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

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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!



Links Mentioned in Today’s Episode:

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


“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.”


[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.


[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.


[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 happens is they also reach out to somebody, and I get this emails all the time and Ryan Holiday has made some great blog posts about it where people just email them out of the blue and they’re like, “Hey, can you be my mentor?” And I think it was Tim Ferriss who said like, “That sounds like an unpaid — basically like unpaid job for me,” right? It’s a big word. So most of the mentors I’ve had in my life, we’d never use the word mentorship. It just happened organically like that and it took that role but we never said, “I’m going to check in with you every month and we’re going to do a three hour meeting.”

Some people have something setup like that. But you’re much more likely going to get a “no” if you come out of the gate and say like, “Hey, I would like to take three hours out of your month every — three hours our of your time every month to sit down and talk about my problems and those kinds of things.” So a lot of my mentorship stuff has happened organically and I think what has been the key to it is being very vulnerable and transparent with this individual as far as kind of where I am where I want to go and very clear on how they could help me and then also being very open to feedback because nothing is more detrimental than you want feedback but then you can’t take it.

[0:13:46.4] RN: Being unteachable.

[0:13:47.2] JG: Yeah, exactly, absolutely. And then you also have to take action. I think that’s out of respect as well is that even if you agree or don’t agree with what’s being said at least show that you considered it and I give clear reasons as to why you took action on it and the results you achieved, or why you didn’t take action on it. I think that’s one of the biggest things because, I mean, you don’t have to be like super successful or anything like that. But you do have to show that you’re worth investing in on some level.

[0:14:14.2] RN: Yeah, obviously, mentors help shorten the learning curve a little bit but there’s obviously still a ton of lows and highs on the entrepreneurship roller coaster. So with that said, what’s kind of the most painful part of being an entrepreneur to you, even though you have a successful business and it makes money and starting out, you’ve come a long way but it’s still painful I’m sure because I know for everybody I talk to, it’s painful.

[0:14:37.9] JG: Yeah, I mean, there are a lot of factors, there’s this fallacy that if you’re an entrepreneur you have all this freedom and all this kind of stuff, which is simply not true and actually, as time goes on, it looks more appealing to be in a corporate business or like in a cool tech company.

I have a friend of mine who sold his business for like five, six million or something like that and then went to go to work for Facebook and he’s like, “I enjoy it way more working at Facebook than I did as an entrepreneur.” And he’s been an entrepreneur all his life, but he’s like, “I get a steady paycheck, I have unlimited resources at my disposal to do whatever I want with my team within Facebook,” and it’s just like there’s no pressure whatsoever on that front.

He’s in a position where he’d be 1005 creative all the time. The biggest struggle for me with entrepreneurship, I mean because it changes daily, but I think the biggest one — and this is coming from somebody who now is in a good financial position. Add on top of that, the years of struggle we all face when it comes to financial component of it, it’s even more hard. But at this point, it’s really I still think like just the debilitating pressure of entrepreneurship every once in a while, that I’m feeling again right now. I’ve been, again, an entrepreneur for 13 years in this specific business since 2012, 2013, officially 2013 and it’s some of the pressures are still as debilitating as they were once.

[0:15:50.9] RN: Are they self-imposed?

[0:15:51.9] JG: Yeah, that’s a good point. Because some people don’t — I go through, the pressures I go through are the pressures of like wanting to deliver and over deliver and that’s because I care and there’s some people that go through, they sell widgets on Amazon and they could care less and it’s just a number game thing.

I guess that is something not totally unique to me but it’s not something seen across the board. But when you serve a group of people that you care about and you care about the product that you put out there, and your fulfillment that you get in the work, your almost legacy piece of like, if I die today, what will people remember me by? There’s just a tremendous amount of pressure from that. Again, it is self-inflicted but that’s the life I chose on some level.

[0:16:31.9] RN: Just to get a little bit more context for the audience. What is MastermindTalks, how did it start, where is it going?

[0:16:37.5] JG: Yeah, MastermindTalks is invite only event for entrepreneurs, to date we’ve had, since our inception in 2013, we’ve had just shy of 16,000 entrepreneurs apply for the event, which is capped at 150 people annually, which on paper gives it a harder acceptance rate than Harvard. Yeah, it’s just really an annual gathering of fascinating entrepreneurs from various different industries.

From traditional brick and mortar businesses, all the way to wearable technology and kind of everything in between, and business sizes from just shy of the million to 300 million and getting back to what I may had mentioned before, what makes this type of business difficult when you serve people you care about is we have a 150 people at a MastermindTalks, I’d easily have 125 of those people at my wedding. I mean, this is an example where we are right now, we’re at the Bahamas, which in theory, all of your clients but we’re on vacation with all of our families. Like 30 of us total, right?

So yeah, and then as far as where we’re going, usually when you have success in this industry, the common strategy to scale is more events or bigger events and neither of those things I want to do. Instead of scaling it in size every year, we’ve scaled it by reason cost of investment, specifically for new people coming in, also the calibre of people in attendance. That’s been our scaling strategy and sort of strategy in the future, but it’s very project based in the sense that I don’t have a 2018 plan.

That’s to our detriment on some level because yeah, when somebody’s like, “Oh, I can’t come to the MastermindTalks this year, but I’ll come next year,” I’m like, “There may not be a next year,” and I say that only because my last business, I was stuck on this hamster wheel where I built a business I hated to enable me to buy things I didn’t need to impress people I didn’t like. I just felt like I couldn’t get off and MastermindTalks is beautiful because it’s very project based. It’s five months of super hard, all consuming work, and then once it’s done you can kind of — you have space to reconsider, “Do we want to do this again? Do we feel like we can raise the bar again?”

