Episode 03 - The Founder Mentality: Risk, Growth, and Building Ventures with Paul Capriolo

Episode Description

In this episode of Entrepreneur in Residence (EIR) Live, Ilya Tabakh and Terrance Orr sit down with Paul Capriolo, a venture principal at Portfolio T, to explore his journey from building successful companies to becoming a Venture Studio leader. Paul delves into his experiences in various industries, discusses the founder mentality, and shares his unique approach to risk reduction in startups. The conversation touches on the importance of self-growth, the role of venture studios in shaping entrepreneurs, and how AI is revolutionizing venture building. For aspiring EIRs, seasoned entrepreneurs, and startup enthusiasts alike, this episode offers valuable insights into the evolving landscape of entrepreneurship.

Key Points from This Episode:

• Introduction of Paul Capriolo and his background in computer science and entrepreneurship. [00:04:12]
• Transitioning from social gaming and advertising to being a Venture Studio leader. [00:06:16]
• The role of vulnerability in building trust with founding teams and the challenges of advising versus leading a venture. [00:08:01]
• Exploring the difference between technical founders and broader business challenges in early ventures. [00:11:17]
• Challenges faced while working with founding teams, including identifying assumptions and risks. [00:11:56]
• The concept of startups as “risk reduction factories” and how to prioritize risks in venture building. [00:18:45]
• Paul’s “risk-weighted venture building” approach and the importance of running at risks rather than avoiding them. [00:20:16]
• The significance of mission-driven entrepreneurship and aligning teams with a clear vision. [00:24:02]
• Transition from reactive to proactive decision-making and defining priorities in startup leadership. [00:26:19]
• Paul's role as an EIR at the University of Maryland and how it contrasts with his work at a Venture Studio. [00:27:48]
•  Insights on the codified methodology of venture building and knowing when to deviate from the playbook. [00:37:15]
•  Why the zero-to-one phase of venture building excites Paul more than scaling mature companies. [00:41:42]
•  The role of AI in accelerating venture building and the possibility of creating billion-dollar companies with minimal teams. [00:47:24]
• The importance of meditation and mindfulness in entrepreneurship for long-term success. [00:52:10]

Links:

• Paul Capriolo
• Portfolio T
• Terrence Orr
• Ilya Tabakh
• EIR Live

• (00:00) - EIR Live Show Intro
• (01:11) - Co-host Preview
• (04:12) - Paul's Background
• (06:16) - From Gaming to Ventures
• (08:01) - Building Trust & Leadership
• (11:17) - Technical vs. Business Challenges
• (11:56) - Working with Founders
• (18:45) - Startups as Risk Reduction Factories
• (20:16) - Risk-Weighted Ventures
• (24:02) - Mission-Driven Teams
• (26:19) - Reactive vs. Proactive Leadership
• (27:48) - University EIR Role
• (37:15) - Venture Building Playbook
• (41:42) - Zero-to-One Phase
• (47:24) - AI in Venture Building
• (52:10) - Meditation for Success
• (59:13) - EIR Live Show Outro

Creators & Guests

Host

Ilya Tabakh

Founder | Scaling #ClimateTech as Entrepreneur-in-Residence @Black_Veatch | Author | Based in #KansasCity | work = people+systems+tech (at least 2 of the 3)

Host

Terrance Orr

I’m just a guy from a small town with big dreams | Venture Builder, Investor, and Advisor

Guest

Paul Capriolo

Paul Capriolo is a venture builder with a computer science background from the University of Maryland and Carnegie Mellon. After founding successful companies in social gaming and advertising, he now serves as a venture principal at Portfolio T, helping deep tech startups move from zero to one. For nearly a decade, he has also been an Entrepreneur in Residence at the University of Maryland, mentoring students and alumni. Based in Lewes, Delaware, Paul specializes in risk-weighted venture building and has worked on diverse projects from food science to gene therapy. He is particularly passionate about integrating AI into the venture building process.

What is EIR Live?

EIR Live brings you invaluable lessons straight from Entrepreneurs in Residence (EIRs) who have been in the trenches. Hosted by seasoned EIRs Terrance Orr and Ilya Tabakh, each episode offers actionable insights and real-world strategies as guests share their personal journeys, successes, and hard-earned lessons. Whether you're an aspiring entrepreneur in residence, venture builder, or innovation leader, you'll gain practical knowledge from those actively shaping industries. Tune in to learn directly from the experts and empower your own entrepreneurial journey.

Ilya Tabakh: 00:02

Welcome to EIR Live, the podcast where the entrepreneurial spirit shines through stories and insights from entrepreneurs in residence from across the ecosystem. I'm your host, Ilya Tabakh, joined by my co host, Terrance Orr. Each episode, we dive into the unique journeys of innovators and disruptors, from the first sparks of inspiration to the challenges and triumphs along the way. This podcast is for the self starters, for venture creators, for the translators who can connect the dots. Whether you're aspiring to be an EIR, have been in the game for a while, or work with an EIR, EIR Live offers you a front row seat to the highs and lows of the innovation journey.

Ilya Tabakh: 00:42

Our conversations are filled with actionable advice, deep dives into stories of EIRs that are redefining the role, and live q and a sessions, all designed to engage, inform, and inspire. Tune in, join the conversation, and let's explore what it takes to turn ideas into reality, and connect your expertise to accelerate organizations who aspire to build the future. Welcome to EIR Live, where entrepreneurs speak, we listen, and communities grow.

Terrance Orr: 01:11

Man, that was an incredible episode with Paul. Just a ton of knowledge that he shared. I mean, everything from, you know, looking at a startup, you know, as a risk reduction factory, how you manage those risks and how you prioritize them. Thinking about the future of company building and how AI is gonna play a role in that. Being a comp sci major and graduate, getting his first exit out of college when he didn't know much as an entrepreneur, all the things that people experience in in this journey, but from a different lens.

Terrance Orr: 01:43

And really, for me, the highlight of the episode was hearing Paul talk about impacting others, through his role as entrepreneur in residence at the University of Maryland. And that's why he's been doing it now for nearly a decade and landing his opportunity, at a venture studio, not even knowing that he could. And he raised his hand to do it. And I just think there's something very, very impactful about that. And lastly, I'll save that for the guests actually to listen to.

Terrance Orr: 02:10

And I'm gonna pass it over to you because there's something else impactful that he said, but I but I want them to listen to the episode to get it.

Ilya Tabakh: 02:16

What what was cool to me about it is, he said a lot of impactful things. We got a just a great opportunity to dig in a lot of topics that I think are important and in some cases, maybe aren't as emphasized as it should be. But I think for me, Paul opened up pretty early with project into the world what you wanted to be, and I think he's a great example of somebody living the things that he preaches. And I think that that is too rare in the world that we live in today. So it's exciting to see folks be well principled and know why they're doing the things that they're doing.

Ilya Tabakh: 02:47

So I'm excited to hop into this one.

Terrance Orr: 02:49

Looking forward to hopping in. Let's do it. Paul, I'm incredibly excited today to have you on the podcast. Ilya and I, we've been looking forward to, you know, getting you on the podcast. We are glad you said yes.

Terrance Orr: 03:05

Thank you. We, we appreciate your time today.

Paul Capriolo: 03:08

Glad to do it.

