Concentrated and Creative Investment Strategies

Hosted By Matt DeCoursey

Full Scale

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Jeff Cantalupo

Today's Guest: Jeff Cantalupo

Founder and Managing Partner - Listen Ventures

Chicago, IL

Ep. #813 - Concentrated and Creative Investment Strategies

In this episode of Startup Hustle, Matt DeCoursey welcomes Jeff Cantalupo, Founder and Managing Partner of Listen Ventures. Join them as they talk about concentrated and creative investment strategies.

Covered In This Episode

What is a creative capitalist? What do they look for in an entrepreneur?

Matt DeCoursey and Jeff Cantalupo discuss investing, backing, and building consumer brands of tomorrow and other investment strategies. Jeff also shares what qualities and traits Listen looks for in its portfolio of founders.

Get Started with Full Scale

Aside from those topics, Matt and Jeff talk about brand and branding. They also cover the differences and similarities between corporate and startup environments.

Tune into their conversation in this Startup Hustle episode today!

Hear What Entrepreneurs Have to Say in Startup Hustle Podcast


  • Jeff Cantalupo’s background (1:17)
  • The creative side of investment strategy (3:24)
  • The Three Cs (6:42)
  • Corporate vs. Startups (8:55)
  • Creative Capitalism (12:38)
  • Early stage and brand building (13:37)
  • Brand building (16:35)
  • Creating experience (17:39)
  • Listen Venture closed four funds (22:11)
  • Opportunity fund (24:34)
  • Chicago’s innovative food sector (25:52)
  • Effects of the Pandemic (29:03)
  • Mental Health (31:52)
  • Listen Venture’s approach to diverse investment (33:24)
  • Qualities that investors look for in an entrepreneur (35:19)
  • Jeff’s freestyle (39:05)
  • What is Matt listening to (39:34)
  • Traits of a genius (44:23)
  • Wrapping up (47:45)

Key Quotes

It’s the three C’s that work together in terms of our business, you got to have curiosity about the world, you got to have curiosity about what can be done or done differently. And then you got to have the capital to put to work against those ideas. And you got to have the creativity to help grow those businesses and grow those ideas.

Jeff Cantalupo

Building a brand is about making sure that every experience that your constituents come into touch with your brand or your company feels like it’s adding to the value. It’s building trust over time. And so, building a brand is about systematically creating an experience with a consumer over a period of time.

Jeff Cantalupo

I really feel that a good brand creates that peace of mind. And I think that peace of mind is, first off, without it, nothing else has much flavor spice. And it’s really like an intangible thing that you can’t really put a value on. So like, giving people back their time or their peace of mind is inherently valuable.

Matt DeCoursey

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Rough Transcript

Following is an auto-generated text transcript of this episode. Apologies for any errors!

Matt DeCoursey 0:01
And we’re back for another episode of Startup Hustle, Matt DeCoursey. Here to have another conversation, I’m hoping helps your business grow. So yeah, investment exists in so many shapes and forms. And, you know, we could really go on and on and on for probably the rest of our lives about that. But today, we’re going to be a lot more focused. And we’re going to talk about concentrated and creative investment strategies. I’ve got a subject matter expert that I’m really excited about diving in to this conversation with today. Now, before we before I tell you who that is, or get too far into that today’s episode, Startup Hustle is brought to you by, helping you build a software team quickly and affordably. That’s my company. And I’m looking forward to hopefully giving you some good advice about your future tech team. Go to and go to the Get Started page. Tell me a little bit about what you need help with and we’ll get right back with you. And with me today, I’ve got Jeff Cantalupo. And Jeff is the founder and managing partner at Listen Ventures. Go to Just scroll down to the show notes and click the link. And you know what? Go ahead and do that now. So you can have a little context about what we’re talking about. Straight out of Chicago, Illinois. Jeff, welcome to Startup Hustle.

Jeff Cantalupo 1:17
Thanks, Matt. Really excited to be here with you today. Yeah, and I’m looking forward to it as well. Now, you know, I would say conversations to hopefully help your business grow. But before we get too far into conversation, give me a little bit of your backstory. And you know, the listeners want to know, too. Yeah, sure, I guess, quick history. I you know, I’m born and raised Chicagoland area and western suburbs. I went to school at the University of Iowa for college, undergrad. And then I landed for the first part of my career in the advertising world. So I spent a decade at an advertising agency called Leo Burnett, which is a global ad firm kind of best known for, you know, partnering with kind of the Fortune 50, if you will, and creating a lot of the characters, we grew up with Matt, whether it’s Tony the Tiger or some of the others. But I cut my teeth kind of learning how to build businesses through a brand lens while I was in advertising. And then, and then through that I got a lot of exposure to innovation strategy. So I helped work on innovation. Strategy for companies like Kellogg, and Procter and Gamble, and Philip Morris. And through those experiences I got, I kind of caught the the bug for identifying whitespace and launching new brands, I’ll be it through kind of the big, big company philosophy. And that’s also what led me to get real excited about what was happening in the startup ecosystem. So 2010, I left Leo to start the first iteration of Listen, which was essentially a naive dive into the world of investing in venture capital. And, you know, 11 years later, we’re, we’re currently investing out of our fourth fund, and you know, what our purpose is to back and build what we call the brands of tomorrow. So we, we are concentrated investors, where we only invest in 10 to 15 brands per fund. We have a team of experts beyond our investment team of creative professionals and brand strategists that roll up our sleeves and help help to build brands. And so that’s, that’s the quick backdrop.

