#199: John Knific (Squad) — The EdTech Guru

John Knific [00:00:00]:
My whole career, it's been important to me to sort of be a part of that hacker hustler duo to tie this into the work we're doing at k two Venture Partners as well. I believe Chris and I can build just about anything. And Wiser built my confidence back up with a successful exit to sort of know I have these go to market shops that are really unique. A successful exit to sort of know I have these go to market chops that are really unique. In launching Squad, what took millions of dollars at Decision Desk and then took a single million dollars at Wiser for $2.50 ks or less, me, Chris, an engineer, and AI are able to ship the same level of product and software.

Jeffrey Stern [00:00:38]:
Welcome to the lay of the land podcast where we are exploring what people are building in Cleveland and throughout Northeast Ohio. I am your host, Jeffrey Stern. And today, I had the real pleasure of speaking with John Knifick, serial entrepreneur and investor who has built three venture backed software companies here in Cleveland. His latest venture, Squad, is a peer discovery platform designed to gamify ratings and rankings for Gen z, starting on college campuses, delivering valuable preference data to marketers. Prior to Squad, John cofounded Wiser, a virtual communities platform that transformed how universities engage with students. Wiser ultimately served about 1,000,000 active users before being acquired by the Education Advisory Board, EAB, and Vista Equity in 02/2021. For those interested in diving deeper into Wiser's story, I'd recommend checking out episode 35 of Lay of the Land where Kate Volzer, one of John's cofounders, shared her perspective on their journey. John's entrepreneurial journey began with Decision Desk, a company which he started out of his dorm room as a student at Case Western Reserve University when he was still on a music and pre medicine track, and ultimately raised 6,000,000 in venture funding for.

Jeffrey Stern [00:01:55]:
Today, alongside Building Squad, John is also the cofounder of k two Venture Partners, where he and Chris Ciccarello, his other cofounder from Wiser, invest in and advise regional startups. In our conversation, we'll cover how John has evolved as a founder, his philosophy on product management and go to market strategy, the intersection of jazz and entrepreneurship, opportunities in education and in edtech, building for enterprises versus building for consumers, mentorship, and lots more lessons learned from his journey across three startups. Please enjoy this awesome conversation with John Knifick.

John Knific [00:02:33]:
Lay of

Jeffrey Stern [00:02:34]:
the Land is brought to you by Impact Architects and by ninety. As we share the stories of entrepreneurs building incredible organizations in Cleveland and throughout Northeast Ohio, Impact Architects has helped hundreds of those leaders, many of whom we have heard from as guests on this very podcast, realize their own visions and build these great organizations. Organizations. I believe in Impact Architects and the people behind it so much that I have actually joined them personally in their mission to help leaders gain focus, align together, and thrive by doing what they love. If you two are trying to build great, Impact Architects is offering to sit down with you for a free consultation or provide a free trial through 90, the software platform that helps teams build great companies. If you're interested in learning more about partnering with Impact Architects or by leveraging 90 to power your own business, please go to ia.layoftheland.fm. The link will also be in our show notes. I'm always thinking about where the the best plate to start these conversations are, and I had a few ideas for for ours today.

Jeffrey Stern [00:03:40]:
But in in the spirit of what we were just talking about, I am curious as to what you see as the overlap between jazz and entrepreneurship.

John Knific [00:03:51]:
Jazz and entrepreneurship. I guess that, yeah, that encapsulates my upbringing and what I do now in a big way. Okay. So let me think about this. There's a there's a lot of overlap. So the foundation of jazz is having some sense of song structure, but being able to improvise and figure out where the boundaries are, where you can push them. And what I think it's really interesting. If we think about the team sport of entrepreneurship, when you are playing together in a jazz band, the more you play together as a group, the more you can kind of mind read one another.

John Knific [00:04:34]:
You can experiment, you can stretch those boundaries, but still find yourself with a north star for what you want things to sound like, where you want them to end up. And I've always been a huge proponent of having great co founders. I think this is entrepreneurship is a team sport. And to some extent, when you really understand your co founders strengths, weaknesses, where you empower each other, it's a very similar feeling to and it's been a minute since I've actually been on a stage, but it's a very similar feeling when you are just dialed in in a groove, almost floating on top of the music versus it feeling forced figuring it out awkward. Right? So I think I don't know. We could we could spend the whole hour talking about that. Yeah.

Jeffrey Stern [00:05:21]:
It's I kinda love that you you opened with that because I I always find myself fascinated by entrepreneurs who go for it a second time, let alone a third time as their career evolves like yours has. Because one of the patterns that I pick up on from from founders is that it's kind of like one of the perennial trite but true things. But if they knew what they know now, they likely wouldn't have set out to build, you know, what they did knowing the Herculean challenge that that it entailed at the time. Yeah. But those who have opted to dive back in, I think, speaks to a certain kind of internal drive and motivation that that is interesting. But I hadn't thought so much about the cofounder chemistry as, like, a a way to make serial entrepreneurship easier.

John Knific [00:06:10]:
Yeah. And there I mean, there are plenty of founders I deeply respect who like the sort of route to it. For me, it's I have to be building things. I have to be solving problems. I mean, this is technically my third venture backed company.

Jeffrey Stern [00:06:26]:
Yeah.

John Knific [00:06:26]:
And I've been starting them literally since college. And before that, I had little businesses in middle school and high school and early the the crazy part crazy part about my background is my first real job was after being acquired by Vista Equity and Education Advisory Board at Wiser and landed at EAB in an executive product management role reporting to, like, the head of the division. And I remember in our first meeting, I was like, I don't wanna make this weird, but you're my first boss. So for me, it's it's less I don't know that it was ever conscious. And, actually, to tie it back to to music, Yeah. The people who go into music and are successful have to be entrepreneurial. Right? They are by they are creative. They are builders.

