Get Comfortable Being Uncomfortable With Clay Hebert

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Clay Hebert is a crowdfunding genius, a marketing strategist and the creator of the Six-Word Intro. As one of the world’s leading crowd funding experts, Clay has helped over 150 entrepreneurs, and raised over $50 million dollars on Kickstarter and Indiegogo.

Clay has trained senior leaders at fortune 500 companies, with clients like Accenture, Pfizer, Zappos and some of the top universities & nonprofits in the world. He advises corporations and startups on strategy, marketing, innovation and culture.

We’ll be discussing how Clay was able to transition to entrepreneurship after nine years of management consulting in the corporate world. He’ll be sharing how to make important life decisions based on your future calendar, not your best idea. And how to get comfortable with getting uncomfortable and lastly, why failure is just an opportunity.


Key Points From This Episode:

  • Selling candy bars in the cold: Clay’s first marketing scam.
  • Why success and failure are both imposters.
  • The media’s role in building you up to tear you down.
  • Why Clay grew up playing it safe in the job market.
  • Joining Seth Godin’s MBA Programme.
  • Clay’s 10 magic marketing questions.
  • Hear more about Clay’s failed startups.
  • Clay’s advice for taking the leap and quitting your job.
  • Working backwards from our calendar.
  • Why there is no perfect idea.
  • Envisioning your first 10 customers.
  • Getting comfortable with getting uncomfortable.
  • Good crowd funding is good marketing.
  • Creating the win-win: Help them help you.
  • Documenting your failures.
  • And much more!

















Links Mentioned in Today’s Episode:

Fail On Website –

Fail On Podcast –

UnboundMerino – (Promo Code: FAIL ON)

Clay Hebert on Twitter –

Clay Hebert on LinkedIn –

Crowdfunding Hacks –

The Perfect Intro by Clay Hebert –

Purple Cow by Seth Godin –

Yeti Coolers –

The War of Art by Steven Pressfield –

Chris Sacca —

Seth Godin’s Alt MBA Course –

Kitty-O –

Indiegogo –

Kickstarter —

U-2-Me —

Creative Live —

Transcript Below

Read Full Transcript


“CH: As you know, most startups never get to 10 customers. That’s where it all went. In this idea phase and this testing and whatever. You can remove a lot of the difficulty and concern and risk because everyone’s closing their eyes, thinking they’re going to build the next big thing. Just trick yourself and say you’re trying to build a 10 customer company, you’re trying to get 10 customers. You can envision your 10 customers having thanksgiving dinner with you.”


[0:00:29.3] 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.


[0:00:55.5] RN: Hey there and welcome to the show that believes failing in a hyper focused way is the only way to achieve your dreams. in a world that only likes to share successes, we dissect the struggle by talking to honest and vulnerable entrepreneurs and this is a platform for their stories.

Today’s story is of Clay Hebert. Clay is a crowd funding genius, a marketing strategist and the creator of the Six-Word Intro. As one of the world’s leading crowd funding experts, Clay has helped over 150 entrepreneurs, raised over 50 million dollars on Kickstarter and Indiegogo. Clay’s trained senior leaders at fortune 500 companies and his speaking clients have included Accenture, Pfizer, Zap Post and just some of the top universities to non profits in the world. He advices corporations and startups on strategy, marketing, innovation and culture.

He’s just a really smart guy and really well liked by pretty much everyone. We’ll be discussing how Clay was able to transition to entrepreneurship after nine years of management consulting in the corporate world. He’ll be sharing how to make important life decisions based on your future calendar and not your best idea. And a simple focus strategy based on factors of 10 to build your customer base and business, and how Clay would start a brand-new business today with limited funds and resources.

But first, I have a lot of travel coming up and luckily, all I need to travel with is a backpack for one reason only, it’s a shirt from a beautiful Toronto company called Unbound Marino. They have clothes and apparel made out of marino wool and get this, you can wear it for months without ever needing to have it washed. You probably should have it washed, but you could do it.

Talk about a traveler’s absolute dream. You would never check a bag again, it just really cuts down on everything you need to take when you go on travel, vacation or holidays. Check in at the show notes page for an exclusive Fail On discount that you won’t get anywhere else. And, if you’d like to stay up to date on all the Fail On podcast interviews and key takeaway’s from each guest, simply go to and signup for our newsletter at the bottom of the page. That’s


[0:02:59.2] RN: Hey there and welcome to the Fail On podcast. Today, I am sitting down with Clay Hebert. Clay helps people fund their dreams, he’s helped over 150 entrepreneurs and creatives, raised over $50 million dollars on platforms such as Indiegogo and Kickstarter.

Clay, welcome to the Fail On podcast.

[0:03:16.0] CH: Dude, thanks so much for having me, I’m stoked to be here.

[0:03:19.0] RN: Just for a little context, we are in San Diego right now in a co-working space called Downtown Works. They’ve actually got a little studio room, we’re just holed up in here, having a conversation.

[0:03:29.7] CH: Love it.

[0:03:32.0] RN: Obviously I want to go into crowd funding hacks and everything you’re doing in that realm and obviously some of your current projects. But I’d love for you to take us back to really the first time that somebody actually gave you money in exchange for a product or service that you created?

[0:03:45.1] CH: Yeah, absolutely. I remember it well, I was freezing my butt off, maybe this doesn’t count because I didn’t create the candy bars but this was in elementary school when they gave you the candy bars to go sell. I was determined to win that alarm clock you know?

Looking back, it was probably $10 or $15 alarm clock, so I could have just gotten there a lot easier but I sold like seven boxes of candy bars. So I’d go to the local grocery store, middle of winter in Wisconsin, we go there at night, after school, after practice, it’s dark, it’s cold, bundled up. Asking, you know, costing every person who comes in the door in the grocery store if they want to buy a candy bar and it was really my first marketing lesson.

I didn’t know all the words and hadn’t read all the books at the time about permission and human spam and all that stuff. But what I did figure out is, they weren’t buying the candy bar. They were not the kind of person who supports a little kid who is freezing his ass off who’s selling the candy bar. I went from my first marketing lesson to my first marketing tactic/scam/whatever.

I brought a duffle bag of my brother’s clothes and I would wait, I would sell, I would sell candy bars for two hours or until frostbite set in. I realized that on any given night, after a certain number of people who were the kind of people who bought a candy bar, like I said, none of them were interested in the actual chocolate, overpriced candy bar. There were just like, here’s this kid.

When about four or five of them would go in, in the span of you know, before they came out. I would run around the corner, change clothes, change into my brother’s clothes, go stand at the other exit door and wait for those people to leave the grocery store and hit them up again. They would buy on the way out, again, not because they wanted the candy bar. But because here’s this sad little kid selling candy bars for school. That was the first marketing lesson and first marketing sort of tactic.

[0:05:35.0] RN: Just for context, where was that? Because you said frostbite.

[0:05:37.6] CH: Yeah, small town, Eau Claire Wisconsin, I grew up in a town, not tiny town but 60,000 people, west central Wisconsin called Eau Claire. It was Kermes grocery store in Eau Claire Wisconsin, I was probably about seven years old.

[0:05:49.4] RN: That’s amazing. Just in terms of obviously this is the Fail On podcast and you learned your lessons early on selling candy bars. It’s actually funny because I totally forgot, I did the same stuff, right? The same – I don’t know what it is, I think it’s mainly for sports teams, not for school. But that was typically what it was and you’d sell yeah, like you said this oversized candy bars that were like $5 apiece.

