Chicago Capital

Ira Weiss is the General Partner & Co-Founder of Hyde Park Venture Partners. He is also a professor at the University of Chicago Booth School of Business

Show Notes

Ira Weiss is the General Partner at Hyde Park Venture Partners, an early-stage venture capital firm focused on high-growth, mid-continent technology startups. Ira is also a Clinical Professor of Entrepreneurship and Accounting at The University of Chicago, Booth School of Business.

In this episode, we covered:
  • From Shoe Salesman to VC
  • Developing a Market View Advantage
  • Metrics in Valuations
  • Keys to Success for Unicorns
  • Improving Chicago’s Ecosystem

And much more.... Please Enjoy!

You can find Ira on his Linkedin & Twitter and Hyde Park Ventures on their website, Twitter, and Linkedin.

Ira’s Favorite Thought Leadership/Resources: The 20 Minute VC, a16z Podcast, Fred Wilson, Brad Feld, Mark Suster, & Ajay Agarwal’s Writing

Manifold Group is a venture holding company based in Chicago with offices in Dallas, Los Angeles, and soon Atlantic Canada. Early stage private investments represent an extraordinary investment opportunity, but existing investment models in the space leave much to be desired.Manifold is a new model for growth in the new economy, designed to create and capture value at the early stage through synergies across its venture fund, incubation and acceleration studio, and advisory firm. Learn more about Manifold at https://www.manifold.group.


What is Chicago Capital?

The Chicago Capital Podcast explores the startup and Venture Capital ecosystem in the Windy City. Each episode will feature a prominent founder, Venture Capitalist, or Angel investor who plays an integral part in the city's entrepreneurial story. Join host Matt Castellini as he chats with guests about their career journey, their perspective on a particular market, and their thoughts on the Chicago VC and startup scene.

[00:00:00] Ira Weiss: [00:00:00] Professor
[00:00:16] Matt Castellini: [00:00:16] Weiss. Thank you so much for joining us on Chicago Capitol. It's a true honor to have you here.
[00:00:22] Ira Weiss: [00:00:22] Thank you for having me, Matt. I've been listening to your podcast for awhile now and excited to be here.
[00:00:27] Matt Castellini: [00:00:27] Thanks so much. That means a ton that you are our first academic, uh, on the podcast. So I guess it's fair to say, class is officially in session now.
[00:00:35] I've been waiting to make that joke for about a month and some people appreciate it. That's
[00:00:40] Ira Weiss: [00:00:40] great. I don't know if that's a plus for the VC community, but I'll, uh, I'll, I'll take it anyway.
[00:00:47] Matt Castellini: [00:00:47] So mentioned that you're an academic. I think we'd love to hear about your background a little bit. It's fascinating.
[00:00:53] And you truly have sort of a unique perspective on VC, uh, given how much time I think you've spent in the academic world. [00:01:00] And I know there's at some point a shoe salesman role that played a, you know, a great effect in your, your development. So we need to hear, I think the whole tapestry of the history of professors.
[00:01:13] Ira Weiss: [00:01:13] Okay, well, I'll, uh, I might maybe I'll start with that, which is like, I'm kind of from a, I'm literally from a family of shoe salesman and shoe sales. People were like my great grandfather back in a country called Galicia in Europe. Owner's shoe store. Uh, my grandfather, you know, moved, they moved to Chicago and he opened it.
[00:01:35] He ended up with two shoe stores. My father owned a small chain of shoe stores in Chicago called Tico feminine footwear. Uh, I have two brothers, my brothers and I all worked at a chain of shoe stores in Chicago called churn and choose to make money on the side while we were in high school. So like, it just goes back forever.
[00:01:54] And I think that the way it relates to the work that I do in the venture world is like, my father was, you know, like [00:02:00] my father was an entrepreneur and we use a real entrepreneur. He started. A chain of shoe stores from nothing, you know, built it from one shoe store up to seven shoe stores. And he used to kind of hurt a lot by the recessions at the time, which was retail.
[00:02:14] And so he ended up back down at one shoe store after he had up seven. And so, you know, part of what I feel like when I'm helping a bit, you know, VCs don't really do the work, but like helping a bit with entrepreneurs is like, I'm kind of. Helping the men and fathers passed away, but like helping the memory of my father to be a, to be, to be as successful as possible.
[00:02:33] So, so that's kind of the history, at least on the shoe sales person side, um, you know, went to college, um, worked as an accountant briefly, um, for a variety of reasons, decided to get a PhD in accounting. Um, I'm pretty sure I'm the only accounting. Academic, who is a professor who's, you know, now does venture capital and investing work.
[00:02:54] Uh, but I, uh, got my PhD at Chicago. Matt's great. The year at MBA, you know, an MBA student at [00:03:00] our school. And then I went to work at Columbia business school in New York in 1999. When the tech bubble was in its bloom and there were, and you know, frankly, a lot of my MBA students were going off like literally ditching their second year of business school to go off and work at tech companies.
[00:03:16] And so there was a professor there named Matt Rhodes Croft, um, who was a finance professor. And I was an accounting professor and the two of us started doing it. Um, startup investing on the side of our day jobs. And we like to joke that we would, you know, we'd like work and then we'd like take all of our, you know, whatever hard earned money that we had.
[00:03:35] And we had a very expensive hobby called startup investing. And we did on that. We did that on the side for a while. And then, you know, eventually we formed a group that was that's akin to a pledge fund and we got some, you know, friends and family involved in doing some of the startup investing with us.
[00:03:52] And that that's kinda my. The beginning of my venture career. And what I realized was I did, I did really like the academic world and really like teaching [00:04:00] part of it mostly, um, loved working with, uh, students, MBA students and others. But I really just fell in love with working with entrepreneurs, um, the excitement and the energy of people who have new ideas.
[00:04:12] Um, people pitching to me all day on, you know, what is the world going to look like in three to five years? Um, learning about new industries. And so, you know, It's been very, very fortunate that I've been able to do both over time. Um, spend some of my time teaching MBA students like UMAT and some of my time, uh, working with entrepreneurs and investing in startups.
[00:04:33] So, so, and so I, you know, that's right. So I moved, I was in New York for a bunch of years. I moved back to Chicago to teach at university Chicago. There was an entire group of Hyde park angels that had started. Right after, um, grub hub and Braintree went through the new venture challenge business competition that you were in Chicago.
[00:04:50] And so for a variety of reasons, there was some alumni that got together to form an angel group. The school was open to that an angel group that was filled with the school. And so I was asked to step [00:05:00] in to help run the group and really be like a liaison to the group in the early days. Um, helped with the group for the first few years, and then branched off and started doing investing on my own and formed, um, high park venture partners with, with guy Turner who I know you've already had in the past.
