Jeffery: Welcome to supporters fund ask an investor I’m your host Jeffery Potvin let’s please welcome Carey Ransom managing director at bank Tech Ventures founder at operate as our investor for today welcome Carrie it’s a real pleasure having you join us.

Carey: Thanks for having me it’s great to be here

Jeffery: Brilliant I’m super excited to chat with care we’ve chatted a few times over the better part of the last year and there’s been so much amazing stuff that I’ve got to learn from you and the things that you’ve shared and so I’m excited to kind of dive into this and break this all apart and I’ve got some really specific questions because you’re doing something that not a lot of investors do which is this whole Venture Studio world so I’m really excited to kind of dive in and learn about that and help the audience learn more about where all these pieces fit in this early stage ecosystem I’d like to start the way we like to kick our show off is that we want to allow you to share your background and you can go back to the school side the family business all these great things share a little bit about yourself and and what you guys have been up to and then one thing about you that nobody would know.

Carey: Well Jeffrey thank you and you know you mentioned the Venture Studio I think going back in time is probably what led me to why I’m doing what I’m doing and how I’m doing it today and so you know for me it goes back to growing up in a 100 year old family business and I started working when I was really young partly because I was curious about you know what did my dad do what did my grandpa do every day and what we had this local retail business that had been multi-generationally in my family and it was really what brought our whole family together so in a in a world that is probably becoming and continues to become increasingly less tribal that was kind of the the clan that that I grew up in and it was where I would say a lot of my early learning came from about how to treat other people how to think about the interplay and and dynamics of the community and we were in this little self-contained town that at that point in time it weirdly was was starting to to change in that it probably wasn’t quite big enough for the world that was growing around it and the expectations that people had from what a community or or the world could give them but it was this really interesting almost laboratory as I look back at it that I got to experience and also try a lot of things I I got to work with a lot of different people I get to see the value of Education because a lot of them were not as well read or well educated as I quickly became even as I got through high school and I’m so grateful to my parents because they exposed me we traveled quite a bit when I was a kid and they exposed me to this larger world and just between that and I was a voracious reader it just unlocked me and I I was this really curious kid always asking people questions and ultimately that led me to say I have to go get to a bigger Pond somewhere I went to a big school and part of that was just to challenge myself and say you know can I compete in a in a bigger place and I was pretty successful there and then I found myself in a big city and wanted to see you know could I survive in the in the big city and I ended up in Chicago and very shortly after that because I started in an industry I started in the consumer products industry which was somewhat comfortable because I’d kind of grown up in a in a world where we were moving consumer products through our retail family business but I was just always intrigued by technology and I’d had a computer in my house as a young kid and I tinkered a little bit with programming and basic which will date me but I I finally said you know what I need to go make this really a part of what I do and so in the mid 90s I talked my way into a software company and got a job in a software company and realized okay this is where I need to be and so if you look now across the last you know almost 30 years my life has been primarily in and around technology companies and you know I’ve done eight startups that I have joined from either founding or really early team or coming in as as a really early executive and you know I’ve had that entrepreneur and founder mindset and I know we’ll talk more about that and I kind of look at it as you can have that whether you were there at the drawing board when the idea was conceived or not but I have a lot of of life learnings now in in the rearview mirror that really inform where I go as we look ahead and you know it’s things like company building as a team sport and I want to be you know a part of teams that are going to have high conflict High interaction to try to find the opportunities and the best ideas and do that quickly and that informs a lot of how I look at investing today and so it’s been just an incredible journey I’ve had some amazing successes I’ve had some miserable failures and it’s just been a a really fun journey to be on and primarily what drives me is this continued curiosity to understand how things work today how they might work better and how to incorporate new and emerging ideas that are coming from Humanity on how to do things better that just continues to propel our world forward and so I feel such a privilege to be able to be out on closer to the front edge of that with how you apply a lot of these new technologies and new ideas to problems that can be better solved because of them and so about three years ago I walked out of my last operating role in a startup I was CEO of a Neo bank which many of your audience are probably familiar with these non-bank uh startups and we scaled it really fast and you know became a unicorn and I put a lot of new team in place and said you know this I think is my last full-time operating role and from here on out I feel like serial entrepreneur serial startup involvement is probably the best way for me to apply all these experiences and and skills and so that led to starting what ultimately became operate which is our version of Adventure studio and it’s different from every other Venture Studio out there and I think what I learned in the process was you meet one Venture Studio you meet one Venture studio and there are a lot of things that are like that and there really isn’t a singular way that those work and we said look we’re operators my partner and I both have built a lot of companies and learned a lot we said we’d love to work with early Founders and if we can put our experience and capability and some Capital with some early Founders we think we can help e-force multipliers on a bunch of other companies propelling forward that’s how we’ll do it and we’ll treat each one as a creative Outlet for us and and the founders and we don’t have a singular model in how it works and so that’s you know our version and we we can talk more about that and then you know just quickly to close off on Bank Tech Ventures which is a a new fund that I helped with some Partners launch and uh now manage about a year and a half ago we are really there I call it an industry ecosystem Consortium fund where we’re a strategic investor for the future of an industry and in this case it’s Community Banking and we are out looking for entrepreneurs who want to help digitize and transform and help make Community Banks more competitive and relevant in the years to come and we invest on behalf of just over a hundred Community Banks which we look at as a proxy for the whole industry to find those companies that can be meaningfully impactful to them and our team is comprised of both people who are out meeting those entrepreneurs and looking at are these good Investments that we should be making as well as an equal sized part of the team that focuses on how to help bring those entrepreneurs to the banks and help the banks understand how to incorporate them and benefit from them so we really have sort of a two-pronged team.

