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Below the Line with James Beshara on Smash Notes

#17 — Kevin Rose — The Man Who’s Seen It All

Below the Line with James Beshara podcast.

September 17

Kevin Rose is one of the most recognizable individuals in the startup world. As a founder, he and his team created the news aggregation site Digg, which became a household name, putting him on magazine covers around the world and creating an iconic brand in Silicon Valley — but it wasn’t a story that ended in champagne and ringing an IPO bell... As an investor, his list of angel investments is next to impossible to beat: Twitter, Facebook, Square, and NextDoor to name a few. 
He also was podcasting back in 2004 when the world was still just learning how to pronounce the word iPod... so suffice it to say, if he is into it, there’s a very likely chance it’s about to become a very big deal.
He is not only incredibly honest and open about his successes and failures, but he’s enthusiastically trying to get others to share just as openly. 
We go below the line on what it’s like to build something to hundreds of millions of dollars to then see it crumble, on how we tend to overcorrect after failure, the necessary side of experiences that help us mature, spouses and their integral part in the equation as an entrepreneur, and more. Enjoy this episode with the incomparable Kevin Rose.

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will, Hello, friends and listeners. Today's episode is a really special one. It is with Kevin Rose, who is one of the most recognizable individuals in the start of world. As a founder, he and his team created the news aggregation site Dig, which became a household name, putting him on magazine covers around the world and really creating an iconic brand in Silicon Valley with digg dot com. But it wasn't a story that ended in Champaign or a ring in AIPO Bell. So more on that and a bit as an investor. He is man. His list of Angel of Essence is next to impossible to beat Twitter Facebook Square, just to name a few. Pretty incredible. He also was podcasting back in 2004 when the world was still just learning how to pronounce the word iPod.

So suffice it to say, if he is into it, there is a very likely chance it's about to become a very big deal. He is not only incredibly honest and open about his successes and failures, but he's enthusiastically trying to get others to share just a CZ openly. So I think that's in full alignment with with this podcast. We go below the line on what it's like to build something to hundreds of millions of dollars, then to see it crumble on how we tend to overcorrect after failure, the necessary side of experiences that help us mature and we touch on spouses. And they're integral part in the equation as entrepreneur and a lot more below the line is brought to you by play Cast media. Do you want the easiest way? And I mean the easiest way to set up a professional premium podcast in your home or office. Go to play cast media dot com and get their premium podcasts in a box delivered right to you. Everything you need. All 14 15 different pieces, all the equipment instead of 30 40 hours of research of what plugs into what it is all sent to you at a price you can't be and comes with the info that guides you on setting it all up everything you need for professional premium podcast in your home or office. I'm recording this on play cast equipment and it is just It is the best out there, and it saved me straight. I spent hours and hours before just going with play cast to have everything work perfectly

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together. And you can check it out. It is, uh it just makes everything so straightforward. Play

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cast media dot com It's play cast media dot com And you can tell him, James Sr so without further delay, let's get into it with the incomparable Kevin Rose.

2:45

This is below the line. Kevin. What's up, man? Thanks for having me here today. Well, thank you for having ah, for having me over to stand on your stand right by the Embarcadero. Yeah. Pretty

3:4

Adam in town for a day, So I'm glad we got this actually worked out.

3:7

I know this could not be a better, better view. Maybe maybe in the world, it was pretty amazing. Amazing. Via San Francisco's beautiful from this side of the city. But I never actually never make it over

3:19

here. Yeah, I actually ah, I wanted in a interior room because for the noise level, and they gave me this awesome view room. So awesome. Up free upgrade. Most. Most adults don't have views like this. Amazing. The Bay Bridge from here, which is nice.

3:34

It incredible. That is I I actually, the only time that I see this whole scene is on. I did a little pellet on scenic rides, and and I do the Embarcadero all the time. The city that I live in all the time and it's gorgeous, but I actually never Yeah, probably twice a year. Make it over here. That is gorgeous. Um, well, welcome to the podcast. Thanks so much for dinner. We've got this episode's drink is a super special one. But also very fitting is my morning macho concoction and Caro's You're a big fan of macho. I

4:12

am? Yeah, I've been drinking much for a long time. Um, and it is a pretty unique form of green tea and that you're actually drinking the entire leaf. So it starts off as a tea called 10 Sha. And then it is, um, you know, typically ground up. Ah, and it turned into this powder powder type form, and you add a little hot water and whisk it and, uh, yeah, it's ah, it's a great tea. It's very packed with a lot of healthy inning and other things that compounds Elijah's toe could chill out a little bit. Right. Um, when

4:47

did you. How did you come across it in the Oh, cheers, by

4:49

the way. Yeah. Cheers, By the way, I'm way over caffeinated. Already do little things like that. He just took the whole thing.

5:0

Yeah, it's a little shot. Uhm

5:2

very weird way of drinking money. Makes another stuff in here. This is

5:5

not just your much Yes. Yeah, there's ah has quite the bite hunt. I know it has. And that's why it's a shot, because I don't really drink it for the taste. But it's, um yeah, this thing I started I was telling you right before we started recording, I think I started making, um, 56 years ago. And yet it's macho. And then some adapted Jin's some I ve to curb some mushrooms. And there's well, the lion's mane and, uh, and see to be calling.

5:33

Well, you did some cooling in there as well. How many milligrams calling to you?

5:36

Um, I actually this formulation, I'll have thio. I moved it around. So was Alfa GPC and then changed it Dessie to be calling. And, um, I don't know, off the top of my head actually. Have this. Ah, tell me this. Um Dr Dan Angle, who's ah, adviser like Alfa Brain s O. He's helped with the formulation. We moved it around like,

40 times. It's just his personal thing. Um, that, um I just got so much benefit from Mata then I loved adding, like, actual Gonda for De stressing me and then just went kind of hardcore into all the forms and online research and then gotten put in touch with, um with Dan who helped with the formulation after that. But, um, but do you, you know, crap done about new tropics and anti, but first on teeth, your tea master.

6:36

Yeah. So I I basically got into t in the year 2000 so quite a while ago, Um, it was New Year's, and everyone was kind of giving up something, you know, New Year's resolutions type thing. And at the time, I was like, Well, you know, I should probably do something that's healthy for me. And I just decided to stop drinking soda. And so I was like, Okay, at the time I was doing How old How old were you? Oh,

gosh. What was it like dating myself now? Um, at early twenties, kind of thing 21. Guess something like that. Um, and basically, I decided, OK, this is the time to do something healthy. I I gave it up. I was drinking a lot of sodas at the time. I was addicted to Dr Pepper. That was my kind of go to.

7:21

All right, Um, and then I had to Texas. I freaking love

7:26

Doctor. Dr Pepper, Mr. Pibb was also good. That was another competitors to Dr Pepper. But, um, yes, you know, I was one of those things where I needed that boost. I needed that. I need something cause I was getting caffeine. There was getting sugar there. So I need something to kind of, like, you know, kick start my day.

And so initially, that was straight up orange juice, like, just like give me the pure sugar. I like mainline that. So I did, um, the sugary kind of juices. But then quickly realized that I was just substituting something that was bad for me for something else. That was that was bad for me. And, um, just having that much sugar in anyone setting is not a good idea. So Ah, I thought let's try t you know, and I got into T as sort of buying at first.

Just kind of crappy store bought, bagged T, and I didn't really enjoy it. I remember thinking, like, other has to be something better. Um, And then I heard about loose leaf tea, and I was like, Okay, well, I'm gonna actually go to this tea store and talk to them. And they instructed me in terms of where were you? What city? We're, um,

after time was in San Francisco. And so, um, I just moved out here. And so there's a great place called Red Blossom Tea Company out here that I think has the best, um, tease. And you can also order. Ah, online red blossoms. Great. Great. So I don't have any affiliation with them, but they do. Um, some of the best imported too long tease come from Red Blossom.

So I realized while there's a whole nother world here, and like any proper geek, I like to go in and get, you know, go really deep into something and figure it out. Um, so I started Just like trying to understand the different regions, the different types of tea. Um, it's really interesting in that. Ah Camelia Sinensis. The main tea plant is actually, um, the same plant that creates all different types of tea. So Ah, white T who?

Long tea? Black tea. Ah, yellow t. Ah, you know, Where's Yeah? Agree? All the green teas. They're all from the same plan. She's just the process that is done to the leaf. So after the leaf. Ah, well, I should say it's a couple different things. One,

um, you know, how old is the plan? What type? What area of the plant are you picking? Is it just the, like, newly sprouted fresh buds from the plant? Um, or is it a 500 year old tea plant? Right. And and then after that, after you pick the leaves, um, you know, how are they being processed into being crushed?

Their being rolled. Um, and then when did they get fired to the actually stops the oxidation process. Um, and then, you know, then some. Some of them could be fermented, So how they being fermented like a pu EHR tea is an example of a tea that is fermented like wine in You know, you can keep parties like one I have some parties that I purchased in China, you know, 12 years ago, and I'm aging them. And, um you know, as you age them,

they become more and more valuable. So, you know, there's a little small bricks of pu EHR tea that are worth tens of thousands of dollars. Really, Mom, which is really crazy, but those air, you know, 100 plus years old kind of thing. And

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can you get I I remember hearing one time on white T You could have a semi drunk and feeling you drink enough of it. Um, that

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could just be I think that's a pretty much any tea. Really? Yeah. I mean, but But whitey is, um it does tend to some people say so. This is where it gets Really? There's a lot of, like, kind of pseudo science here. Like it. Some people say it has a lot of caffeine. Some people say it doesn't have that much caffeine. I do know one thing for sure. This is a fun little hack for people out there if you're thinking about having some caffeinated tea, but you don't want to have a ton of caffeine in like like great examples. This morning I had a cup of coffee.

And now if I want to have some green tea, the best thing to do is steep the tea for about 30 seconds and then pour off that first steeping because 80% of the caffeine is releasing those 1st 30 seconds of the Steve. And so from that point forward, you can continue to enjoy and have the the T cause it gets, you know, some high quality to you can stay poor five times, um, and and still get the great flavor but not have the impact of the caffeine. Yeah, Interesting. So anyway, I be studied. T I went to a university that teaches ti umm and took t courses. Learned about the regions traveled all throughout China, you know, fermented by,

um player cakes. It was always on the side. Or was there like always. When you're right, you're too. You're like I'm going hard into this. It doesn't take that long to become certified tea master. It's like, you know, a year year type process. So this isn't like a five year degree. Yeah. So you know, I went and, um, you know,

you learn how to cup tea properly. You learn different temperatures. They're required for certainties. Um, about the different regions. And ah, you know, you eventually start doing some blind tasting of different teas. So

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and you have the tattoo

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of Shinano? Yes. Ah, 3500 years ago. He is tthe e um, refer to is like the person that discovered t So Ah, he has, Ah, this kind of ancient text, that is, he was a terrible list. Essentially, that was writing all about these different types of her herbs. So, um, he's accredited to discovering, you know,

thousands of different herbs and one of the herbs that he mentions is the tea plant. And, um, that is the person that the Chinese attribute to discovering tea. And the Japanese say that it was a meditating, um ah, Monk that kept falling asleep. And this is a great, great start. Get falling asleep. And so he decided to cut off his eyes, right road into the ground in the tea plant. Grew from there. So it's a leader like islands. Yeah. Yeah.