[00:05:17] Thanks. Thanks shoes to fill. Since I know you've already had guy.
[00:05:21] Matt Castellini: [00:05:21] Yeah. You know, it's the follow-up act. It's the Encore everyone was clamoring for after we had guy on people were just saying, you got to get professor Weiss and I can attest to all listeners, the VC lab course, which professor Weitz teaches is worth the price of admission to booth on its own.
[00:05:35] So I can't recommend it enough. I can't recommend booth enough. If you're interested in this space had to give booth the quick plug there. I'm
[00:05:42] Ira Weiss: [00:05:42] flattered. I think it's probably cause you like listening to Jason Helser who I know, but I'll, uh, consider myself the, the, uh, the player the also ran. So
[00:05:52] Matt Castellini: [00:05:52] no, it's a it's it truly is an excellent course.
[00:05:55] And it is, I don't know how many other business schools out there you can get to practicing, [00:06:00] you know, managing partners at two of the most preeminent funds. Uh, Given geography to sort of come in every single week and teach you all the tricks of the trade. You know, one thing I'm curious about just based on your background, based on how much of a focus you've had on accounting for your entire career.
[00:06:15] Did you, when you started making angel investments, did you ever think maybe you wanted to move later stage where there was a little bit more data to support these investments that you were making? There was a little bit more accounting being done because you are very focused at the early stage. And it's just a funny, sort of, to me, it's a funny pairing and I can, you know, an accounting PhD and early stage startups.
[00:06:36] How did you, how did that sort of, you know, how did that develop over time?
[00:06:40] Ira Weiss: [00:06:40] Yeah. You know, I think it's a, it's a very insightful question about me, Matt, because it, it, you know, and even when I started doing startup investing, there was a little bit of a disconnect. You know, accounting, professor academic, you know, there's a lot of rigor.
[00:06:54] That's typically involved in a lot of the stuff that I do. And then you have early stage investing where like, you know, in many [00:07:00] cases we're investing at, you know, pre-launch stages. And so, um, you know, I think. Um, I, you know, I don't know. I just, I really love early stage investing. Um, I think now I've been fortunate because some of the companies I'm involved in have gotten to be much later stage.
[00:07:18] And so I have, I'm experiencing more of the later stages and that's a pretty interesting stage as well. Uh, but there's nothing, I think there's nothing really. Being involved really towards the beginning or at the beginning, we don't, you know, VCs don't do the work. We don't do any real work, but like, even like an intro here, or like introducing someone to, you know, someone who becomes an early key employee and the impact that can have on people's lives, you know, it just feels like when the companies are much larger, um, it's just harder to have as big of an impact.
[00:07:50] And so I think I've, I've definitely enjoyed, um, the impact and really getting involved pretty pretty. Yeah.
[00:07:57] Matt Castellini: [00:07:57] And we'll talk about, you mentioned some of your [00:08:00] companies moving on to later stages. Oh boy. Is that true? We've got a few companies that hopefully we'll get to that have reached unicorn status from, from high parks portfolio very recently, but a few more questions on, you know, your, your background, I guess, is.
[00:08:15] Have you found over time? What has it been like balancing, you know, being both a professor and a venture capital investor, have the roles over time, sort of informed the other, have you taken some of your, your time you spend in the classroom around young sort of students who are looking to found companies and will you ever make investments, you know, from those relationships or how have the two sort of merged over time?
[00:08:37] Ira Weiss: [00:08:37] Yeah. I mean, it's a, it's a great question. I think the way that there's been overlap, to be honest with you is mostly through. The my, you know, the investing that I've done with startups and actually bringing that into the classroom a bit. And so, you know, I teach I've been co-teaching the venture capital lab class.
[00:08:55] Uh, but I also teach a class called accounting for entrepreneurs. Um, we, we, you [00:09:00] know, the sexy part of the topic is accounting for entrepreneurs from startup to IPO. Um, and I think, um, you know, by making these startup investments and being involved in a lot of these companies, I think it does give me.
[00:09:14] You're not just anecdotes, but a lot of context for the kinds of things that it's helpful for students to know as they're going off to start companies or they're going off to be part of entrepreneurial teams. And so I think it's mostly been that way. I mean, I think here and there every once in a while, well, there's certainly great, um, teams that are coming out of the universe, Chicago.
[00:09:35] Um, to be honest with you, just to, uh, try to help avoid conflicts. I have, you know, other folks that are, you know, our firm, um, work with the, you know, if they're still students kind of work with directly with those students. But, um, but, but I think I also, you know, in some ways, like now have had the context over time of watching these companies grow and thinking about the kinds of things that a CFO really CFO would think about at [00:10:00] various points in time or a founding team, you know, fall on financing.
[00:10:04] Um, you know, thinking about things like, um, governance, you know, how do you know founders, like, you know, you want him really it's like the classic, like, well, I want to become rich and I want to maintain control. And so I think I have much more context for how to do that over time and what to think about.
[00:10:22] And. And then, you know, I think I also am able to bring some real-world examples of things that I've seen, um, around the frameworks that we use when we teach the classes at booth. So, um, you know, I think certainly some of my academic knowledge and, you know, I meet great students, you know, here and there what's really happened for me at booth is, you know, because I've been involved in some of these pretty, you know, few interesting companies that have gotten to be much larger, um, here and there, when students have been graduating.
[00:10:52] I've been able to introduce them to some companies that I'm involved in. Um, you know, I, I, I probably have. [00:11:00] Three or four of those a year at this point where like some students are graduating or they've graduated and then I'm like, oh, like your background would be really good for this specific company.
[00:11:08] So we have one company I'm involved in. Um, that's a re recently came out of stealth mode called Fairfax, and it's a new futures exchange. The, um, chief of staff was a student that I met a booth chief of staff for the CEO and the VP financial. Tony grief, Tom Rafferty is the chief of staff. And Tony grief is a, is now the CFO who recently graduated booth or introduced him as kind of, as he was graduating.
[00:11:34] So I've done a bunch of those things at ShipBob and elsewhere. And so, um, I think that's the way that there's been a little, a little bit of it.
[00:11:41] Matt Castellini: [00:11:41] I feel like we are convincing so many people to go to booth and take your class right now, just for all the, uh, potential, uh, down the road incentives. There might be hopefully to land landed a job at one of the fastest growing startups and a Hyde barks portfolio.
[00:11:55] I I'm curious about, do you see other academics, you [00:12:00] know, moving into VC? Is this something that you've seen at least from the business school level? Do you hear this happening?
