Tiffany Dufu on Raising $4 Million, Building Community, and Why Every Founder Needs a Crew

For Tiffany Dufu, becoming one of the first Black women founders in the United States to raise more than $1 million in venture capital wasn't the result of one pitch meeting or one breakthrough. It was built over years of non-profit fundraising experience, an unwavering commitment to advancing women, and a deep belief that success is never achieved alone.

Before founding The Crew, a peer coaching platform that matched ambitious women into accountability groups, Dufu had already spent years raising millions of dollars in the nonprofit world. She eventually raised $4 million in venture capital to grow The Crew before the company was acquired by Luminary in 2023. Today, she serves as President of the Tory Burch Foundation, helping women entrepreneurs build and scale their businesses.

On this episode of The First 200 Podcast, Tiffany shares candid lessons on fundraising, leadership, pivots, acquisition, and why community became her greatest competitive advantage.

Watch the full conversation on the YouTube player below, or listen on Apple Podcast, Spotify, Amazon Music, or wherever you get your podcasts.

https://www.youtube.com/watch?v=acNuWXCEJcQ

Below are edited excerpts from our conversation with Tiffany Dufu, highlighting some of the biggest lessons on fundraising, leadership, and building a lasting company.

What inspired you to start The Crew?

Tiffany Dufu: The company started after a woman challenged me on advice I kept giving. I would tell women, "You need to find your crew"—a group of people who will hold you accountable and help you achieve your goals. One woman stopped me and asked, "Where exactly am I supposed to find these people?" That question exposed a real problem. I realized women didn't just need advice—they needed access to community. That became The Crew.

Before raising venture capital, how did you prove there was demand?

Tiffany Dufu: I didn't start with software. I created a simple landing page and asked women to apply. Hundreds signed up almost immediately. I manually interviewed applicants with help from my own friends, matched the first 100 members myself, and charged $499 before anyone even met their group. Those first membership fees funded our first engineer and proved women were willing to pay for the solution.

What gave you the confidence to raise venture capital?

Tiffany Dufu: My confidence didn't come from startups—it came from fundraising. I had already raised millions for nonprofit organizations, so I knew how to ask people to invest in a mission. What I needed to learn was how venture capital worked. I immersed myself in investor conversations, studied pitch meetings, and found mentors who taught me what investors were actually looking for.

What was the hardest part of raising your first $1 million?

Tiffany Dufu: Learning the language of venture capital. I didn't know terms like "traction" or understand why investors cared about things like waitlists. One mentor helped me translate my business into the metrics investors wanted to hear. Another lesson was knowing when to close the round. One of my crew members told me, "If you don't close soon, investors will think you can't close." That advice pushed me across the finish line after seven months of fundraising.

How many investors rejected you?

Tiffany Dufu: One hundred and eighty-three. Rather than treating every rejection as failure, Tiffany used each meeting as research. She paid close attention to recurring questions, refined her pitch, and let investor feedback strengthen both her presentation and the business itself.

You were a solo founder. Did that ever become a disadvantage?

Tiffany Dufu: People often told me I needed a co-founder, but I never believed someone should be added just to satisfy investors. Instead, I surrounded myself with exceptional operators and advisors who complemented my strengths. Leadership isn't about doing everything yourself—it's about building the right support system.

Why did The Crew eventually pivot from consumers to businesses?

Tiffany Dufu: As the company grew, customer acquisition became more expensive. Selling directly to individual women became increasingly difficult to scale. Corporate partnerships allowed entire organizations to provide The Crew as a benefit to employees, dramatically lowering acquisition costs while expanding the company's reach. The shift ultimately positioned the business for acquisition.

What happened after COVID changed everything?

Tiffany Dufu: Before the pandemic, every Crew met in person, limiting growth to cities where enough members lived. Once meetings became virtual, geography no longer mattered. Instead of matching women by city, The Crew could match members anywhere in the country within the same time zone. What initially felt like a crisis became one of the company's biggest growth accelerators.

What surprised you most about building a venture-backed company?

Tiffany Dufu: Raising capital changes your focus. Early on, I spent all my energy understanding customers and solving their problems. As the company grew, more attention shifted toward metrics, fundraising, hiring, and preparing for future rounds. That's part of building a venture-backed business—but it's important not to lose sight of the mission that inspired the company in the first place.

What advice would you give founders raising capital today?

Tiffany Dufu: Ask for help. Almost every breakthrough in my career came because someone invested their time, introduced me to the right person, or believed in me before everyone else did. Leadership isn't about having all the answers. It's about inspiring people to believe in a shared mission. If your vision is compelling enough, people will want to help you build it.

Listen to the Full Conversation

Tiffany's journey demonstrates that fundraising is about much more than convincing investors. It's about building trust, solving real problems, and surrounding yourself with people who help you become a better founder.

In the full episode, Tiffany shares the complete story behind raising $4 million in venture capital, scaling The Crew from a simple idea into a venture-backed company, navigating acquisition by Luminary, and why she believes community remains every founder's greatest advantage.

Watch or listen to the full episode of The First 200 Podcast for the complete conversation and more founder stories from the women who changed venture capital history.