So you can decide. Is that the islands that that was the true story or is it the herbalist, but yeah, So it's Ah, it's kind of fun thing that when I got sort of certified, I wouldn't had him tattooed

13:2

on my arm. That is so awesome. Um, and what would you say is your is your go to t each more actually zooming out you You also are a huge fan of fasting. So it sounds like you go pretty deep into what you're putting in your body or how you're treating, you know, the temple, as they say, Um, what are some of your favorite tease? But then also what? What's your entire morning kind of ritual like?

13:26

Yeah, so I would say that I go back and forth between, um wanted to dio aah! Coffee or wanting to dio ti Umm, I do love coffee. Um, it's for me. I've started, you know, doing playing around with roasting coffee beans at my house and things like that. So that's been fun. Um, but I would say that my typical day is based on the science that I've seen out there in terms of intermittent fasting and the one the one study that I really like is, um, everything was around 3000 women that had had breast cancer. But we're in remission. And they did one simple change and they signed up,

um, these women to receive text messages and you would text the service telling them when you had the last bite of food. And, um, you would then they would then send you a text 13 hours later saying it was okay to have your first bite of food in the morning and the women that were on this protocol of fasting just 13 hours. Remember eight of those hours or why you're asleep. So 13 hours of of which is super

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easy to do it like the other 11.

14:34

Whatever you want, just like delaying your the start of your breakfast by, like, an hour or something or two, maybe two hours, depending. Um, they had Ah, 30 I'm I won't nail. This number was either 36 30% Earth, 38% reduction in re occurrence of breast cancer, some pretty massive reduction in the recurrence of breast cancer, which they had had prior. So, you know, we know that giving your body a little bit of a break and some downtime to do repairs is a good thing. Now it gets crazier from their people fast for 16 hours,

18 hours. People do a monk fast, which is three days water only, people. D'oh! Five day fast now. And but the idea is that you're trying to create this, um, this the ta fa jee. This kind of like this idea that there are cells in your body that could potentially turn cancerous that if you starve them because they're already weakened, there are really a little messed up. They will die off first. And so you just have thio basically pull off the nutrients and do these types of fast to starve them often they're still in the horror medic response. Yeah, exactly. Well,

that's when you have Ah, when you eat something, that is ah, that caused that reaction toe happen. So, like, a type of plant. But but this is this is essentially, um, the the idea. We don't know that they're proper cadence for this. We don't know, Like, should you be doing the five day fast once 1/4? You know, no one really has dialed that in yet.

Um, but that's what scientists are working on. So, Walter, long ago out of USC is working on this, um, Satun Panda. Another scientist. Um, that's sort of the Salt Institute is working on a lot of this. Ah, specifically tied to circadian rhythms as well. So there's a lot of really, really kind of compelling science that's coming out enough to where I looked at that and said, Okay. Wow,

this is gonna help people. Um, I'm not sure what the right formula is gonna be for every individual, but let's let's start, um, you know, helping spread the message. And so, um, you know, knowing that I created a intermittent fasting app called zero, um, which now

16:36

has been covering his own screen. Great. Yeah, it's a simple Yeah, we have a bit. So hopefully

16:41

we have over 300,000 people fasting every single day with it, which is crazy. Um, so that's been has been great, but great apple, Watch out to Bo. Yeah, thank you. Very few

16:52

companies invest in that that side of things. And I, um and I love everyone that because I tried to leave my phone in a drawer first long as much of the days I can interest is the the watch

17:3

Yeah, that's Mike Maser, who's now the is the CEO who took the project over from me, has done a great job building that stuff out. And he built that apple watch app and it's very, very simple and easy years. Yeah,

17:14

and so the ah, the will and kind of zooming out from there. It sounds like the so many questions because it's and by the way, for listeners your wife is a scientist. So this is not just you're just cruising forums and coming up with this stuff. It's actually probably pretty well, um, well understood. And

17:35

the other thing, too, is I don't ever make any claims for anything like the best thing you can do is an individual that they're trying to talk about. This stuff, especially if you're you're not a scientist, is just to really read the papers and say, Okay, is there true, um, peer reviewed science here that we can point to and say This is kind of what we know. And it just knowing that, um, you know, you could have It's that old saying of like, strong convictions. But like loosely held like just knowing that the science can change at any point in time, but this is kind of directionally where we

18:6

think things were going right, right, um, and zooming out on just you weaken and we will touch on your career in tech. But it sounds like with tea with fasting, Um, where did your obsession on that side of things come from? And I don't know what the meta observation for that would be. It would be kind of like, um, optimization or or maybe it's, ah, you know, health span and Life span book. But where did the obsession on that side of things come from? Of giving up, giving up. So does a lot of people try that very few people because it's certified tea masters. Um, where did the that kind of seemingly peripheral obsessions start?

18:48

That's a good question. I think that, um ever since I was small, I remember just wanting to experiment with things, So I was when I was little. I I remember. I have the Nikes. My parents couldn't really afford to buy me the Nikes that would show the visible air pocket in the side because they were, like, expensive. You want to see, like the air on the side. Um, but it mind said Nike Air. So I thought that they were closed off so you couldn't see that, but they're less expensive. So I remember thinking like,

there's got to be in a Nike air pocket in there So I cut open my shoe. I found the air pocket and I was like, Whoa, it isn't here. And then I thought, Well, I need to be able to jump like Michael Jordan. So I like hot glued in some springs and in the back of the flat that I'd cut open and see if that would work and allow me to slam dunks. I really want to slam dunk. That looks like a big deal. So, you know, it was like I just always did things like that. My parents were not thrilled when I would ruin things, but I was always cutting things open and trying to figure out how things were working. And so I think that as I got older,

I just like I kind of would obsess over certain things, and that's not always been a good thing. I think that you can kind of like ruminate in obsess over certain things to a point where you're actually doing damage. Um, and that is that's scary. And so I have to be careful not to take it too

20:7
When did you go too far?

Kevin once experiences liver pain, and found that he had too many liver enzymes. It turns out that Kevin’s excessive consumption of sage, which helps eliminate stress, had begun to damage his liver in combination with alcohol.



far. What What is a project where you've obsessed a ruminated too much in its and it is, ah, suffocated the project. And then what's an example of the way

20:17

where Scotch. Three weeks ago, I started feeling really bad, like just like really sick. And I was like, What is wrong? Like, um, I had pneumonia before Ah, few years ago, randomly and I was like, Am I getting like that again? Like I need to lay down. I need to, like, sleep this off. And I was like taking naps in the middle of the day.

Call my doctor up and I when I got the blood work done, and I found out that my liver enzymes were like four or five x times the normal, and he's like something's going on here. We need to, like, check this out, and we went through all the different supplements I was taking, and I was trying a new wellit's. I was trying sage, but in supplemental form, which is like a very interesting compound in that if you take sage at higher doses, it's very relaxing. Kind of like what? VOC Opa does what you have in your drink here today. Um, and it just kind of chills you out,

Mills you out, and it's like, great. For I found it was great for sleep. That problem is, is that, um, long term use of sage will really damage your liver. And I was combining that with some other compounds that could potentially damage your liver. And it just, like, really sent my numbers through the roof and like, that's really scary.

21:23

And how long? How long have

21:25

you been taking state? A few weeks. Yeah, Yeah, but not every single day, but, you know, combine that with Okay, I'm gonna go out my wife and have a couple glasses of wine. And then that's also put taxing my liver and, like, you know, and then combine that with Ah, you know, I take a low dose, um, Staten,

which can mess with your liver. And so, you know, you have those three or four things together, and also it's a bad combination. You're really doing damage, so it's just like you know, I'm I've sensed dialed back the number of things that I take because I just don't want to push it anymore. I think it's I was getting a little too obsessed with trying to optimize

21:58
How can I better structure my diet?

Certain tools exist online that people can use to map out their genetic structure and plan their diet around their genes. Because of a genetic test he received from Ronda Patricks’ foundmyfitness.com, Kevin tries to incorporate choline into his diet to prevent memory deterioration. Focusing on incorporating all the colors of the rainbow in his daily diet is key for Kevin, so his lunch consists of various vegetables. Kevin also performs cardiovascular exercise frequently to combat his family’s history of heart troubles.



everything right. What is the What's today's kind of morning in nutritional regimen?

22:5

Well, I would say that s o I wake up in the morning and ah, I don't I will have, ah, cup of coffee or some type of caffeine. The green tea or something like that, like essential TIA tend to gravitate towards like Japanese green teas like a sentia, Um, And then after that, I have to decide. Well, I want to make it 13 hours. Regardless, that's like a bare minimum. That's pretty easy, right? So just waiting in an additional hour.

But I I have to decide. Is this a 13 hour day or is it a 16 hour day? Don't want to go 16 hours on fasting, and so most days ah, find a heavy meal. The night before, I might go 16 hours, but I try to go 13 and then for me, it's okay. My first meal of the day as typically, something I found out because I ran my 23 me in my genetic data. And then I exported all of that into, um, several different tools that analyze all of your genetic polymorphisms. That leg which fools? There's,

Ah, the Prometheus one. I really like Rhonda Patrick's two of the best so found my fitness dot com. You can log in there and you could upload your 23 me raw like zip file, and it will then analyze all the different, um, jeans that you have and tell you, Um, are there certain supplements you should be taking other certain things that you should be doing based on your genetic makeup? So that's awesome. It's pretty. It's pretty sweet. And one of the things I quickly realized is that I am a really bad absorber of coleene, and so that can lead to memory related issues that can really lead to a bunch of different things. And and so I try to get some coleene in my body, and for me,

that's that's eggs. And so eggs, hair just like filled with Colleen. Um, we brand also has a bunch calling. So if I'm going, not going to be doing eggs. If I'm gonna be doing a little bit of yogurt, all mix in some wheat bran that has coleene naturally in there. But I've been trying to say OK, forget high dose supplements. Let's figure out where there's ways to get this stuff naturally from our food's. So, you know, if I can have three eggs, Um,

I'm getting a pretty substantial dosa, Colleen, Um, right away. Ah, and is making

24:9

me want to use the beauty of, ah, modern tools. I'll look up the exact dosage of CDP calling. Just get your take is for listeners. This is an expertise that ah, beyond t that Kevin has, um, in this room or at least knows more than the average bear. So let me actually look it up is you're talking about

24:29

Yeah, right, So So that's kind of like if I can check that box, I feel pretty good about it. And then from that point forward, you know, I've already had my dose of protein. Um, that's great as well. In terms of that, I like Thio. I'm not a fan of a huge high protein diet, but I do like to exercise and work out and So I would like to have some supporting protein there for that.