John Knific [00:07:18]:
They have to put a lot of pieces together to make a career out of it. The ones who almost can't think of doing anything else because they are so passionate about it are the ones who actually make it. And I do think there is that overlap in building companies. To some extent, it's glorified, but it is very painful. Right? There are many there are many low points. There are many points where you have to really figure things out. You have to zoom out. You have to fire people.

John Knific [00:07:47]:
You have to go cut your own salary, all all these things that you would never conceive of doing working for a company. But I think the key similarity there is you. I never think about a world where I wouldn't be where I wouldn't be doing that. You know what I mean? Yeah. Yeah.

Jeffrey Stern [00:08:04]:
I am. Do you so you always felt that you kinda had this entrepreneurial drive and and inclination?

John Knific [00:08:10]:
Yeah. I guess to to tie it to my kind of the, you know, start of my story, I always loved doing lots of different things. Didn't really know what I wanted to be, but in high school I was doing music. I was learning to code. I was building websites. I was building PCs. I was doing, you know, nerd and creative and all of the all of the above. But I ended up kind of deciding, okay.

John Knific [00:08:35]:
Well, a lot of the the smart kids around me say they they wanna be doctors. I had an I I have an uncle who is a radiologist, so I, applied to a bunch of schools premed, but I I tried to find schools that had a good music program at the same time. So I could kind of do both kinda mentally keep the options open. And so Case Western is ultimately where I ended up. My dad's side of the family is from Cleveland, but I, I grew up in Michigan. And I, I came to Case because they let me into med school at 18. It was this pre professional scholars program was what they called it. Basically, you have to keep your grades really high, but you don't have to take the MCATs.

John Knific [00:09:16]:
You get to go to CaseMed when you, when you graduate which was an incredible value proposition. And on top of that got almost a full ride because I had a music scholarship with that. So it just, it became a no brainer choice. Like I'm going to case that was in 02/2005. I'm in Cleveland. The irony of that is knowing I had been accepted. I started to try more things. I ended up picking up an entrepreneur minor entrepreneurship minor at case.

John Knific [00:09:45]:
Got really interested in just kind of obsessed with this was the early web two point o movement. So all these early apps coming out, you think about the kind of six, seven, eight, nine class of y combinator, all those prolific, you know, the Airbnbs. Like, all these prolific companies are coming out. YouTube is new. Facebook is new. And I just looked at that and said, I don't know how, but I just wanna be a part of that. And so I started what became my first venture, my senior year at Case. And I remember calling the med school and saying, I have to decline this acceptance and they were totally befuddled because like, nobody does that.

John Knific [00:10:26]:
Like, it's a golden ticket. But for me, it was a huge weight off my shoulders. Like I'm going to go and run it something I'm passionate about. Not just something that's hard for the sake of being hard. Like instead of this sort of pre carved pat, you know, seeing this pre carved path in life, this idea of being a doctor, is something I kept kind of I put in my own head as may you know, this is, like, a thing that you should do. And as soon as I open myself to what could I build, I mean, that's when I really found what I love to do. Well, tell

Jeffrey Stern [00:11:02]:
us about the decision desk chat.

John Knific [00:11:05]:
Yeah. So just for a little bit of context, decision desk started that my senior year at Case. This was 02/2008, graduated in 02/2009. The startup ecosystem here in Cleveland was pretty fresh. So at that time, North Coast Ventures, right, was just getting started. They were in fund one. There were some kind of pitch competitions, things like that, but all the stuff for us Cleveland locals, we know about case, like think box, etcetera. None of that stuff existed.

John Knific [00:11:36]:
And so decision desks started as basically a virtual audition product. So I took that kind of love of music and realized that most schools, if you're applying to a music school, you mail a physical DVD, you burn a DVD and you mail it. And I'm looking at streaming video and saying, well, that seems a lot easier. Cofounded this with two other case grads. We built the self hosted transcoder that could do HD, which was a little novel at the time in the sense that HD was a little more expensive. Basically put a form on top of it, a login on top of it, and I started selling it to universities. And that was without me knowing it, kind of my entry point into EdTech, my entry point into SaaS. I remember my first sale, walked in, found a button, found a button down shirt.

John Knific [00:12:29]:
I'm in college, walked into the cli the Cleveland Institute of Music and had this meeting. And I said, well, how do you guys handle your auditions today? They walked me into a room that was literally wall to wall with DVDs and bins that they physically handed out to faculty. And I remember saying, well, what if we just digitize this whole thing for you? What would that be worth? They're like, I mean, well, that'd be incredible. How much would that cost? And not knowing anything. The best thing you do as an entrepreneur, I learned is just ask more questions. So I said, well, what do you do today? Do you charge your students to apply? And they're like, oh, well, we charge a $30 fee to mail these. I said, well, what if we split it with you? And what I didn't realize was that was a thousand dollar contract I had just booked because of the volume that they were getting. And we just rinse, repeated, stacked more music schools.

John Knific [00:13:19]:
At that time I started to connect with some of the early software startup movers in town, like super grateful for, you know, Todd Federman. He had very recently kind of helped create North Coast. Charlie Stack was very involved at that time. And those guys, you know, I came back around to kind of being involved in cases entrepreneurial programming, but it just, there wasn't as much there at the time. So it was really the community leaders who helped bring me up, show me the ropes. And the funny part is a lot of us were were learning together. There were not many SAS startups at that time, so we were all kind of figuring it out. Yeah.

John Knific [00:13:58]:
That was the origin story of decision desk.

Jeffrey Stern [00:14:01]:
Yeah. But it and it just came to mind, and I feel like I would be remiss if I if I didn't ask about it in the, in the spirit and in honor of of Bob Sopko. I I did wanna ask about, you know, his role in in your journey and, you know, what what you take as lessons from the opportunity to have worked with Bob?