Terrance Orr: 03:09

And I've gotten the privilege to know Paul, over the last few years and some of the work he's, he's been doing, inside of, you know, the venture studio that he's supporting right now. And, you know, I was, felt very privileged to do a project with Paul, and a venture with him, when he first got into the studio and learned way more from him than he would have ever learned from me. So, I feel honored to have him on the podcast today to talk about something that I'm very passionate about, something that Ilya is very passionate about and that's, you know, entrepreneur led and built companies and finding people who've been in residence in an organization, whatever that organization might be, and to talk about their journey, their background, the war stories, and things that make them battle tested, right, in this world and in this mysterious role that we call an entrepreneur in residence. But enough enough about those things, Paul, I would never be able to do your background justice. So I love it if you can kick it off and introduce yourself to the audience, please.

Paul Capriolo: 04:12

Totally. Terrance and Ilya, thanks for having me. This is a super fun opportunity, and I love talking entrepreneurship. So a little bit about me, I live in Lewis, Delaware. It's called Slower Lower Delaware.

Paul Capriolo: 04:24

I have 4 kids and a golden retriever, live by the beach. It's awesome. It swells during the summer, and it has quiet off seasons. And, you know, personally, self growth is my north star. So everything I do, I think, starts with me, and I project who I am to the world.

Paul Capriolo: 04:41

So and and I especially saw that once I started having kids, just the a reflection of yourself and an opportunity to accelerate your self growth. My background is in computer science. I went to Maryland undergrad in Carnegie Mellon for my masters. And I caught the entrepreneurship bug from really the beginning of my life. So starting businesses as early as grade school and then started my first formal company in grad school with a couple of computer science friends and really never looked back.

Paul Capriolo: 05:08

So I think what attracted me to entrepreneurship was the ability to bet on myself and control my own destiny and maximize the value that I could create and and really just make sure that I was doing what I loved. And, the first company I started, I had we had no business background. We didn't know what the heck we were doing. We just wanted to build cool products that we thought, you know, people would like. And we quickly got punched in the face, you know, a lot there.

Paul Capriolo: 05:36

And then, you know, through failures and learnings and lessons, I've gone on to just to start 2 successful companies, 1 in the the gaming space, the social gaming space, and 1 in the advertising space. And since then, I've joined my friend's company as a director of growth at an ecommerce SaaS company. I was there for 4 years running marketing and sales and customer success and and support and things like that. And most recently, for the last 2 years, I've been a venture principal at Portfolio T. It's a super fun job at at a venture studio where I get to work with generally, like, really deep tech startups to help take them from 0 to 1.

Paul Capriolo: 06:16

So it's me and a small team of folks that generally act as cofounders to maybe a small venture team of a CEO and a couple other, founders. And we help them find the problem and the pain and the solution that solves the that pain and ultimately help define the business around, around the solution. And I've got I've I've had the privilege to work on ventures from food science, which I worked on with you, Terrance. Super fun. And, I learned a lot from you as well.

Paul Capriolo: 06:46

Thank you. And, satellite based earth earth observation, blockchain KYC, and most recently, just wrapping up a gene therapy venture. So my first foray into nanomedicine. So I I love I love that 0 to 1, and I I really love maximizing the value I can create, for these ventures, and and that's the sandbox I love to play in.

Terrance Orr: 07:07

Thank you so much, Paul, for for introducing yourself because, you know, this guy is really good at 0 to 1, guys. You know? I and and he's really good at motivating teams, and, he's not an a hole while he's doing it. He's also, you know, I think that's important for somebody to be able to motivate teams or not, you know, can also, you know, motivate people and be a good human at the same time. And Paul, I think you exemplify that, you know, better than a lot of people that I know.

Terrance Orr: 07:30

And, Ilya, anything that you you wanted to follow-up on on his background?

Ilya Tabakh: 07:33

Yeah. No. Absolutely. I mean, I I I always am fascinated by, you know, kinda the difference between actually leading the venture versus sort of helping others. I'm curious if you can kinda talk through the difference, on kind of sitting next to a founding team and kinda working with them as as opposed to being kinda proper founder.

Ilya Tabakh: 07:54

Is it is it is it that different, or is it, pretty similar? Or how what's kind of been your experience? It depends, obviously.

Paul Capriolo: 08:01

But what it really depends on is is the founders that you get to work with. And some founders, they they, you know, they trust you. You can build trust. You can build a great relationship. They're looking for advice.

Paul Capriolo: 08:12

And and, really, you do feel like a founder. Others try and keep you at arm's length. They have a a challenge kind of bringing bringing you in to to the inner circle and just like you're an unknown quantity. And and then I think it can be a challenge to help them see, you know, your side and and what you think the right actions are. But ultimately, it comes down to, like, can you get on the same side of the table as them or not?

Paul Capriolo: 08:37

And if if I don't have conviction in what I'm working on, then and I can't articulate it properly or where I think the the venture should go, then maybe I shouldn't be on that same side of the table. So if the founders push back, the more they push back, then the more challenge it is and the more opportunity it is for me to clarify my thinking. And, ultimately, I'd say do even better by them sometimes.

Ilya Tabakh: 09:00

Yeah. No. Absolutely. I mean, it's it's, you know, sort of that role as an EIR in a corporate setting. I'm kinda more of a spiritual leader than kind of the hard line leader.

Ilya Tabakh: 09:11

And so that's that's taken a little bit of a kinda different approach. And, you know, it's, I'm very much like you where I like if things are going on, I like to jump in in the trenches, really sort of understand what we're doing, and then kinda figure out how I can kinda help carry some water. And it's just it's interesting to sort of see as you kinda play different, types of EIR roles, how how that kind of evolves over time. So I appreciate kind of the that that insight there.

Paul Capriolo: 09:38

Yeah. And and and you mentioned spirituality. Like, that being being open and being vulnerable and connecting with these founders on a deep level, like, underneath the business, like, who who they are and, like, why are they even building this business? Of all the things that they could be doing with their time and their lives and their their careers. Like, why are they here?

Paul Capriolo: 09:55

And and how can you get passionate about that problem too? Right? And and the more you commit to them, the more that they commit to you.

Terrance Orr: 10:04

It's interesting because naturally, I wanna ask you about, you know, some some challenges that you face in in working with those founding teams. Right? Usually we see, you know, there's always an an issue or something, right? Sometimes on the ground floor of with a founding team or with a new venture team or with the folks that you you're just sort of doing this tango. You're getting to know each other and building building this new company.

Terrance Orr: 10:27

And eventually, you you you run or you don't run and you figure out, you know, different things. Could you could you talk a little bit about some of the challenges that you've experienced as an EIR working within the Venture Studio, you know, helping to take these things from 0 to 1, but knowing that there's gonna be a founding team that will eventually come along the journey for you, and and take it to the next level while you go off and build the next great company. Can Can you talk about some of the challenges that that you face in doing

Paul Capriolo: 10:54

that? Yeah. The question highlights the need to not just help them answer the questions, but help them build the muscles where they can answer the questions in the future, right, that haven't come up yet. And I think the biggest one of the biggest challenges is helping founders understand that their assumptions and their knowledge, unless they've they had the the proof that it it's a risk. It's a risk to their business.