Those kind of things so MastermindTalks Carmel is taking place in 69 days as 100% of my focus and then after that, I’ve like really nothing in my schedule. I have a trip to Italy with my wife and my daughter, but that’s pretty much it.

[0:18:35.9] RN: With that said, outside of MastermindTalks, is there anything else you’re working on business wise that fills up your time once the event’s done?

[0:18:42.7] JG: You know, it’s funny because I’ve thought about that a lot because I have definitely shiny object syndrome. Meaning like, again, MastermindTalks is beautiful, because it’s very project-based. It’s something I work on all year round, and again for me, I’m blessed to be in the position where the lines between friends and clients are blurred that when I’m spending times with friends like this, this is on some level business, it’s more…

[0:19:02.1] RN: Hanging out.

[0:19:03.2] JG: Yeah, it’s hanging out but it’s like, it helps me on the business side of things as well. So MastermindTalks on some level, is something I work on all year round. But really from a business perspective, it takes a good four, five months of hard, hard work, leaving a lot of space for the remainder of the year and when I get into those positions of space then I start to again, I get shiny object syndrome and I’m like, “I want to get into real estate, I almost opened a gym, I almost dropped like a million dollars to open a gym,” which is so fucking dumb, but I did it. Yeah, I was so close to — we were on lease negotiations and that’s where I fall apart.

[0:19:35.1] RN: Was this recent?

[0:19:36.3] JG: Yeah, we’re talking.

[0:19:37.5] RN: Because I think I saw you posting like updates on Facebook about like new projects you had your eye on, is that one of them?

[0:19:41.8] JG: Potentially. Yeah, then what happened was, gyms are terrible businesses but for me, it was like, I’m passionate about gyms. You couldn’t tell by looking at me, but I’ve been going to the gym on and off or had participated in martial arts for at least since I was 18 on some level.

I always love like the transformation because I’m struggled with weight my entire life and I’ve gone up and down and all that kind of stuff, I always like the transformation piece for people and what it can do and the ripples effect that if somebody gets in shape, it shows up in their relationship, it shows up how they are as a parent it shows up in their business, all that kind of stuff.

I was attracted to that idea, so it was very much a passion business for me more than anything, it was not like I’m going to get some gigantic return. But then I also thought about it when the deal was falling apart, I’m like, “Well I already have a passion business with MastermindTalks, can you have two passion businesses, because in theory, wouldn’t one take away from the other?”

Yeah, I mean, one thing I am definitely, I’m always interested in real estate and that’s something I’ve sat on the sidelines for a really long time. I wouldn’t say far too long, I had no money three years ago. I was beyond broke but now I have a little bit of cash and I really want to get into it, into real estate. So after MastermindTalks this year, it’s something I want to explore some more and I think that that would be a very good kind of marrying of — that would complete my year on some level where I could focus on MastermindTalks hard for a couple of months, focus on real estate for a little bit and real estate is not 100% passive, I don’t believe in anything that’s 100% passive. It is one of those things that once you set it up and you have your systems to place and all that kind of stuff, you buy a house and you’ve got property manager and all that kind of stuff, it does kind of keep going on its own, and it takes very little time investment afterwards.

So that’s kind of the plan for the future but then also really want to double down on — I hate to use the term “personal brand” stuff but coming out with another book late this year and coming out with the podcast again late this year. So those are some things I’m definitely kind of working on because I always constantly see the ripples effects of something like Ben who is our — I mean, he has an enormous platform. Any time the guys says anything, or somebody’s on his podcast, it’s huge.

That’s actually going to be a big relationship play for me on some levels that if I — the more influence I have, the more I could support people I care about. So if I have somebody coming out with a book, I can just tweet it like Tim Ferriss or something like that and if he tweets any book, it’s almost a bestseller at this point, right? To have that level of influence, it’s not even for me, like my own ego purposes. I actually don’t like being in the limelight on that scale. Being able to support friends of mine, I think it’s a really cool angle so that’s going to be a huge area of focus for me later on in the year.

[0:22:06.5] RN: Yeah, it’s really interesting way to look at actually scaling MastermindTalks where you’re actually not scaling the business but you’re scaling your support for the people that go, right? Which is, it’s cool. I haven’t looked at it that way. One of my favorite entrepreneurship stories and the one that I feel that really embodies the fail on mantra that we have here is the story you have about purchasing almost $84,000 worth of books from Tim Ferriss without having the money. Give us the backstory there and how you feel that this is actually a really risk averse play in reality.

[0:22:32.9] JG: I still have them, most of them. Anybody wants to buy 3,000 copies of Tim’s book, I got a good 3,000 copies left. Question was, how did it happen?

[0:22:43.0] RN: Yeah, what’s the back story?

[0:22:45.1] JG: Yeah, I guess really quickly, I didn’t enjoy my last business as I may have mentioned or as I eluded to earlier and ended up, when it was all said and done, a quarter of a million dollars of cash debt, didn’t know what I was going to do next. Somebody gave me a ticket to go see Seth Godin in New York because they had an extra ticket, I had no other obligations at the time so I decided to go.

Turns out, it was about the connection economy, how there’s huge value connecting likeminded individuals and I just felt very isolated as an entrepreneur. So I started this dinners called Mastermind Dinners where I connect entrepreneurs over dinner. The first one I did, I almost cancelled two hours prior because I’m like, “Nobody’s going to see value on this. They’re going to think I completely wasted their time.” But thankfully it turned out to be a great success. So I continue to do this dinners and I was paying for them out of pocket, didn’t have a business model behind it at all.

[0:23:27.4] RN: You didn’t have much money at this time right?

[0:23:28.7] JG: No, well I was considering bankruptcy within the like next month or two because I couldn’t make rent either. So I’m like…

[0:23:36.1] RN: What was your thought process there and dropping $600, $800,000 on a dinner?