John Knific [00:14:20]:
I'm happy you you mentioned that. I met Bob about a year into starting that venture. He was also kind of early in his career at Case, and he actually introduced me to, Lev Gonic, who at the time was the CIO of case and Lev joined our board and he eventually became the CIO of Arizona state. So one of the most powerful dudes in ed tech. I didn't know what I was doing. I was a kid. But I've just made these connections and kind of forged. And I we've we see everyone writing these stories, which is honestly so beautiful.

John Knific [00:14:54]:
Cause I think we all, until you see the volume of just goodwill, it's staggering in the onesies, twosies you feel. It's like, oh, he must have just really liked me. It's like, no. This is just who I mean, sure he liked me, but that's just who he was. That's just who he was. You know what I mean? Yeah. So yeah. Bob Bob through thick and thin for me personally was a champion because there there were low I mean, we can get into it, but there were lowlights and highlights to to this entrepreneurial journey I I've had.

John Knific [00:15:25]:
And Bob would always show up and be a champion every step of the way.

Jeffrey Stern [00:15:30]:
We'll ground it maybe in in EdTech as a theme. But I'm curious what about the intersection of technology and education was interesting and exciting to you? What were the problems that you were interested in exploring? Obviously, decision desk made way for what you built and and and worked on with Wiser. What was it about that space that, you know, had such a gravity to it for you?

John Knific [00:15:53]:
There are a few things. So I I've didn't mention this, but both my parents were college faculty members. So I had grown up being around educators, colleges, my my entire life. It was really that it was interesting that multimedia music angle that kind of tripped me into ed tech. It wasn't maybe as intentional as, I could I could pretend it was. What was interesting though, is in building things for universities, you know, the hardest part was always the sales cycle, getting in, building those relationships. It's very political. It's a very matrix complicated sale, but once you're in, they're really willing to try stuff.

John Knific [00:16:31]:
These are like very long term multi year relationships. And as a sandbox for me to learn how to build products, build software and cut my teeth and sort of B2B to see where I could interact with students on the app side, but work on solving really bigger picture issues around, like, retention, enrollment, advancement. Like, I've I've had roles in in software at all those components of a university. To me, that was really interesting. I was able to learn a lot and build really great products, build great companies. And as we talk about that making way for for Wiser without going into the the full story, decision desk, just decision desk got tricky at the point where we were a beautiful vertical SaaS product, but we started to really get beat up from the larger CRM vendors who just kind of encapsulated what we did in a larger solution. We kind of orchestrated a soft landing for that company, but around that time, kind of towards the tail end of it, I brought in Kate Boser, who as you well know, became my co founder at Wiser. Candidly, I had this chip on my shoulder from decision desk not being a huge success in the end, especially since it kind of was an early success and then had some trouble along the way.

John Knific [00:17:49]:
And I felt like I had those battle scars that understanding how to ship product, sell into that space. And Kate brought a, an element to it that I didn't have what she had been on the inside of universities. She had worked in admissions at the university of Chicago. She had her MBA from Chicago booth and candidly, she just was a trailblazer networker. I've always been a little more introspective. Like how do we find product market fit? How do we carve out these channels? She gets out there, kicks down doors. And I basically knew after a few conversations with her, we, if we picked what we were going to do, we would make a successful ed tech company. It almost didn't matter where an ed tech we, we would build a successful company.

John Knific [00:18:31]:
And so we actually literally got out the napkin, like literally over drinks and we drafted up what the first version of Wiser would be, which started out in mentorship. Didn't end there, but started out in in mentorship. And the missing component, again, without going too far into it, a lot of the challenges with decision desk more so so towards the end came from not having great technical leadership. And so I knew I needed we needed someone as an equal cofounder who was incredible at architecting software and someone we could really trust. And that's where, I had known Chris Ciccarello in the community for for a while. We've it was timed really well where he came in as an equal third cofounder, and we started on the the journey together. And as we'll probably talk about, you know, Chris and I now have a software studio together, and and we're cofounders in this third venture. I guess from from those those lemons at the end of decision desk, we made the lemonade with Wiser.

Jeffrey Stern [00:19:35]:
Yeah. Well and I I think, you know, now having kinda laid the foundation for those those three chapters with decision desk, Wiser, and and what you're you're working on now. I mean, one of the things in the spirit of this kind of serial entrepreneurship and getting back into the the arena is because I you I think you've begun to touch on some of them, but, like, what you've taken with you at each stage that you've brought with you to the subsequent undertaking and just kinda the most salient lessons learned along the way.

John Knific [00:20:05]:
Yeah. Well, there's I mean, that's a big topic. So the first thing let's tie it back. One of the biggest lessons learned and I'll tie it back to kind of your first question in us talking about co founders. I believe strongly the team at the beginning has to be able to ship and sell. If that founding team can't do that, I don't care who you hire. You're not going to be successful or at least not nearly as successful as you you could be. And with Wiser, we did raise a seed round.

John Knific [00:20:39]:
We raised we re I I'm actually spacing on the number, but about a million bucks to start signed contracts shipped. We hit a rough patch where the product market fit wasn't as strong as we had hoped selling into alumni relations offices, but we saw a beacon for how we could sell into enrollment again, which by the way, that was another, that's another huge takeaway. In B2B, there's only really three value propositions. You can save people time, save people money, or make people money. And you want to be in the, the latter part of that. Right. So when it, when it came to wiser's narrative around that, we realized we were saving people more time than making them money, which is when we pivoted to enrollment. The tough part about that part of the story was we had to cut the team down.

John Knific [00:21:27]:
That included actually firing some some close friends who were working with us at the time. But the key difference between that experience and the decision desk experience is we didn't raise a dollar more capital. Basically the three of us, plus a couple additional employees reshipped the software, refocus it on enrollment and ultimately grew it to almost a million in ARR with a team of five before we started stacking hires again. And had it not been the three of us with that skillset, it would have been a much tougher situation. And then if we think about carrying that into the newest venture squad, I've always been my whole career, it's been important to me to sort of be a part of that hacker hustler duo. And this might sound, I promise, I don't say this to be pretentious, but to tie this into the work we're doing at k two venture partners as well. I believe Chris and I can build just about anything and figure out just about anything. And Wiser built my confidence back up with a successful exit to sort of know I have I have these go to market chops that are really unique.