Matt DeCoursey 3:24
So I get the concentrated part. So as the creative side of the investment strategy, does that involve firsthand approach to helping those that you invest in build the brand, like saying, hey, you know, we’ve got a lot of experience with this. We’re concentrated by doing this small, you know, might, those listening 10 to 15 companies per fund might not sound that concentrated? Most funds are just like, the whole thing. Like, hey, we’ve got $100 million. And it could be two companies, or it could be 64.

Jeff Cantalupo 4:01
Yeah, yeah, just for context. They’re meant, like the majority in venture capital is, from an asset class perspective, it’s highly risky, right? You’re investing in startup companies. And so the, you know, the logic around investment strategy typically points you towards investing in a lot more. So like most of our peers are investing in kind of 30 to 50 companies per fund. So when I say concentrated, it’s in the context of venture capital being kind of 30 to 50 per fund versus ours, which is kind of 10 to 15. from a creative perspective, which is your question, you know, our philosophy is that, you know, every brand is a work in progress, no matter how big or how large you are, but it’s really true in the early stages. And so, when we think about creative investing, you know, it’s essentially approaching your business through a creative lens. How do you solve problems through creativity? You know, we believe creativity has the power to change human behavior, and usually when you’re building us startup, you know, that’s what you’re trying to do, you’re trying to change people’s behaviors around how they experience something, or how they buy a product or purchase something. And, you know, creativity is gonna go a long way in terms of unlocking opportunities for growth, standing out in a world that is increasingly noisy, and just, you know, constantly thinking about new ways to go after a market.

Matt DeCoursey 5:25
So in my spare time, I have been recently studying the habits and traits of genius and meaning, like what makes some people you know, genius and talent are often misunderstood. Because you’re talented, when you can hit the target that everybody sees. You are, you are potentially a genius when you hit the target that no one knew existed. And with that there are and by the way, once someone told me that I was like, Oh, wow, there’s a big difference between and people get confused. Because you see, some you’re like, wow, that person’s a genius they might not be, might just be really talented and good at repeating or prepper, preparing for stuff. Now with that, and you know, this is what creativity is largely seen as something a genius can never lack. Like without, without a healthy dose of creativity, and that creativity, also, curiosity comes with that. So the curiosity and creativity now just kind of started my ascent into this world. And I’ve been fascinated with this for a long time, but I’ve really gotten serious about it lately. So do you think that you know, like, you mentioned creativity, I think you got to be creative, kind of be a genius, because you got to build something that no one else has built? But is it? How do you feel about the curiosity side of that?

Jeff Cantalupo 6:42
The name of our firm is Listen. So if that gives you any insight to how we feel about curiosity, it’s, it’s what we live and breathe. And you know, I think, I think you hit the nail on the head, to me, it’s the three C’s that work together in terms of our business, you got to have curiosity about the world, you got to have curiosity about what can be done or done differently. And then you got to have capital to put to work against those ideas. And you got to have creativity to help grow those businesses and grow those ideas. So you know, I love that you you got to the curiosity as the part of the creativity notion, and at Listen, that’s, that’s what we look for. It’s actually the first word on many of our job descriptions when we’re hiring new folks.

Matt DeCoursey 7:26
You know, it’s kind of interesting, you mentioned capital, because one of the traits is also enterprising, which is like invariably involves the, quote, genius, or whoever you’re thinking about needing to go and find some capital, so they can be enterprising with it, because they can’t really get all the way down the rabbit hole, that they want to be down without it. And it’s in for many creative people. And, and, you know, people are building things, that’s not always their favorite thing to do. So, you know, when it comes when it comes to all of that stuff, hey, you know, I’ll let you know how the results worked out on that. So yeah, there really, there’s apparently 24 traits that you have, or are pretty dominant in any person, if you’re going to be a genius. Alright, so you know, you go from one world where you talking about working? I mean, how many employees is Procter and Gamble have worldwide? It’s like, huge, right? It’s maybe more than like some like little of the of the smallest countries that are out there. So you go from that what I, you know, highly corporate, to the world of startups kind of like the far end of it. What’s What’s something that surprised you that existed a lot in the startups world and something you might have also pulled from the corporate world that was useful? Like, where did where did those? Where did those worlds intersect? And what did you find?