Jeffery: That’s pretty cool uh fantastic background and of course being able to share that you’ve got eight startups under your belt but not only that lots of Investments lots of advisory side so you really have taken a real deep dive approach I’d say it’s pretty agnostic as well it’s not hyper focused in one sector so there’s a ton of different learnings that you’ve gained or before

Carey: I know very little about a lot

Jeffery: which is great too that I think all those little things help challenge you to keep pushing forward right the what you don’t know you wanna your curiosity is going to pick you to get into so I I think it’s a a real cool tool belt of different learnings now when you when you take it back just before we dive in one thing about you that nobody would know I have to kind of get that out there it’s always a fan fave.

Carey: So I I you know that’s a that’s a good one I’ve often used the the family business um that you know I I grew up in uh that my dad sold four years ago and it was 146 years old so it almost made it to 150 years old in my family it still runs it’s just now owned by someone else the you know the thing that uh I I probably say that you know very few people know about me is I I really consider myself a geek in that I uh I just love so many different topics of uh information and like if you looked at the podcast that I listened to or the things that I read it’s just so vast and so I I think you know I tend to talk to people about things that they have interest in find the common ground with them but I have so many different spectrums of content topics that I’m interested in that I think that’s probably the thing that I I don’t tend to share with people they you know they probably think I’m I I read and I’m interested in things mostly like them because that’s usually what I talk to them about but I have a lot of other topics that I probably never cover with them because it’s not obvious that it would make sense to so um and maybe there are other people like that but I don’t think most people see that as obvious about me with you know the things that I put on social media or or ended up talking to most people about.

Jeffery: I think that’s awesome because when you when you dive into it as a generalist you’re able to look at and blend in well with a startup that’s sharing or pitching a business model and by the end of the conversation they’re looking at like you’ve already invested and you’ve been building this company with them for the better part of the last three to five years even though it’s only been half an hour talking to them so I I think that’s an incredible skill and it does come from being able to blend across the table and say hey you know what there’s similarities here or I’ve read a lot on this topic and I can kind of help you feel more comfortable about what you’re trying to build and I think that brings a lot of value to Founders even though they may not realize it at the beginning they’re going to be attached to it right away because again life’s tough no matter how you skin the cat it’s even tougher when you’re trying to build a company that people can’t understand that’s right.

Carey: I do fine I mean it’s it almost scares me at times Jeffries that I do find at times that uh Founders go wow you know a lot more about this than I thought you did and I and I kind of say to myself I don’t really know that much but you know I I’ve at least I’m at least a little bit familiar with it but sometimes they just get excited because maybe this is one out of ten people they’ve talked to who actually knows the the language and and some of the Dynamics of of this area and I go now I’m going to be over my skis really fast if if I have to go much farther so I’ve even at times said you know maybe my best attribute is I’m a good plane ride friend because I could sit next to somebody on a plane and probably have a conversation with them for the length of the plane ride but then I might be in trouble after that.

Jeffery: uh well hopefully uh it’s a short plane ride so then you have something to pick up on later but I think it’s a great skill honestly I think it’s helpful and having that operational background really does help other people kind of better understand even their own business once they have someone that’s coming in from with that outside objective uh view I think it really can change the way someone you know projects forward and what they’re doing so I think it carries a lot of value and I kind of wanted to go back and kind of peel back on a few things that you mentioned and um and I find it really fascinating because she utilize the your real when you first started working in your family business you realized that it was becoming less tribal and what I I love about that is that in all of our previous podcasts there’s been I would say an underlying tone that life when you’re Building forward something you need to find your tribe and it is so common that we do want to find that tribe and that could be from anything from school religion Sports there’s always a tribe that you’re trying to figure out where you fit in and especially this is really key when you’re building your first company is finding people that are like-minded that understand what you’re doing from investors to employees all the way through uh Founders and you saying that this was becoming less tribal but then it sounds like all the things you went forward doing was very tribal yes so does that less tribal mean that you were looking at this as maybe this business is going to transition at some point it’s not doing the things that I see it wanting to do and I have to go find the tribe where I’m going to fit in better and accomplish that is that a fair way of breaking that down.