24:49

Um and they have, like, a protein goal each

24:52

day. Not really. Not really. If I I just try to be mindful of how much I'm exercising. And if I have put in if it is a day of not cardio but a day of like lifting weights on. I tried to you up my protein consumption a bit, but I don't take any supplemental protein or anything like that. 300 milligrams 300 milligrams is wise in seeing here only. Wow, that's pretty. Gets pretty decent. Yeah. Um, so yes, basically, after that, I try to switch the greens mode.

So lunch is gonna be some type of, like, really healthy. Eat the rainbow of colors. Antioxidants, like is much greens like kill spinach, things like that and just really get my daily serving of vegetables around lunchtime.

25:38

The concept of rainbow colors was so, uh, integral to me under understanding my diet or where I was insufficient was just like it's so symbol. What a brilliant like, ah pneumonic device of just thinking through All right, the rainbow of colors.

25:55

Am I eating the rainbow everyday

25:57

might getting purples. Am I getting great? My getting, um, Reds in my getting every every color. I mean, it's It is. It was. So the reason was so hopeful for me. Is it just highlighted so starkly the things that I was missing? Yeah, because it is so easy to like browns and whites. The end. Yeah, you're gonna eat steak, baked potato and or a burger and french fries and quite literally, like half three

26:22

colors on the rainbow. Right? Exactly. So I try to check that box as well.

26:26

Yeah. And then, Okay. And so then from lunch. And then is there a, uh Okay. Keep going. Keep going with the

26:33

daily. Yes. So I you know, in terms of do you want to get exercise as well, Please? All right. So, um, essentially, what I try to do, um, is because cardiovascular disease runs on my father's side. Um, and my dad died of a heart attack. My grandpa died of a heart attack, but it's all on that side. I have to be very careful.

And I want to keep myself in pretty good cardiovascular shape. And so, you know, what I do is I typically, um, well either to a long 60 minute, 13% incline, 1.4 miles per hour Walk. And so I have the pellets on treadmill. I said it the 13% and I'm just drenched by the time I'm done after an hour. And what I do that take my iPad with me and I do a tower defense game because it's 1.4 on the walking suits that you're pretty stable. So you're not, like sprinting or anything. And the time just flies by because I'm trying to, like, beat these.

You know, I'm trying to, like, get three stars and every single tower, every single level, and it just kills the time. And then you're done and and you had kind of fun at the same time, and you're drenched in sweat. And that will be my checkbox for the cardiovascular if it's on a day. And so I tried to that three days a week. And then I also try and dio, um, high intensity interval training. Ah, for another session of the day a week. So I'll just,

like say Okay, I'm gonna go on, do some quick sprints on there and So I use the app called seconds, and I do this thes quick, little you know, 30 seconds prints fall by 30 seconds of rest and repeat that, like, eight times

28:4

and I know a bit about it, but do you mind explaining a little bit of the reason why you're doing sprints? And some of the ah imagines for a lot of the cognitive benefits. But what what else? What kind of has informed that type of training?

28:17

Yeah, I just you know, when looking I'd have to go back and refresh myself on on the different studies that are out there. But, um, you know, over the last five years or so, I would say that the benefits they've shown that you can get the same benefits of kind of like longer duration exercise and maybe even more brain benefits, Um, on the kind of neuro genesis side of things, by doing these really intense short sprints, so it's a fraction of the total time commitment. But you see all the benefits of had you done a 45 minute or 60 minute run, and you can bang this out in 15 minutes and be done with it So it's, you know, I like eating the rainbow where you're doing a little bit of everything and you're trying all the different colors. You get all the different variety of different compounds and antioxidants.

This is that but applied to cardiovascular. So I don't just want to do slow, high incline, you know, walking. I want to do a little bit of like, you know, the other thing I would mentions. I try and get on the pelt on bike and dio you have 30 minutes of moderate kind of exercise. So I'm getting the sprints, the moderate, then the slow, high incline. So I get a little variety of everything

29:25

as and then you add it all together. And if you're doing those kinds of of optimize things, it sounds like it's only maybe 34 hours a week may be fun

29:34

and and then well, then I add in Ah, Sana as well. Ok, I try to do this on at least 5 to 6 days a week.

29:41

Do you mind? Okay. What kind of ah, why the sauna first?

29:45

Well, again, going back to the science. Um, actually, if you go into Rana Patrick's website Ah, um, and type in cold. Our temp Insana. Pdf Rhonda Patrick into Google Something like that. You get linked to her. Pdf where she goes and reviews all the different. And then Rhonda, by the way, she's, ah, PhD scientists that Brilliant has a really popular podcast.

It's amazing, Um, but if you take a look at what she's done and where she's gone and gathered all of the different studies done on the sauna and put them in this one pdf that you can read about why the sauna? I mean quickly, it decreases. Um, cardiovascular incidents. Ah, the cardiovascular disease decreases quite a bit. So does dementia. So does all cause mortality. So it's just like it's a healthy thing across

30:36

the board, and I know I'm not talking to Ragnar right now, but what what do they know? The reasons why they think

30:42

it's something called heat shock proteins that are activated at high temperatures. They think that has something to do with it. The other theory is that it increases blood flow so your heart rate does go up, so it almost is like a cardiovascular type activity, because I can sit in there and just sitting there and get my heart rate up to about 1 20 or so 1 30 So I go in and the data points to 20 to 30 minutes a day. Um, the more days per week, the better. So you want to at least five, maybe six days a week, and then at a temperature of about 100 and 70 plus degrees Fahrenheit. So I do 1 80 20 minutes a day, 5 to 6 days

31:22

a week. And can you do this in any sauna? No. Okay,

31:26

so this is the issue that a lot of So before I actually invested in buying asana from my house, I decided Thio, try and get this done. The gym's you know, like we all have a gym. We have access to our, You know, most major cities do where you can find a sauna, and I would go to the gym that I would bring my own thermometer that I would buy, you know, like a meat thermometer kind

31:48

of thing. I'm sitting and I love your, uh, structure around these things that so Well, well, thought through.

31:54

Okay. I just want to make sure like if I'm gonna be sitting in there and driving, you know, 20 minutes to get to the sauna and like, going and sitting for 20 minutes and you know, there's the time commitment. Let's make sure I'm checking the box. Right? Right. So I go in there and I'm like, Okay, I'm hitting 1 50 Yeah, I'm sweating a little bit, but I'm not getting to where the actual data is pointing to the benefit coming from, so ah, you know, I couldn't I couldn't get there.

And I tried infrared sauna. I couldn't get there, and I just saw. Okay, well, I'm gonna buy a traditional sauna, and they are expensive. But, you know, you're investing in your future, and you put it, you know, you could get pick up one of these units for 1000 bucks or so maybe 1500 you gotta find the right space for it. But you can do it yourself, and you can build a little closet somewhere, something somewhere in your house or in the garage.

And, um, my buddy would just recently bought one for and I think $100 or so and it's an all in one unit in the garage and convince his wife that he was gonna take over part of one of their one car garage spots. And that's where he goes and sits in a sauna, and he loves it. It's a really relaxing thing to Dio, um, and it can actually also decrease your core body temperature because the heat is kind of pulling it out from you once you're done, which will help you sleep better at night. And so that actually doing it before you go to bed is such an amazing

33:13

thing. Yeah, I love taking Ah, hot shower before bed. And I have since I was six or seven and never knew why. And then, um and then through, um, just reading through the research, realizing, Oh, my body really loved when you take the hot shower than the your core temperature gusta external. You start to feel hot, obviously, right, And it's your body releasing its ah excess heat rant and their four year at a cooler body temperature right

33:41

on the bed. And we know now, based on the science again, um, uh, Matt Walker, Berkeley Sleep Lab that a lower core body temperature produces higher quality sleep

33:51

right why we sleep. A great great book. Phenomenal. But I I was just Ah, I was just mentioned a book to friends at that. It ah, whole book on sleep. I remember thinking, um, that came out maybe two years ago or so. And I remember thinking like, do we need a whole book on sleep? And then I read it. I was like, I've won 20 more bright. Exactly. It's the thing we spending 30% of her life,

34:13

Dylan and yeah, I had mad on my podcast and I was just blown away by how much we know now because, you know, a decade ago we knew very little and just like we're starting to really unpack what's going on while we're sleeping and why what it's doing in our brain and how it's helping flush out all these toxins and all these crazy, crazy stuff that's happening. Um, the World Health Organization just classified a lack of sleep as a possible carcinogen, and that's a big deal. So they're saying, like, you know, shift work and things like that is it's possibly killing you, which is just, you know, there used to be this whole thing in Silicon Valley. That was like, You know,

sleep is for the weak. I'll sleep when I'm dead. You know, all these like different sayings. And it just like getting less than eight hours, is decreasing your lifespan and leading to all kinds of crazy things, like cancers and dementia. And it's scary stuff.

35:4

Totally. Um, Kelly star. It was on the podcast, Um, previously, Andy and we and he's mobility expert, just a physical exercise mobility expert. And he was talking about how he got into, um, physical therapy to optimize athletes. And he was an athlete. Huh? Uh, like a championship athlete in his own right, as, ah believe Crew and became a physical therapist,

optimized people. Then his whole career has just he's realized it's just on the basics. It's the foundations that actually produced far greater results by by focusing on them and and, um and kind of using this this analogy of when you're if you're headed to the moon, you could be off by a few inches in the landing would be fine, but if you're off by a few inches in the launch, then you're gonna be off by a 1,000,000 miles. Right and And so he's like, It's so funny that spends 90% of his of his time on Leon. Just how we walk, how we slouch shoes where and you know these air like Olympic athletes. He's helping and you have a money podcast, huh? I need a little you know, you should listen to it and and get him on yours. He's He's phenomenal because he just has gone so hardcore on these foundations and and in the vein of below the line,

it's kind of like, Yes, you can see this above the line version of someone not knowing that they've been so productive because they're thinking through so much of this foundational work, whether it's Olympic athlete or Ah, and working with Kelly Start, or whether it's just thinking through how important sleep is for you, have the longevity of ah, career or am a start up there literally the next three weeks as you're pushing through a really tough time and your and your career how critical that sleep is? I know that when, um, with three hours asleep, the average person will lose. I think it's like 12 points in their I Q. When they take an i Q test again.

