Why Jayson Gaignard Bought 4,000 Books From Tim Ferriss When He Was Dead Broke

The Fail On Podcast with Rob Nunnery - Fail Your Way To An Inspired Life

Welcome to the first episode of The Fail On Podcast, where we believe that if you desire to create the life of your dreams then embracing failure by taking urgent and bold action is the only way. Today, we get to learn from none other than Jayson Gaignard, a super connector, the creator of MastermindTalks, and the author of Mastermind Dinners.

In this episode, Jayson shares with us his knowledge about elevating your network along with the best and worst ways to find mentorship, how he bought an $84,000 book bundle from Tim Ferriss while being absolutely broke, and how embracing failure, taking risk, and getting out of his comfort zone completely transformed his life, and so much more.

Key Points From This Episode:

• Hear the story of the first time Jayson provided a service or product in exchange for money.
• Jayson shares the first failure he experienced in the world of entrepreneurship.
  Find out about Jayson’s first lucky break, where things finally clicked for him in business.
• Discover the best, organic way to approach a potential mentor and why it is key to remain teachable.
• Understand the aspects Jayson considers to be the most painful parts of being an entrepreneur.
• Learn more about MastermindTalks, how it got start, the goals and where it is going next.
• Hear the story of how Mastermind Dinners got started during the time that Jayson was considering bankruptcy.
• Jayson shares how he bought an $84,000 book bundle from Tim Ferriss when he was broke.
• Discover the ways the Jayson forces himself to get out of his comfort zone.
• Find out who the one person was who had the most impact in Jayson’s life over the long term.
• And much more!

Tweetable:

“Never tarnish your word and always invest in your network.” - @JaysonGaignard

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Links Mentioned in Today’s Episode:

MastermindTalks
Jayson on Twitter
Jayson’s book, Mastermind Dinners: Build Lifelong Relationships by Connecting Experts, Influencers, and Linchpins
Jayson’s podcast, The MastermindTalks Podcast
Tim Ferriss
Joe Polish of the $25K Group
Tim Ferriss’ book, The 4-Hour Chef: The Simple Path to Cooking Like a Pro, Learning Anything, and Living the Good Life
Philip McKernan

Read Full Transcript

EPISODE 001

“JG: If I could boil down the success of last 13 years is I’ve always surrounded myself with people who are one or two steps ahead of me and what that does on an unconscious level, I mean, we all have a deep desire to belong to a peer group and when you surround yourself with people who are ahead of you, unconsciously it pushes you to get to their level as quickly as possible so you could feel like you belong.”

[INTRODUCTION]

[0:00:25.1] ANNOUNCER: Welcome to The Fail on Podcast where we explore the hardships and obstacles today’s industry leaders face on their journey to the top of their fields, through careful insight and thoughtful conversation. By embracing failure, we’ll show you how to build momentum without being consumed by the result.

Now please welcome your host, Rob Nunnery.

[INTRO]

[0:00:52.1] RN: Hello and welcome to the podcast that believes, if you desire to create the life of your dreams then embracing failure by taking urgent and bold action is the only way. Today, you and I get to learn from none other than Jayson Gaignard, a super connector, the creator of MastermindTalks, and the author of Mastermind Dinners.

I’ll be talking to Jayson about elevating your network along with the best and worst ways to find mentorship, buying an $84,000 book bundle from Tim Ferriss while being absolutely broke, and how embracing failure, taking risk, and getting out of his comfort zone completely transformed his life, and much, much more.

But first, if you’d like to stay up to date on all fail on podcast interviews and key takeaways from each guest, simply go to failon.com and sign up for our newsletter at the bottom of the page.

Now, without further ado, Mr. Jayson Gaignard.

[INTERVIEW]

[0:02:02.9] RN: Hey there and welcome to The Fail On Podcast, I’m so excited for today’s show for two reasons: One, we’ve got Jayson Gaignard in the house, the founder and head talent scout of MastermindTalks, an annual invite only event designed for lead entrepreneurs with an acceptance rate lower than Harvard. And reason number two that I’m so pumped is that we’re sitting here together in beautiful Eleuthero, an island in the Bahamas. Thanks to Jayson and Candice, his wife for organizing the trip, for a small group of MastermindTalks members.

Jayson, welcome to the show my man.

[0:02:30.7] JG: Excited to be here dude, this is by far the earliest interview I’ve ever done. Especially for somebody like you because you’re Eastern Time, it’s 6 AM eastern time, so for you it’s like 3 AM. So thank you for having me on.

[0:02:43.1] RN: Whatever it takes to get you on the line man.

[0:02:46.6] JG: I’m freshest in the morning, I’m excited.

[0:02:47.9] RN: No, I am too. Not usually at 3 AM but usually at 5 AM. But we’ll go into MastermindTalks and your current products in a bit, but I really want you to take us back to the first time that you provided a service or product in exchange for money. When was that and how did it come about?

