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Celebrating The Most Founder-Friendly Investors in Chicago
We’re excited to reveal the winner of the Founder-First Award, recognizing investors who go beyond just writing checks—they become true partners to founders, offering unwavering support, mentorship, and strategic guidance. This year’s award celebrates investors who prioritize the long-term success of their portfolio companies and act as dedicated champions for founders at every step of their entrepreneurial journey.
Why We’re Celebrating Founder-First Investors
As any entrepreneur will tell you, having a supportive investor on your cap table is crucial. The right investor doesn’t just bring capital—they bring strategic value, industry insights, and a network that can make or break a startup’s growth trajectory. That’s why we’ve curated this list of Founder-First Investors—to highlight those who consistently go the extra mile for founders. These are the investors who are in the trenches alongside you, offering guidance during tough times, helping you scale when the opportunity arises, and connecting you to customers, partners, and follow-on capital when you need it most.
Having the right mix of investors who believe in you as much as they believe in your business can make all the difference when navigating the startup ecosystem. A founder-first investor is someone who doesn’t just back your vision—they advocate for you, push you to grow, and open doors to opportunities that may have otherwise been out of reach. We believe these types of investors are instrumental to a company's long-term success, and they deserve to be recognized.
Winner: Desiree Vargas-Wrigley - Velocity Catalyst / P33
This year’s Founder-First Award goes to Desiree Vargas-Wriley, a tireless champion for founders and a leader at Velocity Catalyst / P33. Desiree has dedicated herself to empowering underrepresented founders, helping them gain access to critical resources, networks, and opportunities. Through her work with P33 and Velocity Catalyst, Desiree has become a cornerstone of Chicago’s startup ecosystem, fostering a culture of inclusivity and growth.
"Desiree has been an invaluable partner to early-stage founders, consistently prioritizing our needs and visions with a unique emphasis on fighting for the overlooked underdogs in Chicago. With a hands-on approach, she offers strategic guidance, connects founders with crucial resources, and provides unwavering support through the highs and lows of startup life. Her commitment to putting founders first has been instrumental in the success of numerous pre-seed ventures, including my own, making her truly deserving of the Chicago Founder-First Investor Award."
Finalists
We also want to celebrate the incredible contributions of our finalists, all of whom have made a significant impact on Chicago's entrepreneurial landscape:
- Fund: Lightbank
- Investment Thesis: Seed & Series A investments in legacy consumer and SMB markets.
- Check Size: $500K - $5M
- Notable Investments: Ohana, Hark, Wendy
"I can't say enough about Jyothi... the founder journey is full of ups and downs (as we know). Through every single point, she's just there. Whether email, making intros, picking up phone calls, strategizing - I've been on with her until very late in the night working through things and have texts from her early the next day with more momentum or questions. It's evident how bad she wants to see us succeed.. Incredibly lucky to have her in our corner!"
- Fund: Allianz Life
- Investment Thesis: We make investments in companies with market traction and a demonstrated ability to drive innovation.
- Check Size: 500K-$5M
- Notable Investments: Empathy, Ezra
"Collin is special for several reasons. First, he listens. There are a lot of problems that come with innovating, especially in the technical industry, such as retirement. Collin has consistently built trust with me by listening carefully before generously sharing his network to help. Second, he is generous. Over the years, he's worked hard to build respect within the startup ecosystem, especially within insurance, which can be very valuable to any enterprise. Whenever he's had the opportunity, Collin has consistently delivered high quality and made timely introductions to help us accelerate our growth. I've seen how he organizes panels/conferences, conducts due diligence, and makes introductions firsthand; however, his talent has always been obvious to anyone. I would bet that Collin has the opportunity to help change the world through his investments, and it's only a matter of time before he starts one of the best-performing funds in our city."
- Fund: Long Jump Capital
- Investment Thesis: LongJump is a first-check, founder-led fund. There are generational businesses that do not yet exist because the founders who can build them here, in the Midwest, have lacked sufficient capital and connectivity to get them off the ground. We are industry agnostic and invest at the earliest stages when funding, access and mentorship are crucial
- Check Size: $100k
- Notable Investments: Evergreen, Eventnoire, Sanarai, Science on Call, Rivet.
"As a founder, I’ve experienced firsthand the exceptional support that sets LongJump apart. What makes this team truly unique is that all of the General Partners (GPs) are founders themselves. They’ve been in our shoes, so they understand the challenges we face (the ones that are easy to talk about, and the ones where silence speaks better). This deep empathy translates into tangible support. Whether it’s a quick call for guidance on sales strategies, go-to-market plans, product direction, or fundraising advice, their expert help is just a call away—often within the same day. More importantly, they are always our first call or text when something goes wrong or when we need input on crucial decisions. Their advice is invaluable, and their commitment is unmatched. This combination of empathy, community engagement, and intentionality is what makes this firm exceptional. They are more than investors; they are true partners, mentors, and advocates for founders."
These investors have demonstrated a deep commitment to founders, not just by providing capital but by building meaningful, lasting relationships that help startups thrive.
