Entrepreneur Intel

EI - Robert Wolfe
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Intro: [00:00:00] This is the unfiltered truth about entrepreneurship. Raw, no VS, no sugarcoating. Welcome to Entrepreneur Intel. I'm your host, Wes Matthews. Each episode, we'll learn from experienced founders and uncover the top 5 percent learnings that led to their success in all things personal, family, and business.

This show is sponsored by Stealth Consulting, delivering clear marketing strategies, ROI, and no surprises.

wesley-j--mathews_63_11-06-2024_150529: So I'm super excited for today's guest, uh, introducing today's guest. So he's the founder and former CEO of Moosejaw, which made retail and e commerce fun and was acquired by Walmart. founder of CrowdRise, the largest fundraising platform for nonprofits in the U S and that was acquired by GoFundMe. He's currently the founder of ZEK, a platform reinventing the board meeting process to make it more strategic and efficient. I'm really excited to dive in there. Uh, he's been an advisor to several companies and this is probably my favorite one out of all your [00:01:00] accolades. honorable, an honorable mention for best break dancer using an old school cardboard mat with an ironic sense of humor.

So welcome, Rob Wolf. Welcome.

squadcaster-4b5h_1_11-06-2024_150529: Yeah, no, thank you so much. Yeah, the last one, my brother was actually the breakdancer, and I have a great picture of him. I literally as a kid break dancing on a pad that I send to just about everyone to embarrass him.

wesley-j--mathews_63_11-06-2024_150529: awesome. Somewhere, somewhere I read like you, you claim your brother was like smarter. He was like the smartest in

squadcaster-4b5h_1_11-06-2024_150529: Yeah, he is smarter. Yeah, he's smarter. He's the smarter brother. I would beat him in a fight in any sporting event though.

wesley-j--mathews_63_11-06-2024_150529: So take me back, like Moosejaw, like how, how did, how did you get involved and how did you have the idea to come up with this company?

squadcaster-4b5h_1_11-06-2024_150529: Yeah. So, um, you know, I didn't know what I was going to do with my life. And I was, I was taking backpacking trips out, uh, mostly school groups. And this is literally, this is [00:02:00] pre internet and we would go on some pretty serious trips. I was working as a guide for a friend of mine who had a guide service, along with another friend of mine, and these kids, they needed real gear and there were, there were very few places to get it.

So it sort of started off as a joke. We said, okay, let's, let's open a store. Uh, and we, we got really lucky for a couple of reasons. First, we, we opened a store. It was 1200 square feet. Which is not much bigger than the room that I'm sitting in right now. So it's tiny and a town called Keego Harbor, which you may know, but the larger audience may not, it's a little town in Michigan.

And, and at that time, it's hard to, it's hard to even, even think about it this way, people who bought this, this kind of, this kind of gear, they were actually going on a trip. Right? So North Face, for example, when we started did not make product for women. So if you think about those old, those, those North Face puffy jackets, right?

If you were a woman and you wanted one of those, and, and you were typically a woman's medium and you were just buying a men's [00:03:00] model, they'd North Face made one day pack. Now you can't walk around Michigan or Michigan state or any campus without seeing a million North Face book bags. Right? So we got really lucky with our timing.

We also got lucky because we had no idea what we were doing. So when. I say this, people think I'm being hyperbolic, but I'm not. This is, these stories are true that when people would come into our store, we, I didn't even know to say to them, can I help you? Like I was the kid who would not go to the mall with my mom.

And when people would come in, I would say, do you want to go play Home Run Derby in the parking lot? And we really had Home Run Derby set up in the parking lot. And Connecting with the customer in unique and interesting ways, which we did by accident, it wasn't a purposeful marketing campaign that resonated and people would used to come and hang out at our store and then stores.

And so we had a ping pong table in our stores because I love playing ping pong, right? And it was fun. So we would do that. Once we realized that [00:04:00] that was working, that engaging with the customer in unique ways, was driving traffic and sales. Then we started doing it purposefully. But, but at the beginning, we were doing it because we just wanted it to be fun.

wesley-j--mathews_63_11-06-2024_150529: how, how old are you at this time

squadcaster-4b5h_1_11-06-2024_150529: I was 21 when we started Moose Jaw.

wesley-j--mathews_63_11-06-2024_150529: what, what year, where's the internet in this?

squadcaster-4b5h_1_11-06-2024_150529: So we started Moose Jaw in 1992. We actually, um, we had our, our anniversary on Halloween. So we opened on Halloween in 92. And, and then, you know, I, I, I used to think that we were really lucky because I was closer in age to the demographic that we wanted to embrace. So college kids, and I also love technology.

