Jackie DiMonte of Chicago Ventures // ascending the venture career ladder and opening an office in Austin [CC071]

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Eric Hornung 0:00
Jay, what’s your favorite podcast app named after a fruit?

Jay Clouse 0:05
Gotta be Apple.

Eric Hornung 0:06
Can you think of any other ones?

Jay Clouse 0:07
I tried really hard. But I didn’t want I didn’t want to wait for too long. I didn’t want too much dead air.

Eric Hornung 0:12
Hey, you know what’s worse than dead air, not getting reviews on Apple podcasts from your listeners.

Jay Clouse 0:17
Oh, my gosh, it is the worst every day that I wake up and I don’t have a new review on Apple podcasts. I just look up in the sky. And I go, aaah,

Eric Hornung 0:26
I like how the first thing you do when you wake up is to look at Apple reviews.

Jay Clouse 0:29
If only I was lying, but I’m not. And I’m looking for new reviews for Upside on Apple podcasts, Eric and if you are listening to this right now, you could be that person that helps get the day started right.

Eric Hornung 0:41
All you have to do is go to Apple on your iOS device or web browser, plug in and leave us a review. Five stars would be nice, four stars would be great. Let’s do five stars.

Jay Clouse 0:52
Let’s do five stars definitely prefer five stars. Even if you don’t use Apple podcast as your preferred listening app on an iPhone, please take a moment to rate us there. Anyway, it helps us bring on great guests. It helps us climb the charts. Our show will get better if you do this very simple act. So please, please.

Jackie DiMonte 1:10
Some of the folks at Chicago Ventures are some of my you know closest friends kind of on and off the field right like we grew up in venture together. I know that I trust them and have gotten to know the the existing partners at Chicago Ventures over time as well.

Jay Clouse 1:28
The startup investment landscape is changing. and world class companies are being built outside of Silicon Valley. We find them, talk with them and discuss the upside of investing in them. Welcome to Upside.

Hello, hello. Hello, and welcome to the Upside podcast, the first podcast finding upside outside of Silicon Valley. I’m Jay Clouse, and I’m accompanied by my co host. Mr. Soon to be home owner himself, Eric Hornung.

Eric Hornung 2:08
Whenever you do something, Jay, I always have to follow. That’s my rule in life. You buy a house, I buy a house.

Jay Clouse 2:15
You just want to see how it works out for me first, just to make sure that it wasn’t a mistake.

Eric Hornung 2:18
Yeah, you’re my you’re my life guinea pig. We did buy a house though. We are in the process of closing on that right now. We went through inspection and appraisal and all the fun stuff that goes with buying a house. And yeah, just very excited about actually having a place to live for more than 18 months since I haven’t done that since I was 18 years old.

Jay Clouse 2:40
Really? You’ve been on the move every 18 months since you were 18.

Eric Hornung 2:43
Technically in college, I had two years in the same house. However, the entire summer I wasn’t there. So does that really count? I don’t know. But if there’s a there’s an Asterix on that 18 month quote. But yes, generally.

Jay Clouse 2:57
Well, the people want to know. Are you moving out of Cincinnati?

Eric Hornung 3:00
No. I’m staying put staying here in Cincinnati. We’re actually moving a couple streets over from where we live right now. Yeah, I’m I’m pretty excited about it. It’s an old house from 1910 as everything in this neighborhood is it’s got a beautiful backyard for Hank to run around in. It’s got a fireplace for you and me to sit around and drink whiskey in front of. Yeah, very excited about it.

Jay Clouse 3:18
It sounds like you’re really taking some steps to make sure that you’re living this one life. You have to live the best way that you can.

Eric Hornung 3:23
Well, it’s because I’m always talking with our friends at Ethos Wealth Mmanagement, who are helping you live that one life you have the best way you can, you can learn more at upside.fm/ethos.

Jay Clouse 3:32
Well speaking of big moves, today we’re talking with Jackie DiMonte, who just made a big move, going from Hyde Park Ventures to Chicago Ventures where she is now a partner. Prior to joining Chicago Ventures, Jackie worked with portfolio companies such as RoadSync, Podchaser, Fixer, FactoryFix and PartySlate. And before that she worked at Silver Spring Networks, an IoT company for critical infrastructure, driving development and pilot projects for emerging smart city technology. She’s a member of Partner at Republic. Eric we’ve known Jackie a little bit for a while now one of the few folks on Upside that we talked to off air before we talked to on air.

Eric Hornung 4:14
It was back when we were doing that hey, let’s network everybody thing and then realize that oh, we record a podcast to to do that. So it was a weird time. But I’m glad that we’ve gotten a chance to bring Jackie back on the airwaves. Well, back on our internal airwaves I guess for all you listeners. Wow. That was a stumble through huh.

Jay Clouse 4:35
That was sloppy. Chicago Ventures was launched in 2012 to fill an acute market gap at time early-stage capital flowed as if innovation were restricted by geography. So Eric, a firm that we certainly aligned with filling a geographical gap.

Eric Hornung 4:51
With a name like Chicago Ventures Do you think okay, we’re just gonna focus on Chicago, but I love the Jackie’s in Austin and I can’t wait to dive into that. Kind of Hey, where Chicago versus we don’t just invest in Chicago.

Jay Clouse 5:04
Yes, another big move of its own right. She lived in Chicago for quite some time even going to Booth the Chicago School of Business now living in Austin, Texas, enjoying all those tacos that you and I have also shared at our time at South by Southwest.

Eric Hornung 5:18
You know what the best part about Cincinnati is? I found a taco place that is reminiscent of Austin just yesterday.

Jay Clouse 5:24
I saw the photo and I was like, is Eric in Austin, and I thought Eric’s not Boston.

Eric Hornung 5:28
Well, I’m gonna be from a mental perspective in Austin a lot more because that place was fantastic.

Jay Clouse 5:34
So we’ll be talking to Jackie about the move from Hyde Park to Chicago Ventures, I have some questions generally about climbing the ranks within venture that we’re going to ask, we’d love to hear your thoughts on this episode. As you listen, you can tweet at us @upsideFM or hello@upside.fm. And we’ll get to that interview with Jackie right after this. Eric, we got to make some big changes to how we do operations here at Upside.

Eric Hornung 5:58
This feels like an intervention Jay.

