The Fun Way To Build A 7-Figure Business with Jordan Gray
Coach, Author, & Course Creator
Jordan Gray is a MemberMouse Customer
"This whole thing has just been an eight-year playtime experiment and I'm still flying by the seat of my pants. I deeply believe that if I can figure this out, anyone can make a thing work."
Let’s play a quick word association game:
When you think about building your business, what thoughts, feelings, and ideas come to mind for you?
Would you say it’s…
- & Challenging?
Or maybe you’d describe it as…
- & Exhausting?
To be honest, the reality of starting and growing a business is a big blend of all of these.
And yet, our special guest on today’s episode of the podcast — Jordan Gray — chose a different word to describe the “gestalt” of his entrepreneurial journey.
What word is that?
You guessed it: FUN.
If you’re not familiar with Jordan, he’s a relationship coach, writer, and online course creator.
Over the past 8 years, he’s built a very successful online business that’s reached over 80 million readers, generated multiple seven figures in revenue, and transformed the lives of 10,000+ students.
(all while having a lot of fun in the process)
We are really excited to share our conversation with you today for one reason in particular:
You see, most of the time when Jordan appears on a podcast, he’s there to talk about dating, relationships, and intimacy.
This makes sense since he’s an expert in these areas…
…but almost no one takes the time to ask him about his business.
And that’s what today’s episode is all about.
You’ll learn about Jordan and hear the story of how he found joy in building his business from the ground up.
We’re grateful for everything that Jordan shares and sincerely hope you enjoy our conversation.
|1:58||Meet Jordan Gray and hear how he started his business|
|11:38||How Jordan grew his business through writing|
|16:55||A big mistake Jordan made early on|
|20:16||What Jordan had to learn to grow his business|
|26:49||The role social media plays in Jordan's business|
|29:24||Understanding your relationship to your business|
|37:43||How tuning into your emotions can guide you forward|
|43:00||Why it's no longer necessary to be a "starving artist"|
|52:14||Jordan's parting advice for entrepreneurs|
Eric: Hey, Jordan, welcome to the show.
Jordan: Thanks for having me, Eric. Excited to be here.
Eric: Yeah. My pleasure. Thank you so much for joining us. So, we’re just going to do the quick obligatory fast introduction to you, just so people kind of get a level set. So, if you don’t mind telling us what your background? Give us a kind of 30,000-foot view of what you do.
Jordan: Sure. So, I’ve been a sex and relationship coach for the last 11 years. I moved online just under eight years ago and I write and I make video courses and I coach people one on one and now my business is entirely online.
Eric: Awesome. And I think you have a really fascinating story of how you started and grew your business. So, could you share a little bit about that journey?
Jordan: Sure. Yeah. So, 11 years ago I started purely offline face to face in one on one and small group coaching in my hometown Vancouver, Canada. And what we were doing grew quite quickly and I felt like I kind of became the market leader within the first year, year and a half. And that was fun and my ego liked it for a couple of years feeling like, “Oh. I’m winning.”
Jordan: But then being at that market ceiling or close to it, exponential returns were not really there. And I thought what if I changed my market from men and women in Vancouver, Canada alone to effectively the English-speaking world and moved online, even though at that point, I very did not consider myself tech literate. And it’s a bit of a point of pride, I still do not consider myself that.
I’m definitely the talent in my business and I outsourced all the tech and design and web stuff and despite the things that I’ve consciously stayed ignorant of in the silos of my business, that just don’t feel fun for me. It has done really well. We’re doing seven figures a year and I feel like I have more scale and impact on fewer hours or definitely fewer stressful hours per month. And yeah, the whole thing just feels like a fun puzzle at this point.
Eric: Did you’re offering transfer pretty easily from what you were doing in person to online or did you need to kind of re-imagine it?
Jordan: It did transfer quite easily but it wasn’t necessarily immediately apparent to me.
Jordan: If I had more counselor coaching inside of myself, somebody who wasn’t as close to the business said, “Oh, just do this.” It would have been very clear, but I chose to go through it painstakingly one step at a time, quite like lone wolfing it in my process. So, ultimately it did transfer really easily and every book or video course or digital product I’ve ever put out really was just a result of me listening to my audience. And this 80th person asked the same question and I was starting to get annoyed with the question and because of this I was like, “Oh, I can never answer this again by creating a product. I get how business works.”
Jordan: So, yes.
Eric: We say that tongue in cheek but it’s how it works because it’s so important to listen to the audience and what they want. And it’s definitely in our benefit to provide resources that people can get at anytime and anywhere, but as also to their benefit. Because if we’re restricting ourselves to only being available on a one on one basis in real time, there’s a very small and select group of people that’s going to be able to work with us.
Jordan: Yeah. Very limited. And I also read into that quite quickly because the first three or four years, my business were much more revenue wise, it was much more predicated on one to one coaching. My emotional bandwidth, I kind of capped out at 15, 20 hours a week of Skype based coaching. I don’t know if zoom was around at that point. I don’t think it was, yeah.
