I met Brecken Glenn through the Bailey Program for Family Enterprise, and within minutes I knew her story would resonate with so many next-gens navigating what’s next in their family business journey.
Four and a half years into working at Affinity Partners—her family’s real estate development firm in Northern Colorado—Brecken is already asking the hard questions most people don’t ask until a decade in: Am I here because of my last name, or because I belong here?
The Path She Didn’t Plan to Take
Brecken grew up thinking she’d never touch real estate. “I actually grew up thinking I would never be in real estate because that’s what my family had did,” she told me. She loved the financial side and understood real estate was an incredible tool for generational wealth building. But she was determined to carve her own path—investment banking, alternative assets, anything but the family business.
Then COVID hit. She graduated early, started working as a real estate assistant on the commercial brokerage side—intentionally staying away from her dad’s development focus—and something unexpected happened. She fell in love with development.
She was geared up to pursue a master’s in finance at CU Boulder, less than a week from classes starting, when she had a defining moment.
“I had never really quit something in my entire life,” Brecken shared. “I’m an oldest daughter. I’ve always been involved in athletics and was on a Division One team in college. And I’ve never quit anything in my life.”
But standing at that crossroads, she asked herself: What does Brecken want? Not what looked good on a resume. Not what she thought she do. What did she actually want?
She wanted to be in the business. So she made the ask.
Earning Your Seat—Twice
When Brecken asked if they’d hire her full time to work on the development side, she wasn’t asking because of her last name. She’d shown them her work, proven her value, and identified where her passion intersected with what the business needed.
“I felt like I had shown them what my work was capable of, but they were under no obligation to actually keep me on the team full time,” she said. “It was very validating that what I was doing was a benefit to the team.”
That validation mattered. When your name is on the wall, you’re carrying weight most people don’t see. Early on, she made a bold choice: she asked to be introduced only by her first name in business meetings. Not to reject her legacy, but to prove she belonged on her own merit.
The Work of Defining Yourself
What strikes me most about Brecken’s story is how intentional she’s been about creating boundaries and building her own leadership identity—without losing connection to the legacy that shaped her.
This is exactly the kind of work that gets skipped in most transitions. The conversations that don’t happen. The boundaries that don’t get set. The identities that don’t get honored. And that’s where transitions fall apart—not in the legal documents or the financial structures, but in the relationships.
When I asked what she’s chosen not to inherit, she struggled with the question—not because there aren’t things worth leaving behind, but because the lessons she’s learned feel timeless and worth carrying forward.
“You’re advocating for yourself, for your community, in whatever role you’re in,” she said. “You’re advocating for your partners, your investors, your colleagues. You are stepping up to be there, to be that leader and support people.”
A First of Her Own
When I asked Brecken what she’s the first of in her family, she paused. She’s used to defining herself as second or third—third-generation developer, second generation in this company.
But then: “I am the first woman in our family to step up into this role.”
The first to create this particular path.
The Work That Actually Matters
Brecken’s story reminds me why the relationship work in family business transitions isn’t optional—it’s foundational.
She navigated identity, proved herself, set boundaries, and built trust—all while learning the technical side. The people piece made the business piece possible.
Business owners spend $150-200K on lawyers and CPAs for their transition, but 60% still fail because they skip the people side. The conversations about who wants what. The clarity on what’s next beyond the business. The boundaries between family and leadership roles.
Brecken and her family are doing that work now while they’re building something together. Not waiting until transition is forced by timeline or circumstance.
This is building your Transition Roadmap—getting clarity on where you’re going, how you’re getting there, and that the people you care about are moving forward with you. It’s the strategic foundation work that happens before you spend six figures with advisors who might be solving only part of the problem.
If This Resonates With You
If you’re a next-gen trying to figure out if you belong, how to set boundaries, or how to build your own leadership identity while honoring legacy—Brecken’s story is for you.
If you’re a business owner watching your successor navigate these same questions and wondering how to create clarity without forcing an exit you’re not ready for—this work matters for you too.
The best transitions happen when both generations build the roadmap together, when hard conversations get facilitated with expert guidance, and when everyone knows what’s next for them personally—not just what’s next for the business.
