The Startup Family

Two years ago I was in my late 20s and I had begun acquiring the trappings of a family man; I had a house in the suburbs, a kid, a pregnant wife and a good job at a big company. Yet I had also begun asking myself difficult questions about my career, my future and if it was too late to do something a little crazy. Somehow I had let the Earth go around the Sun one too many times without fully expending my own potential energy.

“Do dads work at startups?” I asked my wife one evening. “Like young dads, dads with babies, is that a thing?”

If you have ever nonchalantly asked your pregnant wife a simple question with vast, earth-shattering implications for you and your family’s future you may have some idea how this conversation played out.

My own internal musings had unwittingly unearthed themselves in the form of an innocent, somewhat glib question that hung in the air long enough for me to recognize the impending swell of chaos and pain that I had unleashed upon my reality.

Someday, when I die, I hope that it is either swift and oblivious or gentle and prepared. I have stared down the tempest and the worst part is the waiting.

I had a job offer, an offer that I had immediately dismissed, just an errant email sitting in my inbox. Working as a Software Engineer at said big company means that these recruitment emails are an everyday occurrence. They are something that you delete without reading and then attempt to remind yourself to disable those LinkedIn notifications. This one was different though, it sat in my inbox for days and I re-read it constantly, attempting to decipher a future that I could be confident in, that I wouldn’t regret.

Then the questions came in, my wife had a lot of questions and many of them I had obviously thought of, but many of them were so incredibly specific and detailed that I was desperately attempting to take mental notes while portraying a sense of bravado and confidence. My wife is an ex-kindergarten teacher and sometimes I feel bad for those kids. You think you’re going to go to school to throw rocks and scribble on paper but instead you will be reading Shakespeare before you learn how to open your own damn milk carton.

If not Shakespeare then at least Dr. Seuss.

Health Insurance, Salary, Location, and the dreaded Work/Life Balance question were the big ones, well, the big, practical, tangible questions, at least. Suddenly this incomprehensible reality started becoming real. The more steps I took to getting these questions answered the closer I came to imagining it actually happening. At first it was a few exchanged emails, then some phone calls, a lunch visit, an interview, a job offer, I even tried to change my mind at the last minute, a fact that my CEO still remembers and one that I’ll never live down.

My wife was actually incredibly supportive, we came up with some basic requirements that our family needed for its continued harmonious existence and the rest is in the details.

Speaking of the details, from start to finish it took about three months of conversations for my basic requirements to be met. I joined Cratejoy the week after the Series A round closed in August of 2014 and I cancelled a myriad of doctor appointments for three weeks until Cratejoy could give me health insurance. I personally go to the doctor about once every three years but babies and soon to be born babies are the backbone of the healthcare economy.

Quitting my job was hard. I have quit jobs before but this time was different. I was doing well at this job, fast-tracked for big things and also generally content at what I was doing. It’s much easier to quit a job for something else that is obviously a step up, an improvement.

“Where are you going?” Is the immediate question that everyone asks.

I learned that when I answer with,

“Cratejoy, it’s a startup, I’ll be the ninth employee.”

I was really challenging my colleagues with an idea that they had long ago dismissed as absurd. I was defying conventional wisdom, I was leaving a sure thing to be back begging for my job in another three months. This is true for friends and family too, answering this question became a litany of describing how crazy I probably am and how aware I am that I have a family now.

It’s like the more questions I answered the more confident other people were that this was a bad idea.

“Yes I’ll be working out of a house, I think it used to be a frat house.”

“Yes I know, I expect it will be hard.”

“No I’m not working for free.”

The risks are real and tangible. I know the math, I know that 90% of startups fail and that founders don’t start companies expecting to fail, even a sure thing is unlikely to exceed your own hopes and ambitions. But I have always admired and respected the people who try rather than the people who can confidently state why trying is a bad idea.

