All Posts
About
Join The Conversation
Subscribe
May 25, 2026
04 Rhett Woods - Honest XD Podcast
04 Rhett Woods - Honest XD Podcast
00:00
33:18
Transcript
0:00
[upbeat music] Hey, good to see you again. Um, I'm gonna tell you a little bit of a story about my, my guest this week, starting back a little bit further.
0:10
So from two thousand and seven to two thousand and thirteen, I had my first, uh, startup failure, first corporate experience, which was around the Bear Stearns collapse. Absolute disaster.
0:20
And ultimately then I started running a small digital agency, and one thing led to another. That's, that chapter of life came to a close around twenty thirteen, and that's when I decided to get into the product space.
0:29
And so took a job at a, uh, small tech startup in Chicago. It was, like, employee number eleven. And over the course of a couple of years, went through a few acquisitions.
0:38
Uh, got acquired by a company called Rally Health, and then was ultimately acquired by UnitedHealth Group.
0:43
And along that way, uh, I met Rhett Woods, who was the chief creative officer at Rally, and, um, got to be part of Rhett's team for, like, five, six years. Got to work on some really cool things.
0:53
Um, if you've ever been a UnitedHealthcare member and have used myuhc.com, um, our team was the, the team that built the experience behind that.
1:01
My little part of it was the individual health record, uh, which was a pretty cool thing to do the first version of. But anyway, Rhett was one of these guys that was just super high, high-achieving operator, could do
1:11
big level creative stuff, and also had really, um, amazing business acumen. He would talk at the UnitedHealth Group shareholder meetings. And so that... He was the first guy that I worked for.
1:18
I was like, "Oh, this is, this is what a, this is what a high achiever looks like." It's been good to keep in touch with him a little bit over the years.
1:24
I reached out to him, and he was happy to reconnect, which I was really grateful for. And so had a good time catching up with him. Uh, we covered a lot of ground, and I hope you enjoy it. Justin. Oh my gosh, man.
1:35
It is so good to see you. Good to see you. Thanks for jumping on. I've been looking forward to catching up with you for a while.
1:40
It's been a while, and when I started seeing what you're up to, I was like, "Oh man, this is really cool to see for sure." Cool. I appreciate that. Yeah. My, so my, my goal, like I told you in the emails, I'm,
1:51
I've been going through a lot of, like, paradigm shifts, and I know I'm not alone in that just 'cause of the people that I've been hearing from. Yep.
1:57
Um, and so, like, when I think about there's all different flavors of creators out there, and that's really who this is for.
2:03
Um, people that are, you know, making stuff, building stuff, creating things, and they-they're either facing kind of a crisis of like, "Oh my God, the tools are making it easy for anybody to do this." Yeah. Or, um,
2:16
and what, why am I doing it? Am I doing it for money? Am I doing it for purpose or for meaning? And so that's what the whole project is about.
2:23
But honestly, like, in, in order just to kinda like get caught up with you, I'd love to hear just kinda what you've been up to. Like, how...
2:28
When you, when you show up at a dinner party or something, or you meet somebody for the first time, like, how are you introducing yourself these days with all the different things that you're up to?
2:36
It's interesting because right now that I'm building existence, I don't talk a ton about it just yet. And, and part of it is because I'm not ready to talk too much about it. In this conversation, I'm happy to.
2:46
But what I mean is, like, I'm one of those people that once I turn over something I'm working on to let my wife try it, is sort of like the milestone where I'm ready to talk about it.
2:57
Um, because she has a very critical eye for technology. She's not into technology whatsoever.
3:03
And, and as you probably know me, I, I always have tried to create things as simple as possible for people, and that technology should never be a barrier. It's an enabler, right?
3:13
And it's, it's a way to connect people to processes and, and, and, um, potential outcomes or whatnot. So I am very vague to answer your question when I go to cocktail parties.
3:24
And funny enough, I actually don't talk about work that much. Um, I tend to talk about other things that are, that are going on. I'm curious, like, what those things are. Like, what are the things that keep surfacing?
3:35
Well, so I... Over the last couple years, a friend has roped me into, um, some scientific work up in the Arctic, so sometimes I'll be chatting about that.