Carey: I think absolutely in that case uh and I think some of it is you know just the societal definition of tribe if you go back in human history and it was very much familial for a long time and you had you know inbreeding literally and I think as uh as we’ve moved into a more uh educated and even to some extent independent Western societies that have influenced you know much of the world now I think the definition of tribe has just changed a little bit and it’s it now has many different and you mentioned several of them many different connection points that might be your so I think it’s it’s more of a semantic term now in my mind um in my case I was in a business that had been very successful for a long time and something was telling me that continuing to just do the same thing was not going to guarantee success for the next several decades and I didn’t really want to do the main things that they had been doing and I think I felt constrained by it and so to your point I felt like okay I can’t I can have this life but you know I’ve heard people say this before where if you see your entire life in front of you like if I project and said I’m going to have the next version of my father’s life it’s not your life and I I needed to have more of my own life my own adventure and I think my parents recognize that I recognized that and said you know I just think I’ve got to go figure this out myself and I think you’re you’re view of finding your your tribe is probably a great way to think about what I probably felt the the pull to is I have to go find uh the people that are going to challenge me and fill me and that that’s an adventure I I feel like I’ve been on for a long long time and and I’ve been a part of a number of different tribes whether it was it you know University or in the the city or graduate school or startup communities or others that I’ve been a part of and it’s just been so life-giving to me over those last few decades.

Jeffery: And it’s pretty impressive that you saw this early on and you were able to kind of start to drive your way towards that and really classify this as as a tribe Gathering and what you wanted from that tribe and it falls really closely to a startup space where when you are starting to create your business and you’re trying to figure out how do I start this where should I go and people always tell you a million different things on how you should start your own company and what you should look for and how you should do it but it really sounds that there’s a real definition towards finding that tribe but not only from a sales perspective but just getting people that align early on if that’s three people in your company those three people need to be part of that tribe and and what are some of the things that you look for like what you said a gut feeling there’s a lot of drive towards that but what is this tribe that everybody’s trying to find and that’s going to help them build a better business or stay on track to build the right business or be learning to Pivot like what what are those things that really helped you is that finding a tribe of investors that only invest in this type company and then making them mentor and some of the stories they were sharing earlier where it was aligning to putting that focus in on it and saying hey this is what I’m going to do and I want to raise 100 million dollars and you’re like hold on that’s not really what you should be looking at doing here this is something a better approach is is it really trying to understand in those facets of a tribe.

Carey: Yeah I I think it is um and yeah one of the things that I I like to assess and a Founder is and I think this is where storytelling is such a powerful skill for Founders to have because really their their envisioning a future state of the world that they have successfully shaped and moved forward in the area that they’re focused in and so their ability to articulate what that’s going to look like why that’s going to happen and how they’re going to be part of it is so useful for them and it’s also powerful in attracting in those people they need around it and to your points it’s not a singular group of people you could have a Founder who is really good at selling this future value and vision to customers and nobody wants to work with them because they’re they’re just very difficult it you know when when it comes to empowering others or encouraging others or managing others whatever that may be and that’s you know sometimes you you still would support them with that and try and hope that you could help develop their skills but but I think that um you know that as a magnet to building that tribe which could be customers part business partners you know employees potentially investors the the others around I think that is a key part of the evaluation of are you a Founder that you know in any of those roles I’ve I’ve evaluated it many times in my career from The Business Partnership standpoint do I want to join you and put my time and talent and treasure and because a lot of the startups that I’ve joined I’ve literally invested in the company as an investor and someone who’s going to join the team and be a key part of the team and whatever role I can play that can be additive to that I’ve literally had every job that you could have in a company because I don’t care I’m like let’s put the best team we can together and let’s go win and that that’s how we’re going to have our best opportunity to go shape the future so I think you know that ability to articulate the the vision in the future and that ability to attract others to it to want to be a part of that and be part of something bigger than themselves I think is a key part of building that early startup tribe.

Jeffery: And with this tribe you mentioned that over time people start to lose get distracted start not to feel part of that it does that mean that this tribe is going to keep shifting and changing and that you should look at it as the people that are here today are not going to be the people here in five years or ten years so just know that that you’re going to get the best out of all of these people in your tribe but just know that they’ll be kind of an auxiliary tribe they’ll be the outside tribe they’ll still be there supporting you but they may not be in your business and you kind of have to grow with that and that’s okay.

Carey: 100 percent now the hard thing there you and I have lived through that for a younger founder who’s never experienced it I think that’s a hard conversation to have early on because they just don’t I’m Different it’s different we’re different whatever it is it’s almost a distracting conversation in the early stages that you know telling somebody for example don’t get too close to this group because most of them probably aren’t going to join you as you get from four people to 40 people to 400 people it’s it’s almost a conversation that I I don’t think is worth having until it’s time to have it it’s sort of been my conclusion if a Founder wants to have it with me I will have that conversation all the time and I have stories and experiences for days I can share about how to help with those Transitions and do it effectively how I’ve seen it done very poorly painfully and often I will offer them options when when it comes time and say here are a few options that I’ve seen or that I would propose you might want to consider and you know the ultimately it might be your decision if you want some recommendations as as most people who meet me find I I very commonly will say I have opinions on virtually everything the because in a lot of cases it’s because I’ve already lived through it and it’s it’s gone well or it hasn’t gone well and that’s helped shape my opinion but whether that opinion or that view is good or not is not necessarily up for me to decide that’s really more either for you or the market or others and so I come with honesty and Candor and as informed and opinion as I can but ultimately some other uh evaluation is going to occur on whether the the quality that’s high or not.

Jeffery: But I think that’s really valuable in the sense that you can utilize that past experience and skill set to enable those Founders or the business people to better understand what they’re going to be faced because I think firing someone the first time is the most uh discouraging thing you can do because.