So when the internet started to emerge, we were very, very early players. And that was also super helpful to us. I mean, we had Moosejaw. com, but there's a whole story behind it. We started off as [00:05:00] Moosejaw online. Because Moosejaw is actually a city in Canada and the city owned the name Moosejaw. com. We eventually bought it from them, which was a whole nother crazy story.

But, uh, we were, we were doing that in 95, which was very early.

wesley-j--mathews_63_11-06-2024_150529: you're young in your twenties, like, where do you go? Right. So the internet comes out and you know, you've got to buy a domain name and build a website

squadcaster-4b5h_1_11-06-2024_150529: Yeah,

wesley-j--mathews_63_11-06-2024_150529: and spin up an e commerce. I mean, so that wasn't even in your vantage point when you started the company, the internet didn't exist.

squadcaster-4b5h_1_11-06-2024_150529: right. Yeah, exactly. I mean, again, I'm a big believer in luck. We got really lucky. I was working. We had a store at that time at Michigan State and we had computer science kids working at our store and they knew how to do this shit. So we just collaborated and built the first, I literally can remember one of the people, they had a, uh, their family had a house in Gaylord and I literally can picture perfectly exactly where I was sitting.

We just, we went up north for a few days and designed the whole website, [00:06:00] right?

wesley-j--mathews_63_11-06-2024_150529: That's awesome.

squadcaster-4b5h_1_11-06-2024_150529: And so it was, you know, we had no idea what we were doing and just figured it out as we went along.

wesley-j--mathews_63_11-06-2024_150529: What happened from that point where you guys moved the company online? I mean, did you still have. That same type of culture, like the ping pong, that attitude, or was it, no, we're going to go shift our efforts online.

squadcaster-4b5h_1_11-06-2024_150529: No, it was, it was, we were, we very purposefully wanted to figure out how do we replicate this feeling and culture that we had in the stores to the internet. And so for us, we were doing things like blogging before there was a such word as blog, we were doing engagement before that was a buzzword. So for example, we were doing Moosejaw catalogs very early.

We never. just chose the cover. We would always go out to our community and say, okay, we're deciding one of these six covers, which do you like the best? And. And we genuinely wanted our community's opinion. So again, again, once we realized that this [00:07:00] was working, then we started doing all of that more intentionally.

wesley-j--mathews_63_11-06-2024_150529: So you eventually ended up selling this business. What, what year did you sell? That's

squadcaster-4b5h_1_11-06-2024_150529: So we raised money in 2010 and we sold to Walmart in 2017. So we went, I think this, this might be a little bit of believing my own bullshit, but I think sometimes, sometimes people think Moose Show was this overnight success story. We really weren't. I mean, we, We are, we were and are grinders. So this is, these stories, I mean, I have so many crazy stories that you wouldn't believe them, but when, when we started Moosejaw.

com, okay. The, we had an 800 number, wherever I went, whatever store I worked at, I would literally call the phone company in the morning and say, point the 800 number to our gross point store. And when I went to the gross point store to work that day, everyone had to pick up the phone and say MooseShow.

com, right? [00:08:00] And, and people were taking orders in the store. And then when, when I would go home at night and then my brother eventually took this over, we would literally bring the credit card machine home with us. We would point the 800 number to our house. So if you were calling Moose Jaw at 2 in the morning on a Saturday night, my brother was answering the phone in his bed, taking the order, pressing, pressing numbers into the credit card machine, sitting by his bed.

I mean, those are, those are real stories.

wesley-j--mathews_63_11-06-2024_150529: awesome.

squadcaster-4b5h_1_11-06-2024_150529: Yeah, it was fun. I mean, it was hard,

wesley-j--mathews_63_11-06-2024_150529: 2010, so what was, or why did you end up, what was the race for capital at that point? Like what direction were you going to go?

squadcaster-4b5h_1_11-06-2024_150529: So we, we really, I, I really fell in love with e commerce. Uh, I, I think we were, I love the stores. I was so maniacal and obsessed with brand and there was so much more control over the brand for us in e commerce than in the stores. So if you picture, let's just say we're [00:09:00] doing a promotion. Um, we, we were, we did, But just for a, for an easy example, um, free, get a, buy a Patagonia jacket and get a Patagonia water bottle, right?

Which we would do sort of in partnership with Patagonia and our stores, we would have to, we would have to make signs, right? And we would have to send the sign to all the stores. The people at the stores would have to take the sign. They would have to put them up in the right place. They would have to take it down and put it away and not ruin the sign so we could do it again.