Jay Clouse 6:00
It’s a bit of an intervention, I have to give you some tough love. We’ve had some calendar problems over the last couple of weeks.

Eric Hornung 6:05
I’ve had some calendar problems, you don’t have to throw the third person on this.

Jay Clouse 6:09
I do like to take the blame for you. But this one is on you. And Eric, I think we have found a solution to our calendar and scheduling problems.

Eric Hornung 6:16
But there are 101 scheduling tools out there Jay that can help you avoid the awkward dance of finding a time to meet.

Jay Clouse 6:22
But this tool is by far and away the best one I’ve seen. And I’ve looked at a lot of scheduling tools. And I am talking about SavvyCal.

Eric Hornung 6:31
SavvyCal makes it a collaborative effort allowing you to personalize links and allow recipients to overlay their own calendar on top of yours.

Jay Clouse 6:39
It’s going to make booking guests for Upside and even just one on one conversations a complete breeze, you got to see what this looks like you got to see how it works. Because you’re going to ask why wasn’t it always this easy?

Eric Hornung 6:50
You can sign up for a free account at savvycal.com/upside. That’s savvycal.com/upside. And when you are ready to test out a paid plan, use the code Upside to get your first month free.

We like to start on Upside with a background of the guests. So can you tell us about the history of Jackie?

Jackie DiMonte 7:21
Sure. Where should I start?

Eric Hornung 7:24
That’s the that’s the million dollar question.

Jay Clouse 7:25
And it’s also purposefully ambiguous so that you can choose your own adventure.

Jackie DiMonte 7:29
Yeah, well, I’ll start coming out of undergrad because everything I did before then I just can’t can’t remember anymore. started my career in Accenture, which is all I’ll say about that, because it was a ton of fun and got me ready for the real world that was not my permanent job. joined a company called Silver Spring Networks, we were in the IoT space, the company primarily sold to utilities when I joined. So we created the infrastructure for smart devices, you’d put them in smart meters or distribution equipment. And my job was bringing that core technology into the smart city space. So I worked with a lot of different companies, everything from you know GE all the way down to kind of series A B funded startups trying to integrate either our physical, you know, mix network chips, into their products, or our backend software into their analytics or other applications. So I had a really fun time at that I was running a small incubator, technology incubator, not not startup incubator, the way we think about it in the venture world. But really, really interested in new markets and applications and different ways of bringing product to the real world. That’s what I initially got interested in the venture like experience, I had no finance background, I was going to Booth. So University of Chicago’s MBA program on the weekends at the time. And that’s, that’s when I started to get a little bit more of exposure to what is venture capital, you know, what are these different career opportunities. And I started to see this convergence of technology, which I was really, really excited about ever since, you know, studying engineering in undergrad. And then this cool world of finance where outcomes were measurable. I really liked that about venture and, you know, most people get into venture they’re like, Oh, I love entrepreneurship and startups and I want to go hand in hand with founders and like, I did not know that was the thing before getting into it. And I love that now but I was like, Oh, you mean I make a decision and then there’s an outcome that I know what it is. And I thought that was really interesting because in all the all the roles I had before that, you know, you you do a good job as a high performer and everyone pats, you on the back and you’re like, well, I put either 100% of my effort in that or 50% of my effort, and you guys didn’t know the difference. And so I really wanted one of these jobs where like there was there was real outcome on the line. I definitely under appreciate that it takes years and years and years to understand what that outcome is, you know, I’m still still waiting for those measurements. But anyway, that’s what initially drew me in, I connected with the folks at Hyde Park through an event at Booth to the my first exposure into venture capital, I had some friends that were had entered a venture capital competition. So it’s like a reverse, you know, business plan competition, they needed someone with technology experience, because they were all, you know, sort of finance background, I said, Sure. And then I bought venture deals, and started following a bunch of blogs. And during the, during the competition is how I met a few of the partners around the Chicago Venture ecosystem started talking to them about internships that, you know, eventually turned into a full time offer from from Hyde Park. So that was my first foray into into venture capital.

Jay Clouse 10:57
Were these internships, things that they were advertising? And were recruiting for? Or did you kind of create that opportunity for yourself?

Jackie DiMonte 11:05
A little bit of neither, but kind of both. So what happens with MBA programs is they have this class and like most MBA programs have like a venture capital class, where you then go interview with a bunch of venture capital firms. If you get chosen as an intern, you get to attend a class, and it’s a 10 or 12 week class internship combo, I was not recruiting for that. And they weren’t officially posted applications. But it becomes this little side network of, you know, where the matches come from. I was also working full time. So it was one of these things where I was really interested in getting to know VCs, because I thought that was eventually where I wanted to go. But I was not so risk seeking at the time that I was, you know, quitting my job and going after these internships, in hindsight, you know, that’s probably something I should have done. But I just didn’t know. You know, that was how the world worked at that point in time.

Jay Clouse 12:09
So you were still Silver Spring at the time?

Jackie DiMonte 12:11
I was, yeah.

Jay Clouse 12:12
Did your experience with Accenture and or Silver Spring have a big impact on Hyde Park’s interest in bringing you on?

Jackie DiMonte 12:21
I think that Accenture had some impact. You kind of know, when you get someone who went into consulting, that they can work hard, and they probably have some sort of intelligence. But it’s not it’s not differentiated. And I say that with thinking it was a great experience. And knowing it was a great experience. For my first first job out of college. I think the real key was at Silver Spring, it was during this peak hype cycle of IoT, when everyone was like, ah, connected devices, smart home, manufacturing, you know, like they it was just everywhere, and I think me being in the industry and being able to speak credibly, you know, create my own perspective or thesis about what works, what doesn’t work, I think that showed that I could take a very large topic. And it was very hard to understand, right, because as hardware, middleware, network software, various different business applications, and very neatly put them into categories of this works, and this doesn’t work. And it helps that some of the companies had pocket invested in in the space, I could kind of tell them if they were going to work or not, as they were on that path. So I think there was some, you know, some benefit to really having experience in this space. But it’s something that I would urge everyone who’s interested in getting involved in, in venture is to find that thing that you can create perspective on, and really show that you can apply forward thinking to it.

Eric Hornung 13:54
You’ve mentioned indirectly this idea of a feedback loop in what you’re doing. He said, it takes years and years and years in venture. And so often we hear that don’t join venture capital if you want, like instant feedback on something because you don’t actually know if you’re good at what you do for 10 years. How do you think about the like juxtaposition of not knowing if you’re good at something for 10 years in venture versus working with founders who need to know if they’re good at something like daily?

