Neal Bloom - Managing Partner at Interlock Capital

This is a show about facing fear, unlocking courage and taking action.

Courage isn't necessarily a daunting thing.

It's going to give you more purpose, it's going to give you more drive.

It feels like making a courageous decision is going to get you closer to who you aspire to be.

It's knowledge plus faith plus action equals courage.

And so it behooves an entrepreneur to get to know the investor, to say beyond the check, are you going to work for me when I'm sleeping? How much are you going to go to bat for me? Can you open doors or can you give me cheat codes on things?

You are about to enter the war zone. Be prepared for pain. This is a direct quote, Neil, that I'm pulling off of. I'm going to protect the somewhat innocent, but an entrepreneur who raised money for the first time and was talking about what it's like to show up at the table and the table is that table. And it can be scary for a lot of people. And I'll acknowledge, Neil, like, I've always been the type of guy that when I wanted to manifest a business, I don't, you know, actually I'll be curious to get your take on the right way or the wrong way, but I just had to scrap it together. Like I've been a duct tape entrepreneur my whole career. Four people out of a house to 90 people. But it took a long time to get there. So I see the value. I don't know if I would have had the confidence to sell my vision when I started at 29. So the table, right, Any money, and money is a scary thing. And for 15 years you've kind of been the guy or passionate about investing and supporting innovative tech. You're based down here in San Diego. You're the managing partner of Interlock Capital. I've really enjoyed also getting to know you over the last few years. We had a chance to go to lunch and my favorite part about you, Neil, is like, you're very real. Like you're approachable. And isn't it sort of sad actually that when you think of VC and that first comment of your about to enter a war zone, that people don't necessarily start there. They feel like they got to put their catcher's mask on and a bunch of equipment on and that's not what I've ever felt from you. So thank you first of all for being like your approachable self. How you doing? What's. What's cooking in your world?

Hey, no, it's. Thanks for having Me. First of all, I really appreciate that. I've enjoyed getting to know you, and I look forward to getting to know you a lot more as well, too, since we are so fortunate to be physically near each other. I'm doing okay. I'm doing okay.

Falls.

Fall is a favorite time for me in San Diego. Going into winter as well. Like, I like when it gets a little cooler. I like that we actually get a little. Little change of scenery and weather here. So I'm ready to pull off jackets.

This right here is where 70% of eye rolls have just happened in this moment. Across the country. We're like, oh, poor you. You have to put on your little viori windbreaker, because it's gonna. It might get to 60, Neil. It might get to 60 degrees. Are we gonna survive this? Windpocalypse?

You know what's funny about this? Just the same time on Instagram, I shared that finance bro vest. Se season is upon us for the same thing. So, by the way, New York is going through in its own regard as well, too, where all of a sudden, the bros are pulling out the puffy vests. And you know what? I bring that up because I get lumped into that. As a investor, I'm looked at as a finance bro. Let me tell you, it couldn't be further from that. Even though at the end of the day, my job is similar. Manage people's money, put it into places that return it tenfold or a hundredfold.

Giving me more color there. And I'd love to. We gotta be careful because we could spiral and talk about this for the whole show, but I really want to sort of hear, like, how did you happen and why these choices for you? But then I do want to help entrepreneurs. And we always talk about where there's fear, there's an opportunity for courage. And I do think that money is scary and raising money is scary. So I want to get to that as well. But let's start on you. How did you get into this world? And did you know at a young age? Did you come from entrepreneurs? What. What's the backstory?

