The First Customer - How To Avoid The Pain of Missed Opportunities with Founder Charles Sims

[00:00:28] Jay: Hi everyone. Welcome to The First Customer Podcast today. I am lucky enough to be joined by Charles Sims. He's the hurricane CTO, which we're going to figure out why he's the hurricane CTO. And he's the founder of Investimate, which he sprung on me last second before the call.

How dare you, Charles? Nice to see you, my friend. How are you? You

[00:00:46] Charles: Nice to see you. Thanks for having me.

[00:00:48] Jay: got it man. so I see you're in California. tell me where did you grow up and did that lead to you being an entrepreneur later in life?

[00:00:55] Charles: yeah, so I originally was born in Longmont, Colorado. Out there in beautiful Colorado. Everybody from Colorado comes to California. Everybody from California goes to Colorado. So it's an even trade. anda lot of my initial childhood was actually watching my mother start her own, aeronautical engineering business, working with the government, building satellites, all that fun stuff.

And so that's what really kind of originally triggered me to want to be an entrepreneur. I wanted to be that serial entrepreneur that was just going and building and building and building, moving on to the next thing. But the, seeing how much, Like she was able to create and innovate and, invent at our home, like at her home office was awesome.

And so I think that just being in that space, being around,those personalities and whatnot, definitely led me towards wanting to have the entrepreneur style spirit.

[00:01:47] Jay: Give me your best and least best, I'll frame it that way, character trait that you think that you see that you got from your mother or, you know, from things that she learned in business, what's one of the best things that you've learned from her, and maybe one of the things you saw her struggle with that you've maybe find yourself doing too.

[00:02:08] Charles: Absolutely. That's a great question. So I think one of the, things that she taught me was. How to really hold yourself in a executive, like if you're speaking to executives, all the way down to if you're speaking to like an intern or a completely, non technical person and approaching every single conversation in a way that person wants to be talked to and talk with.

So being that chameleon, able to talk at the board and present, to executives all the way. To being able to like rally and,get the, team excited to, follow, but one of the qualities that I even today still struggle with, I know she ran through it for her. It was being the female, in the room, like she had always mentioned.

It was. Very, very difficult to be able to be confident in yourself when you're given so much feedback of like, you're just lucky to be here. You, but then you talk to those people today and they would always say she was the smartest one there. She just happened to be,that, and for me, it's confidence.

So like it's, am I really good enough to be able to be talking to this billionaire to get investment? Do I really know what I'm talking about when it's being,like the technical vision of. Investment or for at UTA and that confidence really comes from feeling like I'm always having to prove something, but then once I'm there and I am, I can roll in a rally with the best of them.

[00:03:33] Jay: Love it. All right. Well, what was the first business you started? 

[00:03:37] Charles: when I was in elementary and middle school and I found out, oh, if I have a business license, I can actually go to the paintball wholesalers, get a wholesale account. And create a, way for me and my buddies to get really, really cheap, almost like 70, 80 percent off retail for paintball guns for the, paintballs.

And so I created an LLC in Colorado called Gotham Paintball, thinking that I was doing Gotham City, but I actually, misspelled it to go them. And instead of, G O T H A M, but, yeah, so that was the first official business I started and, it was just to get a cheaper label here.

That's beautiful. do you think all the kids that did something like that, like, I wonder what percentage would you guess are running a business today? So I think today you see a lot more entrepreneurs than you've ever seen before you're a, because you're the barrier to entry is nowhere near what it was way back then, like even me,applying for the LLC and getting the business license and all of that was still like somewhat difficult. It had just finally come online.

so you could apply for it online, but like today you could set up a business in 15 minutes on Stripe Atlas on first base. And so that's a lot easier than the content community has made it. So even if you have a regular job, you can have it, you can have like your side hustle. that is a business technically.

And then you're doing whether content creation, what we're doing right now. so I would say it's those kids that grew up selling candy at school definitely are at the top echelon of the CEOs maybe, but the people all around them also, are very likely to be, in the entrepreneurial, space at least.

