Conversations with members of the Harvard and Radcliffe Class of 1992.
Hosted by Will Bachman.

Episode: 48

Caribou Honig, Founder at Sempervirens

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Show notes

Will Bachman and Caribou Honig, a member of Harvard and Radcliffe’s class of 1992, had a conversation about Caribou’s journey since graduating. Caribou graduated from the University of Virginia with a JD MBA and got his first and only real job at Capital One. During his tenure, he met his soon to be wife and had a couple of kids. In 2006, Caribou left Capital One and took a year off to spend time with his family. He then co-founded a boutique venture capital firm and launched a couple of industry tech conferences.


Hosting a Successful Conference

Caribou Honig was not expecting to be in the conference business, yet he found himself creating an industry tech conference. He began to focus on the subsector insure tech around 2015 and was looking for a good industry conference to attend. He couldn’t find one to his liking so he decided to create his own and has since been running the conference successfully. 

Caribou explains how he created the world’s largest Insurer Tech conference. With a partner, he launched the Insurer Tech Connect conference, which became a large success. Subsequently, they launched Transform, a conference focused on the impact of technology on the workplace. This year, they are launching other conferences such as Prop Tech, Logistics Tech, Food, and Ag Tech. Caribou shared that the process of creation was exciting and interesting for him. They lined up the venue and dates for the conference, which was held at the Las Vegas Convention Center.


Tactics for a Successful Conference

Caribou talks about how they organized and promoted a successful Insurtech conference in Las Vegas. They booked the Las Vegas Convention Center, set a goal of 600-1000 attendees, and ended up with 1500. They created a one-page PDF to explain the event and sent it to potential attendees and key speakers. They also asked venture capitalists to promote the event and offer discounts to their portfolio companies. In the end, the conference was a success, and it was gratifying to see 1000 people having conversations and networking.

Caribou  was a VC at a conference that wanted to make it easier for people to meet and double opt-in to meetings. To do this, they created an app where people could see who else was attending, what they were interested in, and describe what they were looking for. In addition, they had flags at tables with numbers so that when people double opted-in to meetings they knew exactly where to meet at what time. However, they had more people than they had tables and flags, so they had to make do with tape on the floor and numbered squares. In the end, the solution worked and people appreciated the simple social engineering.


Events for Venture Capitalists

Will asks what makes the event great for a VC, and how that could be different from what other stakeholders like an entrepreneur might value. Caribou explains that vendors can be a difficult stakeholder to work with because they often come to events with the intention of making a sale. This does not align with the investor mindset, so vendors can sometimes get frustrated when they are not able to get on stage. The conversation highlights the tension between creating an event that is tailored to the needs of the VC and the needs of other stakeholders.

The conversation discusses the post-COVID period, how people are now more eager to attend events, and that people are cutting back on attending certain events. Caribou suggests that certain categories of people, such as entrepreneurs gearing up to fundraise, can benefit from attending such events.


Prequalifying People for a Conference

Caribou  and Will  discuss how to prequalify people for a conference. Caribou explains that they would not prohibit people from buying tickets and attending, as it would be exceptional and bad behavior. However, they need to curate what’s on stage, so if a company is uninteresting to them, they won’t be onstage. They are open to the idea of companies paying for space in the Expo Hall. Pay-to-play on stage is something they avoid, as it cheapens the quality of the product. The events are all held in Vegas, as it is neutral territory, has great logistics, and it is difficult for people to just pop in and out. This ensures all attendees get the most out of the event.