3:42
I'm going back in, in, uh, July again for my third trip up to Devon Island, which is the largest uninhabited island on planet Earth.
3:49
It's way up near Greenland, near the North Pole, about nine hundred miles from the North Pole. And, uh, it is kind of this extreme situation, but at the same time, it's trying to help earth science primarily, by the way.
4:01
It's not even space science. Space science is a part of it, but it's actually more about helping earth science.
4:06
So I think that's a long way of saying whenever I have a conversation at a dinner party or cocktail party, I think people come away more confused about like, "What the hell does this guy do?
4:13
Because I thought he was in software, and then he didn't talk at all about software." Uh, and so it's kinda all over the place.
4:21
I, I will say with the right group of people, though, I love talking about what we're doing at Existence. I think it's also really, uh, connected to probably what you're going through and what I'm going through.
4:29
There's also, I think, like our age is part of this, this whole experience we're going through. There's like this cataclysm of things happening.
4:35
Our age is one of those things, and we're all trying to figure out are we, are we creating with purpose or are we just creating to make another buck or somebody else another buck, more importantly, right?
4:45
Is, is I think the vibe a lot of us feel. And then it's also just harder when you get to our age. Like, it's harder to find opportunities.
4:52
It's harder to get noticed or whatnot, which is crazy 'cause you've got twenty-five, thirty years of experience. Uh, and the tools aren't even the thing to me. The tools always evolve.
5:01
Like, to me, there's always a brighter, shinier object.
5:04
Um, but the best creators that I see out there, the ones that I follow, they just evolve along with the tools, but their creativity is within, and they're able to express it regardless of what sort of, you know, tools we're working on with them.
5:16
Yeah. Who are the creators that you're paying attention to right now? Who are people doing compelling things? Well, so I really like the guys at, uh, Secret Level.
5:24
Um, they're an AI film studio, and, um, they have been right at the forefront of this stuff. And Jason Zada in particular, he often posts on LinkedIn their latest projects, and they do a lot of AI filmmaking.
5:36
And he, he has a filmmaking background himself, so he's, he's in a very credible position to, to defend the, the transition that we're going through, the transformation we're going through.
5:47
He's in a very credible position to do so.
5:49
Unlike if somebody like a, let's say some nineteen-year-old kid suddenly started making films with no experience, we might all look at that with a critical eye and say, "Oh, you're taking a shortcut here because you never really had the life experience or whatever, whatever."
6:03
No offense to nineteen-year-old kids. That's not the point. The point is thatIn my view, really good creators, they evolve with the tools and whatnot, and these folks are building short...
6:13
The, one of their big ones is called The Heist, and they've made three different ones, and it's just a simple little six, seven-minute, you know, internet film series.
6:20
But it's the amount of work that went into figuring out how to use the new tool set, and for those of us that were using AI to create imagery or video in the earliest days, we know that things like, um, character consistency was, like, this huge issue in the early days.
6:34
Like, I couldn't keep the same character from scene to scene because the AI kept, like, regenerating it all, right? And you're like, "No, no, no, I want this character."
6:41
Um, and they've kinda like figured all that stuff out and just done a bunch of beautiful work. Um, so that's, that's one example, so I- Yeah, I'm gonna have to check that out. Yeah, yeah.
6:49
Check 'em out on LinkedIn and/or, um, their website for sure. Okay. Okay, cool. They also did the, they did the Coke ads, the Coca-Cola ads with the bear, and they were the first ones that did the, the AI Coke ads.
6:58
Oh, okay. Okay. And if you remember in year one, or if you were watching those campaigns, they got a lot of flack. Yeah. Yeah.
7:04
But the team there, they defended it, and they actually published, "No, no, no, no, let us explain how many humans were still involved in this process.
7:11
Let us explain how the humans play a critical role in production of these things, even if we're using new tool sets and new technologies."
7:19
And in the second year, they had a much better reception to the advertising that they put out, and I suspect that the third year nobody will think anything of it, right?
7:26
That's just the natural progression we all go through. Yeah. Oh, that's interesting. Okay. Well, now I'm, now I'm definitely curious to go check 'em out. Yeah, it's cool stuff.