Jackie DiMonte 14:20
It’s super interesting, because the feedback loop for if I am a good venture capital is measured by returning capital to investors. But in the meantime, there are all of these little wins and losses along the way. And somehow you have to take those mini feedback loops and turn them into slightly bigger feedback loops, which then hopefully drive your very long feedback loop. An example might be, I think that product lead growth, you know, should be measured using these metrics. And so I work with the founder to do that. And then I work with the next founder. And then I learn a little bit along the way and help all of the other founders apply those learnings. And then that creates a larger feedback loop, which is, you know, we invest in companies that go to market using product led growth and have these core metrics. And so then that’s that slightly larger feedback loop that drives your activity along with helping founders activity. And then hopefully, that drives the very long feedback loop of those types of companies create massive value for our investors. And so that’s, that’s what keeps, I think, engaged, or a lot of us engaged on a daily, weekly, monthly, whatever basis because there’s so many, many lessons to learn along the way that keep the feedback loops growing.

Eric Hornung 15:48
It’s like feedback loops all the way down.

Jackie DiMonte 15:50
It’s like inception.

Eric Hornung 15:52
If you how do you dive in and out because it’s so hard to stay high level, low level and be jumping around all the time? What tactics have you used in your venture career thus far to successfully kind of jump around the different layers of that inception.

Jackie DiMonte 16:07
I try to structure my days with different levels in mind, meaning Tuesdays and Thursdays are my days to just talk to a lot of people learn a lot of stuff execute, really focus on maybe those many feedback loops. And I try to keep Mondays more open Mondays and maybe Wednesdays, to figure out, you know, is there a certain area I want to be focusing on? How do I think about these companies I just spoke to are their key questions I’m digging into. And then ideally, Fridays are for that really big thinking of, you know, talk thinking about where you are in the portfolio lifecycle on the model, and, you know, different, forward looking things. It doesn’t always work out. But I try to really tease out those themes so that I’m never stuck just as a little hamster on a wheel trying to keep in those small, small, tiny feedback loops.

Eric Hornung 17:07
It’s fun to think that a hamster has on a continuous feedback loop.

Jackie DiMonte 17:12
It’s also very depressing.

Jay Clouse 17:14
Yeah, he’s just he’s just like a content creator, essentially. So Jackie, when when you got the role at Hyde Park, which sounds like you started as an internship, by the time you’d left, you were a principal. So talk to me about that evolution, and what that looks like inside of a venture firm.

Jackie DiMonte 17:30
Yeah. And I will say I started at Hyde Park as an associate. So we had originally talked about an internship. But because I was working full time, I kept delaying the conversation. And over that period of delaying the conversation, we got to know each other really well. And the team offered me a full full time job. So again, one of these things where it’s not not super repeatable of a process, but one that worked out in my favor, obviously. So your question is, you know, how do you grow up and adventure find in what is it like, and it is different than any other job I’ve had in that every other job. And I assume this is a fairly standard thing, you start the job, you’re like, I don’t know what I’m doing. Right? The first month or two, you’re trying to add value, but really, you’re just learning who everyone is, what the processes are, what your goals, you know, what your goals are, what you’re supposed to work on, all of that kind of stuff. And then in the first six months, you figure it out, and you know how to do your job. And then in the second, six months, you just do your job really well. And then in the second year, you’re spending all your time saying, okay, what’s next? I want to I want to do something bigger, bigger, better, whatever. venture that is so elongated, you know, going back to this feedback loop thing, the first couple months, it’s drinking from a firehose, you don’t know how to introduce yourself as a person, you don’t know how to introduce yourself as a fund. You don’t know what questions to ask. You don’t know different terms, or what who the portfolio companies are. I mean, I’m going through this right now it Chicago Ventures, I just joined Chicago Ventures a couple weeks ago, I knew the portfolio companies, but you know, I’ll use I’ll use air quotes because we’re on a podcast. I didn’t know the portfolio companies, right. And so there’s just so much to like their LPs, right? You need to know who your LPs are. Because how embarrassing is that? To go up, introduce yourself, and someone’s like, Oh, yeah, I know you because I invested in you. There’s just so much to learn. And that can be pretty uncomfortable for someone who’s used to getting up to speed relatively quickly. So I probably spent the first six months just desperate to do anything right. And the cards are kind of stacked against you in the beginning. You don’t have a network, you don’t know what a good company looks like. They’re just all of these things that you have to learn and put together. So I probably spent the sit for six months just like stressed out, in my mind, trying to not get fired from my job. So that was fine. You learn a lot. And I don’t say fun sarcastically like it. It is fun in hindsight, because you’re just, I mean, you literally are drinking from a firehose, you know, after that, you get your feet on yourself, you say, Okay, I know how to build a network, I need to go build my network. I know how to source companies, I need to go source good companies, I’m learning how to get a deal through the deal process, let me keep pushing that through. And so you just start to figure out how things work, and then get better at better at making those different things work for us. You know, we have all of these different levels. at Hyde Park, it was, you know, associate senior associate, VP principal and and there’s partner, I got promoted through each one of those phases up through principal. And really, what the difference was, is the confidence the team has on you to execute things independently and support the overall firm brand. meaning you’re not going to bring on someone right out of, you know, right out of school and say, Hey, why don’t you go be a principal, and then never give them the support to get any deals done? Right? Because that will confuse entrepreneurs, maybe give them a bad experience, you might lose out on on good deals, because the individual doesn’t know how to get through the deal process. So for us, I think that that evolution or growth within the company was really about, you know, yes. Are you good at your job? But also, what are the things that you can do independent of, you know, someone else on the team that makes an impact and makes us you know, a better brand in the ecosystem?

Jay Clouse 21:46
As you go up the chain in venture like, at what level? Is it on you to do deal flow specifically, you know, in source these companies, and I imagine you have the opportunity at any level, but I wondered if the explicit expectations changed at a certain point.