Like go in the grocery store and get it for like 50 cents.

[0:06:13.8] CH: Exactly. Yeah, not the best place to obviously, you know, they’re overpriced, they’re about to walk in to a place like you said, go to a place. I saw a story last year that I thought was hilarious, maybe it was a couple of years ago, this girl scout, you know, girl scout cookies were just sold in their annual drive. This girl scout just blew all the records, all the sales records or whatever because she sat up outside of a legal dispensary.

[0:06:37.7] RN: Amazing.

[0:06:38.2] CH: People going in, buying their marijuana, they walk outside and there’s this cute girl with a cart table and of course, she just blew out the sales records. So another marketing lesson, you know? Context and place matters.

[0:06:48.0] RN: Maybe we should be studying from kids?

[0:06:49.8] CH: I know, right?

[0:06:50.4] RN: They know how to pull the heart strings.

[0:06:51.9] CH: That’s’ right.

[0:06:53.8] RN: How do you actually view success and failure?

[0:06:56.0] CH: Interestingly, so I see them as inextricably linked. You cannot have success without many failures. Failure’s are sort of like the bricks, you have to stand on them to reach success. There’s a poem I love, I’m not a huge poetry guy, I’m kind of trying to read some more and figure out if I like it. But there’s one that I absolutely love called ‘If’ by Rudyard Kipling. In there, there’s a line about success and failure and he talks about treating those two imposters just the same. I love that line because in our world, especially now with all the entrepreneur porn that’s out there and you know, all the Shark Tank.

All the stuff about you know, celebrating people, over-celebrating people’s successes and over destroying people’s failures. That simple line from an old poem about success and failure are both imposters, meaning, if you succeed, it doesn’t mean you’re the greatest thing since sliced bread. If you fail, it doesn’t mean you’re a horrible person.

I think there’s such a stigma attached to failure and that’s why this podcast exist, that’s why you’re doing this to help lift that but yeah. It all comes back to the media because the media loves to celebrate, well, they love to build you up so that they can tear you down, right? That’s what gets clicks, it’s a click based media business model. You know, you’re a sports guy, I’m a sports guy.

I think it’s fascinating. I grew up watching Michael Jordan, I was younger but you know, watching him succeed and win his championships. He was you know, by far the most popular sports player on the planet. Now, if you look, the most liked athlete and the most hated athlete are the same person and it’s Lebron James.

That’s not because of Lebron James. If you compare Lebron James to Michael Jordan, kind of from an off the court perspective, Lebron’s a saint, right? He hasn’t done anything.

[0:08:54.8] RN: Great family guy.

[0:08:54.9] CH: Family guy. Never at the club, never DUI, nothing, he’s squeaky clean. Lebron’s the worst thing he ever did, was not even that he went to Miami, just the way he announced it and it still raised a ton of money for Boys and Girls Club.

The media loves to build you up and tear you down and just the fact that Lebron is the most loved and the most hated at the same time, that tells you all you need to know. Because it’s kind of like you know, all the success in the world and they’re just looking, needling for things. But yeah, to remove the stigma of failure, actually…

[0:09:30.3] RN: Just one point though, why do you think that is with the Lebron specifically? Because like, I was obviously younger but I remember watching Michael Jordan play and by far my favorite athlete to watch, other than Tiger Woods. I don’t remember that stigma with Michael Jordan. People nit picking at him and what he did wrong.

[0:09:47.5] CH: No, there wasn’t, that’s exactly my point. Back then, there were just fewer media channels and not everyone could have a blog, not everyone could Tweet their opinions.

[0:09:56.5] RN: Now, everybody has a voice, everybody has opinion.

[0:10:00.1] CH: Yeah, if you decide you don’t like Lebron, you can have your platform and it’s good that those gate keepers are gone. But the click view based media who – you know, you’ve probably seen in our entrepreneurial world, there’s lots of people trying to start, they know that the news tends to be generally negative, right? If it bleeds, it leads, right? Old school journalism, saying, there’s lots of people in this world trying to start newspapers of only good news and only, “Look at this great thing that’s happening.”

I’ve just got to shake my head. It’s sad, it’s unfortunate but those are never going to you know, compete against the big media, the click bait, Up Worthy, Buzz Feed and these click things. It’s just literally trash. Can you ever remember a list that all that changed your life, you know? They get the most likes and the most shares but you know, “10 Chrome Plugins that blah, blah, blah” that nobody ever remembers. Man, “What’s the one thing that changed your life?” “Well, there was this Buzz Feed list article…”

[0:10:55.6] RN: Never happens. Take us back, obviously selling candy bars. Take us through the journey of where you kind of came up and entered entrepreneurship for the first time. Outside of obviously the small scale stuff as a kid?

[0:11:08.1] CH: Yeah, for sure. It was interesting for me because we watched my dad, I had two brothers in the middle, we’re all three years apart. We watched my dad, my dad was an entrepreneur, he owned a furniture store in Eau Claire Wisconsin. You know, nobody had ever taught him about business. He was an engineer by trade so he knew really well about the engineer and how the pieces fit together and all that stuff. But not about sales and marketing.

He was naturally a good kind of sales guy and customer service guy. Me and my two brothers saw him be an entrepreneur and over years, that business didn’t work. It sort of failed slowly over a lot of years, had a lot of overhead and things like that. As we were watching this, you know, we sort of, you know how observant kids are.

We were basically like, okay, dad is really smart, dad is really hard working and the entrepreneurship thing didn’t work, therefore, we’re not going to be entrepreneurs. Even in junior high, we kind of had this – we’re going to go seek out the safe stable, long term job. So all three of us did.

Went to college. I went to Accenture right out of college, big – largest consulting firm in the world. I think nowadays they employ over 400,000 people which is a nation, not a company. Yeah, I remember it was 1999. I just started Accenture. I kind of looked around and I asked my partner that I worked with, I said, “You know how much do the partners make?” He’s like, “The new partner makes like 1.2 million.”

Now, I just mentioned Michael Jordan. Scotty Pippen was kind of my favorite player growing up because I just had to choose somebody other than Jordan. The only person I knew who had a decimal in their salary was Scotty Pippen. I didn’t know anyone personally who made something point something a year. Then I said, “How long is it to make partner.?” He said, “About you know, 12 to13 years.”

So I spent the next six months or a year looking around. I’m like, “These guys aren’t that smart, they’re not that – like in 12 years, I should be able to be doing what they’re doing.” Mentally, I had hunkered down, it wasn’t like I was like, “I’m staying. I’m riding this horse as long as they’ll have me, I’m going for the brass ring and doing that.” So I stayed and then over that period of time, a lot of things changed, the company went public and the salary for partner went down.

The difficulty to making partner went up. In the 2008, beginning of 2009, I was living out here in San Diego and I was trying to look for a different path out of the big corporate. I was almost partner but that’s not the life I wanted. I knew a lot of people that were wealthy and unhappy and I had read Seth Godin’s stuff back in 2003, 2004, read Purple Cow, Down The Rabbit Hole. Started doing that nights and weekends and so at the end of 2008, Seth blogged about an opportunity to study with him. So I applied and I was fortunate and got in his MBA program, first time he ever done it in New York. I quit my job at Accenture.

[0:13:49.2] RN: How many years had you been at Accenture at that point?

[0:13:51.9] CH: Nine.

[0:13:53.5] RN: Okay, so you were there for a while?