  • 07:28 Planning a Successful Conference Event 
  • 11:46 Leveraging Word of Mouth and Earned Media for Event Promotion 
  • 14:11 Designing a Networking Event 
  • 15:57 VC Matchmaking at Honig Caribou Conference 
  • 19:58 Designing Events for VCs and Other Stakeholders 
  • 26:24 Social Engineering Design Insights: Bringing in Name Brand Artists to Increase Attendance 
  • 29:11 The Economics of Running a Conference 
  • 32:47 Impact of COVID-19 on B2B Trade Marketing and InsureTech Connect Conference 
  • 40:05 Prequalifying Attendees and Benefits of Hosting Events in Las Vegas 
  • 52:28 Investing in Innovative Companies and Harvard Courses 
  • 54:19 Overcoming Challenges in Physics Math Class 






Twitter: @caribou101


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92_Caribou Honig

Tue, Feb 14, 2023 3:24PM • 56:46


Caribou Honig, Will Bachman


Will Bachman  00:01

Hello, and welcome to the 92 report conversations with members of the Harvard and Radcliffe, class of 1992. I’m your host will Bachman and I’m excited to be here today with Caribou Honig. Caribou. Welcome to the show.


Caribou Honig 00:14

Thanks. Well, glad to be here.


Will Bachman  00:17

Caribou. Tell me about your journey since Harvard.


Caribou Honig 00:21

Yeah, so we’ll get no surprise I graduated a class in 92. I guess that’s why I’m here, then went off to University of Virginia for a JD MBA. As we all remember, 92 was a lousy job market, right as part of a recession. So choice between getting a lousy job or a good grad school went the latter route. After that, I went to Capitol one, which I like to call my first and only real job that I’ve had. But I spent a decade there cutting my teeth on how to use data in business strategies and how to go through hyper growth and all that good stuff. Great experience. In the course of that also met my my soon to be wife and that and married, had a couple of kids all that good stuff. Left Capital One in 2006. took a year off watching Netflix played with my kids, listen to the universe, ended up CO founding a boutique venture capital firm, ended up as part of that launch a couple industry tech conferences. And then most recently, with my youngest kid getting out of the house, going off to college, we became empty nesters loaded up the SUV with our dogs and a couple suitcases and headed west and relocated to Santa Fe, New Mexico, from Virginia. And that’s where I am now.


Will Bachman  01:46

Okay, so that is a quite compressed journey. So want to unpack that a little bit. So multiple strands. Let’s start with industry tech conferences. Talk to me about how one goes about starting an industry tech conference. Because it’s a little chicken in the egg, you know, to get one additional person to GM, you want to already say Well, yeah, we’ve been doing this for a while and, you know, 1000 people came last year. So how do you how do you how do you create a conference?


Caribou  Honig 02:14

I would not have ever guessed that I would be somehow in the conference business. I now like to joke that, you know, I’m part time event planner. If you have any weddings, bar mitzvahs, let me know I can help. But look, it’s it’s actually a much more fascinating, intellectually stimulating enterprise. And I would have ever guessed there’s a lot of social engineering, behavioral economics, things like that involved. As part of my venture capital work. Around 2015, I started to focus on a particular sub sector insure tech, you don’t get much nerdier than insurance technology. But there I was. And I was looking for a good industry conference to go to, couldn’t really find anything worth attending, or I’d meet the other investors, the entrepreneurs, the innovation, execs in the industry, and was like, Okay, I kind of need this conference to exist for my day job, maybe I should just go ahead and create it. Now luckily, I got connected to a guy who really knew what he was doing. He had launched a couple conferences. Previously, we had a sort of meeting of the minds. And so I was able to collaborate with him and together co found this event, which, you know, became the world’s largest insurer tech conference, again, you know, it’s sort of a niche, but, you know, we got, like 9000 people attending this past year. So you know, it becomes a pretty interesting event. And then I sort of got got hooked on it. Doing that, because it was so stimulating, and, and fun. And so then started collaborating with him on we launched another one called Transform focused on the impact of technology on the workplace, future of work, that kind of stuff. Which really, really came into the front with COVID. And now we’ve, we continue to collaborate, I continue to whisper in his ear, help them out with a series of others on things like prop tech and logistics, tech and food and ag tech launching later this year. But it really is, like social engineering and behavioral economics. We started with like, I’ve got to be able to come up with a list of 100 people that I can personally individually reach out to, that I know already. Let them know what we’re doing. And ask if they’ll sort of get involved, be supportive. And that’s what we did. And you got to get that flywheel spinning somehow, like you say, and, you know, and to some extent, it starts with personal outreach to the right people where you’ve already got a relationship, and then, you know, basically do everything in your power to make the event. If the event is successful, then they’re happy, right? So it makes the event part of their success, and that’s how you win.