7:33
So one of the things that I think about when I recall working with you is, like, you're just one of the most naturally energetic people [chuckles] I've, I've worked with and for, and I'm curious what that looks like.
7:44
I was thinking about this when I was walking my dog this morning. It was like, it's over 10 years ago that we started working together. So you've obviously gone through a lot of changes.
7:51
I've gone through a lot of changes. But, like, how do you keep your energy up? How, like, what are you doing on a daily basis to keep yourself sane? Um, a few things.
8:00
Like, since I first knew you, uh, back in the crazy, like, my late 30s, early 40s, uh, first of all, in those days, I drank a lot more than I do now. I basically don't drink at all, or it's extremely exceptional.
8:11
That's one big thing I do to take care of myself. Um, two, exercise is huge, and I really try to be out there five or six days a week doing something, man. It could be as simple as a Peloton.
8:22
It could be a three-mile run. Mm-hmm. I go to a trainer with a couple friends, by the way, like, a, and some of my, my friends are all my age too, our age. And so I'm going to, like, a personal trainer.
8:31
We call it CrossFit, but it's very San Francisco CrossFit. I would say it's more like body functional fitness type thing. Mm-hmm. But I try to make sure I'm exercising five or six days a week.
8:41
Um, and if I'm not exercising, go take a walk or whatever, because I found that that is part of my rhythm that sets the day in the right direction.
8:50
And if I've already, let's say, done a workout, dropped my son off for school, come back, and then I'm ready to go to work, I feel ready to go to work, and then I feel already accomplished on the day that I've done something for me.
9:02
Um, but I will say that that has been a huge savior for me from about 45 years old till now, and it's funny enough, I wasn't into fitness before 45 at all.
9:10
And now I'm, I wouldn't say I'm obsessive about it, but it definitely keeps me sane. And more importantly, I think, and it's somewhat related to what I'm building at Existence,
9:19
I've started to really look at the data of how I manage my time and my energy, and we- we're building a tool set to do exactly that.
9:27
Uh, and even when we're building the tool, and we didn't have all the things that we have now, I started to create a better awareness of, like, what's a really good week for me? What's a, what's a perfect week?
9:35
What's that feel like? What's that feel like inside, both at work and creatively, and family, and relationship, and physical health? And I've literally, like, at some point in the future, I could show you.
9:47
I can show you on a calendar the patterns that, that constitute for me a perfect week. Hmm.
9:53
And then we've trained the AI that we're building at Existence on our own time and reflection data, so the AI has our inputs about how we felt about the time that was spent and can play that back.
10:06
And just yesterday, I was kind of demoing it for somebody as we're building out these tutorials, and it knows exactly the things that make me tick between exercise, and the other thing it points out to me that's interesting is it's like you thrive on novel experiences, and then it lists all these experiences I've had in the last six months and how I rated them and how I reflected them.
10:27
That's a long way of saying I actually rate my time now when it stands out to the positive or to the negative, either way, right? Right. It's not always, like, rainbows and freaking unicorns up in here. Yeah.
10:39
Um, there are times where you have, like, a shit meeting or just a bad, you know, outcome of a project or whatever the case may be, and it's important to actually take stock of those things and recognize, like, what went wrong, and what was my role in that, and, and what can we do or whatever.
10:56
And I'm the kind of person that's always looking forward, so I don't need to dwell on, like, what happened. I need to dwell more on what are we gonna do about it differently the next time.
11:06
But that's a long way, again, of just saying
11:09
really being mindful of how I feel and then correlating that with data and then creating an understanding of, like, what is, what, like, a perfectly balanced day, what does that feel like, and what was it composed of?
11:22
Mm-hmm. And what was it composed of in terms of what I was doing, who I was with, where I was at? And, and all those things matter a lot more than we realize. Uh, so that's one of the reasons I'm, I'm fascinated by it.
11:33
Time management has been the thing that has evaded me, I think, for a while. And so, like, I know you don't necessarily know the entire story, but yeah, I left my full-time role in marketing like seven weeks ago.
11:44
I just, like, I got, I got so burned out. Yep. I just literally was like, "I'm out. I got no backup plan. I got no safety net. I got no nothing, but I can't do this anymore." Yep.
