CEO of VideoAmp, CrossFit athlete, conscious entrepreneur, Forbes 30 under 30

ROSS MCCRAY 0:02
it’s a good way to start. I think for me, I don’t I don’t know if I can attribute one or two different types of key events. To me, it’s more them how I look at my past is more of these, this kind of continuum of different phases and worldviews, maybe even. And I think, when I was when I was probably, you know, a to 13, very much, taking my mothers and fathers worldviews on the thing is more natural, until I hit about that 1314, where I really started to take some of the base foundation of which they shared and started to really go out on my own and question my reality. And I think for me, that was, I don’t know, if there was a individual event that happened, just more of this culmination. And for me, the big thing that I took from them from my mother was definitely the passion and the and the, give it your all extremism and what you believe and kind of go all in and from my father more of the grounded, ask questions around yourself, and don’t really be affected by your environment and and try to take things and take things as data. And rather than taking things as personal, right, and that’s something that, for me, is how I look at my life in these phases. And when I hit about 1716, maybe when I started to really go to UCLA and start really going to university, and I was really, my mind was exposed to a lot of people that were more universal, different countries, different, different worldviews. And I think that was a very good exposure for me, because coming from South Orange County is normally the biggest lot of shared the world view.

CK LIN 4:14
Yeah. Yeah. Well, I mean, let’s not go too fast, I want to kind of rewind just a little bit, because a lot of people grew up. So a lot of people started listen to the parents wholesale. Yeah, the ideas in wholesale, right, I love this idea I actually got from Burning Man. Kids are essentially time capsules, of their parents. And whatever is in the time capsules are the ideas that means that want between the parents. And then obviously, most people grew up taking their the means from the parents hotel, then starting at 1213, whatever, they start to identify their own developed identity. How did you I guess, talking to you for a long time, I know you for a long time, you effectively run your life like meaning experiments. Yeah, they’re different phases that you go through. Yeah, but you end but then you’re very conscientious about the choices that you make speak of that, because you skip actually quite a number of experiments. You did? Yeah. Sure. Just share a little bit. So people know. Yeah, some more context.

ROSS MCCRAY 5:16
Yeah. Man, it’s hard. I’m trying to try to summarize that is challenging. I really think, you know, let me, let me I think one thing comes to mind now after you kind of phrased it in that way, and probably a better way to answer your original question. So I’ll try to tie it to the two together. So there was a time I’m not sure if I should have stood the test might have or at least a long time ago, there was a in my freshman year, about 13. When I went to high school and my zero period, English class, one of the first classes that I went to, it was set up in the sense where there was these pods of desks, like for afford for, for for his old groups. And this was a science eating, so teacher set, and it was me. And these three girls, and over the, over the couple months, you know, I thought we were gaining really, you know, a friendly relationship and just kind of a collegiate relationship. So I, at the time, I said, one to one, like, you know, Africa class, hey, one day, we should hang out and go see a movie or something like that. And I remember that I got the response of them pretty much laughing and saying, you know, the only reason why we talked to you because you want to cheat off of your, your, your answers your tests. And I thought that was remarkable. And I thought that made a lot of sense to me. Right? Yeah, it makes sense.

CK LIN 6:43
Oh, it didn’t traumatize you actually. Yeah.

ROSS MCCRAY 6:45
Yeah, it made sense. And then I think I shared that with, like, a friend of mine at the time. And he took that a lot differently than I did, right. And was like, What is going on here? Right? Like, like, why would you take that? And then my thought was, I don’t really care about what people think, or whatever the case is, you know, it is what it is. And he said, Well, I bet I bet you if you wanted to learn how to, let’s say, become friends or learn how to play the social game, and and, and, and, and try to add value and maybe an artificial or, or just an active way versus being to myself and just focusing on me versus what’s around me. But you could really figure it out. And probably could, I can, you know, deduce how to interact. And at that point, I just was bored. So I said, fuck it, I’ll just start to look around the world and start to try to analyze what’s happening. So I would just literally look around the room. And I would see people speaking to each other and body language and what some people would do to one another. And I basically cohort people out from different types of personas and different types of ways they speak, what words they use, and what body language they present themselves, and ultimate, everything they do what they’re representing. And I really started to just take in all the data in that way to try to create a worldview, or even a mental model. And then I started to try to AB test that and replicate it consistently. So taking on this kind of chameleon, if you will, trying different things and seeing how I can, rather than just being me for the sake of it, if I wanted to turn switch, and then I wanted to go out and give it give out. So given output to someone that will receive that in a certain way. That is I’m intending for them to receive myself. social engineering. Yeah, for sure.

CK LIN 8:38
12, 13 is the time we started to social engineer, you know, study this? Yeah, the science of social engineering, and how did that impact your worldview going forward?

Unknown Speaker 8:48
It changed differently, because, because when I started to, to when I started to try this, it was pretty exponential, in regards to different types of social engineering that I could get out to becoming, and then probably within a year, I’d say, more actively looking and taking it and trying things, I was able to go into a different type of group and, and, and assimilate from the jocks to the kind of the more popular, you know, duche crew to, to the academic crew, to the nerdy crew, to the musician, crew, I mean, I really figured out a way, right even to the different kind of multicultural groups that were there. different sports groups, I mean, I was kind of all over the place. And I had, I mean, I was I went from not really having an identity to be a part of two different sports groups, and a dance team to the APIB, which was like the advanced kind of, you know, crew to running like nerdy game crews to music group. So I kind of went around the horn, if you will. And, and I started to realize that I can manipulate a situation to to to really get a high probability of achieving an outcome by just understanding when people how they how how they receive things, and how well they respond to certain stimulus. And, and I think that got me on dangerous path, frankly, okay. Yeah. Yeah. And so, you know, fast forward, maybe a few years, I became very, I think I did well, socially in high school. And then when I went to university, I started to really use this the skills, if you will, in my opinion, for the wrong purposes. And how I look at that is, for me, personally, I look at the light, say, Yang Yang, as an example, or light and dark differently than some, whereas I think some people look at good and evil, as the same as light and dark, let’s say, Now, I don’t right. So I think there are tactics and intention, so maybe social engineering or manipulating or becoming going to someone and understanding how a few very aggressive and you speak in this way that they may not respond well versus sizing them up and literally judging someone and saying, how would I have to be to get the highest probability of an of a desired outcome, which I really think is manipulating and with an intention is some would say that’s a very dark tactic, not authentic tactic, or whatever you some we know, people can call it whatever you want. And I would use that, in my opinion, for I didn’t understand what my purpose was, and have a clear idea of what I wanted to do. So it was kind of a loose cannon, I just been doing this, I’ve been waiting and kind of lost my identity started to just kind of float around and just do things that I didn’t realize, you realize, you know, why I was doing it, and just essentially assimilating and, and creating an identity of myself that wasn’t really and having attention for it. And then all of a sudden, I had this image, which took me a few years to figure out why I who I am and like why I’m this way, and I don’t think it was constructive. It wasn’t building anything. It wasn’t giving back to certain people it was just kind of a very vain lifestyle that got kind of got caught up in the wrong the kind of the wrong crowd of people.

CK LIN 12:24
So you had a basically a wake up moment.

ROSS MCCRAY 12:27
Yeah, I did. Took was a few years. was it? It was a New Year’s party. 2010-11 New Years, where I’m just kind of looking around, and it was just a fucking like a punch in the face, like, what am I doing here? You know, and by all means, in regards to the what I had in kind of social point of view, and the people a lot of people will look at that as Oh, like this, this is a very successful party successful event and being a part of it. I was like, What am I doing? What value Am I giving back to people and and it kind of made me think about, you know, the difference was the joy that I thought I was given to myself being part of this decorate crew and people and kind of celebrities and you know, high networth individuals and just kind of people just like, with no real like, why are you here? And what are you doing with your time? and switching that to? What joy Have I given to people today?

CK LIN 13:41
So all in one day? All in only in one moment?