John Knific [00:22:40]:
And so in launching Squad, what took millions of dollars at Decision Desk and then took a single million dollars at Wiser for two fifty ks or less me, Chris, an engineer and AI are able to ship the same level of product and software as what we were doing at wiser. So a lot of the playbook has remained the same, but it's gotten sharpened, sharpened with each venture. A lot of it just execution and pattern recognition, but also kind of knowing what's important and what's not important.

Jeffrey Stern [00:23:12]:
That's a pretty fascinating paradigm also because it, I think, kinda just is is true of the technological trend of what used to require millions of dollars in start up capital. Yeah. Like, multitudes of employees and years to reach market scale can now be accomplished with thousands of dollars and a handful of employees and a shortened time horizon, and that's just like the technological leverage at its best that you have to do.

John Knific [00:23:39]:
A %. Yeah. That's where what what Chris and I are doing with k two is really realizing that by having our skill sets and amazing tech enablement, whether it's spinning out our own ideas like Squad or working with a founder who's trying to figure out product market fit, the money required to do this is infinitely less than it used to be, And you can move the needle really, really quickly. So the whole notion of what a studio can be and how you can be testing and spinning up these apps and even multiple companies would have been unfathomable of well, a decade ago. Like, decision desk era, the thought of spinning up and testing multiple apps at once just sounds absurd. But I think it's actually I think it's actually required now because the moat is so much shallower. You need speed. You need momentum.

John Knific [00:24:42]:
You need multiple irons in the fire to be successful. So so, yeah, same playbook, but it's it's sped up a lot since since venture one.

Jeffrey Stern [00:24:50]:
Yeah. The the way I've I've kinda thought about that, velocity piece and and the the time it takes to bring these ideas to market is that before where you would be testing the ideas that you have, now I I feel like it it allows you to focus a bit more on the quality, of the ideas. Agreed. Which is just it's just pretty fascinating. I think it'll unlock a lot for, hopefully, all of us going forward.

John Knific [00:25:17]:
Yeah. Totally. It's, some people find it scary, but I've I've found it. I've I've candidly found it incredible. It unlocks so much potential. For example, I'm not really a coder. I I play a designer on TV. I can operate Figma and I've created plenty of landing pages and all that.

John Knific [00:25:36]:
But, you know, with our use of like, we use anthropic heavily. We use Claude heavily. I'm able to help spin up front ends, applicable prototypes, sorts of things that if we connect the dots to the past ventures, you would have teams to do. You would hire you'd outsource marketing firms. Right? So I I think for the entrepreneurs who like to roll up their sleeves, figure stuff out, you can get way deeper into product market fit before thinking about spending lots of money on a concept. Money should unlock. And that's always been the case. Money should unlock scale.

John Knific [00:26:12]:
You should use as little money as possible in the figuring shit out stage. You should use it the most when you're pouring gasoline on something that's working. And I just think that that's been enable been enabled more and more.

Jeffrey Stern [00:26:25]:
So I wanna take a brief moment to unpack your first job, if you will, which was, you know, as as an employee of the company that had acquired Wiser. Yeah. And knowing that you've since departed and and what we'll get to squad and and k two. But I I am curious what you kinda took from having a a job and a role and what that transition was like. When you reflect on on Wiser's story, how is that transition and and what was it like having a a job?

John Knific [00:26:54]:
It's a good question. I am a better founder than I am an employee. I'll start there. The folks at EAB, which was our acquiring company, could not have been better to the team and the founding team. They gave us a lot of latitude. They gave us a lot of opportunity within the organization. Work life balance, which was a is a word that I hadn't quite understood yet was very real there. My wife and I had our third child while I was at EAB and I took many weeks of paternity and, came back and the team welcomed me back.

John Knific [00:27:30]:
It was just, there was a lot of decompression that happened after running those two startups so tightly back to back from a emotional standpoint, that was important to me. From a work standpoint, I learned that I need to personally be working on the entire end to end from what we are going to ship to how we are going to distribute it, to how we're going to retain and support it. And there were many incredible team members at EAB, but at that time and I think they've solved some of this between having lots of rapid acquisitions. They were converting from a heavy services organization into more of a product organization. There were just there's a lot of silos and kudos to the people who can do this, but the skillset to navigate those silos and help move a larger organization forward is a, it is a different skillset than the one of founding a company and taking it from zero to one and one to two. So there was a part of me going in that didn't know what to expect. Maybe I'd like it. Maybe I'd like being a product lead somewhere, like, right, a big awakening.

John Knific [00:28:42]:
But it only reinforced I remember being at the end of year two. I I this is maybe not the best move, but Chris and I quit on the same day at at UNED. Kate also quit very shortly after that. It was it was less so like, oh, we're excited to go start start something. It was like, we have to go start something. Like, we are we are we are going, we are going to go now.

Jeffrey Stern [00:29:08]:
Right. And with that comes a bit of exploration, the development of k two, ultimately squad. I, I mean, with the world as your oyster, basically at that point Yeah. How did you you know, what was the compass that was guiding you to figure out what to work on on next?

John Knific [00:29:25]:
That's a big one to unpack. I think there's for founders who have a successful exit, the figuring out what to do next, it's an interesting conundrum because there's almost like an analysis paralysis because there's so many ideas you could pursue. Now we have a little bit of capital. There's some cache. What do I do? What Chris and I ended up doing that was honestly incredibly helpful was we set up a series of frameworks based on our he he's got even more experience than I do, but combined almost thirty years of product go to market software experience and a half dozen startups between the two of us. We put together a set of frameworks for how we would evaluate and test ideas. And we would use that as a mirror for our own ideas, but also kind of get, get sharp by working on other people's ideas too. And so what came out of that was this framework we call blueprint, and it's basically a mechanism to narrow a set of buyers, use cases, value proposition, and have something immediately testable within twenty four hours.