Jeff Cantalupo 8:55
It’s so interesting, you know, I get asked the question all the time, like, what, what do you miss? Or what did you bring with you? And I think, what I always tell people in terms of the moving from advertising into venture capital, which seems very, like a very distant type of background or field, in advertising, like our job was to understand an audience, and then help our clients create communication that was culturally relevant to that audience. And so our job was essentially, you know, coming up with and then hopefully approving ideas that was going to connect a product brand experience to a consumer base, in an emotional way. And in a weird way, I think it’s incredibly similar to what you’re doing in venture capital, which is, you’re meeting with entrepreneurs, and you’re trying to understand if their ideas have the capability of connecting with an audience in terms of eventually creating a new type of business and so you’re discerning you know, what’s culturally relevant what what do you what do you look thing to accomplish with these and, you know, are these types of things and the narratives that consumers are looking to connect with. And so I think I take a lot from what I learned in kind of the big corporate world to working with startups. The difference is, you know, the startup world doesn’t come with a lot of the baggage that the corporate world does. And I like to call it a clean slate, right, when you’re, when you’re building a brand from scratch, you have a clean slate. And so, you know, if you’re promising something to a consumer, your decisions about everything in your business, not just the way you communicate, but the business model, the supply chain, everything you’re doing, you’re making those decisions from scratch. And so you can make sure that every level that you’re promising is the consumer, when they peel back the onion, they’re kind of reinforced with what you promised them is real, versus when you’re trying to keep a brand that’s been around forever relevant. You know, sometimes you consumer can take a peek behind the curtain and say, Hey, you’re telling me you’re the you’re the healthy food company. But that’s just your new brand. Because all your other brands you’ve been selling me for years, Nestle hasn’t necessarily been that healthy, right, for example.

Matt DeCoursey 11:10
So one thing startups don’t come with, that corporate does come with is an owner’s manual in many regards, which is, you know, you get the strength and weakness kind of things. And I always tell people, the thing that I think is hardest about any newer, upstart business, like, people will say, Well, what as a startup, because it’s funny, because they called Uber, a startup, literally until it went public. And I’m, again, not so sure that was a startup anymore at that point. But you know, the lack of an owner’s manual is as a key ingredient for something becoming a startup, I would think that, you know, so I’ve kind of been down your path as well, before I was an entrepreneur, I worked largely in the musical instrument business, but I worked for, you know, the world’s largest maker of electronic musical instruments for a while and I learned a lot of stuff about like how to do things properly. And in a systematic way, I think it was beneficial for me. And I also learned how bloated decision making can be so I think they I often compare us the game battleship. So startups are like that little two peg destroyer that you’re pissed off that you can never seem to find and hit, but they can out maneuver where the battleship is the battleship aircraft carriers, their aircraft carrier, so, okay, so. And when you hear the term creative, capitalist or creative capitalism, what comes to mind?

Jeff Cantalupo 12:38
Um, I think it’s just about, it’s about an approach, it’s about a philosophical approach to how you’re, how you’re investing in change. You know, that that’s what comes to mind. For me, I think, every entrepreneur, and we’re fortunate to be in a business where I meet people every day that inspire me. And they’re inspiring me with kind of creative, creative, creative thinking about the way the world should work, or the way a product should deliver an experience. And so, you know, I think I think creativity is the the engine for innovation. And I think, you know, capital and venture capital is, is going to be the fuel for that, for that creativity. And so that’s why we’ve kind of mixed match that that’s why our team is, you know, we’re probably one of the only venture capital firms that has a head of creative, right, and a partner that’s ahead of creative and so we take the we take this idea of creativity plus capital very seriously.

Matt DeCoursey 13:37
When it comes to brand building, what do you think is something that startups and early stage businesses are just terrible at?

Jeff Cantalupo 13:46
Oh, you know,

Matt DeCoursey 13:47
that was a hold my beer kind of laugh, by the way, because like, there’s, there’s quite a few. I’m just curious what your take Yes.

Jeff Cantalupo 13:55
Well, it’s funny. Things have things have changed pretty dramatically in the in the 11 or so years that I’ve been doing this in the sense of just the sophistication of founders around what it means to build a brand. I would say like to answer your question, specifically, I think one of the things that often gets wrong, gets done wrong, or maybe misinterpreted is, I think people misinterpret brand for branding. And, you know, branding is, yeah, you got to have good design, you have to have, you know, a logo that pops, you have to have good colors and a scheme that feels cohesive and consistent. But that’s one aspect of building a brand right? Building a brand is about making sure that every experience that your your constituents come into touch with your brand or your company feels like it’s adding to the value. It’s building trust over time. And so building a brand is about systematically creating an experience with a consumer over a period of time. It’s not just about, you know, the way you look, which I think is often kind of a misinterpreted, understanding about building a brand early on, at the early stage of building a business.

Matt DeCoursey 15:12
You’ll talk to early stage founders and you know, they’ll they kind of look at what we’ve done, whether with Startup Hustle or Full Scale. And you know, I employed, you had a four year old business with 225 employees worldwide. And, you know, you talked about building the brand, I’m like, well, we don’t have we don’t we didn’t have a brand. And like you, at which point you have a brand is when you have something that people recognize, like at all, and you know, as a startup, usually don’t. Now, how do you go about doing that, I mean, there’s a lot of ways to build a brand effectively. And there’s also even more ways to implode and destroy one, maybe save that for a completely different subject. But overall, I mean, you got to create value, you have to create value and like, and as I’ve gotten older, I’ve learned that a lot of it is about creating peace of mind, which is actually like a weird thing. And like a lot of people don’t consider that but you look at like, especially with a tech company, you know, it’s like you’re creating peace of mind, like something that turns the gears in the background, or helps you sleep better at night, knowing that this brand is defending your personal time, your business, something I mean, there’s a number of different ways. But really, in the end, it usually revolves around something that makes someone’s life easier.