Carey: Yeah the worst I mean I feel like it’s the worst part of work.

Jeffery: Totally and you don’t know how to manage it there’s a lot of feelings there’s a lot of things that you’re not used to and it’s thrown at you and you know it could put you into the wrong space in the future which means that every time you do have to let somebody go or change a direction uh Panic or whatever might there might be a lot more things that come into it so having somebody that understands this and has gone through this space which also kind of refers back to another reference that you made which was when you were an entrepreneur and because you built companies been part of early stage companies that also kind of really sums up this the comment you made is that as an entrepreneur or being an entrepreneur you got to act like you own the business and you’ve got to work yourself into that space and take a different mindset and I think that’s actually pretty amazing on how you shared that and I’d love to explore that because it kind of fits in with this tribe piece is that you’re saying hey I’m part of your tribe but I’m also not just someone at the bottom of this tribe I want to be part of this tribe 100 I’m going to treat this like I own this business even if I don’t I’m going to to do that how do you put yourself into that mindset because I think a lot of Founders or co-founders or people that want to be really tied into a company they tend to just treat this like a nominal job like uh I’m in and out don’t care we’ll be gone in five minutes or got it at five and I’ll be gone in six months I’m gonna find another job how do you get people to change their mindset around to act like they own that initiative or own that role and be better so that they can provide more value into the business because they never know that that might actually become their tribe and they may want to be there for the next 10 20 years.

Carey: Yeah it’s a great great question I think in my case I I was given a gift by the fact that I grew up in this family business and we owned it and I was by designation of being part of the family even though I was the lowliest person there when I was you know sweeping up sawdust in the in the yard there was kind of this sense of pride of hey I’m part of the family and I’m not entitled and I think there’s there’s always that potential that entitlement can can set in I I didn’t feel entitled I felt a sense I have to prove that I should be here because you know they could probably fire me and go find somebody who’s better at sweeping but I I and so I think some of it starts with just personal pride of doing great work and wanting to put your time and attention to things that you can do well and show people hey I’m I’m good at this and so I think some of it starts with the human and the individual and saying if you’re going to do things I’m a big believer if if you’re going to spend your time doing things do them the best you can and then on the other side if you’re given an opportunity I mean this is why I love startups in that in most startups everyone’s been giving being given some amount of equity and they are literally given the the option for some ownership and so there is a finite a financial alignment there which I find good but it is also to what you said it’s a mindset and I if I’m going to spend my time being part of something I want to be part of something with my whole person and I want people who are also thinking that way and there are times where you just need somebody to do a good job for you and it is a job and I think increasingly what you see in the marketplace is those people I might just hire as contractors or as business partners but that Core Group you want that emotional and intellectual buy-in from and sometimes it’s about giving them the financial access and and that helps do it and then I think in other cases it’s about giving them the agency and the ownership literally of some amount of the work to do it and so you can’t I don’t think you can have people in a company that you want to think like owners and then you don’t treat them like owners like you can’t cut them out and and so I think culture is important in how you think about it enabling empowering giving people agency and and you know some amount of ownership and authority to to a level that makes sense that helps reflect it so it’s it’s a multi-faceted thing in my view but um I think you can sometimes get people there sometimes you can’t and so I also try to really screen for people who who do want that.

Jeffery: I love that and I think there’s a fine balance between how much you need to take on and how much you can distribute to the team and why I say it’s fine because I think we go in thinking we have to run and operate all of it and that we have to be the end result to all of it and I believe that’s the incorrect way of looking at it that you’re going to grow faster and and be scalable once you start to empower everybody and once that empowerment occurs then the ownership of feeling that they’re an owner and they’re a driver of this business that they matter is going to change the Dynamics of how that business runs and maybe that goes to your other point which is the level of curiosity that that individual has and if they don’t have the Curiosity to your last point maybe they’re not really the best fit but if they have that Curiosity and drive that’s going to keep them motivated to keep pushing the business forward.

Carey: That’s right I I totally agree maybe that’s the number one trait I tend to look for and hire for is curiosity and partly because curiosity typically means people are pretty humble they realize how little they know and they’re motivated and driven to continue to learn and almost fed by the opportunity to grow and learn and especially when you’re in a startup you typically want people that can grow and learn and take more on over time because especially in those early days you don’t have people that you generally want who have done this job before the reason you’re starting a startup is because you think there is a different way to do something and better way to do something and you need people very open to the idea of how to potentially do something much differently and better and so people that have done it a way may come in and not have that Curiosity and willingness to to shape and change things in a very different way that that is the whole reason you exist so you need those very open people and willing people to to be part of that particularly the early tribe.

