At Sheryl Sandberg’s talk the other week, she asked the audience a question from her book: “What would you do if you weren’t afraid?”

It’s a great question, and one about which I’ve been thinking since. Am I afraid? If so, of what am I afraid?

Coincidentally, a friend of mine is a successful VC and has decided to step back and instead pursue a career path in executive coaching. Using a framework and methodology from Harvard, I’m the first beta customer. The point of the sessions is to release someone’s full potential by identifying and then overcoming your greatest personal fears. We’ve only met up twice so far, but it’s been pretty cool.

What’s particularly interesting is that I’m starting to realize that my biggest fear, deep down and which took some unearthing, is to avoid a rough five-year patch in my life starting in 2nd grade.

You see, we had left the U.S. to move back to Indonesia, but shortly thereafter, my mother became very ill and almost died a few times in front of my eyes (her kidneys had failed, which led to numerous complications). My sister and I were living with a childless aunt who didn’t have a clue about parenting and was pretty harsh.

We were enrolled in a local school, where our American accents made us seem foreign. The culture shock was insane: brutal heat and humidity, no air conditioning, insane traffic, and social customs far different from the inner-city world of Brooklyn.

After a few months, we then moved back to the U.S. so that my mother could get better medical care. My parents spent a lot of time away from us while at the hospital, whilst yet another childless-and-harsh aunt took care of me and sister.

So, clearly, our world had changed drastically. My mother was the life of the party, cooked like a fiend and kept the house neat and bright. As she struggled for her life, and later, went through dialysis treatments to keep her alive but depleted and depressed, our home became quiet, we ate a lot of junk food, and the house was a pigsty.

Our lives were in a holding pattern, and disaster always seemed to loom around the corner. My mother frequently went to see her doctors, and you never knew if the latest blood test or examination would show a worsening condition or hint at end-of-life. The uncertainty was pretty constant and dis-comforting.

I remember as a child thinking to myself that I better shape my future. In third grade, for example, I cooked Thanksgiving dinner. It sucked. But, I didn’t want to go without, and I thought, “Well, who else is going to cook it if I don’t?” Did I really want take-out, junk food or frozen food for Thanksgiving dinner?

Thankfully, things changed when my mother received a kidney transplant, but since donor kidneys have a limited half-life, she was always worried that her health would go again. Life always felt tense and precarious to me as a child.

Perhaps it’s why I work a lot and have a sense of urgency. I’ve seen that bad things can happen to good people. Time is precious.

It’s a good thing that I made friends easily, for that let me play at other people’s houses and see brighter households. I encountered parents who went to their children’s sports games and practices, asked about their grades, and seemed really interested in their kids’ lives.

I saw home-cooked meals and clean homes. I saw stability. I’m sure those families had flaws, too, but to me, they seemed like glimpses from a Norman Rockwell painting, like the one above.

And, all that is what I wanted for my future children.

I’m not sure how else these personal experiences have shaped me, as I’ll find out more in the coming sessions with my friend. And, I know that sharing all of this personal stuff might be TMI for some of you. But, I think a first step in overcoming a fear is to name it and put it out there.

And, I’ve just done that. I’m very grateful to my friend.

This is a hard post to write. Today is May 12. It is the day of my mother’s birthday. She also died, at age 60, on May 12. That day also happened to be Mother’s Day. It was a difficult day with too many coincidences.

Soon after she passed away, I was at the funeral home. My mom kept in shoe boxes every greeting card my sister and I had ever given her. She had asked my sister that the boxes be placed in her casket after her death. I didn’t know about either the boxes or her request, until after my mother died.

And so, there I was, waiting for the funeral director, going through card after card as I relived past decades. There were hand-drawn cards from our youth, with unsteady writing and crayon pictures. There were also the polished store-bought cards I had sent as an adult. Birthdays, anniversaries, holidays. Too many memories. In shoe boxes.

The director came up to me. I stood up and handed the boxes to him. Giving away those cards was hard.

Afterwards, I drove back from the funeral home, and I thought about many things. In the silence, I thought about how my mother didn’t want to emigrate to the U.S. and leave her family, friends and culture. I remembered the very hard life we had when we first moved here with just $1,500. I remembered well our dilapidated apartment in a beaten-down part of Brooklyn. But, in the end, my mother persevered. She wanted a better life for her children.