[00:05:17] Jay: Yeah, it just made me wonder. I mean, I hear that. I mean, obviously I hear those stories a lot because I talked to a lot of founders. but it did just strike me as like,does that mean anything back then? Does it really like, is that who you are? Are you like different enough where you're like, you're going to go do that?

Later on, you know, I mean, I think,most of my friends that are business owners are, have a similar story, but that also may just be like a very small sample size. So

[00:05:42] Charles: I think,similarity is the people who do very well in business, they were figuring out problems early on. So they were trying to figure out that we don't, we always talk about the, the problem market fit or the,product market fit. And that means you have a product that solves something that the market is obviously in need of.

And as, as we're growing up. If you're selling candy, you're selling a product that the market needs. If you're, you, it's just a solution that you have figured out.

[00:06:09] Jay: It's your hungry, Tam. Like you have like, not only is it addressable, but they're like, I was just talking to our CEO about that today. I was saying, you know, we sell QA services and I said, we, you know, we don't have a ton of competition, like in our. Geographical location or like exactly what we do.

And I said, we, I would like to think of us as, you know, not the guys who sell hot dogs, like in a food court, but like we sell hot dogs, like outside of a coal mine at lunchtime. Right. Like we were like, we want hungry people that have no other choice, but to come to us because we are the ones that can solve their problem the best.

Right. So it's like, if we've come from that, standpoint, so I love that, kind of going to the product market fit first, because I think a lot of people maybe have a little success. With something consulting or whatever. And they go, Oh, this could be a business. And then they go like, business is horrible.

I don't know how to get paid. It's like, well, it's because the first few were just like freebies that came in the doors, referrals or friends or whatever. You didn't have

[00:07:03] Charles: Well, they're selling you as a person. So like if you're selling your own brand, you can get some of those initial sales. That's the friends and family. But then once you actually have to go to the real market and it's not just people that are doing favors, or you can be salesy enough to get in the door.

Now that's hard. That's why marketing is so much harder than most people think. That's why advertising dollars, you spend so much on advertising that you don't realize once you're trying to scale that initial, just getting your first customer or first couple of customers is a lot easier than most people think.

It's like getting the actual recurring customer is one of the hardest things that you can

[00:07:41] Jay: Totally agree, man. I had a feeling we were going to agree on a lot of things today. all right. So what was the,the first grownup business you started? Not named got the guy that they got

[00:07:51] Charles: go them.

[00:07:51] Jay: go to him. Yeah.

[00:07:53] Charles: first grownup business. So, I spent 15 years in operator space. So I was CTO for the Clippers, the, you know, talent agency, and it just left them a year ago. So technically the first one probably would have been the funder AI, which is now called investment,that platform.

Even though I'd always had a few LLCs, like that I used for other things, whether it was for a, for consulting, if it was for advisory outside, but the first like real, this is a full time, founder role was, investment, which is the product that I built. On my, advisory services, because I would get asked so many times, like, how do you like help me build out my pitch deck, help me figure out my product market fit, my analysis, all these different things that founders would come or investors would say, Hey, help me vet this deal flow.

And so building that platform to help me basically replicate myself, to create your pitch deck, to create your investment analysis, the market analysis, the actual valuation of your, your pre rev startup. in the, in that space. And I think that's where a lot of my future businesses will be. There'll be something around like taking my special sauce, whatever it is in trying to make into a product and scaling that way.

[00:09:11] Jay: I forgot you were the Balmer guy, and I actually, I'm glad I forgot about that because, I don't want to talk about it. I don't really care. I mean, it would be cool. I mean, you did tell me a cool story I think about when you first, but like, I, I mean, just let's, I want to focus on you cause this is what the show is about.

Tell me about the hurricane CTO. Why are you called the hurricane CTO? Why do you call yours? First of all, why are you called that? But then like, why do you call yourself that in public? Which are two very specific questions, right? Like the second one is almost more interesting and probably a segue into a future part of this conversation.