Jeff Cantalupo 16:35
Yep. Yep. I think I think that is a huge use case, especially in tech. Right? Which is, we have this conversation all the time internally, Matt, which is like, is it? Is it a brand? Or is it a utility, especially when it comes to certain tech tech products or tech businesses. What I find fascinating is that, you know, I’m a brand guy. So obviously, this is a biased point of view. But like, I, you know, you’ve seen the consumerization of every category. And I’d say even b2b SaaS, right has become a very consumerized business, if you think about, you know, some of the biggest outcomes in the last 510 years, you know, Slack, Dropbox, those are all consumer brands, to the end user, they just happen to make their money by selling, you know, they’re they’re enterprise service to big clients. But I think it’s about building, you know, building a building an experience that people care about, and then want to talk about, and that’s ultimately how you’re going to build a reputation.

Matt DeCoursey 17:39
Yeah, and I want to talk more about I’m a big, I’m a big experience guy for a number of different reasons. Before we get into that. It’s quick reminder, today’s Startup Hustle experience, there you go, is brought to you by, helping you build a software team quickly and affordably reach out, we want to help you do there’s 350,000 Open tech jobs in the US right now, which is insane. And it makes it hard for founders to like find what they need to build what they need. And that’s actually why we started the company. My best companies that I’ve started in the past were an accident. And Full Scale kind of was two, we never really set out to actually start that as a company. Now in regards for experience. And I mentioned being a big advocate, we actually launched our brand, through experience-based marketing, here in our hometown in Kansas City, where we actually acquired sweets at all of our local venues and invited people to what we what I branded as sweet and greet. And I know I invented the term because there was no hashtags anywhere for that. Well, that’s how you check. That’s how you check your brand. Now you’re like, Hey, did I invent this? Because if there’s not a hashtag out there, but with that, we realized that by creating an experience, because okay, we sell software development services, man, like come on. That’s not That’s not like the sexiest thing out there. So we wanted to, you know, I had a history in the music industry, and entertainment and ticketing and stuff like that. So I knew that if I gave someone an experience that they remembered that they had fun out, and even better if they found valuable added around their business, they wouldn’t forget who we were, it was highly effective. Because, you know, we take you know, you get 16 people in a suite or something, you take basically seven or eight people give them a plus one, and you just throw them in the room and see what happens. Now, the result of that is, you know, people have a good time, they had fun and they met other people that were their peers and later became their friends and colleagues and maybe even did business with some of them. So that form of experiential entertainment and marketing can be really exciting and fun and memorable. They don’t forget you. I’ll tell you if I took you to see New Kids on the Block. It didn’t matter if you liked the band or not. You’re going to remember it was me. So a point now, that can be a little bit different than the experience someone has with your product. Like I mean real In the end, where I’m going with this and the and the next question I’d like to talk about is, what do you think is important for creating a memorable, valuable or brand building experience?

Jeff Cantalupo 20:12
Well, I think I think your examples spot on and I think what you’re doing is, is the analog of what a lot of what I would say kind of modern brands are doing which is there, you’re creating a community, you’re you’re bringing people together around a topic or or some sort of industry or product category, and you’re having conversations, I hope what you’re doing mostly Matt is listening. And, and listening to those folks

Matt DeCoursey 20:41
is off to often to rock and roll. But yes,

Jeff Cantalupo 20:45
But you know, you’ve got a credit, you know, a small kind of almost mini focus group, when you’re doing those experiential events, to listen to your customer. And think about connecting them with other people that are, you know, facing the same problems they are, which is how do you scale your, your tech organization, etc. And those experiences and connections and community that you’re building are, are really powerful. And over time it compounds and, and I think that’s, that’s the importance of, of how you build kind of a brand over time. And I think, what, you know, what the internet and social media and everything is enabled brands to do over the last 15 years or so since it’s become ubiquitous on social is that you can do that on steroids, right? You can do that, in a way that’s never been done before. You can have one to one relationships with millions of people. And you can connect them directly and form communities around, you know, a topic that you think is important to talk about, and it might be tangential to what your your ultimate product is. But if it’s brand-aligned, it makes sense for you to do that. And it’s and it’s in good business. And so I think just thinking really thought being very thoughtful and intentional about what your purpose is in the world. And then figuring out how you bring people into it, how do you, how do you create believers? And how do you at every step of the way, give them an experience that is going to be worth talking about?