That never worked once. Ever. Like, I don't know how retailers do it. We were terrible at it. But for the internet, for e commerce, those kind of campaigns were so much easier. Right? It was all automated. So I fell in love with the internet. We wanted to raise money and find a partner who could help us do more retail expansion.

So that was the primary catalyst to us raising money is we wanted to focus on the brand and e commerce and really have someone else take over retail.

wesley-j--mathews_63_11-06-2024_150529: So you [00:10:00] sound like, as you talk about Moosejaw, like I hear the passion.

squadcaster-4b5h_1_11-06-2024_150529: Yeah. Loved it.

wesley-j--mathews_63_11-06-2024_150529: all of it off to Walmart? Or like what, what led you to

squadcaster-4b5h_1_11-06-2024_150529: Yes.

wesley-j--mathews_63_11-06-2024_150529: Moosejaw away?

squadcaster-4b5h_1_11-06-2024_150529: Yeah. It was. Um, so I, at that time I was, I had started a second company called CrowdRise and I was on the board of Moosejaw and, and was part time there, but we had a different team running the company at the time and, and Walmart made sense as a partner. They were trying to compete with Amazon at the time and they made a bunch of acquisitions.

They bought Bonobos and they were actually, Awesome. Um, you know, I, I, at the time said, listen, I were acquired by Walmart. I'm good. I'm, I'm going to be done. And, and they were an amazing partner. They were really good. Now, now Walmart has since sold Moose Jaw to Dick's. Um, and, and that's a different story altogether that I probably shouldn't get into, but Walmart was great.[00:11:00]

They actually were.

wesley-j--mathews_63_11-06-2024_150529: think in your mind and starting this company as Moosejaw that you would end up partnering with, with Walmart?

squadcaster-4b5h_1_11-06-2024_150529: Fuck, no, no. I mean, still to this day, you know what? This is, um, I mean, this is sort of, I don't know if this story will make sense, but I, um, I remember perfectly our first thousand dollar day, right? The very first day that we did a thousand dollars in sales in a day and I couldn't believe it. Right. And I said to myself, I hope this feeling never goes away.

It actually did, right? That feeling went away, but even still today. If I'm at the airport in, in Denver or I was in, um, I was actually in Alabama, um, a few weeks ago and I saw a random person wear a Moosejaw hat, that feeling has never gone away. I still can't believe it. So it's, uh, you know, it was, we worked really, really hard, but we, we tried to do something, uh, tried to do something special.

Yes. [00:12:00] Uh, at Moosejaw.

wesley-j--mathews_63_11-06-2024_150529: so to speak, when Walmart, so did they, they approach you or were you actively looking to find a new partner?

squadcaster-4b5h_1_11-06-2024_150529: It was, it's a, it's a, it was more of a series of events, um, then, then it, which it usually is, right? Nothing, nothing is usually so straightforward. Um, but it was a, it was a long chain of events that led to that.

wesley-j--mathews_63_11-06-2024_150529: So how do you segue from a moose jaw from a company like that to go into, you said crowd rise,

squadcaster-4b5h_1_11-06-2024_150529: Yeah. CrowdRise was our second company. So, um, CrowdRise was a fundraising platform and we really wanted to have an impact. And, and do something special or, or, or unique and try and raise money for cause. But we didn't wanna do it in a normal way. We wanted to take these, these lessons from Moose Jaw and apply 'em to a new space.

And if you think about the giving space in 2010, it, it was actually tactless to tell people [00:13:00] how you gave back. Nobody did that. Nobody told anyone how they gave to charity. And now you can't scroll on social for more than 10 seconds. without seeing how someone gives to cause. And I think we played a small role in that.

So our goal was in the very, the very same way that our playbook at Moose Jaw was, how do we make this fun? Right? Backpackers and climbers take themselves very seriously. How do we make it fun? We took that to sort of the next level in the giving space. So to us, charity was defined as being burdensome and guilt ridden.

We wanted to flip it and make it fun and social. And the idea was that if you can actually get people to enjoy giving back, they'll do it. More frequently and tell their friends about it. So we were really crazy I mean our slogan was if you don't get back, no one will like you which was very polarizing I mean the first organization we met with was American Cancer Society and they Literally laughed us out of the room and then they said we will never do this Well, very lucky five years later when we became the conduit [00:14:00] to the way younger people were giving back Then we, we became American Cancer Society's fundraising platform.