[0:13:55.2] CH: Yeah, I was almost partner. The next promotion was partner, that’s probably about a year for making partner and so it was tough. Even though, you know, I’ve been reading about this other world that I was so excited to join. We still get told so much from society about get the safe, stable job, do everything, do everything. I literally saw my friends a few years ahead of me who made partner, traveling on the road.

Super stressed, unhealthy, getting divorced, hating their lives and it’s like, your bank account is not worth that. But it was hard because I couldn’t actually – I’ve told many people this. I applied to be Director of Marketing at Callaway Golf out here in San Diego in 2008. But rightfully, they said, “Dude, you have no marketing experience. You’re a management consultant. You’re an eccentric guy. What have you done for marketing?”

I couldn’t say, “Well I read all the right books and blogs,” right? Escaping that world and going to study with Seth was just a once in a lifetime experience and getting to learn from him and keep in touch with him and continuing to learn it from him, it has been amazing.

Then after that, I hung out of shingle and started to help in. Initially, individuals and authors with marketing and medium sized companies and then fortune 500 companies.

[0:15:01.5] RN: Just based on the knowledge that you got from working with Seth and obviously reading the books and educating yourself, that was enough to say okay, “Now I’m going to actually work with these successful people, these successful authors and actually handle their marketing.”

[0:15:13.5] CH: Yeah, exactly. As far as handle it, I always stayed away from – because I just came from like I said, the biggest consulting and agency work is the same kind of thing you know? You have an army of doers and you build a client X and you pay them .5 X, is kind of the model.

I just came from the largest version of that ever. I didn’t want to build. In 2009, right after the Seth program, I could have built a 20-person digital, social marketing agency pretty easily in New York. That was the last thing I wanted to do. I wanted to stay on the strategy side, do speaking, do workshops, teach a man to fish because I really believe conceptually as well.

Same with crowd funding, same with marketing that they should do it themselves. You know, I can come in and teach them how to do it but I really think like, you can’t hire someone to do your sit ups for you and you shouldn’t hire someone to do your marketing for you.

[0:15:58.6] RN: Right. That’s a good point and like – because I went to this stage probably two years ago where my business was starting to make a lot of money. I’m like, I want to start a different company, a skin care company at the time. I’m just going to hire all these people to handle all the stuff that I don’t want to deal with, without trying to dig in and learn it myself first.

I was trying to hire all these experts, come in, create the sales letter for me, blew 50k, didn’t do one sale.

[0:16:26.2] CH: Wow.

[0:16:26.3] RN: Didn’t do one sale. It’s a very valuable lesson to teach a man to fish because I would have been way better off and more educated on how to actually find that expert, if I had dug in and known what to look for on – you know, if I’m even going the right direction.

[0:16:41.7] CH: Yeah, exactly. It’s so much about marketing is, it’s fundamental, it hasn’t changed. We humans, the way we think about this, it’s not like the tools are new but the tools are the tail at the end of the dog, you got to understand the whole strategy, everyone’s like, well… Basically, if you don’t have a rock solid fundamental good marketing strategy, Snap Chat’s not going to save you, Facebook ads is not going to save you.

I think, there are tactics that may or may not work. But if you don’t even know why they work, flowing from a really solid strategy. That’s what I teach companies in going for a day for a workshop or whatever. It has this framework, I call it 10 magic marketing questions and how will they hear about you, doesn’t come until question number eight.

There’s seven questions before that of foundation. What’s the story we’re telling, who’s the customer, what do they already believed is our story that we’re telling? One of my favorite brand stories is Yeti Coolers. It’s a cooler, it keeps your food cold and that’s been around forever and it’s been a commodity product. Like if there would have been a business school challenge or some entrepreneurial challenge like eight years ago.

You need to start half billion dollar cooler company, that would be super hard because it’s commodity product, right? But they built a brand and they hung stories around it like “Hey, it’s grizzly proof and it’s this and it’s that.” They really came out of nowhere in the last eight years and they’re going to be billion-dollar companies selling essentially a commodity product. Because of the ability of branding and marketing.

[0:17:57.2] RN: Yeah, it’s nuts. After leaving Seth’s program, going into, actually starting services and products for people. What was one of those first failures or you’re like, should I actually be doing this? Did you run into that? Kind of the imposter syndrome at all or what were those initial struggles starting out?

[0:18:17.3] CH: Yeah, the first one was probably right before I left Accenture and went to the Seth program. I was really trying to hustle this stuff nights and weekends on the side. A friend/colleague from one of the software vendors who worked with that Accenture and I.

He was also in the startups and technology and stuff like that. We built a failed startup called Bloggley. The concept was, these small-ish bloggers don’t have enough pay trees to attract legit banner ads and advertisers and things like that. But, if we build a network of blogs, right? Then we can – and this was before a lot of the blog networks were really big.

We were distributed, we both had our day jobs which we’re taking up, you know, it’s Accenture so it’s like 55 hours a week. So it was really truly a part time thing. We both threw a little bit of money into some development. Really had no clue what we were doing, didn’t know anything about – Eric’s recent startup hadn’t come along so I didn’t know about custom development, validation testing, all that stuff.

We were really just – we had no clue what we were doing. It was absolute failure, we didn’t have one customer, we didn’t have a functioning product. We had a concept and a dream and it was all exciting and there was enough entrepreneur stuff out there at the time that we were both really excited. You know, dreams of cashing big checks or whatever but we had no clue, we didn’t…

Then, a couple of years later, I met Dan Martel and he taught me about – got me Down The Rabbit Hole, lean startup and Eric raised a customer development and landing pages and validation and testing and talking to your customers. That just totally flipped my world around. But yeah, the Bloggley was an ultimate failure.

[0:19:55.2] RN: You looked back after talking to Dan and getting more knowledge of “What was I doing back then?”

[0:19:59.1] CH: Absolutely, it was brutal. I realized how much I didn’t know but you know, you’ve got to learn what you don’t know. Yeah.

[0:20:06.7] RN: So for somebody that’s – because I think it’s an interesting point, right? Where you decided to leave Accenture and actually make the leap. Because I think there’s a lot of people out there that are probably in a comfy corporate job, making good money, maybe going for partner, same thing. But they have the itch and they know they want to do their own thing but they’re just scared.

They don’t know how to start it, they don’t’ know how to make that leap or if they even should. How did you get to the point, obviously, I think you’re probably making good money with Accenture at that time, right? That far in. You probably had reserves and what not.

Did you choose to leave Accenture after you already had something working and going? Or was it just a burn the ships, “I don’t care how I’m going to do it but I’m going to do it.”

[0:20:49.4] CH: Yeah, it’s a really good question. The way the timing worked was, I had been talking about Seth Godin inside of Accenture for years I was trying to beat the drum and say “Hey, this innovative thinking that we’ve been talking about.”

When I applied and I got into his program, I looked at my options. I said, instead of burning the ships, “Do I have any other options?” One of the options is you can take a six-months leave of absence. You know, for no reason, you’re still an employee, you’re still in the system, you just don’t get a pay check.

I did that for the six months of the Seth program. I did a leave of absence and then even after the Seth program and after spending that much time, you know. Looking back, it seems silly to me that it was a hard decision but at the time, you know, like I said, there’s so much societal pressure of “What are you, crazy?”

That’s funny, the span of people’s opinions. Good friends who knew me well and had heard me talking about, wow, what amazing opportunity, that’s like you know, if Steve Jobs said “You want to come hack in my basement for six months?” That’s amazing.

[0:21:40.6] RN: You’re courageous and bold and good for you for going for it.