[00:12:07] Ira Weiss: [00:12:07] I don't know, you know, I mean, I think for me, it was a little bit more happenstance, to be honest with you, Matt might like my grand world plan, which I didn't mention earlier was to go work at the international monetary fund or the world bank.
[00:12:20] Like that was kind of my grand plan out of undergrad. Part of the reason I went to get a PhD. And so, um, you know, I think most academics. Are driven by like curiosity, knowing more about the world. Um, I think, I think VC is, is just, there's different things that drive people are VCs, but here and there, occasionally you see people in the academic world going off to start companies, particularly if they're in computer science or elsewhere.
[00:12:45] So, you know, here, there you'll see people getting PhDs and especially, you know, in the bay area elsewhere, like come out of scorn biotech and they start a company. Um, I don't know that. Um, I'm creating a path for folks [00:13:00] who, you know, go to get a PhD, so you can become a VC. You know, that's not, not what I, not generally what I tell my students.
[00:13:06] So
[00:13:08] Matt Castellini: [00:13:08] the professor Weiss movement, I could see it. I don't know. I could see a, uh, you know, a bunch of PhDs following your footsteps. I'd love to focus on Hyde parks, origin. You know, we, we had guy Turner on the show and he gave us a good lay of the land. I think of the investment mandate behind high park and what you all look for in your investments.
[00:13:25] But I'd love to hear from your perspective, you know, how the funds sort of originated and how it's grown over the past, you know, almost 10 years,
[00:13:33] Ira Weiss: [00:13:33] you know, how did the F how did we start while I was doing all this startup investing in New York with a pledge fund, um, was called RK ventures. It was just a partner and I.
[00:13:42] And then when I moved, I'm originally from the Chicago area and moved back here. Um, and it was great. It was pretty, I would say a little bit early in the tech scene in Chicago, like when I showed up, um, you know, Braintree Braintree was around. Um, and you know, it came through the new venture challenge about like, I think the year [00:14:00] that I showed up and then like the year after I showed up is when grub hub went through the new venture challenge, the, to Chicago.
[00:14:06] I love doing the startup investing and you don't really want to do it on your own for a variety of reasons. It's better to do it in a, in a partnership structure to have at least one other person. And so when I met guy, you know, I like to say he was like my star student term teacher, because I was like, this he's just, he was, he was amazing.
[00:14:24] And I just loved working with him and I was like, yeah, I know he went off to work at BCG for a year, but I'm like, Hey, we got to raise a fund because like, you gotta come work with me. Um, and he's like, well, that's great. But like, how are you going to pay me? And also say that there's certainly an opportunity because there isn't, you know, there wasn't as much instilled as not as much early stage capital.
[00:14:43] Um, in the Chicago area and in the Midwest, as there is in the coast or in New York. So, you know, we certainly saw the opportunity, but, you know, I think some of, some of it was happenstance. And I think for us at high, on the high powered venture partner side, at least, um, you know, I think [00:15:00] that remains true to today.
[00:15:01] You know, there's still, there are some capital at the earliest stages, you know, the pre-seed seed in Chicago throughout the Midwest, but, you know, they're the return. On average have been very, very high. And I think the reason the, you know, the financial trends have been highest because there's not, as, you know, there's not as much capital as you probably want.
[00:15:20] And so I think that, um, I think the opportunity remains. So, and we, you know, as guy has said on your prior podcast, we do early stage tech investing primarily in the Midwest and by the Midwest, we include, you know, what you traditionally think of as the Midwest plus Toronto. Um, I like to joke which now will be forever.
[00:15:40] Remember that, like, you know, we include Toronto as part of the Midwest, but don't tell the Canadians that cause that will be exciting to them. Um, I don't think I've ever said that when I was being recorded before. Uh, but I think they, hopefully they appreciate it. And I think, um, we've, you know, we've really enjoyed, um, our, the investments that we've made in the Toronto it's really, [00:16:00] really great market.
[00:16:00] Um, in some ways similar to. Oh Chicago. So, yeah,
[00:16:05] Matt Castellini: [00:16:05] I mean, aside from Toronto, um, have, were there times over the past 10 years where you two felt pressure to move outside of the big continent and maybe take on more geographies or have you just been even further emboldened by all of, sort of the success you've had in the Midwest and, and you really decided to double down, I'm just curious if there was ever any ever times where you thought about moving to different parts of the country for your investors.
[00:16:32] Ira Weiss: [00:16:32] Um, I mean, I think, you know, you, you know, every firm and VC has to play to their advantages. And I think, um, you know, being close to companies and geographically close is the, you know, is an advantage. And so, like, it's really hard to say, you know, take some of the coast, like I'm not going to find them.
[00:16:51] Even if I, you know, even if I have to think I'm, I'm a halfway decent investor, um, really, really hard for me to get into the really best opportunities in the bay [00:17:00] area or New York or Boston or even Austin. Um, you know, I think you need to really develop, um, you need to develop, you know, if you're physically in a market, you have an advantage or occasionally if you've made some investments in, uh, in a regional ready, you may have an advantage.
[00:17:17] And so I think. There definitely has been internal discussion at our firm about, you know, expanding beyond the geographies to we had someone, well, someone on our team moved to Austin, Texas for awhile. And so we had a brief discussion about that, but, you know, if anything, like, I think we've generally been reigned in of like, you know, we want to be investing where we have an advantage now in a COVID world, you know, where everything, a lot of things are virtual.
[00:17:43] Um, some of that advantage has gone away. To be honest with you. You know, you have coastal VCs, people in the bay area was just sitting in the background doing zoom all day. And so we definitely see more coastal funds investing earlier than they did before. Uh, but I think we, you know, [00:18:00] still being close to entrepreneurs gives us, um, a little bit more of an advantage.
[00:18:04] So, you know, the other thing that gives us, I think I might've talked about this is, you know, there are some. There are some themes that we tend to invest under and think areas where the Midwest has an advantage or at least not a disadvantage. And so we've made a lot of logistics related investments as an example, um, you know, for kite ShipBob, you know, two companies that have done really well, a company called road sync.
[00:18:27] We've made some manufacturing tech investments, a company called fast radius that just announced a spec that's, you know, a $1.4 billion stack. Uh, we've made some farm tech investments like farm logs, like things where, you know, the Midwest tends they have an advantage or at least that a discipline.
[00:18:43] Matt Castellini: [00:18:43] Yeah, that's actually a question that I was curious about in the first place is, you know, Chicago specifically, but I guess the broad Midwest, um, you hit a few of them, but would you say that, you know, manufacturing logistics are, you know, at this point clear, cut.
[00:18:57] That's a industry that the Midwest, [00:19:00] or at least Chicago is a leader in, um, and it's an area where you think dollars are really gonna flow and concentrate in this geography.
