When I first started watching tastytrade, I used to wonder how the episodes of “Bootstrapping in America” related to options trading.

However, the more I watched the episodes about all of these amazing entrepreneurs, the more I realized the similar personality traits between entrepreneurs and do-it-yourself investors.

A Brief History Of “Bootstrapping In America”

Back when tastytrade created its options trading network, they started developing a lot of great financial content. In an effort to reach new audiences and expand on their success, tastytrade created an additional show with a broader, related focus that included a wide range of guests.

Tom Sosnoff preparing for the show with "Bootstrapping" creator Jules Weinstein.

Tom Sosnoff preparing for the show with "Bootstrapping" creator Jules Weinstein.

Jules Weinstein, the originator of the “Bootstrapping” series, thought having a show on tastytrade that focused on entrepreneurialism would be a great fit, and would also be a way to highlight the budding entrepreneurial/tech scene in Chicago (home of tastytrade’s global headquarters). Before long, tastytrade started airing episodes with business owners in Chicago and eventually all around the country to share their stories - and so "Bootstrapping In America" came to life.

How Bootstrappers Relate to Options Traders

There are actually remarkable similarities between entrepreneurs and traders (I mean, if you think about it, full-time traders are entrepreneurs).

Below are four common characteristics between entrepreneurs and traders that I find to be true:

1) Accountable

Entrepreneurs want to take control and responsibility over their destiny. They want to start a business and focus their effort and time on pursuing a goal close to their heart. 

Traders are exactly the same. We want to take our money matters into our own hands, and a great way to do that is by learning about investing.

2) Opportunistic

Both entrepreneurs and traders see opportunity all around them. They have a keen sense of how to make lemonade when life hands them lemons. Even in down markets, traders know there are trades to be placed, just like entrepreneurs know there are opportunities to seize.

3) Risk-Takers

As any business owner will tell you, entrepreneurship is about taking risks. Your company might be taken over by a bigger giant and you will make oodles of money in the process. Or, your not-for-profit may be able to help a million people in a giant tsunami. Whatever it might be, you know there will be risks in order to grow your business.

Traders know as much about risk as entrepreneurs. We are consistently taking risks with our money in the trades that we place - the only difference is that tastytraders have more knowledge about options trading and the risk involved.

4) Innovative Thinkers

Let’s face it, building a business takes creativity, and so does trading. 

No two businesses are the same and neither are two trading accounts. Both entrepreneurs and traders think outside the box to solve their problems. We are always looking at our business problems or trading issues with a creative eye. 

To summarize...

The more I look at the list above, the more I realize the confluence between entrepreneurship and do-it-yourself investing. They bring similar characteristics to their respective industries.

We are also lucky as traders to be privy to the conversations with entrepreneurs and experienced traders. So soak it in, and use it all to help guide your trading strategy. 

If you haven’t seen "Bootstrapping in America" yet, give it a shot and you’ll see informative interviews with interesting entrepreneurs. Let me know what you think about the show (and if this list runs true) below in the comments. 


If you haven't seen "Bootstrapping in America" yet, check it out live on the tastytrade network Monday-Friday mornings. Follow the show on Twitter @BootstrappingIA and never miss an episode!