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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What to consider in your startup job offer

Photo credit: Unfinished Business movie stock image

Photo credit: Unfinished Business movie stock image

Every week someone asks me for advice about a startup job offer. I have no idea why people reach out to me about this. I’m not an expert on job negotiation by any means; but I have done a fair amount of hiring and deal making as an entrepreneur.

This post relays the main advice that I typically share to friends considering their startup offer. Hopefully I can use this post to direct my job-hunting network and save myself some time typing this advice over and over again.🙂

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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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Let’s destroy this myth

I’m super excited to announce that Hustle Con 2015 is officially happening on April 24, 2015 in San Francisco! This is an event for non-techies who are interested in starting startups, and it’s the third year we’re hosting this event.

So what is the point of our conference? Why do we exist when there are a gazillion other tech conferences?

Well, my team and I are on a mission to destroy a myth: that you need to be a techie in order to start a startup.

I meet so many would-be entrepreneurs every year who have awesome startup ideas, but are afraid. They make excuses like this:

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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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