I got myself the perfect Mother’s Day Gift

In honor of Mother’s Day, I was going to find an inspirational quote about aspirational parenting like I did last year.  But I kept tearing up and couldn’t choose just one.  There’s just something so emotional about reflecting on motherhood as we go into Mother’s Day, especially during this time of year when our children are nearing the end of school years and “graduating” too quickly into the next stage.  

I keep reminding myself not to lament the passing of these “longest shortest years” and embrace the growth and awe that comes with watching our children transform into people that challenge, inspire and teach us.  But it’s hard to hold and snuggle them and not wonder when will they start to resist this affection.

If I’ve learned anything from watching my stepdaughter become a tween and my guys transform from littles to bigs, it’s that each stage creates room for an entirely new level of bonding.  Baby massage and singing silly songs become wall climbing and debating which animal is smarter, monkeys or dolphins.

So I’ve decided this weekend is about that. It’s not about a gift or crafting the perfect day–my usual Mother’s Day dream.  This Sunday is going to be about creating intentional moments to bond with my children and my husband, in appreciation for giving me the very great privilege to carry the title “Mom.” I’m eliminating any anticipation of kids behaving at brunch or pampering me, and I’m just going to enjoy what’s happening.  The present I’m giving myself is presence. That’s all I want.

I hope you all have the same opportunities to slow down and connect.  But if your plans have you overly committed, don’t worry. We decided at Pearachute that the whole month of May should be dedicated to moms, so keep an eye out for lots of fun activities and community events on the platform…and of course some great offers and member appreciation days to make it that much easier to create those moments that matter.

Happy Mother’s Day to you all!




Today is shorter than most


My three and a half year old still sleeps with a pacifier.  I know it’s bad.  My husband knows it’s bad.  Our dentist said he would be fine…if we stopped when he was three.  We haven’t.  Part of it is certainly the fact that we just can’t seem to find the energy to fight the fight.  But the bigger, unspoken reality is that we both know it’s the last reminder that our last and youngest is no longer a baby.  

This morning Aedan fought very hard to bring his binkie in the car to school.  He kept saying over and over again, “I want to be a baby!  I not a big boy, I want to be a baby!”  I know this is common and the mom in me that desires to empower him on his journey through life put my foot down and said “No.”  

But the mom in me that aches for all of those parents in Parkland, Florida wanted to say “Yes, please stay a baby,” wanted to wrap him in a blanket, stay home from school and cuddle him until he begged me to stop.  

I didn’t.  But as I drove to him to school and myself to work, I let muscle memory guide me and allowed my mind be present, let my heart hurt, let tears roll down my freshly made up cheeks. I created room to appreciate my children where they are in their development and spirit, and I prayed for the families suffering and even more for the safety of our children.

There’s a new saying going around the parenting world These are the longest, shortest years of our lives. It’s perfect.  It succinctly sums up all of the great but hard parts of parenthood and reminds us of the importance of presence on this very short in time, very long in learning years period in our lives.   

I wish it hadn’t taken a tragedy to wake me up this morning.  I wish that I could find intention every day to be grateful and present with our children.  But for now, I will find my silver lining in this and move forward today with appreciation of just how short this time is.

The Hottest Thing in 30-Something Dating


“So, do you come here often?” I asked awkwardly.  Oddly, I don’t ever think I used that line in my twenties I thought to myself.  He answered an enthusiastic “Yes! Every week for about 6 months now.”  We were sitting just a couple of seats apart.  He was about my age maybe a little younger, fit, tall, well-dressed.  

“Um, would it be weird if I ask you for your wife’s number?” I followed.

“Not all!” He chimed.

We both whip out our phones, and I text something along the lines of, “Hi Meg, this is Desiree! Chloe and my son Griffin really hit it off in Brazilian Jiu Jitsu, and your husband gave me your number so we could coordinate a playdate.  Hope to meet you soon!”

I never got a text back.  Maybe I heard the number wrong. Maybe not.   

Family dating is rough.  Not only do you need each parent to be cool, but your kids need to be within 6 months of each other and ideally of the same sex.  If you have two or three kids, then all the kids need to be relatively close in age.  

It’s hard to find your perfect group.   

Admittedly, I’ve been lucky.  My oldest son got invited to a birthday party for a child he barely overlapped with in his new daycare room.  We ended up meeting two friends with boys the exact same ages as my boys, and we’ve been hanging out at least quarterly ever since.  But the three years before that birthday were pretty lonely as parents.

Having spent years focusing on my first startup, I didn’t cultivate a lot of new friendships. Not being from Chicago, I didn’t have a built in group of high school friends.  So when we had Griffin in December of 2011, I had no idea where to find new mom friends.  I remember going to the park that spring and looking longingly at a group of moms with older kids, wondering “When will I find my crew?”