Such a different backstory than when I would have planned. Grew up in a. In an entrepreneurial family in Los Angeles to a father and grandfather who were in the restaurant and real estate space. In fact, the whole family was. In fact, my grandma and mom were also realtors as well. So real estate was. Was in the family blood from developing it, building shopping centers, building retail stores, and then running those retail stores. That's pretty much what I grew up Expecting I would go into that business as well. And applied to college as a business major and was the first person in my family to complete college. Because everyone just felt compelled. A lot of people started it and everyone said, this is getting in the way of business, and quit it and went into business. That's definitely a quote from both my parents, where I, weeks before high school graduation, got pulled in a completely different direction. My physics teacher at the time said, I know you're graduating soon. You've already got into college. We'd really love your help after school on this robotics team. We think you'd be good at it. And like, okay, sure, let's do it and show up. They hand me pretty much like two pieces of metal. Like, can you go figure out how to weld these? Okay. Figured it out instantly. The bug of creating something with your hands was upon me. Like, I was like, whoa, I can do this. And started looking into engineering and completely changed my career trajective, changed my major, changed my schooling, everything. And became a mechanical engineer by undergrad and an aerospace engineer by profession. So that's actually where I started my career was in aerospace engineering. Now odd jobs from high school all the way through college. Always super entrepreneurial. I built a power washing business for my dad and his friends, real estate companies. I built a little pool cleaning business during college. So, you know, I always had that bug. But I also had this bug that was like, go try to create some insanely huge big machines. So I worked on the Bradley fighting vehicle, which is crazy to see it now in Ukraine. I worked on the air conditioning unit there, created the air conditioning unit for the first Bradley, and then worked on the space shuttle program, which, you know, probably might be the most complex machine ever created so far to date. So got my hands dirty on that and loved it. But once I was thrust into an environment of thousands of engineers, I realized, you know, it was a little too much of the same thing. Love the people. They're the smartest people I could have ever surrounded myself with, which was a big lesson to not just smart people, but passionate people that wanted all had this core mission. They wanted to put people in space. Like that was their entire North Star. Most of the people, most of their life, that's all they ever wanted to do and fulfilled it and did it. And so I don't think I realized what it was like to be passionate about a profession until I worked on the space shuttle program. And therefore, when they retired the program and started letting go tens of thousands of engineers in mass My heart was broken. I was not let go, but everyone else I knew was. And I had this survivor's guilt, like I had this like, why was a 50 year old engineer who's literally the smartest person on turbo pumps out on the street, has only ever worked on space, doesn't necessarily know what to do Next. And here's 25 year old Neil being like, you know, I guess I'll just keep working. That didn't sit well with me. And the entrepreneurship bug hit again where I decided what if I built something to help engineers get their next job. And so that was a big pivot for me with a good friend who became my co founder who got let go. We built a prototype for what we thought was LinkedIn for engineers. So that was my first startup almost 12, 13 years ago. Eventually was called Portfolium. It was, it had some major pivots, as you know, entrepreneurs know that you have to go through. And it became LinkedIn for students. So we actually built kind of an ed tech higher ed platform to help students track their learnings towards employability. So it wasn't necessarily like a jobs platform, it was a visual resume that added a marketplace element where, where colleges could understand what students were actually enjoying, what they're good at and what they're employable at. And then companies to tap into that and start recruiting from the platform by connecting with students early in their college career, if you will.

Neil, that first business like the, the LinkedIn for students, did you start that with someone you went to college with?

We didn't go to college together. Well, we actually did go to college. Adam Markowitz and I went to university but never met at ucsd. We, we met the first day of our, of our aerospace job together. So yes, we were, became best friends or good friends, co founders and even eventually roommates all work on this business.

So it was like 247 as someone that obviously is looking at the future, right. And I think there's a lot of conversations right now about the benefits or lack of benefits of college and like to hear your parents say we're just going to start working, right. This is not a new concept. But I've always felt like college is the best place to experiment. And I'm not talking about between the hours of 12 and 3am not that.

That'S not all the things, you know.

Experimentation, right. But to me it's the, it's the network, it's the relationships, it's the finding commonalities with other people that went there. And so even though it Sounds like, I mean, again, without. Who knows if you would have started this first business together or not. But I'm sure it instantly was like, oh, it's almost like a shared value. Like that's a shared at least denomination to that. You both went there at that particular moment. So, you know, I, I, my kids are far away from college still, but I am of the proponent. I've had this conversation with a lot of people like, no, like college absolutely has a place to like, experiment. Grow your chops, grow your skills, grow your network, build some real relationships, learn something new. Right. So there, there's my box check for, for college. I, I also have to say I.

Would love to have. We could go deep debate. Because I am in a state where I am grappling with the value of, of it these days. Because I spent seven years selling into universities to understand who really has the right carrot dangling in front of them at a university to help students for the rest of their life. I am unsure of, of, I'm like morally torn right now of its value, economic value per se. So that's a whole nother episode we can do together.

It totally is. And I'm also will be the first to tell you that I don't. This isn't that every college gets a trophy, which is what's happening, or that every college should charge what they're charging, which is happening. So it's definitely ripe for disruption. And you're right, this is a rabbit hole has begun. We'll park it. I think it's cool to hear your multiplier. Like you were, you've been in, you've seen real estate up front, you've seen the restaurant business up front. You were an engineer, you're an entrepreneur. Like, I do think this is a one plus one equals three thing. And it's what happens with a lot of people, it feels like is they get, they go into a vertical and then they get deep and they think that's what they're supposed to do. And 25 years later that's what they did. And for some people, that's okay. But to me, originality often happens when you see something in one vertical all the way over a year and like, wow, why isn't anybody bringing, applying that into this vertical? I mean, you're getting constantly, I don't know what word to use other than pitched. You're getting pitched all the time on different ideas. Do you see it that way too or do you see it differently?

