A burgeoning group coaching company helps professionals navigate challenges.
In the modest apartment where Anita Hossain Choudhry WG’15’s parents first settled in South Carolina nearly 50 years ago, the dinner table was the heart of family life.
“My parents would tell these incredible stories about their time in Bangladesh,” she recalls. “Someone would cut a mango from the tree and bring it down—it was so vivid. I remember as a kid feeling like I was transported back to Bangladesh.”
Those dinner-table stories, told by immigrant parents who initially got by on her father’s graduate student’s chemistry stipend while raising three children under five, planted the seeds for what would become Hossain Choudhry’s work: creating spaces where people can be vulnerable about their struggles and find community in shared experience.
Today, she is the CEO and cofounder of The Grand, a group coaching platform that’s combatting what she calls “the loneliness epidemic.” Founded in 2019, The Grand matches groups of six to eight people navigating similar transitions—like new parenthood, career changes, leadership challenges—with an executive coach to guide them. The company works with start-up founders, company managers, athletes, and more. This fall, they launched The Grand Pursuit, a coaching journey specifically for entrepreneurial mothers.
The premise is simple: that the executive coaching typically reserved for Fortune 500 leaders should be accessible to everyone, delivered in group settings where participants realize they’re not alone in their struggles. “It’s more accessible than executive coaching and we not only focus on group coaching but also community,” Hossain Choudhry explains. The company has built a digital platform where members can access content and coaching tools.
But getting there required abandoning her original definition of success.
Growing up, Hossain Choudhry internalized the idea that good grades, prestigious schools, and fancy-sounding jobs were the surest measures of a person’s worth. After earning her Wharton MBA a decade ago, she seemed to have done all the right things to make her relatives proud—ascending from assistant vice president at Deutsche Bank, where she managed over $400 million in Latin American investment portfolios, to a position as head of knowledge at First Round Capital, one of Silicon Valley’s most influential early-stage venture capital firms. “I was very much in that orientation,” she reflects. “Are you getting good grades? Are you getting into top schools? Do you have a respectable job? That’s how you measure success.”
At First Round, her job was to convene founders to share knowledge with each other. But she noticed something troubling in those gatherings. “Everyone was talking about all the things that were going right—Oh, I’m crushing it, things are awesome. It felt a little not helpful and not authentic—because we know the founder’s journey has so many ups and downs.”
The breakthrough came when she created guiding principles that gave founders permission to share more vulnerably. In one session, a participant opened up: “I have an executive coach, and I have a therapist. Those two things have been game-changing for me.”
“That’s when everyone started talking about their self-worth, self-doubt,” she recalls. “Am I good enough as a founder? These are the mistakes I’m making. Everyone felt less alone on their journeys and felt like they had that support system of people who really get it.”
Despite loving her role and coworkers at First Round, Hossain Choudhry decided it was time to move on. That decision marked a turning point for her—from pursuing accolades and external validation to a mindset that treated experiences as experiments. Her parents, both educators, were supportive but cautious. “They’ve always taught us, believe in yourself, you can do it, go for it,” she says. Though, she adds with a laugh, “My dad still asks me when I’m going to get a PhD.”
The spark for The Grand came during walks with her cofounder Rei Wang, with whom she’d bonded at First Round over the challenges of navigating unfamiliar territory. “We kept coming back to loneliness,” Hossain Choudhry says. “We in our lives had moments of feeling alone—being first-generation, being the first to do a lot of things, being women. There were a lot of moments where we were the only ones or we were the first.”
A 2023 advisory on loneliness by US Surgeon General Vivek Murthy, along with a 2021 study that found that Americans report having fewer close friendships than in decades past, have amplified their mission. “That shocked us because community has been such a big part of both of our lives and how we got to where we are,” she says. “It was all about the people and the networks and the friends and the support systems.”
That’s why The Grand settled on a group-based approach to executive coaching.
“It’s the difference between show versus tell,” Hossain Choudhry says. “When I was a coach working one-on-one, I could tell someone, ‘Everyone has imposter syndrome, this is the research.’ But if you hear someone in your group say, ‘Every day I’m unsure I’m going to keep my job because I don’t know if I’m doing anything right,’ suddenly someone puts words to exactly how you’re feeling. That is so powerful in helping you feel less alone.”
The model has attracted investors including Reddit cofounder Alexis Ohanian, whose venture capital firm Seven Seven Six led a $4.7 million seed funding round two years ago. “I was fundraising twice while pregnant,” Hossain Choudhry notes, emphasizing how crucial it was to find partners who supported them as humans, not just business leaders.
Today, working from her home office in Milwaukee, Hossain Choudhry measures success differently than she did at Deutsche Bank. “When I did a values exercise through The Grand, I realized that meaningful relationships are the thing I value most,” she says. She traces that realization to a piece of feedback she once received in finance: that she was “too nice.” Her boss at the time told her not to listen—to be authentic, that it would serve her well.
“Building meaningful relationships is so core to who I am,” she reflects. “Once I was able to realize that and align my leadership in that style, it became a lot more natural.”
On her desk sits her most treasured possession: a book her husband created for her 40th birthday, which she celebrated in February, filled with letters from friends and family about the impact she’s had on their lives. It’s based on an exercise The Grand uses called “best self-reflection,” a fitting symbol for someone who has reoriented her professional aspirations around helping others discover their authentic selves.
Last May, Hossain Choudhry attended her 10-year Wharton reunion, calling it “one of the best weekends of my life, because it reminded me of the power of being with such thoughtful, introspective, intellectual people.”
Her advice to current students reflects her evolution since graduating: “Follow your curiosity. A lot of times we tend to go down a path we think we’re supposed to, but the moments when you follow what’s sparking your interest, that’s when you’re able to make the most meaningful change.”
—Tasmiha Khan