So that really went full circle, but we, we, we worked really hard.

wesley-j--mathews_63_11-06-2024_150529: and this is also, so this is So like web is still like, cause I got into website design development back in like 2006, 2009. And still was really difficult to get really good software to get a good website done. So you're like first to the market on something like this. did you

squadcaster-4b5h_1_11-06-2024_150529: Yeah.

wesley-j--mathews_63_11-06-2024_150529: piece together a team?

Was it like people you knew or like, how did you, you know, have this vision and idea and actually make it come to fruition?

squadcaster-4b5h_1_11-06-2024_150529: So we, we actually, when we, when we had the idea, again, I, I said this before, I'm a big believer in luck. Um, we, I connected with a friend of mine who's an old friend of mine, her name's Shauna Robertson. So if you know all the Judd Apatow movies, for getting Sarah Marshall, Elf, Anchorman, Meet the Parents.

She, these are her movies, right? And she's just, she's an old [00:15:00] friend. And her boyfriend at the time was Edward Norton, the actor, Edward Norton. And Edward was running the New York Marathon to raise money for one of his causes. And I ended up talking to Shauna about this idea to find a new way to, to encourage people to give back.

And Edward grabbed the phone and said, Hey, I'm running the New York Marathon for one of my causes. This, there is no way to crowdfund in a, in a, a more modern approach to the space, a more fun approach to it. And so we collaborated on his, on his charity campaign. And I actually ended up We ran the, we ran the campaign together.

I ended up running the marathon with him and our goal was to raise 75, 000. And through these crazy ideas, we ended up raising 1. 2 million. And, and from that, we said, well, fuck, this is awesome. Let's take these lessons we learned from this small micro site that we built ourselves, and [00:16:00] then we said, okay, let's build this for all charities to be able to use and, and, and we, you know, we went out and hired people to help us do it.

wesley-j--mathews_63_11-06-2024_150529: So at that time, it's GoFundMe, the giant in the room, I mean, they had the massive platform or

squadcaster-4b5h_1_11-06-2024_150529: Not yet. That, that, um, GoFundMe came a little bit later. So the difference between CrowdRise and GoFundMe and why we, why we were able to eventually merge with them is GoFundMe started off where that you would raise money for your friends in need, right? And you couldn't do that on CrowdRise. You could only raise money for American Cancer Society, Red Cross, Unicef.

I mean, there's 2 million. US based nonprofits. So any of those 2 million you could raise money for, but you couldn't raise money for your friend. And that created pretty significant synergies between our two platforms. Uh,

wesley-j--mathews_63_11-06-2024_150529: like looking back with your experience with Moosejaw and Crownrise, you repeat those processes today [00:17:00] or is it like that, that time's past? With those specific companies.

squadcaster-4b5h_1_11-06-2024_150529: I don't know. I, I think it would be really, really hard again, in that you think about the timing we had for both companies. It was, it was really, um, It was the right time for both of those companies. I mean, we're certainly hoping that we have the right time for our new company, ZEC2, but I think it would be really challenging for a number of reasons to do the same thing we did today.

wesley-j--mathews_63_11-06-2024_150529: So as an entrepreneur, was your goal always to create, create, get it to a point and then get out of the way? Or like how far through your journey do you like to take companies? Yeah. Yeah. Yeah,

squadcaster-4b5h_1_11-06-2024_150529: I, I don't know. I saw, um, and, and, and, And the following person is a friend. So I don't want, I hope he doesn't listen to this cause I wouldn't want him to hear me say something nice about him. I, I love the startup side. I love the stress of it. And, and I love building a brand, but I saw the CEO of GoFundMe, GoFundMe is a big [00:18:00] company, and I saw how the CEO of GoFundMe, he's no longer, he's not the CEO anymore, his name's Rob Solomon.

And just saw the way he worked and the way he ran a bigger company. He was just better at it than me. And. I didn't really know that until I saw the way he operated. Um, so I'm not, if we're lucky enough at our third company to be a big company, maybe I'm the right person to run it. But, um, Rob would be, someone like Rob would be better at it.

I just saw the way he worked.

wesley-j--mathews_63_11-06-2024_150529: awesome. It's good to have humility as an, as an entrepreneur to be like, Hey, I'm not the best person for this job.

squadcaster-4b5h_1_11-06-2024_150529: Well, we, we never, the moment any of us think we know what we're doing, we're all in big trouble, um, at our company. Right. So we're, we're really grinding it out and trying to figure it out as we go along.

wesley-j--mathews_63_11-06-2024_150529: cool. Your partners with Ed Norton. I, I I've watched a ton of his movies and I actually use them as an example every now and again, cause I sold my last company and I

squadcaster-4b5h_1_11-06-2024_150529: huh. Yeah,

wesley-j--mathews_63_11-06-2024_150529: And I go, do you remember that scene in fight club? I think [00:19:00] it's Edward Norton's looking at that hotel that the guy set on fire. And he's like, somebody came up to him. They're like, yeah, fight club. And he's like, I didn't like, this wasn't my mission to create this. And my company kind of transformed into something that I didn't create. And it was, it just got kind of weird, but I always remember that

squadcaster-4b5h_1_11-06-2024_150529: no, that's awesome.

wesley-j--mathews_63_11-06-2024_150529: Um, so you guys sell that company to go fund me.