Jackie DiMonte 22:02
Yes, and no, so depending on event how venture fund is structured, sourcing falls on different people, there are some venture funds, especially growth stage venture funds, where their analyst associates, all they’re doing is sourcing, just picking up the phone call picking up the phone, calling emailing someone looks a little interesting, they pull someone else in into the deal. Hi, Park was a small team, but we actually functioned. Similarly. And when you think about it, when you join as an associate, you’re not working on any boards or with portfolio companies, you’re not working with LP use. And so you have all this time on your hands to source and diligence companies. So that’s really what I did in the beginning, it was like you need to source the expectation is not that you bring the deal from, you know, zero to close. But the idea is, you become that front end, right, create a lot of activity, the partners will leverage their networks, you do a lot of outbound start to build your network, yada, yada, yada. There are some times where the junior folks are here just for diligence. So a lot of times the partners will have very established networks, they’ll bring in a deal, they’ll have a junior person assigned to it, our firm was not not necessarily like that, except for, you know, we would all form deal teams and work on things together, I would say somewhere between, you know, Senior Associate and VP was when the expectation was you should be sourcing, bringing companies in driving a diligence process, and working with them after after investment. So I got involved in my first boards, as a senior associate, for example, you know, once you kind of become Vice President, Principal, Director, you know, different firms have these different names. That’s when your like partner and training, you should be sourcing companies, you should know how to get a deal through a process, you should know how to work within the firm to you know, gain consensus, understand how people feel about it, and then certainly help companies after you know, the investment is made. Ideally, you’ve had had a few reps at it, and you’re not going to totally, you know, totally mess things up.

Eric Hornung 24:17
You’ve mentioned get a deal through a few times now. I’m believe you’re talking about investment committee and getting buy in from the decision makers at the firm. Can you talk a little bit more about that experience across the gambit of analysts, the partner and I think you have an interest in art. So is it like more art or science when it comes to actually getting a deal, finding a deal and then saying, okay, we’re going to make this investment.

Jackie DiMonte 24:44
It is all art, which can bother me sometimes because I am also very analytically driven. I would say this is one of the hardest things for me personally, and it’s something that I have worked on and certainly will need to work on with the team at Chicago Ventures, especially because we’re, you know, we’re working together for for the first time on some of these things. But you, you really have to understand how people feel about the companies that you want to work with and want to invest in. Part of that is because just tactically, if you’re in a firm that votes and need X number of votes to get, you know, deal across the line, you tactically need that to happen. But also, you just want to know what your blind spots are. A lot of us investors, and I have this belief that you know whether or not you want to get involved with the company kind of the first time first or second time you meet with them. And then all those subsequent meetings are just proving yourself right or wrong. You need to pull in other people to look at your blind spots, and make sure that you’re not discounting some things just because you’d like the team or the idea or whatnot. The problem is, is that not everyone looks at companies through the same lens. And so there are times where I just want to beat people over the head with data and say, Look, you don’t like the market here. The markets big enough, I did the math. But in reality, you need to tease out what are the questions? Why do you not like the market? You think it’s small? You know, what, what might change your mind? There’s, there’s a lot of art to it, you need the science to back up opinions that you have, right. Otherwise, they’re just opinions. But certainly the process is much more art than science.

Eric Hornung 26:35
Do you think that programmatic venture has a place in the future?

Jackie DiMonte 26:40
Yes, I think that programmatic venture is very interesting, if you have a fund structure to support it, meaning I think there are a lot of index funds that are programmatically driven. And I think that makes a lot of sense index, meaning, you know, I write smaller checks into a bunch of companies, there are probably going to be places for those funds that are more concentrated positions, especially if you think about the pure SAS vertical, like there’s some metrics that if you have a say, You’ve really good retention, so you keep your customers and your customers grow over time. You know, you can probably tease out some of those key metrics that you think make a difference and leverage that for your decision making. The part that I get scared of with ai, ai driven investing, programmatic investing, is there might just be companies that none of us think of right now, that could be interesting. And there’s no precedents for how to interpret them. Or think about people and and founders, if we use a biased set of data to train our algorithms, and and i mean that both by demographics, but also by experiences, we can miss a lot of the, you know, crazy out of left field, high impact companies. And so I think there’s there’s a place for both in the future. I think programmatic is really interesting. I think a lot of firms that are still people driven have elements that they rely on for that, but certainly you gotta leave space for the crazy ideas.

Jay Clouse 28:15
When you were at Hyde Park, how often were you co investing with Chicago Ventures? It seems like both being in Chicago you must have run in similar circles pretty often.

Jackie DiMonte 28:26
That’s right, there were at least a handful that we invest co invested in while I was on the on the Hyde Park team.

Jay Clouse 28:35
And so now moving on to Chicago Ventures from Hyde Park, how has your world or role changed.

Jackie DiMonte 28:44
This is a funny thing because my role has not changed very much. If you look at VCs we all kind of do the same thing you know we all source we all do diligence we all work with companies after after we invest and so inherently my job is a team job kind of regardless of of where I am, you know the firm’s have slightly different theses. So Hyde Park was was hyper geographic focus on the Midwest and then you know, parts of Canada primarily Toronto, Chicago Ventures is a little bit wider it’s you know, non traditional coastal areas. It CB we also focus exclusively on the seed stages that could be you know, kind of pre seed seed post seed anything that’s really early versus at Hyde Park, we’re kind of flexing from pre seed all the way up to A. So there, there are slight differences in the focus. The only way that really changes my job is that the companies I’m looking at, I have to be much more deliberate at Chicago Ventures because if I miss a seed stage company, I probably don’t have access to them afterwards. And so it’s it’s slightly just In the way that you think about leveraging your time, and how to make decisions a little bit quicker, and with more confidence, when there’s less data you don’t, you don’t really want to just like sit back and wait. That’s, that’s probably the only the only thing that’s a major difference. I will say, I came on to Chicago ventures, and I was gung ho to just get going, right? I know how to do this job, there are companies that I like, you know, I’m excited to go, you know, refresh my network. And then I joined day one, and I’m like, Oh, wait, things are done differently. Like, I’m still gonna have to learn, you know, how to interact with a new team. And even though they are very supportive and excited about me bringing new process, new workflow, new ideas for the team, I still have to be sensitive to, you know, let’s not be a total bull in the china shop, and just kind of, you know, wreck havoc, I still want to build those relationships and understand the workflow and kind of the DNA of the firm. So I’m sure if you ask me that same question. In two months, when I have a better feel for everything, I’ll have a little bit more of an expanded answer. But the basics are, you know, we all do kind of the same thing.