So, the only thing I could do was continue to price my rates higher and higher, but at a certain point it felt like, “Okay. Am I just going to price out 98% of the people that would want to work with me?” Because at that point, my readership had really grown. I was doing somewhere between a quarter million to half a million unique readers a month on my website, just from organic search traffic. And so even if 0.001% of people wanted to work with me, that was still an overwhelming amount of people if my pricing was $100 or $200 and yeah.
For me, it felt less and less good to just price people out and not make myself as available and not only rob more people who are being impacted by my work, but also becoming an increasingly burnt out and jaded provider that served all of my even most favorite clients with less and less of my true self showing up.
Eric: You know, people who done any kind of one on one coaching will definitely get this, because there’s the informational part of the session, but there’s also the spoken and the unspoken processing that goes along with it. One on one coaching is great. I love it providing is great, receiving is great but sometimes there can end up a situation where it’s easier for the person on the other end not to do the work, sometimes.
Jordan: Mm-hmm (affirmative).
Eric: If you sit with information and material yourself, it’s easy for you not to do the work in that case too. But at the very least, if you end up doing the work it’s because you’ve chosen to go into it yourself. You’re not asking somebody else to do the thinking for you. You just let it sit and ruminate for a little bit and then but if you’re in one on one, usually you end up kind of lifting some of that.
Jordan: Yeah. A hundred percent. I think that it can absolutely be somewhat enabling to train all of our customers and clients that think that, “Okay. This person just always going to handhold me through my process. So, I can kind of phone it in because they will be taking some of that weight off my shoulders.”
And it’s hard for me to not translate this into the relationship realm. I would see that as the exact same equivalent of if there’s someone who’s in an intimate relationship and their partner is the only person who’s bringing them some difficult to sit with truth and not their friends and extended community. It’s just coming from this one thing.
It’s easier to either co-dependently want them to do some that work for you or to dismiss it and go like, “Well, only this person is saying it and yeah, they’re close to me but what’s one person.” Versus if your entire community or in a group coaching program, or if someone did a Facebook group or in a membership site where there’s a bunch of comments and you see people like, “Oh, we’re all moving towards this together.” And you can benefit from seeing someone else’s process.
Jordan: It’s infinitely more valuable to not just be hearing from one person’s voice, but to have that one to many offering. For the provider and for the receiver.
Eric: Yeah. It’s interesting that jump you made to use relationship in your work as an example, to explain something. It kind of ties back to something we were talking about before we got into this call. We were talking about tea. People who listen to this podcast know that I’m into tea. But we had both visited this same tea shop in Vancouver, BC and you said, “It’s amazing. I had no idea that the world was so deep. It’s a whole new world.” And I was like, “Yeah. Just like that with anything, right?”
And I was about to say something. I was like, “We need to start recording because otherwise we’re just going to have this whole conversational line.” But the thought that I had was, I think it’s valuable for each of us to find something in our life that we can go deep with, whether it’s tea, whether it’s relationship, studying relationship.
Because ultimately, I feel when you go deep with something, there’s kind of the surface level stuff that’s different across everything. But once you get beyond the surface, everything kind of has a truth that matches across the board. So, you may use a relationship to talk about something. I may use tea as metaphor to talk about something because at a certain depth, there’s a lot of similarities.
Jordan: Mm-hmm (affirmative). Yeah. A hundred percent. I once had a client who I worked with for a few months who his multi-decade career was, he was a mining ventilation specialist. So, where there were places that mining had to be done deep in the earth, he would make sure oxygen was being pumped down. And I was like, “Wow. Yeah. I guess that’s a job.”
And he would call analogies from that and apply it to the work we were doing. He was like, “Oh, that’s like this part of my job.” I’m like, “Okay. I would never think to potentially extrapolate that but amazing.” We all have that deep context on something. It does give you the awareness of themes or tools for other people’s deep work.
Eric: And there is a whole new opportunity there for a relationship product specifically targeted about deep earth ventilation specialists.
Jordan: Did you work three miles below your surface, it’s hard to meet people. Well, have I got a very specific sales page for you.
Eric: That’s awesome. So, we touched a little bit on how you’re getting a quarter million, half a million page hits on your site. Now I’m guessing that didn’t happen overnight, right?
Jordan: No. That was several years of writing several deep dive blog posts every week. Tons of marketing. Yeah.
Eric: So, yeah. And this is something that is noticeable when going to your website, that there’s a ton of high-quality in-depth blog posts. In fact, it seems you have an organic reach and get tons of focus traffic each month. And when we spoke earlier, something I found surprising is that you don’t consider yourself an actual writer. As in this, wasn’t a skill that you had specifically developed prior to starting your business. So, can you share a little bit about how you used writing to grow your website and business and your approach to mastering that?