37:2

So it will end their natural killer T cells go down and s So if people are listening this and you haven't checked out the work of Matt Walker a great place to start is his Ted talk that he just gave at the not Ted expert, the proper Ted. He was just just give it here a couple months ago and it's out now. So if you ah, type of Mao Walker, Ted talk and the Google, you'll find it. And there you can link it on the show notes and it's ah, it's a great talk. It's a great, like, 20 minute intro to like, kind of get you excited about it. And then you can pick up his book,

37:32

right? Yeah, the, uh, with Kelly. We're talking about this this list of of buckets to check off, and it's ah, and this is kind of informed by, um, his work and and just a lot of my own rumination on this stuff. But it's the five buckets were sleet, and it's kind of his prior to sleep than diet than exercise thin stress management. And then, um and then exogenous compounds and the first thing you know, sleep just most foundation like you can do everything else, right? Get four hours of sleep four nights in a row for a body that needs 78.

Yeah. It's like, what? What is the point of eating right? If you're you're going to, you're not gonna produce great work. Great. Whatever you're doing, right, And and then same thing with diet. You can get great sleep. You can exercise well, but if you're eating like shed as they say him, at least for working out for muscle mass, our muscles are built in the kitchen. It's like what you're eating that actually you could matter much more than just your workout regimen and then exercise then stress,

mate, I think you can meditate an hour every day. But if you're getting four hours of sleep in here, Yeah, I crapped in what is What is the point

38:41

and then half, though? Is it because, like at some point, you also need to be ableto have a little bit of fun? You know, this is where this is where I struggle with because I I like to go and like last night, you know, I'm in town for one night. My buddies like, Let's go get a couple of burgers. It's Bruce and we went down. They had a couple of amazing burgers. I eat all of the bond. I have some fries. Like it was awesome, you know?

So you just kind of have to find that that balance and know when it's okay. Todo also partake in and some of these things. And, you know, I took my wife out on date night and we couldn't get out of the house because the kids until eight and we didn't get home until 11 30. And then all of a sudden, our sleep is all jacked up, but, you know, it's so it's it's you got to be careful because I know some people that are so militant about this. They're actually almost in some ways, like creating more stress

39:29

because they Yeah, let living on a clock. Yeah, You too. Structured, right? Yeah. Everything in moderation, including moderation. That's right, I guess. Yeah, that is a really good, really good point. It's, um Yeah, you can get obsessed with this stuff to ah,

to it. Ah, definitely unhealthy degree. Especially in the exogenous comments, you can just, um, go crazy and supplements.

39:52
What are the craziest compounds that exist for health benefits?

Kevin once tried 5 grams of psilocybin mushrooms with the professional help of a therapist in order to further his understanding of himself and his psyche. It has been described as 5 years of therapy in 5 hours and has helped cancer patients come to terms with their mortality. Kevin describes the experience as incredibly eye-opening and entirely unique, but also acknowledges the insanity of taking “magic mushrooms” as a form of therapy.



I mean, I have tried everything, and it's just like, Why did I do all that?

39:56
What are the craziest compounds that exist for health benefits?

Kevin once tried 5 grams of psilocybin mushrooms with the professional help of a therapist in order to further his understanding of himself and his psyche. It has been described as 5 years of therapy in 5 hours and has helped cancer patients come to terms with their mortality. Kevin describes the experience as incredibly eye-opening and entirely unique, but also acknowledges the insanity of taking “magic mushrooms” as a form of therapy.



It was the craziest thing you tried that you're like, all right, that is not for me. Or I don't think that's for anyone.

40:1

Um, the craziest thing I've tried. Well, the craziest thing I've tried would be doing five grams of psilocybin mushrooms in a guided experience. Where, um,

40:12

I said today, Awesome. I don't know what that's like, but tell me what that's that's

40:16

like, Yes. So, um, you know, you read Michael Palin's book How to change your mind. You'll learn a lot more about this, but there's some really interesting, um, research that's going on right now around the use of psilocybin, um, which is for people who don't know. That's a fancy word for just magic mushrooms and, um, taking the psychedelic, Um, not in terms of I'm with some friends at a park and we're gonna laugh.

Our ass is off, which is what people do on the kind of lower dose side. But in terms of an extremely high dose, like five times the normal dose that you would take, um, and doing it under the guidance of kind of, ah, therapist and putting on a sleep mask and going inward, Um, and really exploring your own psyche and getting to the root of certain issues that you may have, um, and being able to resolve those things in a way that you couldn't do or that would take you. I got because the best description her for this is like it's 10 years of therapy or five years of therapy in about five hours. So, um, you know,

after seeing all the data that was coming out of New York and what they're doing there, um at Thea camera, where they're doing the research out of New York, I'm drawing a blank, but not maps. No. I mean, there's obviously heavily involved in all this as well, but, um, essentially, they're taking cancer patients that are approaching end of life that, as you can imagine, you know, you are going to pass way in a few months. It's really stressful for a lot of people.

Um, just the anxiety. And like, there was reading the story about this individual that, um, he was pre med when he was diagnosed with cancer, he knew he was gonna die. But the curse of being kind of pre med and studying this azi knew exactly where to feel his lymph nodes and look for certain signs of cancer. So he was rubbing like the area's raw in these different sites of his limp notes were checking them so frequently it just imagine, like, internalizing and just like constantly checking and knowing that you're gonna die And, like the how much like cost anxiety in fear that's bundled in that, um, they put him on this program of doing this high dose cell. Simon did it one time and instantly became a piece with end of life, stopped rubbing.

This had a much more positive outlook on life and was just finally able to let go and just, like, release all that tension. Very powerful stuff also, um, with a lot of, ah, military people that are coming in back that have PTSD right and treating them with Phyllis. I've been fascinating results in getting them basic, essentially their lives back on. These people are crippled with these types of fears and anxieties. When you come back from war and begin Thio shed that and release it is a very powerful thing. So I went in, did that? Ah, I addressed a lot of issues I had had with my father,

who passed away at a time where I hadn't had those tough conversations that I want to have about certain issues I had with him, Um, in the way that he was, like, verbally abusive when I was younger. Um, things like that that had just gone on set on said that I was able then to go in an address and figure out and resolve through these five hours. And I came out of in a such a better place. Um, just of this feeling of just release and relief where you're sitting there so deep in your own brain that you're, like sobbing for, like, hours on end while you're doing this experience, the very beautiful and powerful thing. So that was I would say, the craziest

43:50

thing that I've tried not necessarily too much vitamin D. It was exactly here was the host of still

43:59

Simon. Yeah, Yeah. It wasn't overdosing on vitamin

44:1

C or something. Right? Right. That's so the I haven't experienced that, but that and, uh, folks that have listen to the podcast Now that I'm a complete open book on this, the whole point of the low line. And, um, the reason I haven't experienced that was I was actually on my way to what I thought was going to be 4 to 5 gram dose of society and guided journey as well. So not like recreation with friends at a concert. It was It was really checked with the doctor checked with, um my therapist just knew kind of what I was getting into. Probably felt the It's going to sound kind of lame, but kind of the calling to do it for a year, two years and and then got on.

And then, uh, the the Guises to people they're like, um, we're due in Iowa. Oska, uh, tonight and just with the e mails and everything like that, you couldn't mention it, so it was just sound. Meditation was the code word. So I just didn't I thought I was going to take you did. That s o I did it. I was like, Oh, great.

I was like, Holy shit. Okay, we're going. We're freaking and jumping right in and that's like level three stuff. Let's

45:17

do it. Yeah. If so, Simon's level two. That's probably a little late

45:20

or something. Yeah, it was really I was amazing how it happened, because, um, like I I think I was in many ways was kind of working my way up to that and then, uh, and then just got to go right off the deep end because it felt like it was very safe, safe place in again. Like I said, I done a lot of research. This is I probably smoked weed three times in my life before us 30. Like it was not a recreational drugs. I don't really drink. But it was this this, um curiosity and and calling towards towards the therapeutic side of of these compounds and and and all of the research coming out. But so I have not done so,

Simon. But I was It was very similares eight hour kind of attorney that that the only way I could describe it afterwards was, um may be similar to, to your experience of only like I could be. The only way I could describe it was when my wife asked you what was it like I was like, It's it was exactly what I needed. And then there's somebody following questions. Like what? Why? What was? It s So it was so hard for me to go to articulate, because it's not like, Well, that was amazing. Like like a museum park ride, or like,

a movie. Um, it was like it was more like, um, I don't know, eating some tasting something that that Ah, that you couldn't describe the taste being like. Well, for me, that was That was And then also, what was interesting is I didn't have, like, a desire to do it again. Wasn't like, yeah, you know,

the dare program. Kind of, um, routinized thinking of, like, stay away from all of these types of compounds because they can develop habits. It was the exact opposite. I mean, I probably drinking unless afterwards said no desire to to do it again. Yeah. Yeah, its interesting. Have, um have you done mushrooms since then?

47:14

No, that was several years ago, so I haven't I haven't come back. I haven't felt the need to, but, um, I think I would try. I will ask at some point just to check the boxes. I'm curious. I've had so many friends, I have done it now. It had really positive experiences, but yeah. I mean, this stuff is not not even close to being addictive. Anything you come out of there being that so emotionally drained, you're like,

OK, I don't know if I could, like, I don't want to go back in right now like it's Ah, it's pretty intense. It's a lot of emotions packed into one small set of ours,

47:44

so right, Yeah, it's the It's the opposite of escape. Like you're No, you don't. It's ah, confrontation with with right, Yeah. You needed

47:53

to confront alcohol escape like, Ah, she's relaxed. Now. You know, that's very much like I'm escaping something. This is addressing. Something is bothering you right in your face, you know,

48:4

But it Z, that sounds scary, But But, uh, I think it's, um and not everyone should do. It is you really should with Dr Take it very seriously. Um, I think it's it can be really dangerous for people to go around just saying, you know, everybody should do it, but ah, but there is There is really it's a safe way to confront something that is impacting your thinking is for me is impacting my subconscious or my conscious thinking every hour, every day. And it was like, Okay, they're confront this head on in eight hours,

and it wasn't too scary. But have you read Michael Palin's book? I haven't, But you have it, and I have occurred. Um, I have probably still have started the audiobook once or twice, and I've heard I listened Every podcast that this kind of like a pack around reading book. Um, whenever you write a book and put it out there if you were in the book, All right. Well, whatever you d'oh do podcast episodes on it selectively, because by the time I added up the 12 hours, I'd listen toe 56 different podcast. Yeah, I've got grass. A lot of the book, But what What comes to mind when you just

49:15

that I think that the one thing that that Michael um was able to achieve is that he is one a very credible, um, kind of person in this space, like, just bring in a great writer, right? And so, you know, he came into this and said, I've never. I'm in my fifties Have never done any psychedelic. What is this all about? What's this movement about? Um what are we actually, you know, people. They're starting to move out of the arena of recreation and more into,

like, getting serious about this where they achieving. And then how did these different compounds work? What's their history as well? So getting it in the history of the different compounds and so you know, and he goes in and tries everything. Okay, I'm gonna try book. I'm gonna try acid once. I'm gonna try psilocybin ones. I'm gonna try five m e o d m t one. Somebody try all these things. Fogel goes and checks all the different boxes and reports back on on what happened. Um and so I think it's just like if you're just curious about seeing this stuff so much in the press these days, because it's popping up everywhere, and you want someone that,

you know, is not a it's not a hippie is not a druggie is not like this. Someone's gonna come in and report on this. Um, you'll learn a lot even if you're never planned on taking this stuff you'll just learn it. Learning

50:29

time, right? Yeah, the I've, um I I grew up with a lot of mental illness in my family. And I was one of five kids, and and, um, and have ah, brother, that sze bipolar. And and, um, my dad has never his 72 year old Ah, Texan just kind of straight edged, um, type of type of guy.

Um, very conservative. Very like my entire family's all religious conservatives. Yeah, and yet he read the Michael Pollan bow. Wow, that's my brother. Gave it to my brothers. Who's about to give it to your brothers? Yes. He like 70 todo about

51:15

trying this stuff. Yeah. You take him

51:18

to the little I Alaska. Jenny? Yeah, Maybe it's that it's its own, you know, Takes like five years to like, I guess ferment in the brain is open to it. But yeah, maybe it's 77. That's what I will do. I gifted the book

51:31

to my sister, who's very kind of conservative person, and, you know, it's I I really was hoping she could absorb some of this, and she's sense kind of opened up to some of these ideas. It's kind of

51:44

cool. Yeah, it in his book is, I think, one of the seminal moments of it becoming serious cause yeah, um, again, the book is how to change your mind and write how to change mine. Yeah, he, um you know, he's been a best seller a 1,000,000,000 times over, right on everything else regarding food. And then he approaches something else that we can ingest and, um, and comes out on the other side with, Like,

Is that really level? Take, um, it's and the dialogue is moving pretty. It's swiftly away from like recreation, too. Hey, we're We're willing to give people lithium. We're willing Thio too shock their brains. Ah, why not be open? Thio? Um, this little fungus that grows on trees the end And it's

52:32

especially if you can actually truly quantify the results and say this is changing people's lives, like if you have someone that has gone off to war and is just a crippled person when they come back mentally and this is proven to work like I just don't get how you can't say, Let's

52:48

let's try this right, right. It's ah, it's It's great to see the momentum moving in that direction. Um, okay, going thio off of the things that view, uh, in gesture, do each day or not, just in the fast fasting side of things. Um, for listeners, Kevin has been a mainstay in Silicon Valley for for ah, here in 2020 years. And, um,

and actually started one of the first podcast back in 28 2004. Yeah, right. One is getting going and has an amazing podcast right now. Your own podcast and great newsletter. Um, amazing stuff, um, and really love that. It's ah, just feels very in a world where everything is, like, automated, very curated, very just thoughtfully chosen. Um, and it's not inundating. Uh,

53:37

yeah, I tried to do well, I haven't done any couple months, but that's the whole point Is like on Lee do a newsletter when there's something that's really compelling to share with people vs, Like, you know, I've signed up for some newsletters where they come every single week, and ah, yeah, I think that's, um, it's worked out quite well, like people. Open it up. It's It's got a really high open rate. Um, because of the fact that I only do one every, you know, month

54:0

and 1/2 2 months? Kind of. It's really great. Podcast is also great. I think the first episode is with Rhonda. Yeah, great episode. Um, the, um What has been from that 2000 getting hair? Um, too. Now, I know you live in Portland. We'll talk about what you're doing right now. Um, what were some of the moments that below the line moments in Silicon Valley that really kind of shaped who you've who you've become as,

ah, as a founder, investor creator. When you think back to, like, the years moments that really shaped and defined the below the line kind of definition to ur which ones come

54:39
What are some moments that have shaped who you are today?

Understanding that asking for help is ok and being selfless were essential for Kevin’s success, especially because he never finished his degree and often found himself surrounded by graduates of prestigious universities. During a conversation with Mark Zuckerberg, Mark described how he had surrounded himself with a slew of mentors that worked alongside him to make decisions for the company. Kevin believes that not being the smartest person in the room and putting one’s ego aside can benefit them in the long run.



to mind. Yeah. I mean, I think that, um, a couple things come to mind it certainly just understanding that in admitting to myself that I needed to I didn't know everything, and it was okay to ask for help. I think was the biggest change that I made over the last, you know, 10 plus years. Um, what's an example 10 years ago where you wouldn't I think that you know, you're when I first moved to the valley, I dropped out of college. I was studying computer science, and I thought, Wow,

it's 2000. There's a lot going on in the Bay area. I need to get out there because of the first Web. One point. Oh, like boom was going on, you know, everybody was going public. And where were you where I was under Ross Vegas of the ball places, You know, V. So, um, I was there because my dad was an accountant and he got a good job offer to go out there. And so I moved there when I was in second grade. Um,

so I grew up there, and then I just you know, I was reading all these tech magazines and I was very much a geek all throughout my adolescence, and I just decided, OK, I need to get to the area. So I found a job moved out here. Um, but I was really ashamed that I didn't finish my degree. I think that I was really for a long time, I felt as though, you know, everyone was like, Oh, I went to Berkeley. I went to Stanford,

and you're just sitting there surrounded by these people and you could see the holes that you had by not finishing like little certain pieces were missing that I hadn't kind of fully fleshed out at that point. Something like what it would be just, you know, you sit down with someone that has their MBA and or in their understanding of of, um, it's 1000 things like as a founder that's getting started. Um, you know, and starting my first startup, which I launched in 2004 Um, I didn't know what a cap table was. I didn't know what vesting vesting schedule was. I didn't know what a cliff meant. I didn't know there's 1000 things that I didn't know. Um, that had I,

you know, taken some business classes in school. I probably would have had at least ah, simple grasp of what was going on there. And I missed all those things. And so, um, I was a little guarded, I think, in my early twenties, and so I was like, Well, I can't let people know that I don't know this And so I was afraid I was. I was afraid to surround myself with with mentors, which is what I should have been doing. Um,

and in doing so, I kind of handed off responsibilities or didn't want to engage in certain things that I wasn't proficient in. And so when it came down, Thio, how do you properly interview someone? How do you vet someone for your business? When I had to start, that was starting to grow. I just let other people do that. I'm like, Well, you've hired people before you go do those interview in Which company was this? This was dig when I started in 2004. So dig was the kind of first social news website. Um, so I launched that,

and I was very much the product person. It's well, I'm gonna be the product person like that's what I That's what I know. I know how to build a product. I I know what features and functionality of this should have. Um and so I focused on that, and so it was more of a design role. But I handed over the keys to the castle in terms of running the business to a different CEO, Um, in terms of hiring employees. And there's 1000 things that I just like just handed off to

58:12

other people. And was it out of kind of fear or or

58:15

justice out of fear of admitting that I didn't know how to do something and not asking for help? And so, um, I would just dodge those things. And the problem was that, um I think I would have been pretty good at those things in terms of making certain decisions that I would then later look back and be like, Oh, we did this that way, I wouldn't have done that. That doesn't make sense to me, But I had no input at the time, so I can't go back and like, you did this wrong, cause I really wasn't involved in the discussion at all. I was the one that removed myself from that discussion. They didn't remove me. I did it myself.

And so I felt as though, um you know, I I just really look back on that and realized a little bit later in my career that I should have been involved, um, and asked for help. And I was something I learned actually from Mark Zuckerberg, of all people. Um, he was ah, you know, younger than than I AM and dig had taken off and become a bigger website than Facebook in the early days. Um and so he came to my office and he sat down, and we just talked about kind of what I was trying to build. And, um, we're chatting about face because it was just kind of getting off the ground.

It has some great initial traction. Um, and I just asked him about how he was handling certain issues and regards toe firing. People are finding key talent. Um, you know, we were having a hard time finding engineers that could help us kill our platform. And he was doing a pretty good job at that. And he just described to me, um, how involved he was and how he had surrounded himself with a bunch of coaches in these areas that he didn't really understand. And I was like, Wow, I Why did I eat? What was the my rationale there. Why was I dodging all of this stuff?

60:4

Yeah, I I I got here eight years later, but I remember hearing the stories of of, um, in the early days, how great Mark was in asking questions like crazy. We would hear an acronym and be like, What does that mean, Right? Well, you would hear a term in and said, What is that? And at 19 had no problems. It's so obvious looking back. But like at 19 having no problems just being ignorant and trying Thio solve for that by just being like, What is that?

60:35

Tell me what they're having to be the smartest person in the room right now, and I think that that's a big thing that comes down to ego. And so I had an ego that was like telling me he won. You shouldn't. Well, it was really just I was I was ashamed and I didn't want to expose that part of me and looks looks foolish for those 30 seconds. And I feel like that was, ah, big mistake that I later correct it. But, um, you know, I would say that was one of the big learnings there in the very early two thousands.

61:5

Do you think part of part of that could have been obviously an internal on personal Part of it was dig took off so fast that maybe it felt like regressive to be a year end of this thing that everybody is saying. Holy shit. This is the thing that really that you felt like Okay, I can't go back And 100% these guys did it. Seemingly beginner questions.

61:26

Dig exploded so fast. You know, they were putting me on the cover of magazines after, like, six months. And

61:32

I'm like, I remember and I remember I remember seeing that saying the cover of this is we could be like That's what I want to dio like it's I appreciate so seriously. I really did. You know, that guy they have a picture

61:45

taken of him was like, Oh, shit, What the fuck

61:47

am I doing? Like, I don't know what I'm doing. That's that is I feel like that's now no seeing behind the veil, Uh, for a handful of years, that's everybody on the cover of a magazine. But, man, I remember seeing that, um and I was in college and, um, and being like, wait because the remember the exact language on the magazine, but it was basically like, ah, 50 million and six months or something like that,

and it was just like, this meteoric rise. And there was the ego and me thinking, Ah, wow. Someone on the cover of magazine You must have it all figured out and buy. That's a shortcut to impact. But also short cut to financial gain is that's the quickest way I'm over confident I could do that too. But I remember that that article on being really inspired by that, um and but but keep going, Yeah, it's hard to be on the cover of a magazine than a week later. Be like, Hey, can you explain this this cap a cap table too,

62:48

right? Exactly. Exactly. So a lot of like hiding and ducking questions and things like that.

62:54

And what was what was, um, fast forming to Thio a few years later? How do you even now, how do you look back and think about digging my own story with with tilting building something that also was this high flying company, didn't achieve his dreams and just felt like I was crumbling right before me in the last six months after you know, $400 million valuation massive on we met during the journey of, uh, felt very briefly. Um, it's I I call it kind of this beautiful mess, and we really appreciate everything about it and but also learned so much from it. But how do you in 2019? But I remember thinking, Okay, Kevin, this guy that I that I really admire from afar,

he went through something like this. And this come out stronger, better and just great on the other side. To every is, this is actually pretty crazy to have you on the podcast, because I really did think. Okay, that's someone that night. Because we care about are at least I care about these narratives of like, Okay, people have done this before. Um, but I'm so interested. Well, how do you think? 2019 Look back and think about those those years with

64:11
How do you feel looking back at your younger years?

When he looks back, Kevin finds himself blaming other people for his failure when everything crumbles from underneath him. However, Kevin is grateful in part for his failure because it allowed him to mature as a person and eventually grow into the composed man that he is today.



Dick. Yeah. I mean, I think that when I think about where I was mentally, emotionally like maturity wise, I was kind of doing the best that I could with what I had at that time. So I can't really look back on that and be like, Well, you know, I think initially when everything crumbled, I initially back and was like, pissed, You know, I was just like I was blaming other people. I was just I I just felt, is though, um,

I could have done something different, I and but at the same time, it's it's kind of what I needed to mature. It is that experience and that failure that that helped me just realize all these things and find all these holes and gaps and go back and plug them. So I I'm grateful for the experience, actually, and like I look at all the stuff that we built, I'm very proud that when I see some of the features and functionality that we built back in 2004 are still being used in modern applications today. Like that's that's really cool like that That makes me happy. Like I had a very small impact on on something that they pushed the Web further. Right? So that's that. That I can rejoice and, um and I don't know, I I I think that, um,

65:31
How devastated were you about Dig’s failure?

Kevin never had a serious breakdown over how Dig failed, mostly because Reddit, Dig’s greatest competitor, didn’t beat Dig at its own game. Dig managed to hold its own as a democratic algorithm-based content website, but Reddit overtook it by focusing on smaller communities run by individual moderators.



Did you ever shed tears about it? Did you ever have kind of like

65:35

I didn't really have a breakdown about it? I think part of that was our biggest competition at the time was read it and we where we beat them well, we beat them for many years, like we were much bigger site than read it. They sold the Conde Nast Ah, and then later brought it back out of Conde Nast and kind of spun it back up again. Um, where read it. I would have been. I think I've been It would have been pretty upset because ready came out and they were more or less, um, a clone of what we had already built, like features and functionally, we're pretty much the same as what? What they could build. Um, so if we had lost that battle,

I think I would have been pretty upset. What read it did that was very innovative. As they said, We're not just about the front page. We're about this long tail of smaller communities that are run by individual moderators. Of those communities, we had a different take. We want to be driven by an algorithm that would automatically promote the best content to the user's not have there be moderators in place. So we wanted a little bit more of ah, Democratic based system versus the power being in any one individual's hands. Um, they went out and said, we're gonna be about these sub read, It's and that's gonna be what makes us different. That was a brilliant call there was. That was the first time read.

It really made a pretty big innovation and did something different than digs up until that point, it was just copying what we had already built. Um, I applaud them for that, and I think that they deserve where they are. I mean, they're massive site today, and that's awesome. So, um, I'm not upset because they made a ah, I would have been upset. Have we just been cloned and defeated? But I think that they did some solid work there, and that's why they're number one today.

67:17

Do you remember a for founder's out there going through, um, just the founder journey. It's the whole, the whole thing. Do you remember? Ah, moments like a friend said recently. You know, when you talk about the hard times of of entrepreneurship, can you ask guests specifics like specific moments? Do you remember specific moments in when you felt like it was getting away from me when he felt like, um okay, this this thing, it's, uh, everyone's journey so different, But did you ever feel like Oh, okay. This is it's It's a failure

67:50
How can I recognize a failing business?

During a Dig board meeting that occurred after the company raised 35 million dollars in venture capital, one of the company’s members brought up the idea of having more mainstream news on the front page to promote general publicity on the site. Kevin’s had a negative gut reaction to the idea because he loved the unique news that made Dig unique, but the idea went through anyway. A combination of other issues like tech issues, the war with Reddit, and a change in media direction all took a toll on Dig.



now. Yeah. I mean,

67:51

I go from there is a chance to This is a feeling. Now, I think

67:59

that when I knew things were going sideways, the specific moment was that there was this idea. I had lost control of a few different aspects of the business. One was being that there we had raised a bunch of venture capital we'd raised, like, $35 million or something like that. Um, we

68:23

which had the time, was astronomical right now, saying your seed round. But but back then, yeah, that was It really was like, Okay, all eyes on you came out of it so fast. People loved it so quickly. Today,

68:36

in today's dollars, that would be the equivalent of probably 101 $150 million. It was like a pretty big deal back then. So we had gone out and raised a bunch of money, and it was clear that we need to start making revenue. And we had our own ad product, which was, um, like, datable ads, which ah, you can see a Red House today is basically what the impact that we created initially. And, um, I thought that was pretty innovative at the time. Was no one had this idea of being outside. I like or don't like an ad and help that kind of propagate the ad.

Or we have this idea that, um ah, if an ad was underperforming or voted down enough, it would just disappear from the platform that that advertiser wouldn't be allowed to actually even buy ads anymore, which I wish we would have pushed that all the way through. But, um, the issue was that Okay, this weird, wacky news site, that is dig is not mainstream enough. And at the board level, there was brought up this idea of We need to make this more friendly, too, every type of user, and so it needs to be more mainstream news.

So we need to get traditional publishers involved, get more traditional content in there, and that kind of went against my gut. My gut was telling me, Well, what makes dig a special places all the wacky, crazy stuff that you can't find anywhere else If people don't want CNN stories in the front of dig because they could just go to CNN rights. That's what they want is the weird, odd, wacky stuff. And so the decision was made to focus more on the publisher side in getting more of their continent there in changing the tone of dig, which was really damaging to what we did. And I just knew that was the bad call in at the same time, Um, a bunch of other stuff is going on in terms of scalability and, um not being able to scale the website in a way because things were falling over and the features and that we wanted to build going forward,

we could not build because our database will just crumbling. Um, and so there were a lot of things that all came together where I looked at everything and thought, Wow, this is going one is going in the wrong direction to Technically, we're having issues. Um, three were fighting this battle with Reddit on this front, and they're going in an interesting kind of new direction. With subreddit, it's, um this is this is going sideways, and I'm losing some of these product discussion battles because where the focus is more on revenue than what's right for the user. And that's when I I think it went sideways.

71:16

And how many years in was

71:18

this? Ah, like five years and something like that.

71:21

And so and then, um, if you've done so many things in the last 20 years or there are other stories that you'd also say or kind of like And I needed that in that maturation process as an entrepreneur, za as a person as a leader, Were there others, um, that come to mind in the last?

71:42

Yeah, I think my first day Google. So I added a small little incubator that was building, um, some products. We didn't really find anything that we want to double down on in. At the same time Google came knocking and they had tried to acquire Dig way back in the day. Um, and they wanted to bring our team on, hire us and and, um, have a built in progress over Google. And so I was like, Okay, well, I kind of always wanted to do that Google deal way back that that fell through as I could. I would be really cool to be on the inside of Google and see how things operated this level.

And when I landed inside of Google, I just was blown away. I was blown away by the quality of talent that they had and how the extreme vetting that they went through to hire people and to make sure they're like three years, three years, which is really rare

72:36

for an entrepreneur through acquisition to be there. Yo, nine months, 12 months, 18 months, much less three years in a company that probably had at that point 50,000 employees. 50

72:47

1000. That's right. And I know how you knew that Amazing

72:49

does a total guess, but ah, yeah, the ah, I mean, it's a massive, massive company. When we got acquired, it Airbnb is 2500 and within two years is 5000. And the number was one thing. But just the fact that more people in the company were there in the last few months, then you know, Ah, then the last five years or something was just so, so crazy to me. But you have 50,000

73:12

can imagine. Yeah, it was it was nuts. Um, but I think that what I was most shocked by was just, um when you sat down at the table and you were discussing scalability issues. And you're discussing product issues? Um, just the attention to detail and just the kind of discipline around decisions and the thoughtfulness and the work ethic that went into all these things was just a whole other level. And I was like, Wow, this is what, um, it looks like when you really take your time and find absolute the absolute best talent in the industry. Um, not to say we didn't have a bunch of amazing people a dig, but I think there's certain key hires that I would have done a little bit differently.

Um, because we did have some wonderful people there, but it's just a different. It's just a different level We didn't spend near the amount of time, um, that Google does and put enough emphasis on just really trying to find, um, that level of talent.

74:21

Interesting, OK, And so within day one And what was what was day one month, one month, the 1st 3 months? What were they like as you integrated within?

74:30

This is really tough. I mean, it was it was an hour commute each way every day. And, um, I was put on the Google Plus team and Google Plus was, Ah, couple 100 people at the time and I was in charge of the mobile app. So basically the product person that just ran mobile, um, and the issue I had was that the what we wanted, what I wanted build is I thought that Google had an opportunity to come in here and do something drastically different then what Facebook was doing. Um, because why not ends up? But the push from management above me was, Let's not do anything crazy. Let's rather let's just do were Google so we can do what Facebook can do but better. Which means copping Facebook initially and kind of just doing feature parity with Facebook,

75:28

which isn't isn't bad a bad idea? I mean, Instagram has shown how valuable it is to copy Snapchat and and let them innovate, come up with it, but then implemented instruments and it's worked.