[0:21:43.4] CH: What an opportunity, right? They knew who he was in that world and other people were like “Well, it’s not in accredited program and it’s not – what are you doing throwing away this almost partner career to go –“ literally one person said, “To go do an unpaid internship with this bald guy in New York?” That was the praise and it’s interesting because it just shows, you know, the span of sort of world view of the people and you know, both people, both sides, they thought they had my best interest in mind, right?

The people on the latter people, even though they were totally off the mark thought they we redoing the best thing for me, right? They’re at the safe, stable job because that’s what they’ve been taught as well. I forget the question.

[0:22:21.4] RN: I guess, what would you say to somebody that’s in that position that you were at at Accenture. That they know they want to do something, maybe they don’t know what but what would you – what kind of advice would you give them based on what you went through?

[0:22:33.4] CH: Two things. One, what really helped me in the moment is, I sat down with a friend and when I was really after the Seth program was going to cut the cord, burn the ships like you said, send Accenture the email that said I’m not coming back. I’m starting my own thing, I’m starting from scratch, zero clients, zero revenues or all insurance, just starting.

One of my friends said, “You know, you clearly obviously really want to do this so what’s holding you back?” I talked to him about it and he said one simple thing that just changed everything. Like lifted the stress and the freedom, he said, “Well do you think they would take you back, they said you put in nine and a half good years at Accenture, if you left to go try this entrepreneurial thing and it doesn’t work and burns your savings and you can’t get a customer, worst case scenario, then you go back to Accenture and say, ‘Can I get hired at the level I was at when I left?’”

“Do you think they would take you back?” I said “Yeah, of course, absolutely.” “What’s the risk then?” They essentially removed all the risk just by that simple thing of saying, would they take you back. Now, nowadays with the economy, with the way things are going, I don’t think that’s necessarily the case for everyone but it’s worth exploring. The other big thing is, make the leap not a leap. Imagine the visual of a leap. Let’s say, you’re standing on a box at your cross fit.

It’s you know, 50 feet in the air and you’re jumping off of it, that’s a leap you might twist your ankle, it might break your leg, hurt your back, whatever. Well, if you can make the box lower or you can make the floor higher, well now, it’s not such a big deal. So we have these tables right here. You and I wouldn’t be scared to jump off this table under this floor. If there’s going to be no injury that’s going to happen, we know how to do that.

Well what if you can build it up so that it’s even? It’s even and you can just step from one or the other or step off a curb. My advice to anyone thinking about, “Wow, should I do it, should I make the leap?” et cetera. If you are telling yourself that you can’t build up the side hustle, nights and weekends, you’re lying to yourself. You’re hiding by being scared, by not building up your thing.

Now, with what we know about lean startup and landing pages and testing and validation and getting your idea out there, talking to customers. There’s all these ways, you know, do your day job, don’t – here’s my advice. Don’t quit your day job until you’ve completely validated your side hustle. Maybe, when you’re making more from your side hustle than you are from your day job, right?

Let’s just say, round numbers, you make $50 grand in your day job. Don’t quit your day job until your side hustle is bringing in $25,000 or same as your salary, right? Because as you know, between nights, weekends, everything else. If you can’t validate it to someone, if you can’t bring in some level of money, dedicating nights and weekends, it’s a bad idea and you shouldn’t quit your job anyway and you should move on to idea number two.

[0:25:09.4] RN: Right, what makes you think you’re going to be able to you know, just have those daytime hours to actually make it work, if you can make it work in the off hours?

[0:25:16.0] CH: Yeah, absolutely.

[0:25:16.8] RN: Got it. That was obviously your first failure with Bloggley. What’s been really like the most painful failure though? The one where it was like hurting your stomach and you didn’t know how you’d ever be able to recover from it?

[0:25:31.1] CH: Yeah, I think, I try to build a technology startup a few years ago called Spindos. I got the business model completely wrong. I did some things well, it was essentially the original vision was video speed networking for the fortune 500. I left Accenture – this massive, huge company. I realized I knew about a hundred people.

You and I meet a hundred people at a conference. I’m like, how is it after a decade at this massive firm, I only knew a hundred people? There’s no – in these massive corporations, there’s no great way to discover. You and I could work literally in the san Diego office of Accenture and if you’re in government and I’m in healthcare, we’d never meet each other.

Even if we had a millions interest in common. I built this thing that was video speed networking for companies. But I followed the Dan Martel, Eric Reese, Lean startup advice – built the screens, didn’t build any codes, stitched it together, you know, prototype, et cetera and showed it to all these companies and it was interesting, I was about 80% wrong with the vision of what they actually wanted. They didn’t care about video speed networking, they did care about discovering who their colleagues are.

Google for colleagues. Searching inside is interesting. Who in the Chicago office plays golf and knows marketing? That they loved. But, the biggest mistake or failure was not realizing that if that was the kind of company I wanted to build, it had to look like Slack. I had to go raise a bunch of money, go full boar, hire hundreds of people and build a real enterprise sales company.

I thought I could do that in this kind of lifestyle, bootstrap, sassed three employees kind of deal and it didn’t work. At the time, I was also sort of becoming the marketing and crowd funding guy and it was tough because again, I had a sit down, it was a different friend but a sit down conversation with a different friend. He said something and said well, “Either one’s going to be successful, you just have to choose which one you’re going to build.”

He goes, “Even though Spindos looks good and you’re getting some good validation. If you choose that, the next 10 years of your life looks like this. If you choose to be the crowd funding guy, the marketing expert and the strategist, the lone wolf, you know, speaking in workshops and stuff, then your life looks like this, which one do you want?”

It was really hard because I was again so excited about that idea about building that kind of company. I was really excited about selling it and connecting the people, building something that would be on the cover of magazines and like finally – somebody built Google for colleagues, right? Finding all the connections in these big companies, it’s a problem that still hasn’t been solved.You know? But, that was –

[0:28:07.6] RN: It didn’t align with what your life, what you wanted your life to look like.

[0:28:11.6] CH: Yeah, exactly. Nowadays, when I coach entrepreneurs and a bunch of other people, I talk to them and I say, “Don’t choose it based on whether you think it’s going to be successful.” We make so many decisions all the time in our world about, is it going to work? Should I do this kind of podcast? What should the name be?

Choose it based on what you want your calendar to look like. You’re kind of excited, you’re smiling here right now and you have multiple interviews lined up today and you’re cranking them out today and this is a good day for you. You’re in the studio, you’re loving it and so your day, your calendar looks good and your week and your month and your year. That’s one thing I talk to people about. What the perfect calendar is. Tell me what you want your year to look like and let’s reverse engineer that.

Assuming the business is going to be successful because what was it, just last week or whatever. Another 50-million dollar net worth and committed suicide because he was just unhappy, stress, New York City. He was like walking through central park with Henry Paulson. We have a pile of studies of examples like that of people with the millions and millions who are ridiculously unhappy. I say, work backwards from the calendar.

[0:29:16.6] RN: Is your greatest lesson in that failure, just actually defining what you want, before you start building something?

[0:29:22.4] CH: Yeah, exactly. That’s right. If I would have, in the very beginning I love the quote, “Fall in love with the problem, not your version of the solution.” But if I was really, truly honest with myself and said, to do this right, it’s going to look like Sales Force or Yammer or Slack or one of these big enterprise companies.

Otherwise, don’t start, alright? There’s another great book by Seth called The Dip which is all about quitting early. Have that discussion, have that coffee discussion and then decide if that’s what you’re going to go on. But when you go, go all in, right? I’m a poker player and when you go on, you push all your chips in the middle and you either win or you lose.