ROSS MCCRAY 13:45
Yeah. I’m just kind of looking around. And it’s like, what am I? Why am I here? You know, like, I think I was talking to a bunch of people. And then I’m just like, kind of going to get water or whatever. And then I’m just like, so what do I do now? I use that conscious, like, manipulative, like who do I want to go talk to what am i i’m very conscious, you know, and it’s like, I’m not just going into the water and just standing by and just smiling and looking around, you know, like, I’m literally thinking every minute now what now what now what happened and it’s always an outcome, there’s always a desired outcome that I’m putting on every minute. And I’m trying to optimize to get the to get that outcome. I want to go talk to this person, I want to get this person to be involved in this. I want to be able to this, you know, there’s always something

CK LIN 14:27
and you were 18 at the time.

ROSS MCCRAY 14:29
Yeah, I mean, 1819

CK LIN 14:33
how are you able to? So let me actually back back pedal a little bit. Yeah. How are you able to maintain that high level of awareness? Because when things are good, yeah, it’s easy to get drowned out by the noise. Right people coming at you people want to something from you, you know, you’re you have something going on, you have a lot of relationships just very noisy, right. But how were you able to maintain a high level of work is such that you actually watching everything going rather than just,

ROSS MCCRAY 15:06
I think it’s just practice, I think it comes down to that moment of just I bet you I can social engineer situations, and then doing it and just taking it more data and just and just, it’s kind of an addictive thing, right? It’s like, you start to do it, and you start to think about it. And then it’s just like walking, you get better at it over doing and doing it. So I think my level of awareness just got better over the years and my and how efficient I was at engineering situations to kind of get to an outcome just got better and better. So I don’t know, if I it’s just, it’s not like, Oh, I’m tired. Now I’m gonna stop doing that it just kind of an always on thing, right?

CK LIN 15:44
But I don’t mean external awareness of the outside. I’m talking about internal awareness like, hey, this doesn’t work for me anymore. Like, how did you maintain that high level awareness?

ROSS MCCRAY 15:54
I don’t know if I always did, and I think that was the problem. So I think giving like another example, I was always aware of like, okay, I want to go get this person. This person has a lot of influence runs this business has this is a second degree relationship with so and so which I could, you know, has a lot of influence, or could be an investor or something like this, right. And I would just say, I want to try to get that person in my circle. So that if I ever needed something for everyone to tap into this, then I could. And it was essentially that all over the place. And it was trying to build this network for the what if moment, or like, Oh, I could eventually tap into someone, whatever, right? Could be athletes can be, again, celebrities, or investors or CEO, or someone that would you know, some sort of influence. And I would just try to collect this, like collectibles. For the purpose of just because of like, one day, why not? Yeah. And then and then I think, to your point of the question of the internal. That was the switch, like, why am I collecting these relationships? You know, looking at like a card game, why do I have all these people, you just kind of get lost in the motion of just you’re doing it, you’re doing it, you’re doing it, you’re doing it? Okay, I’m all this person, I don’t know this person, I’m gonna go introduce myself, I’m gonna try to add value to them. And just try to Oh, you know, hey, let’s stay in touch security moment. But why, again? Why? And then all of a sudden, you have 1000 people that are in your sphere of influence. But what are you doing with that? What is the purpose of that? And I focus so much on just building up disruptor, you know, this kind of repertoire. But I never had, I never figured out a reason why I needed it. So that was really the switch was. So why don’t I go talk to this person? Think what am I the the the outcome, that from the outcome of getting them to be in network, to switching that to? What What am I going to do with this person in my network? And I had no idea. I think that comes with a lack of clarity of your purpose. And not knowing what you’re trying to do, I didn’t have an idea. I think it was kind of this proxy mechanism to stay busy, and instead of asking yourself the tough questions of why are you alive. And that was really the switch was I didn’t know that. So I think to you, so I don’t think I had that high level of internal awareness is what I’m saying. And that is what I try to now bring to the table, maybe call it the phase that I’m in now is I try to check into this as much as I can. I don’t have like a mechanism of a reminder on my calendar, like rethink why you’re alive. I think I just try to have more conversations like we’re having in this moment, and try to have deeper level of discussions. And I think that’s why I’ve always appreciated Our friendship is that there’s value there, because by having more conscientious conversations, you’re tapping into this muscle more, and you’re able to kind of sharpen your worldview while learning things with one another.

CK LIN 19:16
So a lot of people, especially in their 20s, especially after college, actually, yeah, they asked this question, what is my purpose? Yeah. And they asked that question, probably, again, they get to their 40s. Right, right. Their middle career somewhere? Probably. Right. Right, probably. And then they’ll ask that question again, after they about to retire. Yeah, that’s the typical times when they ask these questions. So do you think that purpose is like a one static answer? Or do you think that is a continuously unfolding?

ROSS MCCRAY 19:45
No, it’s always unfolding? For sure. Yeah. For sure. I mean, if you’d have a static purpose of it, you’re in a dangerous place. I mean, how could How could you? Every day, you’re receiving more data, you’re building a model, you’re testing your assumptions, you’re learning new things, hopefully. And if that’s not changing your view on things, and there’s a problem.

CK LIN 20:12
So So tell us a little bit about this unfolding of your clarify your own?

ROSS MCCRAY 20:15
Yeah,

CK LIN 20:16
for sure. what it was before?

ROSS MCCRAY 20:18
Yeah, it was an 18. Year, probably when we started meeting, right. And it was, it was this, I want to have global impact. What does that mean? Why do I want to have global impact? So I think it started off with like, I I think I can have impact. And we know that we’re met really. And then it started to go into, you know, in this evolution, maybe the second phase of this to, I want to add value, because shifting the word impact to value, I think, because to me, impact could be negatively positive could be impactful, right? Could be disruptive, impactful, potentially, by adding value is more of a clear word for me. You know, value is is is really what I’ve been trying to get into. Okay, so how do I add as much value as possible? And then I started to think, Okay, well, why do they want to add value to someone? What, what’s the purpose of adding value to someone? And I think, where that went to became digging deeper and saying, Well, if I could make someone happier, if I can make someone suffer less in their day to day, then that’s the type of value I want to bring to someone just having value. And I can bring value maybe to someone’s career to make them an extra dollar. But if that dollar isn’t necessarily Why do you want you know, money isn’t is a vehicle to achieve something. So going deeper, I got the point where we’re more where I am today, is I want to to reduce human suffering. And ultimately, that’s the value. That’s the impact. You want to go up a little bit to why why I want to why I want to impact and add value people’s life is so that I could have less suffering in that and to have them have a more joyful, fulfilled purpose.

CK LIN 22:33
Well, first acknowledge you for having that clarity. It’s a very noble purpose. Thank you. Yeah.

ROSS MCCRAY 22:39
And you know, that’s a whole nother place. We can go and say noble, we can say it’s vain as well. selfish. I think ultimate it’s selfish.

CK LIN 22:49
Okay, let’s talk about that for a moment. Do you believe in altruism?

ROSS MCCRAY 22:53
No, I don’t I think ultimately, why I’m choosing to reduce suffering, because that’s going to make me feel that I’m to make you feel better. Giving back to someone makes me feel good. doesn’t make me feel bad, right. If I felt bad for it, then I you know, I wouldn’t do it. So but look, I think, I don’t know if it’s a zero sum game. I don’t know if it’s, I feel good. when i’m giving back. So, um, you know, shame on me. It’s like, why not? Great. Right. Win win. You know,

CK LIN 23:26
I think it’s a philosophical discussion about this whole nature of altruism. I think it’s kind of you know, it’s kind of a stupid question really, to me, right. Who cares? Who cares? Yeah. Because ultimately is about net net. Right? If the intention is, to me if I feel good doing this, who cares what the come from is?

ROSS MCCRAY 23:46
Yeah, who cares? If it’s it doesn’t matter. It doesn’t matter.

CK LIN 23:49
Ultimately, I’m giving to somebody else. That’s right. Because of the actions that I take.

ROSS MCCRAY 23:54
So call that whatever you want. Altruism. not altruism. That’s great. Set positive. That net is what we want. As much as possible.

CK LIN 24:04
Cool. I’m okay. Yeah, yeah.