[0:23:40.6] JG: Yeah, well so for me, I felt like the bank could take my car, they could take whatever measly assets I had left, but they couldn’t take my relationships or anything I invested in myself. So actually took $25k — I actually didn’t take $25k, I cobbled together like enough to like get me into the program and then spread out the rest like payments that I didn’t have money for and I’m like, “I’ll figure it out.” I joined Joe Polish’s $25k Group and that was in 2011, 2012.

[0:24:07.1] RN: Also when you didn’t have money?

[0:24:08.3] JG: Yeah.

[0:24:08.7] RN: Oh, so you’re just like, “I’m going all in. Who wants money?”

[0:24:11.2] JG: We were living on, I think I completely forgot about this, we were living on American express gift cards. Like living on them. Because my last business was great cash flow wise where you get a lot of points on our credit cards, so I’d cash those in for American express gift cards. We had something like $20,000 of gift cards that lasted us a good year.

We could only do groceries at somewhere that accepted these gift cards and it was the worst because you couldn’t transfer the balances so we’d have one gift card with like 48 cents and then another one with like a $1.30 and when we go to a store, we’d have to give them like six gift cards and be like, “This adds up.”

I completely forgot about this stuff until I found a gift card recently with a bunch of the numbers on the back of like the balances. I was like, “This has $22 left,” and it’s scratched out. Now it’s like, “It has $18 left.”

[0:24:56.0] RN: Those things aren’t like very easy to find the balance either. You have to either go online or call in, right? Such a pain.

[0:25:01.0] JG: It’s so archaic. You have to call in then type in the number and then wait for the prompts. It was bananas. When you have literally, I don’t know…

[0:25:07.7] RN: Just to find out you have 48 cents on the card.

[0:25:11.0] JG: I know, and then there’s other ones that you think are garbage and your check is like…

[0:25:13.7] RN: It’s the jackpot, right?

[0:25:14.7] JG: … you have $250 on this card. You’re like, “What? I almost threw this thing out.” So god knows if we still have balances out there. Yeah, anyways, was doing the dinners and I felt like the safest investment was in my network and in myself and then this was October in late November, Tim Ferriss ended up writing a blogpost and I knew Tim kind of vaguely at that point.

He had a blogpost called The All-You-Can-Eat Campaign of Goodness, which was his first book The 4-Hour Chef. That book was banned from all Barnes & Nobel bookstores pretty much all retail distribution before, like three weeks before it came out because he was the first author to publish through Amazon and Barnes & Nobel specifically want to make an example out of him because Amazon was just becoming this huge behemoth where it had a publishing armor, it also had retail and those kind of things.

So he ended up having these different packages, these vocal quarter packages where if you bought five books, you’d get additional resources. If you bought 50 books, maybe he’d do webinar with you. He had this hail Mary package if you bought 4,000 books, he’d do two speaking engagements. At the time, I was one of the first people to see his blogpost because I used to wake up at four in the morning and he just posted it.

I thought a friend of mine named Scott who does this big events in Canada and I said, “This is a great opportunity for him.” So I sent him an email, “You may want to check this out because you can,” — when he does events, he has two, 3,000 people show up at his events so he can easily move these books. I sent him the email, and the minute I clicked send I said, “You know what?This is a great opportunity for anyone because Tim’s never spoken in Canada and he doesn’t speak that much.” I’m like, “In the worst case, if I pull the trigger on this, I’m sure I can,” — I don’t know what his speaker fee is. That was the biggest unknown. I’ve never dealt with speakers before, I don’t know if a speaker like Tim charges $10,000 for a gig.

[0:27:44.6] RN: Is this a good deal, or?

[0:27:45.6] JG: Yeah, exactly. Or $100,000? I had no clue. I tried to do research, no luck. I ended up emailing Tim, I say, “You know what? I’ll take the package,” and he only was offering one, which is why it was time sensitive. Yeah, I emailed them, he was still awake and he’s like, “Yeah, no worries, we’ll talk more in the morning.” So I said, “Cool.” So I had to raise $84,000 pretty much within…

[0:27:06.6] RN: You had to pay before that actually happened?

[0:27:09.3] JG: Yeah. So what happened was, I think the blogpost came out on like the 27th or something like that or 21st and the book was coming out the following week like two weeks away but it had the order, it had to be placed within 72 hours or something like that. So I need the money like ASAP. But the one things was, I never raised money for any of my businesses in the past. I built them all on credit cards.

I mean, my eCommerce business, we were doing like $7 million dollars a year and it was all on credit cards. That was a tough thing because that was a limiting belief. I was just raised never ask anything from anyone. When I was a kid, I used to work with my father all the time, like evenings, weekends and like, it was like a landscaping business and people would come out outside because I’m like working in the scorching heat and I’m like seven.

They’d ask me like, “Do you want juice or water or something?” My dad would always tell me like, “Never accept anything.” But at this point I’m like, my back was against the wall. I’m like, “I got to get this money somehow and I’m not going to steal it, those days were over.” So I ended up reaching out to three friends, the first one said, “It sounds interesting, let’s talk numbers,” and I’m like, “I don’t think numbers like accounting perspective.”

I’m good at like big picture numbers, “Does this make sense, doesn’t it make sense?” And figure it out from there. But like nitty-gritty numbers, I’m not good at. Plus, I didn’t know the industry at all. I found out like, you know, 20 minutes ago that I was going to get into the speaking business I guess.

[0:28:26.5] RN: This guy is one of the pitch deck, right?