Oh, I do. Kind of. Back to your original value of college. Actually like experiences shape you and without experience, you don't know, I believe, how to value other things that are brand new and foreign to. And so there's that. Right. Which I believe people should experience as much as possible. It's when I tell students when they're, you know, you should go intern while you're a high school student and intern every three months to go experience how you like to be managed, how you like to, you know, work with others. But then the actual force multiplier that I get, that I see is the co founder mentality. So imagine just your experiences now. Put someone else's experiences layered into that together. And the more diverse your experiences are, the more one plus one equals three in that regard as well too. So high level. Everything for me as an investor, by the way, is what I look at myself at is I am a talent scout looking across everything for great talent. And I actually describe to some people I'm a talent scout for talent scouts, meaning I am out there looking for great scouts who can assemble a great team that can turn the team into a great business. Right. I'll give you the tangible aspect of it. I meet a CEO and co founder, could be whatever they are, cto, whatever there I, they're saying, hey, I'm pitch, I we're raising a million dollars to go build this thing. Are you in? And I say, well, tell me more about this thing and what are you going to do with a million dollars? And that million dollars is everything is what are you going to go spend it on to go turn that into a hundred million dollars. So that's kind of the, like what, who are the people? Usually by the way, that million dollars is spent on people. You're going to go hire people to go do the things that you have already figured out that you hand off, you optimized, you're going to delegate and then you're going to, you, the founder are going to go work on the next hard things, figure that out, hire people, hand the stuff off. So that's how I kind of look at myself as a talent scout of talent scouts in that regard.

I feel like we have arrived at the table. So here we are at the table, right? And you're on, you're on one side and you're auditing, right. And I have my own fear on the other side, right. I'm like, please give me the money. Like, please. I see it, please. We have a vision or whatever. However it is, we don't say it like that obviously, right. But, but you know, as Observationalists. The job is to hear what's not being said sometimes and that's kind of what the conversation is. So first we'll go co founders. Because I'm sure looking at a founder is different than looking at co founders. And like, the prioritization of cues you're looking for when sitting with the founder might be very different than we're sitting with two people or four people. So let's go with the one. Just keep it really simple. X person shows up. I've already heard from you. It's like this person, do they have the it factor? Like, you know, I mean, is that. What are you looking for? Give me like, what's the gold medal, the. The silver and the bronze.

Ooh, this is, this is everything. This is like how I do my job as a talent scout. Right? Like how, by the way, this is what humans called building rapport. Like we judge everyone, Right?

Right. Yeah, absolutely.

You know, and how we do that is data points about the person. So the first time I meet someone, that person ends up on my social graph. Right. Think X, Y axis. Remember engineer here, I'm going to nerd out on some stuff here. So there's, there's going to be, you know, data points, both X and Y in two axis, maybe even three around. How do we meet? Right. Was it cold? Did someone give an intro already? There's going to be some back channel accent data about, socially about this person. Now if I am forced to make a decision right then and there, off of one data point, can imagine I'm only going to do what is right in front of me. Right. We've got 10, 20, 30 minutes together. Maybe just in a zoom where half of it was me introducing myself to you. You're not giving me a lot to work with. So it actually behooves me to get as many data points about someone as possible and vice versa. By the way, they should be getting to know me as much too, to say, are we a good fit to spend the next 10 years of our life together? Because that's what we're signing ourselves up for of where I'm investing at the earliest stages with someone, maybe even pre revenue all the way through exit. So the more data points, the better, meaning better to not make the big ask in that first meeting where we've got 15 minutes about each other or I'm going to drag my feet and. Well, two things. I'm either going to say no right away because I don't have enough data and it may not be worth my Time to spend more time because your time is constrained or I'm going to drag my feet to get as many data points as possible. That could mean like hours together, could be days, weeks, months, years. And in fact sometimes we've found within interlock, our average time that we have known a founder before investing is nearly two years. So behooves everyone to get to know everyone sooner than later. Because what we're doing is de risking our investment. And the way that we do that is we try to understand your decision making process. If we know that you are going to make smart decisions, well then you'll. If you've made smart decisions before, good chance you'll make smart decisions going forward. Therefore a little bit less risk than not knowing any of that background. So it's a little tough to say, you know, right then and there. Now let's say now. Let me tell you what's going through my head a little bit. In the moments that we are meeting, I am assessing, comparing you to a cohort. I'm comparing you to other business owners. So have you run a business before? No. Yes. Already. There's already a stack ranking. Have you sold a business before? Have you hired people for business before? Have you fired people? Have you managed the team? Have you managed managers? Managing a team like all of this are, you know, simple in a sense on paper, but that all goes into it. Meaning first time entrepreneurs, never started a company, never raised capital before. You know, Ari, a bigger hill than someone who's been there, done that before. Six, seven, eight times. Then I start looking at the industries you've been in. Do you have any real world experience? Do you know the customer already? Have you? Maybe the customer was you and you've built this and you intimately know, you know the CPA accountant world because you were one and then now you're creating software for one. Or is this something you're just getting to know and you're learning right alongside? Meaning are you learning on my dime? Right. So there's a lot that goes into all of this and that's why it's talent scouting. Because I am, you know, constantly looking at a cohort in front of me and saying who is the best person to deploy this money into?