Matt DeCoursey 22:11
I’ve had people ask me, they’re like, so you just have software companies come by now we say entrepreneurs, influencers and investors, and we are very, very agnostic with who we invite, because, and part of it and by the way has been highly effective. Because you know, I don’t want to like you, you’re an entrepreneur, or you’re not, you know, like, that’s kind of a binary thing. And with that, you know, the entrepreneurs no other we travel in packs, man. And, and, you know, and and by the way, the result of that is that we just have a remarkable referral network. Does that mean it’s like my business is basically fuel on referrals? At this point, I still don’t buy advertising for Full Scale. So you know, that’s another thing we did 7 million in sales last year and people like Wait, you didn’t? And then you take in the podcast and the revenue it creates, and then we actually had a positive marketing budget. Yeah, I joke I’d like it back in business school, which I dropped out of, by the way, I like to be open about that. But you know, if you had turned that in with your projections for your, you know, widget Corp, ACME Corp business plan, they would have circled that in red and would have said see me, teacher would have been like, Yeah, nobody has a positive marketing budget. But that was before the world of podcasting and social influence and stuff like that. Once again, with me today, Jeff Cantalupo. And Jeff is the Founder and Managing Partner of Listen Ventures, go to and see what they’re doing. I went to your website earlier, and you guys are doing a lot of really cool stuff. According to my notes, you’ve closed a recent fund or maybe continually in the process of doing that. Now, you mentioned having different funds. If so, there’s four so far, is that right?

Jeff Cantalupo 24:01
That’s correct. We’ve We’ve closed four funds over time, but we closed them in kind of a time based fashion, Matt. So you know, our first fund was call it 2010 to 2015. And we raised our second fund 2016. Then we invested that all the way up through last year, and we just closed our third fund and then a new opportunity fund that is on top of that. So you know, so we invest in we invested kind of 10 to 15 companies per each fund and you know, we roll up our sleeves and try to become real partners with our with our entrepreneurs.

Matt DeCoursey 24:34
So when you say an opportunity fund does that have a specific like when I when I hear that, I think okay, so I’m here at the new Startup Hustle and Full Scale studio in office in downtown Kansas City, Kansas, which has honestly seen better days and it’s in an opportunity zone. So sometimes when I hear opportunity, I think about that, but does the term opportunity being attached to that have anything to do with The fun with the companies that you invest in, or is that just a way to kind of know that it’s different than the others.

Jeff Cantalupo 25:06
So it’s, it’s a little bit of a moniker to know that it’s different. But then our strategy with having an opportunity fund is to have a separate amount of capital that we use to continue to invest in our companies as they mature. So our core funds, if you will, we invest very early stage, we’re kind of seed or series A investors in kind of startup brands, right? And as those companies continue to mature, we don’t we don’t, we have pretty disciplined size funds. So we don’t keep a lot of capital at the core fund to continue to maintain our position over time. And therefore we will raise an opportunity fund and that opportunity fund is kind of dedicated to allow us to continue to invest in some of our companies go on and continue to raise capital and mature and grow in the business.

Matt DeCoursey 25:52
So being located in Chicago, which is the New York City of the Midwest, for us here, you know, or LA, or whatever you want to call it, it’s our Midwest, big city. As you know, it’s become an innovation hub. And there’s a lot of stuff going on there. In my opinion, there’s some pluses and minuses to operate in there. One, it can be a little bit more expensive, just because it’s a big city, you know, there’s some finite nature of it. And then also, there’s a ton of opportunity and ton of people you can reach out to like how are you seeing Chicago change when it comes to being an innovation hub? Or you know, what, or is there anything? So in Kansas City, we it’s funny, because you know, we’re, I’m in the middle of a city, but people just think I’m in the middle of a farm on Sundays. But there’s a lot of like animal health and agriculture type stuff that goes here. So like, what’s, what’s been going on in Chicago? And what and is the city trending towards anything? Is there anything that really seems to stand out over and above other markets?

Jeff Cantalupo 26:53
Yeah, man, I think it’s a great question. I think Chicago is an incredibly diverse ecosystem when it comes to industries. And that’s largely because we have and I think it’s one of the benefits of our city at large, which is like, we’re not we’re not, we’re not over-indexed on any one industry, right? Like, you know, you look at Detroit and its reliance on the auto industry, right? Chicago has got a significant amount of diverse large companies. from an innovation perspective, it’s changed dramatically in the last 10 years. And I think we’re, you know, quite frankly, still just getting started. And even though it’s matured quite a bit, but some of the industries that stand out, and I’ll use ones that were very involved in, but, you know, we have created a incredible group and cohort of companies in the food innovation ecosystem. We have a number of, you know, one, we exited a company out of our fund last year called factor, which we sold to HelloFresh it’s it’s the largest prepared meals business now in the country. And we sold that

Matt DeCoursey 27:58
I will be eating HelloFresh for dinner tonight. Yeah.

Jeff Cantalupo 28:03
But you know, that that was a Chicago based company factor that we grew, you know, for, for a long period of time. Everything out of Chicago, and it was a it was a it was a national, nationally distributed brand. We have, you know, other food companies like home chef, which is a competitor to HelloFresh, that did phenomenally well, they sold to Kroger, we have a company called tovala here in Chicago, which is, you know, kind of reinventing the the oven, and in doing prepared meals on top of that farmer’s fridge. And the list goes on and on and on. And I think, you know, that’s on top of things like GrubHub, right? GrubHub was one of our biggest kind of early-stage food company outcomes in terms of a marketplace model that, you know, now you have DoorDash, and UberEATS, and everything else, but I think we built a really deep kind of innovation ecosystem around the food food sector. And so that’s one one that I would point to.