Jordan: Sure. Yeah. From day one, for me, I really just sat down with my journal and it was like, “Okay. I’m going to build a business that is just my own and leveraging the internet. Starting with the end in mind, what do I actually find fun?” And I thought, “Well, I like coaching people one on one and I like writing.” I didn’t think I was a good writer. I still don’t necessarily think I’m a good writer, but I do think I’m a useful writer.
And I thought, “Okay. As long as I’m just putting out things that I either intuitively can assume will be valuable or based on the facial reactions of my one on one clients. No, is valuable and useful. I’ll just channel like the library of thoughts in my brain or on the subject into useful content, regardless of the number of typos or how many really detailed punctuation things I’m missing.” It just didn’t matter to me. I was like, “I’ll just help people. If I help people, we’ll see what momentum accrues with time.” And yeah, that was really it. I’ve-
Eric: You probably weren’t thinking about SEO or anything like that?
Jordan: No. Not in the slightest. I also started this Facebook business, the online part when I was 24. So, I had some kind of youthful arrogance running through me of just like, “Whatever. I’ll just make a thing and people will find it.”
Eric: It’s an arrogance combined ignorance, which I also had when I started my business.
Jordan: Exactly. Exactly. Yeah. Which was very helpful at that stage.
Jordan: And I hadn’t read the book but I’d read the book title, Be So Good They Can’t Ignore You. And I was like, “I’ll just be good. I’ll put out useful stuff and my articles will spread if they’re meant to.”
Jordan: And so, it wasn’t super surprising when six months in eight months in, much larger websites started to see my articles ask, “Hey. Can we repost this on our site?” And I was like, “Sure.” Not even knowing that that was a business strategy and things just grew from there. And all the major links that I’ve gotten from New York Times, BBC, Huffington Post, Vogue, Women’s Health, et cetera, none of them were ever asked for or pitched. I don’t have a content outreach person. I just stayed in my corner and made things and then websites asked that they could use them.
Eric: Nice. So, six to eight months and consistent, right?
Eric: So, you were doing one a week, two a month?
Jordan: At least one a week. I mean, especially in the first two years. Yeah. I don’t have a spreadsheet of it but I’m guessing I was probably averaging at least three a week for the first year. And then as I started to get more attention, more clients that are just the constant bouncing off to being, “Okay. Delivering service to people that want to pay me one on one and also still trying to carve out as much time to keep writing articles to grow the readership.”
Eric: I have a relationship analogy that proves that. Okay. So, if you like the barista girl or boy that works at Starbucks, the best way to potentially get in a relationship with them is not to go into that Starbucks once but to go in consistently and spend time there so that you get on their radar. And then ultimately, maybe something will come of that. Don’t try and be like, “I’m going to go there once and I’m going to go say something to them like, Hey, do you want to go on a date right now?” The first time you ever meet.
Jordan: Yeah. Or proposed.
Eric: Right. Or proposed. Yeah. You want to get in their field. You want to just spend some time there, feel the vibe but ultimately an important ingredient is that consistency. Being a part of the room.
Jordan: Absolutely. Yeah. Building rapport, building trust over time and yeah. I’ve had so many long-term readers when they reach out or when they sign up or when it’s a coaching session or a video course, they send out for like, “I’ve been reading your stuff since 2013.” And I’ll take the email address, put it into the search tool to see if they’ve been emailing me there ever before and they haven’t. So, people are just quietly watching for years before they crossed the threshold, then engage in some deeper way but they are watching, the whole time. I think that applies in every industry.
Eric: Let’s talk about when you were growing your business, were you using email and how did you use it?
Jordan: I wasn’t from the get go, but yeah, close to a year in one of my mistakes. I did not have any email lists at all on my site until I think at least 10 months, 12 months in. And then a colleague was like, “Hey, have you ever thought about this?” And I was like, “I have not. I will do that today.”
So, I did an email list eventually and it’s never been a huge focus for me. I do have a decent size list that’s just accumulated now. And yeah, I was emailing… because I was writing so much it never felt good to me to mail out each time I put out a new article because just for me, for my own temperament. Sending out a dedicated email blast four days a week to announce each new thing felt annoying. And so more often than not, I would write one, two, three, four posts within a week and then just mail out all the new stuff on Sunday and go, “Here’s some new things.”
Eric: Yeah. I like that approach. That’s what I… I have a personal website where I just keep track of the things that I do. I do it once a month and I use that kind of language too. I’m like, “So, this is stuff that happened. Here’s this, that happened. These things happen as well. I hope you’re doing well.”
Jordan: And to me that just feels it’s like an honest catch up with a pen pal or close friend who’s just like, “Here’s, what’s in my life.” Versus bombarding them with the strategic daily emails.
Eric: Right. Are you someone who works three miles deep in the earth? Here’s a blog post specifically for you. Now from a monetization standpoint, so it sounds like for the first number of years you were just putting out, putting out, putting out. And probably just keeping supporting yourself, maybe doing one on one coaching and stuff like that.