Jeffery: I love it I think there’s a lot of great learnings here on how to shape a team early on and how people can start to build that tribe and build the Curiosity in the people there and a lot of it seems to come back to empowering them uh financially and and through all aspects of the business and now you take what you’ve done which is you’ve accelerated these companies you’ve dived into so many companies today and when we were chatting before you were like that’s what gives me energy was it’s not being in one area one company one it’s across many spectrums so you’re being challenged all the time which is to an earlier point you met you shared which was I want to challenge myself so I think you’re at full challenge so challenge is at a thousand percent can you explain what the difference is between a venture Studio an accelerator incubator and should these all work together is there a cross-pollination of these as an entrepreneur founder like when I come to you and I say uh you know what I’m lost I gotta create a company I’m looking for funding this is what I do you love the company you love that there’s a tribe but you’re like you need do an accelerator first then come see me or is it come see me then go I think there’s a confusion because we always hear all of these terms and they all seem to layer into the same which is I’m getting help from somebody that has a lot of helpers and but the names are so confusing which one should I start with or where should I go maybe you can kind of break that out a little bit.
Carey: Yeah it’s a great question and I think it is confusing I I totally agree with you I I tend to not accept the names we we for you know as humans we like names of things because we’re lazy and uh oh I need to go to as you said I need to go to an incubator I need to go to an accelerator whatever when we start operating people like are you an incubator are you an accelerator I said no we’re a studio like what’s a studio I go exactly don’t worry about what the name is worry about what it can help provide uh once inside and so what I would always and I do this frequently encourage a Founder who says I need help where should I go is go a couple levels deeper and understand what do they need help with do they need help with getting the problem that they think they’re solving validated do they need help with getting Capital do they need help with getting people to want to be part of what they’re trying to build what is it that they actually need help with and I think in so many cases in our world if you show up at somebody’s door and say I need help and they’re in the business of giving help they may try to force force their capability on you and you go well I showed up at their door they said they can help so I’m here and I tend to look at it the other way and say the clearer you can be about what help you need the the better you’re going to match with exactly the the right help and you know I’ll give you an example one of my partners on the bank Tech fund he runs an accelerator for banking Tech startups and what he does it is a true business accelerator and so if you have a company that is trying to get into and work with Community Banks he has an acceleration program where you will apply and join his program and over the course of 10 weeks you will get in front of 250 Community Banks and so he would say if you are going to benefit from being in front of 250 Community Banks in the next 10 weeks you may be a good fit for our accelerator if you just need broad business acceleration advice we’re probably not the right fit for you and if you’re a super early stage company and you need feedback from a couple banks to tell you if you’re on the right track you’re probably not a good fit because you’re going to drive 250 Banks crazy over the next 10 weeks with a solution that hasn’t been vetted and thought through enough and so there’s he’s found the boundaries of where are they in their business life cycle he’s ended up with some mature companies that said this is an incredible Business Development opportunity for us we’ll come in and be part of this because so I think sometimes it’s the clarity on the side of the provider but it’s also really going a little bit deeper as a Founder to understand where do I need help support Business Partnership at this point because even you know as we were talking earlier about Studios there are a lot of different Studios that could in your case look like some incubation help could look like some acceleration help depending on where you are and it is a bit of a matching process and and I would say also a matching problem.

Jeffery: It sounds like the key to to figuring out as a startup company where or even a scaling a mature company is that you need to look more internally at what are the problems you’re facing and write those down and Define if your team can’t solve these problems then who can solve them is it a consultancy is it accelerator is it an incubator so I think what it kind of sounds like people are doing is they’re not actually trying to solve their problem they’re trying to fit into somebody else’s solution because they don’t know what they don’t know and that’s the biggest fear is that I need someone to give me as I call it the Canadian hug because um Canadians look for hugs Americans give the Heisman so it’s the capitalist versus the Socialist environment and uh so people are always running around looking for I I’m missing my hugs someone’s got to help me and I think we have to figure it go deeper and figure out what is our real problem that we’re trying to solve and then find the people that actually solve that Niche problem because they’re going to end up spitting and wasting time if you don’t look at it from as you say internally and figure out what you’re really trying to fund.

Carey: Totally agree and and look sometimes you may go into a place you don’t know what you don’t know and you have Serendipity and you just meet that right person who’s in there who loves what you’re trying to do and they’re they’re there to help you and they help you immensely and they maybe even help you realize what you need so so that can still happen what I you know having done so many of these what I really try to focus on are how do you increase the likelihood that you can get it right and there is there’s no guaranteed success formula or pathway and you know I I like when people say the default posture for starting a company is failure because the vast majority of them fail so what are the things you can do to increase the likelihood that you actually succeed and don’t fail but the the default position is you’re going to fail because most of them do I mean we have to be pretty crazy to try something that has very very low odds like starting a company does.

Jeffery: I love it and and it’s I think it really shapes for kind of our our next segments and that is if we were to dive into um a case study that shows what it takes to be an entrepreneur what would be something that you could share and it could be win losses but I I think the audience gets a better view when they’re learning about these little different facets that you may not think about and now you’re sharing um you know it is a tough life and it is a tough grind and if there is a high fail rate you want to get to success faster and you need to do all these things include people tribes there’s a lot of things that will help this be successful can you share something of maybe a founder or a business that you’ve created where it blew your mind on where it went and and the outcome but positive or negative.