Looking back the house had the strongest psychological effect on me. Going to work everyday meant parking in a neighborhood and carrying my laptop bag up to a house that I disappeared into for the day. I had a little desk in a corner of what was supposed to be a bedroom and the bathroom situation felt awkward. It wasn’t long before we outgrew the house and we finally moved into a “real” office. I realized after we moved that I had actually grown to like the house. There was kind of a romantic idealism about the house. I was very far off the beaten path and I felt like I was playing a vital role in turning this crazy idea into a reality.

Two things have been absolutely required since the beginning of this journey, extreme transparency and communication. If you are looking to hire a guy that can live and breathe your startup for 12 hours a day every day, I’m not that guy. I can do that and I have done it when the need arises but at the end of the day I’m not employed by just one startup. When my work day is done I have a 45 minute commute home which is actually vital decompression time and then I’m clocking in at my second startup, my family.

So here we are almost two years later, the journey so far has been both rewarding and challenging. I have worked hard and I have seen the rewards of that labor. No matter the outcome of this venture I have grown as a human and leader. This is the future I was hoping to decipher.


Oh, and baby number three is on the way.


Me: You know how I hate coming up with resolutions at the beginning of the new year?

Tina: Yeah..

Me: Well I’ve been thinking about it and I think I’m going to have a few for 2015.

Tina: Oh? Like what? (She is noticeably perkier, Tina loves New Year’s resolutions)

Me: Well you know how the doctor gave me that extra strength shampoo for the bumps on my head underneath my hair?

Tina: Yes it smells bad, everything about you is disgusting sometimes. (I interpreted part of this from the way she stopped eating her food abruptly)

Me: Well the shampoo only mostly works so I think I’m going to see a dermatologist this year. Doctor Boyd said that if it doesn’t get better I should..

Tina: Don’t you need to get a physical too? When is the last time you went?

Me: That’s.. No. The point is I vow to go to a dermatologist this year.

Tina: Yes and go to the doctor.

Me: No! No doctor, I don’t need the doctor, this is MY list. You go make your own.

Tina: I did, and I put making you go to the doctor on it.

Me: That’s not, that’s not how it works you can’t put stuff for me on your New Year’s resolutions!

Me: Anyways, I’m also going to get my suit jackets tailored, they already did the pants which is the hard part so I think I will get the jackets done, the arms fit a little weird.

Tina: These aren’t resolutions, this is like a chore list. You could do all of these things in one day.

Me: What? No, this is hard for me. I haven’t been to the dentist in 2 years because I don’t like it.

Tina: Uhuh, yeah you need to go to the dentist.

Me: No! 2 years ago one of my resolutions was to get my wisdom teeth out and look what happened! (I may have stuck my tongue out here)

Me: Now I have permanent numbness on part of my tongue and I’m even more terrified of the dentist!

Tina: You are ridiculous, resolutions are things that you are supposed to try and do the whole year to make you a better person, like exercising.

Tina: I mean usually I don’t get past the second week.

Me: I also need to get my car door fixed from when I hit that column.

Me: That’s it, those are my 3 New Year’s resolutions.

Tina: You know what is going to be more depressing? When you don’t even get those 3 things done in an entire year.

Build Your Own Patio: A 12 Step Guide


Step 1: Tell Your Friends

Recently my wife and I decided to expand our measly 10×10 back patio to a 40×10 Patio Extravaganza! While the wife was going through the process of getting bids from different contractors I had a few friends over to drink beer and talk about said patio.

“They are quoting like 3000 or 5000 dollars!” I said vehemently to said friends.

“Why don’t we hire the last guy, who will do it for 1500 dollars?” my wife said accusatorily. (not a word? should be.)

“Hell man, I could salsa dance half way around the world with 1500 dollars!” said Bebop, swaying his hips mesmerizingly. By the way my friends are named Bebop and Rocksteady in this recounting.

“Why don’t we just do it? It will be a piece of cake man.” said Rocksteady confidently, as he finished off another beer.