As I drove, I regretted that I had never thanked my mother for moving to the U.S. It was a long drive.

Growing up, my mother used to say to me: “Please work hard at whatever you do for a living.” It was her polite way of saying: “I’ve given up a lot so that you might have more–so, don’t waste my sacrifice.”

Why do I write this? First, I think many VCs like what they do because we really identify with people who want to chase the American Dream. I definitely do.

To me, being a VC is not just a job. It’s personal.

Second, I find that many entrepreneurs can point to a person, who unwittingly planted the seeds of entrepreneurship in them early in life. I have met with probably over 5,000 founders in my venture capital career. They come from many backgrounds and areas of life. Not everyone shares why they are starting a new company, but when they do, the stories are fascinating. I find that these intensely personal “drivers of drive” are very inspiring.

I’d like to close with two last items. First, if you’re an entrepreneur, I’d love to hear about why you are one. You can always get a job working for someone else, but yet, you’ve decided to start something new. Why?

Second, to my mother, I hope this somehow gets to you: a very belated and deeply-felt thank you….

I’ve cancelled one of the kids’ weekend activities, but I will still be driving them around to some sports lessons this morning and am in charge of their meals.

Now, I’m lucky. These are “first-world problems,” I know. If I don’t have the energy to cook, I just call a pizza place or a restaurant delivery service. We have the money to do so.

This experience, though, makes me wonder as to how single parents do this job, day after day. And, if the single parent is working at a series of minimum wage jobs, how do they keep their personal insanity and create a great homelife for their kids? My guess is that many don’t.

So, here’s a personal nod to single moms and dads everywhere. I do not know what you’re going through. But, I want to say that I admire your mental toughness. I hope your children are showing their gratitude to you. I hope you hang in there.

By the former, I think of it as: multi-dimensional, creative, having disruptive potential. By the latter, I think of: logical, incremental, thoughtful (but almost obvious).

I think entrepreneurs are predominantly orthogonal thinkers. My partners and I often mention how entrepreneurs truly do see the world differently. They see the same pieces of information that the rest of the world does, but for some reason, they’re able to project further into the future and see potential that others cannot.

The challenge with backing entrepreneurs is that the orthogonal point of view can often create blind spots and irrational exuberance  So, as a VC, you have to work hard at enabling entrepreneurs to “go for it,” but at the same time, give advice as to when you think they’re going off the reservation.

Believe it or not, VCs have very little day-to-day power. We can influence people and situations, but we aren’t at the companies every day. Sure, we can give up on companies and force a shut down, or we can fire people (I call these the “nuclear options”).  But, you in practice rarely use those options without the entrepreneur’s consent. There needs to be a lot of trust there in the relationship.

It’s ironic, but venture capital means you have power but that you rarely use it. You really in the end have to let entrepreneurs do what they want. And, if they fail, you have to give a helpful ear and give them a hand. And, when they succeed, you hope they stay humble and hungry.

I love working with people on ideas that matter. It’s awesome to see teamwork originate and execute such a fantastic event.

I remember a brainstorm session during which C.A. Webb, Chris Sheehan, Stephen Kraus and I discussed what events we could do for the start-up ecosystem. Frankly, I didn’t do much. But, I did voice a strong opinion that it would be lame to do anything formal, stuffy or boring. I was hoping we could do something really unifying, energizing and fun.

So, Stephen came up with the idea for an awards ceremony and a team comprised of C.A., entrepreneurs and VCs worked together. Here’s what C.A. wrote earlier today to the NEVCA Board:

Thanks to Steve for developing and pushing for the idea and leading the committee over these last 4 months. To [Mike Troiano] for his expert crafting of the message, design and strategy. And to [David Beisel] for contributing great thinking to our committee. These guys put in some serious time to make it great–as did Fred Destin, Michelle Dipp and Bob Hower in particular so please thank them when you see them. And I continue to marvel that [Casey Hogan] is just 21 and in college…we could not have pulled off this even without her.

I’m sure dozens of people worked on this project, and I’m sorry that I don’t know everyone by name. And, amazing sponsors helped support this event (see below).

I love this town. I love our start-up community. Last night, we as a group of entrepreneurs, VCs and service providers, truly were One Team.