I was spinning too many plates and it’s a problem that I still have. It’s something I still struggle with is because of the way my mind works, because of the way I think about marketing and startups and everything else, we joke about Dave Asprey, Ben Greenfield and the orange goggles. I go through the world with marketing goggles on of everything that’s broken. I want to fix it. And what opportunity that would be and now that I know what it takes, or doesn’t take, to spin up a startup or something like that. Everything is just popping, as in like opportunities, to do things.

One of my biggest focuses and failures and things and not very good at on a day to day basis is tuning out all that noise and just looking down at the one project that I have to ship and I have to finish. I love the book The War of Art by Steven Pressfield where he really personifies the resistance and one of them is you know, you get to mile 22 of the marathon you know?

A marathon’s great because there’s rails and there’s people going and pressuring and you’re on that path.

[0:30:53.9] RN: Water breaks and.

[0:30:54.5] CH: Yeah. But my marathon all the time is like it’s mile 22 and then I’m like, squirrel, new project, new thing, new talk.

[0:31:01.4] RN: That’s a great book by the way. For somebody, I think you have the opposite problem, maybe, maybe not of a lot of people that are trying to get started. Whereas you see opportunity in almost everything because you noticed a problem, you probably built that muscle after a while.

I think a lot of people are, they might get a lot of ideas but they’re looking for that perfect idea, right? I got to have this perfect idea if I’m going to quit my job and start a business and that’s obviously a huge fallacy, right? It doesn’t exist, it’s perfect business. What’s the first business? Let’s start there.

For somebody that knows they want to make the leap but they don’t know what business to start or what it might be. What advice would you give to that person to actually discover how to start a business or what idea to go with?

[0:31:48.3] CH: Yeah, it’s a great question, you’re 100% right. There is no perfect idea and in fact, it’s become a very good litmus test for me over the years because I’ve now dealt with a lot really successful entrepreneurs and a lot of really rookie entrepreneurs and everyone in between.

The more value they place on the initial idea before they have a customer, before they have revenue, before they have anything. The more rookie the entrepreneur is, right? “Clay, will you sign this NDA before I ask you some –“ “No, I’m helping you for free or whatever. You know, I’m not going to sign your NDA because we’re not going to protect your shitty little idea.”

You know, ideas. Ideas are basically worthless. Everyone’s like, yeah, my uncle had the idea for Facebook before. Yeah, well, he didn’t do it, you know? Maybe he did have the idea, great. He can email mark and say, thanks for building my idea but you know, ideas are not going to put a putter in the hole. Ideas get glorified. Again back to the whole media thing we love talking about.

Because looking backwards, you know, hind sight, it’s easy to say, “Oh I had that brilliant idea.” You want to hear a crazy, shitty idea? “Let’s throw mattresses down on our floor and let strangers stay in our home, right?” Nobody knows, air in Air BNB stands for air mattress, as in throw it on the floor of your living room and let people crash.

That’s how Airbnb got started. Looking backwards, it’s a great idea in the moment, insane and major super smart people like Chris Sacca, you know, VC investor and everything. He looked at that and he was like, that’s an insane idea, people are going to get killed and you know, that’s the worst idea I’ve ever heard. It’s Air BNB. The value of an idea, the advice I would give is, one, 10, 100, 1,000. One, get your first customer, your first none friend or family member giving you ideally money but at the very least, their email address to follow up to hear more.

To even get to that point, you have to be able to effectively articulate what’s the problem, what’s the solution, how are you going to solve their problem, do they even have that problem? Do they have that problem and they know they have that problem because some people have problems but they don’t know they have that problem, right?

Seth always used to say, “Count how many miracles it has to take.” If in your business plan, you’re explaining a whole thing to me and there’s four steps, we’re like, then miracle happens and then — Being honest with yourself. But, one, 10. Then you have one, then can you get to 10? Can you get to 10 customers? Which is a huge milestone. Every company that’s successful – Air BNB, Dropbox, Evernote, they all at one point had one customer and they all at one point had 10 customers.

As you know, most startups never get to 10 customers. That’s where it all went. In this idea phase, in this testing and whatever. You can remove a lot of the difficulty and concern and risk because everyone’s closing their eyes thinking they’re going to build the next big thing. Just trick yourself and say you’re trying to build a 10-customer company. You’re trying to get 10 customers. You can envision your 10 customers having thanksgiving dinner with you, right? 10 people that are paying you money.

That is such a massive milestone for most startups and once you have 10, if they all bring 10, now you have a hundred and you’re off to the races, right? Are your customers telling their friends, telling their customers?

Because the reason we buy things is because of the stories we tell ourselves about who we are, right? Again, Seth has this great rift called, “people like us do things like this.” I think that’s marketing boiled down to just a few words, right? Yeti Coolers, right? Most people don’t buy you Yeti Coolers? But the people that do, people like us do things like this meaning we have a Yeti Cooler, we don’t have a Coleman cooler from Walmart, right? Brands and Christian Louboutin, red sole shoes, you know, that is marketing.

If your customers are not bringing in other customers, you won’t grow. None of us, not the biggest companies in the world have enough marketing funds to reach everyone individually if the story doesn’t spread. Be honest with yourself about how the story spreads.

For an entrepreneur, out there who is thinking about starting an idea. Just literally, just one and 10, get one customer that’s paying you money, one stranger, not your mom and then 10. Once you get to 10, then figure out how to get the story to spread to get to a hundred and if you get a hundred, email Rob. You win.

[0:35:57.7] RN: No, I love that. It’s super simple, right? It’s a good way to start but how do you, how would somebody assess risk on that? Or how would you assess risk on that. In terms of getting that first customer. Getting to 10 because if you get to 10, like you said, you might have something. Do the people need to sink 5,000, $10,000 into building something?

[0:36:17.0] CH: No, $0. Your only risk is a little bit of time and then your ego.

[0:36:21.7] RN: Can you just turn this to hypothetical, let’s say, I don’t know, in your business, right? You're starting from scratch, you have the – you know, you don’t have the skills or knowledge you have but you have 500 bucks, a thousand bucks to get started. How would you use zero dollars to actually build something? To get 10 customers?

[0:36:40.6] CH: Absolutely. Let’s say, you’re building a product for moms and it’s really cool new thing to help them with their strollers or something with their kids. Some physical product to help moms with their kids. I would take the $100, I would go to Starbucks and buy $25 gift cards at Starbucks. Then I would sit there with my laptop or my iPad or my prototype and you got to have a visual of it. Maybe you take another $100 and go on online and find one of these sites and have a cad person draw up beautiful visual of the thing.

Hit a little bit of hustle, a little bit spam maybe. You can, or find – you know, women in central park or who have strollers who are watching their kids or whatever and just be like “Hey, could I buy your coffee for just a minute of advice, just a quick reaction?” Half of them will say yes, hit them with a $5 Starbucks gift card and I just bought their coffee and show them the 3D rendering of your thing and be like, “I’m not even going to tell you what it is, what it does. What do you think? What’s your reaction, right?”

Test, validate. I used to mentor for Startup Weekend in New York and it was funny, my main job was to – in lean startup they call it GOOB, Get Out Of The Building. Because these developers and coders, right? They think in java script and they can do amazing billion things with code. When you’re a hammer, everything looks like a nail, when you’re a developer, the solution to everything looks like code. My job was to literally throw them out of the building, out of the Microsoft offices into central park and say, “Go talk. Go find your customers. I want you to come back with five emails of people who want this thing.”

