How one founder handled the logistical challenges of leaving her family and team for four months. 

By Nichole Montoya (Co-founder & CEO, Cheddar Up)

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

How does a mom of eight and nine-year-old daughters head off to San Francisco for four months? Not easily. But with the decision already made, the next obstacle was determining how to make this happen without alienating both my family and sanity.

When an opportunity like 500 Startups comes up, a lot of entrepreneurs, and tech companies in particular, often entertain the idea of moving to SF full-time. For the Cheddar Up team, that just isn’t an option. Most of us have children and spouses. And all of us love Denver and all the perks that come with living in beautiful Colorado. And as the CEO of Cheddar Up, I see clear advantages to not being in the Silicon Valley bubble full-time.

Knowing this was a temporary arrangement, a lot of people and parts went into making 500 Startups possible for Cheddar Up…let me explain.


Being a startup founder and a mother is nearly impossible without a really supportive husband or partner – someone to share the load and who understands when you’re working 12-15 hours days nonstop. My husband has already been dealing with this quite gracefully for more than 12 months, but now instead of covering me on the 12-15 hour days, I was relying on him (and some babysitters) to essentially cover me 24 hours – multiple days in a row.

Let’s just say that I continue to rack up a lot of IOUs – and I’m not talking about the Cheddar Up kind…

Get Real

Parker ThompsonI already mentioned in my first blog how the 500 Startups offer came with a great deal of flexibility. From the very first conversation I had with Parker at 500, it was clear they were realistic and supportive of women founders. I forget the exact wording, but Parker said something along the lines of, “We could definitely work something out. We want you to be successful and to get the benefits out of the program, but we also don’t want you to be miserable by being away for four months straight.” Super real. Super supportive.

I’ve learned the hard way throughout my career — and more so recently with Cheddar Up — to trust my gut. Whenever I’ve had a hunch that someone may be inauthentic but have proceeded into a business relationship with them anyway on blind faith, it backfires.

And the same goes for the reverse. Parker and Co. fall into the “authentic” category. Maybe it’s my Iowa roots, which have proven unshakable, but to me, authenticity = goodness. And you can’t go wrong with that at the core. It’s a rare thing in this odd startup / accelerator land. Very odd. And I feel fortunate to have found it.

Boots on the Ground

Knowing that I couldn’t be in San Francisco full-time, I wanted the next best thing. One of my teammates there full-time to carry the flag, to be present for serendipitous events, to do the beer drinking on my behalf, etc. And fortunately, I had the perfect teammate who was up for the task.

500 Startups is like a fraternity for dreamers and doers, only better. You get to work out of a sweet office in the heart of San Francisco with likeminded, crazy hard-working individuals who are just as passionate about their startup as we are ours. The energy is contagious! What founder wouldn’t want to take part?

Alex ShortleWith that in mind, you can imagine that it was an easy sell for my single, childless teammate – Alex Shortle. And when I say “perfect” teammate for the task, I mean it. The guy started a fraternity in college. He worked on a ranch. He can tie a jib and sailed a potential investor around the SF Bay the first week he was there after leading a Korean startup team in beer pong. For reals.

He was not to replace my role at 500 in any way. But he’s definitely integral to our participation, especially over the few weeks I was heads down on product with the rest of the team and preparing for our big SXSW pitch on March 16.

Not to be forgotten are the other members of my team — the ones holding down the fort in Denver when I’m in San Fran — working autonomously, getting $hit done in my absence, respecting and fully understanding why we’re enduring the craziness of all the back and forth.

Crying is Healthy, Right?

Finally, the other major factor in making this program possible is the support we receive from our friends and family. Whether it’s an ear they lend during one of my monthly mental health breakdowns, or a landing pad for our kids when my husband and I are both traveling, we couldn’t do it without them. With all that in place, let’s get this show on the road.

This post originally appeared on the Cheddar Up blog.