Scaling Laws: the Midwest Playbook

“To chart a truly epic journey to scale, you need to make everyone you enlist a hero, not just in your story, but in their own.” — Reid Hoffman, founder of LinkedIn.

How you scale something is how you scale everything. Clubs, companies, communities — all the same. Without a clear winning vision, hardworking individuals, and a culture of unreasonable support, no organization can survive its competition and scale to incredible heights.

To be clear — I have never founded or led a company before. But in the last year and a half, I got a glimpse into what it’s like to scale an organization by growing my own community at UChicago. In this article I will share my observations and what I believe are fundamental laws to scaling a great organization.

Windy Beginnings

In my first year of college, I met my cofounder Diego Scanlon at a Polsky Center social event. The Polsky Center is UChicago’s entrepreneurship department in the Booth School of Business. Often, Diego and I would attend their 200+ person talks but found it impersonal due to the sheer size of the events. When we tried to make founder friends by joining clubs on campus, we found it was harder to get into than UChicago itself. Most clubs (esp. finance and consulting related clubs) require applicants to submit extensive essay responses and go through 2–3 rounds of interviews before facing exceptionally low acceptance rates. I personally got rejected from 5 clubs in my first year. This means that at UChicago, there was no easy way to engage with founders, student VCs, and talented students interested in entrepreneurship without digging deep into pockets of small social networks.

So, Diego and I thought about how we might reform this landscape. We identified three key issues hindering students’ ability to collaborate in and learn about entrepreneurship. 1) There was no landing pad — if someone wanted to meet talented founders or wished to learn about venture or fundraising, they do not know where to start besides visiting the Polsky Center, where we personally struggled to form connections. 2) There was no easy way to discover startup teams on campus — if someone wished to work on a startup with UChicago students, the College New Venture Challenge (CNVC) teams would normally be their best bet. These are teams handpicked by the Polsky Center to participate in its accelerator program. But CNVC is a small pool of companies among many others that are not publicized, leading to a number of missed opportunities. 3) There was a lack of social and learning opportunities surrounding startups. Generally, only a handful large events featuring alumni founders are hosted by the school in a year, and speaker events and socials hosted by clubs yield little to no fruitful results because they’re not intentional. By fruitful results, I mean students actually forming teams to work ideas, or existing teams receiving real venture funding.

Since neither the school nor anyone else was going to create our dream community, Diego and I decided to make our own. We called it “Windy Ventures”, a lighthearted name with a sense of place (colloquially, Chicago is called “The Windy City”, and Diego actually came up with it). In the first few months of us starting the community, I hustled to make sure that Windy addressed those three key issues.

Windy is a landing pad for all. Exclusivity hinders collaboration and learning. But to create the best experience, the scale of our events needed to be small. For our first couple of roundtable guest events, I kept the size to 15–20 students, and let them lead the conversation with our guests (our first was Anthony Khaiat, who is now at Kalshi, and second was Max Keenan, founder of Aurelian). This garnered a lot of interest and I distinctly remember a couple of participants shaking my hand after the event, applauding me. I knew from that day that this was the right way to go.

Windy is UChicago students’ chief of staff. Founders operate at lightning speeds, but the school moves slow. If a student wanted to meet a student founder, they would have to go through many sub-pages on the CNVC website to find an infrequently updated Airtable of companies. With us, you just shout what you need in our WhatsApp group. CNVC requires founders to take a quarter-long course on entrepreneurship, when that three-month period is a lifetime for founders and can be crucial to building their product or acquiring new users on the ground. In contrast, our venture partners are (with past work experience at a16z, DRF, Techstars, JP Morgan, and more) and I am available via text essentially 24/7 for our founders; I’ve answered calls at 11PM to help founders who wanted to prep for their YC interview. We also make introductions for founders on a weekly basis to investors in our network and keep their interests at heart, not the investors. This level of commitment and responsiveness sets us apart from all clubs and institutional accelerators at school.

Windy builds a life-long community. Genuine connections and learning is only possible with a close-knit group of likeminded people. In my first year, I made the effort to introduce myself and explore the interests of every member in my community over coffee. Today, our expanded team of 7 have coffee chats with 10+ students a week, striving to make personal connections rather than impersonal video calls. At social events, we intentionally mix student founders with scouts and VC partners from all over the region to create organic connections. Our latest event included scouts from Contrary and Soma, and partners from DRF. Our future plans include holding workshops to help founders build faster and short-form videos that tell UChicago founders’ startup stories.

Since our founding 1.5 years ago, we have helped tens of startups find cofounders, pivot, make fundraising decks, get funded by LTF Ventures and Y-Combinator — and we’re just getting started. To be sure, we could not have achieved this without sticking to a winning vision, talented individuals, and a culture of unreasonable support.

Scaling Fundamentals

Vision

Vision is one of the three most important things one needs to build a great organization. Without a clear vision, an organization cannot focus on the right things, so no fruitful results are achieved, and members lose morale — the organization dies. But vision comes with the ability to build conviction, and to build conviction you need to have a scout mindset. Let me explain.

My vision for Windy was to create a “home” for all entrepreneurial minded students at UChicago. By “home”, I mean a place where they can socialize, learn from the best minds, get feedback on their ideas and products, and receive tier-one assistance from student partners, mentors, and investors. After discovering the gap in UChicago’s entrepreneurship ecosystem, I had enough conviction to get started. After the first, second and third event, more and more students became interested, and my conviction grew stronger.