Yeah, the money, it’s not about the money. It’s about, can you get 50 emails and then can you ask those people, “If I built this, would you be interested.” That’s where crowd funding like – crowd funding can bring the cost of failure to zero. Now, the platform is not going to magically bring you all to people. You have to build the landing page, build the stuff but yeah. I would effectively explain the problem and the solution.

[0:38:39.9] RN: I think that’s another issue for people, like we talked about, you want the magic five step process on how to do this and then you’ll have a business, right? Which doesn’t exist.

I think people struggle with the idea of you, actually have to go hustle a little bit. You have to get out. Because for a lot of people, talking to five people at Starbucks or 10 people at Starbucks is out of their comfort zone.

[0:38:59.1] CH: Yeah, that’s exactly right.

[0:39:00.3] RN: You have to talk to people, you have to – I mean, that’s – I think before you do anything, you have to get comfortable getting uncomfortable doing stuff that you don’t typically do. Because if you want a business that you don’t have, you have to do things that you don’t currently do.

[0:39:14.5] CH: Exactly, you nailed it. Getting comfortable, getting uncomfortable is exactly it. That’s why you know, there is all these health benefits of cold showers and ice baths and all those other stuff. The actual health benefits, yeah, whatever. There’s some.

[0:39:28.7] RN: The biggest benefit is mental of –

[0:39:30.6] CH: If I can sit in an ice bath, or if I can take a cold shower. Wouldn’t it be much more comfortable to take a hot shower? Then I can do things that are uncomfortable which is I can go make five sales calls. I can go test my sales script or I can hire a coach to get better at that thing, right?

We don’t hire personal trainers because we don’t know how to do an arm curl, we hire personal trainer to make us show up. So the next place I might spend some of that, you know, $5,000 is on someone to teach seals or book you know. I’d spend $0 on a library card or the internet, Google, Yelp U-2-Me or not Yelp, U-2-Me and Creative Live, all these courses. There is nothing you can’t learn for free on YouTube and if you pay a little bit of money, Creative Live and U-2-Me are one of these we’ll package it for you in a beautiful thing. Seth’s current online program called the Alt MBA, he took what we did in 2009 in person in six months and he spent years figuring out how to affectively package that online and the result is just brilliant.

It’s a month-long course, literary with the goal of exactly what you just said which is getting comfortable, being uncomfortable so every 48 hours, you are publishing a blog post to your peers and to the system and about a topic. So it’s not even about learning the concepts. You do learn a lot of concepts around some constant sorts of stuff but the point of the MBA is not learning the content. He knows you can learn the content anywhere you can Google anything.

It’s nobody who goes through that program currently ships a blog post every 48 hours every month and if you go through that program you do.

[0:40:57.5] RN: So yeah, that’s cool. I didn’t realize that’s how the programmed worked. So it’s more just to push people out to their comfort zone to ship stuff, get it out there into the world?

[0:41:05.6] CH: Yeah, I mean there is structure curriculum and it’s big and there’s group projects and everything else but the outcome is not, “I learned these 12 topics because you can go on HBR.” You can go on Google and learn all those topics anyway. I mean when I think about when I went through the education system versus what’s available today. I spent 12 weeks in a management accounting class that I never used again.

What a waste of 12 weeks in my life right. Now, you can just pick a thing and you say if it’s important to learn financial statements or to do this to run your startup you can do that. Then if you need to go deep, you can go deep but more likely you just probably need to hire the right person. If you are the founder, you probably shouldn’t be also doing the accounting.

[0:41:49.1] RN: Totally, so you talked a little bit about the crowd funding stuff you do and you’ve helped people to raise a ton of money. Well over $50 million at this point right. So how do you get into that world and how did you – I guess take us to the first campaign you worked on and how that push you to continue doing it?

[0:42:05.3] CH: Yeah, absolutely. I was in Hawaii and the phone rang. It was a friend of a recent client, this was a couple of years after I left the Seth Program. I’d helped Sebastian Younger the author with his book launch and his website and stuff like that. A friend of his PR person reached out and he said, “My Kickstarter is live, it’s failing. I heard you know the internet.” Like this woman, a great lady but she had an AOL email address.

I was not a crowd funding expert at the time but I knew marketing and I knew online marketing and social media and so she reached out. It was a real tear jerker of a film. It’s called Gold Star Children, you know children who have lost parents at war is that term. So the Kickstarter was about a documentary film she was making and she needed about 20 or $30,000 for post-production. So I watched that and then helped her promote that campaign in the right military communities.

Because who cares about Gold Star Children, the documentary? It’s military families. Promoted it there. It helped her get funded. Next week I was playing basketball with a friend of mine and he mentioned a friend who was doing a Kickstarter, helped him. Really just on project became two, five, 10, 100, 150 and then it pretty much became the crowd funding guy. But it’s all – because good crowd funding is just good marketing right?

Pricing, scarcity, storytelling, urgency, all that stuff. All the levers that good marketers know how to turn are there on a crowd funding page and campaign.

[0:43:29.6] RN: So just high level. If I have a new product I am wanting to launch and I wanted to go crowd funding, what is the process you’d walk me through?

[0:43:39.0] CH: Yeah find the people that care. I always say that I have good news and bad news, but the bad news is good news, the bad news is 99.9% of people don’t care about your crowd funding thing and what you’re building. So immediately that means don’t worry about big press, New York, don’t try to reach everybody. Anybody who talks in eyeballs and impressions just run the other way. Back to our one, 10, 100, 1,000 most successful crowd funding projects have a thousand backers or less.

And so think of bottom up not top down, think of finding the people who care and going from there. So I have this good example, there is a product named Kitty-O. It was a tower, a device that you put at your house and it allowed you to – I came up with a tagline for it. “Play with your cat even when you are not home.” So it’s a tower, it’s got a camera, it’s got a laser, it’s got a treat dispenser. It looks like a robotic kind of lava lamp thing.

When the guy came to me, he showed me the high-end 3D rendering of it. It looked beautiful. I said, “Yeah, this is the kind of thing that could succeed a Kickstarter really well if you do the marketing right” I said, “How many emails do you have?” and he looked at me funny and he said, “Two” I was like, “Two? Did this guy just launched his landing page this morning? What’s going on?” I was like, “What do you mean two?” and he said, “Well I use one for work and one for personal.”

I was like, “No, how many emails to you” oh, okay pause, back up, rewind the tape and he didn’t direct marketing or anything. So he was where you’re at. So he was a phenomenal student. He built a landing page, the first version was terrible. So we iterated on the landing page and I’d break all of this down. If you Google “ultimate crowd funding landing page” or I think even just “crowd funding landing page”, it usually comes at number one but we went through all of the iterations and built the page.

And then when we promoted it in the right places like little niche sites like, it converted it 40%. So four out of 10 people who hit that page saw the product, completely understood how the product worked. It was fully explained and a handful of people raised their hand, four out of 10 people said, “I want to know when this thing launches.” Over six months, he gathered 13,000 pre-launched opt in emails of people who saw his thing.

And then when he launched he was fully funded in 36 minutes, 200% funded in the first day and raised $270,000.

[0:45:51.4] RN: So are you spending a lot of paid traffic to this? You’re doing a lot of paid marketing?