Paul Capriolo: 11:17

And a lot of a lot of founders can be very confident in, their their understanding of the market and the customer and and the product. And and that's how I was when I started founding companies too. It's it's very customer research, customer development light, and just conviction focused. And I see that with a lot of first time founders, especially if they're coming if they're building something in an industry they have experience with. So the first muscle to build that is important for the entirety of the venture is being close to the customer and understanding and being able to intellectually understand what's what's an assumption versus what do I have conviction about and and and data to support.

Paul Capriolo: 11:56

So that is probably the big first tension point. And then there's this there's this, kind of initial period with ventures where I'm onboarding with the team, and we need to really understand the company, understand the the market, understand, the the space, the domain. And the founders needs to be to be willing to explain things and let us challenge them. And normally, they're not getting challenged at this really deep level. Right?

Paul Capriolo: 12:23

Like, imagine, like, a 10 hour open ended interview where you're just like, you're at some point, you're getting so deep and you're asking questions that no one's ever asked. And some of the times they can be uncomfortable, even though you try and frame them in really gentle ways. But it's like, they have to be okay with you poking holes in their business. And, and then that's an opportunity to say, okay. Well, this might be a risk.

Paul Capriolo: 12:44

This might be something we need to work on. But they need to be willing to engage and be vulnerable enough to to indulge in those conversations. Sometimes you get folks like, why do you need to know this? Like, there's someone else on the team is working on that. Like, let's just focus on let's let's try and put you in a box as a venture builder or venture team.

Paul Capriolo: 13:00

When really, especially at the early stages, you need to be able to look across the ecosystem, look across the company and the functions, and and that's how you add the most value. So they need to be willing and able to articulate really everything about their business. So those are probably the the two biggest challenges that, that will create value for them far beyond my engagement with the venture.

Ilya Tabakh: 13:21

Just to quickly double click on that. I work with a lot of climate tech founders, and so a lot of them have, you know, sort of deep technical backgrounds. And I found, you know, as as a trained engineer myself that typically kind of engineers or other technical, folks, tend to kinda have high confidence and and in many cases, have spent, you know, a nontrivial part of their career kinda being the expert. And I think, actually, your two points are pretty well related to each other. It's like being close to the customer and then also sort of being open and sort of continuing to have a living model of what you're doing end to end is really sort of almost an indication of, you know, are they interested in what reality is telling them about the thing that they're working on?

Ilya Tabakh: 14:08

Right? And and whether that's directly from the clients or, you know, sort of, business model and everything else, that that humility thing. And, especially, like, thinking about who who on the team is providing kind of different types of insights are are kind of some things that I found. But that just like when you were talking about, you know, openness to what clients are saying and then sort of letting go a little bit of your expert status or at least backing it up with very deep evidences is really important. I found that in in kind of my work as well.

Paul Capriolo: 14:40

I'm glad you brought up technical founders because they're one of the other challenges with with technical founders is sometimes they wanna put themselves in just like the tech sandbox. Right? Like, I I do the tech. Like, you go do the customer discovery. I'll build it, or I'll do, you know and and that's not really the founder mentality, especially if they're coming out of, like, academia.

Paul Capriolo: 14:59

Like, I work with a lot of PhDs, and and sometimes they just wanna you know, I wanna stick to the science. I wanna stick to the the tech or the AI or whatever it is. And things like customer discovery, things like financial modeling or putting together a a pitch, raising money, like, these are so foreign and uncomfortable at first that you you wanna try and keep them from retreating and and pull them in, and and that's that's gonna just pay so much dividends for them if you can get them to open up to these other these other functions that are just incredibly valuable and and critical to the business's success.

Terrance Orr: 15:31

I just wanna add on to to a few things that you and Ilya said because there's a few different things that I like to pull out these little themes sometimes fall. So you'll see me do that throughout our our chat today. You mentioned the word risk. You you mentioned the words poking holes in in the business, and you mentioned the words founder mentality. Those things stick out to me a lot as you were explaining the different things because talk about I think there's something to be said about somebody come to the table with the credibility to be able to poke holes in a business.

Terrance Orr: 16:03

Right? Because you've had to, like, walk that journey in some capacity before to see something and to go, well, how would this work? How's that gonna work? How are you gonna do that? And and it comes from a place of war wounds that you've already felt, you know, and landmines that you've already stepped on, and you're actually trying to help the founder avoid those landmines by asking the questions to get them to think about it far in advance before they get an investor across the table from them.

Terrance Orr: 16:29

Right? That's gonna actually ask those same questions. The other thing that you brought up was risk. Right? And effectively, you know, I look at startups as as a risk management exercise, right, in a risk reduction factory, if you can if you can go about it that way.

Terrance Orr: 16:43

And but lastly, I want you to touch on the thing that you talked about last, which is the founder mentality. What would Paul describe as the founder mentality?

Paul Capriolo: 16:51

I would say the the founder mentality is the embodiment of the entrepreneurial spirit. And what I mean by that is that someone an entrepreneur is passionate, and they believe in they're mission driven, and they believe in that they have a unique opportunity to make an impact on on the world that creates a change that they wanna see in the world. And I think really it's that's why entrepreneurs are admired in our society is because they're willing to take a risk on something that they believe in at the expense of their time and their talent and their treasure. And, yeah, there's an upside and people really admire, if you look at, like, all the entrepreneurs in the world, I'd say the ones that are most admired are the ones that are are most mission driven That can say, like, I'm doing this because I wanna see this change in the world. And you can agree with that change or not as as a consumer or an individual, and you can vote with your dollars.

Paul Capriolo: 17:46

But ultimately, if you can if you can be mission driven and bet on yourself, like, that's that's what I think it's all about.

Terrance Orr: 17:53

Fair enough.

Paul Capriolo: 17:55

I do wanna talk about risk, though, because that's that's

Terrance Orr: 17:58

that's something that's been on my

Paul Capriolo: 17:59

mind a lot lately.

Terrance Orr: 18:00

Oh, absolutely. Because I I know you're you're you're you're working on something potentially that that may be too early to talk about. But, you know, if you wanna talk about, you know, sort of, the things you're working on around risk and and and assessing risk and building.

Paul Capriolo: 18:14

Just because you mentioned, that startups are risk reduction factories, and I I strongly believe that. And I I strongly believe that entrepreneurs are not really risk takers. They're risk reducers. And, Peter Drucker has a quote that says something like all profit is derived from risk. So the way I've been thinking about venture building really at any stage, at least at the earliest stages of venture is it's truly just an exercise in prioritizing risk.

Paul Capriolo: 18:45

And there's all these, there's all these methodologies that exist. And we use one at our venture studio and every venture studio has kind of their own and every, you know, there's lean startup and there's all these things. Right? And I think they all do a pretty good job at approximating risk. There's, you know, like, what problem are you solving?

Paul Capriolo: 19:03

Who, you know, who matters most? What matters most? What's the business? Like, these are all really important questions that approximate a risk, but it's not always true that every venture needs to follow the same linear kind of risk derisking process. Right?

Paul Capriolo: 19:20

It might be that maybe the the the demand is obvious or more obvious, or you have more conviction about it. So really it's, can I adhere to a certain regulation or is this tech even possible? Is it right? Is it even possible to to build and create? Can I access the data I need?