[0:28:27.7] JG: Exactly and I’m like, I’ve never done a pitch deck and I don’t know anything about this business at all. There is no business, I don’t even know what I’m going to do with this but I need the money. The second person said, and he was just a huge fan of mine and he’s like, “Listen, sounds cool to start a business together 50/50,” and I’m like, that sounds awesome, that’s better than what I thought I’d get on this call.” But I’m like, “I have one more person to call, let me call you back.”

Then the third person said, “Come pick up a check at my office tomorrow morning,” and didn’t ask any questions about the business, didn’t ask anything and I was not going to question it, I wasn’t going to be like, “Are you sure? Are you sure you don’t want a pitch deck?” I just went in and I’m like — the following day I picked up that check so fast. I think I was supposed to pick it up at like 9 AM, I was there at like 8 AM and I got that money and deposited it, sent the wire to Tim and bought the books.

The event, I parlayed that and it ended up becoming MastermindTalks, but a few months after the event, we never had an agreement in place as far as me paying it back or what that looked like, was he investing in a business or who knows? So I ended up reaching out to him and I said, “The biggest thing that’s on my mind, now that MastermindTalks was a success for a year one by event standards,” I’m like, “Why did you give me that money?” He’s like, “Well, I wasn’t really investing in the business, I was investing in you,” and that’s when two things became really clear: one is that you never know the value of your network until you really need it.

Two, when you hit rock bottom in life, and we all hit rock bottom at sometime, all you’ll be left with really is your word, the integrity of your word, and your peer group and your networking connections. So never tarnish your word and always invest in your network so that, yeah, that was a pretty kind of big moment for me. Again, getting back to strikes of luck, I think we all have lucked but looking back, I think that was definitely very lucky break. Because if it wasn’t for that investment, I definitely will not be doing MastermindTalks, that’s for sure. God knows what I’d be doing.

[0:30:07.6] RN: Be looking for more American Express gift cards.

[0:30:10.9] JG: Hopefully not. It was scary because also the one thing that I realized in that time period, I was so adverse to working for somebody else that I was almost ready to like live in a shelter.

[0:30:18.7] RN: Before you go get a job?

[0:30:19.7] JG: Before I get a job, yeah. Because at that point, I had already been an entrepreneur for like seven or eight years to go working for somebody else where I’m told when I can go for lunch and like, you know?

[0:30:30.0] RN: This would not make sense.

[0:30:31.5] JG: Oh god, I’d rather die, you know what I mean? That is such — I’m very freedom driven as most entrepreneurs are and to have to be told what to do on that kind of micro level just, I couldn’t bear it.

[0:30:42.6] RN: It’s an interesting thing because a lot of people that for me, like when I had a corporate job, right? I couldn’t get out of that situation and become an entrepreneur until the pain I had is like you are saying right now. Going to that job, it was so painful because I knew I had so much more in me that that’s the only way I could have ever broken off is if that pain was greater than me not fulfilling my potential.

[0:31:02.1] JG: Sure, most definitely.

[0:31:02.7] RN: Which it sounds like that was the case for you here.

[0:31:05.6] JG: Yeah, I just knew I was not going back to any, to working for anybody. Now I’m actually much more open to it only because the things like that are now more well versed as far as what’s out there and how you can still have freedom working for somebody else. Back then, that was not my mentality, back then it was like you’re either an entrepreneur or you’re chained down working for somebody else.

But again, now that I’ve had so many friends get acquired and work for businesses or do that transition and jump back between the two, it’s not something I’d be totally averse to. I just would have very kind of clear rules and those kind of things in place.

[0:31:36.2] RN: If you’re in that position to where you exit a company for five, six million and then you go work for Facebook, you could probably write your own ticket going to Facebook.

[0:31:43.3] JG: Oh yeah.

[0:31:43.7] RN: Set your own standards, be away from the office these months.

[0:31:47.8] JG: Yeah, I mean, there’s more freedom often times, you know? That’s the one thing, is this fallacy again about freedom but there’s two different types of freedom; there’s a freedom to do things and a freedom from the business to do things, right? A lot of people, they seek a position to get to do things so they need money. They get all this money but then they don’t have the freedom from the business to actually do those things, right?

They end up on their death bed, a slave to their business with all this money but they never had the freedom from the business to do it. So there are two kind of aspects of freedom that you need. Sometimes you can, again, achieve that working for a great company.

[0:32:16.8] RN: Which one would you say you value more? Would it be the financial side or the time side? Like taking it almost to an extreme where financially, you can’t afford any luxuries in life but you have your shelter covered, your food covered but you have the time to spend with Candice and Eva, your family, your friends?

[0:32:32.5] JG: I can’t acknowledge this guy really quickly because he is going to be I think another podcast guest. Ladies and gentleman this is Chris Plow who has his…

[0:32:38.8] RN: Chris Plow. Bright and early.

[0:32:40.8] JG: Yeah, hip in my face right now, which is not awkward at all.

[0:32:44.0] RN: No, it’s not as hip anymore.

[0:32:46.6] JG: I shouldn’t have got a such a low chair. Which one do I value more?

[0:32:49.2] RN: Yeah.

[0:32:49.7] JG: So I think I could lie and say I value the freedom from and I say lie because I think, what you truly value can show up in your calendar, right? I remember I used to say, “I put my family first,” and all this kind of stuff. Most people do. Or, “I put my spouse first,” and then I’m like, you look at your calendar, you really see what you value, right?

I have all my meetings scheduled and all the stuff blocked out and I have no time block with my wife or no date nights planned or no time blocked out with my daughter. I could say that stuff but do I really value it, right? I value again the from piece, I definitely do but where I know I’ve shown up in the last 13 years was more the freedom to do things, meaning, accumulating money so that I could do these things and then I would almost justify, I could do these things if I want to but I’m going to focus on making more money, right?

