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The Distill - Uncomfortable Truths
Fundraising reality checks, student startup showcase, and building community one event at a time.
Greeting Pioneers,
Following an electric Slack thread, Rachel fires a hot take on fundraising.
Then, two community recaps—one from the wild, and one from our own backyard.
Your Gender Isn’t Why You Can’t Raise Money
As a Female Founder….
On every panel. Every networking event. Every mentoring call with young women founders. The same conversation comes up: "It's so much harder doing what you’re doing, as a woman.”
The predictable questions: "With 98% of venture capital going to men, how did you advocate for your business as a female founder?" "Can you recommend VCs that only invest in women?" "What barriers did you have to break down?”
Hot Take: I don’t think being a woman is why it was hard for me to raise, it’s not connected to why I ultimately got funded, and I don’t think it’s why you are or aren’t getting funded either.
Every time someone shares that 98% stat—usually with a lot of righteous anger about how unfair everything is—another group of capable women decides the game is rigged before they've even tried to play.
Most Companies Are Not Venture Backable
Hearing "this isn't venture-backable" doesn't mean your product sucks or you're a bad founder. It just means you don’t fit their math.
Most companies are not venture backable.
VCs invest expecting most companies to go to zero. For their fund to work, the few winners need to be massive. We're talking billion-dollar exits, not $100 million ones.
Here’s why your $50M dream might as well be a zero to a VC:
Investor XYZ has a $200M fund. You want them to invest $1M for 20% of your pre-revenue company. If you sell for $50M in five years, they make $10M. Sounds good?
Not to them. They'd need twenty of those exits just to return their investors' money. Before fees. No profit.
Meanwhile, one company that sells for $20B like Figma? That single deal returns their entire fund.
That’s why VCs only invest in businesses with the potential to become absolutely massive. Not just successful. Massive.
If you're building something VCs wouldn't fund regardless of who's running it, gender isn't your problem. You're pursuing the wrong financial instrument.
Stop Looking For External Outs
I’m the solo female founder of Swell Health. We’ve raised $1.6M since we started three years ago. None from VC’s with a thesis on female founders – they all told me no.
It took nearly a year to close our seed round. I talked to 350 investors. I had plenty of male and female peers trying to raise at the same time who couldn't. The men blamed their location. The women blamed sexism. Most talked to fewer than 10 investors.
The reality is I haven't once heard someone say that sexism is the issue and then found a sparkling investable company underneath.
Instead, there were clear red flags: part-time founders, no product, no traction, no revenue, no go-to-market strategy beyond Google ads and prayer, small markets, linearly scaling costs.
These are why investors pass. But blaming gender and the midwest is easier than admitting your business model doesn't work yet.
This topic surfaced in the KYX slack this past week, and the struggling founders had obvious issues: using consultants to pitch for them, running multiple businesses simultaneously, targeting organizations that don't even invest. These aren't gender problem, they’re basic fundraising mistakes.
Some investors have bias. I've seen it. But if that’s your primary explanation for why you can't raise, you're probably missing the real issues holding you back.
It's more empowering to look at what you can do, what's within your control, than to default to a place of helplessness that you cant do anything about. If you’re a woman and you need money for your startup, better figure out what levers you can move to make it an impossible deal to say no to.
You Signed Up for This
Even if fundraising is harder for women, you signed up for this.
Want to build a venture-scalable company? Need capital? It’s your job to get it.
That 98% stat is misleading. It's not 100 women competing with 100 men, where only 2 women get funded. Women start fewer venture-backable companies in the first place.
Women start more lifestyle businesses, partly due to cultural factors (yes, systemic sexism). Women are underrepresented in tech roles where people see venture-scale opportunities. They carry more home and childcare responsibilities, making 80-hour weeks harder.
But obsessing over that won’t get you funded. VCs want the same returns regardless of the barriers you’ve faced.
You have two options:
A) Believe fundraising is rigged. Give up early because the system is unfair. Don't get funded.
B) Accept it might be harder. Work twice as hard to make your business undeniably good.
One gets you funded. One doesn't.
I chose B. So did every successful founder I know. Woman or not.
-Rachel
🏆 The 2025 Brown-Forman Cardinal Challenge
It was a fantastic evening at the Speed Art Museum, and a big win for the Louisville startup community.
Quarterbacked by Jack Manzella, the Brown-Forman Cardinal Challenge shined a spotlight on the most promising startup ventures emerging from the University of Louisville. This year, 12 teams competed for a record-breaking pool of funding and services, made possible by generous in-kind sponsorships from community partners.
“The Cardinal Challenge meant a lot to me this year. As a student, I once competed in the event and for the past four years as Entrepreneur-in-Residence, I’ve helped plan it. This year, we decided to take a fresh approach.
Based on years of student feedback and personal experience, we reimagined the event from the ground up. We asked ourselves: What does success look like for student founders? The answer led us to shift the focus from judgment to maximizing mentorship, and from generic prize money to sponsor-backed services that directly support venture development beyond graduation.
Instead of handing out checks to the best presenters, participants applied for funding tied to specific needs, and we matched them with sponsors whose services aligned with those needs. Each team was also paired with several mentors, not to assign scores, but to offer meaningful guidance and build relationships that last beyond the event.
We extended the showcase portion to allow guests more time to meet teams and ask questions, and we reduced the duration of pitch presentations. This gave every participating team a chance to share their story with the full audience, not just the “top three.” We also added QR codes to all showcase and dinner tables so every attendee could give feedback, not just a select group of judges.
This year’s Cardinal Challenge featured tens of thousands more in prize funding and in-kind services and twice as many mentors as previous years. The level of mentorship and community involvement was something I was incredibly grateful for.
The result? More feedback, more support, and more genuine connections than ever before. I am excited to see where these entrepreneurs will be in a few years and proud that the University of Louisville, and the Forcht Center team, had the vision to shake things up to better support them.”
Jack’s leadership and the team’s willingness to rethink tradition paid off. This year’s Cardinal Challenge didn’t just feel different. It was different.
More energy. More intention. More meaningful support for the founders who showed up. A thoughtful evolution of a strong program and a solid step forward for Louisville’s startup community.
Congrats to all involved.
🪩 Cinderblock’s First Event: Pizza, Coding, Poker, and a Packed House
We hosted our first event at Cinderblock last week. First event from our own home base. First time we played host instead of guest.
And—somehow—it went shockingly smooth.
Perfect amount of pizza. Just enough chairs. Wi-Fi held strong. Even the vibes cooperated. Well… except for the poker table getting a little too rowdy at times. Apologies, vibe coders. Once we’re fully moved in, we’ll relegate the high-stakes hooligans to the cage (a.k.a. the conference room).
It felt good to host our own event on our own turf—to offer hospitality, curate a vibe, and see what happens when you give people space to connect and create.
Founders, engineers, operators, and venture in one room—talking shop, shipping product, swapping stories, and shoving chips.
Zaid built the HackKentucky website. We gave tours. Made intros. And added another name to the Block roster.
Momentum is building, and we're just getting warmed up.
See you next month. It’s only getting better.
Know someone who should read this? Forward it, or send them this link.
That’s a wrap 🎬
Keep showing up 👊
Keep shipping 🚢
Peace, Pioneers ✌️