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Taking Calculated Risks and Elevating Your Network

Jayson Gaignard was heavily in debt, had driven his business into the ground and was starting to hit rock bottom. He was creeping closer and closer to filing bankruptcy.

At this point, shockingly, he decided to do two things.

First, he decided to max out $10,000 on a credit card for an event Tim Ferriss hosted called Opening The Kimono in 2010. It was a high-end, exclusive event held for aspiring best selling authors that hasn’t been held since.

Jayson didn’t have the aspiration to be an author, but he knew that at $10k per entry, the level of entrepreneur would be impressive. So, he made the investment and attended the event.


While the content was fine, the network and friendships he formed became the foundation of what would eventually embody Jayson’s super power.

Jayson has the innate ability to connect with people and then to start connecting dots in his head about who he should connect the person with based on common interests, struggles, business industry, business size and any number of things that the person cares deeply about.connect-316638_640


This super power started out with Jayson hosting dinners, something he coined and authored a book on called, Mastermind Dinners. In short, he would host dinners for 10-12 people in a certain city and invite high level entrepreneurs that didn’t know each other, but that Jayson felt should know each other. He would bring these folks together over a meal and then sit back and observe the interactions between the dinner guests, tweaking seating positions as needed so everyone could connect with the people they are sitting near.

This was a catalyst for many friendships and business deals amongst the dinner guests for years to come. Jayson still hosts these dinners today.


This idea then parlayed into the second big risk he decided to take being nearly bankrupt with nothing to lose at the time.

This second decision, oddly enough, also involves Tim Ferriss.


Jayson was waking up very early at this time in 2011, so he was up at 4am EST while Tim was just going to bed at 1am PST at his home in San Francisco. Tim sent out an email selling book bundles for the 4 Hour Body. The highest end package that he offered was for $84,000 and that included 4,000 copies of the book and two speaking engagements from Tim.

Jayson at the time, had a very good friend that ran events with 2,000 to 3,000 people, so he immediately thought that it would be a good opportunity to send it to him. On second thought, however, he realized that this was an amazing opportunity for anyone, not just his friend. So, he emailed Tim and told him he wanted to purchase the package. Tim was shocked to say the least. He didn’t think anyone in their right mind would buy that package.

So, Jayson, who was in debt at this time, had to come up with $84,000 within a handful of days to lock down the bundle.  

He reached out to three people he knew for the investment.


The first one asked for a business plan, which Jayson didn’t have and didn’t care about creating.

The second person liked the idea and wanted to split the equity in the investment at 50/50 to become partners.

The third person told Jayson to come by his office the next day to pick up the check for $84,000 with no questions asked.


What Jayson had come to find out was that the third guy didn’t need to know or care what the opportunity was, he just 100% believed in Jayson as a human being to care for that money and be a good steward of it.


This is how the event, MastermindTalks, was created. Jayson was able to have Tim Ferriss speak at the event which garnered a ton of interest as Tim doesn’t do many live speaking engagements. With Tim as the featured speaker, Jayson was able to sell nearly $180k in tickets to the event. He was able to recoup the $84,000 and pay back his investor, without interest. And he was able to pocket a little money for himself for putting the event together. linked-152575_640


The most valuable lesson learned from Jayson is that the bank could take his house, his car and his possessions, but the one thing they could not take…his relationships.

So, Jayson to this day has gone all in on creating high value, reciprocal relationships and without hesitation will tell you it’s his most valuable asset.


I often hear the quote, “Show me your friends and I’ll show you your future.” In my opinion, truer words have never been spoken. And as Jayson always says, “If you’re the smartest person in the room, you’re in the wrong room.”

What can you do today to elevate your network and surround yourself with people that are achieving goals that you want to be achieving?

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