But where did it come from and you know, what made you brand yourself like that publicly?

[00:09:50] Charles: So not to bring up Palmer again, but at the Clippers,the story, came that I would always be when things were in chaos, when everything was blowing up and either the network was down or something was happening right before a game, I would be the one that, even if it was a very, deeply technical, piece, I could come in troubleshoot, like start to, delegate out the different pieces that needed to be done.

And then walk away once I'm like, all right, we're ready. We're camera ready. it's can go now. Everything just needs to be kind of buttoned up and cleaned up. And the moniker I got was, man, it's like hurricane. You go into a server room and I'm ripping cords out to try to get. Get stuff going and by the end of it, it's like just chaos in there, but everything's working and we're back up and stable and then that's where I tell the team, all right, you got to go back in and,like buying everything up.

So it's, labeled and easily usable again, that. moniker kept coming and I really embraced it when I was at, United Talent Agency of, I can go into any chaos, any subject matter, not even just technical, but like business wise, strategy wise, legal, the acquisitions that we went through and be thrown into it.

And not get flustered, not be able to not really, get worried about I'm in over my skis because I can always like learn up. I felt I could always just get like, if I just put it down and I can do research faster, I can figure out things much quicker, even if it's topics or even in subject matter that I don't know today I can get there.

And so that chaos then became my brand of I bring. Calm to the chaos. And as I, shifted into what I'm, my personal brand, outside of like investment and the other investments and advisory services I do is this hurricane CTO. So I have a podcast, with entrepreneur ventures, which called a capital grit.

I have a VC decoded and that personality that I'm going into those is bringing my experience from the operator space, coming onto shows like this and kind of branding myself as that. Like her, like the CTO who's been through it all, who has come through and made it through the eye of the storm.

[00:12:00] Jay: Through the eye of the storm, even come with a catchphrase. It's pretty good. I like

[00:12:05] Charles: I'm good at branding.

[00:12:06] Jay: very interesting. well, I mean, you pride yourself obviously in being kind of the fixer, the guy that comes in and give me what's a real time, like that had real impact that you failed and what did you do afterwards?

I think

[00:12:29] Charles: one of the, maybe one of the most impactful ones was an acquisition that where there was this acquisition for a sports media company at,at the last agency I worked with, that we were.really close on closing and I couldn't get, and I couldn't really figure out the value pitch in the technology side.

And I had a ton of pressure from, management to figure out like, how do we actually make this, investable? How do we make this acquisition work? And no matter what I, as much effort and as much,not. I don't want to say like as much narrative as I try to put into it, I couldn't figure out how to crack the nut and ended up just be saying, I can't like, I can't make the valid prediction or analysis of what this is.

It doesn't make sense to me. And,that turned out to be a acquisition that turned two X in less than six months. And this is multiple hundred million dollar company and turned out value of two X in less than six months for the company that did end up acquiring. And so that's a great example of you're in the debt.

Like I was in the trenches trying to do, I knew it eventually turned out to be a good deal, but couldn't really figure out how to creatively make it happen internally. And then that led me to. Trying to build that framework and actually, like similar to what we did for funder AI is build that framework for how do I have a standardized way of thinking about things and not recreating the analysis wheel every single time that we're going into an acquisition or trying to see value in a project or trying to invest in a product or anything like that.

[00:14:08] Jay: Mhm. I like that one. all right,

[00:14:10] Charles: that's a hard question, man. That's a

[00:14:12] Jay: it is hard. I mean, as I, said it to you, I was thinking, wow, I would, I don't know.

[00:14:17] Charles: but it's a good thing to look at. Right?

[00:14:19] Jay: you can't not, right. I mean, if you. Are a person interested in like personal growth, you have to be comfortable enough to like examine your major fuck ups in life, right, which I think we all have our fair share of those.

And if we just sweep them under the rug, I'm a huge fan of, you know, how to win friends of ideal Carnegie book and just like just the mindset shift of like always taking accountability and like always making it my fault, even though if it's A hundred percent. Not like it is right. Because you put yourself in the wrong position.