[00:19:09] Ira Weiss: [00:19:09] Yeah, I think it's fair to say that about logistics. Um, I mean, we're not the only part of the country that is great at logistics and has a, you know, kind of deep Cedar roots, like, you know, Atlanta would as well, maybe Indianapolis, which is an RGO.
[00:19:23] Um, and there certainly are some great, you know, logistics related companies that have sprung up. In, you know, in the bay area and elsewhere, you know, the convoys of the world, the Flexport's of the world. Uh, but I think there are some pretty exciting local companies and logistics and a lot of logistics related DNA.
[00:19:42] So that even if you see like European or Israeli companies that are logistics related, when they open a us office, Pretty frequently. They're like, we'll, we'll open it in Chicago. So a couple of cup bring has done that. There's some other, there's just a lot of, a lot of local talent that knows it. Well, I think for a variety of reasons, [00:20:00] one is like we're in the center of the country.
[00:20:01] And so we've always been a little bit, a little bit of a logistics hub. But there's also a little bit of a quirk of history where, um, the trucking brokerage business was really strong, started in Chicago by a guy named Paul Loeb who started a company called American Backhaulers. And so there's a lot of DNA that, that came out of, um, the starting of that company, which was, you know, 30, 40 years ago around the, when trucking was deregulated.
[00:20:26] Um, and then, you know, and then of course, you know, big airlines that are here in Chicago, like, like United.
[00:20:32] Matt Castellini: [00:20:32] Switching gears a little bit. Uh, wow. I just had a trucking pun right there and I'd even set that up. That's uh, that just flew right off the tongue. That's great. Oh,
[00:20:42] Ira Weiss: [00:20:42] I love that. I love that you're not digging a hole for yourself here.
[00:20:45] So
[00:20:46] Matt Castellini: [00:20:46] switching gears, um, a topic we talked a ton about in our class obviously is the due diligence process as a VC investor. I'm curious, given your extensive background in [00:21:00] accounting, Are has startup accounting changed in any way in recent years or as has more capital has sort of floated into the system?
[00:21:09] You know, one in particular topic me and guy talked about was a car, uh, you know, that type of a metric being used more and more. Are there, are there other types of changes you've seen in recent years at the earliest of stages?
[00:21:23] Ira Weiss: [00:21:23] Um, I mean, it's a very good question. Um, you know, there are, I think, you know, when you talk about some of these metrics, it's really about KPIs, key performance indicators and, and in some ways less so about, you know, the accounting function and direct accounting information.
[00:21:42] And so there's certainly been evolvement some evolution of the way that startups end up using key performance indicators. Guy. Might've talked about how. You know, I think we, we all talk about annualized recurring revenue, right. And there's different [00:22:00] mean to that. And that, you know, that's evolved a bit where companies use like committed annualized, recurring revenue, um, or booked, you know, there's some companies that talk about booked recurring revenue, uh, but booked may not be implemented recurring revenue.
[00:22:15] And so a lot of, some of these measures could be squishy. I mean, I think these are. They're all important metrics. And I think, you know, the other things that have been around for a while, things like cost customer acquisition, lifetime customer, um, and there have been, I would say a bunch of advancements, not pure county related, but more like, you know, how to look at those metrics, how to think about them over time, you know, even measures of, you know, by reality, those kinds of things.
[00:22:39] So I don't, um, you know, it's not as much accounting related as it's like, I would say metrics really. For you,
[00:22:46] Matt Castellini: [00:22:46] was it challenging though, in the beginning, you know, when you first started making investments in early stage companies and maybe even, you know, once you joined hierarch angels, once you, you know, um, started at Hyde park venture partners, what was the learning curve for you?
[00:22:59] Like [00:23:00] personally, when you know, you have this background again, probably of looking at three statement, financial statements, um, having sort of fully fleshed out financials to go off of what was that like for you? You know, back into the very early stages when there's so much less data and what's a little bit more ambiguous.
[00:23:16] Well, actually a lot more ambiguous. How did that develop for you?
[00:23:20] Ira Weiss: [00:23:20] Yeah, I mean, I think the craziest thing for me to be honest with you is like the waves that valuations in the early stage world is just so devoid of. Real financial metrics. So like, you know, some of the companies we invest in are, you know, they're prelaunch, like how do you value a company that's pre launch?
[00:23:40] Um, you know, people would just come up with these values. $3 million, $5 million, $10 million. You know, this company has, it's not launched. There's nothing. Like if you came to me with an idea matter, let's say I came to you with an idea. And I was like, Hey Matt, I've got this great idea. Like, I want you to buy [00:24:00] the idea for me.
[00:24:01] Like, would you, do you think you'd ever pay like 10 million, $5 million or $10 million for like an idea I gave you? No. Um, so like the, you know, the academic world business school world, the late stage investing world is a world that's about just kind of cash flows. It's about, you know, multiples and comparables of public companies.
[00:24:22] Um, it's about let's figure out, you know, look at some comparable exits and figure out what this company is likely to be. And then you get all the way to the, you know, like you kind of worked back over time to the really earliest stage and you're like, Where are these income from? And there are some methods that people have used, but mostly, you know, what it boils down to is, is generally the idea that well, VCs have an idea in their mind of what could the exit look like and why.
[00:24:51] And thinking backwards through time, we talked about this in the VC lab class of like, what are the w you know, what are the, what's the capital that has to go to the business in [00:25:00] order for the exit to look like X and then working backwards to what the early stage valuation needs to be. And so I would say that's the, that would be the trickiest thing.
[00:25:08] And I would say what makes it even more difficult? Is that the later an investor typically. When they invest early, they may attribute some light fundamental value to the company, but they also attribute option value to be able to invest more in that company. And so here and there, you'll see, like, let's say it's a later stage investor invest in a series a or a seed round.
[00:25:35] And they put evaluation in and you're like, that valuation is crazy. I've never seen, you know, it's a, you know, a series, a it's $20 million round at an $80 million pre-money valuation, which, you know, frankly, it's gotten, you know, common enough in the world that we live in right now where like you could look at, I could look at that and say, that's crazy.
[00:25:54] Because five years ago in the bay area, people talked about the standard series a, [00:26:00] which was like eight on. Right. That was kind of the standard series eight years ago. And now maybe the standard series, A's like 15 on 15. Right. And you see like 20 on 80, which if you asked any VC five years ago, they would've thought that's the most insane thing you can imagine, but.
[00:26:19] Um, you know, you've probably read about, you know, outcomes now we've realized there are much larger. We thought they would be in the tech world, but also when you get later investors investing earlier, you know, they're, um, they attribute fundamental value and some option value. And so they're like, oh, you know, like SoftBank's invested in some of our companies, they've got, you know, billions, billions of dollars to invest.