Okay. All right. Great. Continue, then. So. So then, how do you? You are also the CEO of a company, right, yeah. And then you have fiduciary responsibilities, you have you know, your responsibilities to the people in your life? Really, let’s actually just be more generalized that way. Sure. When it comes to reducing suffering, do you see if I can ask this question in more in a way that that that, that that’s that’s productive? Is it other people first, and then then you or you first and other people? And let me actually unpack it a little bit. Because people that have “noble” purposes in life. Yeah. The pitfall of that is they want to give so much. And yet they had nothing else left for themselves. Yeah, they usually sacrifice their health, usually sacrifices, their sleep, usually sacrifice their nutrition or whatever. All the time. And and that’s a very unsustainable way to do that. Right. And but flip it around, if someone is always focusing, and let me focus on me, right. And then it’s all about them.

ROSS MCCRAY 25:31
well, I think this is what I’m good at. It’s like, what’s the outcome? And how would you engineer backwards, ultimately, if you’re trying to focus on giving back, because that’s what makes you feel good. And then I would say, what is the most effective and efficient way for you to try to maximize your ability to give back, so I think it’s your start with give back, and then you optimize your tactics. And you should be thinking about maximizing value over the lifetime. And to do that, you have to have sustained throughput. You can’t have crashes, you can’t have lack of energy, you can’t have things come up. And you know, you have to look at it over a longer lens time. Because ultimately, value is over a period of time, you could have one year of a lot of value, but then if the rest of your life, you’re not adding value, then the lifetime value of what you’ve done is less than someone who had less than, you know, a more sustained method, say. So I think it’s ultimately what’s it going to take to maximize it. And I have not seen any individual that focuses and has a very value driven individual that just focuses on short term gains or getting through this crunches. So to get it back into what the people that don’t take care of the health. People who don’t make sure they’re mentally healthy people who don’t spend enough time with their own personal self and their responsibilities, whether it be family or whether it be personal health or personal mental health, spiritual health, then you are going to be affected in the longer term. So set right balance, because then again, I see a lot of people to on the other end, I see both sides, people that just focus all day on the output. And they’re all behind on work, and you continue to be in this rat race forever. And you’re never able to just go to one more deadline, one more this, get this out, get this out. And you’re in that rut for 10 years, and has people on the other side who just try to just focus on philosophical, I’m going to build my base up and you know, I’m going to keep working on myself and I’m not ready yet. I’m not ready to go and start a business. I’m not ready to to become a founder. I got it this this and that you’re never ready.

CK LIN 27:54
Yeah, I mean, that’s actually the thing to remember. Because as I’m academically trained, yeah. Right. So and you know me well enough. Yeah, my tendency is to want to align everything right, all the ducks in a row. Yeah,

ROSS MCCRAY 28:05
it is.

CK LIN 28:06
And then, then I’ll do something but it never happens. That’s right. You know, even if it happens, you know, what happens when a nanosecond and and all the ducks would be off and

ROSS MCCRAY 28:14
you use the framework, it’s, well, there’s a certain level of call it everyone’s different how they learn. For you, you’re definitely a more of academical, you get a lot of value in preparation. Right. And I necessarily am not that way. And but there’s value in the preparation, there’s value of failure, trying something failing, wanting from you’re trying it again, and I’m on that camp pretty aggressively. So I think everyone’s different. And I think, you know, if I never prepare it, if I never learned how to take a step back, and I look at other things, and I think that’s a pitfall for me. And I think for you, it’s you can get, you know, analysis paralysis. Yeah, yeah, for sure. Yeah.

CK LIN 28:56
Okay, so let’s get it get down to tactical, yes, I don’t want to just a philosophical conversation, and people are inspired by your narrative. But I also want people to not only get inspired, but in learn specific tactics that you do to strike that balance. Right, that harmony. So what are some of the disciplines that you have? Or the habits that you have as a way to both do and also think, like set of your day for sustainable throughput

ROSS MCCRAY 29:24
Yeah, I think it’s about creating habits. And it’s about discipline. That’s the underlying tactics that I use to go about everything that I do. And you have to choose a couple things, focus, discipline habits, right. Those are the things that I really probably best describe my tactics and how I approached my life. So what’s the focus, they only focus on a few things. For me, health is one of them. So I unpack health, which with it, being energy being your diet, being your physical activity, your spiritual mental health, all that I kind of put into the bucket and tactics that I do for that is waking up at the same time, every day early, having a routine, finding something a physical activity that you can build skills upon. So not just oh, I’m going to run today and bike today and climate day and do a class today, because you’re not really building skill sets. I like to build to focus on something that I could build and be competitive with, which is kind of killing two birds with one stone. So you can go do something active every day. But if you’re not bettering yourself in something, then you kind of lose something in my opinion. So personally, I’ve been doing CrossFit and olympic lifting as my focus

CK LIN 30:47
What did you pick that? Because you have many, many options?

ROSS MCCRAY 30:50
Yeah, well, I think inherently I like those two, because especially the CrossFit side, because it brings in a lot of variety already. And it’s very measurable, very competitive and very intense. So workouts are measurable holds certain weights or times certain number of reps, you have to do that you can compare yourself against other people. And then you can track your progress. So it’s very ROI driven, and it’s measurable and and if you’re able to measure how your physical output is, then you’ll take that habit, and that kind of will, it will correlate to everything else that you do. So there’s these added benefits of not just kind of think of it like of health as a vertical pillar, the the intensity, and the measure, everything you do is a horizontal tenet that will go across other things like my professional life. So if I’m honing in, on on the discipline, and I’m honing in on the measurability and the intensity, then when I go and I finished my morning routine, and I go to the professional life, and I’m able to I’ve already sharpen those skills, and I’m going to want to reuse that and measure my own self worth measure my teams and way measure our output and our mission and to be able to have the intensity and the wherewithal to do what’s necessary. And to be able to use that as a competitive edge in the marketplace against your competition. And to use that as a tool to inspire others is something that I also get out of it. So I can go and do some yoga, that which I love. But something that is there’s all kinds of different Yoga means but more of the traditional, more meditative, slower paced yoga, the more as that’s going to give you a lot of things more like mindfulness and more things like mobility, which is very important part of my life as well. But you won’t, to me that’s less valuable, or less attributable, also into your work life. And other things. For me, the competitiveness, the intensity, and the measurability that you get from CrossFit is very valuable in professional career,

CK LIN 32:57
what other tactics, whether disciplines do you have.

ROSS MCCRAY 33:00
So I like to minimize the number of decisions that I make every day. So I call that the decision fatigue of people call me an asshole for even talking about concept of decision fatigue, I find it funny, but it’s true, right. And it’s I when you make a lot of decisions, micro decisions, I’ve seen how that has added tax to my life. And that’s something that drags down my energy level is very important to me. So the decision fatigue is what am I going to eat today, what am I going to wear today? You know, where am I going to go for lunch is when I see all the time people once I don’t really care about that. For me, I look at food as fuel, I look at what I’m wearing should be practical, to be comfortable to to to just have that be a decision that I don’t want to think about what I’m wearing or what I’m eating and where I’m going and to have that be automated is very important. So I subscribe to meal plans for their be a service or finding someone that you can have more cooking for yourself from doing that on Sunday or subscribing to a services all kinds of ways to do that. Having it delivered to the office and looking at it right now my food in my refrigerator. That’s a great tactic to just kind of focus on worrying less things and I buy in bulk and if I enjoy a T shirt and notice by 10 of them and I don’t want to have the hundred different things that I’m wearing and focusing on that what value Am I generating from from that? I don’t I don’t see any incremental value of focusing on fashion to me is very, very vain concept.

CK LIN 34:39
How interesting. Huh? I know that you’ve been trying to tell me about getting my own food prep meal service for a long time. Yeah, for a long time. I kept saying no because of various reason the cost, the time. it’s always uses you ever tried it? And holy crap. It’s such such a gift. such a blessing.

Yes. Anytime I am hungry it’s is right there. Within three minutes on my food. Now is it maximize in terms of nutrition or taste. It’s not maximize. However, it’s optimized. Because if I need it is right there.