I decided, I’d have to build my own. So I literally started just walking up to random Roscoe Village moms with babies about Griffin’s age (that were clearly out for a walk and some fake social engagement in the form of barista banter) and invited them to the park with me.  One time, we literally picked up 6 women en route.  A few of the friendships stuck and we planned a playdate here and there.

But the process was clunky and awkward.  Text exchanges would be miles long as we tried to figure out dates that work, nap schedules, food allergies, comfort level with dogs (and dog hair), and when husbands would or would not be there.  In the end it would often be easier just to meet at the park…until September.  Then we were out of luck.  

This challenge, shared by families all over (but especially in our office of parents), is why we have expanded our vision for Pearachute.  

When we initially launched the platform in early 2016, we started with a “ClassPass for Kids” concept, hoping to make it easy for the parents of babies and toddlers to discover and book great activities in their cities.  We always knew we would grow with our members, introducing new activities and classes as the children aged up.  But what we didn’t anticipate is how much the world would expand when we started to look at the much broader category of family entertainment.

From theme parks to movies to concerts, American families spend about $70B each year on entertainment and hobbies.  This is exclusive of the $30B they spend on their kids’ sports and enrichment programs. And it’s only getting bigger.  

The simple truth is that Millennial parents are busier than previous generations (more dual working parents than ever before), and we want to spend more meaningful time with our children.  We have 27 hours each weekend to play, learn, enrich, and snuggle with our kiddos, and we care more about investing in that time than buying a home.  

We spend 50% more time with our kids than their grandparents did, and we’re looking for meaningful activities to create lasting memories.  

But we’re also inspiring an entirely new chapter of social engagement.  Our Alpha generation kids will be the most photographed and shared generation yet.  They’ll have a social media history often older than they are (thanks to all those ultrasound pics).  

And while nearly all have tablets, few will have phones before the recommended age of 11-13, leaving millions of children with a strong social desire to connect with their friends dependent on their parents for coordinating those activities.  

That’s really where we see massive opportunity for Pearachute.  Our new activity feed is step one in helping parents quickly and easily see what their friends’ children are doing after school and this weekend, so they can effortlessly join them without tons of back and forth text messages or coordinating who will host or pay for the activity.  

Pearachute Activity Feed

With a couple of clicks, parents notify each other that their kids are joining in on the fun, turning a 45 minute taekwondo class into an impromptu playdate you can book the day of.

We know this won’t fix things overnight for lonely new parents.  But we do believe that over the next few years, when people ask parents how they met their new family besties, an enthusiast “Pearachute!” will be a popular refrain…very different than the sheepish “Tinder” we give when talking about our spouses.

August!? Am I right?

The longer I’m a parent, the more I realize that August is just hard. There’s no other word for it.  Day camps end, your nanny goes back to teaching, your summer bucket list looms over you, school supplies, tuition is due, last chance beach weekends get planned, and work doesn’t stop.  It all adds up to a lot of stress and a lot of money.  It’s more expensive than December for a lot of families and much less of a reward, as your children don’t exactly light up when you buy them 5 glue sticks, two kinds of crayola markers and 50 large white plates.

It doesn’t matter if you live paycheck to paycheck or are swimming in cash, August is hard, and it’s only getting harder.  According to the National Retail Federation back to school spending will reach $83.6B this year in the U.S. up from $75.8B last year.  The average family will spend $688 to get their kids ready for school.  What’s more shocking is that number doesn’t include what families will spend on enrichment.  It’s just the average cost for school supplies, clothing, shoes, and electronics.  

Last year’s Backpack Index showed that parents expected to spend an average of $739 for the school year in school related extracurricular activities per child.  That’s an average of $82 per month before you include additional activities like swimming lessons, tutoring and other hobbies.  And when are most of those checks due?  August and early September. This cost is only going up, growing by as much as 10% a year for our oldest children.  

While some could say this is a product of us overcommitting our children, I think the reality is that this number will naturally increase over time as millennial parents continue to emphasize experiences over things.  

The question we face at Pearachute and one that we want to share with our partners is how can we make this more affordable?  How can we make sure that the August $500 annual fee for an activity doesn’t exclude a portion of the population that is already spending well over $1,000 to prepare for the year?

At the risk of sharing too much about our family finances, I’m feeling this pain too.  As a second-time founder of a startup, married to a police officer, and not coming from a wealthy family, August is rough, even with Pearachute.  My oldest is ready for league sports (checks due this month), my youngest has tuition due (August 15), we have to pay for daycare all month, and I have to travel for work (more babysitting because of John’s irregular schedule).

Knowing this, Pearachute is trying to get creative in how we can help our families navigate this month and the Fall in general.  Here’s what we’re doing.

If you have other ideas, we’d love to hear them!