11:54
And so what's been interesting is I found over the past seven weeks, I'm like, okay, now I'm my own...
11:59
I, I only answer to myself, but I'm still having trouble finding, like, how to get in the flow of, like, where I do my best work and how do I, like, how do I just personally set myself up for success and not sabotage myself by trying to do too many things?
12:11
AndEven before this call, like, uh, I, I knew this call was coming for like, you know, the last four hours.
12:17
I jammed a barbecue chicken sandwich down my gullet 30 seconds before I jumped on the call with you, 'cause I was just like, I was trying to keep doing stuff right up to the last minute. What has been...
12:26
Maybe it's the technology, maybe it's working with somebody like Rob or just being more close to it, but like how have you found that to be something you can do?
12:32
Well, one, I, um, one thing I've learned from what we're building here is how to set your intent for a day or a week in advance to really accomplish what you're trying to get done in that particular week.
12:47
So I personally set goals now at the weekly level. I just use an all-day, uh, like an all-day calendar event, and I drop my goals in there.
12:55
And then once I've done that, I plan out my week and I use the time blocking methodology. So I'll basically be like, "I know this is gonna be product work time.
13:03
I don't know what it is specifically yet, but I'm, I'm saving this space for this."
13:08
And then when I look at my goals, there might be specific calendar blocks, time blocks that I, that I claim and be like, "Oh, I gotta finish our policy document, so...
13:16
And I, and that's a heavy task, so I'm gonna give myself an hour here. And, and I'm also gonna put that hour in a place where I know I'm gonna be less apt to get distracted or to wanna run away from the task."
13:28
'Cause that's the other thing is like not all work is good work, right? Like it's sometimes you just gotta do the, the whatever work.
13:34
So it's kind of important that you schedule the whatever work at times that work for that to be. I think that's another thing. I think it's like we all have to know what makes us flow and when.
13:43
Some people are time of day oriented. Mm-hmm. Some people are, "Oh, I just shouldn't do this after a meal" oriented or whatever. But going back to your question, to me, I kind of map out a week in advance,
13:55
includ- and I start, by the way, with my exercise. So I start by claiming, like in a sacred way, these are the blocks of time that I'm going to exercise and I really don't wanna trade those for work or for other things.
14:08
Then I go in and I do my work alignment to the goals. Then I fill in any like personal plans or if there was already a personal plan, that would've been taken into account already.
14:19
But I guess on the weekly, I'm quite, um, structured now compared to what I used to even be, and then I measure myself against it.
14:27
But I don't really measure myself as so much about like, "Oh, did I trade a little bit of lifetime for work time?" I measure did the damn goals get done. Mm.
14:36
And, and this is with no project management at the company, by the way. So it's like interesting to, uh, have to force yourself through that kind of thing.
14:43
But I guess it's a long way of saying I think we all can create systems for ourselves, and those systems are probably comprised of a combination of a calendar, a spreadsheet, a to-do list and whatever.
14:53
It's just like what's the flow that works for any given person in those things. Mm-hmm. Um, and then I think lastly though, like knowing when you're going into something that like you're not gonna give it your all,
15:08
and knowing when to pull the ripcord and be like, "This task is gonna get, have to get moved," and not...
15:14
And it being okay to be like, you know what, that policy doc, for example, I can't get into it right now and yet I need to pay really close attention 'cause this is really important for the whole company.
15:23
I'm just gonna move it to a better place. But by moving it, I'm not changing the accountability of it, just changing when the deadline's gonna happen, if you will.
15:32
Like I keep the blocks on the calendar actually as a keep. I, I use a combination of To-Do and Calendar myself. Um, but I find time blocking big tasks is a huge, huge win, uh, even if they move. Mm-hmm.
15:46
If you, if you go back and like could talk to 25, 30-year-old Rhett, giving him some foreshadowing of the future, what are the things you think you'd spend time preparing for just given everything you've learned?
15:56
I think number one, for those of us that are involved in technology in particular, and I got my start even e-earlier than 30, 35. I've been doing this since like the late '90s, right?