Well, I love the XY axis. I can totally see your. It's like the scene in Beautiful Mind with the string. The yarn is going everywhere. I'm not sure what color yarn is when it's green, if it's red, if it's yellow, but. But it's really cool to get Your perspective and making the most of a 15 minute to an hour long meeting, trying to extract out what you need to and being super intentional, very engineer like of you to articulate that. Let's, let's flip it. And you had touched it on it a little bit. Right. From the, from the entrepreneur standpoint, who's never raised money and is terrified. Right. Believes in what they're doing, know they need to show up, know they need to show up, show good. But like there's a lot of stuff out there about VCs and it makes the process scary. Right? Give us now the same thing. What's the gold medal, the silver? If the roles were reversed, you already touched on it a little bit. Like maybe don't go for the ask, but get to know somebody out of the gate. But like what are your gold, silver and bronze for that newbie first timer that's just trying to figure out this process.

It's a great question and it's not inherent. I'll give you the cat, the catchphrase first, not all money is created equally. So a lot of first time founders think I just got to get cash in the bank, I don't care from who and get back to work deploying it. And yes, theoretically you could, you could go raise, you know, $1 from a million people and never talk to them again and go do your thing. Or you could spend your time building the most, the best list as a CRM to get the best investor possible. We call it smart money or strategic if you will. And so it behooves an entrepreneur to get to know the investor to say beyond the check, are you going to work for me when I'm sleeping? How much are you going to go to bat for me? Can you open doors or can you give me cheat codes on things? So imagine I am building the new resident residential real estate. You know, map startup. Wouldn't I want the founder of Zillow on my cap table? Because they're going to be like, hey, I just spent 20 years building this. Let me tell you everything I should have done in 10 minutes as opposed to, I don't know, a cardiologist would be like, I can tell you everything there is to know about hearts, but I don't know anything about real estate. Right? So the where the money is coming from and who it's from and what you get out of them matters a lot. And at the earliest stages, when you really haven't built a business yet, time is actually your most valuable currency. You need to not go make Poor decisions with that money. Like go build a product before knowing you have a customer. Someone could tell you that. Go get an introduction from your investor to your dream. Hire other investors that have relevant expertise, maybe even your top three perfect customers. Your investor might know that and might be able to literally do that in five minutes. Make introductions and say, hey, let me just walk you right into the door and save you 18 months on everything you're about to go do. So that's the biggest thing I would hope that entrepreneurs do is spend the time getting the dream investor that does more than just write a check and disappears.

But we get this wrong and next thing you know it's the opposite. It's the nightmare investor. Right. And look, I'm sure you've seen a few things. I try to be prepped for this stuff Neon. I'm really fascinated with just that, what goes on in the minds of those little moments. And we speculate, right. And it's very easy for us to feel like I'm going to get hosed and I'm going to have a nightmare partner. Right. And like you said, you've been doing this for a long time as the MP at Interlock Capital. So I tried to like come up with very quick, succinct little statements. I'd love to sort of rapid fire, yes, no on the important scale if you were going to add these to your xy, you know, access one. Choose partners over brands. If I'm, I'm trying to raise money, I'm looking for a partner over like.

The brand name partner all day.

Believability, belief. Seek out investors who truly believe in what you're doing.

Absolutely believing in people. I'm investing in people, not the idea.

Do as much research you can on the investor first before you ever step into that room.

Yeah. Online, but honestly the back channeling, asking people who know people, you'll get authentic feedback as opposed to whatever's online.

I think I know the answer because you kind of hit on this but just triple stamp a double stamp on this one. Avoid educational meetings.

This is a tough one. I like. Yes, but. So you don't want to waste people's time, but you do want to put your first meeting out there where you aren't asking for something so that people actually intrigued to be like, oh, you didn't need something from me, tell me more. There's this actually great key phrase in investing is ask for advice, you'll get money. Ask for money, you'll get advice.

Oh, I like that.

So true. For sure.

All Right. These, these last two, I think are in the, the gray. The gray zone, which is why I'm ending with them. It one sounds so simple. It's like, yeah, but we're human beings, so that's. Don't take anything personally.

Totally true. What else can I say about that? I mean, yes, like no one's really that malicious to really do something against you, especially from the investor entrepreneur relationship. Like if we're in, we're in for the long haul. Torpedoing you torpedoes us. So I don't know, I look for the good in people.

That's interesting you said the long haul. Because my last question on the topic is set a time limit for your raise.

For the raise, Absolutely. Run it like a campaign. It's a sales, it's a marketing and sales funnel. You got to work your CRM, you got to get people to come along for the ride and you got to put a sense of urgency in for people to say yes or no or they'll take as much time as you give them.