In this with you,

Desiree & The Pearachute Team


The loneliest family holiday

For years, the 4th of July was one of my favorite holidays.  My childhood 4ths were filled with memories of beach trips to the grandparents, boating with cousins, and running around open fields of blankets and coolers with new little friends. Teenage 4ths were about friends and flirting and sneaking Zimas.  And in my early 20’s it was backyard BBQs and grown boys launching street fireworks.  

But something changes when you’re new to a city, the first of your friends to have a baby, or the last of your friends to get married.  Suddenly this very social, universal day of sun and cheer becomes something else…it becomes kind of lonely. 

My first taste of this was the summer of 2008.  I’d recently moved out of my ex’s house and realized that one year into living in Chicago my only friends were from high school in KC and a couple of other Yalies scattered in the city.  I was waiting tables at the time, trying to build GiveForward, and I got the day off because I’d assumed I’d have plans…I’d never not had plans in my 26 years of 4th of Julys.  

That morning I called my mom, feeling sorry for myself.  I’d been putting all of my time and energy into rebuilding my life post breakup and trying to start a company with no money that I hadn’t invested in friendships.  She listened and then said, “You know what you should do?” (her most famous sentence :), “You should call that sweet girl Sharon from Yale and ask her what she’s doing!” I groaned back at her about how lame that would be, since we weren’t super close. 

But a couple of hours later, I did call Sharon  who was generous and caring and invited me to join her for an amazing day.  She brought me to multiple parties including my first roof deck fireworks, and ultimately she wing manned that night as I met my future husband.  

Fast forward four years, and I found myself in a similar situation.  Being married to a police officer in Chicago means you never get your husband on the 4th.  The fireworks apparently bring out the desire to shoot, handgun violence explodes in the city, and no one gets the night off. The previous years I’d worked.  But the 4th of July 2012 was my first as a mom. Griffin was just 7 months old and a very challenging sleeper.  I had no friends with kids, so I had no idea what to do that day except pray that the fireworks wouldn’t keep him up too late. 

The next years were better, sort of. We had people over during the day, and the year after my sister had a party.  But both times Finn was the only kid, and I was still alone at 8 o’clock listening to fireworks from the couch as he slept. 

Last year (aka year five of being a mom), we had our best 4th yet. I was in KC with my friend Lindsay and our kids, watching fireworks over the lake and adventuring through 11pm bedtimes.  I remember having a moment on the boat as my kids splashed and laughed thinking “this is what the 4th of July is supposed to be.”

This year, we’ll be in Chicago, and we have no plans.  A spark of panic hit me last weekend as I realized that this year wouldn’t compare to last.  I decided to put myself out there again and asked my most social friend Cindu what she’s doing, with the hopes of tagging along and at the risk of feeling like I was inviting my family to some intimate gathering.  Surprisingly, her family was in the same boat with no plans. 

What this tells me is this is two things.  First, there are some years when holidays just don’t live up to what we imagine (ahem Mother’s Day am I right?), and we just have to cherish the good ones that much more. 

But more importantly, I’m reminded that so many of us are alone for different reasons during holidays.  If we’re willing to be vulnerable and share that, people will gladly invite us to join them.  

And if we do have plans, we all have that new friend who just moved here, or just had a baby, or just got divorced who might be feeling a little lost this 4th.  I hope you’ll reach out to them and check in.

Because you never know what might happen…you might just meet your future partner or next best friend.  

Why Men (and Women) Bail on Female Founders

I started to write this post last Fall and didn’t because I was worried how my peers would respond in a post-non-Hillary world. But on International Women’s Day, I’m going to take a chance…

Recently, I was at the First Round CEO Summit talking to an amazing group of female founders.  I joined the group as they were discussing a vc who backed out of a term sheet.  We all gasped a little inside.  We know it happens, but deep down you hope that in your next round, you’ll saddle up with investors who would never do that.  And we all wondered aloud, if this happens more to female founders than to our male counterparts.  
The conversation turned to talking about a certain woman vc who is notorious for abandoning her companies at the first sign of difficulty.  I don’t know her personally, but I started to defend her.  

My argument was that there are so few women involved in big deals and there’s so much internal and external pressure for them to perform that they’re likely uncomfortable spending too much time on a company that might reflect poorly on the vc in a Monday morning partner meeting. 

We all agreed we wouldn’t want her as an investor.  

But having had a few months to reflect, I’m realizing how fundamentally flawed this whole system is.  And when you break down why people don’t back or bail on female founders, I think it all stems from this miserable intersection of fear of failure and the subconscious need to be right…even when right means “I knew I couldn’t do it.”

At one point when I was running GiveForward, I got into an argument with a senior team member.  In front of a room of people, we disagreed about something and he “reminded” me that he was “in charge of growing this company.” I asserted loudly enough for everyone to hear that he was wrong.  As CEO, I was responsible for growing this business.  