Will Bachman  04:51

Okay, so let’s talk about the first year. And I want to hear more about this on terms of like the let’s start with the InsurTech conference that you started by then But what’s the name of it?


Caribou Honig 05:01

insurer Tech Connect insurer tech. We’re not. We’re not very creative.


Will Bachman  05:04

Okay. Well, I mean, right there, right there in the title is the value proposition. Okay, that’s right. So insure Tech Connect. So you starting with nothing, you have no location, you have no date or anything. Sounds like the first step that you had was you reached out to contacts you had in the industry and say, Hey, we’re going to organize a conference? Do you want to be part of it? And just walk me through like that first year of what it took to actually, you know, book, you know, find a location get people to come, how many people came in the first year? What was the, you know, was it you know, how long was it was it, you know, mostly talks was it roundtables, just walk us through the whole process, I’m


Caribou Honig 05:46

assuming you’re really interested in this tech tech conference.


Will Bachman  05:49

I am interested, I’m interested in how you would create a conference. This is amazing. So walk us through step by step how it happened. Yeah,


Caribou Honig 05:57

it is actually the act of creation, that is sort of so fun and interesting for me, you know, it’s not sort of part of why I’m addicted to this kind of thing. But so, so first, you know, construct that list of 100 outreach, but before reaching out to them. constraint. So we actually did line up the venue, we lined up the dates for it. It’s funny, I was actually at the Las Vegas Convention Center. And this is where my business partner in this, Jay, he, he had a couple of staff members, he had experience with this, he had contacts at different Las Vegas venues, and also, a lot of the real practical making it happen, he had that covered. And then But then the really important thing is to then create the one page PDF. And it sounds so stupid, right? But there’s an enormous difference between Oh, we’ve got a website, I can tell you all about it. And here’s the PDF that summarizes sort of what the value proposition is, who should be there, what we’re going to be talking about things like that. And when you can sort of email someone a Pete, the PDF, right, and I would hand them the pages, email them the PDF, with a sentence or two of explanation and context, then, like, it feels so much more real than just an idea. And so I didn’t want to just reach out to people before we had something tangible, to sort of show to them, ask them, and so on.


Will Bachman  07:28

How bold Are you like, the first year? Because I’m super curious, because, you know, some of my own businesses, organizing some events and stuff. And you know, when you do it initially, particularly the first time you don’t know how many people are going to show up. So what was your when you booked the LA Convention, Las Vegas Convention Center? How many did you plan for? Was this like 10 people? 100 people, 1000 people.


Caribou  Honig 07:51

So we said, if we get fewer than 600 showing up? Right, it’s probably a failure, we need to rethink whether there’s really an opportunity here or whether we’re filling the opportunity, right? We said if we get 600 to 1000, then we’re doing great, it almost for sure tells us that there’s a real opportunity and, and we can serve it. We ended up with 1500 people, which you know, actually had a scrambling with the fire marshal. And literally in the big plenary hall, there was standing room only, which in a sense, is not the great experience you want to provide to people. On the other hand, it created this sense of energy that you could not otherwise engineer, right, it’s back to the social engineering side. Right? If there’s a lot of empty seats, well, it doesn’t mean things aren’t gonna be valuable, but people don’t necessarily feel the Okay, this is this is the place to be, right. If you’ve got standing room only. People are like, Okay, well, everyone else is here. Right? Clearly, right. And they’ll make complaints about oh, there weren’t enough chairs. But don’t tell anyone about I don’t really care about those complaints. I mean, I do, but I don’t. Because the benefit of the energy that you get was just just on it. One of the greatest moments in my professional career is during the lunch hour, they’re taking a 50 steps back and seeing literally 1000 people having conversations and having a sense of like, okay, if I wasn’t part of this, you know, some of these conversations probably wouldn’t be happening. Like that. That is gratifying. You know, beyond almost anything else.