Paul Capriolo: 19:35

So I've tried to simplify how I think about venture building and methodology into just a very simple heuristic of how can we identify and prioritize the top risks for the venture, and then how can we take each risk and creatively come up with the lightest touch way to derisk or create learnings that will help us understand the risk better, potentially derisk it, potentially create find out there there's more risks under the surface that we weren't aware of. And really, that's, I think, the the simplest form of venture building methodology that I've been working on. I'm working on I call it risk weighted venture building. It's probably not a new concept. A lot of people do this.

Paul Capriolo: 20:16

And even we do, like, risk and assumptions workshops here, but not till later in the venture. Now I I I think that this should be, 1st and foremost, where ventures start is what are the biggest risks. If you focus on on that, then the the goal of your actions becomes, how can you maximally address the risk with the minimum resources? And then if if that's if that's true, then what a great venture builder is, is someone that both can identify and prioritize risks and also creatively come up with ways to de risk them and then take actions. When I started and a lot of the the entrepreneurs that I mentor, they they like to hide or run from risk.

Paul Capriolo: 20:57

You know, it's like especially the technical ones, back to what Ilya was talking about earlier. You know, they wanna they wanna, like, build their thing, and they don't wanna talk to anyone. They don't want anyone to say that their baby's ugly. But running at the risk is probably the most valuable. It's I'm I strongly believe actually is is the most valuable thing that you can do as a venture builder.

Paul Capriolo: 21:15

And the more that within you like, something within you says, like, avoid this or hide from this or do work on something else like that that, like, inner critic, the stronger it means that you need to run at it. Right? You need to say, okay. Well, why am I nervous about this? There's something that, like, within me that is an assumption where I'm actually not confident about this even though, you know, my picture, my projection is is otherwise.

Paul Capriolo: 21:42

And that is a fantastic heuristic as to what you should be working on as a venture builder.

Ilya Tabakh: 21:46

You know, if I had any advice for my past self, that probably would be in in the very short list of, you know, if something's making you nervous or, you know, is you the it's kinda your gut's telling you something's wrong here. That's the thing that should be prioritized. That that took a while, and I'm glad, you know, it's it's awesome to hear, you know, other folks have made that realization as well. I guess if you had kind of other you know, you've had quite a varied experience at this point from kinda different perspectives. What other kind of advice would you, you know, if you had the poll time machine, would you go, kinda give to a a younger poll?

Ilya Tabakh: 22:23

And is there kinda, a couple things that you would share?

Paul Capriolo: 22:27

Maybe to not answer your question first. When I when I started, I was too naive to know, like, how hard it was. And I didn't have anything to lose other than my time for embedding on myself. So I was in a good a good spot. And also that naivete, like, really drove me.

Paul Capriolo: 22:41

I felt like I could do anything. And, certainly, I I found that wasn't true. But but I wouldn't I wouldn't tell my my prior self anything that would, I'd say, you know, not basically, like, extinguish that naivete, like, that overconfidence in myself. Like, that I think was the thing that allowed me to jump off the cliff into entrepreneurship. So so I would I would do anything to to retain that.

Paul Capriolo: 23:09

But a few a few things that I would change that I would tell myself is definitely 1, Ilya, that you mentioned is, like, run at the risks. And if something feels unsettling, like, listen to yourself, like, what are you nervous about and how can you address that first and foremost? Right? The more you don't wanna do it, the more it should be your priority. It's kinda how I'd simply phrase that.

Paul Capriolo: 23:29

Other things are just staying as close to the customer, like we like we mentioned. It's something that I shied away from early. I was a tech founder. I wanted to just code and build products and and apps and things and didn't wanna talk to customers because I said, oh, it's like me. Like, I I would like this so everyone else would like this.

Paul Capriolo: 23:45

I'm like everyone else. And and that's just I mean, coming out of my mouth now, it sounds ridiculous. You know? And and another thing that that I would definitely tell myself is be mission driven. And when I started, it was you know, I wanted to build things that were cool that that I thought could make money, but it was there was no mission.

Paul Capriolo: 24:02

There was no real, like, vision. There was no impact I wanted to make on the world. These were ventures in advertising and social gaming, which, you know, there's lots of opportunity there to create efficiencies and connect with tons of users and gamers and and help brands grow. But I didn't have, like, a a real mission behind it. I was doing it because it was I was opportunistic, and I wanted to build cool things and and make and make a big company.

Paul Capriolo: 24:28

You know, I wanted to be a a successful entrepreneur. But as I look back on it, you know, I would want to be really, like, focused top down. Like, what is my vision? What is my mission? What is the impact I wanna make on the world?

Paul Capriolo: 24:39

And then tell my tell my past self to align everyone I hire with that, like, mission to metrics that I think was pioneered by SpaceX. Like, I admire that very much. So So how does how can everyone in in the org understand how they are contributing to the mission and why their role is so important? As opposed to, you know, when I I was awful at hiring when I first started. And I would I would try and convince folks to come work for me.

Paul Capriolo: 25:06

Like, oh, it's fun. Like, there there's pizza and ping pong tables and whatever it is, like, the perks. Right? Oh, we don't you know, we we we really value work life balance. And and and ultimately, like, I I ended up hiring a lot of folks that really didn't wanna work hard and they didn't really believe in what we were doing.

Paul Capriolo: 25:21

And they were because I pitched it like that. Like, that was my fault. Right? And I didn't set the expectations and the culture properly. And over time, I said, hey, like, the the more I I frame this as a challenge, the more I'm gonna attract people that really want a challenge.

Paul Capriolo: 25:34

The more I'm gonna attract people that you know, the more I frame it as a mission, the more I'm gonna get people to align with the mission and and believe in the mission and and think about the mission and and operate at a higher level and build a great culture around the mission. So it's right. It's it's, like, it's it's it's really those those are some of the the big things. One other thing that comes to mind is I used to be very reactive. Like, always on email, always on Slack, like, responding in, like, a minute to someone, like, just always thinking that, like, activity translated to value in a sense where really I've completely shifted to be way more proactive where I'm thinking about what are the what are the most important things to work on or what are the biggest risks of the business, which are the most important things to work on ultimately.

Paul Capriolo: 26:19

And then filling in those reactive filling in the other time with the reactive stuff. So really, like, defining my day as opposed to letting everyone define my day for me.

Terrance Orr: 26:29

This is very interesting. I I like hearing you talk about this topic because I I can hear a boost of energy, coming as you talk about mission to metrics and being, mission driven. And and it and it speaks to sort of, you know, how how people wanna try to deploy that impact, that scale, right, in in whatever they're doing. And it it really also speaks to, you know, entrepreneurs and residents or builders in general. Paul talked a lot about he used the term venture builder earlier for for our listeners.

Terrance Orr: 26:57

Right? Some people will use venture builder, EIR, in different words, you know, interchangeably. So so you you will hear, you know, him referred to venture builder, EIR. But this is the point of the podcast for you to learn about this role, this terminology, and and the different things that matter. But let's talk about building things that matter, Paul, and how that drives you.

Terrance Orr: 27:17

So, you know you know, talk to me about I don't wanna layer questions, but talk to me about the first time you heard about this mysterious role of a entrepreneur in residence. I believe it's when you got your first opportunity at University of Maryland. And and then talk about how the next time you you had an opportunity that came up at the Venture Studio to become an entrepreneur in residence, how those roles were different based off of your residence. But talk about how you actually got the opportunities first, if if you wouldn't mind sharing that with the audience.