[0:45:54.9] CH: You know paid is one tactic and you can. He certainly tried different things and paid is one. To me paid is a shortcut to – if you don’t have five years to build up trust and permission and things like that. Then paid is a way to find this people but paid in a very focused manner. So he was on The View with Whoopi Goldberg which is more like PR. It didn’t move the needle at all. It didn’t matter, huge eyeballs because one, nobody wakes up in the morning and is like, “I’m going to turn on Whoopi and I hope today she tells me about a weird cat toy.”

But House Panther, the tagline for this is called “House Panther is the premier online magazine for design conscious cat people.” It’s designed within reach for cat freaks. So get super specific and then once you find those little pockets where it’s 99% of the people. Sure then if you want to run Facebook ads to fans of House Panther, you know you’re reaching the right people.

So paid is one way. There’s SEO, there’s organic, there’s blogging. There’s everything else. It all just depends on the mix of how much time you have, what kind of company you’re trying to build. Are you trying to build a content company or are you trying to –

[0:46:58.5] RN: With House Panther for example, are you buying banner ads or what are you doing actually on House Panther?

[0:47:02.6] CH: No, not banner ads. So this is what I call “Play with their rules.” We looked at House Panther and we said, “What do they do?” Every month, House Panther does a product giveaway. Enter your email to win a chance at winning this product. So we slid into their content calendar. That is the biggest thing. So that is a really important point, it’s subtle but it’s important. When you want someone else to talk about you, play the game with their rules.

So House Panther’s rules where every month we do a product giveaway. That means there’s somebody’s job at house panther to run the editorial calendar and have a giveaway every month. So then Kitty-O showing up and saying, “We would just like to be your November giveaway. How do we make that happen?” Now you are doing them a favor versus tugging on their sleeve and saying, “Please write about us.” Another example is I worked with an iPad cooking app called Pana.

I won’t go into a long story but essentially it was a cooking app where the best chefs in the world, Mario Vitali and stuff, would cook their famous recipes on video with the recipe right next to it and the actual chef cooking the thing. This guy David honored this whole thing. So I told them, “Well you’ve got to get food bloggers but there’s a million food bloggers. You’ve got to go get food bloggers to write about this thing because it’s a gorgeous app, beautiful, all these big chefs are involved.”

But you’ve got to design the win-win, you just don’t go to these food bloggers and say, “Please write about my thing” that’s selfish. You go to them and you say, “How do you create the win-win?” Well the win-win is, food bloggers wake up with two problems. They need content for their audience and they need something interesting to talk about. They need content and something valuable for their audience. So you show up on their doorstep and you say:

“First of all, what do you think about this app? It’s gorgeous, it’s awesome right? Yeah, you agree?” cool. “Secondly, I’m going to give you lifetime subscription of this. It’s normally 15 bucks a month. You get it for free for life if you blog about it and if you want to blog about it, I’ll give you a lifetime subscription to give away to your audience.” So now these 500 food bloggers instead of again pulling on their sleeve and saying, “Hey please write about my thing” which is the worst.

Now you’re saying, “You get one for life and you get one to give away” so now you just solve a problem they have which is they don’t know what to write about today. They get to write about it and they get to look like the hero giving away lifetime subscription and they can run the contest however they want. You multiply that by 500 food blogs and you are home free. So that’s one simple example. He didn’t have time to architect all of that but I handed him that tactic. So the point is create the win-win and play by their rules.

[0:49:27.9] RN: It’s interesting because a lot of people – and I love hearing that because it’s such a – like you said it is very subtle. A lot of the marketing tactics as you know have over the past five, 10 years have been very like disruptive based right? Interruption you know. Like flashing banner ads to get your attention and all of that stuff. So I love the fact that you are thinking about how can I solve their problem today which will in turn help me?

[0:49:51.1] CH: Yeah. That entire industry of banner ads and everything, there is an entire Madison Avenue and New York and ad tech industry, it’s all bullshit. It’s all complete bullshit. It’s impressions and clicks and the people who run those industries, they don’t even want to know how well that marketing is working because it’s not, right? It’s all the real other tactical stuff that is strategic. Trust and permission and all of that other stuff – that is really building the brands nowadays.

It’s about what I call portable stories, what are the stories, how people are talking about your product when you are not in the room. That’s what made Yeti a half billion dollar cooler companies because they’re like, “Hey my cooler is grizzly proof, is yours?” That’s the conversation that’s happening and yeah, they put out a YouTube video that shows a Grizzly trying to break into a Yeti. Dozens of YouTube videos right? They didn’t do banner ads to say, “Buy the Grizzly-proof cooler.”

Nobody parrots your tagline. Nobody says like, “Oh you use a Mac too, doesn’t it help you think different Rob?” Nobody says that right? But you have to know what are they saying about your company when you are not in the room. If you don’t know those porthole stories, banner ads are not going to save you.

[0:50:49.9] RN: So true. I think there’s a big shift going away from that because like you said, it’s all kind of bullshit and it’s going to more storytelling and value-based marketing right?

[0:51:00.0] CH: Yeah, it’s all storytelling and again, it comes down to excessive – like that people I guess do things like this. Even right outside the store. There are restaurants that you and I would never eat at that other people do eat at right? So find your people, there’s a great Timothy Leery quote, “Find the others” and that there’s a lot of marketing wisdom in that. Just find the others and ignore everyone else and when you start getting into the worlds of banner ads and mass media buying and everything else.

You are literary saying, “I’m too lazy to even think about who my customers are. I’m just going to blast everyone and it doesn’t work.”

[0:51:32.0] RN: Yep, so we talked a little bit about getting outside of your comfort zone, getting comfortable being uncomfortable. What’s the last thing that you have done on recent memory that’s pushed you outside of your comfort zone?

[0:51:43.8] CH: Yeah, a couple of weeks ago, was in Austin with some other entrepreneurs and it was a guy’s weekend. It was half fun, half masterminding, sitting around playing cards and stuff like that and then we helped each other with some business stuff. Then we brought in a Wim Hof instructor. This young woman from Colorado and she filled up a little kiddie pool with 800 pounds of ice and we did Wim Hof breathing.

[0:52:09.4] RN: It sounds terrible.

[0:52:10.6] CH: Yeah, it was the ultimate like getting comfortable getting uncomfortable. We did a bunch of breathing exercises. So it was funny, it was this young woman leading a guy’s weekend of dudes sitting on yoga pillows and doing these breathing exercise and stuff like that. Then getting in this thing and completely under the ice and staying in there as long as you can. So you know 12 guys sitting around and it was hard breathing heavy and stuff like that.

So that was a couple of weeks ago but yeah, I try to do one thing a week that I have never done before, one thing I am working on right now is I have a file on my phone in my computer. I have open mic comedy. I was just talking to a buddy of mine yesterday, Michael O’Neil. We were both working on five-minute open mic set because I do speaking but when I go on stage, I know I know what I am talking about when it comes to marketing and crowd funding and things like that.

So if it’s a talk I have given a number of times, there’s not a lot of nerves. But I have never ever done comedy. I love the concept of I want it to do it to make me a better speaker but also just to get comfortable being uncomfortable. It doesn’t matter what level you get to at a comedy. There is a great documentary called Comedian, that Jerry Seinfeld did. It doesn’t matter what level you get to, it’s still hard and people are basically sitting there saying, “Make me laugh.”

I can’t think of anything more nerve wracking and uncomfortable in doing that. So I did the ice bath recently but my next experiment is going to be some open mic comedy and try to make them laugh and get uncomfortable.

[0:53:42.1] RN: It’s funny because our mutual friend, James Altucher, I was talking to him and he’s done one standup routine before but the day Two days after I interviewed him he was doing his second standup routine in New York.