So, you know, often as I'm asking these or bringing forward these comments, questions, is there one missing from my list that I should have asked you?

People tend to ask a lot about, you know, revenue or not revenue. Like raise money before revenue or not before you have a product in market per se, have any customers. I would say you're always raising and you should be raising from the smartest people at the earliest stages where you're telling them come along for the 10 year vision and ride and the money will come if we believe in what we're trying to do. I also would say that a lot of people are scared to jump off the ledge. Meaning, like, how do I do it? How when's the right time to go all in on something? And there's a great quote that I love around this that says it doesn't, you don't need to be great to start, but you do need to start to be great. And if you are always fearful of looking over the ledge but never will jump, you'll never, you'll never know. And so you gotta incrementally do it and find the things that tell you. Yes, yes. But you can't be fearful of, of ever ripping off the band aid and going in on it.

So, you know, we both have podcasts. Yours is the Taco and tech podcast. Very fitting for Sand Diego. Does that also mean yours goes live every Tuesday?

It's true. Taco Tuesday. Every Tuesday you can hear another episode where we interview someone.

All right. Just making sure you know our roles because we wear a lot of hats. Right. Like, being a podcast host is very different for me than being a keynote speaker. It's very different than being a consultant or an advisor. And you have to kind of know your lane and know your role. So like when you're being pitched for money is very different than when you're trying to be disciplined about the questions you ask. Right. But to kind of stay out of the way as a podcast host, when you think about the different hats and I'm sure you've got an XY for this. What, what's the notes that you're trying to hit as a, for the Taco and Tech podcast.

With Taco and Tech Podcast, I'm interviewing like technologists, founders of companies, but visionaries. And so what I am doing is trying to ask questions that pull out a good story and a good narrative and get out of the way, but make sure that they're looking good but in a non threatening way. Right. So in a sense they know from the front, like, hey, I'm not trying to trip you up or trick you. The goal is to share a very authentic story that people would like dream of sitting in on a conversation happening. Right. And so that's my style of, of interviewing now by doing that, people are, have their guard off, don't feel threatened and you know, really show their true self. Which means it has been, there has been a number of people where I met for the first time on the podcast that I then followed up and said, hey, are you raising? I'd be interested in investing in you. And so it has been a way to get to know people because they aren't pitching, they're being, they're, they're telling kind of their true, authentic story.

So if you think about your authentic story, if there's like one thing that you haven't shared on your podcast about you and it could be something you're afraid of, you know, just fear and courage. It is, there's a vulnerability opportunity, right. Like what's something that people don't know about you that does sort of okay, if this is going to keep me up at night a little bit, or I am a little afraid of X, Y or Z. Is there, is there something that you can share?

Yeah. I mean, as an investor and even as an entrepreneur, we, we have this tendency to live both in the now and the future. Right. We are constantly pitching, telling people on here's what the world's going to look like because we are building this amazing thing or because I'M investing in this amazing thing. It's in the future. It doesn't even exist yet. And the people that you start to be around start to be like that as well. There's a little bit of an echo chamber of like. But look at those amazing things that are happening and you for kind of forget what the real world is like sometimes. Like what the actual problems are today that are worth solving. So you know, for us, for me there's a little bit of remembering to live in the now and the realism now and don't just live in the here's what, how much better world's gonna be like 10 years from now. And I mean not the world even like our personal lives. What, what life is gonna be like. Right. We're so forward thinking as opposed to looking down and being like where are my feet right now? Am I planted in the right spot today to make 10 years from now look amazing? So that is a bit of a piece that's tough to struggle with and distortion from reality sometimes.

I really appreciate that because hearing that I, I have a 10 year old and 8 year old and so. And I love what I do. Like I'm. It's wide enough where sometimes there's like a courageous conversation that has to happen from the stage or we get to roll up our sleeves and help a company figure out their tomorrow or I've even described us as like we're business mechanics. We're looking under the hood of a company. Like oh here's the problem. You actually don't have values that are meaningful to the organization. So because I get so energized and excited about it or I'm on the road, I forget like there's little people here that need me as a dad or even a wife. You know, that's like hey, I'm not just mom, I want to be wife too. Right. Those are different labels. Yeah. Do you feel like is that where you're going with some of this as well? I mean you're new one, one child.

Yep. I got a two year old girl so new dad that you know this is it. Right. It's like how do you show up and be the now for the hard stuff which is who's changing the diaper right now at three in the morning when you're like but I'm busy creating and solving $10 billion ideas that is going to change the planet. Don't you know? Right. So like there's yes, absolutely. Like living between the that and the. You know, I'm just Neil. That part as well, too.