You put your guys in the wrong position. You put your, you know, you signed the contract without looking at whatever the thing is like at the end of the day, especially as a business owner and as a dad, you know, the buck stops with you, right? Like there's no. There's no room for excuses and like I think the successful business owners kind of know that they learn their lessons from their problems And then they move on so love that you kind of turn that into a positive.

[00:15:11] Charles: Well, I would actually even like push like I because I love the buck stops here and the concept of accountability, but it's also At least in my experience it's knowing when you can give opportunities to others so it's saying like hey I'm gonna put you into this space because it's a huge opportunity for you But I, if you fail, it's on me.

Don't worry. Like I'm giving you that space. I'm giving you that ability and that parachute just in case something happens and you're not going to say, Oh, I can't do this because it's not my speed or I'm not good at it. It's like, no, I'm going to, I'm going to allow you to fail and be okay with it. But I'm never going to forget.

And I'm always going to continue to keep pushing you up.

[00:15:51] Jay: Yeah, no, I love that. And I think it's a really great point. I think If you do that enough, it becomes the expectation and then like, you don't have to have that conversation and you see people like growing in front of your eyes, which like is really cool thing to see with people you've worked with and like, you know, helped build up over the years.

so yeah, that's great. all right, well tell me, a little bit more about funder, which is now not named funder, right? It's Investimate. funder and you got me back on it. So it's Investimate.

[00:16:21] Charles: So invested. Yeah. Investment AI. So investment, the IO, is a platform that if you have an idea, so if you are thinking of a new product or a new business or whatever it may be, you start chatting with it and helps you go through the process of like, what is like, how do you tease that out enough to an actual thing that is investable?

So most entrepreneurs, yeah. And I've experienced this over the last, few years of they have, they might be brilliant and they might have a great product or a great business, but they don't know how to pitch it. They don't know how to speak investor speaker. They didn't go to business school. They don't, they weren't, living in, San Francisco for the last, however many years to figure out how to do those things.

But the grid and the way that a lot of,startups are graded on. There's about five or six models and that's about it. And so whether it's the scorecard method, the step up, the Berkus to evaluate what you're actually, your startups valued at, that's easy. Let's just take that and standardize it into a platform.

So if you have an idea 30, 45 minutes later, you'll have an investment thesis. You're going to have a product,product roadmap, how much it's going to cost to build out that product in dev hours, what the market analysis is, what the investment analysis and evaluation of that idea. As well as like, here's how do you improve it?

How do you gamify your,your entrepreneur's dashboard to sayyou could increase your valuation by 2 million if you go and get a technical co founder, you need to have a, stronger or a more niche thesis. For what you're trying to,approach. And that has grown over the past year to be a lot more like originally it was just, Hey, give me a pitch deck.

And now it's so many of these other pieces that go along to that deal room that you ended up having with investors taking away that fear of not knowing. You don't have to go and be like, we want to reduce that, the barriers to come into the VC space and we want to democratize it. So this is also a platform we're talking with UN to be able to do grant writing.

So how do we help local,local, citizens of foreign countries that, UN's investing in. Apply for a lot of these, VC grants and these,startup, startup applications and whatnot, without having to be the friend of the person who knows how to do that right

[00:18:33] Jay: Right. No, that makes a lot of sense. well, who was your first customer? Who have you gotten on the play? How did you get your first customer? Did you have, do you have your first customer like paying customers?

[00:18:42] Charles: yeah. So we, we have, Yeah, I think we have anywhere from 300 to 500 unique users a day, coming on, which is far more than what, what I expected. Our original goal was 4, 000 unique deal, because the back, back end to the platform is, our, relationship with investors and funds because they want deal flow.

That's the risk they want to have the, Yeah, don't just give me everything that's on pitch book or, Carter would not like, I want to see stuff that is actually promised. Like it's almost, it's already gone through its own diligence itself. Right. so that those 4, 000 deals are coming through.