But I think I’m at a nice balance to at this point, I mean, I could do a lot of different things for the sake of scaling MastermindTalks, I could make a lot more money. We could easily have — we sold out last month and we were four months out at that point and I could have easily sold twice the amount of tickets and made three times the amount of money only because there’s a point where like, once the bare cost for the event are covered, anything else is 90% profit.

We could have made way more money doubling the size of the event but again, there’s that opportunity cost there that it just wouldn’t be as good. It would take a lot more work, we take the freedom from. I’ve been relatively disconnected during this trip, I would not be as disconnected if I had twice the amount of people to kind of cater to. So I think I’m at a point now where I’m starting to live that balance; money is definitely not everything at all. I could make more money selling widgets on Amazon but I want to do work that’s fulfilling. I want to have space and time in my schedule to do things that are of interest to me, or more importantly, even support people I care about.

That’s a huge kind of piece of my life is not just having open space in my calendar for myself but to support other people. So yeah, I think I’m getting close to living that balance but me of a couple of years ago was all focused on the freedom to do things, not necessarily freedom from and I was very much a slave to my business.

[0:34:51.0] RN: Got it. That’s an interesting perspective. Just to transition a little bit, so “Fail On” is the mantra we live by here with the idea being that if you’re not failing, you’re not growing. With that in mind, how do you force yourself currently to get out of your comfort zone, or do you?

[0:35:02.9] JG: First I think there’s this misconception about, I think failure is almost — this pendulum’s gone too much the other way. At least in tech. Fuck, I know, I don’t know if you can swear? Sorry about that but anyways. Just mark this episode…

[0:35:14.3] RN: I guess we can now.

[0:35:15.6] JG: Mark this episode as explicit and they’ll be fine.

[0:35:18.2] RN: It will give me more street cred. I like that.

[0:35:21.1] JG: I was getting on the whole fallacy of fear — or not fallacy, the misconception.

[0:35:25.5] RN: Getting out of your comfort zone.

[0:35:25.5] JG: Yeah, well just one thing about the whole failure. It’s almost celebrated and I think the pendulum before was like, “Don’t screw up,” or that kind of stuff and now it’s like to the point where it’s celebrated where these people in tech are taking $10 million dollars investment, losing it all and they’re like, “Yeah, whatever, it’s a failure one to the next one.” I’m like, “Dude, that’s not your money,” you know what I mean? That’s a big problem, right?

So I think in some environments, the pendulum is swung too much the other way. I mean, for me as far as getting outside my comfort zone, I think that I do things in my business that force me outside my comfort zone and force me from getting lazy. A couple of things, like one is feedback; I take feedback very seriously. We have a lot of different things implemented in the business to take feedback. I don’t even just take feedback, like I process feedback, which is huge and incredibly difficult.

Especially when you do work that you care about, people you care about, you figured out like it’s easy to live in your head and be like, “Oh we’re batting out a 100% all the time,” and all that kind of stuff but to actually take feedback is terrible. But, it keeps me outside of my comfort zone and keeps me kind of pushing and then there are things I do for using events as context, usually, 99.9% of events, they stay the same format every year, most of them just keep the same venue and once you have the model down, it’s just, it’s systems. If I do one event in our last one in Ojai, California, once that event was done, I could replicate that event.

[0:36:44.3] RN: New location, everything else kind of stays the same.

[0:36:46.6] JG: Same event, exact same event six months later with different group of people and 95% of the heavy lifting is done. But then you become, you get into autopilot and there’s no innovation that happens from that. For us, we pick our new venue every year, one of the core reasons is that it forces us to start from scratch. So it forces us to innovative forces us to be outside of our comfort zone so that when people like — I have friends of mine who have been in the event space for years and they are cool as a cucumber all the way up to the event.

Everything is done, dealt with, again, all their systems are in place, all the things in motion. I’m a wreck from this point forward, I’m an absolute wreck because there’s so many variables, there’s like, who knows what can happen? What happens if it rains, what happens if this venue sucks? What happens if the caterer does terrible food? There are so many variables but it pushes me outside my comfort zone every single time, which shows up in the fact that we have so many people that want to come back year over year.

My only real KPI that I monitor as well and the success of the event and the community is like, how many people are renewing? Gow many people want to come back year over year? Because most events, it’s like revolving door, it’s like pouring water in a strainer but there’s a great saying by John Paul DeJoria, “I don’t want to be in the order business, I want to be in the reorder business,” and that’s very much my view in philosophy.

The only reason like, somebody like somebody like Chris has been every single event that we’ve done, this is going to be his fifth event. Not too many people go to every single event or belong to a community for four plus years or those kind of things. We have a lot of those people and it’s only because, again, pushing myself outside of my comfort zone, and it sucks. It’s way easier to go on autopilot.

[0:38:14.7] RN: Systematize the business.

[0:38:15.8] JG: And systematize. 100%. But when you’re as successful is when you’re most vulnerable, you could tend to get sloppy and you can tend to get arrogant and I do, I have a few things in place that keep me pretty grounded.

[0:38:26.3] RN: You’re obviously for this, more quality than quantity in scale in MastermindTalks. How do you kind of raise the bar each year? Or do you even try or do you just try to make a new experience?

[0:38:35.6] JG: Oh no, I definitely try and that’s, again, one of the debilitating component because every time you raise the bar, you raise the expectation.

[0:38:42.6] RN: It’s going to be tougher each year after that, right?

[0:38:44.0] JG: It is never ending. I mean, the one thing is, and this is actually a nugget of wisdom somebody told me and this was after MastermindTalks year three, he asked me, “What’s your biggest struggle with MastermindTalks?” and I said specifically that, is that we raised the bar every year and we try really hard to do it. But every time we do it, it’s now just expected and how do you just stay on this like, this grind of always trying to raise the bar? Because eventually you’re going to slip on some level.