Matt DeCoursey 29:03
We’ve had Mike Evans, the co-founder of GrubHub has been on the show, actually not in the somewhat recent timeframe. So yeah, interesting story there. He and I ended up actually talking more about being, quote, passionate as startup founders, which some people just define as angry, which is okay, you know, that’s, and by the way, I love I love the fact that we’re now continuing to have a conversation about things that aren’t all tech, because you talk about, you know, you know, just like food innovation, and I mean, there’s so much of that now. You know, what’s something that you that what, alright, so the pandemic is a weird timeline for so much of us and you’ve been on both sides of it, or Well, I don’t know if we’re fully on the other side of it. But what’s something that you saw that was really invoked? have prior to the pandemic that now is like, wow, what are just kind of letters in it STEAM?

Jeff Cantalupo 30:07
Um, that’s a great question. I think I may be optimized my brain for looking at things for what’s continued momentum versus a Wanwan. I think, you know, man, I, it’s what was I excited about before the pandemic, I let me back up and say that we have been fortunate not to be exposed to a lot of industries or companies that got decimated by the pandemic, we invest in a lot of consumer-based e-commerce or consumer tech. And the majority of our businesses actually accelerated through the pandemic. And so, from that perspective, the thematics that we continue to be excited about are really anchored in, I think, a lot of the trends that we’re excited about pre- and have continued to be excited about post. So I wouldn’t I can’t point to anyone specifically that I was really excited about that kind of went down the drain after the pandemic.

Matt DeCoursey 31:06
I literally had multiple conversations with people pre pandemic that were like, Yeah, I’m bored. I’m done with ad tech. And then all of a sudden, the pandemic cat news, like the same people, as if we had never had the prior conversation, or like, I’m so excited about edtech right now, I’m just gonna put it all in, you know, like, wait a minute, wait a minute, wait a minute. So you never know, man, hey, but that’s the way it goes. We’re all allowed to change your opinion. I think that if you can’t pivot a little bit, then my my business partner, and often co-hosts as Matt Watson said, like, hey, the pivots my favorite move, baby. So yeah, also,

Jeff Cantalupo 31:52
you got to be flexible, for sure. And that, and I think it’s interesting one, one area that we’ve been investing in, in and around for a long time that we continue to be excited about. And it’s unfortunate, I wish we didn’t have to be excited about it, which is mental health, right, we invested in a company called calm back in 2012, when you know, meditation, quite frankly, was not mainstream, but you kind of had to squint your eyes and believe that people were going to start to spend time helping, you know, exercising their brain as much as they did their body. And, you know, fast forward to today, you know, we’re facing probably the largest mental health epidemic in history. And so, you know, there needs to be a continued focus on innovation around giving people access, access to help access to, you know, knowledge around how to take care of your mind.

Matt DeCoursey 32:50
And it’s just as important as I’ve actually written, wrote a book on the subject, you know, I, my take on it, you got three P’s, you have your personal professional and your physical life. You know, there’s no actual, like, formulaic approach to everyone, there’s no right answer, we’re all a little bit different. We all have a different set of needs. So I would be remiss if I did not ask about what or how your fund and your company look at a diverse approach to investment.

Jeff Cantalupo 33:24
Yeah, no, I think it’s a great question. And I think it’s a question hopefully everybody is thinking about in terms of diversity approach to investing, I think, you know, what we’re looking for are extraordinary entrepreneurs. And my experience Matt has that has been that extraordinary entrepreneurs usually come from extraordinary backgrounds. And so, you know, we’re, we’re constantly looking for folks that have, had had maybe more challenging times in their lives and are solving problems that they’ve seen or been through themselves. And, you know, from a, from a high level, philosophical perspective, I think it’s also just about bringing voices to the table for for for audiences. You know, I mentioned earlier in the podcast that our our name is listen, and so, you know, we can’t, we can’t sit here and try to invest in consumer brands if we don’t have consumer voices at the table that represent all different consumers. And so we’re, we’re very focused on bringing to the table both in our team as well as, you know, with with our partners, voices that oftentimes are underserved, so we can understand what’s what’s happening, what’s happening in culture, how can brands serve them better?

Matt DeCoursey 34:39
Yeah, I look at you know, I’ve made quite a few investments myself, and I say like, an entrepreneur and entrepreneurs and entrepreneur, I don’t even like the labels, honestly, like, you know, and I’ve had conversations with with some of my, the female entrepreneurs that I’m the most inspired by their Like, why do I have to be a female entrepreneur? Or can I just be an entrepreneur? Like you are with me? We’re good. So, what? Before we hadn’t? Before we round out the show and come in for a landing? What’s a quality or a trait? That will make you want to invest in an entrepreneur? And one that won’t?