Are you so active in that company at all? Are you on the board or

squadcaster-4b5h_1_11-06-2024_150529: Not no. So Edward is, I'm not, I mean, I'm still, I'm still friends with so many people who work there and, and I'm, uh, you know, you and I have talked about sports a little bit. I love sports and I love cause. So, um, yeah. You know, when I'm not working on ZEK, 10, 000 hours a week, those are the two things that I tend to engage in.

So rarely does a day or certainly a few days go by where I'm not engaged in cause in some way and therefore still connecting with the people that GoFundMe and a lot of them worked at CrowdRise. So I'm still friends with them.

wesley-j--mathews_63_11-06-2024_150529: do you like, and I [00:20:00] already know the answer to this before I ask, but you've had two really great exits leading up to this point where you just mentioned, like I'm working 10, 000 hours. could probably stop working. Like, have you ever thought of that? Or have you actually tried to stop creating or like, what, where, like, how has that impacted you?

squadcaster-4b5h_1_11-06-2024_150529: I mean, I, I, I really would, I would wish me upon no one. Hope I can stop at some point But I'm a you know, I'm a terrible sleeper. I Not last night last night. I woke up in the middle of night for entirely different reasons, but the night before Um, I literally, I woke up at four in the morning and had an idea and I was like, all right, there's no chance I'm going back to bed.

And I just got started. Right. I just, that was it. So, um, yeah, but it's not, it's, that's stressful. You know, I, I've never, I've never taken a nap in my entire life.

wesley-j--mathews_63_11-06-2024_150529: So this leads you into ZEC and [00:21:00] ZEC is a, to make board meetings more efficient, more productive, which I've actually been on the board meeting side. And when I saw you're

squadcaster-4b5h_1_11-06-2024_150529: right.

wesley-j--mathews_63_11-06-2024_150529: about ZEC, I'm like, man, how much time did we spend on this really boring presentation to then send it out, to then regurgitate what somebody could just look at and just look at themselves?

Like, I just looked at that process, started laughing. Cause I'm like. It was a complete waste of time on my end.

squadcaster-4b5h_1_11-06-2024_150529: You've, you nailed it. I mean, we, um, we really did build ZEC based on our own experience. So between Moosejaw and CrowdRise, the shortest deck we ever sent to our board was 134 pages, which is crazy, right? We had no idea what we were doing. Uh, we spent 100, 150 hours as a team on these presentations and they were bad.

And then we would get into the meeting and quite literally, and we had these amazing sort of famous board members. I mean, one of our, one of our, our board members that, uh, at CrowdRise is now the U. S. ambassador to the Czech [00:22:00] Republic, right? I mean, we had some badasses on our board and we would get into the room and reread them.

On a 134 page deck that they had already read, right? So it was a waste of time for everyone. I genuinely thought that we were the only ones who were bad at it. It wasn't until after our companies were acquired and sort of got out there in the world that I realized this angst was universal and couldn't believe there wasn't a solution.

So it was our, our, our team, I could tell the whole long story, but our team basically got back together. And we started a couple years ago, and so that's where we're spending, uh, all our waking hours now.

wesley-j--mathews_63_11-06-2024_150529: You have team members from BoostJaw and CrowdRise.

squadcaster-4b5h_1_11-06-2024_150529: Yeah, so, so, my brother, uh, and Edward Norton, the three of us started ZEC together, and We have our, basically our COO and head of product has worked at both Moosejaw and CrowdRise. Our head of sales was our head of sales at CrowdRise and GoFundMe. The [00:23:00] person who runs brand ran brand at CrowdRise and Moosejaw.

