When you meet Megan Brenn-White, you quickly realize she embodies a rare combination of sharp, strategic thinking, boundless curiosity and genuine care for people and place. Her leadership philosophy is rooted in connection, collaboration and a strong sense of purpose, all of which are reflected in how the team operates day to day.
These are the foundation on which she’s built the Upstate Curious Team at Compass. Since founding the team in 2019, Brenn-White has led them to become the No. 1 real estate team in the Hudson Valley and Catskills, New York, region, focused on the second home market, selling over $800 million worth of real estate and serving more than 1,278 clients (as of August 2025).
The team’s partnership with PLACE has led to explosive growth and far more robust systems, having gone from 11 agents at the start of 2024 to 35 agents and nine full-time staff members just a year and a half later.
For Brenn-White, that’s meant lowering stress, improving profitability and giving her agents access to benefits like premium health insurance, stock purchase plans and enhanced training — all while protecting the strong team culture that she feared they’d lose with growth.
From Park Slope to pastures
Brenn-White’s real estate journey began early; at just 22, she purchased her first apartment on a perfect brownstone block in Park Slope, Brooklyn, for $79,000. She now owns 10 homes upstate, most offered as short-term rentals she calls the “Curious Guesthouses.” That first single decision serves as a powerful example of how real estate can be financially transformative.
After earning her undergraduate degree from Harvard and a master’s from the London School of Economics, Brenn-White dove into the first dotcom boom, quickly moving into leadership roles for travel and community websites. Later, she launched a successful international marketing firm in New York City, serving higher education clients in more than 20 countries.
The Hudson Valley and Catskills began calling her. Brenn-White transitioned into real estate full-time — and in just a few years, she built one of the most high-performing, culturally cohesive teams in the region.
Culture by design
While many leaders talk about team culture, Brenn-White has built hers intentionally from Day 1. This isn’t a group of agents pulled together by happenstance or recruited solely for production numbers. Nearly all of their growth has come through Instagram and word-of-mouth, which means that new agents, staff and even clients are drawn to them by shared values and personality as much as by professional skill.
“We’re extremely creative, strategic, empathetic, caring and curious — of course!” Brenn-White said. That shared curiosity goes beyond market stats or transaction tactics. It’s about curiosity for people, their stories, their needs and the communities they live in.
The result is a culture that’s less about competition and more about collaboration. This shows up everywhere — from the way team members brainstorm in meetings, to how they share wins and challenges on Slack, to the casual coworking Thursdays that end with a sushi lunch.
“The culture of the team and the way we have fun together and support each other — which lets us support our clients and communities to a way higher level — is really my greatest professional accomplishment,” Brenn-White said.
Because their culture is so distinct, it acts as a filter. People who align with it thrive. And team members stay engaged because they’re surrounded by colleagues who are equally committed to doing great work and enjoying the process.
Meetings that matter
Covering a vast 14-county region, with some agents living two hours from each other, connection can’t be left to chance. The Upstate Curious meeting rhythm keeps everyone aligned and supported:
- Monday meeting (30 minutes): Brenn-White leads a focused conversation on what’s critical in the moment — from market trends she’s observing, to insights from conferences and coaching, to ideas the team can implement immediately. These always end with discussion and brainstorming.
- Weekly listing meeting (30 minutes): Led by the head of marketing, this is where active and upcoming listings are reviewed, marketing plans are fine-tuned, and creative strategies are developed for properties that need extra attention.
- PowerUps (twice weekly, one hour each): Agent-led deep dives on specific topics, from handling a bad water test to writing compelling listing descriptions. While attendance is optional, sessions are recorded and added to an evolving online training library.
- PLACE partnership calls: As a partner with PLACE, the team benefits from additional weekly meetings for personal development, operations and leadership.
All meetings are virtual, and cameras stay on whenever possible to preserve face-to-face connection. On Thursdays, the team hosts optional in-person coworking in a beautiful space run by a local architecture firm, followed by a standing sushi lunch — a simple tradition that builds camaraderie.
Keeping motivation high between meetings
In a geographically dispersed team, culture can easily fade between formal touchpoints. Upstate Curious combats this with daily micro-moments of connection:
- Slack ‘Happy Channel’: Celebrates wins big and small, from accepted offers to new babies. Team members also share photos when they meet in person — a reminder of the joy in working together.
- Peer support roles: Two experienced agents dedicate a few hours weekly to mentoring colleagues. One focuses on building personal brands and improving social media strategy, while the other coaches agents through challenges with listings, transactions, or clients.
- Robust administrative backbone: A nine-person operations team ensures agents have the systems, tools and marketing they need to focus on serving clients.
Adapting in a shifting market
After years in a seller’s market, the Hudson Valley and Catskills are shifting toward balance — and in some segments, toward buyers. Brenn-White is preparing her team to thrive in this new environment, with a focus on client education, expectation-setting and creative deal-making.
Equally important, she’s mindful of the emotional toll real estate can take — especially on highly empathetic agents. The team regularly discusses boundaries and strategies to avoid absorbing client stress, ensuring that care for clients doesn’t come at the cost of personal well-being.
Community beyond closings
Brenn-White’s vision extends far beyond transactions. For her, real estate is about connection, belonging and creating spaces where people feel at home in every sense of the word. That’s the driving force behind the Upstate Curious App, which has grown into a thriving community spanning 14 counties with more than 7,000 members.
What began as a way to better serve clients post-acquisition across such a large region has become a dynamic hub where long-time residents and newcomers connect, exchange resources and strengthen the social fabric of the Hudson Valley and Catskills.
A legacy in the making
With Brenn-White at the helm, the Upstate Curious Team has proven that you can grow fast without sacrificing quality, connection or joy. By staying rooted in values, building systems that support both productivity and people, and fostering a culture that attracts like-minded collaborators, she’s created more than a high-performing real estate business — she’s built a community.
In a market where change is constant, Brenn-White’s approach shows that the real edge comes from knowing exactly who you are as a leader, what your team stands for, and how you want to serve your clients and community. That clarity fuels everything from their daily Slack exchanges to multimillion-dollar philanthropic commitments.
3 key takeaways for your team
- Attract through alignment. Let your values shine in your marketing and operations so the right people — clients and team members
- Invest in both systems and soul. Pair operational excellence with cultural rituals that keep people connected.
- Protect your people. In emotionally demanding work, build structures that support mental and emotional resilience.
For Brenn-White and the Upstate Curious Team, success isn’t just measured in transactions closed or awards won — it’s in the way they show up for each other, their clients and the place they call home. And that’s the kind of success that lasts.
“Huddle Up” is a recurring column where teams across the country show us their meeting playbook.
Melanie C. Klein, M.A., is an empowerment and mindset coach.