Eric: So, at what point did you start monetizing online and what form did it take?
Jordan: I released a few PDF eBooks and I made V1 of three video courses that I now cringe to think of their existence and how V1 they were. But yeah, video courses, three video courses and three books. Those were my first digital products. And I also started to use Amazon Associates just to… I recommended certain books and supplements and sex toys often enough that I was like, “Oh, I guess I could get 5% off of those clicks.” Sure. Why not?
Eric: Sure. Why not? So, are those V1 products still a part of your-
Jordan: The books are all still up. Those three courses have been down from hopefully the entire internet forever but definitely off my site. If someone downloaded them and put them on a torrent site at some point. And one of the three video horses that was drastically my best seller, I just read it and made infinitely better and that’s still on my site. So, same name but video.
Eric: Nice. You should rerelease the old ones on VHS?
Jordan: Right? Yeah. Betamax.
Eric: That’s awesome. So, aside from writing, what were some other major skills that you had to learn during your journey as you were getting your business started?
Jordan: All of it. Even in needing to have barely functional relationships to the tech aspects, like not functional enough so that I knew what to ask for from my tech guy. There’s been so many Google’s and YouTube searches of how to integrate this piece and what is this all about? And hiring and management and culture and how to hire, how to fire, how to invest money that you’re sitting on. There’s been an infinite direction and volume of things that have had to learn over the years.
Eric: So, for you is a lot of navigating the kind of, where does tech fit in, when do I need to engage with technology? How do I work with it? That kind of thing.
Jordan: Yeah. That and I would say also finding ways to kind of reclaim the human element. Because for me, there’s just like this constant dance of, “Okay. When I use X type of technology or X volume of technology, then size and scope and scale happening, these things are great because impact happens. And if it’s just really big numbers but the feedback loops have stopped. And so, I’m not interacting with people as much, then it feels too stale and robotic and lifeless. And so, then swing the pendulum and do okay. More feedback, loops more interactions with people.”
So, I can actually see the results, the benefits in people’s lives again. But then that becoming overwhelming when, okay, well now 800 people a week are emailing me looking for free advice because I’ve made myself too available.
Jordan: I think that’s also been its own dance of how do I keep my finger on the pulse of my audience and having real time interactions with people without drowning in it and using technology to scale while still keeping it human fields.
Eric: I think most of us, as long as we recognize that there’s importance that we need to keep our finger on that feedback loop like we talked about in the beginning. Really, if you’re not listening to your audience, you’re missing out on products and things that you can be creative for them. That’s definitely number one.
They’ll tell you where they want your business, your offering to them to go. So, that one’s, I feel a little straightforward but the one that I personally would struggle with is, okay, you do that and then you get all the people asking for the things. How do you back off? What techniques have you used to do that?
Jordan: I mean, depends how and where and what volume that’s coming in at. If I’ve introduced a feedback loop that is just bringing in way too much input, then I’ll just all kill that feedback loop. I’ll strangle off the place where I said, “Okay, this is available.” And it was like, “Oh, that is way more that I have no bargain for it. Nevermind.”
Either make it harder to find or if it was the second email in the email auto responder sequence, I’ll make it the 13th email. Just so someone’s already proven themselves to be sticking around and still getting results. Yeah. So, a lot of it is timing or placement. Yeah.
And this hasn’t happened in a long time, but in the instance that I put out an offering one to one or one to many offering that is more tied to my time, if it is overwhelming and too much, then I can also just rescind that offer it doesn’t have… Because you say here’s a product offer once doesn’t mean that it just now lives in your site forever. You can rescind features, you can rescind products. So, yeah, the whole thing is just so dynamic.
Plus, I have a better sense of what types of things to put out because there’s been enough miniature or larger moments of being burned, is it okay? I know that this style of thing doesn’t seem to work or this timing of a thing doesn’t seem to work. So, the missed steps are thus far. I mean, knock on wood are increasingly small. I’m not having as big deviations because I know what the ideal ranges for me at this stage.
Eric: What are some of your favorite techniques or tools for creating a feedback loop?
Jordan: Yeah. Having an autoresponder sequence, depending on which funnel it is. If I put the second email or 10th email as a subject line product name, “Hey, how’s it going?” And then just a three or four sentence, “Hey, it’s been an X number of days since you signed up for this product. I’m wondering what your biggest takeaways have been so far. What have you implemented? And if there’s anything that you would want to see differently. I’m always adding bonuses and re-doing things. So, let me know if there’s any changes you’d love to see. I’m always open to feedback.”
If that’s getting 10% of people that open that reply, depending on what volume I’m doing in that funnel. Great. I love knowing, okay, this is landing. This is a fourth person to say that this feature is kind of confusing. Something has to shift here and I can put this as the fifth to do on my list just to make sure that it does get done at all.
