What It’s Like on Day One of 500 Startups

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Remember that 'first day feeling'? One founder relives it right here. By Nichole Montoya (Co-founder & CEO, Cheddar Up)

This is part four in a series from one of our PITCH finalists documenting behind-the-scenes life at her growing startup Cheddar Up. Here are parts one, two and three.

Having recently spent a good chunk of time in San Fran only a month prior, I was looking forward to heading back for the first week of 500 Startups. Admittedly I had a touch of anxiety. But mostly I was extremely curious to see what all the hype was about. I knew I wasn’t going to necessarily fit in, but I was okay with that. That was the funny part.

Each phase of this startup has brought with it a plethora of stomach-dropping, anxiety-ridden and utterly amusing experiences. The upside of a startup is that I’m definitely “living.” There’s no going through the motions on this particular journey.

I would put my first week – and definitely my first day – at 500 Startups in the “utterly amusing” category. I doubt many others would describe it that way, but coming from the social circles of trunk shows and mom nights out – this was some entertaining stuff.

Like a Lost Kitten in a Hoodie

500 Startups has two offices in the Bay Area: San Francisco and Mountain View. Having just spent three months in the Valley, I consider us lucky to have been invited to the San Francisco batch. It turns out that the San Francisco office is in SOMA, two blocks from one of my favorite bustling parts of the city that’s always hopping. It also happens to be about eight blocks from where the authorities recently found a suitcase with random body parts. Regardless, the location is stellar.

I walk into the building at 814 Mission Street. None of my other teammates could join me for this first week for various reasons, so I was braving it alone. The building is nice, but somewhat no-frills upon entry. I hop in the elevator, which is clearly under some construction, with cardboard and duct tape for walls. As expected, all signs point to “startup scrappy.”

I was coming directly from the airport, schlepping my suitcase, arriving just on time. Upon landing at the 6th floor (top floor – it looks like the 500 office is currently the only tenant in the building), there’s only one door in which to enter.

The door is open.

I walk in and directly in front of me is a humongous 500 Startups logo painted on the wall. Too cool for school. I admittedly looked a little bit lost, but there’s pretty much mass chaos inside so not many notice.

People are milling about, but clearly most are heading to the central gathering point where there’s a big screen, a microphone and lots of chairs. Hmm…where to go, what to do… I at least needed to drop this darn suitcase somewhere. Just as I was having these thoughts a beautiful angel appears from the hallway with the biggest smile you’ve ever seen, “Hi, Nichole!” she bellows.

She introduces herself as Andrea and reminds me that we met at the Women 2.0 PITCH competition where I pitched in San Fran last fall. She went on to explain that she is going to be my “point of contact” (or POC) at 500 Startups. She was no longer doing the startup that she was working on when we met, and now she’s a mentor at 500. How cool is that?

She tells me to grab a seat for the official kick-off meeting. The rest of the morning is thoroughly entertaining and top-notch at the same time.

Paging Doogie Howser (Two Obsolete References)

The room becomes filled with LOTS of people — most are team members of teams accepted into the program. Lonely girl that I am, I’m simply entertained that I’m sitting in the 500 office – as a batch company, alone… amongst mostly 20ish males. I meet two really nice guys who sit next to me, wondering who let the old lady in. One of them looked 12. I’m not kidding. He looked 12. I suppose it’s possible that he was 12, but certainly there’s an age limit. But he also looked freaking brilliant. Where do they find these people?

Oddly, I’m not feeling at all insecure. I realize then that I’ve totally got something on these young men – LIFE EXPERIENCE. I’ve done a fair amount of pitching, I just rolled off of another similar experience, I’ve had entire careers. Despite the humor and unfamiliarity of it all, I know that “I’ve got this.”

So we all gather. The emcee is surprisingly polished in appearance – the only sign of “startup” are his white tennies paired with his cashmere sweater and blazer. Cool look overall. He delves into what to expect. In general, there’s a lot of whooping and cheering… several F bombs. All the things you’d expect from this scene. I was glad that this part was holding true. Again, super entertaining.

This entire time Mr. McClure (Dave) is sitting on the floor off to the side. If you don’t know Dave McClure, he’s a total rock star in the startup community. Total rock star. He started 500 Startups five years ago. I’ve read a lot about him, but my most recent exposure to him was at Denver Startup Week. He was the keynote speaker and my uber-connected friend got me VIP access to go hear him talk. It was a great talk that involved lots of swagger and the aforementioned F bombs, but the key takeaway for me was his exuberant commitment to diversity within the startup world.

Of course, my favorite line of his talk was “invest in people with boobs.” That’s a new way to position it, but clearly that’s a torch I also carry. What I liked most about Dave as an outsider looking in was his zest for non-conformity. He seems to exude this brute, “I don’t give a F%ck” exterior.

Shortly after the intro chat, I found my way to the designated Cheddar Up desks, which were four Ikea desks smashed together amongst a sea of other Ikea desks. Perfectly sufficient.

My lodging for that week was mediocre. I was paying a bit more than I wanted, but I was at least wise enough to book something in advance. I’d been “homeless” in SF before and waiting until the last minute only leads to hacker houses (i.e., sadness and desperation). It was a 2.5 star hotel. Super tiny, cardboard-like bed with a cracker-box bathroom. But it was really close to Union Square, so the energy made up for its quirks.

With Day one under my belt…up next was a quick, 30-second pitch. That’s easy, right?

Image courtesy of Cheddar Up.


About the guest blogger: Nichole Montoya is co-founder and CEO of Cheddar Up, a website that makes collecting money easy (and fun). She has 15 years of experience helping to grow and build businesses. Prior to founding Cheddar Up, Nichole served as a marketing strategist for the past eight years, helping firms grow their brands and reinvent themselves. Cheddar Up was a Women 2.0 PITCH finalist at How To San Francisco.