Of course, not every event was successful — like hosting a crypto after party at a frat house. This is why having a “scout mindset” is crucial. This term, coined by the writer Julia Galef, urges us to have a truth seeking mindset in which we view reality as they are, not as we wish they were. By constantly updating our worldview and iterating the user experience to match it, we can create truly wonderful experiences. For us, we learned from the crypto event to stick to small-scale, intimate events rather than large, grandiose parties, even if we wanted to scale the community quickly. Turns out, scaling a close-knit community takes a lot of time, and it’s not something that can be done in an evening’s time. The scout in me corrected my view and once again put me back on track to realizing Windy’s original vision.

Talented, Hardworking Individuals

Having smart, hardworking individuals on your team is the second most important thing one needs to build a great organization — because a single person is not enough manpower to bring vision to life. But other than the obvious quantitative advantages a team brings, more voices mean that the club improves qualitatively as well by “pushing and pulling” on ideas.

Windy Ventures moved rather slowly when it was just me and Diego running the show. For instance, we hosted only 7 events last year; this year, we are on track to do 20 events. I could only have a handful of coffee chats each week with founders on top of a rigorous course load and internships, but my venture partners and I can triple this figure while having a wider reach into different networks.

My partners have, time after time, pushed and pulled on my ideas and undoubtedly steered the organization into a better direction. Jack told me to stick to our values and keep any group chats and communication open to the entire school, instead of screening each new member. Alex suggested and opened up new channels to share our writings. Eric opened up new collaborations with UChicago blockchain/crypto clubs and pushed for an interconnected job board. The team members have each challenged the community’s established practices and improved them in many ways.

Culture of Unreasonable Support

Culture is the last essential ingredient to a winning organization. Without culture, an organization risks of dying. Peter Thiel famously told Brian Chesky, the founder of Airbnb, “don’t f*ck up the culture” after he had raised Airbnb’s Series C from Thiel. Thiel invested in Airbnb in part due to its strong culture, but he had a somewhat cynical view that it was practically inevitable to “f*ck up” once a company gets to a certain size.

I agree with Peter. Culture sets the foundation and is what sets it apart from another organization that may provide the same exact product or service. For instance, other clubs on campus also generally support founders. Some are incubator programs, others give non-equity funding. But none are as dedicated and hustlers for our founders as us. We support founders for its own sake because we truly want to foster a better entrepreneurial environment. We set ourselves apart in the details: we send a before and after note to participants for every speaker event; we post across social media to promote products or requests from our founders; we establish good relationships with national and international VCs to give warm introductions for UChicago founders; we work around the clock to get things done for our founders. Our culture is being unreasonably dedicated to our community members, to furthering entrepreneurship at UChicago, and making startups just a little bit easier for our founders.

Midwest’s Future

The Midwest is brimming with entrepreneurial talent — just look at the students emerging from top universities like UChicago, Northwestern, and UIUC. Yet, despite this potential, the region struggles to reclaim the vast reserves of capital currently flowing to the coasts. Windy Ventures is one early step toward strengthening our fragmented ecosystem, but it will require collaboration from students across top Midwestern universities, support from key academic institutions, and partnerships with investment funds around the country to truly thrive.

The numbers tell the story: although the Midwest hosts 22% of America’s Fortune 500 companies, it captures only 5% of total U.S. venture funding. A mere five cities — San Francisco, New York, Boston, San Jose, and Los Angeles — account for 67.5% of all U.S. venture capital. Chicago ranks ninth as of December 2023, and some of the nation’s largest pension funds, including Wisconsin’s $132 billion WRS, call the region home. Yet iconic venture firms like a16z and Sequoia rarely plant roots here, leaving students less aware of opportunities in startups and VC. Without adequate guidance and engagement, many young innovators default to traditional career paths. Meanwhile, the few Midwest-based venture shops often operate in isolation — rarely sharing deal flow or actively engaging with university campuses — while their West Coast counterparts regularly host events and build relationships on-site.

Over the last year and a half, however, I’ve seen a promising shift: the rise of student “scout” programs breathing fresh energy into our campuses. For example, serving as a scout for Soma Capital has not only allowed me to grow as a leader at my own university but also connected me to likeminded peers across the Midwest. Building on that experience, I intend to redouble efforts during my junior year and experiment with new initiatives to continue to build a more robust ecosystem:

1. Empower Every Scout to be #1: Reid Hoffman’s advice on scaling organizations emphasizes the importance of empowering individuals within the organization, not just promoting the organization itself. Each person on the journey to scale should become a hero in their own right at their respective schools, rather than solely focusing on making the overarching organization heroic. Teaching Midwest scouts scaling fundamentals — put founders first, be unreasonably supportive, and set a winning vision — can lead them to become “heroes” in their own communities.

2. Foster Interconnectedness: Rather than mirroring the closed-door approach of some Midwest VCs, we aim to form a “mafia” model — think the PayPal Mafia, but for students. By sharing resources, lessons learned, and opportunities, scouts across universities can accelerate one another’s growth. A tightly knit network of young innovators working together can produce results far greater than the sum of its parts.

3. Provide Better Resources and Education: We must arm students with accessible guidance — from Y Combinator’s free materials to lessons from alumni and guest speakers. By elevating the quality of entrepreneurial education, we’ll help new founders move beyond “tar-pit ideas” and tackle real problems. The goal is to blend domain-specific college knowledge with practical, real-world application. The form which this takes on could be a venture studio or a fellowship, but that’s subject to more investigation.

This is a moment of profound opportunity. By connecting dedicated scouts, tapping into the region’s existing capital, and nurturing an environment that values genuine collaboration, we can lay the groundwork for a renewed Midwestern entrepreneurial renaissance.