16:08
And in, and, and I've been so proud and happy that all the things we've all worked on, including what we worked on together, and we should all be so proud about the things we worked on that are impactful to people.
16:17
But what I didn't realize is how... I guess I was naive that technology was gonna have this dark side.
16:23
And one thing I would've told my younger self was, "Watch out for where this stuff is going," because I always went into it blindly being like, "Man, this is gonna be amazing, right?
16:36
This is gonna be good for all the humans." Well, it's not. It's not good for all the humans. And there's a bunch of things, and I don't need to rehash all the things that we all know that are problematic, but it, it...
16:48
As somebody who's been involved in advocating and creating technology and creating this relationship between humans and technology, I will tell you there's a part of me that's been disappointed by it and wish I would've known where I could have seen into the future a little bit more,
17:02
'cause I personally would've done a few things differently. Like in my earliest days of advocating for technology, I was like, "Oh, you know, we don't need to get all up in this privacy shit.
17:11
Like, like we gotta innovate, we gotta innovate, we gotta innovate." Well, now I think that's a huge mistake for everybody. For everybody.
17:18
So I just wish I was more educated, uh, at the time about like how things would unfold. Now there's a lot of good too, by the way, like incredible things.
17:25
Life spans are increasing and, and, and, and information is faster and blah, blah, blah, blah, blah. So it's not like a doom and gloom kind of thing at all.
17:31
But I just, I wish I would've understood the pragmatic potential outcomes of what we were creating to be a stronger voice in my 30s and 40s in particular, um, to, to, for, for, for how this technology might be used.
17:45
And now, by the way, with the advent of AI or the, the coming of age of AI, I should say, um, this conversation is more important than ever.
17:53
And I guess it comes back to like understanding ethics and philosophy I think are probably the most important things right now in society,
18:01
because otherwise we're, we're just at risk of being really disconnected from one another. Um, I think the other thing, um, you do gotta kinda recognize when you're in-... movies that you don't wanna be in.
18:16
And, and you've, you've just recently gone through that yourself. And, and I actually went through it not too long before you actually, which is how I ended up where I am now. Mm.
18:25
Um, but it's recognizing like you don't have to keep doing what you think you have to keep doing. And going back to something you said a few minutes ago, by the way, about time management or whatever, that's like,
18:35
that's like the idea that time happens to us. Like part of what I've come to realize now that I'm 51 years old is that time doesn't actually happen to us. Like we happen to time in a sense.
18:47
And once we understand that power that we all possess
18:52
and the amount of choices we actually have, particularly in the Western, uh, societies that we have here, um, in, in these sort of wealthier countries that we, we live in, we have an awful lot of choice that I didn't realize back then in my 30s as well.
19:07
And then lastly, actually probably the most important one, it would be like, really don't waste time. I, I, I would, I would describe myself as a very late bloomer.
19:18
I did not really start to get momentum in my career and everything until about 35, 38, right? I didn't found my first company or co-found my first company till I was 45, which is by the way, normal and the average.
19:33
But when we look out in the world, we're like, "Ah, this 20-year-old kid here, 22." That's not the norm. That's the exception, including, you know, we all work for a very young founder at one of our companies.
19:43
That's the exception. It's not the norm. And so, but what we're trained through the media is this idea that like, oh, we're all gonna be beautiful and rich by the time we're 25 or 35.
19:53
No, that's just fucking not true at all. So I guess that's, um, a long way of saying kind of two things. One is just don't waste time or be aware of time more importantly, and then get away from the fricking media,
20:07
all of it. Like your, your community of people, that's your media. You know what I mean? So, and I got, I, I got, I basically stepped away from most media around 2019. Uh-huh. Never been happier for it. Same. That's...
20:24
Man, there's so many adjacent things that I'm fascinated by.
20:27
So one of the, one of the rabbit holes that I've gone down, and this is like a completely separate thing that I started doing, was I'm, I'm wildly intrigued by the idea of consciousness. Yeah, me too.
20:37
And it, and it comes back to time like you were just talking about. Yeah. Um, the, the amount of physicists and
20:44
scientists and neuroscientists like that, that I've been reading and listening to has been so much fun for me.