ROSS MCCRAY 35:20
Well, I think max realizes is a I don’t know if I agree with you. Because it’s what are you maximizing? Right comes down to Why do you look at what is your purpose of food? If you’re maximizing how tasty it is. And when you’re chewing for optimizing mouth pleasure. Yeah, maybe not. I mean, some are actually driving an hour to go to lunch to some random ass place, you know, in LA far away, sitting in traffic to go into the for an hour having a food coma, driving back another hour, take three hours in a coma later. But you got that mouth pleasure.

CK LIN 36:05
Is it worth it? Right?

ROSS MCCRAY 36:07
Well, I mean, it’s up to the individual. Right? Not to me.

CK LIN 36:11
Yeah, same here. So after what was that celebrity chef who committed suicide? He had a show.

ROSS MCCRAY 36:22
Anthony Bourdain.

CK LIN 36:26
So after his passing, I started watching his show just as a way to like, hey, what makes this guy special, right? I was inspired by him. But as a result of that, I also drove an hour to try out some of the restaurants and I realize the payoff the mouth pleasure didn’t warrant whatever time effort

ROSS MCCRAY 36:45
There is time and place for everything, you know, I mean, special occasions and experience you with certain kind of people. That’s one thing, the experience with people around something that it versus routine is very different. So yeah, yeah.

CK LIN 37:04
Any other disciplines that you wanted to share? That gave you a really high ROI for the level of throughput? Use your word.

ROSS MCCRAY 37:16
Yeah, I think I think making sure you look at how you’re spending your time has been something that I’ve done in the very beginning. And it’s a funny one, because when, frankly, when I when you ask me these questions, it’s not easy for me to the most impactful, highest ROI habits that I think I have are so ingrained in me that is just like air, right? Like, for me the food concept. Is, is so just, I forget about, it’s like I forget the know, not everyone does that, right. And like this hit me with the health thing. So some of these things that I do, are just so common, like putting on your underwear or putting on socks. It’s like, I don’t think about it. It’s just important. So that’s why I kind of pause. But I would say the time thing is one of those where I put everything in my calendar, and I make I make everything measurable. So that on a weekly level, usually on Sundays, I’ll look at my last week, and I’ll see how I spent my time and I’ll see how that attributes to what I’m trying to get done. And then I will try to better plan my following week. And I probably remove so many meetings and distractions that has been slotted just because it was slotted two weeks ago, three weeks ago, is this important for me to do either move those or cancel those or adding a new things that come about so that I can really plan on a week to week level, versus being so reactive on a daily or even hourly level of what it going to do and have that discipline to be thinking about those intentions, be more purpose driven and thoughtful regarding how you’re spending your time on a weekly level. And looking in doing a little bit of a retrospective and how your last week went. And then planning forward and had something that I’ve done very for probably 10 years. And one of the things that I’ve always found to share with people. Not what not really in my circle, but 10 years ago when I was starting to do this. And when I started asking around and everyone has the the intention or not everyone but most people want to be let’s call it successful. They want to have financial security, they want whatever goals they have. Yeah, I mean, it’s everywhere. I want to be rich, I want to have a lot of money. I want to have a company I want to have I want to being an influencer, I want social media followers, all this crazy shit. And then Okay, let’s let’s just let’s just fancy them for a second. And I’ll say so how would you spend your day yesterday? And like, what do you mean? Let’s break it down. What time do you wake up? I woke up at nine and I went to breakfast. Drove somewhere for some food. And then I came back and watch some TV. And then I went to work my shift from 10 to Five, and you know, whatever it is some some new some whatever their day job is. And then I came home and then I played some games, and I went on social media. And then I went and I met up with a friend and I went to happy hour. It’s like, and then I’ll add that I go to bed late. So Wait, so what did you do in that day to go against everything you said, which was what your goals are. And it’s funny because it’s so discrepant. And it’s sad, because it’s delusional. Oh, I mean, let’s just take these example of trying to become a founder of a company. You say that’s a goal. Yeah. And then you ask someone how they spend their time and It’s very sad. Because they don’t have the consciousness to understand that they’re not doing anything towards those goals. And they’ll have this goal for 30 years. And I see people in their 40s and 50s. They just become very bitter of like, what did I do with my life? It’s like, well, you just had a day that I just described, right? a more practical example of that is, is I woke up at 5am. And I spent an hour to work out, I and then I got to work, you know, I figured out a job that I can do to pay the bills from 7am, or 8am to four or five. And then I figured out a way to maintain my energy level by being healthy and eating the right way. And then I started my second shift from five to 10 11, my second seven or eight hours a day into something that’s very deliberate towards building towards my dreams, you’re not hanging, you’re not going to happy hour, you’re not playing video games, you’re not on Facebook for an hour, you’re not driving around and get lunch, these things add up and you have an entire second part of your day that you can be really building towards your vision, and that this makes a difference. How you spend your weekend time is very important. It just takes time. It takes 40, 50, 60, 70 hours a week, to be able to do any of what most people have as a goal. And they don’t spend the time to do it. And it’s discrepant, and then they get sad. And then they suffer. To get to the point of the mission that we’re discussing. They suffer. They add suffering to their life because they get upset. Oh I am not making progress. Oh, five years goes by and then they wonder what they’re doing. And they get these crises and they suffer and it’s sad to see them suffer. And especially because they’re throwing away their time. They are mismanaging it.

CK LIN 43:04
Yeah, I feel you. I also feel them, right.

ROSS MCCRAY 43:06
Yeah, I do. I want the best for them. My opinion is you either need to reorient yourself and come to reality that you don’t want to start a company. You just saying this because you are vain and desire to be successful. Because it’s just been ingrained in you in this Western society. Let it go, what you’re saying is you want to just be on Facebook, you want to go have mouth pleasure, you want to play video games, and you want to be working a mindless job. That’s fine. If that’s what you just don’t be discrepant. Own up to it and say, This is what I want to do with my time. Great good for you. You need to align your tactics with your intentions. And that’s the point. Just have a conscientious to understand this is what you want to do. You want to go party every night. Okay, it’s up to you. If that’s how you want to spend your time just but don’t. Don’t lie yourself. All you have is your integrity with yourself. You know?

CK LIN 44:09
I mean, what you just said, it’s, it’s true. Have integrity with with yourself. First and foremost.

ROSS MCCRAY 44:17
And yes, and that’s the problem is that most people and look it’s not that they’re not trying to, it’s because they’re not aware it’s a simple exercise. ask someone what they want, what their intention is, what their goals are, which are career, wherever they are. And how they spend their time today. do that and plot it. This is unbelievable. There is a lot time in a day.

CK LIN 44:39
For sure. If you look at so one of the easiest way to to see what people are truly committed to right is look at their time. Yes, their calendar and also look at their their spending habits, their credit card statement for sure. Because that’s what we have. The limited resource that we have.

ROSS MCCRAY 44:55
We can get more complex and look at energy. But this is an easier framework.

CK LIN 45:05
Okay, so let me actually ask you a separate question, because you hang around with a lot of achievement oriented people. Yeah. Right. Do you feel that actually achieving your goals makes one more happy? Or because there is a phrase that sometimes more grief is caused by answered prayers than unanswered ones. Right. Sometimes you grasp the goal so tightly that if you don’t achieve it, your life turns to shit. Because I didn’t achieve.

ROSS MCCRAY 45:38
For sure. I’ll give you a concrete example. Okay. I had a financial goal when I was 16, 15, whatever, that I hit when I was 22. And when I hit it, it was the most disappointing thing ever.

CK LIN 46:01
So say more about that. Why is that?

ROSS MCCRAY 46:02
Yeah, I mean, look, it was just this, it was a vanity metric. It was a vanity goal. Right? It was, yeah, I want this. And to me, this is what success can look like. And it just has nothing of that. It was such a letdown. And it was like, again to the Why do you want to have these series of numbers in your bank account? Okay, is it for securities for this, but ultimately that’s not what I optimize for. Again, what I always had deep inside and was at the time, when I was 21, or two, it was still it was exponential impact and, and then it went to the value. And then it went into the suffering, right to reduce suffering, which is where I’m at today. And that goal did not achieve anything directly correlated to reducing suffering. Look, it takes some assets to help you get there. Don’t get me wrong. But that is a proxy. And it wasn’t activated. It was just again, it was like this, the kind of the same idea of getting to have someone in your network. But if you’re not activating, you’re not realizing any value. What does it matter? You can know the most important influential person in the world. But if you’re not generating any value from that, it’s the worst.