Jay Clouse 31:13
And I know that you’re in Austin. Now, I think you’re the only Chicago Ventures person in Austin. So right off the top of my head, the first thought I have is, I wonder what that what that’s like, as far as getting support from the team and representing a firm called Chicago Ventures in a city called Austin. But we’re in a unique point in time where I realized a lot of things were probably done virtually for the last year anyway. And things may have changed. So this isn’t really a question so much as an invitation to talk about, what does that look like for you, as far as team support and talking with companies being that one person from the firm in Austin?

Jackie DiMonte 31:53
Yeah, I’ll start with team. And right now, it’s really simple because we live in a highly virtual world. And so the interaction is the same. Me being here as if I was in Chicago, or Denver, or Columbus, right? The difference is, I can’t go on walks or start to build some of that one on one time, which I do find a lot of value from, you know, the the walk and talk, you don’t really need an agenda, the Xoom call, you kind of want to have a purpose to it. And so I do feel like could be missing out on some of those elements. But with everyone being on video, it feels very natural. And I do feel like part of the team, it’s easy for me to get in the flow of things. I am interested to see how things change, when we start to get back in person. It’s something we’ll have like a bridge, we’ll have to cross when we get there. I have been, you know, the person in a different city, when we’ve been in person. And it can be hard if everyone else is in person, and you’re on video. So there are probably some structural things that we’ll tease out along the way that just keep communication open. Now, when you think about why I was hired, and why is hired being in Austin, is because this is a very strategic city for Chicago Ventures. Austin has been growing from a startup ecosystem perspective, we have made a handful of investments here already, I have a very deep network in Atlanta from my previous investments. And so there is this brand to build and this access to build across, you know, the Texas and South East ecosystems that I think are still overlooked at the seed stage, you know, kind of still fits the core thesis that we had 10 years ago of supply, demand imbalance, and really being able to be that strong lead at an early, early stage. And so for me working with a team, the expectation is like you go out and do it. And so from that perspective, it is very helpful to be somewhere that’s different than everyone else, because I can have those face to face interactions, I can build those relationships. And as much as we all have, become efficient investors on zoom. There is really nothing like sitting down at a table with someone and just knocking out different diagrams on a whiteboard, right? There is something special about really digging in, in person and there’s going to be an advantage to me being here versus having to fly out to Austin or to Atlanta or anywhere else on you know, a quarterly basis, something like that. You know, from a branding perspective. It is kind of interesting. You know, I get on the phone with people and they’re like, Okay, are you in Chicago? Are you in Austin? Like what’s going on? Are you one of these like COVID people that just, you know, came down for the winter like are you going to be back in Chicago in a couple of months. So I think there is there is still a lot of work to be done on the Hey, I’m here. I’m here to say, I love the ecosystem. I’m here to support it. But I think that’ll come with time. Right? If If I’m still doing coffee meetings, when it’s 160 degrees in August, I think, I think I’ve proven my worth as a, as a local, local investor, but you know, well, we’ll have to get there overtime.

Eric Hornung 35:27
One of the things that had to be exciting about joining Chicago Ventures was getting the name partner in terms of your title. Can you talked about what it means to be a partner at a, I feel like most of the people we talk to our partners are ones who went off and started their own fund. Very rarely is it? Hey, I went and joined a fund that’s been around for a decade. Can you talk to us about just what that decision was like, both from your side and Chicago Venture side?

Jackie DiMonte 35:52
Sure. And I think I think what’s interesting about my coming on as a partner in Chicago Ventures is they’re just, there hadn’t been that many, exactly what you said, There haven’t been that many people who did it. And I think part of that is we just haven’t had a turnover yet in the funds that were started in the Midwest, right? Like, a lot of these signs are on the second or third, maybe fourth, like I think origin is probably the one investing out of their fourth fund. But that’s not enough time to really have to do some promotions, and generational planning and things like that. And I think that’s why you see a lot of spinouts is because the founders of these funds, like they’re not, they’re not ready to really give it up yet. Not that that our partners at CV are giving anything up. But you know, it’s just, it’s just different perspective. Like, if you have not yet reached the point where you are comfortable, and you have a full stack team of partners anyway, a lot of these more junior folks will say look, the writing’s on the wall, I got to find a find a place to carve out my my own thesis and investing and perspective. And to be quite honest, I considered, you know, doing that as well, whether it was last year or next year or five year, you know, five years from now. And I talked to a lot of people who did it, right. And they have overwhelming feedback, which is really love that I did it, but it’s freaking hard. And I don’t know, if I would have done it. If you told me it’s gonna be this hard, you know, going going into it, it’s kind of like what every founder says right there, like, I knew I was gonna be hard, but I didn’t know is gonna be this, this hard. And so really, what it came down to me was, you know, I want to be a part of a firm where I can own something, I want a seat at the table, I want to just do deals, right? Like, that’s what I’m in it for, how can I be in a place where I can just execute. And then people is really important to me. And some of the folks that at Chicago Ventures are some of my, you know, closest friends kind of on and off the field, right? Like we grew up in venture together, I know that I trust them and have gotten to know the the existing partners at Chicago Ventures over time as well. And it just felt like a great fit. So there was this combination of things coming on as partner was really important to me, because it signifies externally, that you are there to execute. And that’s, that’s really important, it can be a very symbolic thing. As in, you can have principals or even senior associates who have just as much clout internally as a partner does, they are able to get deals done, their opinion is trusted, they are supported. I mean, I felt that way at Hyde Park, I could get, you know, I could work something across the line. But to me, the titles feel very externally driven, and as a signal to the marketplace that, you know, I can trust you and you say you’re excited that you’re going to start pushing on, I might be half, it’s a little bit exciting with meaning a little bit exciting, because it makes my life easier externally. But it was a great, you know, great position to be in.

Jay Clouse 39:10
You talked about this external signal. And there was a lot of buzz around you taking this role as a partner at Chicago Ventures. And that also feels a little bit like an external signal of, Hey, I can make financial decisions on behalf of like investing in companies. I imagine that was a lot of inbound messages then. So how do you how do you approach that and parse through that especially, you’re not only fielding all that, but you’re starting a new job and you’re learning the ropes, you’re doing this new dance of new LPs and new partners and new processes and things. How are you navigating that?