Carey: So I I mean let’s start with the founder first I mean I I you know one of our mantras that operate is you know Founders we can love and so lovability takes a lot of different forms but you know one of the things that I really gravitate to and love is this founder who is very clear that for this season of their life this is going to take over their life like this is what they need to do they have a really strong why they have a really strong view of I have to go do this it’s not hey you know I was lacking other things to do and we just had this idea so we’re gonna go try this it’s I I’m obsessive about solving this and it’s usually in the early stages especially it’s in my mind it’s not about building a business it’s about the the people they’re trying to impact the customers the the market that they’re trying to be in that they want to change they want to go forever change that world and and so that to me is a key lovable trait is that person that just they’re they’re out on the Spectrum and this is something they have to go do and then that will help in my mind typically means that’s going to help with them telling this story to get other people to join them in this journey and so we you know we start with that then we start next with okay are they working on something that we can get excited about because again we’re all humans and I’m going to be much more helpful and proactive to somebody when I think it’s a really interesting problem that they’re trying to solve and a really interesting group that they’re trying to solve it for and so we we then you know typically go there next and then the last one for us is can we be a force multiplier can we help them get there faster can we help them be more efficient are they are we going to have good chemistry and how we work together because to your point it’s super hard and the the likelihood this works is low so what are the things we can do to increase those odds and you know I I and sometimes will even say create unfair Advantage do we know some people that we can help attract in to join them that are going to give them even more advantage to potentially be a winner.

Jeffery: And I love that part that you said because you’ve said this a couple times be a winner so I love that I think that’s fantastic it’s a great way to kind of summarize everything that you’re looking at is whatever I build or whatever I do can I be the best at it and can I blend and let’s go win.

Carey: Yeah and you can probably gauge I mean I’m a really competitive person uh and you know even I have three boys at home and you know we it’s kind of you know whether we’re playing a game or whatever it’s just it’s fun to compete and you know I don’t always win anymore because they’re getting older but it’s the I think the spirit of that competition and so I think in you know I start a Founder who feels compelled to have to go do this there’s a competitiveness there in that I have to go do this so I better go do it well.

Jeffery: I love it agreed okay we’re going to swap into the 60 second rent I think uh you’ve been prepped for this I’m going to set my uh timer and uh we were going to jump right into this so give me two seconds here when you’re ready 60 seconds Let’s Hear It Go.

Carey: So Jeffrey I think the the rant for today is about what we were just talking about Founders sometimes get totally distracted by capital and funding as a proxy for them having a real business and you know we just talked about I want people who are obsessive about the customer and the problem and that they’re trying to solve it and sometimes raising Capital they confuse for hey I’ve got a real opportunity here I’m going to win and capital is just giving you the lifeline to potentially go when and get the other people around you to to go do that and sometimes they think the money itself is the validation and I think that’s where I get really frustrated at times and that they they want me to get excited for them because they’ve raised capital and I say great now you have an opportunity but use that as the fuel to go build the Great business that you have in front of you this is not validation on its own.

Jeffery: I love it and I think from that perspective of the fact that we use validation by how much money I’ve garnered there is a lot of Founders that are really fantastic at raising funds and forget to build a business that’s right but then there’s the reverse where you’ve got a lot of Founders that are creating big great businesses but they aren’t looking for Capital they’re not understanding how the Venture Capital side works or the point of venture capital so is there a happy medium inside of this is Venture Capital creating the problem by funding these ftxs and the Wii works or the wees and all these other companies where they’re dumping tons of money in and they haven’t actually looked at is this a real business model and they’re following the fomo at the same time.

Carey: Yes absolutely both both groups are complicit in my mind you have Founders that are good at playing the game and selling a vision for a platform that can consume a whole bunch of venture capital and you have capitalists that have a need to deploy in some cases large chunks of capital we’ve seen a number of funds get increasingly larger and that means they need to be able to deploy large amounts of capital when you have a big fund and so both sides I would say have been complicit in taking their eyes at times off of the business fundamentals of what does it take to fund and build a a great business and where where I tend to think about it is in the early stages of a business why you typically need venture capital is because you have super high uncertainty and you need Capital to help you learn and get to a more certain future and because you have such high uncertainty your best available Capital source is a high risk High reward Capital Source otherwise known as venture capital a bank is probably not going to give you capital in a high uncertainty environment as that company becomes more clear and more certain how to invest Capital into it there often are better sources of capital than Venture Capital to fund it because you have much more input output certainty and I think that’s where at times Founders or business operators aren’t necessarily considering other Alternatives that may be ultimately much lower cost options for them.

Jeffery: I love that high uncertainty I I’ve never had someone phrase it that way and I think that’s brilliant because it’s exactly what it is it’s that there’s these super high unknowns and I believe I’ve got something here I want to win and I’m going to get all of these people to kind of circle around me and we’re gonna all attack this uncertainty and the risk level is that we can lose this all or we’re going to find our lane and we’re going to take that lane versus we have a great business great Lane and people are just dumping in that money because you have a potential in three years to exit to the public markets you’ve already found your lane you’re already moving forward and now that’s just less risk way less risk and it’s more of just can you keep and operate your business without the outside problems coming in and crushing you from governments to um you know distribution of products operations whatever it might be so there’s there’s a whole different side to that and I don’t think people look at Venture as being this uncertain side and I I love the way that you phrase that I think that makes a huge difference.

Carey: Thank you

Jeffery: We’re going to jump into uh our business uh rapid fire questions pick one or the other Raider roll.

