What does this mean for startups?

This week's funding rounds are serving up a huge round, acquisitions, and a little bit of fomo. From fast delivery to Mira making every seed round look like peanuts, let's dive into the freshest capital infusions fueling tomorrow's game-changers!

Stubhub makes its NYSE debut with an IPO priced at $23.50, raising $800M at a $8.5B valuation; ticker STUB. Not the prettiest of debuts, closing at $21.80 (-9.80%) on Friday and sliding further to $18.80 (-22.69%) as of Tuesday.

I have had the pleasure of interviewing Shantanu Mehta… Over a month ago… my fault, but VERY happy to be able to bring this insightful chat to you all today. Shantanu is an investor at SPRING.

But what caught our eye was This post, the just inspiring story about two flatmates, with an idea, and no pressure, just trying their luck applying to YC.

This could have been a fairy tale story and they would have gotten expected, but I believe YC’s answer sparked something much larger than an acceptance. You're meeting Shantanu here first, because next time, you will meet him on a much bigger platform. Let’s dive in

1. From VC to Founder: What triggered your decision to switch sides of the table, and how did your time in venture influence the startup idea you pursued?

Cliché, but I’ve always known I’d be a founder someday. In January 2024, I’d moved to Toronto for an internship — my flatmate was at TD Bank, I was at American Express. One night around 10 p.m., we were on the couch talking about life, problems, and ambitions. I said I was terrible at speaking to women because I went to an all-boys school for 14 years. Isaac, on the other hand, had 2,000+ matches on dating apps but wasn’t satisfied with the quality of connections — he wanted to explore dating within his friend group, without making things awkward.

The YC deadline was 13 days away, so Friends to Lovers was born. Tinder but to date/fuck friends, not strangers.

2. 13-Day YC Sprint: Can you walk us through what those 13 days looked like, from ideation to application? What were the key decisions and trade-offs you had to make?

We knew 13 days was tight. But having worked in VC, I had a sense of what kind of early validation makes investors tick, and what we could realistically achieve in that window. My guess was that YC (or any investor) backing a 13-day-old idea would really care about only two things: (1) Speed, and (2) Proof of technical capability to build the product in the future — not a bloated MVP with 73 features.

For (1), I crammed in as many user interviews as possible (~30) — unbiased, with people from all walks of life — and built a soft waitlist.
For (2), Isaac built a scrappy, hard-coded mockup/demo. He’s a cracked SWE with some big names on his resume, including Boeing before the door blew off.

We were both working 9–5 jobs (more like 9-7), so our real workday was 7 p.m.–12 a.m. plus weekends. We told YC that — so even though we “did little” in 13 days, they knew how few hours we had and how much we were able to do in those hours.

Submitted the app two hours before the deadline.

3. Pattern Recognition vs. Gut Instinct: As a former VC, did your own filters for what makes a "VC-backable" startup change once you became a founder pitching to investors?

Yes and no.

Given how polarizing the idea was, my VC “pattern recognition” brain said this was risky, people might hate us. Honestly, if someone pitched it to me, I’d be concerned.

But I felt strongly about the problem. If YC thought we even had a 1% shot, they’d back us. You can’t care too much about what people think, amd you have to be a bit delusional to build something meaningful. The idea was controversial and had virality baked in. It was either going to blow up or go to zero.

4. Lessons from the Other Side: What’s something you wish more VCs understood about early-stage founders, now that you've lived that experience firsthand?

I wish VCs recognized that the founder knows the problem better than the VC. Most VCs say they recognize this but don’t act like it. I was often told my idea was the “worst thing” they’d heard, while others were overwhelmingly positive. Exactly what I expected: hyper-polarizing, no middle ground.

VCs are very good at many things: Pattern recognition, math, reading people, financial modelling. But they don’t know the problem better than the founder. As a VC today, I try to always give the founder credit and treat myself as a student of the problem when I speak with founders.

5. Operational Mindset Shift: What was the most unexpected personal or professional challenge in shifting from evaluating companies to building one from scratch?

As a VC, it’s easy to write a cheque, pass on (or unintentionally ghost) a founder, and scroll through a deck in <2 minutes. On the other side, it hits you. Founder empathy is everything.

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Here's what you've been waiting for: exciting job opportunities! To maximize your chances, remember these key tips:

That’s it for today, hope you enjoyed this as much as I did curating it, see you next week!
-Kev