First things first, LET’S GO BEARS 🐻

What’s in the Loop this week:

Scott Kitun has spent his career at the intersection of media, creators, and private markets, spotting categories before they break out. Last week, he joined Chicago-based GigaStar as their Chief Business Officer to help turn YouTube creator revenue into an investable asset class.

Here’s our conversation:

SK: Sometimes other people have better ideas than you.

As it was put to me by the investor who re-introduced me to Hazem, “Scott, have you heard of GigaStar? It’s like if Republic and Songfinch had a baby.”

That was it. Then I spoke to Hazem (GigaStar CEO) and immediately knew I could step into a role immediately.

SK: Retail interest in private markets has never been higher – institutions know this, just look at the $50B+ invested in RWAs, infrastructure and asset acquisition in 2025. Then, look at the advancements in tokenization – happening right here in Chicago with Edward Woodford and ZeroHash.

Lastly, if you ask 10 high schoolers what they want to be when they grow up, 9 will say influencer or YouTube. It’s not a niche anymore – it’s a viable side hustle or full time income for top creators.

SK: I think distribution will always matter. The more you have the more you’ll make.
But a huge distribution with minimal engagement or high churn will always earn less than a smaller distribution with amazing engagement. So as is always the case in any business, growth matters, repeat is where the margin’s at.

Creators have more opportunities than ever before, and taking advantage of them requires capital. That’s where financial infrastructure plays a huge role. For GigaStar we believe that creators have always been on the wrong end of the deal and nearly every other imaginable industry with $200+ billion in value has a purpose-built financial system – and yet – creators do not.

So like any business you’ve invested in, creators must focus on creating a great product and distributing it, then accessing capital in the most efficient way to scale it.

SK: Candidly, the fundraising here still sucks. Firms like Drive Capital and yourself have helped and we have more active seed investors than ever, but largely that’s where it ends. Risk appetite is still way below what it needs to be for absolute success here.

That said, Chicago is incredible. People live in Chicago but do business everywhere. When I was coming up everything was Chicago-centric, fundraising, marketing, growth, then you’d hub and spoke scale to the next big tech city. Now you live or HQ here and are sitting on a panel in Dubai. Business is global here in a way that it wasn’t even as recently as 2022.

All the first principles quoting SF VCs love to tell you about how constraints lead to innovation. Try building with no capital. That is real constraint.

Chicago investors miss out by not making large bets, coastal VCs miss out by trying to apply the Midwest discount, but that is changing and I truly believe much of fintech and creator economy does in fact come through Chicago: Edward (ZeroHash), Steven Galanis (Cameo), Kristy Ross (TastyTrade), David Kalt (Reverb), Alex Jones (Hallow), Hazem and so on.

SK: I think AI makes it both easier than ever and harder than ever to scale a business – anyone can build anything. When you see the opportunity to acquire a strong user base with durable product, do it. Then build on top of it. It is much easier to execute that than going zero-to-one.

From an investor standpoint, perhaps less upside, but far less risk and likely very good ROI; just ask our friends over there at (Chicago-based) Shore Capital

SK: I spot trends early. I can determine what is inevitable versus a tough sell. Songfinch was like that. Super obvious hidden demand.

I like spaces that are inevitable but lack attention. It’s harder to raise, but less competitive from the onset, which gives you more time to build and a faster path to owning a significant portion of the market. You also know pretty fast whether unit economics and demand are what you thought. If it fails, you move on quickly with minimal damage.

Being first to market is an incredible advantage and as tech becomes a commodity, it may be the only advantage.

Data is still coming in for 2025 but here’s the high level:

Chicago startups raised over $1.84B across 141 deals in 2025.

2025 saw fewer deals but larger and higher conviction investments, a sign of a more disciplined market.

For our growth equity ecosystem, Chicago companies raised $5.32B in the first three quarters, surpassing the $4.32B raised in all of 2024.

After a quiet 2024, 2025 delivered:

Two standout exits:

Chicago’s economy is diverse (a win) and 2025 data reinforces that, but there were three sectors that stood out more than others

I’ve been saying for a while that Chicago is shifting from a single hub to focused founder-led ecosystems.

Examples: mHUB (hardtech), Portal (life sciences), Cube (Web3/stablecoins), Density Collective (founders), Drive Capital (AI)

These are physical communities aligned around talent, capital, and customers by sector.

Follow me on Twitter and Instagram