John Knific [00:30:37]:
And you can't just sit there with no idea and lever it. The point is if you have an idea you've been picking at, it's basically a giant magnifying glass to kind of sharpen it and hone it into into the next kind of the next few steps. So that is something we continue to do for other startups. Now how that factored into squad, I'm wearing a squad t shirt. This is where Mitch Kroll enters the picture. So another Cleveland character. So I grabbed coffee with Mitch through an introduction and shared my story. We got along really well.

John Knific [00:31:11]:
He's he's also a musician. He's a drummer. I don't know if he talked about that in your show. I told him the story and. A a a bullet point really stuck with him, which I mentioned we had almost a million users, student users in our app by the time we were acquired. And he was sort of like, holy shit. And he's like, how big were is it? Or how big were you guys? And I was like, yeah. It's just like handful of people.

John Knific [00:31:36]:
And he was like, is it true if I say you are really good at getting college students signed up for products and apps? And I said, yes. And he said, maybe you were fatigued for a minute and it kind of like from the education, but think bigger. And that's, that was the big Mitch thing that lent itself really well in parallel with the way Chris and I work with our kind of very pragmatic strategic thinking was zoom out. Think a little bit bigger. And so what we started picking at was what were the parts of Wiser that really hooked students and got them excited to use the app. And the part that really hooked them was if you are coming into a school for the first time, you're very open to new things and you're very eager to learn. And you're very eager for a sense of belonging, all things that traditional social media kind of suck at. One of the most powerful things we had going at Wiser now the funny part was Wiser was sold to the school as a way for incoming freshmen to connect with upperclassmen.

John Knific [00:32:43]:
It turned out and the reason we were worth a good bit of money was if, incoming or prospective student used wiser, they were four times more likely to enroll in that school because they felt a sense of connection. So that was like the, the B2B value prop. But the consumer value prop was that if you have been at a school for a while, you have all this amazing tacit knowledge of the culture, clubs, the best professors, the best happy hour. Like these things sound trivial, but it is literally your entire world when you're going into college as this like new formed adult. So we basically picked at that emotional job. And I think that's kind of the key difference in a learning curve for us doing consumer versus strict b to b. You're solving an emotional job a little less than that sort of enrollment functional job. And so, you know, we I can talk more about what the Squad app is and and what we're doing, but it was that think bigger, build something that could actually scale to millions and millions of users.

John Knific [00:33:53]:
And we took sort of that hook we learned from Wiser, took the dash of inspiration from Mitch to go big or go home, and then kind of apply our pragmatic lens of the k two, and that's how Squad came out.

Jeffrey Stern [00:34:08]:
I love that. I I guess the the way I would frame this question is if one of the takeaways from decision desk and Wiser was this learning that enterprise businesses you can frame in this way of saving money, saving time, growing revenue, what have you come to be able to articulate about what that looks like, you know, with this? You kinda mentioned the emotional problem, but, like, what does that look like in consumer? How do you think about the higher level problem to be solved with consumer? And and then, yeah, I would love to just hear about, you know, where has Squatter come to at this point?

John Knific [00:34:44]:
Yeah. So I'll start very philosophical, and then we'll talk practical about what we're building, why it's valuable. So hanging on that transition point into college and to some extent transition point out of college equally important. There's a couple key turning points there that people are very open to trying new things, particularly new apps that we're you were, you know, leveraging. When we talk about consumer needs, talking about Maslow's hierarchy stuff, like love, friendship, belonging, for consumer apps, that's really, really important. And we live in an attention economy. Look at how ad dollars are spent. Look at the growth of social media spending the growth of influencer ad spending.

John Knific [00:35:27]:
Social media is the internet for young people. They are in those apps way more than they're in a browser. So you have to take that context for that. There's, like, a trillion dollars of ad spend at stake thinking about where the puck is going there. So it's with that lens, Chris and I basically said, how can we take what we're good at deliver something that actually creates good in a sense of belonging, but carves out a really meaningful set of eyeballs. That would be incredibly valuable if we were actually able to scale. And so the squad app is basically a community app for college campuses. And we've created this unique mechanic that we call a pick.

John Knific [00:36:14]:
So early Twitter is a tweet, early Facebook, the wall. We created something called a pick. Basically every day we prompt a really interesting question that's basically rating and ranking different things. Whether it's best taco on campus to which of these five pairs of shoes is the cutest to which of these professors gives the most interesting lecture. And what happens when you vote on that is it reveals what other people think, which is a natural human instinct. You wanna see what your friends think. You wanna see what other people think compared to your opinion. But we're actually crowdsourcing thousands, hopefully, eventually millions of data points to create these preference graphs and leaderboards around brands, around places, around things.

John Knific [00:37:03]:
And with each pick, you basically it's almost I mean, I think we can be a Yelp killer if we do this right. It creates this overlay of campus of what to do, who to connect with, things like that. But the scale strategy is that each of those picks generates an SEO optimized landing page. So over time, if I were to Google what's the best taco at OSU, you can actually you'll hit the page, click on it. It'll pull you through to the app. And that's also thanks to AI, right, that we can automatically spin up those types of things. So that nugget of I wanna log in as a new freshman and figure out campus is the itch we're scratching, but it's that mechanic of kind of casting your vote and seeing what other people thinks that generates its flywheel. And for us on the cons you ask the difference between enterprise and consumer.

John Knific [00:38:01]:
In enterprise, I would have sold that we're going to do this, And then we go like create a scope of work and figure it out. For consumer, we actually shipped four versions of this app over the past year to cohorts of 50 to a hundred students to test and test until the mechanic actually worked and we saw the daily usage. And it's then, and only then that we said, okay, we have something we're going to launch. And so basically, this January, we've got a target set of about 300,000 students on 10 very large campuses. And the go to market is that same ambassador strategy. I've now 32 paid marketing interns on those campuses driving that initial content set. But basically, that we're gonna kick off the flywheel and see how things go.