20:49
So I'm curious, like if you take another step down that metaphysical sort of esoteric path, what kind of fun stuff are you finding in that arena? Well, I, first of all, I'm a huge fan of this.
20:59
I, the, the older I think it's natural for all of us, the older we get, the more we wanna be introspective about, um, what's going on here, right? Like what, what, what, what's really going on here?
21:09
Um, and then what is our role in it? And, and then slowly unpacking the fact that, you know, the humans are not the protagonists in the universe.
21:17
Uh, [chuckles] we're, we're the, we're like, like a little tiny thing at, at, at best. Um, you know, for me, I, I, I think that, uh, uh, in 2019 I really dove into meditation.
21:30
That was a, that was a, a, a real net positive. It took me many years though to ever get anywhere near, um, what people describe as the benefits that you're trying to get from it.
21:41
I, I, I got benefits of being like less stressed or less like maybe reactive very quickly, but I never really got to the deeper states in transcendental, transcendental, I can't say that word, but anyway, in, in meditation
21:53
and I thought that that was a really good practice. Um, the other thing and, uh, being mindful of, uh, well luckily I'm not counseling anymore so I can say whatever I want but
22:02
I, I believe that psychedelics are the future of mental health is one of the big things.
22:07
And, um, I'm not advocating that people go out and just recreationally do psychedelics, but I do think people should, especially people who are going through major transformations in life and they wanna understand all these things.
22:19
To me, there's no better way to explore consciousness than through, uh, psychedelic therapeutic channels that exist. Um,
22:29
and I, those things have been tripped up and held back by bureaucracy and, and whatnot for a long time and, and fear and who knows a whole bunch of things.
22:37
Again, I'm not trying to cast negativity on any one group that's been trying to block anything, but I think for anybody who's of any age honestly, but I think when you get to be in your late 40s to your 50s, it's like the perfect time to explore these things if you're open to it because you can both go back and kinda
22:54
if, if you have past issues, you can kinda deal with those things if you will.
22:56
You can look into the future and you can, you can potentially even experience the most purest form of consciousness that you've ever experienced, right?
23:04
By just being in kind of a suspended state and understanding what it means to be truly present and connected. So that may come out of left field.
23:13
I wasn't really planning to talk about that today, but I think that's my honest answer which is like, I think that, uh, it's, I think it's the future of mental health care. I, I love it.
23:21
Um, I'm, I'm wildly intrigued by it.
23:23
I'm super close to a bunch of therapists just kind of at the stage in life 'cause my wife owns a counseling center so I spend a lot of time around therapists and there's a lot of really interesting conversations being had and, and outside of that setting like just the things that I'm reading, the people I'm listening to like Michael Pollan, you know, is one example.
23:39
Yeah. Um, so, so good and just kind of breaks up the stigma that I've been used to for a long time. Exactly. So I love that, I love that topic.
23:48
Yeah, it is and I just think, and, and especially 'cause I'm working on now, I'm exposed to a lot of more of the metaphysical world and I've definitely, I've leaned in.
23:57
I always felt it in myself but I didn't understand it. I've leaned into these concepts of like manifestation. I've leaned into these ideas of like the laws of attraction.
24:06
In some ways I've sort of tested them myself and I can tell you they work. Like, like it just, it's a thing. It's a thing. It's definitely a thing. Mm-hmm.
24:15
And, and it's all obviously connected back to energyAs, as like a core concept of how this stuff is transferred, if you will. Mm-hmm.
24:24
Um, and you don't need to explore psychedelics to even get to this conversation, by the way, at all. This is all just day-to-day stuff you can do.
24:30
Like you've probably heard of the black coffee thing that's been going around the internet or whatever, but like essentially when you attract negative thoughts or what you don't want, you're gonna fucking get those.
24:40
And when you attract the things that you're looking for, and that doesn't mean that people need to have a wish list of like, "Oh, I want like a jet and a fancy car." That is not the point at all.
24:48
The, the point is more like, I envision this for myself or my family or for whatever, because I'm trying to contribute this to society or wherever it might be. It's not a wish list, it's a way of being, right? Mm-hmm.