Paul Capriolo: 27:48

Yeah. Sure. As I as one of my ventures was becoming a success, I was invited to be an entrepreneur in residence at University of Maryland. And I've been there now for almost 10 years, advising students and alumni and faculty on their businesses. And and that could be, like, a 30 minute, like, drop in advising session on a Friday afternoon, or it could be doing a lecture, product market fit or financial modeling and and everything in between.

Paul Capriolo: 28:17

And it's great to build relationships with these entrepreneurs. And what I loved, I did it initially, and I still do it, to give back to up and coming entrepreneurs. And it felt like it was just the biggest way for me to make a positive impact. And right, you can donate to your alumni organizations and this and that. But I thought, you know, if I can spend 30 minutes with a new entrepreneur and help them avoid some of the mistakes that I made or help them think through problems that I didn't think through properly, I could save them years of their life.

Paul Capriolo: 28:50

I could save them 1,000,000 of dollars. Right? This is, like, in 30 minutes or an hour. Like, this is huge impact that I can make. And that's what really attracted me to it.

Paul Capriolo: 29:00

And then I just fell in love with the I fell in love with the impact, and and I could see the reflection of my impact in in the businesses that I was advising. And this and assuming that the students are passionate, they're not always as passionate. Not every entrepreneur is as passionate as as as the other. But the ones that really, like that were mission driven, that believed in in in what they were working on and and had a real, like, strong reason not to just, like, I wanna make some money. Those were the ones that I loved working with the most.

Paul Capriolo: 29:29

And because they wouldn't give up when it got hard. And they would, you know, they would smash through the wall or they'd find a workaround. And as I was winding down, getting to, like, how I got this this job at Portfolio T or this role. As I was winding down my, my role as a director of growth at, at my friend's, Y Combinator SaaS company, I was looking to continue being an EIR in academia. I actually didn't know that EIRs existed in the private setting.

Paul Capriolo: 30:01

So I was looking at you know, I started to reach out to these different schools. You know, MIT was hiring an EIR and others and say, okay, I I would love to do this more, you know, full time. And then I just started coming across these things called Venture Studios. And, and I was like, oh my goodness, I can do this, with with real resources, with entrepreneurs that are more mature, farther farther along that have, you know, bigger ideas than, say, like, a college student. They're kind of thinking more, like, locally and and within their sandbox.

Paul Capriolo: 30:34

And this is exactly what I wanna do. I get to focus on the 0 to 1. So I I reached out to to Portfolio t, and I said, like, hey. I'm I've been in the EIR. I love being in the EIR.

Paul Capriolo: 30:46

Like, how does it work at a venture studio? Like, what is and, and it like, one thing led to another. And that was about 2 years ago, and I've I've worked on 4 successful ventures, and and I'm now a a venture principal here. So it was it was really natural. What I well, the biggest differences to to your other question, Terrance, is I would say, you know, the methodology.

Paul Capriolo: 31:07

There's a there's a methodology. There's a process. It's just so much more professional. Right? There's real resources behind it.

Paul Capriolo: 31:15

There's a network, a network that you can tap in more easily too. You have more budget for tools and teams and things like that. In the academic setting, you know, it's it's just like a smaller game, candidly, with, you know, entrepreneurs that aren't as mature and, and resources that are more restricted, in in the academic setting. So it's just getting it's like the big leagues, in my opinion. So both are are super valuable and and critical, and I I love doing both.

Paul Capriolo: 31:45

I can never work on, for instance, like, a gene therapy startup in my EIR academic role or right? And but but now I get to. And, and just being able to, like, learn about new industries and and new technology, and new ecosystems that you can't learn through academia was was a has been a really a big joy in being at a venture studio.

Ilya Tabakh: 32:11

It's probably obvious to the 3 of us or or maybe not. But the this, you know, I I really strongly believe that EIRs need a sort of have had entrepreneurial experience. And then, also, through that entrepreneurial experience, they build a lot of sort of muscle memory and and recognition of different behaviors and things like that. And you just talked through, you know, a handful. You know, we can probably spend 25, 30 minutes highlighting why a lot of the things that you said were important, you know, kind of that mission driven part, you know, kind of being open and humble, as well as, you know, the fact that you had done a few ventures.

Ilya Tabakh: 32:49

You knew, you know, in your experience, what worked, what didn't work, had seen a bunch of deals. You know? And and I see a lot of, like, first time entrepreneurs and first time kind of folks that are doing something, not realize that the folks that they're working with, you know, have a whole kinda deep body of experience. And so when they say something and they're used to being the expert, you know, they're not used to sort of having a a a a really kind of strong, conversational partner to to to really dig into some of these topics with. So I just wanna kinda highlight that for, know, some of the folks that are listening in that, you know, when when you see and have been involved in a lot of different things, you know, the there there is some stories and some other things that that give you some added perspective.

Ilya Tabakh: 33:36

And, honestly, like, once you see enough deals, you sort of say, hey. Is this a fast moving thing? What's the market look like? Do they have the team? You know, there's all kinds of things where you're roughly sizing this up to see, does it, you know, is it a bread slice, a bread box, or a bread band kinda thing, and and have some experience.

Ilya Tabakh: 33:55

So I just really wanted to not not gloss over a lot of the stuff you were talking about there, Paul, because I think that that's the, you know, part of the reason why I really like to see experienced entrepreneurs going into entrepreneur in residence roles. And and partially because a lot of that kind of tacit knowledge, becomes really important. So thanks for letting me jump in there, Terrance, but I just wanted to kinda highlight that because I think it's really critical.

Terrance Orr: 34:19

Of course, man. You jump in whenever you want, my friend. The, the other thing that I wanna layer on top of exactly what Ilya just said was there's this trend that we see, and you'll see it with our guests, and our guests don't know each other yet. When they listen to each other podcast, they'll see this trend. This trend of entrepreneurs and residents raising their hand, you know, for for their their first or their second EIR role.

Terrance Orr: 34:43

Like, nobody reached out to to to to Paul for the 1 he he I I reached out to them. Right? And and and I said x, y, and z. We had another guest on the podcast, Paul, that said the exact same thing almost. Right?

Terrance Orr: 34:56

You know, that they that they saw this thing, and they they reached out and sort of it led to, right, an EIR gig. I think the other thing that I wanna highlight for people is that you could be a Paul. You could be an experienced entrepreneur and have built the company, have walked the path before. Right? You understand and have respect for the entrepreneurial journey and process and still not know that there's EIR roles in these sort of settings, right, and still not know that a venture studio exists.

Terrance Orr: 35:25

I was one of those people too. So I I just wanna make sure that folks know that every single day, right, I hear from serial entrepreneurs on on LinkedIn who don't have a clue what the EIR is or how to get their first EIR gig. They just know they want one for whatever reason. Right? And but it's still very foreign, even if you've done this before, right, in in multiple different ways.

Terrance Orr: 35:49

And I think the last thing that, I I wanna highlight that Paul said is he talked about the studio having a methodology. Right? This this process of company building. You know, before I actually joined sort of the venture studio world, right, and joined the venture builder, I I wasn't convinced yet that company building could be codified, right, and that there was actually a methodology where you can take companies from 0 to 1. And if you follow that and you you test the risk and you go after it and you test your assumptions and your hypotheses, that you could actually land on something that was valuable.