That’s my biggest fear is like slipping. That somebody says, “Last year was better than this year,” it’s going to break my heart, right? So what he said, it was like, “Well, instead of trying to raise the bar, why don’t you throw out the bar?” He didn’t mean much by it but the way I took it, it was like, “Well, why are we creating experiences that you couldn’t almost match apples to apples?”

[0:39:27.0] RN: To compare.

[0:39:27.1] JG: Yeah, exactly, compare. Our first two events took place at the exact same venue, right? So it was easy to compare the two.

[0:39:32.2] RN: Got it.

[0:39:32.9] JG: That one was better than the other and this was better this year and that was wrong that year and that kind of stuff. But I’m like, “If we change the venue every year, you still can’t compare on some level, but it also makes a significantly more difficult, it makes it a one off experience.” So that’s one of the components is that we change the venue every year, therefore it’s a different experience, therefore it’s hard to compare between past events.

Yeah, again getting back to a whole comfort zone thing, our format last year was, I surprised people with it. Last year we sold out a good three months in advance without announcing any speaker or any agenda and when people got there, our model up to that point is like a TED Talk for entrepreneurs. We’d have 15 talks during an event. Our model last year when people got there I said, “Hey, I actually, full transparency, I’ve completely forgot that we changed the format,” and we didn’t tell anybody in the sense of like I changed this format in my head nine months ago not realizing that…

[0:40:24.7] RN: No one else knew.

[0:40:25.7] JG: I didn’t tell the attendees that this was the new format. So I was terrified but basically we said that we were actually shifting to a peer-to-peer model where we have virtually no speaker and that was getting out of my comfort zone. I mean people spend whatever, eight grand to be there, the travel if they’re Canadians like $13 grand to announce that, “Hey we are actually changing the format and we don’t know how this is going to go. We think it’s going to go well but we’re not a 100% sure, we don’t know. We have never done this before and nobody really does events like this,” and some people were uncertain.

As soon as I announced it I was watching. I was being super careful and cautious of people’s facial reactions and that kind of stuff. I had a few friends of mine come out to me afterwards and they weren’t a 100% bought in but I’m like, “Judge it when it’s all said and done,” and when it was all said and done, overwhelmingly it was the most positive event we’ve ever done. Our NPS score and I know we calculate it wrong because in theory it would be a 10 out of 10 but I don’t believe in that. On a scale of one to 10 if you are not familiar with NPS it’s you ask the question, “Would you refer our product or service to a friend?” Basically.

[0:41:21.1] RN: This is Net Promoter Score?

[0:41:22.9] JG: Yes, exactly yeah and if it’s like six or seven then they could go and you’re probably lose them as a client in the long term and they’re an eight or a nine or a 10, they’re like an Evangelist or those kinds of things. Out of a 138 people I think who submitted the survey last year, which was like 80% of our audience our score was 9.77 out of 10, which was like tremendous. But it was only because we took that risk outside of our comfort zone and we pushed ourselves every year.

So I think that is a common theme and then why I’ve probably started this podcasting like the amount of stress that you put on yourself too, can be debilitating is because I live outside of my comfort zone every year for this event on some level. Because if I systematized it and did it for the sake of scaling and all that kind of stuff, it would be much more — yeah there weren’t be much pressure around it but I always try to push myself outside my comfort zone because that’s been the key to our success and then the people who come to our event, again, because I care about them so much, that’s what they deserve.

[0:42:19.2] RN: Yeah, I mean, on that note what’s one directive or action item that you would give someone that has a burning desire to create a better life but aren’t necessarily sure of where to start, what business to start, or what their idea might be?

[0:42:30.6] JG: Yeah, well I will steal a saying from somebody who is on this trip, and that’s Phil McKernan that, in the absence of clarity take action. The whole reason the Tim Ferriss thing worked, the buying of the books, was that I had known from my previous life in entrepreneurship that every time I threw a hail Mary, which is like football terms. I didn’t realize not everybody knows what a hail Mary is. Soo it’s a football term where…

[0:42:51.9] RN: Phil McKernan would know.

[0:42:52.9] JG: Exactly, where someone who runs like a thousand yards and you throw a ball and you don’t know if it’s going to work at all but you just throw it out there and cross your fingers. Every time I threw a hail Mary in my last business, I always find a way to make it work. Every months, the only reason we were able to grow faster than our competitors, I put half a million dollars in transactions on my credit card, on my Amex and had to pay it back in 21 days with zero dollars in my bank account. You know, doing that month over month over the years I’m like, “I will find a way to make things work.”

[0:43:19.2] RN: You build that muscle, right?

[0:43:20.1] JG: Yeah and then the Tim Ferriss thing, I never thought it would be in the event space. I mean I saw the blog post and I am like, “I’ll do it. Like it make sense and I know worst case scenario I could potentially sell off the books and get some money back or some speaking engagements and get some money back.” But I think, yeah the taking action component is huge and then also Steve Jobs has a saying that you can’t connect the dots looking forward, you just have to trust that they somehow connect in the future.

You can’t steer a parked car, right? So you have to take action, you have to move forward and one of the biggest things now, look like self-actualization, is everybody is trying to like — all our basic needs are met, right? 99.9% of us have shelter, food, all those kinds of things so we are moving up Maslows Hierarchy of Needs and we are asking ourselves like, “Will I be remembered? Why am I here? What’s the meaning of my life? What’s my purpose?” and those kinds of things.

To me a lot of those purpose or meaning, I don’t even know if I am living my “purpose” per se and don’t get me started on just that whole way of thinking like it would be ignorant for me to think that I am going to be doing MastermindTalks for the rest of my life. I know I’m at my core I’ll be 00 MastermindTalks at its core, I surround myself with people I care about and supporting them. I will be doing that for sure for the rest of my life but it may take shape in different ways in the future.