Outside of that. Yeah. Pulling my most engaged users by emailing them directly. Or I still do one on one coaching at the end of a session, if we do have done an hour, we’re now going over time, I might say, “Hey, for quick question, I’m thinking about adding this kind of a thing. Does this sound valuable? Does this sound useless? Just how does that land for you?”
So, the people that have gone the furthest down my funnel and are not the super diehard fans necessarily, but just someone who’s a casual user who’s happened to buy a couple of my friends on products. I’m very curious to hear their opinion versus someone that bought their first thing from me ever six hours ago. And they’re brand new. Yes. At certain points of your business feedback and user data can be as valuable if not more valuable than revenue. At a certain stage, you also have to qualify, okay, how informed is this feedback versus others. Whose advice am I adding that much weight to?
Eric: Exactly. A really good point. Do you use social media at all in your business? And if so, what role does it play for you?
Jordan: I did a lot in my first two years because that was just my plan. I was like, “Okay. I don’t have any momentum and Facebook has people. I’ll post every single thing that I do and just like spam the heck out of my Facebook wall to pull eyeballs over here.” And organic reach, especially on Facebook and Twitter was quite different eight years ago or seven years ago versus today.
Jordan: But even then, there’s always whatever TikTok or LinkedIn or whatever is the next hot thing that you can pull eyeballs from. So, yeah, early days for sure. I used it a lot. Now I do some advertising on Facebook. So, that’s tactically on a social media platform. But in terms of like organic posting, I use social media, very little.
I really like the audience, the community that I’ve built around my website and my email list and so I mainly engaging with those things. And again, the earned attention or earned feedback loop thing. I generally don’t care as much about what’s some passer by shocked scroller, who isn’t connected to me on social media. They see a post and they’re seeing one of my 600 plus articles, they hate the headline and write this use of vitriol that they think is really important. They’re like, I don’t need to take this as seriously as someone who’s been on my list for three years.
Eric: Exactly. Yeah.
Jordan: And so, yeah. I increasingly don’t interact with social media much at all.
Eric: It’s like the difference between how you would take feedback from a friend who’s been your friend for like 10 years and some rando who passes you on the street and doesn’t like the color of your T shirt.
Eric: And is having a bad day or whatever.
Jordan: Yeah. Yeah. If one of your best friends who’s known you for a decade is like, “You’ve been kind of a jerk lately.” You should listen to that. That’s a quality source.
Eric: Yeah. Exactly. Something I found that I’ve kind of said or thought about often is in relation to my business, that business is like a relationship. Starting a company is… I think I most frequently said it’s kind of like having a child but I’ve never actually had a child so I could be completely wrong. In some form it’s basically saying you’re starting a relationship. It’s not a set it and forget it situation. It has all the hallmarks of relationship. And I was just wondering if you’ve felt something similar in your span of time that you’ve been with your business?
Jordan: Absolutely. 100%. Yeah. I’ve always thought about it like a marriage and how committed are you to the thing because your audience, your customers, your clients can feel that. If you are showing up with consistency, of course going to get very different results than if you just love bomb your business with a lot of energy for a 50-hour period, once a month or once every quarter, you’re going to get a very different outcome just as you would with your intimate partner.
If you are doing small things often, if you were showing up and pouring love into the thing, the relationship, the business, it’s going to magnify back whatever you’re giving it in proportion to what you’re pouring into it in the first place. So, 100%.
And I would also extrapolate that into people joke with the seven-year itch, which studies actually show is a four-year itch not a seven-year itch. That dip is much more closely correlated with the four-year mark in a long-term committed into relationship. And I absolutely noticed that, that I was fueled by a ton of things in my first couple of years. It only carried me so far. And around the four-year mark, I started to hit that wall of is this really the highest and best of my gifts in the world? Do I care about this? Have I haven’t been fooling myself the whole time? Is there someone else for me?
It’s just all that same internal dialogue of like the shiny object syndrome and having to take those shiny hits of inspiration from other things and pour it back into your primary thing and finding ways to overcome the monotony and the boredom and the repetitiveness. I think that both in long form business ownership and in intimate relationships, these things are not talked about enough. That, of course you’re not going to feel the biggest, crazy burning desire like you did in the first three months for decades.
How unsustainable would that be for that thing and for your life in general, like nothing would get done. You’d struggle to feed yourself for sleep if you were just in that early infatuation phase forever. And so, finding and pulling inspiration energy from other things and funneling it back into your main thing is absolutely relevant.
Eric: Because yeah, I definitely experienced those times of my business where I was like, “I need to get out of this, because it’s just too much.” Vacation helps or taking a step away, et cetera. It didn’t end up happening with me because I’m still in my business, but there are legitimate situations where actually it is not right for you, right?
Jordan: Mm-hmm (affirmative).
Eric: So, how do we discern in business, if we come to a point where we think, “Okay. Is this my highest purpose, et cetera, et cetera.” How do we distinguish between the shiny object syndrome and the true, okay, this actually isn’t for you?