25:00
Explore I think what I've known, and I never could identify it, but I, my, my dad was a great advocate of the basics of positive mental attitude and, and, and just gave me all these early books on sort of the self-help category books in a way, right?
25:15
Mm-hmm. But there's a lot of goodness in those books, um, that are just trying to teach people the tools of, of the basics of that you kinda, you kinda attract what you're putting off, you know?
25:27
I think that's, that's a huge unlock that I found myself too.
25:30
That's like, it's like two hours of a conversation in and of itself, but I- it's refreshing to hear someone else bring, bring it up unsolicited 'cause I'm in a very similar place. Yeah, yeah.
25:40
No, I think it's definitely a thing and I, again, I think age is a part of it. We all get to this age and we're like, "Geez, what are we doing?"
25:47
Um, and we're at the, we're at the turn of a chapter, but it's like, it's like it might be the chapter that we're turning has some turbulence in it and we're like, "Goddammit, I don't know what to do," and you're still reading the last page and you're like, "Should I even go to the next page?"
25:59
Which is not short or whatever. I think it's really natural to our age is what I understand. I read this very easy-to-read book by Chip Conley, he's the founder of the Joie de Vivre hotel chains here in San Francisco.
26:10
He wrote a very simple book called Learning to Love Midlife, and it's more just this recognition that this is probably the biggest couple chapter changes we're gonna go through.
26:21
And then on the other side, for most folks who embrace it, it's, it's wonderful. I'm not there yet, right? 'Cause I'm still very much in, in my career. But, um,
26:30
I think conceptually a lot of the ideas that he laid out there, and then he also went on to create the, I can't remember what it's called, MEA, um, uh, but it's, it's for essentially middle-aged adults, uh, to go and have retreats together to understand, to learn from each other and whatnot.
26:44
Going back to community, man, I think that's part of it, is like how do we get back to community, community, community of friends, friends, friends? You know, I think I, I hate to bring up COVID 'cause it's just so,
26:55
so such something we all had to bring up so many, so many times in so many ways over the years. But it definitely marked us as a species and it definitely disconnected us in a way.
27:07
And I, and, and anybody who was paying attention to what happened to technology during COVID would understand that technology in the United States in particular leaped by orders and orders of magnitude.
27:19
And then if you travel to the rest of the world, it's not true. That like some places came up, but other places didn't really change at all.
27:26
And I'm not gonna name names 'cause I don't wanna offend different countries, but like when I travel to even, I'll just say some Western European countries, I'm like, "Whoa, whoa."
27:36
But it's okay 'cause it's just not in their value system to be able to click a button and have coffee delivered in 15 minutes. That's not their value system.
27:44
But here, because of COVID and, uh, social distancing, all these things, we're like, "All right, we gotta solve this in technology." And we did.
27:52
But in doing so, I think we accidentally further disconnected ourselves, right? Yeah. We didn't mean to. We didn't mean... I don't think we meant to. Yeah, that's a really good way of putting it.
28:04
We took a, we took the Big Mac approach to solving, to solving- We did... and here's where we are. We did.
28:10
But it made us more competitive on the world stage from a technological perspective, but it made us more disconnected as citizens. Yeah. This has been so much fun.
28:18
I do, I, like I wanna hear any other, any other stuff you wanna talk about when it comes to, um, what you guys are building. Like where it is, how people can learn more, like what you're excited about.
28:26
I know it's a lot to cram in, but- Yeah. No, I'll throw up some stuff for you later.
28:30
Uh, I don't have anything handy right now, but I think, you know, a few things, just parting thoughts I guess is, um, you know, I went through a pretty big change recently as well.
28:38
Uh, it sounds not too dissimilar to what you went through.
28:40
And part of the change that I went through was a recognition that in my case, I was in the sequel of a movie that I didn't wanna be in, is kind of the, the short of it. And I recognized it and I'm like, "Wait a second,
28:53
I've seen this movie. I know what this movie's like," and I had to really ask that question, "Why are you in this movie? Like how the hell did you do this?"
29:00
Because what I, like what I took away from it was I'm now a sequel character. Um, I need to go take bigger risks. And I don't mean bigger like risks, uh, financially with my family or whatever.