[00:26:43] And they're like, okay, well, you know, I'm happy to invest, you know, 70 $80 million in ShipBob now. Um, and I'll value an accident then like the next one comes like, oh, now I want to put 200 million in. And so, you know, they're like, well, I want to get involved in a company. That's a great company. And so, you know, [00:27:00] there's a lot, there could be a lot of squishiness with these valuations, so sorry.
[00:27:03] It was, it was a very, very long-winded answer, Matt, but hopefully that gives you some sense of the, the way that I think about metrics in, in the, in the VC world. So
[00:27:13] Matt Castellini: [00:27:13] no, and I think that that valuation. Step up, uh, year after year, almost that compounding step up is, is that ubiquitous or have you seen it in your geographic areas?
[00:27:24] Not just in Silicon valley, do you think it really has trickled down to the Midwest, for example, which historically was always viewed as sort of a conservative place you needed attractions, even at the earliest stages to, to, you know, warrants, any kind of, uh, Valuation, but, but I think, you know, over time, what would be your sort of sense of how have things sort of progressed even in the Mid-Continent on that front?
[00:27:48] Ira Weiss: [00:27:48] Yeah. I mean, valuations have definitely gone up over time, everywhere, you know, in the bay area, in our markets. Um, I think. You know, every time it seems like there's going to be a step back in [00:28:00] that, um, at least over the last, you know, really decade now, um, there may be a very brief step back, but it's like the valuations take, they can take a long time to go down to the private markets.
[00:28:12] And they're generally just going, they're generally just going up in the private markets. So, um, you, I don't know. I think mostly, honestly, it's about finding really good companies. And finding really good founding teams. And if, you know, if you, if you're lucky enough to invest in some companies that could be, you know, hundreds of millions of dollars of exit value, um, you know, you know, in some cases, bill billion, plus, you know, I mean, some of the, it's not that the valuations don't matter, but like investing in a.
[00:28:42] You know, what years ago, might've been a $3 million valuation and then became $5 million valuation at the seed round. And maybe occasionally now it could be eight to 10 million, you know, as long as you have a few companies that is really big outcomes, you know, it turns out to be okay. Um, the, the real, I think the real [00:29:00] challenge is how do you making that decision and choosing good companies?
[00:29:05] You know, if you end up in great companies, you're gonna, you know, you're going to have fun and you're going to make a lot of money in this profession. And if there aren't a lot of, you know, if you're not in a lot, any good companies, it's, it's, it's tough. So.
[00:29:17] Matt Castellini: [00:29:17] And we, we hit on valuations a little bit there, but, uh, I'm, I'm curious, you know, you guys obviously have a national network.
[00:29:24] Um, and so I'm sure you talk to VCs and there's also VCs based in Chicago who invest on the coast and they, you know, they're geo agnostic. So I'm curious from your perspective, What are some of the differences between investing in startups in the Midwest versus investing in startups, you know, on the coast, generally speaking to, you know, the startups here bootstrap longer, are there challenges that they may face, you know, being located in Chicago?
[00:29:49] Just curious about your perspective on that over the past 10 years.
[00:29:52] Ira Weiss: [00:29:52] Yeah. I mean, look at, you know, the cost of capital fundamentally is lower in the bay area and lower in New York and Boston than it is in Chicago for [00:30:00] startups. Like it's, it's just much easier to raise capital, um, in the Bayer that sad for, for, for companies and founders that are just starting out, unless you're an experienced founder, it's always hard to raise capital.
[00:30:14] And so, you know, I would say, um, you know, what, if you think about the Midwest. Because there's not as many capital sources around, there's still enough. The cost of capital is higher. And we need to think about that at every stage. Um, and then, you know, I think the other thing that I've noticed over time is like, it is harder to achieve hypergrowth.
[00:30:35] For companies based in the Midwest, then probably the Bayer or in New York, because when those companies, you know, we, we've got these, you know, a bunch of these companies now that are at these stages where they are hypergrowth or should be hypergrowth. And what happens in the bay area and elsewhere is like, maybe you can plug in very specialized talent at those stages.
[00:30:56] And you can plug it in very quickly and you can like, you know, switch people [00:31:00] out and get, you know, demand gen B2B marketing for someone who's done, SMB marketing, so and so forth. Maybe, you know, you post a job rack and maybe you get like 15 people who have done, you know, business to business marketing, uh, demand, gen marketing, um, for small and medium sized businesses.
[00:31:19] Um, and in Chicago, you post that rack and it's like, Too. Right. So that's what you have to get creative about. Um, and I think you do see, you know, good founders, good founding teams being able to like repurpose people and now in a COVID world where a lot more things are virtual. It's a little easier to get people.
[00:31:39] Who are not in Chicago, um, to, to be willing to like work virtually, um, especially with the tools now. And so I think you put that all together. And I think, I think fundamentally it is, it is a little bit harder to build billion dollar businesses, um, in the Midwest than it would be in the bay area. Um, but I think it's not it, [00:32:00] you know, it is very achievable, you know, we see that time and time again now.
[00:32:04] Um, and so. Um, I, I'm not sure. I don't have anything else to say about it, but I think that's hopefully, uh, a good, excellent.
[00:32:11] Matt Castellini: [00:32:11] No, I think that's, that's so, so insightful. And I think, you know, that echo is something that I think a lot of VCs in the show has said, have said, um, and another comment, or I guess, hypothesis that I've taken away from, you know, these conversations with VCs based in Chicago, is that right?
[00:32:27] In mid in the Midwest in Chicago, there is sort of a lack of, you know, those true pre-revenue, um, you know, pre-seed funds here in Chicago that will come in at the earliest of stages when it might just be, you know, an idea and a deck and an entrepreneur. And on the flip side, there's a little bit of a dearth.
[00:32:47] You know, post series B or even series B funds to take you to that sort of growth equity stage. Would you, would you agree with me on that? Or do you think, you know, there, there are funds that are starting to proliferate that might actually, you know, fill [00:33:00] that need in the future?
[00:33:02] Ira Weiss: [00:33:02] Yeah. I mean, I think those are two very different stages.
[00:33:04] So I'll talk about the region turn and like talk about pre-revenue companies. I think there are a good group of like, you know, C. You know, see pre-seed funds in, in the Midwest and particularly in Chicago, now, many of which will often invest at the pre-launch stage. So like for our fund that most people would consider like slightly later than seed, you know, we've made at least three of the major investments we made over the last, um, 12 months have been into pre-launch companies.