So it's, again, super, super lucky. We already sort of speak each other's languages and it, you know, can end each other's sentences from day one. Nobody had to learn all that.

wesley-j--mathews_63_11-06-2024_150529: So is ZEK then, is it, is it like a SaaS platform? Like a monthly

squadcaster-4b5h_1_11-06-2024_150529: Yes.

wesley-j--mathews_63_11-06-2024_150529: for like, is it entrepreneurial companies? Is it mainly enterprise level companies or all the above or?

squadcaster-4b5h_1_11-06-2024_150529: Yeah. It's really any company that has a board and what was unexpected. It's so there's 2 million us nonprofits. They are mandated to have board meetings. So let's just say at a minimum, they have four board meetings a year. So that's 8 million board meetings and they're all bad, right? So we didn't expect nonprofit to also be a customer, but about a quarter of our customers are nonprofits.

And that was totally unexpected.

wesley-j--mathews_63_11-06-2024_150529: Wow. So systems built. What's the goal for ZEK? Where, where do you, where do you go from here? What's the,

squadcaster-4b5h_1_11-06-2024_150529: You know, we're really trying to, and again, we're not, I don't want to pretend we're saving the world, but we are, we do think we're doing [00:24:00] something transformational. I mean, literally, I am, I am certain that none of the work you do, or, or your listeners, you're not signing, um, documents with ink and sending a FedEx package with those little tabs anymore, right?

You're using DocuSign. Yet, we're not. For our board meetings, we insist on using slide decks, which were quite literally built pre iPhone. I mean, go try to read a deck on your phone. You can't do it. It's impossible. Try to collaborate with it. It's impossible. So we're trying to modernize that process in the, and this might be an unfair analogy, but for lack of a better one, in the same way that DocuSign has modernized the way we sign things.

So that's what we're trying to do and build a brand around it. So part of it is, again, there's this through line from Moosejaw to CrowdRise to ZEC. We think we're, we're in this space that is miserable, right? There's nothing more miserable or stressful than the board meeting and we're trying to make it fun.

So I literally, I, right before I got on this call, [00:25:00] we sent cookies to companies prior to their board meetings to ZEC companies. And one of the cookies says, uh, It says, eat this or whip it at an unproductive board member. Right. And a PE company that takes themselves very seriously just sent me a picture of their cookies that we just sent to them.

And they signed one of the cookies saying, you know, thanks so much. A few people on the team, like, that's fine. You know, we try and make it fun. So that's, that's what we're trying to do is really build a brand around this transformation.

wesley-j--mathews_63_11-06-2024_150529: So what, what's next? Are you, as an entrepreneur, are you, what are your thoughts around AI? You know, what's, what's

squadcaster-4b5h_1_11-06-2024_150529: We're

wesley-j--mathews_63_11-06-2024_150529: project?

squadcaster-4b5h_1_11-06-2024_150529: super into it. The, the, so. We, we have really pressed AI to be a part of the product and it is, it is actually mind blowing. So, uh, it really, the way we describe it is it turns you from an author to an editor. So just for example, we have a, we, we have a monthly all hands for our company and it usually takes everyone on the team, including me, [00:26:00] a couple hours to put your section together.

With AI, it probably took me eight minutes. And it was better than anything I could have done myself. So I actually think Zach is a really nice use case for AI because we've built it specifically for executives and it surfaces the information that an executive would care about most. It works. It's, it's really cool.

And we're just getting started.

wesley-j--mathews_63_11-06-2024_150529: That's really cool. I'm a, you know, so I'm a visionary entrepreneur. I'm too, I wait until the last minute to do things. And I had a presentation in front of a group of entrepreneurs. If he's listening, I apologize in advance, but I had to do, and I literally went to Prezi, a presentation platform, and I built my presentation and I want to say like, yeah, five minutes.

squadcaster-4b5h_1_11-06-2024_150529: Right.

wesley-j--mathews_63_11-06-2024_150529: downloaded my persona to chat GPT and loaded up all this like, I couldn't believe it. So when I showed my

squadcaster-4b5h_1_11-06-2024_150529: Yeah,

wesley-j--mathews_63_11-06-2024_150529: like, Oh my gosh, you actually did something in it. And I'm like, it took me like five

squadcaster-4b5h_1_11-06-2024_150529: that's amazing.

wesley-j--mathews_63_11-06-2024_150529: really

squadcaster-4b5h_1_11-06-2024_150529: Right.

wesley-j--mathews_63_11-06-2024_150529: this is actually

squadcaster-4b5h_1_11-06-2024_150529: [00:27:00] Yeah.

wesley-j--mathews_63_11-06-2024_150529: like thinking about 2009 or 2010. Like it would have taken me weeks or like, I wouldn't have been able to get that done. It's just amazing at how fast things are changing.

squadcaster-4b5h_1_11-06-2024_150529: Yeah. You know, where we, where we've had to spend a lot of time is on the security. So if you think about board meetings and investor updates, the, if you go in and we, the backbone of our AI is chat GPT. Uh, but. If you put something in chat GPT, it goes out into the universe. So board, you can't use that for board meetings.