Carey: Yes

Jeffery: All right founder of co-founder

Carey: Co-founder

Jeffery: Unicorn or a four-year 10x exit

Carey: Four-year 10x exit

Jeffery: Love it Tech or cpg

Carey: Tech

Jeffery: Nft or web 3.0

Carey: Good question probably web three

Jeffery: AI or blockchain

Carey: AI

Jeffery: First time founder or a second third time founder

Carey: Probably second third time founder

Jeffery: First money in or series A

Carey: I’m a first money in personality I you know I I have sort of both these days but yeah I’d prefer It first

Jeffery: Okay Angel or VC

Carey: Angel

Jeffery: Board seat or Observer

Carey: Board seat

Jeffery: Safe or convertible note

Carey: Safe

Jeffery: Lead or follow

Carey: Lead

Jeffery: Favorite part of investing

Carey: Suspending disbelief and envisioning what this could look like if it really succeeded

Jeffery: I like that number of companies invested per year

Carey: I’m about 10 to 12 right now

Jeffery: Huge love it uh vertical is the focus

Carey: Obviously a lot in fintech and banking Tech these days um vertical Market software particularly as it increasingly is more and more intelligent and uh other Tech enabled services

Jeffery: Two qualities a startup needs in order to stand out to you

Carey: Founders who as I mentioned earlier have that just clear why that they have to go do this and insights on why the this is the right time to go change this industry

Jeffery: Okay what is the piece of advice you give Founders nine out of 10 times

Carey: I think they’re they’re probably two one is focus more on the customer and the problems of the customers and deeply understanding is this a problem we’re solving that they are motivated and care about changing and focus Less on your product and the second is understand if you really are going to raise capital is there a fair opportunity for the investor involved to make money have you thought about the math and because far too often they haven’t even thought through what that could look like for their business partners the investors to come alongside with them.

Jeffery: Do you have a philosophy or rules that you stand behind.

Carey: I have a lot of them as you probably heard throughout this so I don’t know that I will uh recite any more of them but yes many

Jeffery: What tech will Define the world in the next five years

Carey: It’s it’s I already feel a little bit um you know Annoying with myself to say it but I do think AI is having its moment people are paying attention to it and how it will be used to augment Humanity make our lives much more creative and flexible I’m pretty excited about

Jeffery: Great who is your hero mentor and why uh

Carey: My hero I think is my father he’s just been such a uh open and honest supporter encourager and frankly you know uh enabler of me to to say you you don’t have to come back here and be a part of this family business uh I want to see you go be the best version of yourself in the world and and I think just that gift uh I’m so grateful for

Jeffery: Brilliant toughest lesson you have learned as an investor

Carey: People can disappoint you and you know even when you think uh they’re who you think they are they still humans humans can let us down and I think that that’s probably the toughest lesson to learn is you know even when you feel like you’re on the same page and you’ve got the same view of where things need to go sometimes for other any number of reasons they they can deviate and let you down and that that’s just part of part of life

Jeffery: True true what is the most important technology that you feel has been built today or will be built in the future I

Carey: I’ll focus on the future because I don’t know that it’s been built yet and I think it’s in process is helping us as humans understand what’s inside of us at a much deeper level that biological level at the psychological level there’s just we are these incredibly complex machines and I’m fascinated at times how little we actually know about them and so I think you know anything that’s increasingly helping us understand what’s happening inside because we’re in many cases becoming less and less connected to each other from a human standpoint and a more technological standpoint and I’m not sure we even fully understand what that’s doing to us and so you know that deeper understanding of uh the unique individual inside of of each of us and and the biology chemistry Etc of all that I’m fascinated to see um you know what new technologies will emerge to assist that

Jeffery: Likewise called The Human Condition there’s so many things we don’t know

Carey: That’s right

Jeffery: What is your favorite investment that you’ve made

Carey: My favorite investment that is a good question it probably right now is a company that I helped co-found last year called bonus and we are helping homeowners build a future wealth in from their home in a in it’s something that has never been thought about to help people build more wealth through home ownership it’s typically been something others have sort of preyed on and built businesses around as an industry and homeowners have sort of benefited at times but often not from owning homes has been much more utilitarian for a lot of people even though it’s for a lot of folks in the US their greatest asset and so I think conceiving the concept of how we could change that and uh it’s you know because I got to be both the co-founder and first investor in it um I I have high uh interest ownership and sort of uh that founder uh value in it that that’s what probably makes it my current favor

Jeffery: love it what is one thing you would change about venture that doesn’t flow or work for you today

Carey: I I struggle in in the Venture world I understand it I struggle with the spreadsheet driven investing approach in that in many cases they will pass on a deal because they can’t get the ownership percentage or they can’t get the capital that their spreadsheet is telling them they need to put into a company and I I think this is such a creative and human business that it those are the moments where I I’m frustrated and say this isn’t a the right way to do it I think it’s about helping people de-risk and build great businesses and doing it with some maybe some guidelines and boundaries but these really structured approaches to it that you know is more of a later higher certainty private Equity driven approach I think is is in those early stages is just really frustrating and I would say you know delusional frankly

Jeffery: Well said all right we’re almost there personal questions most famous person that pops in your mind