Terrance Orr: 36:24

Right? So a little bit more naive at the time. But when I got into the venture studio world, you learn very quickly that the playbook equals, you know, usually the outcomes, you know, sort of thing. But you have to know when it deviate away from the playbook. And and that's when, you know, the the journey of working in the Wow and doing this on your own prior to being in a venture studio or whatever your residence might be is incredibly valuable.

Terrance Orr: 36:49

Right? And you saw Paul try to sit up a little bit. He's like, know when to deviate, from the from that playbook. Mhmm. And and, Paul, Paul, it looks like you wanna comment a little bit on on knowing when to pivot and and getting away from the playbook.

Paul Capriolo: 37:02

Totally. You have to be able to hold these methodologies loosely. And it's not just about following a process. Like, anyone can follow a process. It's about understanding what parts of the process are important and when.

Paul Capriolo: 37:15

And say and understanding that your mileage may vary based on who what venture team you're working with, what the ecosystem or the industry is, how far along they are. There's all these these variables. And and that's why I kind of like to simplify it to, like, just re prioritized risk, like a risk weighted process, because then it's really it's it's it's such it's so high level that maybe it it is customer discovery that you should be doing. Maybe it's something in tech. Maybe it's understanding markets or regulations or doing competitive diligence.

Paul Capriolo: 37:47

And and it just allows you to hold these things really kind of loosely and and think high level. I think the hidden secret of venture building and venture studios is the methodology only gets you so far, and then it really becomes about the people. Working together, how do you work with the founders? How do you do you act as a cofounder? And that's something that I try and instill in in myself and the team and and even share with the ventures we work with.

Paul Capriolo: 38:09

Like, I am going to act as a cofounder, and I'm gonna be just as passionate about this as you are. And that's not part of the methodology. Right? It's like, you know, do your customer discovery, do your prototype testing and solution testing and storyboarding and things like that. Like, you need to be able to pick the right tool for the job, but you need to understand what the job is in order to pick the right tool.

Terrance Orr: 38:29

No. I I I think that's super critical.

Ilya Tabakh: 38:32

Yeah. Just just listening to the discussion. It's such a people sport, and they're so, like it's just, like, when people there's always this conversation for me when people ask what's it like being an entrepreneur. Right? And, you know, why doesn't everybody do it?

Ilya Tabakh: 38:51

Why do you wanna do it? You know, may may maybe there's a question in here as well, but just to kinda set it up a little bit. When an entrepreneur says, you know, that thing I was working on, we hit this issue, and that was, like, the hardest thing I ever had to do. You know? Like, when we're talking about it in, you know, a discussion like this, it's like, oh, that that seems like it was hard.

Ilya Tabakh: 39:08

You know? Maybe they had to work an extra 80 hours, you know, or whatever. And it's like, that's you know? I'm sure they learned really something interesting from that. To, like, the entrepreneur, it's like, you know, maybe I had to fire some people or maybe my, you know, biggest customer said that, hey.

Ilya Tabakh: 39:22

We gotta put a pause on, you know, kind of this transaction that's really important to your payroll or a lot of these other things. And so just like it it's really hard to effectively communicate for me kind of the people and what does it actually mean doing something new. Right? Like like, really new as as an entrepreneur. And so it's it's just interesting.

Ilya Tabakh: 39:44

You know, I hear little little facets of that as we're kinda talking through the I'm gonna be a cofounder. Because for a first time founder, they may not fully realize how hard it's about to get. Right? They may they may not know, like, what they've gotten themselves into, and you say, hey. I'm gonna be a cofounder.

Ilya Tabakh: 39:59

It's like, hey. Paul seems like a nice guy. He's gonna be really supportive. Right? But but then when the firefight really starts, they're they they didn't realize kind of the thing that you were signing up for.

Ilya Tabakh: 40:09

Jokes on them. You know, maybe the question that say again?

Paul Capriolo: 40:12

Joke's on them. Yeah. I know. They think I'm just gonna be

Ilya Tabakh: 40:15

a cheerleader? No. Yeah. Right. It's it's definitely a a story that keeps on giving.

Ilya Tabakh: 40:20

But I guess if if I had a question in there, you know, I get asked quite a bit why, you know, why be an EIR versus just do the entrepreneur thing? You know? And and and and since you made actually, all 3 of us have made the transition in our lives, I think it's kinda interesting to kinda talk about that a little bit, you know, kind of the difference between just the e versus the EIR. You know, kinda what are your thoughts there, Paul?

Paul Capriolo: 40:45

That's a a challenge for for me kind of constantly to to think through that question. I'm always keeping my ear to the ground, like, you know, is there something that I really wanna start? Is well, like, what is next for for me? And even when I joined this venture studio, kinda when I joined, it's like, hey. You know, when you go start your next thing, like, that's cool.

Paul Capriolo: 41:04

Like, we're we're gonna be here for for that period of time, and and that was really a supportive and incredible thing, to say. So, you know, I I think what I love about being in the EIR that isn't just the e, the entrepreneur, is that I get to work in a more specific sandbox, 0 to 1. There's parts of when companies get mature that I don't love. Like, there's a lot of actions that founders and CEOs and executives need to take that aren't don't really feel like you're pushing the business forward. You know, you're more like you're just like shuffling things around, dealing with people, issues, and it just like it gets it gets muddy.

Paul Capriolo: 41:42

And the most the mo the biggest the biggest value you can add or really another way to say it is, the biggest risks you can reduce are at the beginning of the venture. Right? Like, are we building something that anybody wants? Like, who who are we building it for? What are we building?

Paul Capriolo: 41:57

What's the market? What's the business? Like, these are these are such foundational questions. So you can make, in my opinion, you can make the biggest impact in a venture in the earliest stages of the venture versus, like, what feature should we build next? What market should we go after next?

Paul Capriolo: 42:12

Like, what color should the button be? Like, those are important questions at times, but, ultimately, I think a lot of the impact has already been made by then. So I get to just work in this kind of focused area of venture building, this more 0 to 1. And I get to work across industries and learn things I've never never never knew before, like, you know, satellite earth observation or food science and, or or nanomedicine. Like, I would never start a venture in any of these fields because I don't know them.

Paul Capriolo: 42:41

I I wouldn't even have an idea in the industry. Right? So it's it's just like a a completely new experience, a new type of learning, and you just get to to run at these, like, problems that you would never get to run as run at, if you were if you're doing it yourself. But, you know, to go back to what I was saying earlier, I'm I think EIRs are always thinking about, you know, being an entrepreneur again. And you never lose that that fire or that mindset.

Paul Capriolo: 43:10

And that's so important in venture building as an EIR too, to not lose that. But also it's, I guess, a risk in some sense to the venture studios that employ the EIRs, because they're always so entrepreneurial. Right. But I think that's, that's well understood in the industry.

Terrance Orr: 43:25

No. I think that's fair. I think that's that's that's really fair, Paul. And it's it's very interesting because, you know, this question of, do you take, an opportunity as a EIR in a venture studio versus doing it outside? You know, some some of the reasons why I I why I wanted to do it in a venture studio was that, you know, entrepreneurship is a team sport.