[0:44:28.6] RN: You find out what’s important to you, right? And then you follow that path. Like for you it seems like supporting people, that’s who you are to the core.

[0:44:34.4] JG: Most definitely, yeah. But it is also like I think of it almost like an onion, right? That you constantly are peeling away layers and getting to what that true essence of who you are is and I feel like I am just much closer to it than I was before and I feel like on some level, I’m at it but I’m probably not. I am 32. Again, because five years ago I never thought I’d be doing what I’m doing. 10 years ago, God who knows the direction I thought I’d…

[0:44:59.4] RN: And if you are just starting out, I know I felt like this maybe you did as well? Is that your first business, you think this is going to be the only business you do your whole life.

[0:45:06.6] JG: Sure, exactly, yeah. I know.

[0:45:07.2] RN: “This is going to be the last business ever.” Yeah it’s crazy to think that but for whatever reason I think everybody feels that way at the beginning.

[0:45:13.9] JG: Oh yeah. Oh absolutely, and you should because then on some level because then you’ll really double down on it because if you look at things, “Oh, this is only going to be a year or something,” potentially you can take shortcuts, right? So if you do have that long term thinking you’re probably going to make better decisions for the long term.

[0:45:29.2] RN: I just think people sometimes get paralyzed by the fact that they think that this is going to be their only business.

[0:45:34.1] JG: That is actually a good point, yeah.

[0:45:34.9] RN: So they really get paralyzed by it not being the right one or maybe this isn’t it. So I think with anything there’s a balance where you just have to start taking action, like you said with your quote, versus not taking shortcuts but also still taking it very seriously.

[0:45:49.0] JG: Yeah, no I think that’s the biggest thing because people just simply don’t take it. My brother and I are polar opposites and that’s because he takes no chances, no risks. 28 still lives at home. I was out of the house when I was 17, you know what I mean? So we’re very polar opposites in that sense. But, again, I’d never thought I’d be where I am, in the industry that I am and the business I am. But that Tim Ferriss thing, I notice that like when I was spiraling out of control on some level, it was a long time — I became trigger shy and I stopped taking risks and when that Tim Ferriss thing came along I’m like, “This is another hail Mary. This is a Hail Mary that I could take.” Yeah that was an action I took and it led me to this. So those small little actions just keep moving. That’s the biggest thing is when you stop just like when you work out, right? You’re off for two to three weeks or you’re on vacation.

[0:46:31.1] RN: So hard to get started.

[0:46:32.5] JG: It’s brutal, right? But once you get going you get momentum and I remember when I was getting back into the gym after a long, long time, like building habits like you want to start very small, right? I remember I institutionalized like, “I am only going to the gym for the first month for 10 minutes,” which makes no sense. But it was such a short period of time that I had no reason not to go. I could be like, “Oh I don’t have 10 minutes,” you know what I mean? So again, starting small and taking action I think are two of the biggest steps.

[0:46:57.8] RN: If you have to pinpoint one person who’s had the most profound impact in your life and what do they teach you?

[0:47:02.6] JG: You.

[0:47:04.5] RN: Awh, that’s so kind.

[0:47:05.6] JG: About good looks. This is also your first in person podcast?

[0:47:08.8] RN: Oh this is actually.

[0:47:09.8] JG: There you go.

[0:47:10.4] RN: Most of them are Skype Audio.

[0:47:11.9] JG: Blamo, see? You’re beautiful. So one person I’ve learned the most from?

[0:47:15.7] RN: Yeah, that’s had the single most profound impact on you with where you are at today.

[0:47:19.1] JG: Tough question, only because, again, I look at some people who’ve had big impacts and we talked about two of them early on and if it wasn’t for those — you look at the profound impact overtime, if it wasn’t for those two little small investments they made.

[0:47:30.7] RN: Ripples.

[0:47:32.7] JG: Yeah exactly, I wouldn’t be where I am. So it’s hard enough not to acknowledge those folks. I think overall and I don’t want to name drop or anything like that, but I think Tim Ferriss has had a huge — I don’t think, I know he’s had a huge impact on my life only because in 2011, I came across the book 4-Hour Work Week in 2008, read the book and I was like, “Oh this is interesting.”

Then there’s a story in there about, I think it was called, From Fables to Fortune. It was about this MBA guy and this Mexican, there’s just great story and it actually fundamentally shifted the way I looked at life on some level. Because the essence of the story was that this MBA guy stumbled across this Mexican fisherman, and he said, “What are you up to today?” And he said, “Oh, I’m going to go fishing and then I’m going to go siesta with my family.”

[0:47:10.7] RN: Oh I know this one.

[0:47:11.7] JG: And the guy is like, “Oh, well you should get more fishing boats and build a fishery,” and all this kinds of stuff and basically go through this entire story and then to the end, end up with life he already has and that’s the mistake a lot of us make and that was a really impactful story for me and I got that from The 4-Hour Work Week.

In 2011, Tim did an event called Opening the Kimono, which was geared towards authors who wanted to become a New York Time’s bestselling authors. I saw him come out with this event and I never had the intention of ever becoming an author but it was $10,000 to go for two days. $10,000 at that time was a piss ton of money. It was 20 times more than I ever paid for an event but I’m like, “At $10 grand there is probably going to be some interesting people there,” and that fundamentally shifted the way I’ve viewed value being surrounded by people who are one or two steps ahead. I mean that’s where I met Ramit Sethi, Lewis Howes, Ryan Holiday, Robert Greene, like just a slew of just amazing folks.

[0:48:58.8] RN: Did you maintain relationships from that event?