Carey: Abraham Lincoln nice

Jeffery: First brand that pops in your mind

Carey: Nike

Jeffery: Book or movie

Carey: Movie

Jeffery: Superman or Batman

Carey: Superman

Jeffery: Fortune cookie or birthday cake

Carey: Fortune cookie

Jeffery: Five minutes with Bezos or Oprah

Carey: Oprah

Jeffery: Mountain or Beach

Carey: Beach

Jeffery: Bike or run

Carey: Run

Jeffery: Big Mac or chicken McNuggets

Carey: Chicken McNuggets

Jeffery: Trophy or money
Carey: Trophy or money trophy

Jeffery: Beer or wine

Carey: Wine

Jeffery: Ted talk or book reading

Carey: TED Talk

Jeffery: Tick Tock or Instagram

Carey: Instagram

Jeffery: Facebook or LinkedIn

Carey: LinkedIn

Jeffery: Favorite movie and what character would you play

Carey: My favorite movie is probably Hoosiers because it it is a great Story movie and also it always reminds me where I came from and you know I probably would play Gene Hackman who’s the coach

Jeffery: That’s a great movie and I haven’t probably seen it in 20 years so I’m gonna have to go check that one out very cool favorite book

Carey: Probably the Bible

Jeffery: Like it favorite sports team

Carey: Go back to it all the time favorite sports team is my alma mater Indiana University basketball team

Jeffery: I like it all right cool what is the meaning of success to you

Carey: Success to me is I think two parts one is becoming the best version of myself and challenging and growing into the person that I can be that you can have then the biggest impact on the world and that is you know how many people can I positively impact in the various ways that I can through the skills that I’ve developed through the groups that I’ve been a part of and whether it’s a lot or a little impact that I can have so to me that’s that’s success.

Jeffery: I love it and what is your superpower

Carey: Uh I think probably what we talked about earlier which is my ability to um relate and have at least an initial meaningful conversation with almost anyone and that Curiosity that that drives me to engage with them around

Jeffery: That I 100 agree with that I think it’s a fantastic skill set so great script power well I’m going to say Carrie it’s been a pleasure getting the opportunity to learn more about yourself and to dive into your background and to the Future and you’ll be you’re a rock star it was phenomenal uh Lots so much learning I’ve got millions of pages of notes and I just wanted to say thank you very much for all of your time and the way we want to and we like to end our show is we like to give you the last word so anything you want to share to Founders or investors I turn it over to you and please also share how people can get in touch with you as well.

Carey: Well Jeffrey it’s been a pleasure I uh don’t get a chance to answer these kinds of questions very often and uh it was it was enjoyable I really appreciate it so thank you for putting me on the spot and and giving me the opportunity at his final thought I have such a huge heart for entrepreneurs I love people who want to go out and Dent the universe and make something better for the world and it’s just such an inspiring thing and it’s so hard and it’s hard to say no it’s hard to say no to them it’s hard to to not want to support them all and you know I just encourage all of them to keep going and they’ll they’ll find their way whatever that way is supposed to be um even if if we can’t be a part of it um the easiest way to find me these days is probably on LinkedIn I’m pretty active on there I try to be as responsive as I can be you know we have websites both for operated operatestudio.com you can contact us there and Bank Tech Ventures at banktechventures.com as well and uh I just as I said love seeing the entrepreneurial energy that continues to exist and in fact I think is even growing in our world and I’m privileged to be a small part of it

Jeffery: I love it Carrie you got a fantastic podcast you’ve done amazing startups and a great adventure Studios so thank you for all your time keep up the amazing Works brilliant thank you.

Carey: Thank you

Jeffery: Well that’s a great conversation with Carey so many great points that he brought up there and I think I’ll just touch on a few of them which is obviously trying and working to find your tribe and that goes for uh building your company when you start all the way through your journey you’re always going to be tying in people into this journey so find that that tribe and be curious stay curious curiosity is what creates such an exciting awesome world is that the people that have the ability to have this curiosity are the ones that can help drive and make the change challenge yourself everything you do keep challenging yourself to learn more be better every day um and I guess the other things that it would really tie into that is when you are looking for an accelerator incubator where you’re working your way into these new startup phase figure out what your real problem is figure out what things you’re not able to attack build or grow from and once you figure those out that will kind of leave lead you into if it’s an accelerator incubator or Venture Studio but really start to hone in on what that problem is and how you can Propel yourself forward uh Dent the Universe. I love that saying he just said that at the end make a dent figure out how you can make a change and do something that people will appreciate in the future uh you know be strong and uh have a strong strong why on what you’re doing I think that will really help uh carry you forward and figure out what your unfair advantages what are things that are going to make you better than everybody else and then just be the best at it that’s really the key to entrepreneurship be the best thank you for joining us today if you’ve enjoyed this conversation please feel free to share with your friends subscribe to our YouTube channel and or please follow us on Spotify apple or Stitcher platforms feel free to share an audio video clip around the show and we may include it in one of our future podcasts you can find us or follow us at marketing oppeoplenetwork.com or on LinkedIn at supportersfund your support and comments are truly appreciated please visit us at supportersfun.com or startup events at openpeoplenetwork.com thank you and have a fantastic day.