 Step 2: Convince Your Wife That You Can Do It

So after a few days of deliberation and a couple of youtube videos, I started to think, yeah this doesn’t seem so bad. It’s like baking a cake! Is what I was thinking at the time. As the days went by and the wife got closer and closer to calling back the lowest bidder I finally broke.

“Stop!” I yelled by myself in an empty room for no particular reason.

I explained in great detail to the wife exactly how it would be so much better if Bebop, Rocksteady and myself were to complete this project instead. I did some quick math and decided that I could basically do this thing for under 1000 dollars and then we would have 500 dollars for shopping! (not really.)

The wife was not buying it, but after some continued persistence I guaranteed her that there was no possible way this could end poorly.

Here is a picture of us being happy together. (It’s from a long time ago)


Let’s really hold on to the moment in the picture and cherish it. We are going to need it.


Step 3: Wake Up Early and Rent a Bobcat

“I’ll be there at 5:30 tomorrow morning.” said Rocksteady.

I had just finished telling him that it was go time.

“It’s go time.” I had said earlier.

“Oh dude. I can’t make it, are we really doing this?” said Bebop as I had called him after calling Rocksteady.



One thing to note, anytime that you have to get large things into your backyard, the only way to do it is to take down part of your fence, which sucks.

Rocksteady proved to be an excellent Bobcat driver as he had previous experience and soon the backyard was looking like a dirty, muddy mess!



Also, look at how cute! My dogs liked to ride in the Bobcat with their new best friend, Rocksteady!


Step 4: Put Some Dirt Back Holmes

Man, Rocksteady and I sure did a good job of leveling out the backyard. We did such a good job that when we went to measure how deep the patio was going to be we realized that we had leveled it off at about a foot deep! I thought this sounded pretty good but Rocksteady didn’t think so. Apparently a foot is a lot of concrete, like a LOT of concrete.

“We really want the patio to be about 4 to 6 inches deep at most.” said Rocksteady.

Pouring a foot of concrete for around 300 square feet would cost 2 or 3 thousand dollars just for concrete, I later found out. Oh also, we already returned the Bobcat, because it’s the next day now.

To make this part of the story shorter I spent the next weekend buying dirt and rocks and filling the patio back in.


Step 5: Schedule the Cement Truck Before You are Ready

Finally, it was seriously time to pour some concrete. So I called the place and scheduled a truck to come out on a Tuesday.



But wait! We are not ready for the truck yet!


Step 6: Keep Putting Dirt Back Until 2 AM!

The night before the truck was to arrive I realized that I still had not quite filled in the patio up to 6 inches, and with only 8 1/2 yards of concrete coming some quick math said that I was in trouble. Luckily Bebop was staying the night because I didn’t trust him to actually arrive at 6 the next morning.

Would you trust this man?

So Bebop and I purchased more rocks and dirt and filled in the rest of the patio until about 2 in the morning.


Step 7: Set the Forms!

6 AM came very quickly the next day, actually 4 hours after we finished the dirt to be exact, and with it came Rocksteady. The concrete truck was showing up at 1 pm so we had all morning to do things. And man did we have things to do.


Crap, that’s not good enough. I feel like some concrete might escape…



Oh also, holy crap! Put some rebar or something and yeah, probably drill and epoxy it into the existing foundation! Science!


Step 8: Compact That Shit!

Wait crap, did we do the rebar? No don’t do that yet. First, COMPACT THAT SHIT!




Step 9: Freak Out! (On The Inside)

There comes a point in time when you are on the cusp of doing something great where you think that you may have made a grave mistake. I don’t know the first thing about pouring concrete, this could turn into a very expensive, very heavy pile of sharp pointy rocks.

Dispell these thoughts! These thoughts are the difference between being awesome and having a healthy view of your own limitations.


 Too late! The truck is here!


Step 10: Admire How Stalwart Your Friends Are

One of the most terrible feelings in the world is watching someone else’s face as they slowly realize that they need to extricate from a looming, dire mishap in the nicest, quickest way possible. Such was the face of the cement truck driver as his confident swagger slowly turned into a hesitant retreat as he asked questions like, “Is this your first time pouring concrete?” and “Are you sure you are ready for this?”

