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It’s not a sexy topic, but it needs to be discussed: healthcare for entrepreneurs.

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Healthcare: Try not to lose

Here’s the problem with healthcare… you can never really win, you can only hope not to lose.

– If you pay a lot of money for premiums and have a bad accident and everything gets paid for, well, you had an accident: Lose
– If you pay a lot of money and never get in an accident, well, you paid a lot of money for nothing: Lose
– If you get a really cheap plan (or have no insurance at all) and have a bad accident, well, now you had an accident and are broke: Really lose

The only way to win is to take an incredible gamble and not have insurance, live life to its fullest, and yet somehow never get in an accident. If you can pull that off – and not be incredibly stressed along the way – then you’re one of the lucky ones.


For most of us, the answer lies somewhere in between.

(At the end of this column, I’ll show you specific recommendations)

Health Insurance for entrepreneurs: What to consider

First off, the big disclaimer: I am not a doctor or a lawyer or have any more knowledge about the insurance industry than you probably do. I’m just a guy that loves doing research when I can’t find good answers on the web, and this is such a situation. You need to make your own decision based on your specific family situation, medical situation, tolerance for risk, and where you live.

That being said, here was my thought process, in hopes that it helps you.


College Career Advice
Hanging with college students makes Jim reflect on what really matters

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Back to School

In the same week I had the opportunity to do two cool things… go to an alumni event to answer grown-up, work-related questions from students, and host two students for the day in my college’s “shadow” program. As I joked on Facebook: On tap… a conference call for my biggest project, networking meetings with two other alums, and recording a podcast. My 4pm power nap is going to be awkward though.

In answering questions and thinking back to what I learned in school vs. what was useful in the real world, I came up with the following:


One year ago today (Nov 1) I made the leap and started my own business. Here’s what I’ve learned.

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November 1, 2011

I’m publishing this on November 1, 2012, exactly one year to the day that I was laid off from my full time gig at Conde Nast and Wired. I thought it would be a great time to give my fans an update and share some of the tips that I learned so far.

First off, I want to start by declaring that I am renewing my contract for another year.

What do I mean by that?

When I lost my job, a lot of people quickly offered help at finding something new, passed along openings, or wanted to meet with me. When I told them I wasn’t planning on getting a new full time gig, the next question was asking me how long I was giving myself to succeed, which also might be viewed as “when do you think your money will run out.”

While I never really set a hard deadline, I figured I would definitely give it a run for a year and see what happened at that point. Well, while I might not be back up to the full time salary with benefits and 401(k) that I was at, there’s no question that I am going to keep going down this path. Put it this way, I haven’t updated my resume yet.

Here’s another great sign. I just got the traffic stats, and October 2012 was the highest number of unique visitors this year and highest number of page views in the 4 1/2 year history of The Hopkinson Report. So thank you.

Here are 5 things that I learned as an entrepreneur in year 1:


Jim interviews entrepreneur, actress, and video storyteller Monica McCarthy of Show and Tell Stories.

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Time for Show and Tell

It’s really quite simple… take the fact that the new media world we live in is evolving and people are becoming their own brand + the meteoric rise of video on the web and you have Show and Tell Stories, a company that uses video to help people tell the world who they are.

I sat down with Monica McCarthy, the founder and creative director of the site to, well, hear HER story.

As with all my interviews, it is best to listen to the podcast above or subscribe on iTunes to get the full interview, but below is a highlight of the things we talk about.

The Big Picture

I feel there are 2 massive trends that are going to change everything: Mobile and Video. On the mobile side, there are 5 billion people that own cell phones but not smart phones, and a $20 Billion underutilized ad opportunity to reach people on those devices.


The conversation continues as Jim is interviewed by Mike Andrews, a typical listener with common questions on how to get started as an entrepreneur (part 2)

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The conversation continues

Last week we tried something new. Rather than Jim interviewing a guest, budding entrepreneur Mike Andrews asked Jim the questions about his experience as he was starting out. Mike dubbed it the “Sensei Sessions,” and is still amazed it only cost him a lunch to get as much information as possible out of Jim.

Since the interview went long, we split it into two parts over two weeks.

In case you missed it: Click here to view Part 1 of the Sensei Session interview.

As usual with interviews, your best bet is to subscribe on iTunes or play the entire show from the links above. But here is a summary of what we covered: