KP's Reflections on Turning 55

What matters after decades of building, losing, and rebuilding?

In this episode of KP Unpacked, KP Reddy turns 55, and Nick uses the milestone for a lightning round conversation exploring career highs, crushing losses, and the philosophy that's shaped three decades of entrepreneurship. From living in a truck eating 19-cent tuna to running a VC fund, KP reflects on the moments that actually stuck and why they weren't the trophy wins.

The conversation moves between tactical and existential. KP explains how Claude Cowork is now his nurse practitioner (drafting insurance appeals, scheduling appointments, analyzing x-rays), why he runs four Mac Studios doing different jobs while he unpacks office furniture, and why the future of CRM is taking people to lunch instead of data entry. But the deeper thread is about identity: why his worst fear (going back to zero) doesn't actually scare him, why his family has more confidence in him than he has in himself, and why the 2008 financial crisis validated the self-doubt that still drives him today.

Key topics covered:

• Why KP spent his 55th birthday at the DMV after his assistant cleared his calendar without asking
• How Claude became his healthcare coordinator and delivered better emotional support than his mom
• The blank slate moment after his first exit paying off the house and feeling peace, not accomplishment
• Living in a truck with sleeves of tuna and stolen mayo packets and why going back doesn't scare him
• The 2008 crisis, personal guarantees, and why losing everything validated his lack of confidence
• Why "celebrating small wins" is for people not building unicorns assume wins, magnify losses
• Vibe working: running four Mac Studios with Claude Cowork while doing manual labor he actually wants to do
• Why relationship-driven CRM beats software: take engineers to lunch after RFP meetings, not Salesforce data entry
• The manager vs. maker schedule and why KP operates at sprint speed with no please-and-thank-yous
• Morning meditation as leadership: visualizing every founder and team member's context before the workday
• Why one founder said "I can feel when you're praying for me" and what that reveals about leading mission-driven teams
• The 10-year goal isn't three private jets, it's building community where all LPs are former founders who exited and came back

If you're navigating what success looks like after the wins, trying to lead without micromanaging while operating at full speed, or wondering whether your worst-case scenario is actually that bad, this episode will reframe how you think about ambition, fear, and what matters most.

Listen now.

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Chapters

• 0:00 Milestone Birthday And Admin Day
• 3:18 AI As Nurse And Translator
• 6:33 Safety Fears, Resignations, And Hype
• 10:03 Identity, Jobs, And The Generalist Dilemma
• 14:18 Vibe Working With AI Co-Workers
• 19:03 Freeing Time For Real-World Moments
• 22:33 Relationships Over CRMs
• 27:03 Lightning Round: Books, Kindness, Wins
• 31:03 Failure, Doubt, And Starting From Zero
• 35:33 Meditation, Context, And Leading People
• 40:33 Manager vs Maker Tensions
• 44:33 Hiring, Pace, And Ownership
• 48:33 Five-To-Ten Years: Choosing Community

Transcript

SPEAKER_01: 0:35

Hey Nick, how's it going?

SPEAKER_00: 0:38

What's going on today? Big episode.

SPEAKER_01: 0:41

Yeah, one of us had a birthday.

SPEAKER_00: 0:43

Yeah. How was your birthday?

SPEAKER_01: 0:47

You know, 55 is supposed to be a milestone birthday, etc. etc. Right. I guess, you know, it's a milestone birthday, but we just chilled out. There's you know, we just stay so busy at work that I don't know if you know, like it was kind of funny my assistant cleared my calendar for the day. Okay, including rescheduling our podcast, I think. Oh yeah. I didn't ask. I didn't ask her to. And so I was like, hey, did you know, did Rachel have you do that? She's like, no. And I'm like, like, why would you clear out my cal? Like, and she's like, I don't know. I thought you'd like want to take the day off for your birthday. That's like, you literally get Slack messages from me on at two in the morning on a Saturday.

SPEAKER_00: 1:32

Why would you think I want to take any time off of work? I like I like working. Like, this is what I do. Like, what are you talking about? That's really funny. I mean, I think that's I mean, what it I think that's a cool quality. Human, very human quality. I don't think the chatbots would know how to the chatbot assistants would know to uh to treat you that way. Yeah, I thought it was kind of funny.

SPEAKER_01: 1:56

That's awesome. I was like, it's like you don't even know me.

SPEAKER_00: 2:01

So did you just hang out at at home and go to the beach?

SPEAKER_01: 2:05

Like what was the what was oh, this is the best part, right? So I was given a free day, right? So what do I do? I schedule a doctor's appointment that I've been putting off. And we hadn't like we haven't like transferred all of our stuff to California yet. So I went to the DMV to get my license for night. It's a big birthday, but it was kind of funny though, right? Like big birthday activities. It was more like I have an entire day wide open. What am I gonna do? What should I do?

SPEAKER_00: 2:37

Let me do all the administrative administrative items on the to-do list, the most painful ones will be the most satisfatisfactory ones.

SPEAKER_01: 2:47

But you know, that it is one of those things, right? As much as we work, there are like these administrative things in our personal lives that we just procrastinate, and you know, and it they always rear their ugly head when because of course I have to renew my tag by the end of the month, but I can't renew my tag unless I have a California. Like it was just like, you know, I could see March rolling around and getting pulled over by a cop. Like, sorry, I'd sorry, officer, I didn't have time to deal with all that. You know, it's like, yeah, okay.

SPEAKER_00: 3:19

But sorry, you've been in California for over a year. Come on.

SPEAKER_01: 3:23

Yeah, here's a$500 fine, so like, you know, that kind of thing. So it's hard to make time for those administrative things. But you know, hopefully I'll I mean, I've got uh Claude Cowork working with my app, with my doctors, my pharmacy, my insurance company who denied one of my claims, and I had it look at the letter and say, draft me a great appeal back, we'll see what happens. Send me mess, send a message to the doctor to make sure they did prior authorization. So it goes into the app and sends a message to my. I mean, if I can get that, you know, for those of you that don't know, I've been diabetic for 30 years now. So just it's a maintenance thing, right? There's always some doctor's appointment, go see your eye doctor every six months. There's just a lot of the things that you know, some of us in our 30s that are not diabetic probably don't go to the eye doctor every six months and to the dentist. Like, I have to do all those things, right? So, so if I can get it being my nurse, practitioner of sorts, scheduling and coordinating, which by the way, I've been having this rotator cuff. Like now we're talking about like whatever, but like this rotator cuff thing that I've had for issues that happen after the age of 55.

unknown: 4:44

Yeah, pretty much.

SPEAKER_01: 4:45

This was before that. So I went and got an x-ray. And of course, in the app, it says, okay, here's what the x-ray showed, right? None of it looked like English, it was all Latin, right? So I cut and pasted it into my Claude and said, What the hell are these people talking about? Like, what do I need to know? And explained it all, right? It explained everything. Here's what you need to think about. Physical therapy is probably your next step. However, also you're diabetic, you should be a little bit more careful. And at the very end of the narrative, it says, it said something like a lot of people depend on you to be healthy and please don't procrastinate getting this looked at. You need to take care of yourself. I was like, I don't get messages like that from my mom.

SPEAKER_00: 5:41

They're very good at what they do, those AI researchers, aren't they?

SPEAKER_01: 5:45

It's very good. I was like, felt so nice. Felt so nice.

unknown: 5:48

Yeah.

SPEAKER_01: 5:49

Claude cares.

SPEAKER_00: 5:51

Yeah. That's cool. I'm glad I'm glad that uh most of your emotional wins from your birthday came from Claude.

SPEAKER_01: 6:03

Tis the future. Tis the future.

SPEAKER_00: 6:06

This is this is a good a good segue into the topic of today's show, which is there is no current event topic. We're gonna have a fun, more introspective conversation about your life and some learnings that you've had. Good birth birthday, birthday consolidation episode. Yeah, you were you were feeling quite introspective and reflective in the last couple weeks. And so I thought, you know, somewhat of a light week, news-wise, no new model releases, no, you know, big acquisition in the industry to talk about. So yeah, I wanted to Yeah, nothing big.

SPEAKER_01: 6:43

I think so. This episode will be named Nick Makes KP Feel Old. Potentially, if I am good at what I do, yes. There are a little minor minor things in the world, right, that have happened. So Claude for Claude Co-Work for Windows came out.

SPEAKER_02: 6:59

Okay.

SPEAKER_01: 7:00

For all the corporate people that listen to this, all these AEC firms that are quote unquote Windows shops and are have been crippled by using Microsoft Copilot. So that news came out. The head of AI from Microsoft said, due to the changing relationship with OpenAI, they're gonna actually release their own LOM. It's in the works. Apple said it's now delayed 10 months to deploying their AI feature again. They should maybe try Cloud Code, maybe that'll help them out. Which is funny, Cloud will probably come out with an iPhone feature before Apple does, right? Kind of thing. And then the more interesting thing, in terms of like the dovetails into some of the beginning of this conversation, was this this engineer from I think it was either from OpenAI or Anthropic, I can't remember which one. He said he quit, he resigned. Yeah, I saw that. And he's moving to London and is gonna write poetry until all this AI stuff blows over. Which is like, you know, should you be scared? You know, for those of you that don't know, not everything on Twitter is truth or real, by the way. Including the video demos of what people are doing with Moltbot or whatever is out there, you know, like try it yourself. So, anyway, no, I I thought that was kind of an interesting like hey, I'm out of here. Let me know when it gets better. Like, I don't know what's gonna happen, right?

SPEAKER_00: 8:35

The it's true, the AI conversation over the past week was it felt more about safety than anything else. I would add one current event of of that that viral article that went really, you know, just was trending on on X that basically was a letter. It was a um an individual who has an AI-based software company. He's more or less building on the on the on the frontier and on the front lines, and you know, is trying every model release when it comes out. And he wrote a letter to his friends and family, I think got something like 50 million plus views in two days. And it more or less was like, hey, here's like there's been a lot of progress. We've covered most of it in our conversations. But to someone who's not experiment experimenting with Claude and experimenting, you know, kind of daily with with AI tools, here's what you need to know. Here's the good, here's the bad, here's the things to, you know, be euphoric about, here's the things to, you know, maybe be fearful about. I feel like it, you know, I I read it a couple times, and to me it had a little bit of fearful tone to it. Like it was more like to me, the intent was hey, you need to be aware because things are things things are are getting pretty intense if you're in if you're in tech. Yeah. Uh there's a lot of anxiety, you know, people were concerned about losing their jobs because of how you know how quick how quickly the models are improving and how they're recursive and doing their own development and all and all that sort of stuff. But but yeah, I do feel like you know, you're to comment a little bit on that, on the letter. I read it. It's hard to know if that individual, and you know, I I never heard him talk. I don't know really much about him at all, other than that he was, you know, leading AI safety for anthropic. And so you do have to take, you know, you have to take his level of seniority there pretty seriously. It felt a little performative to me. Like it felt like I read the letter and it was per it was had like you know, profess professional, like he he took the time to put it in a word doc. Like he was like a professional, you know, screen grab. There were citations in the letter referencing, you know, source material. Yeah. It was not off the cuff. It was not like, hey, I'm leaving anthropic and I'm gonna go, you know, I'm taking time off and going to write poetry and I'm like rethinking my life and all, you know, all the things that you mentioned. It was it was like it to me, it clearly was written by AI. It had, you know, it definitely had some of his core beliefs and thoughts embedded in it, but it was also very ambiguous. And it you know, it felt it felt performative to me. And I don't I didn't really know how to interpret it because it I wasn't quite sure what his intention was.

SPEAKER_01: 11:28

Yeah. You know, it's but it's interesting, right? And I'll let you kind of ask me questions that you want to ask, but I do think, you know, I wrote a sub stack this week too that came from one of my startups, a board meeting I was sitting in where the founder basically said his CTO or his VP of engineering, I can't remember, is like unwilling to look at AI coding, that it's all trash, it's all garbage. I was like, whoa, like I'm not saying perfect, and I'm not saying, you know, it's like you you you you can't say you're not looking into it, right? But it came down to this idea that like this high definition of someone's self-worth, career, heavily driven uh into them, right? And I think a lot of our listeners that are you know they're civil engineers, they don't do civil engineering, right? If someone asks you, what do you do, they don't say, Oh, I do civil engineering. They say, I'm a civil engineer, just like a doctor says, I'm a doctor, I'm an architect, right? There's just so much, like there's just so much tied to like who I am and what I do is sometimes the same thing, right? And I was talking actually, I was talking to my middle son about this this morning, you know, and all those AI conversations, right? Because he's getting ready to graduate, he's like, Dad, I'm not I don't know what I'm gonna do. And he was like, Dad, what do you what do you do, right? Like, what do you how do you I was like, I'm a business man. He's like, he's like, Dad, really? It's too early for Jay-Z. What are you doing? But as we think about my career, right? I don't know that I can tell people like what it is I do. Like, what do I do? Right. Because I I think I've done so many different, I've done like whatever I wanted to do.

SPEAKER_00: 13:24

I I think that that's a core fundamental of the managerial class is you do, you know, you do a lot of ambiguous things throughout the day. And it might be, you know, and and and cross-funk, it's cross-functional. Might be sales, might be engineering, might be product, might be, you know, you might put your investor hat on and do some portfolio analysis. But I think like, you know, if you extrapolate that, and you and and you know, I'm speaking kind of towards your day-to-day, but if you extrapolate that to, you know, your average knowledge worker, who by the way, I'd put a civil engineer in that category. Like there's there, you know, many, you know, many, many parts of the job are, you know, it's it's knowledge-based, it's it's competency-based, you know, it's a cognitive function. And there's not like a clean definition of like, hey, here's what I do every day, here's the value that I add. Right. Because you're pulling on you're pulling on so many different threads, you're crossing so many functions, and and in some ways, like you you're just like everyone today is the ultimate generalist. Yeah. And so it is hard to describe. And I do think that also is why people have extreme anxiety when thinking about how their life and their career shifts related to AI is because you now have this commoditized form of intelligence that is an amazing generalist. Like the best generalist I know is a language model that you know we get to interact with every day now. Yeah. Knows a lot more than I do as a generalist, right? Yeah. And so it it challenges you because that used to be your core value, is like you could do all these, you could, you could do a lot of a lot of things very, very well and flex up and down at like your you know the human brain. But now that's being replaced. So there's a question of like, should I should I specialize? Should I go deep into something? Should I, you know, should I master anything? Or do I become, do I go more abstract and become, you know, do I become an artist?

SPEAKER_01: 15:46

Yeah, you know, it's interesting, right? So because of all this claud co-work, right? We we've been talking about vibe coding now for a couple of years. Everybody, I think it was someone from Anthropic said it's now vibe working, right? Which is like, okay, whatever, people. Come on, let's just keep doing this. But then I started thinking about it because you were asking me about all my little friends in my background, right? My little Mac Studio friends. And like, what am I doing? I'm like, well, I've got them, I've got like four of them running co-work. And you asked me, like, well, what are they all doing? I was like, well, you know, I've got recruiter and I've got this person, you know, I've got I've got them doing different things, right? And the main reason I have separate machines is they if you start giving them complex tasks, they kind of take over your machine, right? They're running all the different tabs and it's popping up Excel. I mean, it's like you can sit there and watch it work. And so when I think about how I'd like to work versus how I've been told to work, i.e., do you come into work every you wake up and you're like, okay, here's the 10 things I need to do today? Probably not. You're probably like, here's the four meetings that I need to do today, because they're on my calendar, including recording this podcast with KP. It's on the calendar, right? And then in between there, you're really maybe reacting. And if you're not reacting, I would say you're kind of vibe working, right? We part of our job is to go down the rabbit hole, right? Like, oh, what's this thing? What's this new thing? Okay, damn it. And the next thing you know, an hour has passed, like, oh man, I gotta get on a Zoom call. I just went down this rabbit hole, right? So when we think about other than maybe certain deliverables, like a shadow, you were, you know, you and Matt were cranking on the annual report and trying to, you know, those are very external deadline driven. A lot of the work that you do on any given day or I do is not really that deadline driven. It's like the work we think we need to focus on and prioritize in between the work we have to do. And I feel like that is vibe work. I mean, not to be weird about what everybody calls things, but I feel like that is vibe work. And I think that's how I like the work. You know, I don't know that I come in with this, like, you know, I would say the power of unleashing my ADHD in this day and age, it's like insane, right? Because that little idea that pops in, which you know, people know I write every day and I write a lot. And part of the reason I write is it's my therapy to get ideas out of my brain so I can move on and do work. And so all my Substack people get to benefit from whatever was on my brain that day, right? So that's part of my method is I don't earn my second cup of coffee until I write a thousand words, and not all of them I publish, but sometimes it's gibberish, and I publish it out there. And that's when people say, like, how do you write so much? I'm like, if I don't write, I won't get anything done today, right? So it's it's part of my therapy, so to speak. But now I'm not only like writing, those writings are turning into instructions to my little army of co-workers, right? Which means I am kind of vibe working. It's like whatever pops into my head first thing in the morning. What am I thinking about? Um, which I think for the generalist, right? I would say not just the generalist, but the curious, being intellectually curious, and you know, I think that drives this behavior, right? So I don't know.

SPEAKER_00: 19:26

Like, I think for a lot of people that come in and it's that are much more list-oriented, administratively oriented, I don't know how they're gonna feel when you have a coworker that is doing a lot of the tedious like work for you day to day, and you're directing it, you're the barrel, you're the barrel and it's the ammo. It becomes a different it becomes a different work function. And I think that's that's where the the label from an engineering standpoint of vibe coding came into play because you're just directing it with the English language and and telling it essentially how to function and what you need done. It still requires working, like you still have to instruct it. And if your instructions are terrible, it's not going to give you anything. There's the output, it's gonna be terrible. So you still you still do have to work, but it's not this intense head down of like, I am the only person that will that can complete this function. You're now interacting with either, you know, a coworker or a fleet of co-workers, and you're not actually doing 100% of the work anymore, which is weird.

SPEAKER_01: 20:39

Yeah, so just to hear like a real experience just now. So we moved into this new my cool little office in Half Moon Bay, which I guess you're gonna probably maybe visit next week if you have time. But yeah, we just have never we still haven't moved in. We're still like kind of moving in, right? We got our computers and monitors set up, and then the rest of it's like in boxes. And so I had I gave co-work to four of the machines and said, Okay, here's what I need to do, and I let them run. And then I went and started unpacking because I can't get co-work to unpack, right? And so Devin walks, he's like, Dad, like, what are you doing? Like, what are you having an OCD moment? What's going on in here? Right? I was like, No, I'm like, I'm working, man. Like they're they're doing all the things I need to do for the rest of the day. I want to clean up, you know, and I've got this like amazing, like old school radio that was my dad's. It was like his first big paycheck. He went out and bought this Grundig radio, which is like a console, right? It's like maybe six feet long. I mean, it's it's a piece of furniture like they used to do back in the day, and so I've been carrying that thing everywhere I go, it kind of comes with me. So I finally like got it set up. It doesn't work, but it's just like a cool piece of furniture for me. So I'm like working on that and fixing the legs because the legs are a little, you know, definitely like, Dad, it's like middle of the day, what do you do it? Like, what is going on here? I'm like, no, I'm working, man. But for me, it was a nice little release, a little nostalgia, right? A little reflection and you know, fixing my dad's old radio, getting my space set up the way I wanted to, which by the way, my in-laws are visiting and they want to come visit the office. And I'm like, you can't visit, right? Like it's just a bunch of boxes, right? Um, but I was just thinking about that. Like, that is something I wanted to do in that moment, and I didn't have to procrastinate.

unknown: 22:34

It.

SPEAKER_01: 22:35

And it was something I kind of wanted, like, I could have gotten my handyman in here to do something, you know, like whatever, you know, hey, go get that set up or whatever. I could have outsourced it. I'm very good at that. I'm I'm a very loyal customer of TaskRabbit, but I didn't. I chose to do it myself because I wanted to.

unknown: 22:53

Right?

SPEAKER_00: 22:53

I thought it would be a year ago, you would have Task Rabbit that 100%. That thing. Yeah.

SPEAKER_01: 23:00

And then complained afterwards at how crappy of a job they did.

SPEAKER_00: 23:05

So you miss so you so a year ago you miss out on the nostalgic experience. Yep. You didn't have the also the satisfaction of doing some work with your hands. Yep. You are a civil engineer, right? Yeah. Like you like to see tangible work done, not just computer abstract work that we've gotten sucked into, right? Um that I mean it it's a nice, it's a nice thing. I think it it's like I feel like that is not talked about enough of like the fact that you're you're you're able to you're able to work and still have now have those experiences because you're not excruciatingly in every single detail and and 100% responsible yourself for the output you have helped. Yeah.

SPEAKER_01: 23:59

Yeah. So I mean, I think that's ultimately that's what for me, like, you know, it's like vibe working, whatever. But I do think other people have to start thinking about like, hey, I do have extra time. And I'm not saying like go move to London and write poetry kind of stuff, right? I mean, when's the last time you took not a deck direct report to lunch, but maybe someone another level down in the org? When have you taken like someone that just started like a few months in that just started with your company and say, hey man, like let's go grab a sandwich together, right? Like it maybe it frees up more time for those types of things. In fact, it's kind of interesting. I think I wrote about this. I don't know if I don't know if we talked about it, but my first job out of college, my boss, when I was doing business development, I decided I wanted to do some business development. He's like, sure, no one else wants to do it. It's a bunch of engineers here. Nobody wants to go talk to customers. Go do it. And he would judge me by how many business cards I would bring back from conferences. And I would have to sit there and go through them and explain like the conversation I had. I had little notes on the back, like super old school, right? And then as he got comfortable with that, he was like, my incentives were driven by how many people I took out to breakfast, lunch, and dinner and take out golfing. That was my like there was no CRM, it was a stack of business cards. And hey, who'd you take out? Like my expense report was actually like it was a good thing I was spending money. Right. And I kind of feel like that's what that's what we should be doing, right? The new the new CRM is not using Salesforce or whatever to track leads. The new CRM is actually going and building relationships in person. And maybe those young engineers that you're like, oh, go respond to that RFP. It's like, hey, how about you at that at the end of that, you know, that they usually had those little kickoff meetings at RFPs like, be sure to take some people out to lunch afterwards. And I was like, well, no, no, I need to run back and I need to work on this roadway alignment or whatever it is, you know, like I don't have time for that, right? This I don't have time, I gotta get back to the office thing. I think that's really the future. It's like, no, you have plenty of time because AI is drawing that roadway alignment, right? AI is doing a lot of that heavy lifting for you, so you actually do have time to, you know. I'm not sure where like CRM became software, right? It's like it's become software, whereas relationship management, customer relationship management can also be a verb.

SPEAKER_00: 26:44

There's um yeah, there's an interesting thing there where maybe previously, if you're a salesperson and you're you have a little bit of downtime, what are you doing? You're entering data into the CRM, you're cleaning the CRM up, you're getting ready for your sales meeting, you're doing admin stuff. Like that's what you do when you know you're not making, you know, you're not on a Zoom call, you're not, you know, dialing for dollars. Maybe you're maybe you had a trade show, you attended. I it it's an it's an interesting concept of like maybe you reinvest that into actually where you should be spending the time anyway, which is just like being out in the field and taking people, you know, taking people to dinner, building relationships.

SPEAKER_01: 27:29

Yeah, it's interesting. When I had my much larger company back in the day, I'd walk through the cube farm and all the salespeople would be in right before lunch and they're all on their computers. And I was like, guys, like, why are you here? We're not a retail operation. The customer doesn't walk in through the front door and ding ding ding, and you go running, hey, how can I help? Like that's the customers are out there. If you're in here, you're not doing your job, your job's out there, right? Going and meeting people. So I think, especially in our industry, that's super relationship oriented. And I do think we're gonna see a fall off on some. I think we overconferenced ourselves post-pandemic. And I think you're already seeing some of the conferences earlier in the year where attendance has been way down. Um, I think people are less interested in these big conferences and more interested in smaller settings and one-on-one meetings and things like that. Okay, you're ready to transition to the phone part.

SPEAKER_00: 28:35

Series of lightning round questions for you for your birthday. These are things that I actually don't think I know most of the answers to, so I'm excited to hear you roof. Okay, so what first question what's your favorite book that you've written?

SPEAKER_01: 28:51

That I've written? What you know about startups is wrong.

SPEAKER_00: 28:56

Yeah, I would have guessed that one. Yeah, that's your best one. It's just very personal.

unknown: 29:00

Yeah.

SPEAKER_00: 29:01

Okay. What is the kindest thing that someone has ever done for you?

SPEAKER_01: 29:10

I have this like client, and every time I see her, she brings me a bag of coffee, like coffee beans. Right, by the way, she she's my client, not the other way around. And it's like from her travels, and she's like, I go into these like really cool coffee shops, and they have really cool bags of coffee. She's like, I don't drink coffee, but I know you're a massive coffee drinker, and so I always think about you and buy you a bag of coffee. It's just like kind of random, and like it's a little bit like the the I enter, you know, it's like the thought, right? And then kind of executing on it, right? And I think that's it's like one of those little things, you know, like unexpected, but also interesting.

SPEAKER_00: 29:54

Yeah, that's a good one.

SPEAKER_01: 29:56

I'm sure there's a lot more. That's just kind of top of mind.

SPEAKER_00: 30:00

But okay. What is the what's the best, most exciting memory you've ever had work-wise? Was it I mean, my a couple of thoughts were like related to your your IPO back in the day. I'm sure that that's up there. But yeah, talk talk to me about like big wins that you've had that you've had that have stuck with you for all these years.

SPEAKER_01: 30:28

Yeah, so it's it's kind of interesting, right? So that first win I had were, you know, and my big liquidity event. The next day I paid off my house. I paid off all the debt I'd accumulated. I paid off my house. And I was like literally like we're in this little starter home, right? Nothing, nothing amazing to brag about, right? It was just like kind of that back then the the$99,000 house, if you can imagine, that we bought at 99,000 brand new, by the way, from Pulfy. It was a hundred thousand dollar house. But I remember sitting at the kitchen table, looking out to our porch, and just like very peaceful. It wasn't even like an accomplishment thing, it was more like blank slate. And I think you know, when I see and I think those blank slate feelings, whether you're exiting a company, or quite honestly, sometimes, like you know, I went through a divorce, very tough in the in the in the middle of it, and very tough, like with the boys and all those things, but there was a time where it was like a sense of relief, like, okay, I'm moving on, like I'm not trying to fix all the things and make it just all that stuff. So I I like these like blank slate moments, and I think they're so important, right? I think whether you're exiting a good, good or bad exits, right? But just to be able to like take a breath and it's like blank slate, now what am I doing? Right. Um, personally or professionally, I think it's it's it's like life is compounding, both good and bad, right? The bad things kind of compound as well. And so I think kind of cleaning the slate, you know, I think is probably one of the most memorable. That was the first time that happened to me. It was very memorable. Like I can still feel the air, so to speak.

SPEAKER_00: 32:30

Was listening to a podcast about Andre Agassi and the tennis player. You read his book, by the way. I haven't, yeah. Oh my god, it's gonna be a he would love it.

SPEAKER_02: 32:40

Oh really?

SPEAKER_00: 32:42

Yeah, it's good. I'll have to I'll have to bring a bring a copy to Calgary. It's called Open, but um his life is just super interesting. He had a dad that was incredibly hard on him, taught him how to play tennis, but basically forced him to play tennis. He he hated playing tennis, and he became the best player in the world and like still to this day hates playing tennis, but just does it. Yeah. But one of the I was listening to this podcast about it, and one of the questions was what were some of the most painful losses that still sit with you in your retirement? And he like rattled them off. Like, there's still you can just tell, like, they're just searing at his memory. Like he like wakes up in the middle of the night and thinks about tennis matches that he lost that like in the grand scheme of things aren't that big a deal, but in the human existence, you know, were really painful and they were great motivators for him to get better over time. But I'm curious, like, yeah, when you think about losses, failures, things that you look back on, you know, related to your career and even life, what are some of those that that that stand out for you?

SPEAKER_01: 33:48

Yeah, I think you know, post 2008, you know, when the economy just tanked, my BIM company having to, you know, sold it slash shut it down. You know, I'd love to say it was some massive great exit. It was more of a, hey, we want to hire you and your team. It was more of an aqua hire, right? It was really tough because of the the it was like a rocket ship. They just came to a halt, right? When when the great financial crisis happened, right? And so that was just, and that was really tough because I wasn't taking a salary, you know. So for my family, it was like, yeah, I don't need a salary. I'm gonna hire one more salesperson instead of take a salary, right? Because things are just doing this. And then when they did that, all of a sudden it was like, oh, you personally guaranteed that line of credit for the company, which was like a conversation with my ex-wife, you know, like all these things like all of a sudden hit me, both professionally and personally. And quite honestly, I think a lot of it was there's a weird thing that even now there's this idea that like that I'm very confident. But my wife will tell you that sometimes she thinks that I'm it's actually what drives me is my lack of confidence. Like, I still believe that if everything blows up tomorrow, like I'll be back to living in my truck like I did in college. Like, yeah, that it's gonna reset to zero. And she's always just like, you don't think you'll get a job? Like, you really think everything you've done in your career, nobody's gonna want to hire you. I'm like, No, I'm like, I don't know. I mean, maybe, like, who knows? I was like, who knows? Like, and she's like, You're insane! Like, they're like, in what world do you not have a job offer the minute you're available? Or that someone wants to wants you to consult with them? Like, I just I don't know. She's like, it's wild that you think that way. So, even like that healthy doubt, should say it's unhealthy, but I think at that moment, I feel like that that doubt I've had, that lack of confidence I had, that moment became a data point for I'm a good thing I'm not that confident. Good thing, yeah, see, I I knew this could happen, right? It was almost validating my lack of confidence. So it was really, really tough. Like in the world of like you know, being right, right? Just being right. This is one of the things maybe you don't want to be right about, right? And in 2008, I was like right about like, okay, what am I gonna do? Like get rid of all this personal guarantee stuff, blah, blah, blah. You know, it was just like it was just that moment in time that it's like that my worst nightmare was kind of happening, and of course, I was probably you know, not in the best mindset either, right? Because at that point, it was affecting everybody.

SPEAKER_00: 36:52

Yeah. Question on the on your worst fear visualization of you going back to living in your truck, does that scare you? Or is that is it, you know, have you moved past that that like if you know if things end up there, it's actually not that bad because you've done it before?

SPEAKER_01: 37:11

It doesn't scare me, like starting from zero does not scare me at all. Um and I think back to clean wiping this lake clean, right? I think starting from zero in my world of personal relationships, like I do think my family and my kids, I've my kids especially, I've raised them in a way that I think if dad went to zero, they wouldn't be like, you know, you deserve it. They're like, hey dad, like you'll figure it out, right? I mean, I think they're they're very much they had I would say in many ways, my family has more confidence in me than I do. Like that, even if you ended up in a car, like you'd figure it out, right? You'd figure it out. But you know, there is something like I have a friend going through a divorce right now. Three houses, all the cars, all the things, right? And my first reaction was like, Okay, this sucks, right? But my second reaction was like, Oh my gosh, you have so much to unwind, like all those trophies of your success, and even like you know, the mansion spending a decade taking care of it, right? Like planting things, like just all that investment, right? It just made me really feel like I just don't want stuff, like because it feels like there's this, it's like this massive like stacking of stuff that maybe one day if I have to if things don't work out and I gotta go live in my car, like I gotta go figure out how to deal with all this stuff, right? And so I don't know, like I think the why you do it is so important. You know, I was talking to one of our founders the other day, and he said something about celebrating the small ones. I was dude, stop it. Like, go get some big ones. Celebrating the small ones is a lack of ambition, you know, and he was like, Wow, like that's contrary to everything I've ever heard. I was like, celebrating the small wins is for people that are not trying to build unicorns. Do not celebrate the small ones, the small ones are assumptions, right? Now, the small losses magnify the crap out of them and fix them so they don't get bigger, right? And it was just like, oh my god, like you're giving me all the opposite advice of anyone. I was like, I just feel like you're too comfortable with the small ones, you know, and I so I think, but my psyche of being comfortable of going back to living in my truck and eating, you know, I used to buy sleeves of tuna cans that was like my food in my as I saw I actually just got rid of this duffel bag. I used to keep my sleeves of tuna and packs of mayo that I would take from Chick-fil-A so I could have mayo on my tuna. It doesn't really like it was like one of those things in reflection, it was like the best of times and the worst of times.

SPEAKER_00: 40:07

100%. You know, life is so simple with that in those phases.

SPEAKER_01: 40:13

There you have manageable, man.

SPEAKER_00: 40:15

You have zero, yeah, zero concerns, zero dependencies, zero responsibilities in some ways. Like you are free to just salt, you know, focus on focus on the day to day. Yeah. Kroger cost cutter tuna.

SPEAKER_01: 40:29

I was getting it on sale for 19 cents a can, crushing it.

SPEAKER_00: 40:34

No, no, no work, no worries at those prices.

SPEAKER_01: 40:38

No worries. And I would like I'd like to filth some, you know, saltine crackers and stuff from Arby's, like whatever.

SPEAKER_00: 40:44

I mean, that the reason I ask about your whether or not that's like a scary scenario for you, it's like what I've found is those like that fear is a very common fear of like you know, the fear of going to zero. That's you know, anyone who's who's who's built a good career is like always worried worried about the rug being pulled out from underneath them. And and then yeah, and then I I think that one of the most powerful visualization exercises you can do to get over that fear is actually just go back to those moments when you didn't have anything before you had the trophy mansion and before you had the car, and before you had the status of success. And usually if you actually spend time with those experiences, what most people find is that they actually were quite pleasurable, quite, quite, quite simple and quite romantic.

SPEAKER_01: 41:36

Yeah, you know, it's really interesting. You you may or may not know this. I don't know if I brought it up before, but like in my morning meditation, right, I actually visualize everybody on my team, including you, including our a lot of our portfolio portfolio companies, right? And I kind of visualize and like try to think like like wish the best for them, like whatever best is, right? And you know, and I know you're thinking about some life changes, so those are the kind of things it's not always like work, right? Like, you know, I'm praying for Nick to get the annual report out. Like, I don't, that's not important, right? But it's funny, one of our founders pulled me inside one day and he's like, I can tell when you're praying for me. And I was like, Really? And he was like, he's like, Yeah, like he told me that, and like now I feel like I can feel it. That's just like such a cool thing, right? But you know, I don't think I really think like when I think about like what I want, what's best for people in my life, I don't think it's ever about like money or success. It's usually all the other things because I feel like if you look at any of our founders, of course they know they need to grow the like everything that is expected of them is fairly obvious. It's really the other things that I feel like they're blind spots that I'm really like thinking about, right? Not not the obvious, like, oh, I need to go get my series A. Of course, you know, like I'm not gonna pray for them to get their series A, just go do the work and you'll be fine, right? It's the other things that I think that maybe they're missing in their lives that I tend to like think about. But you know, it's it'd be ends up taking up an hour in my morning. That's we need some outcome. We need some outcomes with some of these portfolio companies. I'm running out of space.

SPEAKER_00: 43:31

Send the right energy their way, and yeah, we'll we'll uh I think yeah, those problems will be solved. Yeah, the it's an interesting thing to think think about management in that way, like just to start, or it's like a part of your leadership, a part of your man your management, thinking about the context that your team your team is in every single morning. I think we'll do that because you know, most management is just you know, you're trying you're met you're you're trying to get to a specific output, maybe you're measuring some inputs that that get there, maybe you're just you know looking at the end results every quarter. But I feel like the the day-to-day friction and where you run into issues, you know, with people on your team that aren't performing well or that you know are struggling with personal issues, it's it's like pushing them when you're not quite understanding of their context. Yeah. And the more you can tap into their context, and it's funny, I'm using that word. Because it's used so often in the AI world. But that, but, but that that context is really important in order to lead people effectively.

SPEAKER_02: 44:43

Yeah.

SPEAKER_00: 44:44

And I think that like maybe that meditation exercise is potentially the most powerful way to get context. It's just like goes a level deeper than you know communicating what's going on day to day.

SPEAKER_01: 44:55

Yeah, because I think sometimes when you're like kind of wishing the best for people, it doesn't mean that they're going to be employed by you. It doesn't mean that they're going to be your partner and the, you know, it's not tied to that. And in fact, sometimes when you're like thinking about these things, the mess, the best solution may be that they don't have a relationship with you in the current form in the future, right? That could be the right answer a lot of times. But I think it's because my during the day, and you you can attest to or deny this, right? I think I'm kind of difficult. Right. There's a speed, there's a I'm not a big please and thank you. I'm not a I'm much more like, hey, this needs to get done, let's go, type of person, right? I'm just like so focused on like getting shit done that I think, and I don't know how to stop that. I just have like so much. There's so much I want to accomplish, there's so much I want people to accomplish. It's just like there's not enough hours in the day. So I just I think I behave a certain way where I don't take a breath, like all it's a sprint all day, right? And so I think this is my breather before the sprint of the day. And that I think that's how I because otherwise I don't know that I would make time during the day to think about this context. I'm just too in it, right? It's game day. Every day is game day. It's just really hard for me to like carve out and think about the the human context.

SPEAKER_00: 46:20

I think a lot, I think a lot about like the actual work day. So it's supposed to call it nine to five. And most people are on a manager schedule, which is what you're referring to. Like the manager schedule is like we're going, we're you know, we're we're pushing the ball, we're pushing the ball forward in all capacities, and there's one speed to do that, right? It's like very hard to slow down when you're in that mindset. And you think about that manager interacting with an engineer and what's commonly labeled as a maker that requires a lot of deep thinking, uninterrupted, long, you know, long task sort of work. And if the if the if the manager goes in, you know, goes in and is trying to relate and and you know and manage the the maker, there's always friction because that person's in a completely different state.

unknown: 47:11

Yep.

SPEAKER_00: 47:11

They don't want to be disrupted. They're trying to get their that their work done is in is in solitude in a lot of cases, right? And so you have this like this constant tension, you know, between the maker and the manager. And I think that knowing that you're in in manager mode from nine to five, like to me, like whenever I've thought about that, it gives you permission to kind of not be the perfect perfect leader. Like the goal, the goal is pushing the ball forward. And as long as your team is aware of that, like they're they you know, they shouldn't be upset that you're you're pinging them for questions. But it's like it to me, it gives you permission to embrace embrace the role because that is the role that you're playing as a leader of the company.

SPEAKER_01: 47:51

Yeah, and I and I really do try to limit my engagement to really try to limit my engagement to Slack. And then I let everybody know, hey, by the way, please be sure to put your Slack on snooze or pause if you're in deep work mode, especially like the software engineers, right? Yeah, if you're in deep work mode, just tighten it up, right? Uh and put it on pause. So I think from that perspective, yeah. I mean, I I think like the work environment also, I think it's very difficult, you know. I I think by default, you know, there's all this narrative around manager versus leader. And I always kind of say I'm I don't think I'm graded either, quite honestly. But I do think I am very mission-oriented, like it's very personal, like the mission is very personal, yeah. And I think for folks that are have maybe bought into the mission, but the mission's not in their bones yet, I can be difficult, right? They're like, why is he obsessing about this thing? Like, why is he you know, oh my god, like, did I do something, you know? And of course, you know, the first inclination, I feel like, which is really bizarre in many ways, is people quickly first their first move is what did I do wrong? 100%. If he's asking me about this, like what did I miss? What did I do wrong? And you know, there's someone on my team that I've talked to a lot about this. I'm like, dude, like I'm just in it. Like, I am just in it. I'm I'm like popping into I found this GitHub reposit repo that I'm like, you know, like I'm just in it. And like just because I'm doing things that maybe feel like are your swim lane, like it doesn't mean anything. It doesn't mean like I'm in your swim lane because you're not swimming.

SPEAKER_00: 49:55

Yeah, you're the you're in many cases just genuinely asking to get to to to know. Like you're asking the question, like it's not a rhetorical question. Like you're actually asking to get to gather information, not to, you know, be a jerk micromanager, right?

SPEAKER_01: 50:09

Right.

SPEAKER_00: 50:09

It's like, hey, here's the link. Yeah, it takes. I mean, I remember when I first started, like I, you know, our our relationship at work has changed a lot because you know, I started at Shadow as an employee. You were my employer, and you know, now we're now we're partners. And I think that it's a lot easier for me to digest a message from you late that's that feels like a targeted question as a partner than an employee, because as an employee, you're like hair, you know, your hair's on fire, you're like, Am I in trouble? You're wrong. Yeah, am I gonna get fired?

unknown: 50:41

Yeah.

SPEAKER_00: 50:41

That's just the instinct, right? Anyone who's like worked as, you know, with that sort of hierarchy dynamic, like you're fearful. But when you once you're established as like, hey, no, I'm a co-owner in this thing, we're working on these things together, it becomes much easier to I think understand that relationship. So it's like, how long is that learning curve for someone that joins and works with you to understand that like you want them to be a co-owner in in the thing that you're working on? And if they view, if they view you that way, they're not gonna feel threatened.

SPEAKER_01: 51:12

Yeah, it's funny. We've been going through, we've been interviewing some people, and I've been doing a lot of the first interviews. And they always say, like, well, I'm interviewing my first interviews with the CEO. Like, is there anyone else I'm gonna interview with? You know, like usually you work the other way. I'm like, no, like I'm gonna spend 15 or 30 minutes with you first, and then we'll like, and so the they're like, you do it backwards. I'm like, well, here's the thing I might decide that I want to hire you, and that's fantastic. However, after you meet my team, you may decide you don't want to work for me. And I've just found that instead of you spending a bunch of time, like, like, you know, we'll flip it around a little bit. It's been really fascinating, right? People are like, what? And I'm like, yeah, like there's a certain amount of crazy around here, and I don't know that I can describe it well as the people that have to live with me and in my crazy.

SPEAKER_00: 52:12

But it's best, best we meet and have this conversation up front, right? That's funny.

SPEAKER_01: 52:18

It's like if I slack you at two in the morning, it does not mean you have to respond. And it's not a test. I swear it's not a test.

SPEAKER_00: 52:28

Okay, last question in the lightning round. What at this phase in your career, when you look five to ten years out, what what do you want? What do you want? What do you, you know, not necessarily what are your goals, but like what what is a successful outcome for you? Like what makes you both both both happy and and satisfied when you get to when you get to the end of your career.

SPEAKER_01: 52:58

Yeah, I mean I think it it sounds maybe sappy, but I think it's community, right? I think a lot of how I think about our next fund and our next fund and our next incubation and our next whatever, right? Has always been, I think I said at one of the shadow summits was hopefully at some point the next fund that we do, all of our LPs will be our founders. Right? That would be the most ideal situation, right? Like a bunch of our founders have exits, and like, hey, like I want to be part of the next fund, right? And I think I think now more than ever, that's really it's kind of interesting. You know, I I think like I've always had like a business community, a lot less of a social community. But since I've moved to Half Moon Bay, it's been super interesting, man. Like, I mean, I didn't realize how much I thrive in being part of a community, but like, you know, the local coffee guy, like he'd I'll go get a coffee and he'll like walk me back to my office to ask me questions about different things he's thinking about, different strategies and stuff like that. And I'm super helpful, you know, try to be helpful to him, or the local restaurant guy. I mean, it's just like so interesting that I didn't I've never really had like that personal community. It's always been like work, right? All my AC friends, all my VC friends, it's always been like a work thing. So this in-person kind of social community, the parents and all that, you know, you can't help it around here. You go to the grocery store, you will run into someone you know. We've only been here for a year, it's just small. Yeah, it's just very small, and everybody knows everything.

SPEAKER_00: 54:40

So building building a strong community is the number one indicator of I hey, I spent the last 10 years in a good way.

SPEAKER_01: 54:53

100%.

SPEAKER_00: 54:54

I mean, it's not money.

SPEAKER_01: 54:56

It's not, you know. I'm not like, oh, I need to have three private checks, like no. I think I think it is. I think the the key indicator because I and I think it's even more than ever. I mean, maybe it's always been that way, but I feel like more than ever, like you know it's all it's all like I always say like I'm trying to build the the ligaments and tendons of building a community, right? Trying to make this stuff work and yeah.

SPEAKER_00: 55:26

Well, that's fun.

SPEAKER_01: 55:27

All right, man. Thanks for that. All right, I'll see you next week. Happy birthday. See ya.