[00:33:38] Um, you know, one is a company I mentioned earlier, which is called ferox, which is a new futures exchange. That company was in. I mean, it was in stealth mode for a year and a half. Um, it had to get its, uh, it had to get regulatory approval by the CFTC. Um, and so we invested, I mean, well before launch it, you know, I mean really three funding rounds before [00:34:00] launch.
[00:34:00] That's pretty unusual. Uh, but recently, um, another investment we made is cup of called audit sites. Um, it's actually not based in Chicago, but it's based, you know, based in our geos they're prelaunch. Um, we invest in a company called Frank. Um, started them started by Logan, the hive, who's an experienced entrepreneur.
[00:34:19] Um, I think if you're an experienced entrepreneur, you can get money at the, at the pre-launch stage in Chicago. Um, we also invested a cup of coffee COVID markets. Um, that is, uh, it was a pre-launch, you know, crypto trading tool. And so I think you can get money at that stage in Chicago, but, you know, in some ways like the more experienced you are as the founder of the better.
[00:34:40] Uh, but there are. Sources now, you know, Chicago early-stage growth, you know, us, you know, Chicago meant a bunch of different groups that here and there and network ventures and others, like we will all, um, sometimes do pre-launch companies. And I think the more active the national markets are in our [00:35:00] GOs, frankly, the more likely it is like we're going to want to go earlier.
[00:35:03] So I think there's some of that, um, you know, but at the same time, Yeah, we could always use more money at the, at the pre-launch stage. Um, know I think the series B in later as a little bit of it is a very different category. Cause that seems to be like a historical, um, critique of the Chicago market where like there isn't a lot of like local series B and beyond capital.
[00:35:25] Um, you know, there's a group called jump capital great group that does a lot of investing, you know, series a series B, um, there's a group called valley. That as you know, it's based here in Chicago, but as an office in the bay area, an office in New York and was known really well for space X and Tesla, and many, many other, you know, great, um, great tech companies.
[00:35:45] Um, but they, and they do more national investing in the local investing. But really when you get to the series B and beyond, and in some cases, even for the series a, um, you are in a national market, Um, and so like, you know, let's say you look at [00:36:00] our fund, like we are not going to be an advantage. We're going to be at a disadvantage, try to invest in a series B company.
[00:36:07] Um, even some, you know, series solid series a companies, uh, because. There are national funds that have brand names that have invested in very specific spaces that are always going to have an advantage. And so, you know, why start investing late? You know, even like you raised a fund to do it, like you're probably going to get beat out consistently by, by coastal coastal funds.
[00:36:29] And so, and you see that a little bit. I mean, you have, um, Uh, uh, Midwest focus from lake drive capital, um, that, you know, in some ways, I mean, I think over time they haven't needed to do this, but for a while I thought, oh, you know, they had raised pretty large funds for the Midwest. And then we saw them like, seemingly at least at the time seemed to be while they have to pay way up for anything that looks like it might be the best, uh, Midwest company, uh, because they have to figure out how to win it.
[00:36:56] And so they were like bidding more than coastal funds might did. Like [00:37:00] ex-post I think. You know, maybe it looked like they were bidding more, but actually like, you know, all the valuations people paid in, it seemed like they might've been too low. But, um, but I think, I think that's the problem with these later stage rounds, um, where it is a national market and you know, who wants to be competing and stuff.
[00:37:18] You know, Sequoia and Lightspeed and, you know, and benchmark and emergence and Andreessen Horowitz and others, like we're not going to win. We're not going to win that game. Now, what we can do is here and there provide, you know, the feet on the ground and the local support for those companies that some of those funds may be interested in here and there, but it also depends on the entrepreneurs.
[00:37:38] And, you know, a lot of entrepreneurs don't even, you know, support, like what had been, they don't need anything. So
[00:37:44] Matt Castellini: [00:37:44] do you think that. Important for a VC, uh, such as yourselves, you know, who who's focused on a particular part of the country based in Chicago. Do you think it's important that you guys develop really strong relationships with those [00:38:00] series B and later sort of national funds, because then the founders that are coming to pitch you and that you're maybe potentially trying to win an allocation and.
[00:38:07] You, you have sort of those built-in networks, you can say, you know, we see you five years down the line needing to talk to X, Y, Z fund in New York or San Fran. And we can make that introduction is that, is that almost table stakes today for, for VCs based here.
[00:38:21] Ira Weiss: [00:38:21] Yeah. I mean that, what you're describing, that is what I always used to say and think, which is like, and, you know, I mean, it's played out a bit for us.
[00:38:28] Well, we have at a bunch of fallen capital for some, you know, some of our better companies. And I do like, you know, I was just in the bay area two weeks ago and that trip, I don't meet with companies out there. I meet with venture funds and, you know, particularly VCs to like pitch my companies. But I actually think VC's, don't really like getting introduced to companies by other VCs anyways.
[00:38:49] Um, they want to be introduced by other founders and they want to have a thesis. And so like in some ways, like maybe I thought we were really being helpful. Um, and you know, we are to [00:39:00] some extent, because I think it gives people a little extra comfort, but I think. Um, it's just such a natural national market at this point.
[00:39:07] You know, companies announced a financing, you know, as soon as it's announced that it's in PitchBook, like every, you know, every Tom, Dick, Harry, Sally Sue VC around the country that wants to be looking for a company in this space is going to know about it. And so I don't know. On the margin, it helps. Um, and literally, like I was out in the bay area two weeks ago, specifically telling people about, you know, some of our better stories.
[00:39:31] Uh, but I think the best companies that come out of the Midwest, you know, coastal funds find them, you know, I mean, I can give you the stories about our better companies and how. You know, I made some intros, you know, some of those turned into term sheets, but like for all of those companies, there were other thesis oriented investors that were national investors that just, just found the company anyways.
[00:39:53] So, um, that's a long way of saying like, I, I don't know how much help it is anymore. I think the way we can be helpful here [00:40:00] and there is like, Understanding the dynamics of, you know, follow on financing rounds and how to orient yourself for those. Um, knowing how to, you know, talking to entrepreneurs about getting the right introductions, which may or may not be from us.
[00:40:13] Um, you know, I think the near in the current market where financings are happening so quickly, For good companies, you know, the importance of a narrative, the importance of certain things. And, you know, I think some of that coaching can be helpful. Uh, but I think that the connections themselves are a little less useful than they used to be, to be honest with you.
[00:40:31] So no offense to my coastal brother and I, you know, and, and, you know, there are lots of exceptions where like, you know, there's one of our company, one of our portfolio companies, you know, that had, that hadn't really been public about what they were doing. Like there is a specific DC on the coast. May rent, listen to this podcast who was like, Hey, you know what great company do you have to be working on now?