75:40

Uh, yeah, I mean, there's there's bits and pieces there that I could say, Yeah, I would agree with that on the and I think we're Google made the right decision, but it was until much later was that Let's double down on these individual, um, verticals and say we're gonna be the best in photos. So let's make Google photos that best in photos. What they wanted to do is really create this one beast whale of the were all things to everyone, which I think is really difficult. It's just bloated, you know, Right? And it was like the circles I was fighting so hard to kill circles circles was this idea that you would go in and categorize every single person you inter interact with into a business circle, friend,

circle, neighbor circle or whatever. And I'm just like j to an engineer. This is this is where this is where you get in difference between Apple and Google, which I think is fascinating, um, Google over indexes on engineering talent. They they don't bring in or appreciate creatives as much as, say, someone like an apple. And so what you get is thes, um, applications that can scale to billions of years with ease, but very sophisticated. Let's throw all the features and functionality in here because we're engineers and we like to see all the options versus how can we Yes, we can do 50 things,

but What are the 2 to 3? Things are 3 to 5 things that really matter that we should be doing versus trying to throw everything and be everything to everyone. So Ah, that was the issue with circles. It was just like I'm like, no one is going to spend an hour two hours of their life categorizing everyone and discreetly sharing to his individual silos of people. Then you can't remember. Oh, is, you know, James and this group or that group on what it's like It's right. Yeah. And you're How long were you on the Google? Plus, in just a few months, I I immediately started looking,

um, internally, it was their other areas that I could jump into because I would love to have worked on Gmail or Chrome or any of these other kind of really fun, um, departments, because obviously Google has so many different, really interesting areas. And, um, I was chatting with, uh I was connected. The Christians who? We just saw her earlier. He was with me because he joined Google because he's on my team. So we joined at the same time. And he's like handing people over Google Ventures and I had already been an angel investor in a bunch of startups.

And so he was like, Do you wantto have a conversation with them? And then I met Bill. Marisa ran Google Ventures and left shortly after I did, um, and was like, dude, that come join us, like make the jump. And that was a no brainer.

78:22
How was your time at Google Ventures?

Kevin adored his time there because the organization was well-run and he got to angel invest in a variety of different startups. Although he wanted to spend more time there, Kevin yearned to build products of his own again after a few years in the program.



Where they It sounded like a really cool group within a lot more free rein.

78:27
How was your time at Google Ventures?

Kevin adored his time there because the organization was well-run and he got to angel invest in a variety of different startups. Although he wanted to spend more time there, Kevin yearned to build products of his own again after a few years in the program.



Obviously, I love my time ago, Ventress. I had a blast. I That was just such a well run organization in such amazing people. Um, I would have stayed there a lot longer had I not wanted to, like, start building products again and started dabbling again. Um, I probably still be there today. I just kind of felt the itch after three years to want to go off and do something else, and so did a lot of other people. I think there's probably been, Ah, I don't know. Maybe it six or seven people have left since I left.

My boss, Bill, who I absolutely loved, left a few months later. So we're all kind of talking about this, um, you know, do you want to go do something else you want to build again? Um, so, yeah, few of us peeled off, but my time there was Was there a great group of folks? Yeah,

79:14

that is. That's also minutes. It's rare yet have a founder that stays there three years, So it must have been great. Um, does what's 1/3 formative experience that that you reflect on often, but people wouldn't see in a, you know, in a bio, on on you. But you actually think quite a bit about, um, in your time of building, unless 20

79:35
What’s a specific experience that molded you but wouldn’t show up in your bio?

After Dig, Kevin overcorrected his past mistakes and tried to dominate every aspect of his next venture. It wasn’t until Google that Kevin understood the value of a well-recruited employee. Kevin also realized the positive aspect of failure and how failure is one of the best ways to move forward.



years. Yeah, I would say, um well, I think the last thing is that I was always so I became a little bit at post dig. I thought, Well, if I can't control the people, I'm not getting good output. I should do everything. I should just be in charge of all these different things over rotated. I only overcorrect I over corrected the other way. And so I essentially said Okay, well, my next start up. I'm just gonna take on everything and I'll wear all these hats and that'll be fine. And,

you know, it wasn't until I realized, um kind of a Google that if you hire the right folks and you can trust them, then, um, you can hand them the keys to the castle and let them go run with it. Um, so that was that was a big piece. But the other thing along the way was, um but there's so many different lessons that came up in terms of entrepreneurship. I think one of the things that I always talk about with other founders is flipping this idea in your head that failure is a bad thing and is understanding that a failure is just admitting that you've learned something is like it's such a refreshing way to look at it and you realize that the only way we move forward is by failing. And that's actually the best possible lesson like you. If you just have success all the time, you're just gonna think that you you know, it's gonna cause you to go on and create things that, um,

I feel well, I guess I was in this boat a bit when I started digging the revision three and I was like, I got too hot products like I'm just gonna go. I can go and build 1/3 eye. One created pounds and then that failed. And I'm like, Well, I I've still got that hot hand. I'm gonna go created another and, ah, there's nothing wrong. I've always kind of like I mentioned earlier. I've always kind of been this person has just a bunch of different crazy ideas. Um, but I think a lot of new entrepreneurs get really beat up and paralyzed when something doesn't work out, and they take it. So, like the the internalize that I think it's a really damaging thing.

81:49

Yeah, I wonder why that is. That's a really good point. That or an interesting perspective if you feel like it's it's ah, newer thing for people to because the Valley is known, is the place that really was receptive Thio

82:0

failure, And I wonder if that's changing. Here's the problem. Did nobody has really talk like real conversations about this? Nobody says I'll give you a great example. Um, I don't know if I don't I don't want to call people out here because I don't use names. But like there was ah, social app that raised a bunch of cash and was then later sold off for pennies on the dollar. So an but the press release that came out it was a company raised 30 40 million box press release came out. Was acquisition of this company has happened by this company, and I'm looking down the Twitter stream to the founder that had just sold the started for pays on Dog Didn't make a dime. Horrible day product failed, but they were acquiring the team. Congratulations. You're joining so and so that's gonna be so amazing. Bravo.

Great job. And it's like stop, You're all just lying. That was not a successful outcome. That person failed and it's okay

83:0

to save hat and it's a missed opportunity for them to learn. It's the ah, I love this because I look back on, we had a really harsh press, Really. It was not like this. Ah, this thing swept under the rug like we had the block post like, hey, we're joining forces their well being in the email thio two customers because so that that kind of made it seem like Hey, this is a continuation. But man, was it not? And Brian is great. Ah, press that was really like probably too harsh, Like,

even like going into talking about my wife or no reason. Um, was really strange. But I look back and I loved that on Lee with distance only with perspective, because he didn't allow me to think, Hey, that was, you know, that was a success, right? And people still, I think they'll see, like if they're there, If they don't necessarily know startups, we'll just see Ah, and I have the above the line version and in,

like, yo, uh, linked in, like, sold the company to everybody, but not but the bolo line version whole point of the podcast is And the conversations that are riel um and I love that there was this public press because then it wasn't like something that could be brushed under the rug. It was like, James, you needed, like, face. This really internalize it. Um but it also

84:23

gives you an opportunity to inspire other people, right? Because that your failure in coming out and saying this didn't work out, um gives you Well, it just It just lets people know that it's okay. You know those people permission, permission to also fail along. It's their feelings Why bottle of this stuff up? You're gonna be going to spend so much money on therapy over the next 10 years. Like why? I just talked about totally, Totally. It's a ah, great way of our ticket you

84:48

will deal with. It's kind of like over China. A few minutes ago. You will confront it. And it it could be in the background of every hour every afternoon or these mega decisions that you're making and not knowing why you're, you know, reverting to something about you could hit it head on.

85:4

Does it feel good to you now to chat about like, for my people will come to me to say Kevin like, Oh, hey, nice to meet you, man. Like I loved dig back in the day like Sorry it didn't work out. I'm like, Dude, it completely feel I messed that one up, but blah blah. I was a fun time, you know, And we which had about it, and I just like it's almost like my own therapy. I could be I could be fine. I I fucked everything out. Dude, I love it so

85:26

much. And what's so, um, just, ah crazy And like divine about this conversation right now is this is the most enthusiasm that I'm able to talk about. Like, say, I love that this article happening, and I don't think people would understand. And I know a close friend that that just sold his company, and it was a, um it was one of those Congrats. Everything looks great, then make any money. Didn't was just went through amazing experience, but is now going to be is go on, Lee going to go down this path dependence of conversations of like it succeeded.

Ono is great. And we were about I sold a business when I was, you know, before I was 30 and and it it's almost like, Oh, no, this fork is happening in road work. He's going to be relegated to that version versus this really version of where I mean, it has made me a decent, maybe good angel investor, because I'm able to tell them. Look, I've seen everything from layoffs to insanely painful acquire Thio the amazing highs of raising a ABC and everything in between. Yeah, and and they're like, that is the type of investors want,

rather than if you have an Angel investor and I had these that ah ran a $1,000,000,000 company and only talked about how they're succeeding along the way. Are you know how lucky they were That it was actually maybe was the real version. They had been swept up in a wave. They weren't the people that I could go to and say Holy shit sounds. I think we need to lay off 30 people off our family friends that we love. How do I navigate this? Couldn't go to them. And it's so liberation comes in many forms. Honesty is one friggin hell away to have that liberation, and and it is so liberating. Um, and in a very weird it's just

87:22

a release. You know, it's like this release of not having Thio feel like you're covering something up. Like, deep down, we all know like what happened, you know, you know what happens, and it's like I can either put on some kind of, like, facade, some fake face that is kind of like sweeping things left or right or a little under the rock. A little over here, you know, trying to like, pretend like something went away that it actually didn't or I can just, like, be straight up with people and feel good when I go to bed at night. You know? And I think I would rather take that that mode any day

87:53

now. And I, uh I can ah, I would guess you are in a great place in life. I mean, I feel great, like, it's it is, and I and maybe it's and I see the projects that you've taken on have been so intentional. Eso deliberate. Um, even just we're gonna have to do a part, too, in this podcast, because even just I would love to know the inner decision tree off, starting something and then, um,

handing it off. And even with this maturation of of okay, I handed too much off then I didn't too much. And then, um, starting Ah, something that that Then you hand off voluntarily Thio two maser, and and and it, I imagine, was probably a pretty, um, pretty peaceful thing. Um, but the ah, but yet it's the reason this is so divinely. Quinceanera was because I saw your progression as an entrepreneur,

and some of that was ah, a few years younger, saying Okay, this. This can be the beginning of great things. Even if it feels like when people are writing me text like, Hey, don't believe the press. This is I know this awful and imagine to them my wife remembers like the day that article came out Within two hours, I was like, really harsh article came out within two hours. I was like, Cool. There's no like integrity issues. There's no like, I think I would actually like working with a person that has been through all of this,

but too many friends there were, I think to them it's like, This is the word is like a stamp of disapproval. This is This must be so hard, right? But when you are like the ah creative person you like Okay, this is gonna help me create. I don't need to put my future in someone else's hands if I'm creating things, this will help me. And in this concept, I only heard about maybe a year or two ago is post traumatic growth that it was even and dealing with the death early on in life were different things. That it was like Okay, but I've seen this pattern before. You can grow in immense ways through these experiences. So cool, because to have this conversation with you,

this enthusiastic conversation that I'm sure listeners are like, What the hell are they talking about? Because I remember seeing man Kevin is like cruising. Um, and probably took so much from that experience and had that Ah, growth come from it. Well, real quick. What has been, um, so then I imagine, like, a bolo line question. Imagine you've done very well as an investor. Probably informed and invaluable. E due to dig and through Ramiro and milk and and pounce and the failures and successes. Um, is that is that an accurate characterization?