Jeff Cantalupo 35:19
Mmm, um, I mean, the, I don’t know, maybe this is a cop-out answer. But like, the first one is, is belief. You gotta have, you gotta as an entrepreneur, your job is to make people believe. And especially at the early stage, it’s number one trait because you got to get here, most of the time, you got to convince people to come on this journey with you. Right, and oftentimes, they’re leaving, you know, very, very good jobs and decided to kind of throw throw things to the wind and take a risk. And so you got to you got to make people believe I think that’s a trait that I’m that I’m always looking for when I hear the entrepreneur story and why they’re doing what they’re doing, how purpose-driven is it. And then a trait that I forgot how you termed it, but a trait that maybe is a bit of a turn off, or a pet peeve I would say is, you know, any, any inclination that I get that they’re just doing it for the money, I typically get a bit turned off, right, I think I’ve had a number of entrepreneurs, and some of them gone on to be very successful. But they pitched me that the reason they’re doing the business is that they looked at 50 Industries, and figured out that this one hadn’t had a direct to consumer success story. And so they were going after that one. And that’s exciting. But it doesn’t have that the purpose or intention that we look for when we’re looking to back at an entrepreneur and tell a story.

Matt DeCoursey 36:44
I’ve asked that question to quite a few people on and off the mic, or air however you want to call it. And the best answer is also the answer for the most and the least is the same thing. And it’s, you kind of described that you believed it was just passion. So passion or lack thereof, which you kind of said, without using the word passion because a lack of and the reason for that is it gets you through, like a passion for the solution. And for the fix and to solve the problem it gets you through the times when you want to quit. And if you don’t have passion for AI, which by the way is another another trait of genius is passion. Because if it doesn’t exist, so a lot of belief that if you’re not passionate or highly interested in the solution, you’ll never apply enough of your mental or spiritual or whatever you want to call it bandwidth to solve it. So it’s a key ingredient. Now it’s time for our it’s time for our time to pretty much come to an end here momentarily. And I like to end my episode Startup Hustle with what I call the founders freestyle. I say my episodes because if you listen regularly, you know, I am not the only host of the show. While it might have started with myself and Matt Watson. We’ve gotten a lot broader than that. So make sure you tune in weekly to hear what Andrew Morgans has to say about building brands, e-commerce and Amazon sales. So Andrew is the founder of Marknology and Amazon brand accelerator and tune in for Lauren Conaway, his weekly show Lauren is the founder of InnovateHer, and they just got their 5000 member and I’m excited about that. So hopefully you’re one of them. Now with that I did the founder freestyle. Yeah, let’s give founders an opportunity to freestyle I’ve had people actually rap. I’ve had people recite poetry. I’ve had people go blank, and I’ve had hopefully people say anything that they may have missed, or what some of the key points from our conversation might have been bad or anything. I don’t know. It’s your freestyle. So it’s trying to buy you some time there. Anyway, so i Sir, I hand you the mic.

Jeff Cantalupo 39:05
Well, I’m gonna I’m going to actually flip it, Matt, if that’s okay. And I don’t know if people have done this to you. But when we have a podcast, as well called Overheard, and what we end every episode with one question, which is, what are you listening to? So Matt, I would love what do you what are you listening to?

Matt DeCoursey 39:24
What am I listening to? Well, a couple can I answer it and do my freestyle or, or is this your freestyle? So