[00:40:50] And I'm like, oh, I got to tell you about this company. And it turned out like he did really like that company. And he did engage a lot. And I think, you know, would, it could have been interested [00:41:00] in funding it. And so those things do happen. Uh, but they're just, they're just not as needed as they, as they have been.
[00:41:06] Matt Castellini: [00:41:06] And for anyone who may or may not follow you on Twitter, apparently you experienced your first ever earthquake on this trip to the bay area a few weeks ago. Uh, just real quick. What was that
[00:41:17] Ira Weiss: [00:41:17] like combat, they give them so someone's, someone's following me on Twitter, Matt. That would be you. I appreciate that.
[00:41:23] Um, yeah, I was in, um, I was actually in. The office of, of a venture firm called foundation capital with a former student of mine, Joann Chan, who's an amazing VC and we're sitting there and she's like, she looks up and I guess the, you know, the lights are shaking and she's like, you know, there's, there's an earthquake.
[00:41:44] And I'm like, oh, what? And we're in San Francisco. She's like, yeah, look at their shaky. I look up. I'm like, oh, and then it like goes on for a bit. And we were, and then like people in the office were like, well, we, I guess they have to get out of the building. So people stood up and they're getting ready to get out of the [00:42:00] building.
[00:42:00] And I'm like, is it okay? How big is it? She looks at how big it was. And my, you know, my gut reaction was like, I hope everyone's okay. I hope it's not that bad. Um, and. It was kind of cool for me. It's horrible to say, never been through an earthquake. Hopefully no one got hurt, but I'm like never been, I never happened to be in San Francisco when an earthquake was going on.
[00:42:24] Um, and so, um, again, hope no one was hurt, but I was like, huh,
[00:42:33] Matt Castellini: [00:42:33] what an experience? No, it's a, and it always makes, it makes for a great, good. It makes for a good podcast story at the end of the day. So, you know, I think, uh, uh,
[00:42:42] Ira Weiss: [00:42:42] It wasn't, it wasn't scary for me because it didn't get that bad. Um, and I never, you know, I think if I had been through any bad earthquakes in my life, it would have been, I mean, honestly it would have been like post-traumatic stress disorder.
[00:42:54] So I feel bad now for people who like, I don't think anyone was hurt and this sort of quake, but also like people have been through bad earthquakes. [00:43:00] Cause then you're like, uh, but, um, you know, hopefully. You know, hopefully there will be no bad earthquakes, but, you know, we just, we, we, we, we never experienced them in the Midwest in a way that's noticeable.
[00:43:11] So we,
[00:43:12] Matt Castellini: [00:43:12] we, we, we do not, we have our fair share of tornadoes and, uh, you know, now it seems like we have our fair share of unicorns here in the Midwest. And, uh, two of which that I need to mention, I'd be remiss if I did not during our time. Um, ShipBob and G2, uh, both companies, uh, that, uh, You know, you all at Hyde park had been a part of the journey from the very beginning.
[00:43:34] So first off, congratulations. And you know, I I'd love to ask, what do you think were the keys now looking back, you know, that they've reached unicorn status. What do you think were the keys to, to those companies, um, success over the years or, or that led to such, you know, scale that they've been able to.
[00:43:54] Ira Weiss: [00:43:54] Yeah. I mean, it, it, it, it's all about the founding team. It's all about their vision. It's all about their focus. [00:44:00] So, you know, we got involved in G2. Um, it was called G2 crowd at the time the founding team, um, had started a company called big machines, which was like historical Chicago tech success. Um, and they, um, you know, big machines was like enterprise software sold to companies and they, they.
[00:44:19] Kind of a developed this hatred for Gartner because, um, you know, they were a small company and they were like, well, our software is better than these big companies, but, um, you know, Gartner is telling everyone that these big companies software's better. And so they had developed this like hatred. And so they went to start G2, um, after they left big machines and, you know, they started, it was called G2 crowd and the idea was they like, they want the voice of their customers.
[00:44:44] In it to be out there for sure. Other prospective customers. And so G2 is like reviews, software reviews, and their pitch was, you know, I, I go to buy a ticket. I could get like 150 reviews on Amazon. I [00:45:00] want to go to a restaurant. I look at open table or talk one of our companies or something else. I get like, you know, 200 reviews before I go to , but I buy a, you know, $500,000 a year CRM system.
[00:45:12] And I, and I get the, I have to get a report from like an animalistic Gardner who has even used the software before. Like, I want to know. I want to know companies like mine and what their experience is. And so that was their vision. And I think it was like, it felt like, um, you know, You know, probability low that they could achieve it.
[00:45:34] But the fact that it was a team that had worked together before they were very passionate, they had a success under their belt. We were like, oh, you know, we're, we're ha we're happy to take that plunge. And so we got involved in the, in the seed round, right. Um, it was us one of the local venture fund and, you know, look, we've been so pleased, you know, just, it did just get you to court status.
[00:45:56] And I think we've been very pleased. My, my colleague, um, and a [00:46:00] partner at our fund, Tim carp is on the board of, of, um, of G2. And that, that is a company that now is. You know, it's definitely has a national reputation in the VC world because people use it for their due diligence as well. So, um, you know, so that is G2, you know, um, you know, the two other companies Loke locally in Chicago that we got involved in the really early stages that are unicorn or near unicorn status.
[00:46:21] One is called ShipBob, which is e-commerce fulfillment. And, um, I mean, look, you, you have no idea if it, I mean, when you're in getting involved, you have no idea if companies are going to be unicorn status, right. Are they going to be worth a billion dollars, but there, I think you had like really, really passionate founders, um, who had worked together before.
[00:46:40] And I think we, um, you know, we did get involved like by venture standards, it was very early, you know, we led the first institutional round, um, which we call the series a, but really was the seed round. Um, but because the company at the time, it's a lot of services, it provides e-commerce [00:47:00] fulfillment. Um, the same thing, you know, your Amazon package shows up.
[00:47:03] What does ShipBob do? Like they, you know, uh, physically wrap and, you know, put in a box, they've got a warehouse, they put it in a box, they send it off to you. Um, the same way that Amazon would. And, and so I think the reason we were able to get involved early, then. Um, was, it was mostly a service and just a little bit of software and that allowed a group like ours, which was local to get involved when they were, I think they were at actually at a run rate revenue of about 3 million, but it's all like shipping revenue.
[00:47:32] And not so interesting, you know, coastal VCs who are mostly looking for software companies and so really, really passionate founders who grew up together, actually in India, both moved here. One moved to go to Purdue, one, moved here to go to university of Illinois. Um, had one of them in some experience logistics.
