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Y Combinator S19 Demo Day Recap

I had the privilege of attending Y Combinator's Summer 19 (S19) Batch this past August. I had a wonderful time, and thought I would recap my experience there. Unfortunately, I only could attend Day 1. Maybe I can stay for both days the next time I get a chance to go.

Y Combinator President Geoff Ralston kicks off Demo Day S19!

Day 1 was filled with 84 companies presenting (a total of 166 startups presented across two days). Each startup had two minutes to woo investors and the media with why their startup was going to be the next big thing in their respective industries. There were so many founders saying "We are the X for Y" that I lost count. But hey, it's an effective, concise way to convey what your company does in a brief pitch.

Around noon, there was a two hour break where attendees (media and investors) got to mingle with the presenters (founders). I had the pleasure of running into Jessica Li, an investor at Soma Capital and a great friend of mine and former colleague at Rough Draft Ventures, and Priya Rajan, Managing Director of Silicon Valley Bank who hosted the SVB Trek this year!

Jessica and I at Demo Day! What a long road from RDV to here!

Priya and I reconnected here at Demo Day! It was amazing seeing her again :) SVB has been a wonderful support network. I miss them and my fellow Trekkies!

It was great catching up with these two ladies. After the break, we went through the remaining startups to present. One of the coolest things was meeting some of the founders of the companies I profiled leading up to Demo Day on Forbes (Simmer and Flo Recruit).

I was impressed by the passion of the founders and their drive to leave an impact on the world through their company. This is something that Michael Seibel (CEO of Y Combinator) talked heavily about during our Media Roundtable - thank you to Kat Manalac and Lindsay Amos for hosting this! I loved it. From what I could tell, his and the other YC partners efforts were having a clear and positive effect on how founders went about ensuring their companies were a force for good.

I really enjoyed meeting journalists from over publications as well, like TechCrunch and Business Insider. I'm hoping in the future I can make better connections with them as my peers and colleagues in the tech reporting ecosystem.

Here are my three main takeaways from S19 Demo Day as a whole:

  1. Founders support one another: Given my front-row seating during the presentation, I was able to see founders give each other high-faves and pats on the back as they switched on and off the stage to present. These brief interactions showed to me that even though everyone had been head down working on their companies for the past three months, they still kept supporting one another till the very end. Founder camaraderie is a wonderful thing to observe, even in the midst of a hyper-competitive place like Silicon Valley. The key observation here is that Y Combinator must also consider how much a prospective startup and its founders wanting to join the program will support and benefit others in the batch. This is similar to how elite colleges sculpt their incoming freshman classes year after year.

  2. YC seems to be a reunion: I was expecting to see a lot more competition between investors as they tried to talk to all the companies they wanted to invest in. Those rounds only go unfilled for so long when it comes to YC startups. That wasn't the case. Investors were mingling with one another in between chatting with startups they saw present throughout the day. There were a lot of hugs and smiles exchanged as people caught up with one another. Maybe they hadn't seen each other in a while, or co-invested in a company recently. Given how competitive it can get to get on the cap table of some of the best companies, it was cool seeing investors relaxed and friendly. The key observation here is that if YC is the reunion, one guess is that the action (competing to invest in the hottest companies) had already happened well before Demo Day. I won't expand on this too much - I don't want to speculate or spread rumors here. I'll leave it at its nice to see investors having a good time.

  3. Founders face the same problems: I had the chance to speak to founders throughout the day. I got to ask them questions about what it took to arrive here at Demo Day with their startups ready to graduate from the program. I heard similar answers with varying shades and hues, but one founder solidified it for me: "Man, we're all facing the same problems when we're building our companies." Hearing that confirmed my long-held suspicions from my time covering a variety of companies (from biotech to blockchain) on Forbes. These founders face the same challenges in hiring, scaling, fundraising, customer acquisition, etc. The key observation here is that founders learn best from other founders. If only they had access to advice in the form of content that they could always point back to if they needed help...

Well, that's all I have for now. Hope to attend both days next time if I get invited again.

Next blog post: My Future With Forbes!


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