“We’ll be fine.” I lied to him and myself.

“Let’s go!” said Rocksteady. I’m still not sure how he was able to be so confident by this point.

“Let me get my camera!” yelled Bebop as he trotted past a bewildered cement truck driver.

8Pro Tip: Maybe spend some time researching and acquiring the tools that professionals use before you result to, hey let’s use this 2×4 for everything!

This wasn’t so bad though, my shoes aren’t even getting dirty.

2After a while though, this gets exhausting. In retrospect, I should have realized that having 8 and a half tons of concrete delivered to my house means that I will be pushing and moving a literal elephant amount of concrete using primarily sticks and measly, pasty inside-y arms.

Also, we should totally measure concrete in elephants.


Step 11: Listen To Your Wife Tell You “I Told You So”


“Damn”, I was thinking at the time. “That looks pro as shit”. (Grammar thought: “Pro as shit” doesn’t make sense at all)

But if you look closely, you can already tell that water is starting to collect unevenly across the surface of the concrete and it is starting to slant down at the corner. You see, pouring concrete is more of an art form than it has any right to be, an unsteady hand (or an exhausted one) will create dips and uneven surfaces all over the place.

Also, you can’t tell from this picture but there is a pile of unfinished concrete drying on the other side of the existing patio in a lump and I’m about to lay down on the ground because the gravity of the situation is physically pulling me down.

Then, the dreaded question.

“Is it going to dry like that?” my wife, who had recused herself to the inside of the house, had sensed a lull in the chaos and emerged outside to rain down judgement and righteous wrath.

“It’s going to bake… like a cake.” I whispered from the safety of the unsettled dust, staring intently at the inside of my hat.

“What about this other side? It’s not done at all and where did the truck go?”

“It left. It emptied the rest of the concrete on the other side and it left.” I sighed.

For what it’s worth the driver lasted a lot longer than I expected him to.

“Is that enough concrete to finish the other side?”

She was so full of questions and thoughts and life.

“No. No it’s not.”

Step 12: Black Out

This one’s going into overtime. It was about 7 pm, the sun was starting to become beautiful and I was nursing a heat headache with beer.

The funny thing about concrete is, it is going to dry whether you want it to or not. You can run a water hose on it and try and move it around and it just marches forward, becoming a permanent fixture of your life.

Did I mention how stalwart my friends are? They are hurting, I can tell by the empty cans littered on the ground. Every second is key now.

I sent the wife to Home Depot to purchase 30 bags of concrete, we are going to be mixing in the last bit of concrete. We had already thrown every rock and piece of trash into the mix, to fill in some space.

Every inch of my body hurts and the playful banter and conversations had died away into silence. Even Bebop could not muster the energy to take pictures of this solemn scene. Hence no blog pictures 🙁

Finally, every last bag of concrete has been thrown into the mass and we smooth it out as it races to dry. It is 9:00 pm. My shoes, pants and hair have also solidified. I’m like the freaking Tin Man from the Wizard of Oz, except I’m concrete and have no heart.

Maybe it’s the beer, maybe it’s the heat but I’m done and the weight on my shoulders has been baked into the earth.


It’s been almost a year since I started this project and it’s been 8 months since I started this blog post. I kept coming back to finish it but I wanted to come full circle so here it is. The silver lining.

I hired a contractor to build the roof. While that went much better, that is a story to share some other time. Here’s the finished product.




And here is the patio in use at Owen’s first birthday party.


Total cost: $5500.00

Being Awesome: Priceless



Xbox One Support is the WORST THING EVER. PERIOD.


The following is a recounting of my experience with my Xbox One. All traces of emotion, screaming and profanities have been removed.

12/21/2013 – My Front Door
My Xbox One has arrived after weeks of weather delays. Thanks for nothing UPS.