Jeffrey Stern [00:38:46]:
We mentioned that the go to market chops, you know, that you've kind of honed over over your career now both internally and and working with other founders. What is it it practically look like to build that 300 k student network in advance of launch, the on the ground campus ambassadors? What what does that actually look like?

John Knific [00:39:04]:
It's a good question. So that is a bit of, like, a, I feel, kind of a secret sauce that we took with us from some of our experience at WISER. People this is true of everyone, not just students. People love to feel like an expert. If you ask someone for money, most of the time, they say no or why. If you ask them for expertise, they're very willing to give their expertise. It makes them feel good. It makes them feel like they're giving.

John Knific [00:39:35]:
So to tie that to this ambassador model, I basically ran, a really aggressive recruiting campaign for students interested in entrepreneurship and marketing who are very social and a part of lots of different clubs. And I asked them lots. I kind of created this systematic interview. I actually got the interview down to seventeen minutes to basically figure out will they be successful in this role, which is willing to put themselves out there, share opinions and invite people. And we have some really amazing students. It's incredible. We did our first all hands where I had all 30 of these students on a video call at the same time. Yeah.

John Knific [00:40:13]:
And the ideas, they basically feel self they feel like this is their app, and they're self empowered to promote it. I have some that are creating picks and then printing out QR codes for each pick and, like, plastering them on bars. I have some who are befriending RAs at schools and making it, like, part of the introduction to campus. So that go to market hack is creating that sense of ownership, giving them the tools to be successful, and then being there for them to kind of help support that launch. The app itself has to work. It has to retain people. It has to be fun. It has to have utility.

John Knific [00:40:54]:
But the kind of levering that distribution channel is is mission critical. So for me, since with the launch coming up, that's kind of the main priority on the squad side is is making sure those ambassadors are successful.

Jeffrey Stern [00:41:08]:
What what does success look like for you in this context and kinda writ large? Is it a rendered obsolescence of Yelp or, you know, what is what is the impact that you are hoping to drive here?

John Knific [00:41:19]:
Well, you know, Jeffrey, three out of four people on Yelp are over the age of 35. So it's rendered itself obsolete. I'm just kidding.

Jeffrey Stern [00:41:25]:
I'm I'm

John Knific [00:41:26]:
kidding. Success for me is the same as always that people love the product. If people love the product a lot will take care of itself. That's way easier said than done, obviously. From a, where I want this to go. If you look at my history of decision desk being maybe barely a single to, Wiser being like a double, maybe a triple. I want this to scale to every campus in the country and basically have a household brand social app. And the part of me that maybe this is the crazy part, you look to kind of the Instagram success stories.

John Knific [00:42:03]:
I want that to be a team of eight people in Cleveland. Like I don't care about the venture capital aspect. I don't care about a, I care about the scale, the value and doing it with as small a team as possible. So for me, that would be the greatest win. What are you most excited about looking forward? For squad or personally, or? Yeah. Both then. Why not? I'm really revved up about 2025, personally. Decision desk into Wiser back to back, that was, like, a twelve year twelve year slog.

John Knific [00:42:41]:
Weiser is obviously successful. Two years of decompression at EAB. I feel like Chris and I have dialed in something really incredible at K2 where we know how to spin up, validate these products. And I hope that we get to work with more startups. That's part of keeping ourselves sharp. We learn a lot, continuing to work with other entrepreneurs. The fact that we've been sort of under the water building this thing for the past year, clearly it's been in front of people. We've been testing the heck out of it, but I've haven't been posting a lot about it.

John Knific [00:43:14]:
I don't talk a lot to other people about it. Been talking to a lot of college students twenty two. Like next year, it becomes real. For almost twenty days in a row, we're launching large 20 to 30,000 person campuses with kind of a rapid succession, rapid plan after that to continue scaling. All that becomes real next month. So like for me, coming out of this build period, going into the launch period, I know you know this feeling because it's a very unique feeling in a startup to go from the talk about it to its live, and that's what we're about that's what we're about to do.

Jeffrey Stern [00:43:46]:
With regards to and I like the way you kinda framed it as staying sharp from the k two perspective. Yeah. What what what have you kinda taken from working with other founders who are building their own ideas and trying to to bring those to fruition about that zero to one phase and thinking writ large, the the product management philosophy? And sometimes it's easier to recognize the the lessons and learnings with other people than than it is in yourself. So I'm curious, like, what you've learned from others that you had in in, like, self reflection.

John Knific [00:44:19]:
Maybe most elegantly put, it's the greatest form of knowing is teaching. And I, I love working with college entrepreneurs in particular. I mean, I was one and I feel grateful in that sort of pay forward aspect. What's neat about putting the energy into something more specific like k two and that, you know, the the blueprint workshop that we do is we can have a really deep level of impact, but also we have to think through a problem, help figure out a go to market, help figure out how to test it. And that's always, I mean, it's opening up neural pathways for us too. We are teaching the practices between the two of us. We've seen a lot, but we learn, we come away learning something new. And sometimes it's a vertical that we're not going to tackle right away.

John Knific [00:45:12]:
But man, the pattern recognition, it starts to become very real because at the end of the day, it's, there has to be a great hook to a product, a value prop and a great traction channel. And the more you start to see those patterns, when we come back to the venture we're working on, you never know what's gonna unlock something interesting.

Jeffrey Stern [00:45:35]:
If if one of the learnings for Mitch Kroll is, how do you elevate the bar of ambition and think bigger? What are other lessons you've taken away from from working with Mitch and also from from working with with Chris?

