From Bold Questions to Big Shifts: Startup Boston Week Takeaways for Founders

Entrepreneurship rarely follows a straight line. Sometimes, movement begins not with a pitch deck or product launch, but with a single, unexpected question.  

For Denielle Finkelstein and Thyme Sullivan, co-founders of UNICORN, that question was posed directly to JPMorgan Chase CEO Jamie Dimon: 

      “Do you carry toilet paper around with you?”  

It wasn’t a throwaway remark. It was a challenge—a reframing of how we think about equity in the workplace. Why do we consider some essentials (like toilet paper) a given, while others (like pads and tampons) are still treated as optional luxuries? 

That moment sparked a conversation, then a commitment. Today, UNICORN products are stocked not just in Chase branches across the U.S., but also in other large organizations. 

Highlights from Startup Boston Week 

At this year’s Startup Boston Week, Fidelity Private Shares was proud to share the stage with Denielle and Thyme as they reflected on their journey—from a bold question to a bold business. Their story underscored five lessons that resonate across the founder community: 

1. Asking the Right Question

The Chase exchange shows how one uncomfortable question can reframe the conversation entirely. By asking Dimon whether he carried toilet paper around, Denielle highlighted the inequity of treating menstrual products as optional. That single question unlocked corporate commitments that propelled the company forward. 

2. Finding the Right Room

Founders often hear advice about “getting in the room,” but Denielle argued that finding the right room was most important. As she put it: “We had to reassess—what’s the problem here? The biggest issue was we didn’t surround ourselves with the right people. We were not talking to the right people.” 

For UNICORN, progress didn’t come from trying to be everywhere. It came from choosing rooms where their mission resonated—and walking away from those where it didn’t. 

3. Shifting from B2C to B2B

From the outside, their transition from B2C to B2B might look like a typical pivot. But for Denielle and Thyme, it was a full reorientation: moving from serving individual consumers to embedding equity into the operating infrastructure of large corporations. This shift required not only a new sales strategy but also a mindset change—one that allowed them to scale their mission. 

4. Fundraising Is Not Just Venture Capital

Thyme explained that their decision to avoid early VC funding was critical to maintaining flexibility. “Control as a startup founder is an incredibly important thing to maintain,” she said. “Because we hadn't taken venture, we could make a hard pivot.” 

Their story challenges the default narrative that VC is the only path to scale. For some companies, other approaches to funding create space for agility and independence. 

5. Support Matters

Capital alone wasn’t enough to carry UNICORN forward. What proved just as critical were allies who understood and amplified their mission. Founders need more than funding—they need partners who believe in their vision and help bring it to scale.

Fidelity Private Shares is proud to be part of that ecosystem by providing the equity management tools and partnership that helps enable founders to grow on their own terms. Schedule a demo to learn more. 

Challenge Assumptions to Grow 

As Denielle and Thyme’s story illustrates, entrepreneurship today isn’t just about scaling companies—it’s about reshaping norms. UNICORN proves that when founders challenge assumptions about what’s essential, entire industries can shift. 

1224377.1.0