[0:53:55.3] CH: Oh nice.

[0:53:55.9] RN: And he’s the first one, I crushed it but it was all like friends and family so of course I crushed it. But he’s at the second one. I am going to a hostile crowd so I am curious to find out how it went because it has already happened.

[0:54:06.9] CH: I went just right down the street here to Mad House the other night. Just to see because I love comedy, watch online. I don’t watch a lot of TV but I watch Netflix comedy specials on YouTube, old stuff. I went to some laugh comedy here on Tuesday. The main set were seasoned comedians who didn’t do it in a while. I wouldn’t say they were great, the open mic afterwards, everyone left. So there was a table of four dudes, me and all these other open mic guys.

And they were not very good but context matters, like you said about James in that room, even if they kill, even if their jokes were hilarious, they had one table of four guys who were kind of paying attention. Me and everyone else in the room was a different comic who was trying to write their own open mic set and go out. So context matters a lot and if I did it again, yeah I don’t think I would bring 20 friends because laughter snowballs.

Context matters a lot and it was just crickets and I felt so bad these guys. They were out there just hanging themselves.

[0:55:07.4] RN: So we talked a lot about failure and obviously just on the topic of the comedy, a lot of people say, “You can bomb, you won’t die. It won’t kill you” right? It might kill your spirit for a little bit but you are physically going to be okay. You will see another day. If you had to really boil it down, what does failure mean to you?

[0:55:27.8] CH: It’s an opportunity. Failure is nothing more than an opportunity to try the next thing. I always look at life trying to figure out how can I make the failures less fatal right? First of all, most failures are not fatal. Most failures are smaller than we think. It’s funny when you talk about the comedy thing, what are we most concerned about when we do a speaking gig, when we do a toast at a wedding, when we stand up and do anything that puts ours stuff out there, what’s our brain telling us?

“Oh they’re going to laugh at you” that’s comedy. That’s the whole point so one of the two has to be true right? But they never do laugh at you and you never fall off the stage and things like that. So yeah, I think failure is an opportunity. I wrote a blog post a long time ago called Fear As A Signal and I grew up in Wisconsin where we have ice fishing and we used to put up these flags. They go up when you have a fish and freeze in. I think fear should be a signal that the project is worth doing.

When you feel that in your gut, when you’re scared, when you’re like, “gosh I don’t know, this might not work. This could fail.” That’s probably a signal that it’s worth pursuing because if there’s not those butterflies in your stomach or if you’re just head strong and you’re like, “No matter what this is going to work.” It has no chance of failure, well then it has no chance of success of either.

[0:56:40.2] RN: I like that. So what’s next on the horizon for you? What are you most excited about that you’re working on?

[0:56:45.9] CH: Speaking of speaking and –

[0:56:47.4] RN: Oh we talked about this, you’ve got a big one coming up.

[0:56:49.3] CH: Yeah, 10,000 people on Tuesday and 10,000 on Friday in the end of June speaking to the largest audience I have ever spoken to by order of magnitude. I think I have done maybe 2,000 people before and this is 10,000.

[0:57:02.7] RN: It’s five-X.

[0:57:03.2] CH: Yeah, five-X the largest yeah, be cocky stating with the Boston so working on that speech pretty hard because I definitely have to nail that one. So that is looming on the horizon right before that, I am going to Ireland with Phillip McKernan and some other friends for a guys/golf trip. So that will be a nice chance to unplug but I am launching a new high-end mastermind coaching program later this year called Clarity and Growth.

It’s like all the stuff that I teach in the realm of marketing for a more successful higher end entrepreneurs. That’s not an inexpensive program but I am really excited to get a group of people together to work through and improve their marketing in a small group format 10 or 20 people.

[0:57:43.8] RN: Yeah, very cool. So obviously being on the Fail On Podcast, I want you to leave us with a challenge if you will that the listeners and myself can actually go out and do and come back and report the results. So lay them out there.

[0:57:56.9] CH: Yeah, absolutely. I would say come up with – and it can be different for everyone. I am not going to tell you to go into Starbucks and go ask for discount or anything like that. I want you to create a micro failure. When you are doing your weekly planning, when you are doing your weekly to do list, so much of our to do lists are, “I need to do this thing, to respond to this email.” I need to do whatever. I want you to write down what you’re going to fail at or what you failed at last week.

Basically document your failures. I think entrepreneurs should do this, I think people in big companies should do this too. I think every meeting in every big company there should be a status report and there should be a line in them for micro failures. “What did you fail at this week Rob?” And report that back and tell people. I think big companies should do this at Centra because if you didn’t fail at anything you probably weren’t trying hard enough, right?

One of the most inspirational talks I heard when I was at Centra this guy, one of our clients actually came in and said, “You guys are so safe. You’re good that’s why we hired you, that’s why we pay you a ton of money but you’re going to slow.” He said, “If you guys don’t start making mistakes and failing a little bit, imagine you’re busting tables really fast.” He said, “I want a couple of glasses every night otherwise you are going too slow.” And that was a really good I think visual metaphor that we need to break some more glasses. Because then you just sweep it up and move on and buy another glass.

So at the end of the every week, look back at the week before and just write down “What did I fail at” and then report back. It’s not one specific challenge but document your failures because if you go a couple of weeks without failing at anything and that failure should have that uncomfortable feeling right? I am going to bomb on stage.

[0:59:38.6] RN: The pit of your stomach where it’s just like oh –

[0:59:40.4] CH: Just something where it’s like, “Oh man that sucked.” Then you realized the next day, it’s okay. So it could be a failed sales call. It’s got to have what I call collision with the market, meaning you can’t do it with the door closed on your computer. You can’t sit in the studio and fail and say, “Oh I tried to build a landing page and I misspelled the word.” That is not a failure. It’s got to have collision with the market meaning a sales call, you stand up on stage and bomb your comedy stunt like I am going to. You’ve got to have a collision with the market or a stranger.

[1:00:09.6] RN: Love it.

[1:00:10.3] CH: Awesome.

[1:00:11.0] RN: Well I appreciate the time, I want to respect it and I know you are going to get out of here. So thanks so much Clay.

[1:00:15.5] CH: Thanks Rob, I appreciate it.


[1:00:19.4] RN: Alright, so you can find Clay @clayhebert on Twitter and of course, that spelling along with the links and resources Clay and I discussed including more information on his marketing strategies and crowd funding resources, can be found on the page created especially for this episode that will be at Next week, we are sitting down with my good friend, Michael Gavin. Michael bypassed college and started his own production company, at the age of 19.

Since starting that first business, he’s done video production for weddings and events all over the work and film work for many, many successful entrepreneurs including big names like Richard Branson, Tony Robbins, Tim Farris, Pat Flynn, Louis House, Derick Halpern and many others. In this episode, Michael is going to share his start in the video industry and how he actually leveraged doing free work for people and how he actually landed his first filming gig for Tim Farris is a great story. Don’t miss it.

And if the podcast has the wheels turning please email me at and let me know what your biggest struggle is in getting started in business or actually breaking through the next level. As I continue to build Fail On with the goal of helping you achieve freedom by supporting yourself without a job, I’d be really grateful for just a couple of things. Subscribing to the podcast takes a single click and helps the show get found by more people.

And when people can find the show, it means it can help more people which in return means you are helping people by simply subscribing. To subscribe and rate and review the podcast, super easy, just visit or


[1:01:54.2] 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

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


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