John Knific [00:45:48]:
It's a great question. Yeah. But, I mean, both Mitch and Mitch and Chris are candidly I I consider them mentors even though they're business partners. For Mitch, Mitch is never afraid to question and hold a mirror up to things like the think bigger. He can tell almost instantaneously when you're too far in the weeds and that you need to put something down and zoom back out. And no matter how much you, I talk that talk about the importance of zooming out when you're actually the one building something, it's really hard not to get in the weeds. Actually, you have to be in, you have to be in the weeds to be successful. So Mitch is a great influence on us to be that checkpoint as someone who's been at it longer than us, even more pattern recognition.

John Knific [00:46:36]:
And you want people like that around who have seen the patterns, been the founder, been the one in the hot seat to kind of call things as they see them. Things I've learned from Chris, man, he's taught me basically what it means to run a great product organization. Just in terms of how to think about building great software, why you're going to build great software. I felt like before working with him, you'd fall for a lot of the, like, what's trendy, what's cool in tech, people throwing around the jargon. Like, Chris is kind of this old school aspect to it. It always comes back to like, what's the smallest thing we can build to delight the user. How do we build it in a way that's not going to screw us over later and how are we going to measure if it's working or not? Now we both kind of mind lock around that way of thinking, and that's ultimately, I think, why we've been successful as a team.

Jeffrey Stern [00:47:31]:
You you had mentioned the, call it, mason c of the Cleveland entrepreneurial scene when you were getting started at decision desk and how the the cohort, if you will, of of companies building at that time were trying to figure it out, working together through it. What what have been your reflections on kind of the evolution of Cleveland entrepreneurship and and the role Cleveland has in in in your journey?

John Knific [00:47:54]:
Yeah. I think the people here really care to see fellow entrepreneurs be successful. There are more entrepreneurs here now, but I I won't sugarcoat it. Like we still don't have great density. I think there's there's a comradery there in people actually willing to fight the good fight and try to build something from scratch. And we, you brought up Bob Socko earlier. It's people like that that literally make all the difference. So I learned from people like that.

John Knific [00:48:28]:
You want to be one of those people, because if you're in this position doing this for the first time, you really need all the help you can get. You're gonna make a shitload of mistakes. That people energy is the most important part. I think from a from, like, a capital and a density, there's a lot of wood to chop still. Like, love the the role you're now playing with Ohio Fund. I think there are people trying to really make a difference there in terms of just the infrastructure and the opportunities to bring some some scale to things. But, you know, what's what's neat is why I'm ultimately very optimistic is okay. Yes.

John Knific [00:49:11]:
Maybe we have we've had certain density issues, but all the reasons why Chris and I and two fifty k of our own investment can build what I think is a world class company, that bar is so much lower than it was ten years ago. Yeah. And so it's really getting more of these smart people together to learn and share and trade knowledge. And I think it's become much less dependent on capital. It's about the, it's about the skillset. And to some extent it always has been. But now when we talk about the most powerful thing we can do, it's keeping kids here from college. I mean, it's it's small, but our first hire at squad is an awesome young engineer who just graduated case.

John Knific [00:50:02]:
He had a job waiting for him back in New York City. He's from Jersey at Capital One. And I talked him into doing the crazy thing, which is staying in Cleveland and pay him well and all that. But like, you gotta be a little crazy to take that job. And he took it and he's learning a shitload from Chris. I hope he's learning a lot from me. And yes, that's only one person, but like that building block of keeping the people here, that's gonna make a much bigger difference than any, I think, any other influencer can.

Jeffrey Stern [00:50:34]:
That piece is is critically important. It it just is. And we think just need a lot lot more of it to transpire, but I I assure your optimism. I I think it's the the barrier to entrepreneurship has never been lower, and especially to do it at scale and with a quality of product that that, again, just used to require a lot more. Yeah. What what's your what's your sense on on how they instill this way of thinking more? How do you get the entrepreneurs thinking more about how to leverage AI and kinda just the the the technology stack of the day more?

John Knific [00:51:13]:
Well, I'll I'll pull something that is something else I learned a lot from from Chris is you just gotta ship. Not to make it so simple, but you ship something, get someone to try and use something. You're gonna learn a lot. And this is the same as anything. You you have to go out there and make some mistakes. And if you're young and you've never shipped anything before, like, this is the greatest time in the world to do that. I mean, that's the, you know, the downside of the AI tools is you can make a big mess very fast. That is the fast is the operative word with AI.

John Knific [00:51:51]:
It'll be fast, whether it's the right answer or the wrong answer. But if the goal is to ship, iterate, learn, like, you kidding me? This is an incredible time to be doing that. But that's the gap. That's the gap. Like, sitting there thinking about things versus shipping and getting someone to trying to just drive some freaking value. Right?

Jeffrey Stern [00:52:12]:
Right.

John Knific [00:52:12]:
Help

Jeffrey Stern [00:52:13]:
that that that's that's what I was getting at, but articulated much better when I was getting at the the quality of the idea. Because I I think really what it does is it lets you understand much earlier if your idea is bad.

John Knific [00:52:25]:
There you go. Yeah. Exactly. Yeah. Because who knows if an I mean, ideas I've thought are super stupid have been very successful. Yeah. It's it's in the execution for sure. To tie it back to to some of the frameworks Chris and I have used to work with other startups, Our goal is always to get someone in a spot where they can go out there and actually try selling it.

John Knific [00:52:44]:
At the end of the day, that's actually the outcome we're driving at. We've, we've worked with really established companies and like brand new college founders and the ubiquitous thing where we can have the most impact is when they've just literally been in their head for way too long and they have to, they gotta put something out there. They gotta go test, even if it's wrong. I think this this step that's worth helping people unlock.

Jeffrey Stern [00:53:11]:
That that. Yeah. That's where the rubber hits the road.

John Knific [00:53:14]:
For sure. For sure.

Jeffrey Stern [00:53:16]:
So I think we'll we'll bookended here, with some closing questions. But before we get to that, I'll I'll post kind of the the greenfield one, which is what do you wish I had asked you about? Is there something particularly salient in in reflecting on your journey that that you would like to express or think is important?