12/22/2013 – My Living Room/Heart
I come home to discover that the Kinect on my Xbox is dead. Completely Dead. I look on the internet and yep, others have complained about faulty Kinects with the Xbox One. I look up the replacement policy and decide to put a credit card on file with Microsoft so they will ship me a new one before I ship my broken one back.

12/26/2013 – My Front Door (again)
My new and working Kinect arrives at my front door via Fedex. I now believe that Fedex is God’s gift to this green Earth and that UPS must be what Satan uses to send nasty singing telegrams to bad children.

12/29/2013 – Fedex Dropoff Location
I studiously drop off my broken kinect with the return shipping label at the closest fedex to my house. I do this so studiously because Microsoft warned me that if I fail to mail my broken Kinect back to them then they will charge me $160 real American dollars. Also, Fedex gives me a little bitty piece of paper with a tracking number on it, apparently people call these papers “receipts”.

12/29/2013 – But now later at my house
I put the “receipt” from Fedex on top of my nightstand after briefly considering throwing it away.

1/12/2014 – Digitally, in my email inbox
Many moons have gone by and I have successfully Just Danced at least 5 pounds of water weight off my athletic physique using my working Kinect. I receive a warning email from Microsoft that my account will soon be billed $160 real american dollars because they noticed that I absconded with both a working Kinect and an indubitably permanent broken Kinect.

1/12/2014 – On the phone
I am now anxiously on the phone, waiting to talk to Microsoft about the mistake they must have made. Why does everything happen to me? They talk to me on the phone. Apparently, my package never made it to 1000 Magical Microsoft Way and they don’t believe that I sent it at all. But wait, I have proof! A “receipt” you might even say. I can’t find it. Like, at all. My wife is now glowering at me as a try and make her believe that she must have the little piece of paper worth $160 real American dollars. (I promise, it’s really a thing!)

1/12/2014 – Many, MANY. hours later
I found the “receipt” it was on top of my nightstand where some idiot must have put it. Also, I called Fedex and I am most assuredly the first person to ever lose a tracking number on this planet. They were not helpful. I triumphantly call Xbox back and give them the special numbers on the magical piece of paper called a “receipt”. For the record, here is a link to my tracking number according to Fedex:

1/12/2014 – Still on the phone
I am told that my situation has been escalated and that I will most assuredly have my account notated that I am a most responsible gamer and not worthy of having $160 real American dollars deducted from my bank account.

1/21/2014 – Browsing my Wellsfargo bank account
I had $160 real American dollars deducted from my bank account.

1/21/2014 – On the phone, most voraciously
I inform Xbox that I have already settled this matter, why must they take my money anyway? I also look up my tracking number again, my package has been found and was delivered at 11:03 AM. My phone person also agrees that this is very clearly a mistake and should be fixed amazingly quick. The ticket was already escalated so surely things will be restored to what is right and just as soon as possible. Or in 6 to 8 business days. Whichever comes first.

1/25/2014 – In my car, On the phone
Broken, my wild stallion of a spirit looks for a comfortable place to die. I am on the phone. It hasn’t been 6 to 8 business days yet sir. 6 to 8 business days from when? I ask. From when the ticket was opened sir. Which was on the 12th, which was more than 8 business days ago? I inquire again. The escalation team is very busy sir, they should contact you within the next 4 days.

1/31/2014 – On the phone, or dead, I can’t tell
I demand to speak to a supervisor. I tell the supervisor all of these terrible things and they promise to help. To go above and beyond, finally some respite from the droning on and on of business days and escalation people. Someone who can GET. THINGS. DONE. As I talk to her I send spiteful messages to XboxSupport on twitter, my life has no meaning. She says she sent a special email and things will happen in the next 48 hours. Wait. So did she get things done or not?

2/3/2014 – One of the circles of Hell
Nothing. It has been over 48 hours and not a single email or money in my bank account.

So I must conclude, Xbox One Support is the WORST THING EVER.