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?

Back to the blog (I quit my job round #2)

It’s been 3,379 days since I last posted on this blog. A lot has happened in life since.

Here are a few personal updates about what happened after I last tried to compare building a startup to raising a baby in 2013:

  • I became a serial father. Our second son, Asher, was born in 2015. He’s now almost eight and is an amazing kid full of happiness, creativity, cleverness, and love. And Dilan has since grown into an equally wonderful 10 year old.
  • My startup idea worked! Our software has now helped thousands of cities, counties, law enforcement agencies, and other government entities more transparently engage with citizens. We even took on the President of the United States as a client…and yes, that other President too.
  • I quit my job, again.

OK, this time was a little more glamorous than the job quitting that launched this blog. Here’s what I wrote about it in late 2019 to my friends and family on Facebook:

Eight years, ten months, and eight days ago… I wrote a post on my personal blog called “Call me crazy. I quit my job.”

Well, call me crazy again. But this time is different.

In December 2010, I stepped away from IBM to chase a dream. Somehow, and unbelievably, I have had the great fortune over the last eight years to fully realize and surpass that dream.

It wasn’t easy. To be honest, it was absolutely grueling. But it was led with purpose and more rewarding and fulfilling than anything I could have ever taken on.

The company I founded continues to grow rapidly and amplify its impact on the world. And I am honored to continue to be a part of its story.

Like in 2010, this was my decision and exactly the right one for myself and the people I care about most — which now includes nearly 70 people in downtown Durham!!

I am deeply, deeply grateful to all of you who have supported me throughout this journey. Thank you. The greatest fortune I’ve had in life is the opportunity to spend my time with extraordinary people — and none more extraordinary, inspiring, and supportive than my partner in life, Varsha.

I don’t know exactly what’s next, other than pursuing what feels like yet another incredible dream: spending as much time as possible with Varsha and our two super sweet, rapidly growing boys. After all, I’d be crazy not to 😉

So why bring this decade-old blog back to life again? I know that Google bot is likely to be my most avid (and perhaps only) subscriber.

That’s why… I’m doing this for me.

Yes, there is hope that others will occasionally find value on this blog, and perhaps I can even use it to build out my personal brand. But more than anything, I’m at a point in my life where I kind of want to restart the cycle; to go back to where I was (in a professional sense) in 2010. Exploring, building, and journaling the journey. I am the “archiving guy” after all.

Because when I look back, I see now that this sparsely populated blog was an important outlet for me; it served as a personal (yet public) ledger of the growth, progress, and learnings I experienced over a time period during which I often felt like I was failing and flailing.

I don’t know yet if I will start another company like ArchiveSocial. But I am itching to find my next purpose in life and to get back to creating value in the world.

In the meantime, some topics I might share perspective on using this blog:

  • Hard founder decisions, like choosing to sell a company and stepping back as CEO
  • Life after exit — including all the stuff (good, great, bad, & ugly) you encounter but nobody with wealth and professional freedom talks about because your life is supposed to be perfect
  • The marathon-sprint of raising little kids while pursuing demanding careers (and how to be a better husband)
  • The entire basket of learnings from scaling a company from $0 to over $10M in annual recurring revenue — including some fun and crazy stories
  • Figuring out what’s next when (conceptually) you can spend your time on almost anything you want to

To my friends, colleagues, and family who might run across this post: let me know if any of these topics grabs your attention. I might write about it here. Or at the very least, I can credit the relaunch of this blog for motivating us to grab a beer.