Terrance Orr: 43:46

Right? And I got a chance to learn from other EIRs as well, you know, in in the venture studio. And frankly, people who might be potentially my cofounders in the future some years down the road that I had the privilege to meet through the venture studio. And I don't know that, you know, we would have just ended up in the same place, in the same room at some point in our in our lives if we hadn't met through the through the Venture Studio. Right?

Terrance Orr: 44:09

And I think, you know, it's something to be said about, having a place or residence where entrepreneurs can hang out and tinker with new and create new ideas until they no longer wanna tinker no more in that residence. And then they wanna spin out and start their own thing. I think the the other thing is around translating of of experiences. Right? You talked about background in gaming.

Terrance Orr: 44:32

Right? You have a degree in CS. Right? You went to Carnegie Mellon for something around entertainment technology. Right?

Terrance Orr: 44:39

I mean, your background is so different. It didn't have anything to do with aerospace or space or working with CPG or food, you know, but somehow you adapt it. Right? And you translated lessons that you got from other areas into the venture studio even if it wasn't directly related, you know. And this is one of Ilya's favorite topics, so I still list under on this one, which is around, you know, tell us about how having those different experiences in different spaces, how that translated into your residence at the at the Venture Studio, and how you how you just brought some of those learnings and things in that maybe would have been foreign to you had you not done this in a while, prior to coming into the Venture Studio.

Paul Capriolo: 45:28

Happy to address that. And I I love that you said, Terrance, you get to work with other entrepreneurs. Being an entrepreneur can be very lonely. There's not a lot of folks to connect with, like maybe advisors and board members. Maybe there's other entrepreneur groups out there.

Paul Capriolo: 45:41

But when you get to work with other EIRs in a venture studio, you you learn so you teach each other so much so quickly. And just before I I dive into your your exact question, if I started a business today versus the last business I started, which was maybe like 5 or 6 years ago, I think I could do like a 10 x better job or give myself like a 100 x better chance of success because of all I've learned so much in the last 2 years. And I think partly, like, getting to your question, like, working across these industries helps you level up, helps you see things at a higher level as opposed to just being stuck in kind of your lane. And that is that's that's been completely instrumental.

Terrance Orr: 46:22

Oh, that's awesome. I'm I'm gonna hand it over to Ilya now because I can tell. He he has the look on his face that he has a question that he's gonna ask you as to

Ilya Tabakh: 46:30

You know, that's the thing I love about all these conversations is the, you know, first of all, shared experience. 2nd of all, you know, because you've seen so many different things, there's probably ideas and things like that. Maybe maybe a question that we both like to ask and, you know, has gotten us some pretty interesting responses Is now now that you've, you know, kind of played the EIR role in a couple different places, you know, you've had some opportunities to sort of be in in kinda different stops on the EIR journey, if you will. Where do you see kind of the role evolving, I guess, part 1? And then is there kind of a dream EIR role in there somewhere?

Ilya Tabakh: 47:12

Or at least what are the, you know, kind of facets of a dream EIR role, if you have one. That that's always kind of a fun fun one to kinda throw out there and see what people see.

Paul Capriolo: 47:24

I think there's a commonality between how I would address both of those things, which is AI. Like, it's something that I've been really passionate about. Like, where do I see the EIR role heading? It's basically, like, heavily involves AI. And, like, today, I use AI in in literally everything I do from, you know, what questions should I ask a customer based on what I wanna learn or how can I synthesize these interviews?

Paul Capriolo: 47:49

How can I build a stakeholder map or do competitive analysis or even, you know, help me with the talk track on this slide or, like, how do I convey the message better? It's just I it's always open. I always have, you know, chat GPT or whatever the right tool is, And it's it's helped me level up. So I can think more, again, more high level. And I can and I so I think the future of EIR is is really, like, as AI matures and this latest release from Chad or OpenAI is is wild.

Paul Capriolo: 48:17

It's like PhD level intelligence. If you can break down a venture into a prioritized set of risks, then you can create you can use AI to create, well, 1, help you define the risks, but 2, help you creatively understand how to address those risks. And then it can be a blend of humans and agents that are ultimately addressing those risks. Right? Agents can go off and do research.

Paul Capriolo: 48:40

You can communicate your learnings back to the agents. The agents can communicate their learnings back to you. And it can be I I think, you know, you need less people to do more and move faster. Like, I've never moved faster in venture building. Like, today, I use AI to do things that just like last year would have taken me a week to do.

Paul Capriolo: 48:57

I can do them in an hour. I mean, that's huge multiplier. Right? And especially in in these early stages of ventures where you're measuring things in minutes. Right?

Paul Capriolo: 49:06

Like, what did you do today? What did you do in the last 30 minutes? And then for my for me, like, the dream role to to get to the second part of the question is to be on the forefront of AI and within venture building and understand, like, how can we ultimately get as close to we can as, like, hey. Build the venture. Hey, AI.

Paul Capriolo: 49:24

Go build, like, a a great venture with this mission. Or, like, here's my mission. And and so, like, tell like, let's point together and and work as as, you know, human and and computer pair to execute on the mission. And then, personally, like, I like the idea of of getting really far without having to to spend a lot of time, you know, worrying about building the team and hiring and and a lot of the peripheral things. You know, Sam Sam Altman said something, like, a month or 2 ago that he thinks that there could be a $1,000,000,000 one person company, which is a a huge, like, b hag.

Paul Capriolo: 49:58

But, like, I I think that, you know, there's there's shades of truth in that. And I wanna be part of the group that's thinking through, like, how does that actually come to come to be realized? And what does venture building need to look like for that to even have a possibility of being true?

Ilya Tabakh: 50:15

So so we're we're nominating Paul as the first conductor of the agents, people, you know, symphony, as an EIR. I love it. I think that's a great and I've actually noticed myself that, you know, the way that I've explained, what I can do is I'm effectively a team of 20 or 30 when when I'm sort of going to prototype and think about some of these things now with with some of these tools and agents. And it's it's it's, you know, crazy. And and there's, you know, there's new things every day.

Ilya Tabakh: 50:48

I don't know if you guys have checked out, notebook l l m from Google, but they have this awesome feature that essentially creates, like, a deep dive podcast. So you can put, like, you know, really really big hairy report out there or or like your business plan, old school. You know? Let's say the business school at whatever said you need to write a business plan. You actually wrote a business plan, but you don't know how to explain it to anybody.

Ilya Tabakh: 51:13

You put it in this thing, click, the and it's crazy, like, you know, because because that's a whole different skill set. And and a lot of these things are available and knowing about, you know, when you need the timpani to play versus when it's French horn time, you know, to bastardize this analogy a little bit. It it's it's powerful. So I'm I'm completely completely on board with that that view, Paul.

Terrance Orr: 51:34

I wanna actually, you know, give the people a little bit more, Paul, because this is a this is a pretty fun question, for me to ask you, because I I've I've had the privilege to work with you before, but it doesn't mean I know everything about you. And, you know, one of the things that I'd love to, explore with you and the podcast today is for you to share something with us that we cannot find on your LinkedIn or on your resume, that people just wouldn't know about you. You know, what is one of those things that Paul is into that's just not on your LinkedIn, not on your resume, but you're it's your thing. You're into it.

Paul Capriolo: 52:10

The first thing that comes to mind is meditation.

Terrance Orr: 52:14

Okay. Yeah.