John Knific [00:53:35]:
I think you you asked I not not to quote, Will Ferrell in, the movie where he's like, I blacked out. What did I say? I would say, you know what? I'll take it to an interesting place, which maybe relates it to Cleveland. Because one thing entrepreneurs, we don't talk about enough is sort of the importance of friends and family and support. And sometimes I'll be, I'll be honest. I can be dark on Cleveland from like an entrepreneur standpoint for the very reasons why it's tricky. You have to get on a plane sometimes to get things done. But to counteract that, like I met my wife here. She's an incredible partner.

John Knific [00:54:18]:
She happens to also be in, in tech where we have three amazing kids. And as much as these, these startup missions can feel all consuming and hard and all of that, just to know I made the choice to stay in Cleveland. We got married. We've I focus a ton of energy on family, and this is truly an amazing place to raise a family. Like, our quality of life, the multiplier effect, like, the the proceeds from our exit, what we can do here versus if I was in Manhattan or San Francisco or Austin. So just to tie it to kind of the, you know, the theme of this being a Cleveland based pod, we shouldn't always fake that this is some incredible startup ecosystem sometimes. I think it can be it's okay that it has drawbacks because the pluses live on another side that give energy back to the entrepreneur. And I know for me, having an awesome family, knowing I'm supported, that's what makes the bad days better and the great days even greater.

Jeffrey Stern [00:55:31]:
Yeah. Well said. Yeah. I mean, we kinda have to live in in, the reality of of what it is to to be here. And it's no it's no use trying to, like, fabricate some alternative version of it, and we gotta just lean into the the strengths of it. And and, yep. Well said. Well, I'll ask then, our traditional closing question, which is for a hidden gem

John Knific [00:55:52]:
in Cleveland. Something other folks may not know about, but they should. I will admit to seeing the question in advance and giving it some thought. And I am who I am, so I think in in bullet points of three, so I'm going to give you give you three. One is not hidden, but I always forget how incredible Severance Hall and our orchestra is. And we splurged for some box seats for the Christmas show tomorrow that we're taking the whole family to. And I'm always like, man, why am I not going to this more? Like it competes with every orchestra in the, in the world. Legit.

John Knific [00:56:33]:
Right. That's not like a, just like Cleveland pride thing. Like it's real. So that's a number one, number two for those who aren't west siders, Tartine bistro in Rocky River. It's an awesome little French bistro. They went through a rough patch with some ownership change, but they're, they're kicking butt again. I have really awesome memories of this because when my wife and I were, were first dating, this was literally fifteen years ago. And I was, I didn't make a salary from decision desk.

John Knific [00:57:02]:
You could get a wood fired pizza and a carafe of Bordeaux for $28 there. That price has increased a lot, but

Jeffrey Stern [00:57:08]:
I have

John Knific [00:57:10]:
but I have such fond memories. And then my last one is more of a shout out. This one's definitely a hidden gem, the old Coventry Theater on Coventry next to the grog shop. So I've got a buddy. His name's Joel Negus. He has the insane vision of it becoming a world class soundstage for doing a film scoring production. And he's actually willing it into being. So he, he and a group renovated the theater into being this beautiful acoustically perfect space.

John Knific [00:57:41]:
And they don't do a lot of public concerts, but occasionally they're hosting events there to record amazing live music. And it's a really unique experience. So, yeah, his name is Joel Negus and his group is called Cleveland Scoring. But if you have a chance to just find a random show, like, they're recording string quartets, chamber groups all the time. It's just a very neat, intimate space, and all the gear is there where they're doing literally, like, I I I think he's on the the path to being Grammy production artist, but I'm kind of watching it unfold, and that's happening here in our backyard,

Jeffrey Stern [00:58:16]:
which is neat. That's amazing. Those are those are fantastic.

John Knific [00:58:19]:
Well, John,

Jeffrey Stern [00:58:19]:
I just wanna thank you for coming on, sharing your story. Re really appreciate you you taking the time.

John Knific [00:58:25]:
Thanks, Jeffrey. Appreciate

Jeffrey Stern [00:58:27]:
it. If if folks had anything they wanted to follow-up with you about, what would be the the best way for them to do so?

John Knific [00:58:34]:
I'll put my personal email out there, John.Kniffick@Gmail, and I try my best to keep on top of LinkedIn. So those are two pretty easy places to find me.

Jeffrey Stern [00:58:44]:
Awesome. And then, quick rapid fire. Who who's your favorite jazz musician?

John Knific [00:58:49]:
Oh, man. Through the poker room, you probably can't see Bill Evans on piano. It's probably my favorite.

Jeffrey Stern [00:58:55]:
Got it. I was just curious there.

John Knific [00:58:57]:
Yeah. Cool. Thanks again, John. Awesome. Alright. See you.

Jeffrey Stern [00:59:05]:
That's all for this week. Thank you for listening. We'd love to hear your thoughts on today's show. So if you have any feedback, please send over an email to jeffrey@layoftheland.fm or find us on Twitter at pod lay of the land or @sternfa,jefe. If you or someone you know would make a good guest for our show, please reach out as well and let us know. And if you enjoy the podcast, please subscribe and leave a review on iTunes or on your preferred podcast player. Your support goes a long way to help us spread the word and continue to bring the Cleveland Founders and builders we love having on the show. We'll be back here next week at the same time to map more of the land.

Jeffrey Stern [00:59:42]:
The Lay of the Land podcast was developed in collaboration with the UP Company, LLC. At the time of this recording, unless otherwise indicated, we do not own equity or other financial interests in the company which appear on the show. All opinions expressed by podcast participants are solely their own and do not reflect the opinions of any entity which employs us. This podcast is for informational purposes only and should not be relied upon as a basis for investment decisions. Thank you for listening, and we'll talk to you next week.