Jordan: Yeah. I would a hundred percent give the same advice to passion in a business and passionate relationship. If you’re several years deep, there is commitment and momentum and energy around the thing, then if you notice yourself starting to check out or feeling kind of disillusioned or less passionate about it. Then A, you shouldn’t just immediately go, “Well I felt some dissonance today, so bye. I’m done. Sorry about the wake of destruction behind me.”
Eric: Here’s the ring.
Jordan: Yeah. You somewhat just have to earn your way out. And I think for me, step one of that would look like really reconnecting to my deepest core values and go, “Okay, what is my life about? What do I really care about?” Because in a relationship in a business, sometimes that’s as simple as what it isn’t really about the thing that I’m doing or the person I’m dating as much as are these core values being extracted because maybe I’ve just veered off path and I haven’t been utilizing or living those values in the way that I’ve been in tracking with us.
Maybe I’m in my business in my relationship, but the tasks or the kinds of dates or the way we spend time together, et cetera, it has deviated. It’s gone off the flight path and so the pivot isn’t that big. Maybe it’s “Okay. You know what? I’ve been slipping into doing customer support or this thing and that is not my zone of genius. And I just need to course correct and get back in my lane because that’s when I’m happiest.”
And second layer to that would be, I mean the paraphrasing the Steve jobs concept of, if you wake up and look in the mirror every morning and you ask, “Is this still what I want to be doing? And the answer is no for quite some time.” Again, it’s not one day nor is it 25 years. If it’s been six months, nine months of like, “You know what I’ve been trying. I’ve been trying to get these needs met in other ways not just with my partner but with my friends and mentors and men’s group, et cetera, women’s group. Can I find a way to get this itch scratched elsewhere? And if not, is just really is a misaligned thing then, okay. I can face that on it and have the mature adult conversations of dissolving this thing and moving into something that’s more aligned.”
Eric: Yeah. That makes sense. I’m curious as you were kind of sharing your perspective on that, kind of going back to this thing we scratched the surface on earlier about how, when you go deep with one thing, you ultimately arrive at some truths. And I think the thing that we go deep with has something to do with natural disposition.
I just found myself wondering and thinking about how you’re describing these things. Because I resonate a lot with what you’re saying and I’m like, “Yes. All this makes sense. This comes from my experience too.” And yet I didn’t arrive at it the same way that you did in the same path. It begs the question for me, how do you see the world? Especially before you got into saying, “I’m a relationship coach.” Did you just find that you were seeing, breaking things down in a particular way, that was unique?
Jordan: In order to come to which outcomes?
Eric: When you were walking through the world before you necessarily had a direction about where you wanted to go and what you wanted to do, what was life like? What were the things that stood out for you? Did you just like naturally get a spidey sense when you would like see two or three people talking to each other, would it just make sense to you? And then at some point you realized, “Oh, not everybody sees it this way.”
Jordan: Yeah. I feel like it was a bit of nature and nurture that. I think that inherently, I definitely have a more sensitive empathic introverted brain and I just am very sensitive to my environment in general. And somewhat the nurture or the environmental conditioning was yeah, I didn’t feel entirely safe in my childhood. And so that made me even more aware of, “Okay. Then be hyper plugged, relational dynamics when is there enough tension that there might be a fight erupting? How do you keep the peace and harmony with people around you?” That was just something that was cultivated through how I was relating to my childhood.
Eric: Yeah. Let’s talk about emotional sensitivity because I’ve actually found this has been extremely valuable in business. It’s like you talk about these points that we can reach where so much destruction happens because so much pressure has been building up over a period of time, which is a result of lack of sensitivity to one’s needs.
So, what are some ways that people can kind of start a practice of tuning in to these emotional sensitivities and as a result of that help guide them on the right path in what they’re working on.
Jordan: Yeah. I’d say there’s two levels of that. I think one level to cultivate is the emotional sensitivity with your customers, clients, the people you serve. And the second layer is emotional sensitivity to yourself, to your own needs as the technician or operator or CEO of the thing that you were helping manage. On the customer level I think that, yeah, intentionally creating space for those conversations and keeping your finger on the pulse. Whether it’s one on one conversations or you have a client success director or someone who aggregates the keeping the finger on the pulse for you and said, “Okay, here’s what the tone of the conversation has been lately around what is wanted or what might soon be wanted in the forecast.” And yeah.
For yourself individually, if you don’t have some observing ego practice of self-reflective journaling or meditation, if that word doesn’t turn you off too much. Or if you’re a bit more type A hard driving, which I’m sure there are zero of in the entrepreneurial world. I think that sometimes kind of chaining yourself to the rocks. And if you’re not super prone to resting, then potentially making yourself sign up for a 10-day Vipassana retreat or take a three day-
Eric: That would be your first recommendation to a type A person?
Jordan: Not the first recommendation. I mean, it depends how much of a massive type A they are.
Eric: Actually, a type A person may be like, “Yes. I’m going to do this meditation thing.”