Investors Who Support the Chicago Ecosystem
Beyond this year’s winner and finalists, Chicago’s vibrant startup ecosystem is powered by an entire community of founder-first investors who are dedicated to helping startups succeed. Here’s a list of additional investors known for their founder-friendly approach:
- Jason Felger
- Fund: Long Jump Capital
- Investment Thesis: At Jump Capital, we invest in early-stage founders solving critical problems in fintech, application software, and infrastructure software. We prioritize solutions that drive efficiency, enable smarter operations, and de-risk enterprises, paving the way for future growth and transformation.
- Check Size: : $1-10M
- Notable Investments: M1, LogicGate, Acretrader
- Mark Phillips
- Fund: 11 Tribes
- Investment Thesis We are an early-stage venture fund with a mission to be the firm where capital and care are focused on the founder. Investing in the following verticals:: B2B SaaS, Healthcare, Future of Work, Cybersecurity, Fintech, AI
- Check Size: $250-750k
- Greg Barnes
- Fund: Hyde Park Ventures
- Investment Thesis: We invest in software companies led by founding teams who have experience in their industry. We most often invest in SaaS, marketplace, and tech-enabled software companies.
- Check Size: 500K to $5M
- Brian Luerssen
- Fund: Long Jump Capital
- Investment Thesis: At Jump Capital, we invest in early-stage founders solving critical problems in fintech, application software, and infrastructure software. We prioritize solutions that drive efficiency, enable smarter operations, and de-risk enterprises, paving the way for future growth and transformation.
- Check Size: : $1-10M
- Notable Investments: Cycle.io, Quantitative Insights
- Brett DeMarrais
- Fund: Ludlow Ventures
- Investment Thesis: We are Generalist investors, mostly software, but stay sector agnostic on purpose so we can be founder centric.
- Deploying out of Fund 5 - $50M
- Check Size: $1-1.5M
- Notable Investments: Honey, Angelist
- Steve Miller
- Fund: Origin Ventures
- Investment Thesis: Origin Ventures is an early-stage venture capital firm investing in software, hardware, and marketplace businesses in the Digital Native economy.
- Check Size: $250K-6M
- Notable Investments: Cameo, Burq,
- Kevin Willer
- Fund: Chicago Ventures
- Investment Thesis: We're the early partner to Founders in industries overlooked by others. We write high conviction checks. We take board seats. We're a Founder's biggest advocate while being straight shooters. We promise we'll put in the work, and ask Founders to hold us to it.
- Check Size: $500K to $5M
- Notable Investments:
- Constance Freedman
- Fund: Moderne Ventures
- Investment Thesis: Moderne Ventures is a strategic venture capital and growth equity firm investing in technology companies in and around the multi-trillion-dollar industries of real estate, finance, insurance and sustainability. It has both a Fund and an Industry Immersion Program, the Moderne Passport, designed to foster innovation, partnership and growth between industry partners and emerging technology companies.
- Check Size: $1M to $7M
- Notable Investments:
- Ezra Galston
- Fund: Starting Line VC
- Investment Thesis: Starting Line is an early stage Chicago based Venture Capital fund investing in premier consumer startups & brands
- Check Size: $500-$3M
- Notable Investments: Cameo, Attain
- Chris Girgenti
- Fund: Pritzker Group
- Investment Thesis:
- Check Size: $500-$1M
- Notable Investments: Machinery Partner, Fuel Me, Lessen
These investors have built reputations as trusted partners for entrepreneurs, helping founders not only raise funds but also navigate the complexities of scaling a business in a competitive market.
Angel Investors
In addition to venture capitalists, Chicago boasts a growing group of angel investors who are passionate about supporting early-stage startups. Notable angels include:
- Andy Dunn
- Michelle Hayward
- Julie Novack, PartySlate
- Maria Katris, Built In
These angels have played pivotal roles in guiding early-stage companies through their first crucial years, often serving as mentors and advisors alongside their financial investments.
The Importance of a Founder-First Investor on Your Cap Table
Choosing the right investor is about more than securing funding. It’s about finding someone who believes in your mission and who will champion you through thick and thin. Founder-first investors provide invaluable mentorship, open doors to future opportunities, and offer strategic advice that can help you avoid common pitfalls.
Having supportive investors on your cap table means having a team that’s aligned with your vision, ready to offer assistance when challenges arise, and focused on your long-term success rather than just short-term returns. These investors act as your advocates, sounding boards, and problem-solvers, helping you stay focused on building a business that lasts.
That’s why we’ve put together this list—to celebrate those who lead with empathy, build trust with founders, and truly add value beyond the capital they provide. These investors are not just financiers; they are partners, and their support is often the difference between a startup that merely survives and one that truly thrives.
Congratulations again to Desiree Vargas-Wriley and all the incredible investors who continue to make Chicago a leading hub for innovation. Keep your eyes on this space as we continue to celebrate the individuals and teams pushing the boundaries and making Chicago’s startup ecosystem stronger every day!
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