Hackers, Hoodies, Daycare: One Mom’s Decision to Join 500 Startups

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Starts with an F, ends with a K…

By Nichole Montoya, Co-founder and CEO of Cheddar Up This is part two in a series from one of our PITCH finalists documenting behind-the-scenes life at her growing startup Cheddar Up. Here’s part one.

Some people say the bigger deal you make out of being “different” the more polarizing it can be.

I tend to agree. But I’m so different from the folks I’m hanging with right now that it’s simply entertaining. For one, I use the word “folks.” And honestly, I don’t see any way around documenting this experience.

Thus, this is the first of many posts that will provide a small window into one mom entrepreneur’s experience at 500 Startups. We’ll call the series “Mama Needs a Hoodie” – for obvious reasons.

A Little Background

If you haven’t been following Cheddar Up’s journey, here’s some background. My co-founder and I founded Cheddar Up two years ago. We’re both moms. We each have two children ages seven and nine (+/-). Prior to Cheddar Up, we were a marketing and designer powerhouse. I played the marketing director role and I’d swoop Molly in to make us all look good with her brand and design prowess.

This, of course, was prior to realizing that the world needed a better way to collect money from groups – particularly schools and moms. We launched Cheddar Up a little over a year ago and it’s been both good and difficult with the good solidly in the lead.

We’ve been in the media, we’ve been selected to pitch at high-profile events, we got funded (led by one of the best VCs in the country), we’ve earned the trust of our beloved users (!), and most recently, we were offered a spot in one of the most respected accelerators in the world – 500 Startups.

Not familiar with accelerators? Let me explain, because this is important. An accelerator is a program — usually three to four months in length — that provides resources and expertise in an effort to make a startup more likely to succeed. It usually comes with an investment. There are hundreds of accelerators around the world. Most of them are not worth their salt.

500 – Kind of a Big Deal

500 Startups500 Startups is known throughout the global startup community and comes with a healthy investment: $100,000. That’s a lot of money. But in my opinion, the best part is its network.

Being involved in 500 Startups puts your startup on the map and gives you access to hundreds of seriously accomplished entrepreneurs and investors. When I first started Cheddar Up two years ago, I looked at 500 Startups with big, admiring eyes. Then, it seemed out of reach.

Starts with an F, Ends with a K

This is in part why being invited to 500 Startups was bittersweet. The timing? Amazing and horrible at the same time. Here you need some history.

This past fall I did an accelerator program in Silicon Valley. I won’t go into specifics, but it definitely wasn’t 500 Startups caliber. It did, however, get me to the valley where I made some great connections (That entire experience is worthy of a separate blog series. I was, for example, basically homeless for a week – bouncing from hotel room to hacker house – and I can safely say that I hit rock bottom wheeling a suitcase across the interstate. I digress.)

My point is that I just finished spending three long months away from my husband, away from my beautiful little girls and away from my team. And now it seemed I was considering doing it all over again. The thought almost sent me into a downward spiral.

We had been talking to 500 for a few months about a potential investment outside of the program. So when the 500 offer landed in my inbox one Friday afternoon while sitting in carpool, you’ll understand why instead of sheer excitement, I sent a one-word email to my entire team that started with an F and ended in a K.

As the CEO of Cheddar Up, the decision of whether or not to accept the 500 offer fell on my shoulders. While it meant giving up some equity and spending four months in San Francisco, I couldn’t deny that from a business perspective, the timing couldn’t have been better. Having raised some capital, we were finally in a position to spend some money on marketing. This is one of 500’s areas of expertise: digital marketing. “Distribution” as they call it. Helping startups become masters at growing their user base.

Fortunately, I have a crazy supportive husband who knew I couldn’t turn it down. My kids on the other hand… they weren’t so keen. But that’s another post. I’ll have a 10-gallon side of mommy guilt, please.

Then of course, there was my team to consider. Aside from Molly and me, the Cheddar Up team includes two Alexes – one 26 and one 30. The doors that 500 would open for them, both now and down the road in their careers was undeniable. All of these factors combined, the writing was on the wall. When 500 confirmed there was some flexibility in the schedule, the decision was made.

We received the offer email on January 9th; the program started on January 20th. Mama not only needed a hoodie, she also needed a flight…

This post originally appeared on the Cheddar Up blog.

Join us at 500 Startups for our next San Francisco City Meetup - Thursday, May 7th.


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.