Jordan: Yeah. “There’s no way I’m going to flake out. I will be there to the very last second.”
Eric: “I’m going to crush it.”
Jordan: They’ll be sitting there meditating and judging everyone who leaves the meeting. Yeah. I mean, for anyone who has literally Googled the search term, “How do I rest?” For those, I would say forcing in, just making non-negotiable retreat. Again, it doesn’t have to be a Vipassana at all.
It could just be two nights, three days where you go to a hotel in your city or in a nearby more naturey suburb where you just book yourself in for two nights, you do not bring screens. You don’t bring a stack of self-help books and you just get to go be with yourself. Maybe do some journaling or you do some stuff that mines information out of you but you’re looking to reduce inputs and just check it and go like, “Okay. Am I still happy? Is this still fun? What do I need to bring into my life so that I’m more supported more in my center, more in my power, et cetera.”
And without that, yeah, I think at least weekends or quarterly solo retreat. I think that a lot of CEOs or showrunners will struggle to not deviate a lot further than they need to if they were just checking in with themselves out all in that kind of conscious intentional way.
Eric: Yeah. I think something that stuck out to me about that is the reducing of inputs. Actually, two things came to mind when you were talking about that, you were saying, talking about keeping the finger on the pulse. I’ve actually taken a pulse reading course. I learned that there’s actually seven levels of pulse that you can feel. It just depends on first of all, obviously your fingers need to be sensitive to feel this in practice, but there’s different levels of the pulse.
And I think relating to what we’re talking about is if you’re constantly just feeling the surface level pulse, you’re missing all the six other levels of things that are going on. And the reduction of inputs roots is really about keeping the mind busy, active is what’s keeping us from tuning into those deeper levels, which also have things to say.
And in my experience, the economies of scale. In younger years when I was more type A, starting my business, having that arrogance and the ignorance and all this stuff, the vision, pushing through things 60-hour, 80-hour weeks all this stuff. And not listening to those things, it didn’t really sink in for me. It didn’t really make much sense that there was a value there, but now I realized that I was doing a lot more work than I needed to do, because a lot of the work that was doing was really just about staying busy. Staying active. Feeding that desire, the habit of being in a certain state.
Jordan: Totally. Yeah. There’s two books that come to mind on this subject. One is, Essentialism and the other is, The Paradox of Success. The ears have really lit up over the last five minutes this conversation, those two books relate to this a lot.
Eric: Perfect. Another thing that you casually in an earlier conversation is that you feel as though it’s no longer necessary to be a ‘starving artist’. What did you mean by this? I’d love to explore this a bit with you, because I know a lot of people who had this. They put this on themselves. This starving artist syndrome.
Jordan: Yeah. I definitely think at least, the least necessary it has ever been. I’m sure that there are some people who have such hyper niched work that is just very for them and they’re not looking to make a commercial go or make their primary income off of that thing. Fine. Amazing. All the power to those people. It is absolutely never been more available.
The ease with which a person who just has passion or care or interest or under subject for them to create a lean seven figure business or mid six figure business around that thing over a course of a number of years has just never been easier. And we’re extremely spoiled. And it’s easy to lose perspective on that fact that decades ago was just an extremely different climate for entrepreneurship and the risk that was inherent a couple of decades ago for our parents’ generations and beyond it just it’s completely in comparable.
And yeah, when I meet people who just are not self-aware enough or taking enough responsibility for their energy allocation of how they’re showing up what tasks they’re allowing themselves to do in their business. And they’re blaming the market or technology or the tools on why their business isn’t going well. Blaming in general is generally a sign of-
Jordan: Lack of taking responsibility. Projection, exactly. So, I just don’t have a ton of patience for that mindset of like, “Oh. It’s really hard. It’s there’s so much risk and how can you do this?” It’s like the tools I’ve never been more accessible. The risk has never been lower.
Eric: That’s a thing though. It’s a mindset thing, right? Because I remember before I started a business, I was attending some learning annex thing. Have you ever heard of this learning annex?
Eric: Anyway, it’s these seminar things where multiple speakers will come. Ultimately, they’re just signed trying to upsell you to thousand-dollar courses and whatnot. But anyway, I was basically going to the buffet of different styles of businesses that were looking at real estate investing stock market investing. Trying to figure out how it’s going to make money because I knew I didn’t want to do consulting.
The thing is I was taking a course on equity structuring. Like what types of businesses do you use, different entities for whatever. And there was a stat that the lawyer who is teaching that course relayed, which was the top three ways that people think they’re going to earn money in this country and it’s not necessarily in this order, but it’s like winning a lawsuit, inheriting money from a relative or winning the lottery. All of which have nothing to do with self-effort, applying oneself consistently over time.