Jeff Cantalupo 39:31
my freestyle so I’m doing it Alright, so

Matt DeCoursey 39:34
then I still get mine so what am I listening to I actually here I’ll bring it up because one of my New Year’s resolutions is to reduce my rock and roll intake because it’s high and you know, do a little did you get into the audible collection that you know, audible guilts me every month into using the credit that I forgot about so I have this like ride like here so I’ve got like 100 audibles on Listen to about 30 of them. So this morning I actually listened to the genius zone. As I mentioned, I’ve been studying I honestly part of it as I’m trying to figure out how to flip what I first thought was a switch, and then it turned into a dial. And now I’ve learned it is more of a spiral that goes up towards your, quote, genius sound. So that’s been what I’ve been listening to in that. And that’s been a part of a broader experiment that some people think is going to turn into my fourth book. I don’t know about that. Because I don’t know if I want to write another book. And then, so I listened to that. And this morning, I always listen to music in the shower. So this morning, I was listening to one of my favorite jam bands goose. Nice. So yeah, which many thinks will be the next fish. So you can make all the assumptions you want about what I do with my spare time based on that personal info. But But yeah, so they actually just played New Year’s Eve, the, I believe, at the Aragon Ballroom, our hometown, one of my favorite venues. Yeah, I actually wrote a book with one of Chicago’s most well known jam bands with one of their members from unfreeze McGee. So I’ve been I’ve been been to Chicago on many, many occasions, usually, for that now, for my freestyle. Yeah, yeah. I think there’s so there’s, I think there’s a few, I always like to I can lean back on, like, what stood out. And, you know, I enjoyed our conversation about Brant. And basically a brand exercise as opposed to building a brand, you know, a brand can be your appearance, but branding, and I don’t know, like, try to create something valuable, I think is the main thing, I think you’re building a brand when you’re creating something that, you know, that people have an association with. And I know for a fact that we managed to do that at Full Scale, because I get a ton of referrals, and you don’t get that kind of people don’t point stuff in your direction if they don’t feel good about it bad of themselves. So and I think the thing is, I turned 47 This year, and I don’t look a day over 46 Currently, so but with that I’ve really, really felt that. You know, like I said, as I’ve grown older, and I’ve matured, I’ve really feel that that a good brand creates that peace of mind. And I think that peace of mind is it? Well, first off, without it, nothing else has much flavor spice. And it’s really like an intangible thing that you can’t really put a value on. So like, giving people back their time or their peace of mind is inherently valuable. And I and you know, 10 years ago, I looked at something like GigaBook, or the different things that I’ve worked on. And I’m like, you know, our real value is the systematic and formulaic approach to who cares about peace of mind. And it really is, and it’s like the same thing. It’s like, you look at any of the brands that you draw and associate quality with, well, that’s a peace of mind, that’s knowing that whatever you’ve got isn’t a piece of crap when you get at home. And I think if you focus on that, and and you know, also like, you know, service, remember, you sell stuff, largely because you will on a bid on a b2b approach. It’s because you either help people sell more, spend less, right? Or give the business owners or the people that are peace of mind. That’s right, which is actually probably more valuable than either the other two I mentioned, because these are the people that continue to make the decisions about what you’re buying. And so, you know, like, I don’t know, I think really, that’s, that’s been a main thing for me. And, you know, and I appreciate the approach to I think lesson, you know, hasn’t always been hasn’t always been something that I can be verbose. You know, I’ve learned the power of listening. And like you said, it’s like, when you get people to come in and experience your whatever. They’re usually telling you what they want to buy, how they want to buy it, at what volume, what they haven’t bought in the past, and why. And the more you listen, the more you get into, like, I don’t know, the best. We interviewed a new salesperson today. And we literally the first thing we talked about is is he a good listener?

Jeff Cantalupo 44:12
Yeah. Yeah, it’s an incredible trait. I think there you could dedicate a whole series of podcasts around how you can become a better listener for sure.

Matt DeCoursey 44:23
And maybe we’ll just do it. We’ll just do it and just be quiet the whole time and see how that goes. And that’ll be like a, that’ll be a by the way, are you interested in what the traits of genius are?

Jeff Cantalupo 44:34
I I’m super interested in I love that you’re studying it. So this so by

Matt DeCoursey 44:39
the way, I’m studying it because I want to learn how people turn it on and off. And I start I began my study by literally talking to rock stars, which I have this like I worked in, I mentioned working in the music industry. I have like a member of Dave Matthews Band, wrote the foreword for my music industry book. Oh, amazing. You know, so well, you Have some get some access to some interesting people but and so it started out with me wanting to know how do you turn that switch on? I’ve also learned that a lot of that is really just preparation and the inspiration occurs in other moments, not just the what you see on the stage. But so there is a there are 24 Slash 25 things that that most people agree on and they are Dr. courage, devotion to goals knowledge, honesty, optimism, ability to judge meaning like they don’t cross something off before they look at the facts and like you’re not saying Oh, no, my bad personal view or opinion says that won’t work. So they’re very, very open. And through Shazzam, which is kind of what you were mentioned, if you don’t have the power to move people you’re not, which goes to the next one. dynamic energy, they’re willing to take chances. Enterprising, persuasive, outgoing, they have the ability to communicate. This is an interesting one, they are patient with others most of the time, but almost never with themselves. Perception, perfectionism so geniuses cannot tolerate mediocrity, particularly in themselves. Sense of humor, versatility and adaptability, curiosity, individualism, you are not concerned that anyone else cares about whether what you’re doing has any merit at all. idealism and imagination. So I love that. Yeah, so apparent. Now the interesting thing is, is with that, what I found is that people make the mistake of believing that geniuses are born and not made. Those are all things I everything I mentioned, is something you can get better at. That’s for sure.

Jeff Cantalupo 46:52
The one that stands out to me in that list, Matt? Is that is honesty.

Matt DeCoursey 46:58
You know, it’s and some of that’s like, it’s it’s being open with others. And also like, honesty to well, sometimes you’re you’re pursuing the wrong shit. Yeah. Yeah. Pretty simple. So you know that? Yeah. So anyway, we’ll see where we go. And like I said, that really has evolved. It went from thinking it was a switch, and then it was a dial because you kind of turn it up and then like that spiral is because there’s so many dimensions to everybody. That’s never a flat landing or surface. It’s funny, because as I’ve progressed down that I’m like, Oh, wow, of course, it can’t be a switch. It must be a dial-up. Oh, no, that’s too lenninger. So who knows? Talk to me again in a month, and I’ll probably have like a weird matrix or something for it. I don’t know.

Jeff Cantalupo 47:40
Wait, I’m waiting for the episodes when you’re dissecting the geniuses of our time.

Matt DeCoursey 47:45
And for those of listening once again, Jeff Cantalupo, Founder and Managing Partner Listen Ventures go to See you next time.

Jeff Cantalupo 47:54
Thanks, Matt.