CK LIN 47:16
You have a lot of cards stacked for you.

ROSS MCCRAY 47:19
It’s actually the worst, right? It’s the worst feeling in the world. It’s just the worst. Because it’s better to have no assets or it’s like you have all this potential that’s unrealized. That’s the point. You realize you have these assets, these potentials, and unrealizing it to me personally is the worst.

CK LIN 47:41
It’s one thing to strive for something. Right. There’s a hope. Right? Once I get it, then I’ll be able to activate that now that you have it.

ROSS MCCRAY 47:51
It’s vanity, it’s again, you got to get to understanding what you’re really trying to do. It is hard. Don’t get me wrong. You can always go wide and figure out what you want. And as five WHYS, oh, I want to make this Why? Because of Okay, why, why? Why? Why? Just go deep as you can. And then try to try to stay there. And there’s always other levels. There’s always deeper levels, and he’s always unpacking levels and getting clarity. But that’s that’s the best thing you can do in my opinion.

CK LIN 48:16
Yeah, I mean, to me, that’s what makes life beautiful. There’s ultimately once you figure out quote, unquote, the answer you have everything that you need. There’s no more questions, right? It is boring. Yep. Would you want a life no questions. Yep. To me. I’m big on questions. I’m so curious about, about what’s the what’s the next level? So on that note, what kind of actually asked a broader question, because you not only do it personally, you also have a circle of people around you. You also have you know, staff or employees who works for you. A social structure. Yeah, I was going to ask you. Oh, what makes your best friends your best friends? So, all right, coming back to the question. Yeah. So you’re not just responsible for yourself, you’re responsible for your family, right? You’re responsible for your your friends, you’re responsible for your employees? Well, let’s start off with this question. What makes your best friends your best friends?

ROSS MCCRAY 49:15
So, to me, what I appreciate the most with friends, is number one, the level of communication. So when you’re talking about any concept, how deep can you go? And how fast? How fast? Can you get to that level? So when you’re getting into a philosophical question, and you’re having a conversation of value of say, ultimately, like the framework is, if we have half an hour discussion, we spend a half an hour together in leaving that discussion. What was the net net value that we generated? Can we take anything, because there any breakthroughs or discoveries that you can take to add on to yourself to change your world views or to add value to a new new tactic or new question to ask yourself are anything that can add value to the way that you interpret the world? from both sides, right? Again, it’s not just it’s the net, net, and both sides. So if just if it’s just a one directional coaching, coaching, coaching, it’s like, there’s some benefit there. But if we can bounce ideas off each other and and get to that point of net net value, add that that’s very impactful for me, and I really appreciate that. And then the question is, how fast can you get there? Because some people could spend 10 hours and come up with one discovery. But how deep can you get the shared understanding the verbiage. And when you’re talking about something and be able to link things in the passion, the attention to detail, you’re talking about thing that’s very fleeting, or very, like, whoo, whoo. Right? And it’s like, can you grasp these concepts? So there and you create these, these archetypes and these symbolisms? Can you have a shared consciousness? How quickly can you get there? And how quickly can you generate and challenge each other and add value to these questions? To me, that’s where I look at my greatest friendships. It comes from that.

CK LIN 51:14
And it’s one of the reason why I started this podcast. Yes, I enjoyed this type of conversation. That’s great. I like long for them. And not everyone’s ready to dance with me this way.

ROSS MCCRAY 51:23
Especially your. Yeah, no, I agree.

CK LIN 51:27
Especially me. Yes. Yeah. Okay, so so socially speaking, though, do you have I suppose different pockets of friends? Or do they all know each other? Or do they all complement each other?

ROSS MCCRAY 51:40
Yeah, there’s there’s pockets, but it’s not intended to be like, compartmentalizing. I think it’s just it just happens, right? I would say I have to be honest, I mean, I’ve had different friends over the years, especially. And I think, as most relationships happen, some relationships grow apart. And just there’s different values on there’s different intentions and different goals. And, and that’s fine. And for me, I think some people have different opinions here. Some people I’ve seen judge this in certain ways, and but if you’re having a friendship for, you know, your childhood friendship, or 10 years ago, best friend or whatever, and it just starts to go another way. And they will bring on different habits, and they’ll do different things and different your values start to tear apart, there’s some level of repair some level of, of effort you want to put into to that. But for me, I’m not someone who’s going to throw the kitchen sink at trying to rehabilitate a relationship, if it’s not organic anymore, if it’s not authentic, and you have to do all this work, and there’s no net net benefit. So, so I think that’s what happened with the social circles is that some people will grow away from each other. And that’s fine. I don’t have any issue with that. Personally, I wish the best for them people, but I don’t continue to bring people through it’s kind of part of life, there’s different periods of times in which you’ll go through and I, I’ve had a lot of close friends over the years, and they’re in different places, and I’m in different places, and may stay in touch once a year or something like that. And that’s great. That’s more of a kind of a touching base. But you know, I don’t I don’t go out of my way to spend time into that if I don’t think there’s mutual value generation to the same point of how I defined my closest friends.

CK LIN 53:31
Okay, so how do you translate this to running a company? Because a lot of people are very purposeful in their personal life? Yeah. And they want to bring this into the business life. And you’re very intentional about bringing this purpose moments into the business, can you kind of break it down for the people who are listening to this? How do you translate this?

ROSS MCCRAY 53:49
It’s changed over stages to okay, right? When you’re bringing inyour founding team members to when you’re getting to 20 people to, to you to 50, to 100, to 150 plus, right, growing more than that. And in the, in the very early days, at least how we went about it, it was finding people that have very strong shared sense of values and mission and very much a shared worldview. And there, and there’s benefits to that. Whereas very quickly to make decisions you’re on on the same page, there’s no dilution and communication. And there’s, it becomes a very powerful small, elite SEAL team that can generate something that is very impactful, and that throughput is very high. Now, in my personal opinion, I’ve seen at least even ourselves, our ability with eight, like eight to 15 people, the throughput that you can generate, and just from the lack of dilution and just a very shared of, say, a lack of diverse worldviews, and this can be very effective in delivering a very simple, focused mission. And at least in our company, I saw that throughput of that small team be able to probably generate more throughput, then when we got to 40 or 50, even. But the investment to go there was to reorient ourselves and to create a different Foundation, whereas we could take on 10 X the customer base, so that group of eight to 15, maybe the most effective at delivering just compartmentalize it to say, we use customers, as an example, get 25 enterprise customers, it started to break down when we got to say 50. So we had to be a little bit less efficient on the unit economics, if you wanted to get to 100. So it’s an investment for the future. So that’s kind of how I saw our company grow in these in these tranches, and becomes very different operational, you’re bringing in middle management and bringing in more process you bringing in different diverse views, different approaches, and that’s something that we did, and it was a big learning experience for me because I go from this very intense, everyone thinks about the world in the same way to how you scale a business, you need to bring in diversity, you need to bring in different types of worldviews, and you need to have that be less, you know, it’s more about risk management as you grow. And as you get more customers and how you bring in more process and other stuff, the culture, I had to start to find cultural champions, that leaders that still sharing a common foundation of values and missions, you know, so say we had say there’s 10 core ways look at the world and having a 10 out of 10 have what are the real core five? What are the things that we always want to have, and then have each leader and bring in additional couple extra points that they localize, for maybe engineering their own flavor. So rather than making it so much of a cesspool of thinking, you need to have a still a common ground. So you don’t have to say non culture, yeah, but you need to make the tough decisions. And what you’re really willing to say we this is, this is what we stand for. And now let’s say now it gets to even less than 10 to five, the three, you know, I think that’s how you scale. And that’s kind of where I’ve personally can say at least video has gone.

CK LIN 57:31
Can you tell us a little bit about your personal kind of growth process in when you scaling the company? And did you have to grow personally?