So we've spent a lot of time on security in order to make the AI secure because that's table stakes at Zach. So a little different than some of the other solutions out there in terms of compliance. So we've been through due diligence hell with our AI with some of the big companies that use Zach and it's, we passed all tests.

wesley-j--mathews_63_11-06-2024_150529: How do you, as an entrepreneur and like your success with the last three companies and what you're doing today. Like just the workforce in general, like are you, you live in [00:28:00] Michigan? Uh,

squadcaster-4b5h_1_11-06-2024_150529: Yeah.

wesley-j--mathews_63_11-06-2024_150529: assuming these companies are, they're not bound to a specific state, but you guys are all over the place, manage teams throughout the country.

How do you, what's, what do you see today? And for the future for employees or like working for your organization? Like how, how drastically different is that from your original days at. CrowdRise, and BoostJaw.

squadcaster-4b5h_1_11-06-2024_150529: You know what, it's, it's, it's definitely different, but because we had multiple locations and allowed, and also allowed people to work remotely at CrowdRise, there was, in our conference rooms, there were, at the time, there was no Zoom, but there were Google Hangouts was what it was. Every, you couldn't go in where there weren't multiple Google Hangouts happening.

So, we were sort of used to Zoom. That kind of world. And now, obviously being in room and you could just yell to everybody, Hey, come check this out is, is different, but I think we've embraced it pretty nicely. I don't know if you all use Slack, but Slack has become a big part of what we do. [00:29:00] And we, And we are relentless about building systems to make it fun.

So I'll give you just one example of something we're doing right now. I mean, we have very few rules at our company and we've had the same rules at all three companies, but one of them is no yawning. Okay. And so we're very big on coffee and espresso. So we have a contest right now and it's to, it's for a, for a fancy espresso machine and So everyone is entered into a contest, but when we pull a name from a randomizer, it's you're out of the contest, right?

So, so it's great. It's really mean and so, uh, in a fun way. So on our all hands the other day, you know, we pulled a couple names and they were out of the contest. And we're doing, I don't know if you do any of the New York Times games like Wordle or Connections, but we're all doing all that stuff all the time for prizes.

So we try and make it fun. And again, very lucky that people on our team worked at Mooshong CrowdRise, so [00:30:00] they sort of know how we like to do this. I mean, it's not that they know, they built it along with us. So they, you know, they were on the ground.

wesley-j--mathews_63_11-06-2024_150529: So is ZachThat, complete virtual company?

squadcaster-4b5h_1_11-06-2024_150529: Yeah, we're entirely remote. So we have 23 people on the team right now, and they're everywhere. So, um, you know, my, you forget about the, some of the. Some of the stuff you have to deal with as a company that's just not fun. And one of them is getting the tax information from each different state where there are employees and my brother deals with all that.

So I, it gives me great pleasure. Every, I probably have one right here. Yeah. State of Pennsylvania, right? For every time something comes in. To send it to my brother. So he has to deal with it. So basically when we have a new hire, he just says, we can't get a new state, right? Yeah. I can't take dealing with yet another state documents.

wesley-j--mathews_63_11-06-2024_150529: [00:31:00] hear that. I am definitely not the operations side either. Uh, so we got, before we go, we got to talk about this, the, the break dancing and the, uh,

squadcaster-4b5h_1_11-06-2024_150529: Yeah.

wesley-j--mathews_63_11-06-2024_150529: where, where does that come from? Is that your brother

squadcaster-4b5h_1_11-06-2024_150529: And we just, we just want to make it, we're just want to be crazy and make it fun. I mean, and, and, and, Anything to be different, but not take it too far is sort of where we sit. So at Moosejaw and CrowdRise and Zach, in terms of how far we press the brand, we always say, we can talk about French kissing. We can't talk about fucking, right?

That's sort of, that's sort of our mindset. Like we, we want it to be fun and foolish, but we don't want to make anybody mad, right? So, um, But we're doing stuff like that all the time. And we just emailed our customers yesterday, just literally with a movie quote and said, guess the movie for a chance to win a Zach hoodie.

Right. And we don't even have Zach hoodies. We will literally going to, we are [00:32:00] going to make our first Zach hoodie for the winner, and that was part of the messaging. So we just want it to be fun.

wesley-j--mathews_63_11-06-2024_150529: well, I love that. That's, you know, here you are with a handful of companies, super successful. You're sending stuff out and you're still building. I like to use the analogy of like building the plane when it's flying kind of a deal. Like

squadcaster-4b5h_1_11-06-2024_150529: Yeah, for sure.

wesley-j--mathews_63_11-06-2024_150529: out and you're like, we even have the hoodies.