[0:03:01.6] JG: That’s a great question. I guess, two incidences come to mind. First was, I guess one on some level, I was used as a contractor. I had a newspaper route where I had to collect money and I got a portion of that. That was one thing I don’t know how old I was then, but then I had a snow shoveling business in Canada and a lawn mowing business and the funny thing is I remember making flyers, my mom still has thousands of these bloody flyers I made for some reason.

I made it with like clipart on the front and you opened it and had this like text or copy that was full of spelling errors and that kind of stuff and I handed out like probably like 900 of these things, didn’t get a single call and then on the last like 50, I ended up writing a handwritten note at the bottom saying, “I’m a 13 year old guy,” just like this kind of — there were all these like crappy copies that were full of spelling mistakes and then I gave like just this vulnerable transparent copy of really who I was and that kind of stuff. Because I was trying to be this big business getting lawn-cutting clients.

[0:04:02.2] RN: How old were you?

[0:04:03.3] JG: Probably about 13.

[0:04:04.5] RN: Okay.

[0:04:06.3] JG: Ended up getting, out of the 50 I sent out, I end up getting response of eight or something like that. So my conversion rate went through the roof by being vulnerable in that copy. So that would be the first time I kind of I had some kind of product or service to offer in exchange for money.

[0:04:20.3] RN: That’s cool, you’re being transparent off I think before it was cool.

[0:04:23.2] JG: Dude, before it was hip.

[0:04:25.1] RN: Man, that’s awesome. Let’s go to what you consider your very first failure in the world of entrepreneurship, whether it’s a macro large scale failure or micro failure that you ran into just getting started. What was it and how did it come about?

[0:04:37.4] JG: Well that was kind of a failure right off the gate, I mean, as far as hand delivering 950 of these things.

[0:04:43.4] RN: Were you going door to door?

[0:04:44.4] JG: Yeah, locally in my neighborhood and it wasn’t the first time my direct mail efforts failed miserably. But that was like a micro failure and just thankfully for some reason I felt like writing a little note as far as — I didn’t realize the spelling mistakes until last year. I originally thought, “Oh, this is actually some really good marketing.” That would be like my first thing and then my first official business, I did a similar mistake with direct mail, which I got zero response rate period.

Which was I launched a concierge firm, which we’d run errands for people. So what happened was, I was — I dropped out of high school, became an automotive performance mechanic, did that for about a year and a half and then realized I was not going to change the world being mechanic and there’s no shots in mechanics. But I was clearing like $500 every two weeks when it came to my paycheck so I’m like, “This is not really the path to freedom and wealth that I was looking for.”

And then I quit on like a Thursday after like a year and then I got a job in car sales on a Saturday and ended up one day, I did it for a month, I did exceptionally well in that month. I think it was like second in sales and then I had somebody come in to buy a car and he knew the year make, and model and color and everything but he took three days off of work to do it and I’m like, “Well, it’s a poor use of your time to take all this time off of work, away from making money to save a couple of hundred bucks.” Like the opportunity cost is huge.

So I’m like, “Well, I’m going to start a business geared towards car shopping for people on their behalf,” and ended up starting a concierge firm instead. Which was really we’d do anything as long as it was legal and moral and would save people time. People were willing to pay $50 an hour and most likely do it. So I broke up with people’s girlfriends, I did all this — I walked their dogs, I would drive them around.

[0:06:22.3] RN: What was the one thing that kind of got really close to that line on the side where you’d say, “I can’t do that.”

[0:06:27.8] JG: the breaking up with somebody’s girlfriend was tough because I didn’t even break up with my girlfriend, so I was terrible at it but it was easier for me to break up with somebody else’s girlfriend on their behalf. So that was probably one of the more interesting ones.

[0:06:39.1] RN: That’s one an epic way to break up with somebody, right?

[0:06:41.5] JG: Yeah. It was also even more dick-ish by the fact that I was — I’d wear a tux. So I showed up at this lady’s house with like a box. I remember exactly like where she lives and all that kind of stuff, and I showed up to her house with a box and I’m like, “Are you so-and-so?” And she’s like, “Yeah.” I’m like, “Unfortunately, Joe doesn’t want to be with you anymore,” and I handed her a box.

[0:07:01.8] RN: The only thing that can make that better is if it was like in song and you’re singing it.

[0:07:05.7] JG: No, it would not make it better. It would make the situation way worse. While I’m wounded waiting, to answer your question, when I started that business, I had this genius direct market — I didn’t know about like online marketing or it was even a thing. So I had this genius direct mail marketing idea, which was I had this boxes made, again, a thousand. I do everything in large quantities for some reason, and I still have a bunch of these boxes and a bunch of these fortune cookies.

But I had these boxes and then you open up the box and there was like a little flyer about the business and then there was a fortune cookie in it and then the fortune cookie, there was a message about the business like, “Let us save you time over this holiday season,” or something like that. I hand delivered a thousand of this in my local area or in the areas that I thought was rich people. Zero response rate and I did it in dead of winter and I had these boxes, I could only deliver 200 at a time because it would fill up my car with all these bloody boxes.