90:45
Is it accurate to say that failure in a great informer for entrepreneurs?

In terms of his professional career, Kevin’s investments have been his most successful ventures. By trusting his gut and his connections, Kevin has managed to invest in companies as successful as Facebook and Twitter.



Yeah. I mean, but certainly my investments have been the most successful, Um, piece of of what I've done professionally, um, and that I've been able to, um, work with some great folks. I think I was really lucky. Ah, in around 2000 for to be in touch with all these other entrepreneurs, they were building great start ups the time. And so, you know, I I at that time was like, Hey,

can I invest in your company's which, you know, led me to doing Twitter and Facebook and Square and a bunch of other, um, awesome race. It's a great rap sheet. Yeah, it's been It's I I got, you know, it's it's it's it's a lot of luck and in a little bit of, um, I'm a product person. I can look a product, I hope I can tell that. Oh, wow,

They're figuring something out that has, you know, there's a lot of blue ocean out there. This could be a pretty massive project, pretty big space with the right type of founders behind it. Um, so just knowing that is ah in trusting my gut along with being connected with these great folks has led me to do some pretty awesome deals.

91:54
Would you say that being an entrepreneur in necessary for a good investor?

It certainly has helped Kevin. Having conversations with people that have gone through similar situations is always easier than talking with someone who has little experience. Kevin prefers being the investor that sits on the sidelines most of the time



Would would you say that? Or do you feel like the entrepreneurial parallel paths have been necessary for you to be in that position?

92:4

Um, they certainly have helped. You know, I think that when I've had certain discussions with entrepreneurs about a lot of the things that you had mentioned a few minutes ago around layoffs and things like that that I know when you haven't been through that, it's ah, it's very nice to have a conversation with somebody that you know, um has approached this and you can share what kind of worked? What didn't work, Things like that. Um, I also love kind of product brainstorming. So when I work with a lot of these founders, it's, um, you know, sitting down and working on the product and actually getting early releases of the software before it's fully baked and, you know,

throwing out my 10 or 15 different ideas. And maybe if one of them's good, when will get implemented into the product and make it back out to the world, which I actually get a lot of enjoyment out of. Um, so little things like that, I think is it's been a lot of fun for me on the investing side. Um, just having, you know, the I. I like to be that investor. That is just kind of like they're on the sidelines waiting for the I don't wanna be the overbearing kind of like in your face. Always investor. Um, I I waited till they reach out to me and asked me like a Do you know someone here? Can you help me out with this one particular product decision? or whatever. Maybe. And that's how I like to interact.

93:23

What is the what are the things on your plate right now that you're most excited about? Um, within the Portland realm and and in part two, we'll talk about the move to Portland And why you decided after so many years in Silicon Valley. Okay, I'm heading up north, but, um, what other things on your plate right now that are most exciting?

93:43

Yeah. I think that, um it's been a crazy It's been a crazy year so far. Um, a bunch of companies that I invest in back in the day are finally starting to go public. So slack is going public today, which is a big one. Um ah. Uber was the one of the big investments who did. Why was the Google Ventures and so seeing that actually get out after all these years is a has been nice. That's finally publicly traded. I'm rooting for them. Um, they've got a great CEO in place now, so I'm really excited to see what What he builds over the next couple years. Um, in terms of things that I'm excited about,

you know, I love the health and fitness realm. Um, you know, I'm on the board of Aura, which is, Ah, ring company that allows you to track your sleep in the tracks, all the different stages of sleep. I've been kind of helping out there on the product side as well, so I'm excited to help them kind of push that app forward. Um, there's a lot of work to be done there. Um and then I just invested in Chemical Jor Joo. You are, which is a guided journaling.

And so it's all encrypted, and it gives you daily prompts to kind of come in and journal and share. A lot of the stuff was journaling is such a powerful tool. If you can't talk about some of the stuff publicly, a great way to start is just ah, you know, get your own thoughts on paper. Um, and this is a great tool to kind of go out there and express yourself on a daily basis, and they have a beautiful iPad app. So I've been, um, Max, the founder of There have been just talking through him on the board there, some talking through product decisions and kind of what he's focusing on. So I'm over true,

ventures. I'm a partner over there. And you know, the nice thing about Portland is it's an hour and 15 minute flight. So I'm down here, you know, like every other month or so, meeting with founders and chatting with folks. Um ah. I like Portland because it gives me the space that you can't have in the Bay area. So, you know, I'm on over an acre of land up

95:38

there, and I just got out in the woods. You're saying, though, is growing

95:41

mushrooms out there? Not the magic mushrooms, but more the lion's mane and things like that Wink. Yeah, right. I mean, I guess if I could, I probably would. But I'm not right now. I'm just getting winks on that. So, yes, I'm excited. Thio. I've got a couple girls under the age of two, and it's chaos at the Rose household. But ah,

it's nice to have a little distance, you know, after so many years, just running and running and running in the Bay Area like this just gives me the break that I need. In Portland, beautiful city with tons of hiking trails and a great food scene, lots of microbreweries, and it's just a fun,

96:15

fun place to live. That's awesome. Well, uh, can't thank you enough for for making the time. Ah, and you're quick trip down in San Francisco toe to chat with, ah, to chat with me and and for the listeners to get Tau listen to blow line version of of, um, of your story in the valley, but also, um, really, just also, I think you personally, um,

there's a lot to gather from this, the knowing what you're great at, but also ah, it's an interesting, interesting journey of delegation out of fear. Um, there's a real time observation right now, so I don't know how accurate this is, But delegation out of fear, Thio taking on too much too. Now, you know, board members and investor and working through these amazing founders and companies almost like the epitome of delegation, but picking your spots Ah, yeah. Helpful

97:7

and hopefully helping these founders, um, find and realize where they need to spend time and effort in in kind of addressing some of these more emotional sides of the journey because I think it's very easy to quickly jump into a product discussion. It's very easily to talk about Oh, I need to hire this VP of finance like That's but where are you emotionally and how can can I be helpful there as well, you know? And I think that applies the whole different not to go off on, go too much further to the broadcast. But I think that place is so many different things. Like one of the best things I did was invest in several months of, um, therapy with my wife before we got married and just being able to be on the same page on things and know that we're on the same team and howto have the tools in the toolkit toe work through arguments and disagreements in a very productive way. And that's led Thio a very solid, solid, amazing marriage and personal life. Um, that it just helps me so much more on the professional side as well.

So I think that the more that we can look about look at this as like a holistic like, complete picture of an individual, right, and take all that, um into consideration when helping out folks. Not that I want to dig into the personal lives of all my founders. But, you know, just sharing my own exploring the sidelines for that stuff, too. Yeah, exactly. In sharing my experience there, and if they want to talk more about, we can invent, that's fine,

too. So just, you know, just understanding that there's so much emotion wrapped up in all this stuff on so many different fronts. Um, but I hope that's what the world that we moved towards is something where, uh, I think men specifically have historically had a hard time with this with just opening up more.

98:51

Yeah, is ah. And I think episodes like this and and and founders like yourself opening up its is it gives permission opening upon failure, opening up on things I can't wait to have. Ah, a whole series of episodes with spouses. Yeah, because it is such a We talked about co founders like it is such a really part of of the journey that is, um, so under discussion. And that is a great idea

99:18

if you can have the founders thousands on and just big Okay, tell me what's up when he when this person or that person doesn't come home at this time of night and is pulling all nighters. And how does that impact to you?

99:29

And maybe the 1st 1 will be your wife and my what? Because it's ah, your wife is. My wife is a huge fan of of your wife and, uh, first off. But to, um, it's something that you have wanted to dio for for a while, because talk about below the line like that, such a massive part of that universe. And man, did they really bear the brunt? If you don't have a therapist or an executive coach, they bear the brunt of a lot of that emotional baggage behind. It was a founder myself. What was so interesting and unhealthy about is I would off load it by talking about it,

but then not realize she was internalizing it because it's It's like an investor that can't help right, because it's removed from the equation but knows there's really tough things going on. And then she would sit with it and just me verbalizing it, decrease the size of the problem, you know, tenfold. But then she didn't. She was removed away. She couldn't actually help solve it, and therefore just it remained really big. Ah, for her. And and I had no idea that years of this was happening. Um, so, yeah, it's ah, completely under disgusting act.

100:37

I told myself it is somewhat related. I told myself that if I ever build another company and they we reached 20 or 30 employees, I I wanna have a full time therapist on staff that you can go in your it's required. It's part of your job. You get, you know, an hour week or whatever. Maybe, and you can go in. And it's, of course, completely confidential. Like all locked down under those aspects of the CEO doesn't read any of this stuff. But you can talk about work and talk about personal things. You talk about anything you want. Yeah, it's just an hour to decompress.

101:8

Bringing your spouse. Yeah, whatever. Bringing your mother and I a second on the premarital kind of counseling. It's, um, my wife and I got to do that through our church, offered it for free, and, uh and it was here in San Francisco and and I think that it was part of it was like, this is kind of like, Is it gonna be kind of Ah, Brainwash e. And it was It was so amazing to have every week for I think was like, nine months of just, um, having this this.

Yeah, they Now it's becoming mainstream tohave executive coaches that work with executives of your company, and yet it's still a couples therapy is still this thing. That's, you know, it's in the shadows are in our corner crazy. So

101:57

power means just tools, right? What they're doing is there teaching you like a good therapist in my mind is someone that will equip you and teach you how to deal with the complexities of the interaction with another being 24 7 cause you're always with them, you know, they're they're in your household, um, when they're not there. So in theory, like what we did is we kind of quote unquote graduated from this. There was we had a lot of new skills and new tools. And then, you know, if you ever need them, they're just a phone call away, but that you have this like a deeper understanding of each other, and it just it's been so awesome ever since we did that. So I love

102:38

it. That's awesome. Well, it's l dropped it down for for future episodes to dive into this stuff. Well, Kevin, thank you so much, man, for the rest of time in San Francisco and hope to talk to you soon on a part two. Yeah, more that we could go on for you. Thank you. Thank you. Friends and listeners. I hope you enjoyed today's episode. If you want to hear more of these types of conversations, go over to your favorite podcast app and hit, Subscribe or leave us a review. Good or bad love hearing from people that that appreciate this type of conversation and want more of it. You can also follow us on Twitter

103:20

at Go below the line. Well, a CNR Twitter bio.

103:24

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