And so that is a real problem like that. If you’re in that mindset, I mean, can there even be anything done about that? Certainly, it’s not going to be to start a business. It’s be like having a baby and thinking that it’s going to cook you dinner in a week or something
Jordan: Exactly. And again, it translates to directly to not name it. It’s the exact same thing in how people relate to their internal relationship. A lot of people who have a somewhat boring, lackluster, unfulfilling life, want to find a partner to almost jumpstart the dead battery of their lives. And to also be in that kind of childhood regressed state of, “Well, when I was a baby, when I was a toddler, I got to do nothing, say nothing asked for nothing and my needs were met effortlessly just right away.”
And that’s what people want. People want to get into business or enter into a relationship so that their needs are met. And it’s that critical counter-intuitive of guess what the exact opposite works. If there’s any person who’s made it this far into this episode and they’re hearing this and there’s even 1% of their brain, that’s like, “Yeah, but it’s easier for you to say that starving artist thing because like you’re at this stage.”
I wish you could live in my brain for a day to really get how useless I am at almost everything, except for things that I found fun and just did those things over and over and then build people around me to make up for my failings, for my flaws, for my laziness. And really just like made a thing work in spite of those silos of lack. I still have a ton of fun.
I’ve gotten tens of millions of readers. I’ve been multiple seven figures in revenue. And the whole thing has just been an eight-year playtime experiment and I’m still flying by the seat of my pants. And I deeply believe that if I can figure that out and I’m still happily ignorant about most of the moving parts of my business, anyone can make a thing work.
Eric: Yes. If somebody hung out in your brain and then they hung out with mine, they would have a similar experience. Because I had no idea what I was doing and there are the ups and downs. There definitely are the days and the periods of time where you’re like, “What the hell am I doing? Nothing’s working.”
Eric: There’s a saying that probably not going to get it right. But if you want to be somewhere you’ve never been before, you have to do things that you’ve never done, kind of thing. Where the experience of living a way that you’ve never lived before, actually feel like. Well, it feels unfamiliar, uncomfortable, et cetera, et cetera.
A lot of the things that are part of our lives now, like our past selves may like explode because it’s so much has become habitual, right? And part of ourselves but because we were consistent over time and had enough commitment to push through the things that were uncomfortable.
Jordan: Absolutely. And again, with business, with relationship, I see both of these things as just almost like their own ongoing meditation practice or things that just continually shock you awake because you can’t go to sleep for that long because like, “Oh, here’s this new challenge or this new thing to calibrate to that I’ve never had to consider ever in my life.”
And so just like, if you’ve brushed your teeth with your right hand, your entire life, then one day, it’s like, “Well, you got to use your left hand now.” It’s like, “Okay, I’ll now fix myself to this.” It’s a constant dance and you can either see that as a negative and you can resent it and dig your heels in and resist life or you can go, “Cool. I’m going to grow from this. And this is fun.”
Eric: Yeah. I think a bold thing to say, but I think living is about being entrepreneurial. And I’m not saying that in the way we’re to limit entrepreneur-ism to making money. It’s about recognizing that not everything is served up on a platter. There is effort that’s involved in life. There is constant uncertainty.
There is an aspect of the culture we’ve grown up with the privileges that we’ve had, where people can naturally slip into a mindset where the expectation. What is it called? The entitlement mentality is that everything should be given to me and I shouldn’t have to work for it, which is super unfulfilling.
Jordan: Totally. It’s exactly that. Imagine signing up for a marathon and you’ve run 30 feet past the starting line and then confetti comes out and they put the metal around your neck and they’re like, “You did it.” And you’re like, “I didn’t do it.”
There might be some momentary, dopamine hit of like, “Oh, confetti, this is exciting.” It’s like, “I didn’t earn this.” And yeah, that laziness and entitlement is just really when our minds are cuddled and the bowling kind of bumper lanes are in your life. You don’t really feel like you’ve won. You don’t really get the character development that comes with it.
We are created by our problems. If you have a lot of problems in your life, that’s ideal. That means that your life is up to something. You are doing things. If you want a problem for your life, just try and do as possible and take no responsibility and help no one and just stay home and watch TV. Cool. Enjoy.
Eric: Right. But even then, people create problems for themselves.
Jordan: Yeah. You can’t escape them… so you might as well have high quality problems.
Eric: Exactly. Well, I think we’re pretty much at the limit here. I’m sure we could go on for a lot longer but it’s been a real pleasure talking to you. One last question. I think we’ve kind of covered it, but I just want to kind of ask the general question. If you would have any advice in general for other entrepreneurs that maybe we haven’t talked about. Something that comes to mind for you.
Jordan: If you haven’t started start. If you have started listened to your audience better.
Jordan: You’re here to serve. So, serve.
Eric: Perfect. There will be bumper stickers of that available somewhere in the world and your first three video courses will be available on Betamax, January, 2021.
Eric: Alright, well thank you so much. And tell people where they can learn more about you.
Jordan: My website, jordangrayconsulting.com is the main hub, everything branches off of that.
Eric: Perfect. Well, thanks again, Jordan.
Jordan: Thanks for having me. This was fun.
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