Raising Rich Kids

How are you going to avoid raising shitty kids?

– A friend

In April 2019, I sold a majority stake in my startup to private equity. The news made local headlines and our family’s financial situation changed overnight. Soon afterwards I had celebratory drinks with a friend who is a serial entrepreneur and has sold multiple companies. He said to me, “Now that people know you have wealth, be ready for all of the awkward things they are going to say to you.”

Several months later I met up with a friend I used to work with. I don’t remember if these were literally the first words out of his mouth or not, but they very well could have been: “So… how are you going to avoid raising shitty kids?”

The path to having rich kids

Wow. That caught me off guard.

(And to that friend — if you are reading this — I know you’re going to feel bad and reach out with a flood of apologies. Don’t. Only a true friend would feel comfortable saying something THAT awkward right out the gate!)

It was a valid question that I didn’t have a solid answer for in the moment. And I sort of brushed it off.

I told him the same concern would have probably existed even if I never ventured out as an entrepreneur. My wife and I are incredibly blessed that our parents and grandparents put us on a trajectory to live a much more comfortable and luxurious life than they did. Had I stayed put as a software engineer, we would now be two decades deep earning dual-incomes while climbing the ladder at large technology companies. By all measures I’m sure we would be living an extraordinarily privileged life. When I imagine the potential lifestyle in that scenario, I have to wonder: how much less would we need to worry about our kids being spoiled if we simply lived in a 4,500 square foot house and drove less expensive Teslas?

But I suspect my friend was imagining some particularly dramatic changes in our lifestyle.

And to a degree, he was right; there are some substantial privileges our kids have encountered these past five years– even in comparison to the other very successful, high-income families all around us. The house we live in, the travel experiences, the way we dine… Varsha and I no longer hesitate on experiencing the “best of” when it comes to the things that truly matter to us, and our kids are usually right there by our side.

Our change in wealth has certainly impacted many of the “big” purchases and “big” experiences in our lives. But, in all of the “little” ways, I like to think that we are exactly the same people as we were before. The kids still see us working our butts off morning through night — even if these days many of our hours are spent pro-bono or to help a non-profit, rather than worrying about our own retirement savings.

Ah, little vs big. I think I found the answer to my friend’s question. I’ve always operated by the belief that it’s the little things that make the most important difference. And how we raise our kids should be no exception.

Actually, there are no rich kids

A few months ago we were having lunch at home when our youngest, Asher, casually asked us, “Hey guys, are we a little rich?”

Our answer started with, “Well, Asher, you are certainly not rich. You’re just a kid!”

We then gave him a brief talk about why it’s important to always work hard in life, take chances when you truly believe in something, be grateful for things to work out (because they don’t always), recognize that many people don’t have what we have (but they still have every reason to be as happy as we are), and even when you have more money than you need, remain thoughtful about how you spend it.

I don’t know how much that one conversation will stick with him. But there are countless little opportunities to impart these same messages each and every day: the ongoing grind of household chores, the chance to save $3 on a purchase at Target, when something breaks in the house (which happens a LOT in a big house!) and we need to roll up our own sleeves, and of course, each and every time we interact with another human being.

These little interactions, little decisions, and little events are like the ongoing force of gravity; always present as an opportunity to keep our kids grounded.

I’ve certainly been far from perfect in many of these circumstances but to-date I could not be more proud of the character and values embodied by our kids. After all, it’s been five years since our financial picture dramatically changed…. and he’s just now starting to wonder, are we a little rich?

Raising a baby vs raising a startup

A friend of mine recently asked, “What do you find the same about raising a baby and building a company?” To be honest, the question caught me off guard. It felt like a question I should easily be able to answer, but I kept struggling to come up with a decent response. Each is a time sink and will destroy your sleep, but saying “you get busy” or “they’re both hard” felt like lousy responses.

There is definitely a process of learning involved in both fatherhood and entrepreneurship, but to me, they are still very different. Figuring out what works for your child takes a bit of trial-and-error, but the general practices are well known and eventually things fall into place — even if it means having to try over and over, or waiting until your baby gets older and matures. Our first child has been a crazy challenge, but given that we as humans owe our entire existence to cave people, I’d say that parenting is still a relatively intuitive practice and hard to completely screw up.