[0:49:00.7] JG: Oh yeah, all of them. As many as I could, Joey Colt, I met Chris Plow.

[0:49:05.6] RN: Yeah, he was just telling me that.

[0:49:06.4] JG: I met Chris at Opening the Kimono, I met Joey Coleman. These are two of my favorite people. Ryan Holiday, is again, one of my favorite people. So that happened in 2011 and then 2012 was when I bought the books. If it wasn’t for him I wouldn’t have MastermindTalks be a success. I mean there is no two ways about it. It’s been good and I’ve had put friends on his podcast and that’s helped them tremendously with their books and it’s helped him as well on some level. So he’s definitely had the most profound impact over the long term than anybody else. How’s that for a name drop? Blamo!

[0:49:34.0] RN: Well drop the mike.

[0:49:36.1] JG: Yeah Richard Branson and I we go way back.

[0:49:39.9] RN: Oh that’s amazing. So obviously MastermindTalks is coming up in 69 days, what are you most excited about leading up towards that and then we’ll wrap this baby up.

[0:49:47.9] JG: I’m not excited.

[0:49:49.8] RN: Well you’re going to be a mess from all the stress.

[0:49:51.2] JG: I’m excited once it is all said and done.

[0:49:53.1] RN: Okay, so you’ll be excited 72 days from now.

[0:49:55.4] JG: Yeah, I mean I just want it to be a success, obviously, and not a success — a success by like just people’s experience and how they feel during the experience and that’s tough. It’s tough because then also I’m not binary. It’s not like I am selling something, double your business and then you can like see it, right? You are dealing with people’s emotions and whether they feel like this year is better than last year and who knows? Maybe they are going through a divorce and this is going to impact their experience and no matter how great the experience is they’re not going to enjoy it.

Yeah, but I am also terrible at celebrating. Even when the event is done I’m like, “It could have been better and next year will even be better,” you know what I mean? So there’s never really a point where I am like, “Oh, we hit it out of the park.” I am getting better but by most people’s standards I am terrible at celebrating and most entrepreneurs I know are terrible at it as well, which I think on some level helps us with the goal setting because we set these lofty goals and achieve them and we’re like, “Yeah, it wasn’t big enough. I wasn’t thinking big enough, I’m going to move the goal post again.”

But it’s weird because I have all of this pressure. I did a speaking engagement recently and I put all this pressure on me before I get onto the stage. I drill a talk 50 times. I’m like, “Oh this is going to suck, blah, blah, blah,” and then I get on stage and then I just make it work and then it turns out that version on the stage often times is better than any version I practiced. The same thing with MastermindTalks, I put all this pressure I think of every single worst case scenario, I play the event in my head over and over, and over again and then when I get on stage and everybody is in the room I’m like, “I feel at home.”

[0:51:15.7] RN: Oh, nice.

[0:51:16.7] JG: Yeah. There’s nothing —

[0:47:17.7] RN: Finally a sense of peace and like, it’s here?

[0:51:20.0] JG: Yeah and especially when everybody is in the room because actually nothing sucks the wind out of my sails more than when we have cancellations. Because, again, these are some of my favorite people on the planet, I’m looking forward to seeing them, I have their experienced planned in my head and I’m like, “Oh I can’t wait for him to see this person, or sit them next to that person,” and when they can’t come for any reason, which there’s not that many people who cancel obviously the last minute, but it happens.

[0:51:41.2] RN: For people who don’t know, the details that go into your events are insanity.

[0:51:41.2] JG: Yeah.

[0:51:45.1] RN: I know you take a ton of pride in that stuff so down to the details of who’s sitting with who, where everything is strategic and everything you lay out for the event, which is unlike any other event. So just so the audience has some context there.

[0:51:57.6] JG: Yeah, it’s very high touch in that nature and because of that, all of the variables leading up to it are scary but then when I step on stage I know that it’s real and I know what I have to work with is right in front of me. I have those specific people and now it’s go time. So I started to actually somewhat enjoy myself at the event and then the final dinner is when that I am on cloud nine. That’s usually 99% of the event has been executed has gone well. We have one percent left probably not going to screw it up at this point now I can start enjoying myself.

[0:52:25.2] RN: Everybody’s had their few drinks at the bar and there’s less stress.

[0:52:29.0] JG: Yeah, so that’s the plan. I’m excited about it.

[0:52:31.4] RN: tTat’s awesome man. I am going to wrap it up there, but thanks for taking the time out on the middle of vacation in the Bahamas, I really appreciate it.

[0:52:35.6] JG: No worries, it’s windy and it looks a little stormy but it will clear up. So thank you for waking up so early.

[0:52:40.8] RN: Love it. All right thanks Jayson.

[0:52:42.2] JG: All right dude.


[0:52:46.1] RN: You can find Jayson at jaysongaignard.com and you can also connect to Jayson on Twitter. He’s @jaysongaignard on Twitter. That spelling along with the links and resources Jayson and I discussed, including more information on his book, podcast, and events can be found at the page created especially for this episode, you’ll find that all at failon.com/001.

Finally, as I’m creating this project for the simple goal of getting people to take action through embracing failure, if you could do one thing to support my mission I would greatly appreciate it. If you’d just be so kind to rate and review the podcast, I would be ever so grateful. This will actually help the podcast be visible to more people and if you feel it deserves a five star rating and you leave a review I’ll be sure and mention you by name in an upcoming episode as just a small way to say thanks. To rate and review the podcast you can simply go to failon.com/itunes or failon.com/stitcher.


[0:52:46.1] ANNOUNCER: That’s all for this episode of The Fail On Podcast. For more resources, show notes and action items to help you find success in your failures, sign up for our mailing list at failon.com.

For more actionable inspiration, we’ll catch you next time right here on The Fail On Podcast.


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