ROSS MCCRAY 57:39
Yeah. Yeah. And it was always delayed. Yeah, i think i’ve heard this I’ve had people tell me these things, but it just didn’t collect, it just always was three or six months later, until I realized the stage that we’re in. So the company has been growing pretty quickly, thankfully, and faster than I realized how that’s that’s kind of where it is. And then all of a sudden, things are going great. And then just like one week, things are not and things are dropping, and the more clients we can support and the assumptions of the unit economics of one, one part of this can support three customers all of a sudden, now can’t anymore, because the customer base is very different. And you know, things like that just happens. And it’s it’s hard to stay ahead of everything. So there’s been some reactive phases, where as I need to look at the data, and and reflect what’s my role in organization for it, I can’t dive in and solve all these problems. I can’t be in every client meeting, I can’t make every product decision. And those are the things that you learn that you have to figure out when’s the right time to scale, when was the right time to give more control and to give more ownership to other people in the company? And what are the things you need to keep still what what decisions do you have to make? And then what decisions can you empower others to make? And those are the things you have to check in on. And I don’t think I’ve made all the right calls over the years, I think it’s developed and I’ve tried to look at certain things and I make bets. And maybe sometimes they work sometimes they don’t. And you have to refactor and you just look at the data and you got to be open minded. Look at the right KPIs in the company. What are the important metrics you want to look at see other trending have open conversation about why they’re not and reassess? Maybe I should have made those know those practices, mafybe I should have longer time decided the roadmap, but I should have given up sales meetings earlier. So it wasn’t a bottleneck there. Or maybe we should have figured out a way to change our client services versus this and that, you know,

CK LIN 59:38
so Okay, so you, you said a lot of terminologies, right? So that maybe not everyone would be able to understand that, can you compromise that just a little bit, just demonstrate one example of where you had to shift your mindset about, for example, control, right, as a CEO of a company, this is your baby, as this, you know, this, you had let go of some control, whether it be product decisions, or

ROSS MCCRAY 1:00:04
I mean, I think the product was easy to give an example. So from the beginning, you know, phase one, whereas you’re literally in a room and you’re making one main product with a couple main experiences and screens, or you’re deciding how the user interacts and what buttons you press and the screen flow of you press this button and you go here in the software, and then you press this button, and you go here in the software, and no, no. But to answer these questions, let’s make a graph look like a bar chart versus this line graph, have this kind of experience, this kind of right, even though the colors to then maybe a phase two have, okay, I don’t decide the color scheme anymore, I can empower designer to make that call, and give him the values and the values in regards to what we want and then to be empowered to then to not get in the way to get into the next stage of saying, Okay, now you have multiple products. So you need to talk about the right questions, these products need to answer and you can’t even wireframe it, you can’t talk about the screen you need to say. In this quarter, we need to have these products on these features, rather do this. So I want a better one a better experience to manage permissions if you’re an enterprise software, and it should look like this. And these features have ability to have read only here, write only here to be able to have enterprise controls, and they can’t see this they can see this screen from different levels of organization as an example. And it should answer these questions. It’s creating use cases and user stories in regards to what features they should ask as call it a phase 2 to versus actually wire framing out. Right, exactly the thing

CK LIN 1:01:37
focus on the the the forest rather than a specific tree.

ROSS MCCRAY 1:01:41
And then you go to the phase three, whereas now you have to just talk about the product and say, Hey, in the sprint in this in this quarter, the product needs to be able to support hundred customers, you know, 10 times the amount of customers that needs to be able to add more value and save your clients money, for example, then then then having the team be able to figure out which features and then what what what features, what questions, we should have to answer what they do. And then the wire framing and the color palette to then even going further talking about the entire portfolio from a revenue perspective. So that so this is an example of going from making a decision of the color all the way to a company goal and empowering and SVP to a VP director to a manager to the team to make those individualized decisions.

CK LIN 1:02:28
So let me actually ask a more and more of an internal game question because you’re you’re very hands on CEO you can get down to the trenches. Yeah, with the guys easily the right colors and deadline. Y’all know that with a specific engineering choices right on that, right? So my, my guess would be how does it? How do you cultivate this trust in your team? Because you may be able to say to yourself, like, Hey, I could have done that even better? Why did you make that choice? Right? So then so then but but part of the your mental game that needs to be changed is well, then I delegated

ROSS MCCRAY 1:03:09
So that’s exactly what that’s the last question like two or three questions ago. That’s exactly the challenge that i’m saying is hard to do. You never know, at which point you want to delegate and hold them accountable versus saying I want to make the so let me just answer the question with a question. And there’s no one size fit all. So don’t ask, it’s just you have to every time try. And there’s no framework that I’ve come across to solve this. But when when anything comes up, you have to make a decision, either entrust my team, give them as much context and set up what success looks like. And let them go out and do that, when you may have a probability of what that’s going to look like. And it’s going to be successful or failure. Versus saying I’m gonna have to make the call, do it my way versus do it their way. And there’s a lot of pros and cons, but simply said, the the the, let’s say the pro of making your own call, may be that you have a higher chance of success in that individual one time discovery, this feature maybe better this particular function, maybe if you’re if you’re truly are more qualified, right, versus letting your team take stab at it. And let’s just say you have as individual was the founder, CEO, you may have 90%, because you know, the customer better, you’ve been doing this longer or whatever, versus you team as a 65% chance of success for this individual function. That 65% if you continue to make your own call, your team will never be able to learn from their own mistakes, and reorient that which is very powerful. So maybe that 65% goes to failure, you saw that you could have stopped it but you decided not to so that that team can learn. And then the next time it goes to 70-75%. And you have the right framework and measurement of success and accountability, where you checking in on a weekly basis and say, Well, what happened here, right? What did you learn from this? How do you make this better? And you have to hold them accountable to that process? And sometimes, there are decisions where are too risky, that are too and that are how do you make call because the benefit of your team learning from a very big fuck up is very valuable if they learn from it.

CK LIN 1:05:29
It’s not a fuck up if they learn something from it

ROSS MCCRAY 1:05:31
well, right, but what are what are the lethal fuck ups and what are fuck ups that you can take a hit from? And what’s that continuum. And every single decision you make is different. And then you don’t even know what can be lethal, something that you thought wouldn’t be lethal, they can, they can screw up some other thing that you didn’t know could happen. And it could be a big fuck up. So you have to make a gut check. With all the data you have is a risk call, say long term versus we can’t afford to do this. And, and that’s the bit in my opinion, that’s a very large burden of any leader is you have to know when to entrust your team and when you make the call. Because you can’t always make the call. And sometimes there is just too much on the line to have it be a learning exercise.

CK LIN 1:06:24
so one of the angel investors that I talked to, and he’s a super Angel and he recommend to entrepreneurs or aspiring entrepreneurs to think probabilistically. And I think everything you just said actually demonstrated really well 65% chance of winning 30 percent etc. So how does one go about training oneself to think probabilistically?

ROSS MCCRAY 1:06:48
Well, it’s just trial and error yourself. It’s like 94 to 65. But how do you know of right percentages versus it being hit? you can go the other way. I’ve seen other people that think they’re 90. And they’re really at 40 and their team that 70. But then they have all this ego in the way, or they think they’re making the right call. It’s like no, you’re not you’re not you don’t know what you’re talking about. And you see that and you have teams everywhere in the world, where their manager, they don’t trust the manager, they don’t make the right calls. And you know, they they don’t they don’t believe in it, the CEO get so far removed from what’s actually, you know, in reality of what the actual is going on the business and I’ve seen, you get so much complaints about that. So it just depends. So before that, like the probability is you have to just have self awareness, and you have to let your ego go away. And you have to go looking at the hundred decisions that happened in the last two weeks, and make a model. And every day orient yourself. Just risk management, trial and error.

CK LIN 1:07:46
How do you not let your ego get in the way because you’re obviously a very confident person, you believe in yourself, you believe in the people that you surround yourself with?

ROSS MCCRAY 1:07:53
it’s very easy. Easy, it’s very easy. Okay, need to set up measurable goals, and you AB test. Bottom line, what does success look like? you draw it out. You write it down? You try it two ways, you come back and you see what works better. If your ego is more successful every time then great. Let your ego get in the way. Who cares? If you’re egotistical? If you’re driving those values and you’re adding more value to the customer? What’s your goal? In optimize the input? Set the output optimize the input?