[00:47:49] And I think we, you know, we've been very, just a really, really great passionate founding team that is, um, that really has become a leader in the space. And I think they're hoping to be, you know, their Shopify. [00:48:00] There's a company called Stripe, which is payments, uh, any commerce. There's a for companies like a firm.
[00:48:06] And then, right. I think we're hoping that people think, you know, ShipBob, if you're doing it comes with and it's on, um, it's, it's on track to be that. Um, so we're hoping for briefings and then you have another, these are Chicago based ones. We have another Chicago. Four kites, um, which is kind of effectively unicorn status as well, which is, um, which provides e-commerce.
[00:48:28] Um, it's our nine care is a supply chain visibility software, and they've done really, really well. Founder, Matt LNG, Jekyll, who keen from the space. And then worked at a company called, uh, ITU that was bought by JDA software and was at Oracle. Um, unfortunately went to Kellogg instead of booth. But, uh, but Matt was really, really, and we got there, we got involved.
[00:48:50] Pre-revenue really, really great founding story and we just believed, believed in the vision.
[00:48:55] Matt Castellini: [00:48:55] I, I mean, I think it's, it's 10 unicorns now in 2021 that Chicago [00:49:00] has minted it's, it's, it's been pretty incredible to watch. And I think in our remaining time, you know, I would just love to hear, you know, broadly speaking, you know, zooming out for a bit.
[00:49:09] Do you think there's anything else Chicago can continue to do to improve as a tech ecosystem? You know, what do you want to continue to see, uh, over the years, uh, that Chicago is an ecosystem, can do.
[00:49:22] Ira Weiss: [00:49:22] Um, it's a great question. I mean, I think my hope is, you know, really, I think about like how does Chicago get on the tech map?
[00:49:30] Um, and it does that through frankly, through bigger and bigger successes, um, you know, five to $10 billion. Tech successes, like, you know, really like the Grubhubs of the world, like the Paylocity is of the world. Um, you know, we have a really good crop of next gen companies like that. Companies like, you know, the ones in our portfolio, G2 ShipBob four kites, um, avant and amount that are also in our portfolio.
[00:49:56] Um, you know, a company called fast radius it's in a portfolio and [00:50:00] then, you know, big, big local ones, like active campaign. And relativity that are like multi-billion dollar private tech companies, um, and a bunch of other, you know, M one finance and cameo and Pret some, a bunch of others. I think, you know, historically Chicago's had a lot of companies where the founders, I think, you know, for a variety of reasons sold out when the companies were worth about a billion dollars.
[00:50:22] So you have, you know, um, clever company called clever safe that was sold to IBM. For 1.4 billion. You have a company called, um, Uh, uh, field glass that was sold to SAP for a billion. You have a recent one called tasty tray that was full for billion, a lot of founders, you know, it's it's really, yeah. It mostly their decision.
[00:50:43] They're like, well, this company, it's great. It's gotten to be at large as I can imagine for. Uh, but I think for, for Chicago to really be on the map we need, you know, that next level. And I think fortunately, you have a newer crop of founders. That are aiming, you know, that do seem to be [00:51:00] aiming for these larger outcomes.
[00:51:01] And I think, you know, maybe that's also, they're able to take a little bit more money off the table. Um, and so it's a little easier for them to do that, but we have a bunch of this next group and I think, you know, the way we can help, mostly it's just like funding more and more companies at the seed and early stage because you just, you know, you never know, in some ways in which companies are going to end up being that billion or multi-billion dollar company.
[00:51:22] And so the more, the more capital. They're the better, um, you know, I think really good entrepreneurs, you know, frankly, we'll figure it out. Um, and so the more we can get in the stable and the easier it is for them to get capital at the early stages, I think the better, the better off we will be. So
[00:51:39] Matt Castellini: [00:51:39] yeah, no, I think that's that.
[00:51:43] It's sort of that hyper scale hyper growth playbook that Silicon valley has really nailed over the last 50 years that, you know, it's, it's easy to argue that Chicago is just in the early innings of, of hopefully seeing something similar. Um, Fresno wise, this has been amazing. And last question, you know, would love to hear about [00:52:00] any.
[00:52:00] Thought leaders that you follow resources that you try and stay on top of, uh, you know, as you, as you sort of, um, look out at the landscape of all of the, sort of the blog posts, the newsletters, the podcast. We'd love to hear if you have any favorites.
[00:52:13] Ira Weiss: [00:52:13] Oh, great. Well, I mean, I love your podcast, Matt, and so I've been, I've been enjoying them and he's great.
[00:52:19] Um, I do like not, not as a thought leader, but I do like, um, you know, the 20 minute VC Harry Stebbings just because I get. You know, I get a flavor of lots of different VCs and that's what I like really hearing. Cause everyone kind of mostly gets to the crux of what their shtick is. Um, I didn't really fully get to my shtick here, but you know, everyone's got their shtick.
[00:52:39] Um, you know, I listened to a 16 Z podcast because I love those kind of feel like, you know, you'll learn what the next, you know, what the next gen is going to be like. And then. You know, I guess I'm a little bit old fashioned and I mostly still read the, you know, kind of the historical VC grades, like the Fred Wilson's of the world, the Brad Felds of the world, you know, Marcus Buster's of the [00:53:00] world.
[00:53:00] Um, you know, I love, um, there's a, there's a really, really great crop of up and coming DCS. And I just like reading, like DCS that people have. Um, and you know, one person that I've learned a lot from this guy named RJ Agarwal. Who's on the board with me at both ShipBob and four kites. And, you know, one of the VCs that I've learned really, really learned a lot from over time.
[00:53:21] And so he's written a bunch of stuff that I, that I, that I followed as well. He's not as prolific, but, uh, maybe it was, it gives you a little bit of a flavor of the, of the stuff that I, uh, that I found.
[00:53:30] Matt Castellini: [00:53:30] Beautiful. We'll check that out and add all those to the show notes. Um, really appreciate you coming on, professor vice.
[00:53:36] This is fantastic. We're going to have to have you on again, sometime during the school year, next year, maybe a in-person live recording from the classroom, something like that. Yeah. A live audience. Maybe.
[00:53:49] Ira Weiss: [00:53:49] Thank you so much for inviting me on Matt. Really, really appreciate it. Love what you're doing with these podcasts and these, you know, video cast in Chicago.
[00:53:56] I think it's great to get the word out there about what we're doing and yeah. [00:54:00] Um, and, uh, hopefully, um, you know, hopefully it was useful for some folks, so, yeah.
[00:54:04] Matt Castellini: [00:54:04] Amazing professor. Thank you. Take care.
[00:54:07] Ira Weiss: [00:54:07] Okay. Sounds good. Take care map.