Desiree, or as those of us close to her call her, Desi, is a veteran of the Chicago tech community.

She created the very first crowdfunding platform, GiveForward, long before GoFundMe existed. GiveForward helped raise more than $200 million for vulnerable people facing major life events, and she raised capital from the likes of First Round Capital, Pritzker Group, and others.

She later went on to create Pearachute in 2016, the largest aggregator of family-friendly activities in the world. We live in a time today when being off our phones and spending time in real life is seen as a rare luxury, and we celebrate the mental health benefits that come from it. Once again, Desiree was ahead of her time.

Most recently, she joined P33 as Chief Innovation Officer, where she created and led the TechRise program. That's where we went from being friends to becoming colleagues as well.

The story of me joining P33 also has a lot to do with Desiree. A few years ago, I was at her birthday party. I wasn't looking for a new job at the time, but we started talking about life and careers, as you do late at night at Joy District, of all places. I told her about my vision of creating Chicago's own version of South by Southwest (SXSW). She then told me about P33. I ended up meeting the executive team the following week and was recruited to join shortly after, where I created TechChicago Week and ultimately fulfilled that SXSW vision.

So much of life comes down to being in the right place at the right time, and so much can happen from a random conversation.

Today, Desiree is the Founding GP of Velocity, her own $50M fund that invests $250K to $500K in pre-seed companies and $1M to $5M in emerging fund managers.

Desiree earned her BA from Yale University.

On my 25th birthday, I had a lightning bolt moment that led to me founding the world’s first crowdfunding platform, where we primarily helped people going through a major illness or the loss of a loved one.  For many years, I naively thought that I was put on this Earth to build that platform, to help people heal and show up for each other in a way that had never been possible before. It was a calling that gave me a sense of purpose I had never known…until I married my husband, we had children, and I deepened my relationship with family and friends. 

I realize now that meaning for me is found in the exchange that happens between people for which we feel deeply connected. Those connections can be lifelong and unconditional, binding to our hearts, as they are with my husband and children. But they can also be short sparks of creativity, laughter, and joy with strangers, friends that grace our lives for a short while, and the people we work with. 

Meaning for me is making sure I step out of the unintentional numbness of the day to day to truly be present in those exchanges. 

I used to believe that worrying and stress was a necessary byproduct of success, that to achieve your goals, you had to be so maniacally obsessed with the problem you are solving that you will walk through walls. 

But my first startup had a lackluster exit, and I did all of those things. I worried, I walked through walls, I made miracles happen that kept us alive against all odds. On paper, we failed. But in reality what I did was pick myself up, dust myself off, and I went on to build Pearachute, TechRise, the Josephine Collective, and now Velocity Catalyst Funds. 

Success is rarely achieved through brute force. It’s a layered system of growth, measured over time by the impact we have on others and the courage we have to build something bigger than ourselves.

Ambition without purpose can be misappropriated by greed. And greed is the enemy of true progress. It puts us in unhealthy competition with people we care about, separates us from family and friends, takes from others so that we can have more.  

But ambition that aligns with a deep sense of purpose, that touches our true “why,” creates a flourishing of prosperity that ripples through our companies, our team, our communities, and world.

The approval of others. Full stop. I’ve wasted so much energy worrying about whether I was smart enough, nice enough, ambitious enough, sophisticated enough in my work. As I’ve matured in life and career, I realize more often than not, the people whose approval I sought weren’t worth my time and attention. 

On a more personal level, and perhaps embarrassing to admit, but marriage is the answer to the latter. Nearly every family member of mine is divorced, so I did not have role models of what profound commitment looked like. But 16 years in, I can say that a partnership rooted in complete trust, transparency, and love can overcome even the most life altering challenges.

In 2014, I stepped down as CEO of my startup to hire a “more seasoned operator” to run the company.  People thought I was giving up on my company, and I felt I was letting other women founders down who looked up to me. But the truth was that I was a mess. 

We’d tripled revenue every year, and then only doubled. A man from my past tried to sue me for a large part of the company and my co-founder, while still involved, had moved back to California. I was under tremendous stress constantly, and I really wanted to have another baby. 

I knew that I couldn’t possibly bring a life into the body that was ravaged and broken by years of founder mode. So I agreed to give up the CEO title and almost immediately got pregnant with my youngest son. 

In hindsight, I realize that I was in burnout, and it cost me my company. It’s one of the main reasons I care so much about the physical and mental health of the founders I work with. But I have zero regrets.

Loyalty. It’s not the shift from the gold watch to the Silicon Valley yearly ship jump that worries me…that was decades in the making.

There’s something different in the air right now. Founder relationships seem fragile, commitments between funders and founders are tenuous, terms sheets are getting pulled, and funds are failing to reengage existing LPs.

I’m sure part of it is the fear stemming from uncertainty of the AI revolution, but I’m looking forward to the days when people operate less from fear and more from loyalty and optimism.