Just Neil is a good name of a. I'm just. Neil is a good T shirt or a good blog post or. Or something. Something there. All right, let's end the show with two questions. Same question, done differently. I mean, I'm sure there's been an investment that you guys made that you were so sure of. And it was like, oh, what? I did not see that coming the wrong way. And I'm sure there's also an investment that you made that you were like, okay, it doesn't hit all the boxes on the. The axis, but I'm in. And holy. Like, wow, I did not see that. And so I guess it's sort of acknowledging some of the places where you've been wrong. The hunch was off in both directions. You benefited from the hunch paying off, but you also were like, I'm telling you, this is going. And can you share a little of the stories? But also more. More than that. What are the lessons from it all?

Yeah, a lot. So as a. I started as an angel investor just investing my own money, and. And then you go into. Then I went into managing other people's money, Right. Taking other larger checks and putting that to work. So at the beginning, as an angel, I find I fall in love with founders very easily. Meaning I've. I'm investing in people. I fall in love with passionate people who are confident but also authentic in what they do and what they don't know. And I say, I'm in to learn. Here's my ticket. My check is a ticket alongside you to learn alongside you, the entrepreneurs, the founders. So in a little bit, I'll jump to the end of a few things that have happened in things that have folded. Whatever. The first question I ask is, would I invest in this person again? And that's. That has become a bit of. My thing is like, am I in for the ride with this person, this team? No matter what, am I there for them, regardless of the check size that I wrote, regardless of what happened in the end? And I would say 99% so far of the times I have asked myself, like, I do it all over again. And I make them know that, like, tell me what you're working on next, because I'm ready to write my check, even if it was a big fat zero for us.

That's really cool, by the way. How cool is that? But that also means you probably are good at knowing when to be available and also knowing when to stay out of the way, right? Because I think there's a Fear of that balancing act, too. Like, oh, I didn't see Neil for three years. That doesn't sound like I'm not going to hear that. I'm going to hear you're available, you're around, but doing in a way that isn't, like, suffocating to the entrepreneur. I'm sure there's a balancing act on that, too.

Totally. Yeah. No. And part of my pitch to the founders to take my money versus someone else is right up front to show value intrinsically outside of money. So whether it's a. Let me show you my network real quick so that as soon as we're in together, this is who you have access to for the rest of your life. And I try to show, you know, a very tangible connection. Like if you're building the next sports betting platform, boom. I'm going to introduce you to the two original founders of FanDuel, Tom and Nigel, who are in my group. And I'll get out of the way. So there's that aspect, right? Is like show value right up front that it's like, I'm. You're not gonna have to wait and you're. For me to show up for you, and I'm not going to disappear. And even if I did disappear, you know what to come and ask of me for help. So there's that piece for sure. But. And so certain investors get in the way by getting on your board and scheduling weekly meetings and, you know, for certain reasons because they think, oh, I gotta keep showing my value or I gotta sit on this person, you know, so that is probably why investors get a bad rap is kind of the overbearing nature, maybe that says, hey, I'm only looking out for our financial upside. I think you bring up a good point of the balance of time and energy and everything else as well, too, that says, look, I have to be upfront and say, I am not going to be able to solve all your problems, but I am in as a member of the team that says we're better off solving this together if I can provide value here or I can be helpful to you. So that's my style, and that's what you kind of get. And so therefore, I have to be. I have to assess the talent to say, is this someone I can work with? And even, you know, when times get tough, are we going to have an opportunity to. To get out of it together or not? So that part's tough, you know, to assess when everything. When you're pitching and everything's like, rosy and amazing and look at us, you know, so, so I have had a moment where as soon as the check was written, a week or two or even a month went by and they said, shit hit the fan, we ran out of money. We're like, wait a second, what? Like, we all just wrote checks. What just happened? Oh, yeah, well, we had, we used it all for debt. We, we, we got none left. So that has happened. And that is a checkbook check on our end as investors to be like, okay, can check all you want on people, you also got to do the deepest diligence on the business as well too. Right. And so as much as we are people investing in people, we're also investing in businesses. And so lesson learned on our part, that's for sure. On a diligence standpoint, we've got a checklist now that we're investing in good people and good potential businesses.

I would say if I step back and think about. And this was my last creative agency that I had started was Emerge, and it was a PR firm. We were on the strategy and the creative side. They were on the pr. I'd say they're on the social media side. And I loved that they look like adults. Like, I thought that raised our price point and I think they, they appreciated our, the, the brands that we had worked with from a, from a national standpoint and our created product. And looking back at that mesh merge, we, we, we made it together for five years. We, we did grow it, but we were two cultures in one. And looking at myself, I'm like, wow, I was a terrible partner.

Why?