Jackie DiMonte 39:44
Slowly. No, I should I should be faster to respond. But what’s interesting about the position that I am in and the firm I’m in is I feel very comfortable, much more comfortable with my gut maybe than I did two or three years ago, and certainly when I started venture, right, if I had 10 inbound emails as a senior associate, and I don’t mean this from a title perspective, just from my experience, I would go deep into every company before I felt comfortable not taking a meeting, or I would air on the side of taking a meeting, just in case, right, like, just in case, there’s something interesting. Now I just make out a lot more part of that is I’ve seen a lot more companies and I’ve interacted with a lot more founders. So there are some ideas that are just out there, and everyone has them. So you feel much more comfortable saying like, okay, yes, I like this idea. I have, you know, these, these are the key questions that I usually ask, maybe I’ll just ask those in an email and try to start a dialogue where we don’t have to, you know, waste waste time before we figure out if there’s a there there, there are ideas that are just, you know, those out of left field, really interesting, hey, I have no idea if this is gonna work or not. But you seem cool. I have literally never heard of this thing before. So like, let’s, you know, let’s just jump right in and get a phone call. And then, of course, there are some that are sort of in between, right, they could be interesting, they might not be you take some time to parse through it. What’s amazing is I can send that to my team members in the way that my partners to do it to me and say, like, Hey, what are your thoughts, and you just, you just can go back and forth a little bit. And, you know, just triage faster, faster that way. What’s nice about being a partner, and this, again, is totally externally driven, is when you say something people take you at word, if you’re a senior associate, sometimes you get those jerks who you write them an email, you put a lot of thought into it, you know, you have a reputation to build, you don’t want to mess things up. So you send an email, and they go around you and and follow up with your partner and you’re like, come on, dude, you think we don’t talk, you know, or gal, you know, there just tend to be were more dudes doing it. But you know, it’s, it’s nice, because, again, all external signaling, it means nothing from an internal support, or how smart you are, or if you can make good decisions. But it’s nice, because you can, you can just kind of work your way through things and let it all stand. And I think that’s helpful from a confidence perspective. I mean, it shouldn’t take that to be confident in your responses. But I will tell you just a little bit of empowerment. And you can kind of get through things a lot, a lot quicker.

Jay Clouse 42:43
Part of the reason I ask is because you know, Eric and I are doing a relatively low stakes thing here with the podcasts, we get a lot of inbound pitches. Most of the people we have on the show are people we either reach out to find an intro to or are given an intro to. And I imagine in a world where you’re actually getting people money and not just an hour of airtime. It’s even more extreme than that. And I would assume that a lot of the deals you get into actually, I’d be curious to ask you this, of the deals that you’ve worked on. What percentage would you say were like inbound came to your firm’s first.

Jackie DiMonte 43:14
Okay, of all the ones that I have worked on, and worked on meaning getting too deep diligence. So it might not be something that we invested in, but we spent meaningful time on, I would say maybe 10%. And then there’s this big giant group in the middle that are network intros, whatever. And then I’d say maybe 20% 30% are outbound. Now I, I really like to talk to companies that I’m interested in from the onset, which seems like a little bit of a silly statement to make, but when you get inbound or network intros, sometimes they’re just topics that are not as interesting and you’re the wrong person, for that company to approach or for that insurer to be made to, for example, healthcare IT is something that I have no gut reaction to, I think either everything is cool in that space, because it’s all helping people and hospitals, or nothing is interesting, because I have no idea if it’s better or worse than the last thing that came around. But when you’re talking to other investors, you know, they know that you’re a seed stage investor, you’re agnostic to you know, business model or industry. They have a really interesting you know, healthcare IT not to bash on healthcare IT. I think it’s amazing, it just, you know, my expertise is not there, and they send it to you. And now you’re like, ah, I have this meeting. I don’t really know what to do with it. Okay, I should loop someone else and, and it it creates some weird dynamics because you’re the one who sourced it, but the other person would be the champion. And so sometimes there’s friction because This is like a little secret that is silly, but like people like to feel ownership over the companies that they’re bringing forward, like, you want to feel that personal connection. And one way to do that is to be the person who found it, right, the one who brought it forward. They’re totally exceptions. And in every fund I’ve worked with deal teams come together and someone will build more excitement. But like, you got to have that first question person, push it, push it through. And the reason I talked about this is because when I find a company on a list, or through, you know, a networking event, or, you know, a referral from another entrepreneur who said, Oh, these, you know, these 10 companies are really interesting. And I pick like one or two of them, those companies I can get really emotionally excited about, because I already know, I like the idea. If the entrepreneur and I connect, it’s, you know, it’s positive. Usually, if there’s, you know, good good metrics out, like, you start to kind of build your case and like, create emotion. And so I personally have done a lot more investing in companies that I have proactively reached out to then companies that I have found from inbound or network, I assume, that will change Evan flow over time, of course, because, you know, half the companies that I invested in, I did as a senior associate where I had, you know, a less experienced and less robust network. So I assume that, you know, evolves. But I really do like that proactive, you know, outreach and, you know, being prepared for the call before you jump on the call, so you can really get into the fun stuff. So anyway, long, long story short, the inbounds, you know, we spend time on them. But I would say there are a lower volume of the meetings that end up being interesting. Of course, you know, we don’t have like, maybe I don’t have the great, greatest brand for inbound. So, you know, here I am. Hi, guys. You know, come send me, you know, send me things meet with meet with me, this could just be a bad signal of how you know, my magnetism as a as a VC. But long story short.

Eric Hornung 47:11
How much of that signal that you’re putting out there is explicit versus kind of the standard buzzwords in the venture space? Like, are you saying, Hey, I’m really excited about this very specific problem, if you’re, here’s a request for startups are like, and where are you doing that? If so, like, How do I know what you’re interested in? As an entrepreneur?

Jackie DiMonte 47:31
It’s a great challenge for folks like me that work in funds like mine. And what I mean by that is, an interesting idea can come from anywhere, especially because we invest in almost everything in anything, right? We have services, businesses, we have marketplaces, we have consumer, we have enterprise SaaS, like, we do everything at CV and so it’s hard because you don’t want anyone to say, Oh, this isn’t really something you do, like I had, I was joking about an investor who is very technical. And I really enjoy hanging out with him. I was I was joking with someone yesterday that he’ll say, Oh, this is this is really interesting company. It’s it’s kind of technical, though. I don’t know if you do that. You know, I don’t know if you do that kind of stuff. And it really you want to say if it’s an interesting company, I want to take a look right? Because we will do any of that stuff. Now there are things that I’m not, you know, adequately prepared to analyze. But like, yeah, I want to look at it. So the hard part is, the more you specify, the less people are going to show you outside of your area. On the other hand, the more you can specify the more people know what to send you. So it’s a little bit of a it’s a little bit of a poll, or a push poll, a teeter totter, whatever. I’m using my hands now to show what you know, where the tension comes from.

