Hosted by Scott Kelly of Black Dog Venture Partners, the VC Fast Pitch series has run for over 15 years and helped founders raise more than $130 million. The VC Fast Pitch on Thursday, May 7 gives founders five minutes to pitch and five minutes of Q&A from the investor panel. That’s it. It’s a brutal format — and a useful one. Five minutes forces founders to make hard choices about what actually matters. As an investor, it forces me to do the same.
So here’s what I’ll be listening for through the Redtail Capital lens, and what I’d encourage every founder pitching that day (or any day) to think about.
1. Can you tell me what you do without making me work for it?
The first 60 seconds of a pitch are diagnostic. If I have to translate jargon, infer the customer, or guess at the business model, you’ve already lost ground. The founders who win the VC Fast Pitch format open with a sentence that a smart non-expert could repeat back accurately. That’s not dumbing it down — that’s clarity. Clarity is a leadership signal.
2. Is there a real problem, and does the market care enough to pay?
I’m not looking for “big TAM” theater. I’m looking for evidence that someone — a specific someone — is feeling pain right now and willing to pull out a credit card or sign a contract to make it stop. Pilots, LOIs, early revenue, waitlists with real names. One concrete proof point beats ten slides of market size.
3. Why you, and why now?
Founder-market fit is real, and it’s underrated. I want to understand what you’ve seen, lived, or built that makes you the right person to solve this problem at this moment. “Why now” is the timing question — what shift in technology, regulation, behavior, or cost structure has made this possible (or necessary) today that wasn’t true three years ago?
4. Do the unit economics tell a believable story?
I don’t need a perfect financial model in five minutes. I need to believe you understand how the business makes money. What does it cost to acquire a customer? What’s the lifetime value? Where does gross margin land at scale? Founders who can answer these crisply — even with honest “here’s what we’re still figuring out” caveats — earn trust fast.
5. What would you do with the money, and what does it buy you?
The raise isn’t the goal. The raise is fuel for a specific milestone that increases the value of the business. Tell me what milestone, by when, and why hitting it changes your trajectory. Vague “scale the team and grow marketing” answers tell me you haven’t done the work yet.
6. Are you coachable without being a pushover?
This is the one I can only assess in the Q&A. When the panel pushes on a weak point, do you get defensive? Do you collapse and agree with everything? Or do you engage thoughtfully — concede where the critique is fair, push back where you have data or conviction we don’t? The best founders I’ve backed are intellectually honest. They don’t need to be right; they need to get to right.
A note on the partnership philosophy
At Redtail, we don’t do win/lose deals. If a founder, an investor, an employee, or a customer has to lose for the deal to work, we don’t proceed. So when I’m listening to a VC Fast Pitch presentation, I’m not just evaluating the company — I’m evaluating whether this is someone I’d want to be in the trenches with for seven to ten years, and whether the structure of what they’re building creates wins for everyone touching it.
That’s a higher bar than “is this a good investment.” It’s the right bar.
The InSoCal lens on the VC Fast Pitch
Most of what I just wrote is investor-side. But through InSoCal CONNECT, the nonprofit that helps connect startups with their community, I also see this from the other direction — founders preparing for these moments, often without the network or the reps to know what investors are actually evaluating. If you’re pitching at the VC Fast Pitch on May 7 (or any time soon), the single highest-leverage thing you can do this week is run your pitch in front of three people who will be honest with you. Not your spouse. Not your co-founder. Three people who will tell you exactly where they got lost.
That’s the work.
See you at the Fast Pitch VC on the 7th.
Register to attend the May 7th VC Fast Pitch here: https://www.eventbrite.com/e/may-2026-online-vc-fast-pitch-tickets-1985732427144
VC FastPitch: https://vcfastpitch.com/
Scott Kelly’s LinkedIn: https://www.linkedin.com/in/blackdogceo/