Like you're just going for it. That's awesome. That

squadcaster-4b5h_1_11-06-2024_150529: Yeah. You know what? It's interesting. You use that analogy. I think, and we talk about this. At Moosejaw, and certainly at the beginning of CrowdRise, we were flying the plane and didn't know where it was going to land. And it's, I think it's really hard to run a company that way. You know, we would just literally go from crisis to crisis.

I think we've done a better job creating systems so that at least we have a destination, right? We, we, we, we have goals and we know where we want to go and, and we're hell bent on hitting those goals as opposed to Just going from project to project, which is really hard. I mean, we do that also, but at least we have, uh, we have more paper goals in [00:33:00] mind, which, and then you back into them and figure out, okay, do we have the resources to hit these goals?

And if you don't, then let's either get the resources or change the goals. So we really try to not live in fantasy land as we operate the company.

wesley-j--mathews_63_11-06-2024_150529: Did you pull from like an operating system? Like there's, there's a ton of them out there. Is there anything that you

squadcaster-4b5h_1_11-06-2024_150529: Yeah.

wesley-j--mathews_63_11-06-2024_150529: an entrepreneurial perspective or not really?

squadcaster-4b5h_1_11-06-2024_150529: Just all our failures. I mean, we literally, we failed at everything. And again, lucky to be working with the same group. So we've lived this together. And so it's really, it's, it's really our own system.

wesley-j--mathews_63_11-06-2024_150529: That is, that is something special. I think like my last company to my new company, like my partner and I are both, Back. And it's kind of nice.

squadcaster-4b5h_1_11-06-2024_150529: Yeah.

wesley-j--mathews_63_11-06-2024_150529: things, right. Or like something's going wrong. We kind of look at each other and laugh because like, we've been down that path.

squadcaster-4b5h_1_11-06-2024_150529: Oh, we get, I mean, our head of sales and I were on a call with a normal person, a customer who we didn't know a couple of weeks ago, and we got the giggles on the call. It [00:34:00] was inappropriate. It was like, we literally, I could, I had to take a post it note and put it over my, his name's Trey, put it over my friend's face on the zoom.

Cause I couldn't look at him. Like that stuff is, you know, it's great.

wesley-j--mathews_63_11-06-2024_150529: That's awesome. if anybody listening, like how, what's the process of getting involved with Zach? I know a million companies right now that I think go through

squadcaster-4b5h_1_11-06-2024_150529: Yeah.

wesley-j--mathews_63_11-06-2024_150529: And honestly, until I met you, I didn't even know that there was a solution that solved this problem. Like, know,

squadcaster-4b5h_1_11-06-2024_150529: Thank you.

wesley-j--mathews_63_11-06-2024_150529: how do people get in contact with it if they want a demo or they want to, you know, give it a test run?

Cause I think it's a, it sounds like a really an amazing solution for a lot of companies.

squadcaster-4b5h_1_11-06-2024_150529: Yeah. Thanks. I mean, just go to zec. app, Z E C K dot app and you can, you can get on a demo. You probably get one today if you want. Our team is awesome. They're fun. They get, they understand the problem, uh, and we make it really easy. One of our, one of our goals is to make the process easy. So it's, you know, I, I'm sure you've purchased a lot of software.[00:35:00]

There was nothing more frustrating to me than getting on a call with someone like me. And they say, Hey, this is, it's unlimited and you get the contract and you find out it's unlimited for three people for the next three weeks. And then they start upselling you like crazy. We're not like that. Again, we're trying to do something very different here.

And so ease of use is something that we're pretty relentless about.

wesley-j--mathews_63_11-06-2024_150529: That's awesome. That sounds super exciting. Well, Rob, thank you so much. I know you're a super busy guy,

squadcaster-4b5h_1_11-06-2024_150529: Thank you.

wesley-j--mathews_63_11-06-2024_150529: got some ideas.

squadcaster-4b5h_1_11-06-2024_150529: You are too.

wesley-j--mathews_63_11-06-2024_150529: I want to get out of your way there, but thanks so much for coming on and sharing your wisdom. I really appreciate it.

squadcaster-4b5h_1_11-06-2024_150529: Yeah. Thank you so much. Appreciate it.

Outro: This has been another episode of Entrepreneur Intel. Thank you for joining us. For show notes or other episodes, please visit us at entrepreneurintel. com. Until next time.