So that was another failure for sure but I’ve been very lucky along the way, a few little lucky breaks. One thing about me that I’ve come to realize after being an entrepreneur for 13 years is that I think we all tend to have lucky breaks in business. But I’ve been smart enough to be or present enough to be able to identify those lucky breaks and I really leverage them and double down on them in essence.

[0:08:17.8] RN: Yeah, take us back to that first lucky break, where things started to actually, whether it be the concierge service or whether it would be a business after that, where something finally clicked and you're like, “Wow, I’m actually…”

[0:08:27.1] JG: I think two lucky breaks when it comes to my first business. The first was my accountant was like the first person I had contact with business wise, because he had to like setup my business and I had no clue even to where to go when it came to accounting. He became my first client and my biggest client for the first year.

So if it wasn’t for him becoming my first client, I would have no business for the most part of the year one and I may have given up. Very good chance I would have given up. So if it wasn’t for him and that just struck of luck, that wouldn’t have happened. I looked back and at like all I’ve done and accomplished in the last 13 years and I’m like, something so small as far as like that first client, I may not be here.

[0:09:01.4] RN: It could change your whole course, right?

[0:09:02.4] JG: Oh, most definitely. Then the second thing was my first mentor and how that happened was he was featured in this magazine called Profit Magazine in Canada which was similar to like Inc. They did like a half page spread on him on his business and what he did was, back then, was he helped companies get government grant money and at the time I was 18 so I’m like, “There has to be some grant money for me. I hear of all these people who get all this money from the government and I haven’t got anything and I don’t even know where to look.”

So I reached out to him and he’s like, he specialized in like Shred and tech, getting money from the government on the tech side of things. I ended up reaching out and he’s like, “You know, I can’t help you.” Pretty much just short and sweet and then the following month, I was featured in the same magazine and they had a three page spread on me and when he saw that, he ended up reaching out and he’s like, “Okay, let’s do dinner.”

So we did dinner and he was my first mentor and definitely again, without him, if I could boil down the success of last 13 years is I’ve always surrounded myself with people who are one or two steps ahead of me and what that does on an unconscious level, I mean, we all have a deep desire to belong to a peer group and when you surround yourself with people who are ahead of you, unconsciously it pushes you to get to their level as quickly as possible so you could feel like you belong, and with him — So we’ve got to give context for this episode. We have Ben Greenfield who is making some kind of concoction over there who is also a part of this trip, which was yeah, was doing a little dance for us and then we also have personal chefs who are behind us cooking us breakfast. So we’ve got to set the tone for the environment.

[0:10:26.8] RN: Yeah, there’s a little chaos going on.

[0:10:28.4] JG: But yeah, I had got him as a mentor and I was incredibly impactful. Mentors have been huge for me but one of the biggest things that he did as I remember looking back, I was doing maybe like $5,000 a month in sales at the time, like super small and he’s like, “Imagine a time when you’re doing like $80,000 a month,” and I’m like, “Oh yeah, yeah. I see it.” Intellectually I got a bit emotional, I’m like, “There’s no way I’ll ever do $80,000 a month.”

However, he helped me kind of reposition the business a little bit because I was going in service base direction and he really kind of pushed me to go on a product based direction and shout out if he listens to this. His name is James Pearly. Yeah, then after probably two and a half years later, I remember we did our first like $900,000 month and I was like, at that point, it hit me. I’m like, “Oh my god, I’m like two and a half years ago, I couldn’t imagine making $80,000 a month and now we’re doing like almost a million.”

It just goes to show like the power of like big thinking and how the people you surround yourself with can have a huge impact on that. That was definitely a lucky break. Since then, I’ve noticed the importance of surrounding yourself with people. That’s why I surround myself with Ben Greenfield. He’s so in shape, every time I’m around him, I feel like a slob. So I always feel like doing laps and pushups. Yeah, that was a definitely lucky break that I’ve leveraged ever since.

[0:11:39.6] RN: Cool. I think that’s an interesting topic is people that are just starting out that want to find mentors, right? It seems like in your case, you’re just reaching out, having zero experience. You were actually doing something and the mentor saw that at that time, right?

What would you say to somebody that hasn’t done really anything in business yet but still want that mentor, maybe they’re looking for a shortcut, they don’t realize they have to go tough work at first before they can get somebody to recognize them and be like, “Okay, this person’s serious,” right? Because they see a lot of tire kickers and people that want help but don’t necessarily want to do the work and go through it themselves first.

[0:12:13.8] JG: Yeah, so here’s five easy steps. No, I’m joking! I think there are a lot of factors. I am blessed to be on the other side of things now where people come to me for mentorship. I mean, the biggest thing, being on this side of things now is like, time is scarce obviously and people make this conception that A, if you talk to them conversational like young entrepreneurs or inspiring entrepreneurs, they put mentors on a pedestal now that like they get a mentor it’s go to like solve everything and everything’s going to change for them, which is far from the truth.

And then what...