Well, I, I think the, the further, like we had tested each other on a few projects and we had won three in a row. And I was like, oh, we're dating, we're dating. So like it was like the value prop was working and which is what we do, right? But when it came down to the logics were just off on the way we went about problem solving. And to be honest, it wasn't like they were bad people or I was bad people, but if I look at even my own actions, when I finally realized that I didn't feel like I could get us as a unit where we wanted to go. I, like, I had secret meetings with other leaders in the business because I, and this wasn't conscious. This was like, I'm just trying to solve the problem in front of me. And looking back, I'm like, oh my God, what a terrible partner I was to my old partners now. Now that said almost every, you know, we, we started every Week together on Mondays. Almost everything I learned about leadership started by how did we handle very tough situations. And I'm beyond grateful and I'm grateful for the work that we created. And the real problem, this is a very long winded way of getting to this, was that I don't think we had our diligence checklist on them vetting us and me vetting them because no doubt, like we wanted to be, we could care less about being big fish in a small pond. San Diego, we were like, I had come from the New York agency background, like we were interested in being a significant player in the US And I should be careful now when I say we. I was interested in being competing in San Francisco, New York and la. And so as we kept growing, half of our culture represented, you know, where I wanted to take it and half or more local regional pr, and that's okay too. But together it became very clear that we weren't gonna, we weren't gonna get it to where we went to go. We weren't as clear as we could be. To your point earlier, we didn't just like, think about people in space. There wasn't, there wasn't clarity. You know, one of my friends says clarity is a rarity. That is really the business that I now find myself in. And so you have to own the, the punches to the chin. And from an alignment standpoint, I'm like, wow, it's amazing what we were able to still build together. And when I finally said it's time for me to go and I need to fire myself, which is a whole nother story over another podcast, it was because I knew in my heart that everything I had learned writing my book Return on Courage, we weren't aligned on. It was like a new business tool for them versus a way to help companies be more courageous. So when you say you're a talent scout and it's all about the people, man head nods like, I. And how cool is it that you have the ability? Like, you're like, I have money. I have access to money now. It's about, about finding the right people that want to build rocket ships, sometimes literal rocket ships that make us all, all better in, in the next three years. I'm curious if there's like one thing that you're super excited about from all these interviews and all these, everything you read and one thing that's like, oh, shit, you know, I'd love those, those two answers. I. I almost feel like I'm doing the audience a disservice, though, so hold on. Give me the name of the business. You can you give me one or the other, even one that was like, I never thought it would get that big or would go and it. They proved me wrong. Give me one from the fund if you can.

You want me to name my name, my book? You want me to call out one that's not, that's not doing well?

You can go either way. Yeah, either way.

I mean, hold on. There's so much to like reflect on there with you. Even one. Let me just look back at what you just said around the secret meetings, around the business, like it was coming from a place of good, of wanting to bring the business forward. So there's nothing malicious there. I can't fault you from a partnership perspective. What I see bad partnerships sometimes falter is two areas. One, like you don't address head on the, you know, passive aggressiveness aspects, the things that you're not, things that should be said that aren't being said addressing it. And timelines. I think when it comes to money, what something I've learned from managing other people's expectation on investment is that everyone's got such a different mentality on return, on investment, investment timeline. Like, if I'm putting in a dollar today, am I getting back tomorrow? 10 years, 20 years or never? All of that matters. And that is true for entrepreneurs to manage timelines of the investors that they take in that regard.

I would, I, I would, I would even say on this that we were in very different life stages too. They were older, probably a little bit more. Hey, let's get to the return. And that there was the amount of. We weren't afraid to have hard conversations. And I don't even know if it was. Well, they're probably like, you were passive aggressive. But for me, I'm like, we're not done investing, we're not done investing. I, I remember constantly saying we're not done investing. And I'm sure from them they were frustrated on. Well, you know, we're in our 50s here. Let's go already. So anyway.

Yeah, yeah, okay, got it. Yeah. No, and those are things that I see breaks apart founders in that regard from not having those conversations timeline wise. Okay, so we've got a business called Verity Case that is solo founder Carrie Leslie, North County San Diego, who came from the biotech world and understood, saw like metals in the biotech space, say like surgery and how it's recycled and reused for back surgery and knee surgery. What if we did that in other aspects of our life and tried to Remove the plastics and the consumables and built a business in the beauty end beauty space that brings metals as your casings or hardwares for that. So think of like your razor blade model, right? You buy your handle and you keep getting replacement razors. The thinking is the same for makeup. You've got your metal case or your deodorant metal case. You get refillable scented. And you know, when we met her, she was running through walls doing amazing things as a solo founder of bringing clean beauty to the masses. And Covid really affected supply chains and therefore accept really disturbed people's mentality to shake up, you know, their practices, which is casings and. And the hardware. You know, they're not beauty brands are not necessarily focused on the plastic. They're focused on what's inside it. So that one still amazing founder just hitting a tough time right now just from the state of the industry. But man, she's gonna. She's like always running through walls in that regard. So we're excited I think because I'm not officially saying this, but she had a mage. She's not officially talk about Harry Styles's lip balm line bring using their packaging for the lip balm. But big lip, the lip balm is using metal packaging from Verity. So that one to be to be determined if people will make the switch to metals instead of plastics in the bathroom. Let's talk about. This is gonna be another hardware one, but that's okay. No, I've got one. My very first investment company called Trust and Will by all sense make your people right now everyone looks like, oh my God. Amazing. Well, when I met Cody Barbo CEO.