29:13
I just mean personally, I need to go take, I need to keep taking risks to keep myself honest that creating for me is a core part of what makes me tick.
29:23
And if I'm just creating something for, let's say another healthcare company, um, I didn't feel like I was aligned to what was gonna work for me.
29:32
And so I, and as painful as it was, I had to pull the plug on all that, and then was faced with the question like, "Well, what are you gonna do next?"
29:41
And going back to my opening comments about the Arctic, I found myself walking around with a shotgun protecting scientists, um, from polar bears while they were taking samples and whatnot.
29:50
There's no polar bears nearby, by the way, I'm just there to shoot them up. But it gave me a lot of time to think, and I literally made a list on my phone of like seven things.
29:58
Like, you could do these seven things, right? You're interested in these seven things. I ranked them, I force ranked them. And every single one led me to change industry radically from what I was doing.
30:10
And that's this chapter I'm in right now in existence. And my plan is, you know, really to get this company to where it needs to get, and in a few years from now force myself through another radical, uh, transition.
30:24
My wife and I are planning to move part-time to Europe, to Ireland.And, uh, even though I have the right to work up there, I've kind of decided that I don't really wanna be the tech guy anymore.
30:33
Like, I've done that 25-plus years. It's time to be like, "Well, could you be the education person, or could you be the, the... Can you help out the younger generations?"
30:41
I think is something that's particularly interesting to me. And can you find ways to still make money for your family too? So the health insurance, we got kids in college, like, we all got bills to pay, right?
30:49
And actually, arguably, it's actually the most expensive time of our lives right now, not the cheapest time of our lives 'cause our kids are in, in college. But I think the, the... Where I was going with that was
30:59
when you get stuck to creators, like I felt stuck and I felt misaligned, and I also felt really misaligned because we were building beautiful technology in the healthcare category, but the dis- distribution system in healthcare is so screwed up and broken that we, you can build the best product ever, but it's gonna take literally another year to get it in the hands of a few people.
31:20
And so I'm like, "I don't wanna do that anymore. I'm too old for that." Like, I'm the Danny Glover character, like, cracking my neck and being like, "I'm too old for this shit."
31:27
Like, I'm just not gonna, I'm not gonna do that, and I'd rather go Wild West and do something that I feel passionate about.
31:32
Thank God I found where I'm at now to be able to just get back into pure creativity and go backward in my career to be more hands-on again, right? Like, data management sucks, man.
31:43
Like, there's just no, almost no value that comes from that. The real value comes from being on a team of people and creating together. So for me, it was just, number one, a recognition that you're in the wrong movie,
31:56
and then, like, two, you have the choice to leave the movie, right? And then three, just go see what happens. Kind of like what you did, which is deeply uncomfortable.
32:06
And yet at the same time, I bet there's, like, thrill and joy that you get, and on the other side, I bet there's fear and anxiety that you get, and both are good and just, you know, managing those waves.
32:19
But like, even in what I'm doing, and I joke with Ron all the time, like on a Tuesday we're like, "We're gonna... This is gonna be the best product ever." And on a Wednesday you're like, "This is, we're all going down."
32:29
[laughs] Like, but I... That for me, that's what makes me thrive is the zero to one phase of creativity and the, "This hasn't been done before. We don't know how to do this."
32:39
And also working with a group of people that none of us have done exactly what we're doing before and letting that be our bond. The bond is we are all in this boat together in an ocean we've never been in.
32:51
So like, let's just work together and try to figure that shit out, you know? That to me, that's, that shit makes me tick for sure. That's awesome. Dude, this was so much fun. Thank you. Yeah. I...
33:02
Shit, it's been forever, and I can't wait to catch up in person. Yeah. I'll, I'll shoot you a follow-up note with some other things that, like you said, that I'm thinking about, and we'll stay in touch.
33:09
Yeah, sounds good. Good to see you. All right. Thanks, man. Take care. [upbeat music]
100 Conversations
Recent episodes
03 Abby Ross - What this 3x CEO is building for climate resiliency
May 15, 2026
02 Conor Lewis - Money, Meaning, & Making It Work
May 11, 2026
01 Sarit Sethi - AI, Parenthood, & Poetry
May 4, 2026