Will Bachman  09:32

Yeah, that’s amazing. Okay. So, you, you booked a venue, so say, alright, we’re going to invest and do this thing and just trust that people show up. You booked the venue. And then you create this PDF, one page and says, This is who’s coming to the event, and this is what it’s about. Come meet other professionals in the Insure tech industry. It’s the greatest and leading conference in the Insure tech industry and then And then when you reach out to those 100 people, those were what your sort of keynote speakers, people who you hoped would be on panels or


Caribou Honig 10:07

in some cases, in other cases, we really thought about the world in terms of nodes and super nodes, who were people who themselves were tied in to a bunch of other folks who would be interested in this event, who could get benefits out of the event and create benefit by being there. So a lot of them were VCs, right? If you’ve got a VC, venture capitalist who is actively looking to invest in these insurer tech companies maybe has a portfolio of five or six already? Well, they can be awesome for the outreach, because not only would we love them to come and attend and maybe speak, but how can we make it valuable for their portfolio companies to come? I know, Martha, you’re going to be coming. That’s, that’s great. And here’s a discount code for your portfolio companies to to attend as well. Or we can create a whole little program for them to have kiosks in the expo hall for a big discount. It’s again, it’s about how do you make it valuable for the people attending, but also for the people who, whom you’re asking to stick their neck out a little bit, and endorse or advocate for the event? And then once you’ve got those people’s like, oh, yeah, I’ll have a couple of my portfolio companies come, it could be valuable for them, then the more people who come, the better it is for those portfolio companies and for that for that investor. Right. So again, it’s a, you know, they call it networking for a reason, there’s a real network effect, the more people come, it becomes better for everyone else, as long as they’re, you know, the right type of people quality relevant to the topic matter.


Will Bachman  11:46

So then once you identified those kind of influencers, or nodes or super nodes, and got some of them to agree to it, How then did you kind of get the word out much more broadly? Did you kind of reach out to people directly on LinkedIn and send them a connection request? Or did you advertise it or how the word get out


Caribou  12:08

not not much paid advertising dabble with that a little bit, but that doesn’t usually move the needle very much for this kind of events? I don’t think it really is investing in word of mouth, it is investing in some time in so called earned media, right. I mean, I’ve done my fair share of podcasts, with, you know, in with insurer tech, or insurance kind of people, you know, writing articles helps. We’re being interviewed for articles that are interested in what’s going on in insurer tech, and then at the end, Oh, yeah. And the place to be more of these people is that insure Tech Connect in Vegas. So it’s, it’s much more it really is a lot of on the ground, spending the time talking to people explaining why it’s going to be valuable for them or for for other people that they know. And some of those super nodes, right, that I that I mentioned, you know, those can be like, trade journals, or accelerators focused on the category. So they’ve got a big footprint as well. But yeah, that sort of paid advertising, not really as much of a mix for us.


Will Bachman  13:24

Yeah. Now, there’s one movement that is called what is it? It’s, it’s called, like a thinking unconference or where they, you basically come together, and you get the right people together, but then there’s no agenda at all right? Because the idea is that, hey, when we go to these conferences, normally, the best experience that you have is actually that hallway conversation. So why don’t I make it just all hallway conversation? So that’s like one strand of thought, What have you learned? You mentioned social engineering a few times, what have you learned about, like, how to make it a most valuable event for people where they’re making connections, learning something, you know, build business opportunities. Tell me about how you’ve designed and experimented this thing.


Caribou  14:11

So we started with a very carefully curated focus group, right for just thinking about the agenda, and how to even the wording to describe what kind of conversations what topic matters we’d be discussing and the sort of tools that we designed the networking for in discovery and things like that. That very carefully curated focus group was me. Literally, we talked about, okay, we’re going to design this for a focus group of one, right, because caribou needed this for his day job. That’s why we’re creating it. So let’s make sure that we design it to really not just make it good for this archetypical caribou guy, but for me to make it great for him. And then if we succeed at making it great for him, then the best It is just that there are other people with similar needs, right to what caribou had as sort of the motivation to have this event in the first place. And I think that’s actually really important because there’s a temptation of okay, well, let’s make sure we make it good for the VCs, let’s make sure we make it good for the entrepreneurs, let’s make sure we, it’s good for these and for the ease and these these. And when you try to make it good for lots and lots of different audiences, you really run the risk that at best, it’s good for them, but great for no one. And at worst, it might actually be lousy for most of them, because you’re trying to serve so many different audiences. So having that focus, especially out of the gate initially, I think, actually really helped us. And yes, it turned out that there were a lot of other people who gained value out of the same kinds of things that I needed to see. Now. So that’s sort of the core starting point.