Eric Hornung 48:52
The DiMonte paradox.

Jackie DiMonte 48:53
Yeah, exactly. So so yes, and no, I like to develop themes where I can fit different industry verticals, or different applications in those themes. My last one was on fragmentation. I really like fragmenting markets. I like infrastructure for fragmenting markets. So companies that enable other companies to do things. I have a blackboard up behind me this is this is part of one of those applications, I like to do a lot of a lot of diagramming. I have always been excited about network based companies, whether that’s marketplaces, I mean, now a lot of people are calling them community startups in the consumer space. So I try to put out themes. When I meet with other investors. I say I like network things. And that can be consumer enterprise that I like when you have matches and transactions and things like that. So I tried to build some of those elements into everything I write about or speak about, that don’t really shut me off from topics that I might be interested in. It is it’s a very big tension that I’ve played with I love supply chain. I love logistics. Does that mean I can’t do an investment in podcasting? You know what I mean? Like there that that creates tension for me. And part of the reason why I met a generalist firm is that I can look at all these different different things.

Eric Hornung 50:17
I love that we named the tension, and I’m going to use that on a go forward basis.

Jackie DiMonte 50:21
Yes, please. Yeah, I’m getting my trademark as soon as we get off the call.

Jay Clouse 50:26
The DiMonte paradox will be henceforth used on the Upside podcast. Well, I’ve last question, Jackie, to kind of tie things together. You know, you mentioned at the beginning of this, you really like to be able to see things as measurable and having a result. And that’s kind of what drove you towards finance in the first place. You just took this job a few weeks ago, and you’re learning all this a new but it sounds like you’ve been given a lot of autonomy to kind of represent the firm and do your own thing down there in Austin. So what are you holding as your own personal goals and benchmarks for the foreseeable future in that new role?

Jackie DiMonte 50:58
Yeah, I spent my entire break thinking about what are the different systems I’m putting in place to make sure I’m as successful as I can be in this role. I do buy into this idea from a personal performance standpoint, not necessarily from a company or startup perspective, but you know, routines, framework systems, not necessarily concrete metrics or goals. So for me, it’s much more of a volume thing versus say, have I accomplished this many, many meetings. You know, in my first 60 day plan, it’s all about going on a road show, I want to meet someone from every fund in Texas and the southeast, if I’ve known someone before I want to reconnect, tell them what I’m working on, hopefully, you know, they will reciprocate and send me send me things that fit our thesis. And certainly for the for the folks that are new, I want to build a relationship into each and every one of those funds. So that’s one of the things I want to meet every seed stage founder in Texas that we have not already invested in. Part of my excitement about being here is there’s just not a lot of people that look and act like me in the city. And I think you can say that about venture capital and all, you know, women are still a fairly small proportion of of, you know, what they call decision makers it finds. And that is certainly true in my current city, and certainly across the southeast. And so I really want to lean hard into brand development, I have some metrics around both written and social. And then you know, making sure this is a little bit of a softer element, but making sure I am developing those touch points within my organization, because you know, it is a very people driven business. And it can be hard to do things without having the support and trust and relationships internally. And so I have I have those there. I mean, I’ll show you I know we’re in a podcast, I’ll just like describe it, but like I do daily check, you know, check marks.

Jay Clouse 53:09

Jackie DiMonte 53:10
And have codified a lot of the things that I want to incorporate into, you know, sort of the longer term as I operate. So yeah, great question. I spent so much time thinking about it. I’m glad I got a chance to put it put it out there.

Eric Hornung 53:25
I will not show you my notebook because yours looks like it was done by an artist and mine looks like I don’t even know what yeah, I see at least Jay you have pictures.

Jackie DiMonte 53:33
Oh, I like the pictures there’s pyramids.

Jay Clouse 53:35
There’s a pyramid there’s.

Eric Hornung 53:37
Mine is like a Rorschach test.

Jay Clouse 53:39
Boxes and triangles.

Jackie DiMonte 53:40
Well, Jackie, this has been awesome. If people want to learn more about you or Chicago Ventures, where should they go?

I am on twitter @JayDiMonte. JayDiMonte. You can send me an email. It’s Jackie@ChicagoVentures.com or you know, if you find me in the ether. I’ll respond.

Eric Hornung 54:00
Jay, we need more stories.

Jay Clouse 54:03
We need them. The world needs these stories.

Eric Hornung 54:06
And the best way to tell stories of local business ecosystems is to join up with the Upside Podcast Network. Jay, what’s that?

Jay Clouse 54:14
The network is growing. We have three shows on the network. Now with Upside, When Pigs Fly and Lay of the Land. We are knee deep in Cleveland and Cincinnati now but we want to explore other cities more deeply as well.

Eric Hornung 54:27
Anywhere in the United States. If you are listening to this or you know someone who wants to launch a podcast exploring the local business economy, the local business ecosystem in that city, reach out to us at network@upside.fm. Let us know what city and what you’re thinking.

Jay Clouse 54:44
We’re a fun group of people to work with. We’ll help you structure a show that is ready for the airwaves. And honestly we give you a ton of creative control. All we ask is that you tell really exciting stories in your local ecosystem.

Eric Hornung 54:58
And we will help you do just that. Nothing but Upside in this arrangement.

Jay Clouse 55:02
So send us an email network@upside.fm. And we’ll be talking to you soon.

Eric Hornung 55:14
All right, Jay, we just spoke with Jackie DiMonte. Now of Chicago Ventures, where you want to start with this one.

Jay Clouse 55:21
I had a lot of fun talking about what it means to be in different roles at a venture firm. I think I misunderstood kind of fundamentally what these different positions meant. And it makes sense in the frame of the higher you climb, the more the firm trusts you to represent the firm externally. And also, the more implicit and explicit authority you have for moving a deal through the process that makes some sense. And I don’t know why I didn’t quite think of it that way. I think I was likening it to, like management consulting, where as you grew up the ranks, it’s more about just like selling business in in leading and managing teams. And that’s not really the case in venture.