Entrepreneurship, on the other hand, does not come quite as naturally. It’s a process of learning that requires you to challenge, and potentially disregard, what you thought you knew. You have to question everything, and you’ll often find yourself on a lonely island on which everybody is questioning you. Even with the right methodology, knowledge, and passion, you might just be at the wrong place at the wrong time. In other words: babies generally grow and thrive regardless of parenting styles, whereas startups tend to fail even when led by strong entrepreneurs.

Reflecting back on my friend’s question, I realize now that maybe I was too caught up in the mechanics. Yes, progress might not come as automatically with a startup as it does with a baby that is naturally growing, but there is a way in which the two are very similar: it’s the manner in which you approach them. Here’s the best way I can figure out how to say it:

Raising a baby and raising a startup both require making difficult sacrifices in order to enrich your life in a way that would otherwise not be possible.

Having a baby changes everything. We barely sleep, go weeks without watching TV, and generally can’t do anything on a whim anymore. It requires constantly putting someone else ahead of our own selfish desires. Yet, it’s completely worth it. There is a type of love, and a part of life, that I never knew existed until we had Dilan. And I can no longer imagine life without him.

Similarly, quitting a good job to start a company can be a a brutally challenging experience. It’s the act of trying to create something out of nothing, and there are a million ways you can fail. It’s the choice to be continually uncomfortable. I really believe it is the hardest thing I could have chosen to do. Yet, it’s also incredibly fulfilling. It gives me a tremendous sense of purpose and satisfaction. And I can not imagine spending my life doing anything else.

When I think about this way, I realize how incredibly fortunate I am to be able to answer my friend’s question.

What a crying baby taught us about customer value

Not long after our son Dilan was born, my wife downloaded a free iPhone app from the App Store called White Noise Box. It’s an incredibly simply app: there are 5 different images you can tap that each play a specific variant of white noise. For example, tap the image of rain for soft white noise, or tap the image of water rapids for more harsh white noise. Tap again and the white noise stops. About 8 weeks in, I asked my wife, “If Noise Box was a paid app, how much would you be willing to pay?” Her answer: “Thousands.”

Draining my iPhone battery playing white noise all day

OK, so realistically speaking, I would spend a Saturday learning Objective-C and hissing into a microphone if I thought my wife was really about to drop a couple Gs on an iPhone app. Nonetheless, her response is instructive. Despite the fact that the app is nothing more than a couple of images and .wav files, the value of the app is immense. Why? For the longest time, the harsh white noise of water rapids was the only thing that would calm our excessively challenging newborn. We could change his diaper, swaddle him, sway him, sing to him, and fall to our knees begging for mercy to no avail. Tap the image on White Noise Box, however, and instant calm. It still works like magic 80% of the time.

For an entrepreneur, customer value is one of the most critical concepts to understand. It doesn’t matter whether it takes a day or a decade to built it. What really matters — at least in the case of “painkiller”-type products —  is the degree of your customer’s pain, and how well you alleviate it. Now to be fair, there are certainly other factors that come into play when setting price and assigning a value to your solution. In this case, it is fairly obvious that customers would evaluate competing products and alternative solutions (like running the vacuum cleaner) if buying White Noise Box meant wiping out the college fund. Even still, that doesn’t mean that an app this easy to replicate has to be free or super cheap. Imagine this for a moment: White Noise Box is called “The Baby Soothing App” in a sea of other generic white noise apps in the App Store.  It was featured in the latest issue of Happy Baby Magazine, and it popped up in at least 10 different forum answers you read between 3 and 5am last night (one-handed on your iPhone while trying to calm the little one). All of the moms on your street swear by it.

Now… look at your crying and consistently cranky baby. You can try your luck sifting through dozens of two-and-a-half star white noise apps in the App Store because they are all free, or you can succumb to the miracle $20 Baby Soothing app. I think you drop that Andrew Jackson and never look back.

