From builder to backer: Desiree Vargas Wrigley on the playbook for resilient founders

Before she raised millions and reshaped Chicago’s venture landscape, Desiree Vargas Wrigley was waiting tables and pitching every customer she served.

Now the founding general partner of Velocity Catalyst and co-founder of the women-led angel group The Josephine Collective, Vargas Wrigley visited Residents and Tinkerers at The Garage’s Family Dinner to share what actually sustains a founder through years of uncertainty and rebuilding. 

“Your team needs you to be almost delusionally optimistic the entire time,” Vargas Wrigley told students. “When you have high conviction and you try every single thing, it’s amazing how many times miracles just happen for your business.”

Vargas Wrigley traced her founder journey back to 2008, while working in the nonprofit world. She had an “aha moment” after seeing the devastation of Hurricane Katrina a few years prior, when online giving barely existed.

“The only way to give online was to a big nonprofit, or to give to some person’s blog or PayPal. There was no social web, no peer-to-peer exchange of money, no Venmo and no Zelle,” Vargas Wrigley said. 

That gap led her to create GiveForward, one of the world’s earliest crowdfunding platforms and the precursor to GoFundMe. She told students that her first major fundraiser came directly from a customer at one of the tables she waited as she was trying to get the company off the ground. 

Her next company, Pearachute, took off quickly and even earned her a spot on Shark Tank. Pitching on national television forced her to sharpen her clarity, precision, and confidence in front of investors – skills she passed onto the students in the audience.

“What you need to do at any moment as you’re pitching is get to why they should care with their investment money,” Vargas Wrigley advised. “What unique insight do you have that you're capturing? You can get to the other stuff later, like why you are the perfect founder to build this. The quicker you can get to the substance of a pitch, the more respect you get.” 

The conversation soon turned to what it meant to be a female founder in fundraising rooms. Vargas Wrigley opened up about being viewed as the “cheerleader” of the business and investors assuming her male co-founder was the “numbers guy,” despite the fact that she had written every model and delivered the pitch.

She recalled the early days of GiveForward, where many investors dismissed the idea outright. “I basically got laughed out of the room,” she told students.

She learned quickly to lead pitches with insight, not identity, and later coached hundreds of Black and Brown founders to do the same during her time building TechRise at the innovation nonprofit P33. The weekly pitch program helped 400 founders raise about $200 million in follow-on funding.

Today, through Velocity Catalyst and The Josephine Collective, she is rewriting what early stage investing looks like in the Midwest. 

“If you're going to pitch me, I want to know what the unique insight is that you're bringing, and what are the converging macro-trends that are going to make this addressable market even bigger than it looks like on the surface,” Vargas Wrigley said. “That is the formula for me.” 

When her talk wrapped, a crowd of primarily female founders took her up on that offer. She stayed nearly an hour after Family Dinner, listening to pitches and answering questions one by one. 

She also left students with a grounding reminder about what the journey is really about.

“With these entrepreneurial journeys that we're on, you think sometimes that you're put on this Earth to build this one thing. That's truly how I felt about GiveForward. I thought it was my only reason for being,” Vargas Wrigley said. “But over time, it becomes about separating your identity and your ego from your startup and realizing that this is a career, not a single hit or a single swing.”