CK LIN 1:08:34
Okay, so let’s let’s talk about perhaps maybe not in the business sense.

Maybe on the personal sense when you deal with your, your loved ones? Sure, your wife, your parents, right? These are, you know, people say you think you’re enlightened, and spend a weekend with your parents as an example. How do you make sure that you personally, your egos are not engaged when you’re especially interacting with people that who are really important for you?

ROSS MCCRAY 1:09:03
Well, so I mean, when I say let your ego get in the way, what I’m really more saying is, let the best tactic win. When I am referring to ego is your opinions, right? When people say egos getting in the way is when you’re truly are optimizing for your personal self gratitude over the best outcome. That’s how I see it. I see. So the point is the fact of measuring and output and being measurable driven, I see is the is how you get that out. Because ego gets in the way, when you make a decision that truly isn’t the best outcome I see for some other alternative reason your feel good. I see. So if it’s not your idea, and it’s someone else’s idea, but it’s been achieved, the better desired outcome, then you’d have to go with that input.

CK LIN 1:10:02
I see. So let me let me make sure I understand what you say. So basically, you said you’re running experiments had a clear defined outcome that you’re looking for. And then option A option B, whichever, whether it’s coming from your selfish intentions, or other people’s input or whatever, right? Whatever hit that the outcome that you’re looking for, right? That is the right focus

ROSS MCCRAY 1:10:23
Focus on the output and choose the right input, and do that. And that’s the point, when ego gets in the way, you’re bringing some of the input into the formula. Well, this was my input. So even though is less of an output. I’m going to still choose mine, because it’s my idea, right? Because this is how I feel or this is because it makes me feel better. Like who cares? It just depends if someone’s focusing on the input or the output, and you have a clear defined, desired outcome that you’re trying to achieve. So it’s a it’s a mindset. Do you go into the situation thinking about the tactics or the outcome? Do you say, Oh, I’m trying to do this? I’m trying to go into more time with my family, for example, right? Why do you want to spend more time with your family, that’s that that is a so I’m going to spend, I’m going to come to work, I’m going to leave work an hour earlier day, to spend two extra hours of my family or whatever, three to two extra hours or two hours to get two hours. That’s a tactic. If your family tells you leave work. come early. Spend more time with me. And you go, I gotta some more time, my family that is a tactic that’s an input, right? What are they trying to deliver? You’re trying to get in, I’m going to give an example. What I think is very common. People get people thinking about time, as it turns an input, the output is relatedness, it’s experiences. It’s a shared clinic quality. You know, bonding with time, mindfulness with your family, something that you can really special, you know, there’s always those dinners where you’re just quiet, no one’s talking and you’re just eating and you go as mother phone, you’re watching TV, it’s like you left work two hours early for what did you get out of that, that if anything that’s a negative, like, the more time you spend with people that is it really valuable and isn’t really impactful or deliberate is not only not adding the value you want, but could be seen as a negative, right? You’re getting desensitized. Versus, I’m going to spend every minute very deliberate, and I’m going to be present and not going to be on my phone and not gonna be taking your call. And when I’m home home. And I’m going to give it my all and I’ve seen very successful entrepreneurs, CEOs, women and men that are very busy. and are able to say no to the the the easy inputs. And are saying but you know, look, maybe I’m just using time as an example. And it’s not always the way it is. But it’s easy to it’s easy. One of my pain to articulate. I’m going to stay late Friday night, to get out all the stuff done, because I know it’s going to pop up on a Saturday or Sunday, or I’m going to come to work early on a Saturday. So I can spend the second half Saturday and all day Sunday as an example. Or where I’m going to do a work trip that I get home late Saturday. So I can be you know, home on Sunday versus spending Saturday and Sunday, and you go to your kids game and you’re on the phone and you’re not really watching. You’re not engaging, you’re not coaching or you get emails coming in, you got to take fires out, you’re leaving. That is you’re there. But are you really there, right? You’re there but You’re not there. Right. So to me, I’d rather spend five hours of quality. Like you remember that weekend? Yeah, you remember that weekend and there was an out desired outcome of building a bond building a relationship. learning together, having an experience together is to me it’s memorable that you hold dearly to yourself versus having 10 hours of just a mindless activity or not really, truly being present.

CK LIN 1:14:07
What are some of the hacks or the tips to really help? You know, let’s say let’s use that family as an example. To help make those shared moments memorable with their spouse with their children

ROSS MCCRAY 1:14:20
to me, It’s the same thing. what are you trying to do with your family, have a real have a conversation with your significant other and understand what you guys are trying to do? You go home and you put on Netflix for three hours, four hours, okay? If that’s the intention is to sit physically, next to each other, and to not speak to each other and to be silent and to just be watching a TV screen without moving and just ingesting information, if that’s your outcome, and that’s how you want a relationship, great. Define that and go spend all the time TV together.

CK LIN 1:14:59
I got you.

ROSS MCCRAY 1:15:00
If your desired outcome is I want to have a meaningful spiritual relationship, I want to be able to build something together, I want to give back I want to give charity to someone, I want to be physically, you know, healthy with you, I want to be healthy together. I want to grow each other. I want to build something, either a business or charity or a foundation together. I want to teach children together. What is the purpose of your family time again, it’s the output, then optimize to that same concept.

CK LIN 1:15:34
To you and your spouse have regular conversation about this?

ROSS MCCRAY 1:15:38
Yeah, yeah. Is it? Yeah. Is it? Is it a monthly, weekly quarterly? Or is it just kind of happens? It happens. It’s a mindset, right? It’s not a it’s not a scheduled routine up? It’s the 28th? Talking about it? No, not at all? No, yeah, we don’t want to make a transactional business oriented. But you want to always be there. And you want to ask yourself, What are you spending your time? And again, it comes to the same part with, you know, with your friends, and how you value your friendships? How fast can you get to that shared understanding? And how quickly can you get to be mutually adding value together? If you go to if you gotta sit down for 10 hours and say, Okay, let’s, let’s talk about everything. Let’s talk about outputs and inputs our time together, and that gets tiring, you know, you can invest in it, do it. But I hope that you have a relationship that you don’t need to do that every week, or every month, hopefully, you can spend 40 hours, 80 hours building a foundation and having a shared understanding. And then you’re spending time optimizing towards it. So it’s getting to a understanding of why you’re doing what you’re doing is purpose driven. Intentional output focus vs. input.

CK LIN 1:17:01
Let me use this example. You know, I used to play the piano. So in the beginning of learning piano, I learned very mechanically, you know, the keys. And hopefully right after some time, you get to really use it as an instrument. So you can now effortlessly use it as a way to express your emotion. So maybe I’m asserting you tell me this is the mental model. What it takes aspirationally is to go in flow and have conversation and mutual understanding very quickly. Yeah. But perhaps in the beginning is the scheduling. I think so. Right? I think so. Then Then once you find your cadence and simpatico all together, then it becomes a lot more I think, some mutual understanding. Change of topic: what do you thing is like to be a man in modern times? Let’s bring that in, you know, a little bit more about the purpose of this podcast, because most of the audience members going to be men.

ROSS MCCRAY 1:17:59
Yeah. You know, it’s a it’s a, it’s an interesting one. It’s an interesting one. I don’t know if I have a strong opinion from a gender point of view. Okay. I personally do not have clarity on it. And I struggle with this concept. So I’m not going to give you my opinion, because they have long opinions. But if I don’t have one, then you know, I don’t have clarity here. So I’ll, I’ll, what I will do is I will respond to your questions with why I’m confused.

CK LIN 1:18:35
Okay. Sure.