Sounds like if we partner with a couple more of these accelerators, that might double the next two to three months. And if we broaden it to not just startups and do like what we're talking about with the UN and some of these other non technical projects. But to go back to our first customer was the UCLA Accelerator here in Los Angeles.

They use it as a platform, white labeled, for them to be able to use with their cohorts.

[00:19:41] Jay: So tell me about the, there's just like the monetization angle of this for you guys. So white label, you just threw a new wrinkle in because I didn't know that you guys white labeled it. So you white label it, I'm served. There's some sort of fee or whatever for that. And then you have people that are on the platform and then you have this.

investor side. So you have like the two sided marketplace, I guess, maybe even three, if you'd like make a weird shape triangle with the white label. But, for the most part, I would assume that's like the biggest driver, right? Is those two sides, how do you monetize the whole thing?

[00:20:08] Charles: Yeah. So, the three monetization opportunities are the,the customer or the entrepreneur, but it's free to sign up and to utilize it. So they're not actually having to spend or do anything, but if they're matched up with an investor, there's a piece of carry that comes out of, that relationship and that introduction there.

So that's what the most valuable or the,The highest earning side is on the investor side. So that's where they are paying a monthly retainer to have access to the deal flow and have the model start to analyze what they like in investments and give them more and more, things that are related to what their thesis and what they tend to invest in.

The last one is a white label for any sort of cohort style accelerators, the studio, like think about like YC, but scalable. So like Working with, any of like Red Bull for their basement, which is one of their big plans that they do all across the world. It's just being used as the tech. So they don't have to have 500 mentors to a thousand mentors as they're trying to scale those things up.

It is a platform that scales like a product, not like a person.

[00:21:16] Jay: Love that. It got me thinking of Greg Shepard who runs, Startup Boss, I think, out there. Also another very similar Oh, just an incredible guy. I definitely have to, like, introduce you. Cause in the same space, same kind of platform because we have a company, out here called, Philly Startup Leaders.

And, they That's how I got introduced to Greg was they're using his platform for some of the entrepreneurship cohorts that they do. So I definitely see this model and I'm like, you know, being in the business. Group kind of space you definitely see where this has a lot of legs, for a white label opportunity.

I love that All right, we're up against it But I do have one more question for you non business related

[00:21:50] Charles: All right.

[00:21:50] Jay: for just charles being charles If you could do anything on earth and you knew you wouldn't fail, what would it be?

[00:21:59] Charles: Go to space.

[00:22:01] Jay: Ah, there it is. Love it. I'm surprised that's not everybody's answer, but, you know, I

[00:22:06] Charles: I mean, I mean, what do you.

[00:22:08] Jay: mix of answers, but that's that would probably be mine.

[00:22:10] Charles: Well, let me ask you what's the most interesting answer you had for that question.

[00:22:14] Jay: Ah, dude, I've had so many. most interesting, God, now that's put me on the spot. I would think, I think the most just unique and the only one I've heard say this was be able to fly a fighter jet.

[00:22:27] Charles: Oh,

[00:22:28] Jay: a pretty bad ass, like just raw, cool answer. So, I

[00:22:33] Charles: I love that.

[00:22:34] Jay: I was like, that's cool. All right. Well, if people want to learn more about, you Charles are getting touched by anything they heard today or investment, how do they do that?

[00:22:42] Charles: investment, go to investment. io. and that's investimate, I N V E S T, I M A T E. Or if you want to find me hurricanecto. com, find me on, all the socials hurricanecto and, or on the podcast with iCapitalGrid or VC Decoded.

[00:22:58] Jay: Love it. Awesome. Well, you're great, Charles.

[00:23:01] Charles: I appreciate it.

[00:23:03] Jay: keep being awesome. Good luck with everything. We'll stay in touch and we'll, we'll keep up with what's going on. And other than that, thanks for being on brother. I'll talk to you soon. Thanks, Charles.

[00:23:09] Charles: Thanks Jay. Talk soon.

[00:23:10] Jay: See you, man. Later. 

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