And Cody's been on the pod. He's been on the podcast before.

Amazing. Awesome. Great shout out to Cody Barbo cb And so Cody and I had our previous businesses were complimentary. He had LinkedIn for the restaurant industry called Industry. And I had founded my company LinkedIn for students a year or two ahead of him. And we kept kind of were circling, orbiting each other through the startup world. And he was always kind of a year behind me on the startup pitch competitions. And he had a falling out with his co founders, which happened to me in a prior business. And he came to me and said, what do I do? And he was ready to just like either go get a job or just be a consultant to a bunch of people. So Trustworth was not even a thought yet whatsoever. But literally. And him and I go back and forth on this a little bit. I thought I said out loud Cody Whatever you do, here is my blank check. I guess I must have maybe just said it in my head, but either way, the moment I saw him, like, at. At defeat, in a sense, I was like, I'm betting on that person because they will run through a wall because I. And so six years later, maybe, you know, I think it's a time thing, but also a people thing. It's my best performing investment on paper by and far. But either way, to have been alongside for the ride with him and his co founders, Brian and Daniel is worth the price of admission. To see them grow as people, to become dads and learn, you know, and watch that and be a part of it. I wouldn't change anything whatsoever. Sure. Financially, you would look back and be like, I wish I wrote a bigger check. Whatever, you know, like, what matters is that I've been along for the ride and I'm super proud to where they're headed.

Here's another really good dude. You know, to be honest, I know Brian too, and Brian's another good dude. Like, unless they've got me fooled, which I don't think that that's not their style. Like, they're both good people. It's a great place for us to sort of end. It's. It's always good to, like, do good with good people and. And I'm excited to sort of see what you do next. If the roles were reversed and I. I came on your podcast. Last question. I'm giving it to you. By the way, what would be the question you would ask me?

Well, Ryan, if you were on the tacos and tech podcast, I'd be asking you, what is your favorite taco spot?

Oh, well, I mean, look, obviously it depends what time it is, because my, My answer will depend, really does depend, if it's 11pm versus 11am right? If it's 11pm it's Cotillon on the way home, because that's the only place that's open. But it's also really awesome if it's 11am as far as I'm concerned. And you can, you can call me off on this. There's only one place I know in San Diego that people will stand outside in a line the one day a year it rains. And that day is. That place is Quatra Milpas.

Okay. That's is been named many times on the podcast. People stand outside for taco stand and tacos el Gordo, but maybe not when it's raining.

I think tacos taco stand always is a line. And I love taco stand as well. But like people stand outside in the rain. That's. That is. We're kind of back to. It's, it's. Get your. Get your jacket. Jacket ready. Right.

You're right. Yeah. That is so what we say on the tacos podcast, there's no wrong answer. And there is a taco for every hour of the day as well. Like, people are always like, I'm about to say Taco Bell. I'm like, hey, there's a time of day where you need Taco Bell and I don't hate you for it. We needed fourth meal.

Fourth meal. They made the whole category. Bravo.

We've interviewed about 250 people on tacos and tech podcast. We've now created a tacos and tech database naming every place that people have named. And we've got like the top 10 most named. It's. It's pretty fun. So I'd love to have you on. This is an open invitation right now to talkers and tech podcast. So let's make it happen.

I'd love to, man. And it's really cool to get to know you too. I know we're just getting started and I imagine to the audience like bromance is happening, but yeah, it's. I don't see how our world. There's a lot of curiosity. I'll use that word over courage. There's a lot of curiosity and for both of us doing what we do and like. But it all comes from a good place of like, what could the future look like? And how do I be part of those moments and, and how do I do my part in those moments? So thank you so much for sharing your story and for, I think also taking the, the scary table. And for anyone who's really listening, that is in the. Okay, should I raise money Space. You know, the good news about this show is it's not like a Snapchat where it evaporates at the end. Like, go back and listen again. And there's some really good little gems, Neil, that you shared. So thank you for doing that and I'll, I'll see you out there. I'll see you out there in the taco place pretty soon. Right?

For sure. No, thanks for letting us giving us a space to have these conversations. You know, I think it's very easy for people to make a grand assessment about investors in their puffy vests and be like, all VCs are VCs. And I hope that by what you're doing is you're putting a human face that business is human and vice versa. So thanks for this. Thanks for the conversation. I look forward to more of it.

You got it, man. Thanks, Neil. Be good.

Thank you.

Thanks for tuning in to this episode of the Courageous podcast. If you enjoy the show, don't forget to rate and review us on Apple Podcasts so more people can find us. See you again next week.