Two lies I was told as a new father

Nearly three months ago, my wife gave birth to an incredible baby boy named Dilan. One of the great things about becoming a new parent is that there is an abundance of people you can turn to for advice. After all, 6+ billion children didn’t just appear out of nowhere!

Unfortunately, despite all of the tips we were equipped with, our first several weeks with Dilan turned out to be exceptionally rough. In fact, there were two key pieces of advice that I now realize sent us totally in the wrong direction. Now, it is probably a bit unfair to refer to the advice we received as “lies” because it was surely well-intended (and truth be told, we are extremely grateful for almost all of the tips and suggestions we were given!). I am calling it out, though, because it was advice that we heard very consistently and yet it was fundamentally flawed. Also, I realize that every baby is different, but hopefully this helps some other parents out there.

“You can’t overfeed your baby.”

Wrong. I can’t tell you how many people explicitly said this to us, including nurses, lactation consultants, doulas, and pediatricians. It turns out that virtually all of the advice a new mom receives in regards to breastfeeding is based on the assumption that breastfeeding will be impossible. Fortunately for us, Dilan figured out how to breastfeed rather quickly and is really darn good at it. The boy was born to eat.

The problem is that we were consistently told to keep him on the breast as long as he wanted… and he wanted to stay the entire day. As a result, he kept overeating. I can’t tell you how many times milk gushed out of his mouth. It is really hard for a baby to sleep, or be happy, when he’s constantly spitting up all over himself.  It wasn’t long before we began asking questions about his ridiculous amount of feeding, but we were always told the same thing, “Ah, let him feed when he wants to. Newborns can’t overfeed.”

It turns out that half the time he was feeding, he was just feeding to soothe. He didn’t need to eat — even if it seemed like he was “rooting” or showing some of the other typical hunger signs (I think he began to associate those behaviors with soothing). He just needed to suck on something, or simply receive some other form of comfort. It sounds obvious now, but I am surprised that nobody ever brought this up to us. We are now very careful about trying not to overfeed him, and he is a much happier baby.

“Newborns sleep almost the entire day.”

OK, this is not completely untrue, but it is misleading. It should be, “Newborns need to sleep almost the entire day.” The problem with the above statement is that it implies that the sleep will just happen on its own. Maybe it does for some babies (apparently for all of the baby girls our friends are having!), but not for our boy. For the first few weeks, we thought we would just hold him or swaddle him while going about our usual day, and that he would pass out as needed. Instead, he was wide awake most of the day and very, very unhappy. It is called being overtired. And despite all of the advice we were given, nobody ever mentioned this to us.

The solution is that we had to soothe him to sleep. And by soothe, I mean spend anywhere from 30 minutes to 2 hours working (not kidding!) to convince him to fall asleep. We’ve nearly perfected it to an art now — and can sometimes get him asleep in under 10 minutes — but essentially the process involves the following:

  • Monitor him closely when he has been awake between 1 – 2 hours. That seems to be his limit. He’ll stop playing as much and will start to get fussy. The sooner you detect he is tired, the easier he will be to put asleep.
  • Get him out of the noise and lights. When he is tired, it means that he is also overstimulated.
  • Swaddle so that he won’t keep driving himself crazy by flinging his own arms and legs everywhere. This was the one piece of advice we heard from the very beginning. It is a must, but not the silver bullet we thought it would be.
  • Cradle him and rock, swing, or sway. This is why Fischer Price sells a lot of swings. Again, not a silver bullet for us either.
  • Play loud white noise. This is the final ingredient, and the true secret weapon. When he is fussy, nothing other than feeding him can get him quiet like white noise. It works like pure magic 80% of the time.

Like I said, every baby is different and perhaps the above two statements actually ring true in most cases. Regardless, my wife and I are really surprised that nobody ever told us about overfeeding and overtiring. After figuring this out on our own, we have since come across some great resources online like these sleep guides: http://www.troublesometots.com/baby-sleep-guides/. It is actually kind of funny to see our crazy routine spelled out almost exactly in these guides.

A baby that eats properly and sleeps properly, is a happy baby. For those of you still trying to find your happy baby, I really hope this helps. I’d love to hear your comments!