Category Archives: Life



Yes, I look like a complete idiot in this photo.

Looking back at when I ran my education startup (2005 to 2012), I recall a lot of emotions and feelings. I remember existential stress, since from my perspective I was building a house of cards that could collapse at any moment (I was a little bit young and dramatic). I also remember exhaustion, as I poured everything I had into this startup; progress was always shaky and turbulent. I sacrificed health and relationships along the way.

But most vividly, I recall joy and purpose in running my startup.

My startup experience was weirdly spiritual. At the time I firmly believed that God had put me on earth to build the company I was building and serve the community I was serving. Despite all the stress and exhaustion, this underlying joy brought me tremendous peace, giving me strength push myself beyond what I imagined I was capable.

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Advice for the 25-Year-Old Me

Sharing a libation with my best bro on my 25th b-day.

Sharing a libation with my best bro on my 25th b-day.

Kate, a young entrepreneur that I’m mentoring, recently sent me this e-mail:

I’m turning 25 in two days, and I’ve asked a bunch of people from my life what they wish they had known at 25. I’d love to hear your thoughts on what you’d tell your 25 year old self!

This is what I said:

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How do I become a good father?

How the heck did women give birth before modern medicine?

How the heck did women give birth before modern medicine?

As I am writing this post, my wife is in the midst of her 33rd hour of labor. Despite the lack of sleep and physical exhaustion, she still has a remarkably positive attitude and is determined to fight on; what an amazing woman! We’re excited to meet our boy, but he sure is taking his sweet-ass time to enter the building.

Yesterday I finished reading (actually, listening via audiobook) a fantastic book called, A More Beautiful Question, by Warren Berger. As you might imagine, this book is all about questions. The general summary is that people aren’t taught how to ask good questions, but that asking the right question at the right time can change lives, organizations, and society.

In the next few hours I will officially become a father. I can tell you with utmost sincerity that I have no idea what I’m doing.

Since I don’t have answers on how to become a good parent, I want to pose the questions I hope to explore while raising this child.

In no particular order, here are the questions on my mind when it comes to my son:

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How to see more beauty in the world

My favorite photography subject of all time, my wife!

My favorite photography subject of all time, my wife!

In 2015, I’m trying to take one thoughtful photo every day. I made a resolution to practice photography initially because I thought it would be a helpful life skill. I have a kid on the way, and heck, it would be nice to capture some embarrassing baby photos at the very least to troll him during his wedding slide show, some day.

I’m about 50 days into my art project; what I didn’t expect was how enriching photography would be to my life. Beyond the skill development stuff, photography has provided me a gift that I wasn’t prepared for: I appreciate the beauty of the world so much more.

Even when I’m not practicing photography, everything I see suddenly seems a lot more pretty. It’s amazing!

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Startup life wrecked my body

Car Crash

I have a lot of friends who are startup founders. Lately whenever we meet up, I find myself sharing the same story with them; it’s about a car accident.

I can’t remember where I originally heard this story, but it stuck with me as an important metaphor for startup life. It goes something like this:

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The only thing I’ll remember from my acquisition

Where my wife nearly died two years ago.

The gorge that nearly killed my wife two years ago.

It’s been over two years since my startup got acquired. People to this day ask me what I felt the moment this deal closed. Was it some feeling of satisfaction after bootstrapping my business for seven years? Was it elation in seeing a large wire transfer come into my bank account? Or maybe, was it validation from proving all my naysayers and competitors wrong?

Nope, I wasn’t thinking about any of that. The only thing I felt was gratitude. Not gratitude about my little startup achievement, but gratitude that my wife was actually alive.

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