Will Bachman  15:57

Okay, what were some of those criteria? So you were, as you were caribou as a VC, right? So what were the things that would make it great for a VC?


Caribou Honig 16:08

Well, the opportunity to double opt in two meetings with people who, who sort of had something interesting for you. So that’s a lousy way of saying, we we provided an app for everyone attending, where they could basically see who else was attending, see what they were interested in, describe for themselves, what they are looking for, and then essentially, enable matchmaking. And then, one of the funniest things about this was doing at a conference, it’s actually quite hard to figure out sometimes, oh, are you the person I’m supposed to be meeting with? What do you look like? And what are you wearing stuff like that? It’s kind of awkward. And we big innovation. We had flags at tables, right? flag number one, number two, number three, number 20. And when you double opt in to meeting with someone through this app, it told you to meet at this time at table number seven. Oh, okay. Now, you don’t have to guess. Are you the person I’m supposed to be meeting? Oh, yes, of course you are, you’re waiting at table number seven at 1:15pm. Great. Now, we actually had so many people wanting to have those meetings, that we we blew through the numbers of tables we had. So we literally like created with some tape on the floor and a section, a whole bunch of like two by two squares, and had and put numbers on them and had people meeting there. It’s just so funny to think about, like senior insurance company executives standing around on spot number 87, waiting for someone to meet. But it worked like it was actually it solved the problem through simple social engineering. And I think that people really like that. I think that the look, there’s three ways of getting value out of these events. One is the learnings from you know, seeing stuff on stage. And we do try to curate for, for things which will be new, right? Not just motherhood and apple pie statements. But like, if there’s a panel, we really encourage them to disagree with each other on some things are great moderators bring out disagreements, because then at least you can have a real conversation. That’s interesting. Just a bunch of panelists agreeing on stuff that basically everyone thinks, oh, that’s boring and waste of my time. I think that actually, when there’s news announcements, right, having those be on stage, like, you want to have a sense of I was there when Ken described his new product launch and insurance. Okay, that’s interesting. The, so, you know, that sort of learning is certainly valuable. And so yeah, I’m, I’m not actually all that interested in the unconference. Because I think there is value opportunities in what’s on stage. Second is sort of efficiency of meeting the people that you already know you want to meet. Like, it’s actually better to, for everyone to fly to one place, and have 20 meetings with each other, and then leave, and then to have to fly to 20 places to have those 20 meetings, right? It’s actually very efficient that way. That’s why people are so exhausted at the end of our events, because they just compressed what would have been essentially weeks of travel and meetings into a few days, because they don’t have to travel at 20 places. So there’s a lot of value there. And then lastly, what I call serendipity, right? Just you sit down at the lunch table, and at a table of with seven other people. My job is to make sure that at least one of them is someone you want to talk to even though you didn’t know you want it to. They’re doing something interesting, and if not directly relevant, it’s at least provocative for your own strategy, like and so that kind of serendipity is really valuable as well.


Will Bachman  19:58

So that kind of discovery. aspect. Okay. Yeah. So I’m curious to hear the part about, you designed it for your needs, right? So what would make it great for a VC. And there’s some tension between what makes it great for VC versus makes it great for some other stakeholders, perhaps a entrepreneur or an exec at a big insurance company. Give me an example or two of what is something that, you know, some other type of stakeholder might think is great, but would make it less good for you?