Paul Capriolo: 52:15

I don't know if this is the access that you are looking for.

Terrance Orr: 52:18

That works for me.

Paul Capriolo: 52:19

I think I mentioned earlier that, you know, self growth is is kind of my north star. And I feel like, you know, minute for minute, the the the way I've grown the most is is through meditation. And it and to put it, like, kind of simply the how we are within ourselves, you know, like the phrase, like, happiness starts with you and and these kind of other, you know, cliches. Like, however you hold yourself kinda within yourself is is what you project into the world. Right?

Paul Capriolo: 52:49

So the better that I can I can be, the more, calm and stable and and and loving and all these things within myself, that's going to ultimately be make me a better CEO and a better father and a better manager and a better friend and a better, you know, parent or child or or whatever? That's a a practice that that is is really important to my life and has really, I'd say, made me a much better entrepreneur than almost anything.

Terrance Orr: 53:17

That's incredible, man. I really appreciate you sharing that because I think oftentimes, you know, entrepreneurs would de prioritize their own sort of, you know, mental health and, you know, interreflection of, you know, the things that they're going through, for the sake of building a new company. Right? And, you know, when it's all said and done, you need to be healthy to build a new company. You need to be stable.

Terrance Orr: 53:41

Right? You need to be able to control all the pieces and, you know, being able to meditate. This is something you shared with me a long time ago, and now it's coming back to me. But, you know, I I I think that that's important. I think more founders going through coaching and those things are also equally, as as important because those things contribute towards you building a everlasting company, because people build companies, period.

Terrance Orr: 54:07

Right? And you need to be health healthy to be able to do that, in every regard. So I think it's a really important tip, to share with people.

Paul Capriolo: 54:15

I agree that a lot of entrepreneurs will, and I was too, like I didn't, I only worked on the business like a 100 hours a week when I started, it was like sleep, eat, and work on the business. And and once once you build once an entrepreneur, maybe this is just for me, like, sees the connection between, like, oh, well, like, healthy mind and healthy body actually helps the business. Once you see that connection, then it'd be then it's so much easier to to build a practice around it.

Ilya Tabakh: 54:41

I I think you actually talked about it earlier, Paul. It's the you know, you used to think of things as activity means outcome. Right? And and I think it's, like, 4 things like mindfulness as well as just, am I focusing on the right things? As well as am I able to be sort of in the moment to have the conversation I need to have?

Ilya Tabakh: 55:02

You know? At the end of the day, minimizing risk is important, but also startups happen through you know, you can, in hindsight, can normally go back and say, hey. There's 6 conversations, you know, or or or 10 moments in the history of the company that were really crucial. And and really thinking about what skills do you need to sort of be there and maximize that opportunity. I think, you know, from my experience, that's where I've kind of learned things like you gotta be in the right place.

Ilya Tabakh: 55:32

And if you're sort of burnt out, you're gonna burn your team out and all these other things is maybe some of those other latent things that we were talking about when you when you start saying, you know, that's those were some of the hardest things I worked on. So may maybe to just kinda draw that point a little bit more. You know? Because I because I think that we've already kinda talked about it, but it's just to put a finer finer point that it's not just about the amount of emails you're able to answer. It's can you sort of, you know, win at the the 6 or 10 or 15 things you really need to when it's time.

Paul Capriolo: 56:04

Really well said. And and, you know, as as a CEO or, you know, when you get frustrated, when things start to go wrong, if you wear that stuff on your sleeve, like that trickles down to everybody and you start to affect the culture and you start to and and folks lose their motivation or and and they they key off of you. Right? And right. It's and it's the same with, you know, in family life and and all walks of life, really.

Paul Capriolo: 56:27

So it it it's, like, starts with the man in the mirror.

Terrance Orr: 56:32

Fair enough. This has been awesome, man. I wish I could talk to you for another hour.

Paul Capriolo: 56:36

It's been a lot of fun.

Terrance Orr: 56:39

I I I am curious before we let you go, because you've been a great gift to us, and and our and our audience. What are you working on right now, and how can the EIR, network help you?

Paul Capriolo: 56:53

Well, I'm I'm doing a lot. So how can the EIR network help me? The I would say if any if this has peaked anyone's interest, whether it's risk weighted venture building or AI or you're you've got a company and and you're looking to have, you know, a mentorship conversation, and build a relationship with someone that's kinda been there before, reach out. Like, I'm I love I love meeting new entrepreneurs. I love making impact, and I'm always looking to collaborate with passionate folks and and especially if they're mission driven.

Paul Capriolo: 57:25

So if you if you found this interesting and you wanna continue the conversation with me, LinkedIn is the easiest place to find me, and then we can take it off offline from there.

Terrance Orr: 57:36

Yo. Yeah. Anything anything you wanna dive into before we let them go?

Ilya Tabakh: 57:40

No. I love it. I mean, the answer is yes, but we don't have enough time already

Terrance Orr: 57:44

to That's right.

Ilya Tabakh: 57:45

A few extra minutes. But yeah. I mean, just the for for me, you know, I hope we can kinda continue to have conversations like this, because, you know, we're kinda teasing out different parts of, you know, in in in this chat, generally, you know, we we we talked about what makes kind of an effective entrepreneur, period. Right? And then how can you sort of translate some of those insights to the in residence part?

Ilya Tabakh: 58:10

We didn't really pull apart the difference between academic and sort of venture studio so much, but that's a theme that we've been pulling on. And it's just awesome for, you know, I started as of, like, a entrepreneur at a corporate in January of 2020. And I'm like, I, you know, I I think I know what to do. But in conversations like this with other entrepreneurs, I just I'm really happy that we have a chance to, really connect and learn from each other. And and I'm just, you know, excited that, this journey where, you know, I connected with Terrance and he was already talking to folks.

Ilya Tabakh: 58:43

You know, Paul knows other EIRs, and I'm just excited to kinda connect the dots and then, you know, help help Paul with, some of the things that he's working on, and then just kinda continue to to give back and build that momentum. So lots of questions, but we'll have to leave it for next then.

Terrance Orr: 58:58

That's right. We'll leave you with some suspense. And, you know, who knows? Maybe we can get Paul back for a part 2 in the future.

Paul Capriolo: 59:03

That'll be a lot of fun. I love talking entrepreneurship. I could cheer your ear off all day. So happy to do it, and and thanks again for having me. This was a lot of fun.

Terrance Orr: 59:11

No. Thanks for joining us, man.

Terrance Orr: 59:13

Thanks for tuning in to this episode of EIR Live. We hope you found today's conversation enlightening and inspiring as we journey through the highs and lows of entrepreneurship with our incredible guests. Be sure to join us next time for more stories, strategies, and insights on the entrepreneurial front line. Subscribe on your favorite podcast platform on YouTube and share the inspiration with your network. Do you have a EIR in mind that'll make a great guest?

Terrance Orr: 59:38

Drop us a line. Engage with us and fellow listeners in the EIR live LinkedIn group and join the conversation. Plus, get your questions ready for our LinkedIn live sessions following future episodes. Your insights help us shape our journey. Let's co create and innovate together.

Terrance Orr: 59:55

Until then, let's keep innovating, striving, and exploring ways to make our mark on the world. I'm Terrance Orr alongside my co host, Ilya Tabakh, and we're signing off. Let's keep building, everyone.