Eric Hornung 56:01
It’s much more like, this probably isn’t as close. But it’s much more like Congress where the longer you’re there, the more clout you have, in some ways, because it’s not just about title, I think Jackie was talking about how when she was a senior associate she was pushing deals through. And she didn’t say this explicitly, but implicitly, you can think about someone joining as a senior associate new who hasn’t gone through the intern analyst senior associate phase, maybe not having as much clout as Jackie, even if they did have a higher title.

Jay Clouse 56:28
This seems like a really cool opportunity for her to be the one Chicago Ventures, not only partner, but person in Austin. And I’ll be interested to circle back with her here in the next few months to ask, you know, how is this played out? from a pure branding perspective, it seems like it could be a little bit confusing and difficult, but it’s certainly overclockable. It just seems like a really cool opportunity to be, quote, unquote, you know, new firm in town. And I wonder, you know, what the Austin ecosystem is like how friendly and welcoming they are to new firms on the coast. You know, there’s a lot of competition for deals. And then in a lot of the cities, we cover here on the show, they’re all saying we need more and more and more firms. Austin has always kind of been somewhere in the middle in terms of their evolution as an ecosystem. So I wonder where they are in the evolution of firm friendliness versus competition.

Eric Hornung 57:21
I feel like we’re gonna learn a lot in this next year, as we move back, maybe not 100%. But we move back and away from just the zoom meeting, lifestyle we’ve had for the next the last 12 months and into the more community events, meeting style of the future. I think it’ll be a hybrid, obviously, I don’t think zoom meetings and connecting with people outside of your geography is going away. But I think that people are yearning for some of that community. Community. I don’t know, I don’t I didn’t have a good word for after community.

Jay Clouse 57:53
Yes, you mentioned the walk and talk meeting and how you didn’t need an agenda for the walk and talk. And for a minute, I was like, Oh, I forgot that was a style of meeting,

Eric Hornung 58:02
I forgot that going to coffee shops a couple times a week. and meeting people in the morning was a huge part of my life for like years and just hasn’t been for a year. So it’s going to be interesting to see how we re integrate into that style of life and meeting. We’ve also had so many moving pieces in these different communities in this last 12 months that weren’t there. Normally, they get introduced gradually to each community. Over time you have someone joined, they get introduced, you have someone else joined a month later, they get introduced. But in the last 12 months, we’ve had hundreds of people move across different geographies popped down, especially in Austin. And then when everything kind of starts opening back up. And I know Texas is a little ahead of us here in Ohio in terms of opening back up. But once everybody’s comfortable in these meetings, and walk and talks and community gatherings are back, you have just a influx of new people who weren’t there last time we were doing in person meetings.

Jay Clouse 58:54
Oh, that’s really interesting. I thought about that. Oh, we’ve said the word interesting too many times, Nathan’s gonna yell at us. Another thing that I really liked about this conversation, or that got me thinking because I’ve implicitly been thinking about it. First of all, the breakdown of how much of true deal flow comes from the inbound pitches you get juxtaposed against more and more, it seems like firms realize they need to have an externally facing brand. And the result of that is they’re going to get more and more inbound, which on average, isn’t going to be where you’re investing your time or money as a firm. So it’s an interesting balance. Now, there it is, again, it’s it’s a challenging balance, I’m sure to both simultaneously want to drive more inbound, knowing that most of that is not actually what you’re looking for, for the purpose of building the brand and building credibility.

Eric Hornung 59:44
And as we dive into the newly named DiMonte paradox, I think it’s even more of a word you use challenging balance was that the word the phrasing you just use?

Jay Clouse 59:56
I think so.

Eric Hornung 59:57
Because there is on one end Hey, I’ve done a lot of research, I love this market. I love this about the market. And I’m looking for very specific kind of thesis driven, or at least market driven companies in that space. So when she said, a certain percentage of her deals, I think it was 30% are probably through direct like outreach. And on the other side, you don’t really know what you want to see. Because you don’t know what’s out there without that random kind of walk of what comes in an inbound basis. So you want that net on the left side to be or the inbound side to be as large as possible, and as diversified as possible. And as potentially shocking to you as possible. While on the right side. I’m using left’s and rights here because you know, the listener should be able to see me, but mentally, the outbound side, you have very specific things that you’re interested in. So there’s a higher conversion rate on the one side versus a very low conversion rate and the other side, and how does that look? And how does that feel to the market? I think there’s a lot of times why founders say, I feel like I have to have 100 venture capital meetings because no one wants to say no to anything that they might be interested in. But at the same time, the likelihood is they’re going to say no to just about everything unless they are interested in it.

Jay Clouse 1:01:13
Well, dear listener, we’d love to hear what you think about this episode, what you think about the DiMonte paradox. You can tweet at us @upsideFM, or email us Hello@upside.FM, and we’ll talk to you next week. That’s all for this week. Thanks for listening. We’d love to hear what you think about this episode. So tweet at us @upsideFM or email us Hello@upside.FM and let us know. You can learn more about us and browse our entire back catalogue of episodes@upside.fm. And if you love our show, please leave a review on Apple podcast that goes a long way in helping us bring high quality guests to the show.

Interview begins: 7:15
Debrief: 55:14

Jackie DiMonte is a partner at Chicago Ventures.

Prior to joining Chicago Ventures, Jackie was a principal at Hyde Park Venture Partners, working with portfolio companies such as RoadSync, Podchaser, Fixer, FactoryFix, and PartySlate. Before that, she worked at Silver Spring Networks (now Itron), an IoT company for critical infrastructure, driving development and pilot projects for emerging smart city technology.

She is also a member of the Board of Directors for Starting Block Madison and Chicago: Blend and a Venture Partner at Republic.

We discuss:

  • Feedback Loop 13:54
  • Evolution in a Venture Firm 17:14
  • What Level is a Deal Flow Done? 21:46
  • Get a Deal Through 24:17
  • Programmatic Venture 26:35
  • Working Virtually from Austin 31:13
  • Partner at Chicago Ventures 35:27
  • Inbound Pitches 42:43
  • Fragmenting Markets 48:53
  • Personal Goals for the role 50:26

Chicago Ventures was founded in 2012.

Learn more about Chicago Ventures
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