across borders to help a traveler in danger.

The conversation also goes deeper into what community actually means. Amanda argues that community is not just a circle of friends or people who share your interests. It is often built through proximity, reciprocity, and inconvenience: taking someone to the airport, checking on a neighbor, showing up before there is anything to gain. In a world where so many connections are mediated by screens, Amanda makes the case for building communities that are safe, generous, and rooted in real life.

Connect with Amanda:

Instagram:

560k+ Facebook Group:

Website: https://thesolofemaletravelernetwork.com/

The Solo Female Traveler Network creates safe, culturally rich travel experiences for women, rooted in connection, curiosity, and shared moments that turn strangers into lifelong friends.

Instagram: @solofemaletravel

TikTok: @sofetravel

YouTube: @sofetravel

Ashley Engle is a multimedia journalist in Orlando who sees firsthand what happens when people choose to step out from behind their screens and show up for each other. She's covered everything from food drives to grief support groups, and the common thread is always the same: real connection requires real courage.

Brian and Ashley dig into why it's so easy to default to doom-scrolling when your couch is right there, and what it actually takes to build community — whether you've just moved to a new city, or you've lived there your whole life. Ashley shares how sitting alone at a coffee shop as a neighborhood reporter taught her that people are hungry to be heard, and that the best stories always start with someone willing to listen.

Ashley also opens up about losing her mother and how covering a story about the Modern Widows Club helped her navigate her own grief. Ashley and Brian explore why building trust takes time, why passion speaks louder than any reporter voice, and how serving others might just be the answer to an increasingly isolated world.

Follow Ashley on LinkedIn

https://www.linkedin.com/in/ashleyenglee/

What does it really mean live abundantly? Kristin Kenzy has spent her career at the intersection of business and human connection, and her answer might surprise you. For Kristin, the richest life isn't measured in bank accounts — it's measured in the depth of your relationships.

Brian and Kristin dig into why so many high-achievers feel isolated at the top, and what it takes to build the kind of genuine connections that actually sustain you. They talk about the moments that shifted Kristin's perspective — from chasing traditional markers of success to investing in the people around her.

The conversation gets personal when they explore how vulnerability plays into leadership, why saying "I don't know" can be the most powerful thing a founder admits, and how community becomes your real safety net when everything else is uncertain.

You can learn more about Kristin's work at

kristinkenzy.com