That moment was a turning point for me in a lot of ways.  It was the first time my team saw my frustration at what was a growing problem on the senior team.  But it was also a loud announcement of my fear that our failure to hit numbers was an indictment on my ability to lead the company…and deep down that evil imposter syndrome reared its ugly head.

What followed was a tailspin of self doubt.  I questioned myself as a founder and as a leader.  And thanks to a call to my board by said senior team member, my board now questioned me too. Ultimately we decided to look for a new CEO.  

But to be perfectly honest, that wasn’t the part I’m embarrassed or ashamed of. What happened inside my head was the most embarrassing part.  I’ve always considered myself an early supporter of women founders, but the reality was that there was an internal monologue that sounded nothing like support.  It went something like this:

You knew you couldn’t really do this. They knew you couldn’t do this. This was always going to be the way it worked out. Very few women get to take a company as far as you have. You should be grateful. Now maybe you can spend more time with Griffin and John…or have another baby?  You’re just a better starter than executer.  That’s okay. You’ll probably love running strategy and biz dev. You are lucky you got this far. Just don’t lose your company.  Play along.  What are you if you’re not the CEO of GiveForward? Founder is good enough. Isn’t it?”

I wish I could shake that person and scream at her “You’re wrong!” Everything about that message was flawed because every piece of it was filled with self doubt and convincing myself that I was right all along…that few women can build massive companies. 

Because that’s all we’ve known as women…especially in Chicago.  There are so few of us that have actually started and carried a business to scale.  And the brain likes pattern recognition.  If there’s no pattern of women killing it, how do we know we can? 

It’s like the 4-minute mile.  No one thought it was possible until someone did it…and since hundreds of people have done it. 

Women need our 4-minute mile successes–ones not led by celebrities. We need to turn off the subconscious bias that rings in the minds of both male and female board members that says we are less likely to succeed. 

Performance is what’s going to change this system…that and more women in the room.  It’s not protesting or taking today off work, although those actions are powerful for separate reasons.  It’s performance. Killing it at our jobs, finding new and better opportunities that only we can see, and supporting each other on the journey up. 

Feel free to disagree, but I believe that the day we IPO our own companies and fill our own teams with women leaders is the day that we will see equality.

And for what it’s worth, I didn’t tell the group of women founders that day that I had just had a firm back out of a term sheet–that a name brand investor with an all male team gave me terrible terms that I accepted for the wrong reasons. They talked down to me, called me diminutive names like sweetheart, and ultimately passed because our 160 day old company hadn’t hit explosive growth. At the time I was embarrassed it happened.  

But time (and hitting numbers) gives you so much perspective.  I realize now that the only disappointment I should feel is that I ever considered the deal in the first place. Lessons like that aren’t a sign that I can’t do this…they’re a sign that I’m learning…like every male founder is too.

And I’m so glad they passed. It made room for the valuable male and female investors who truly believe in me and this business.  
Thank you: 

Sam Yagan, Paul Lee, David Cohen, Stuart Larkins, Ezra Galston, Kevin Willer, Matt McCall, Guy Turner, Stopher Bartol, Russ Fradin, Genevieve Thiers, Cyan Banister, Brittany Graunke, Sam Shank, Ethan Austin, Chrissie Pariso, Joe Roos, Justin Alden, Tord Alden, Heather and Sean Harper, the leaders at FireStarter, and everyone who has invested through our Republic campaign. And of course, thank you to my husband, my biggest “investor.”

Mac & Cheese recipe

Because people have asked, I figured I’d share the recipe from the Mac & Cheese recipe that won last weekend 🙂

It was inspired by this one:

1 lb thick cut bacon

1 1b box medium shells

1 stick of butter

1/2 teaspoon of salt

1/2 cup flour

1/4 teaspoon nutmeg

1/4 teaspoon cayenne pepper

3  1/2 cups milk

1 egg

8 oz cream cheese

1/2 lb American cheese

1 1/2 cups sharp cheddar

1/2 cup pepper jack

1/2 cup shredded Parmesan

Panko breadcrumbs


Preheat oven to 350.

Chop and cook bacon into crumbles.

Boil pasta in salted water, drain and set aside in a large bowl to cool.

In a large pot, whisk butter, flour, salt, cayenne, and nutmeg until smooth.

Add milk and bring to a boil.  Stir in cubed cream cheese and then the other cheeses.  Remove from heat.

Stir beaten egg into the cooled noodles.  Then pour cheese sauce over the noodles, stir in bacon, and place in greased 9×13 inch pan.  There will be a lot of sauce.

Cook 30 minutes and then add seasoned panko breadcrumbs to the top for 15 more minutes.

This recipe is awesome because it stays creamy hours after you remove it from the oven.