ROSS MCCRAY 1:18:38
So the concept of diversity, the concept of equality, I don’t see it out there. Right. I see a lot of discrepancies in this concept. Whereas people talk about equality, but they really don’t want equality. People talk about diversity, but then they don’t really act on diversity. And, and sometimes it just gets taken too far. And there’s certainly there are differences and genders, and you have to respect that. But there’s also it’s like, where do you draw that line of equality? Like I saw a group of men rioting or whatever, recently in LA, i was driving by talking incredible about how it’s not, they were very upset that they couldn’t give birth. But yes. And they were talking about how there’s no equality, they were fighting for equality. And they were very upset, and they cannot experience this beautiful relationship of giving birth. I mean, they seem pretty serious. Wow. So it’s interesting, right? So let’s, let’s just take that interesting point of view. So clearly, there’s no equality, man, female, there’s a biological difference there. Correct. So but when you’re fighting for equality, what is equality? Right? But equal? want equality across all gender? We want equality. Well, what where do you draw the line of what is eligible for equality, and what is not eligible for equality? And that’s where I’m confused. And that’s where I’m confused, where it’s like, people want you to speak to the same people, the same way woman speak to women very differently. Whereas women speak to men. In groups, not not always the case. But I’m saying in general, men, I can tell you from experience, speak very differently to men than women speaking to a woman. Is that equality? Can you talk very manly, bro-like, and whatever the case, you know? So one should say, Okay, well, then you shouldn’t do that women shouldn’t speak to men differently. And I’ll use stereotypes they shouldn’t gossip about people very differently. men shouldn’t be talking bro like in the locker rooms together? And that, you know, you shouldn’t have that differences. And you should all speak about the same thing. But like, that’s where I’m confused is, what is the difference? Where do you draw the line? Where don’t you draw the line? To me when I think about just even being conscious about a gender, and even thinking about, oh, you’re a male, you’re a female, let me change. That’s where I don’t like that. The fact that you know, and like say a diversity thing at the company, the fact that some programs, they say you need to have more diversity, say on a more females and leadership and more people in the board, stuff like that. Whereas I agree, you should have more diversity. And it shouldn’t be a boys club, these kind of things hundred percent, I’m aligned. But the tactic says, now go fire, a team of people if they were most qualified, potentially with that, and to bring on arbitrary gender distribution, just because we need to artificially force diversity. And it’s not because the best intention, right? I struggle with. But then you have this concept of Well, there’s so much unintended bias is so much subconscious bias that happens. So in theory, that sounds great Ross, but I’ll never happen. Look at what’s been going on. So you have to bring in these artificial things. So it just for me, I don’t I don’t want to, I don’t want to have to deal with the situation differently. Given the gender. I don’t see a reason why you should. I think that it, I think that thinking is what actually causes the problem. But on the flip side, I get how that’s happened over the last hundred 220 years. And we’re here because of that level of thinking. So again, I don’t have an opinion. I don’t know the answer to this, I struggle with what it means to be a modern man or what it is to be a female and the differences and what is eligible for that. And what is not.

CK LIN 1:22:53
Yeah, the whole point of this conversation really, is to inquire about what that is, and for us to heightened awareness. And from that, you know, we grapple with these questions individually, then from that, then we can make decisions, hopefully, right from our highest self the way we articulated

ROSS MCCRAY 1:23:10
Yeah, for me, I think it’s I also think that’s a tactic I think, don’t try to bring in bias. Don’t try to separate genders, or even worse, you know, races into certain things, and the combination of gender race, and you know that all these aggregations, try much as possible to just think about the outcome and the best intention and will let whatever happens happens, that means all female, that means or male, that means a 5050 split exactly, just, I’m hoping by putting the best intention forward and not being biased that over time it will become, it will become more balanced, integrated in a healthier relationship.

CK LIN 1:23:53
So let’s do a little forward looking for a moment. You’re a technologist. Yeah, right. You run a companies, you start companies. Yeah. You have a life purpose of alleviating human suffering. Yeah. Right. So how do you see the the role of technology to help with that? Because to me, technology is a multiplier. Whatever the intention.

ROSS MCCRAY 1:24:12
Yeah, so here’s how I think about it. I’ll give you an example of how technology, I think there are some ways where it becomes an enabler and some things it becomes inhibitor. And we’re going down a very risky road, in my opinion. So let me give you this example. So a few years ago, I went to Tokyo, Japan, and other places in Japan. And at the time, there wasn’t a Yelp. So I’m very used to, I’m hungry, I’m looking for certain type of cuisine, I’m going to go on Yelp, rank it by most commented, and then look at the places and then to find them area and listen to GPS, and I’m going to do an Uber driver. It’s incredible, what a time to be alive. From a technology, friends, I can find the best restaurant without talking to anyone I can, I can call car to compete me up with a minute to the every location that I’m in taking me there. And you know, it’s like magic, right? And it’s automated. And you don’t have to say a word to anyone, you don’t got to think about anything, just boom, boom, boom. And look that’s incredible for its own for its own purposes, and I’m a power user of stuff. But so when I went to Japan, when I didn’t have that I had a panic and like 60 seconds, what what, how the fuck do I find where to go? Like, what do I do? How do I know? Some of them? like, Well, fuck, I guess I gotta have to just talk to someone. I gotta ask around. Yeah. And then when I asked someone, it was like, hey, just go down, turn right, turn left, and go explore all the restaurants a bunch. It’s like, Whoa, what a call after half and look around. And that took me on an interesting journey. because it allowed me to look around, it allowed me to speak to people, it allowed me to look around my environment, and to be headed to bring in more senses, to be thinking about interacting with other humans and nature. And I started bringing more attention to like the beautiful trees around me because I’m looking at not just dialing and falling, turn left, go right, do this, and I’m just on autopilot, I’m gonna go on my email and send an email out. And you’re just in your focused on the interaction in you that and you and you speak and people and you have small talk, and you have this banter. And there’s some value in that human interaction that face to face person in person interaction, the exploratory of looking around the world and going in a way. And that was that really stood out to me. And that was because I didn’t have technology. Right? So that exists. So I want to bring back to your question. And for me, technology has a choice. You can you can engineer your design technology to either say, stream like eliminate human interaction elimiate, just automate, and obviously can trust me, you know, me, I love this shit. More, more than most people talk about automating all these foods like that, but you but you have to also understand the cost of what you’re giving up. And I don’t think we think about it often as a society. I don’t think you think about the cost of what this is like. Some there’s been some discussions around AI and how there’s a million times more investment towards developing AI than it is thinking about the societal regulations, and what it can mean to us protections that it can bring on a downside that kind of ebbs and flows, checks and balances, and it’s out of whack and the investment. So point is, I think technology in the future, hopefully will become more of an enabler to allow you to have a better human experience. And not just I think they did the years of just focusing on automation, like, can you automate a better user a better experience? Can you say you go through turn to left, and if you want to explorers is a great place, talk to people? You know, I think that’s an example of where I see technology, hopefully.

CK LIN 1:28:03
Yeah, there’s a lot of design choices we could make. To enhance, you know, once again, going back to that is the maximum is the optimal, right. And it’s in the design is the minds of designers to make that choice. Right. Right. Cool, man. Well, thank you. So one last question. Okay. So would be people who are listening to this, yeah, will be one thing they could do tactically, if they’re inspired by your worldview, is they’re inspired by your narrative to become a better man, better husband, better CEO, better entrepreneur, better human being.

ROSS MCCRAY 1:28:43
Yeah, I think just I think summarizing, some as I was talking about, I don’t need to throw out a new concept. Sure. I would say have have it write down and have clarity on why you are alive and whatever you think it is, asked yourself five WHYs deeper to why your life, write down and ask yourself, why isn’t this and then broaden your answer, and then ask why is that in all the ways five times. And that would be, I would say, one tactic that I would do. And the second is going to be looking at how you spend your last week, break it down, and see how many hours that you spent against that fifth why, right? And then see how many and then and then verticalize, your other hours, and see how it was spent. So you look at how much of your time and energy you’re spending towards while you’re alive versus other things. And then after you have that clarity archetype, some tactics and outputs that you’re trying to get maybe it’s a shift 20 hours more into my mission or eliminate these hours these ways and write those measurable goals check in every Sunday night and see how did we start with those three things?

CK LIN 1:30:03
It was a really acknowledge you for sharing everything you shared, you know, you did not disappoint. You always, always always a pleasure talking to us. Yeah, I appreciate that. And I hope the people who are discerning really learn a lot from you know, Ross’s mindset and he’s so generously share these tactics, how he managed his own lifestyle in order for him to be so productive at such a such a young age. So go take some action and follow Ross this week.

ROSS MCCRAY 1:30:30
Alright guys, thanks. All right.

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