Caribou Honig 20:34

Well, the easiest, it’s a slight cop out, but the easiest is vendors, right? Particularly old school legacy vendors that are basically coming to an event to make a sale, right, or to get leads. And there’s a lot of industry events out there conferences that are we describe as buyer seller events, right? It’s essentially a bunch of folks who are looking to buy, what are the toys for that we’re going to be marketing for next Christmas, and a bunch of vendors going, Oh, check out this stuffed animal, which makes these sounds isn’t that great. And they’re presenting to each other and trying to, you know, make the sale. There’s nothing wrong with that. In as much as it serves a purpose. It’s just not something that I would want to attend, particularly from a with an investor hat on. And so, you know, sometimes I think vendors would get a little frustrated with us, because in some cases, there was just no way they could get on stage. You know, what, essentially, we had to come to an assessment, what you want to present is not that interesting to the audience that we’re curating. And to the extent it’s a little bit interesting, we are too nervous that what you’re going to say on stage is essentially going to be a sales pitch. And know these folks are not coming here to be pitched. Right, not in some sort of transactional way about the next great thing on supply? Certainly not if it’s actually, you know, something that’s been on the market for five years already. You know, if you’re, we want to have people talking about things which are new and things which are not going to come across as a sales pitch, or promotion.


Will Bachman  22:24

So is there no kind of vendor hall like your typical conference will have?


Caribou Honig 22:30

No, so there is a big vendor Hall, an enormous I literally at this last one, I literally could not, could not find the exit for a few minutes. Literally, was it found myself in the middle of like, Wait, how do I get out of here? Oh, my gosh, I can’t actually find the exit. No, it there is, but it’s, and, you know, actually, one of the things I’m kind of proud of is, is how you transform a traditional buyer seller Expo Hall, which again, I don’t really, you know, find myself excited to go to, to something that is actually an appeal, right, as it is actually a valuable part of the product for for the people attending. And I think we managed to do that. Because it’s another way of getting educated. It’s another kind of serendipity, where you can wander through the hall, and you can actually get a get a gestalt of like, okay, where are the trends going here. And then you can also meet individually individual sort of innovators, vendors. And, in some cases, thought leaders who are explaining and showing what they have. So it actually becomes a valuable part of the product. Even though it’s not a trend, even though it’s not geared towards being transactional. I think that’s the, there’s nothing wrong with a company saying, here’s something that we believe is new that we think is interesting, that we think is valuable, here’s why. It’s the difference between the hard sell the pitch, and the this is so that you can we’re going to show you enough so that you can be aware of it. And then if it’s relevant industry, then we can follow up after the conference.


Will Bachman  24:10

And so, did you have set kind of ground rules or something to make it less transactional and more about, you know, educational, just in terms of how vendors set up their tents or, you know, have their brochures out?


Caribou Honig 24:28

No, look, I think it’s, it’s less around, you know, guidelines around that a little bit more around, you know, people get it, people get a natural sense. And they learn, you know, I will often tell them, like, don’t sponsor the first year that you’re there. We don’t, you know, come and buy a ticket or to come and walk around, get a sense of it. And then if you think it could be valuable for you for what your product is, is doing Um, you know, come in come next year and talk about sponsoring, right, we’d like to do the soft sell there. Much as we expect that out of the people who are, who are in the Expo Hall. And so I think that they get a sense that when insurance executives come to this event, and I think this carries over to the other types of events, we do other industry categories, too. They pretty quickly get a sense, okay. The industry executives are actually far more open minded during these three days than almost any other time of the year. Right. They are there to explore and to figure out what’s possible, not what’s right for them to do, but what’s possible. And then it becomes the foundation for figure, okay, what should they actually do. But there’s almost no other time in the insurance executives 365 days, where they come in, so open minded to sort of that discovery. And I think that sort of permeates in the conversations and how people talk to each other, and so on, that the best folks who are in the vendor category, figure that out pretty quickly, and make sure to adjust their pitch and the conversation, according to that, okay, you’re, you’re in an open minded discovery mode. Let’s talk in that context.


Will Bachman  26:24

Tell me any other kind of social engineering insights that you’ve had in designing this, whether it be you know, what food deserve? Or what kind of to include in that little gift bag thing that you have with all the handouts and stuff? Like, what are some of the, you know,


Caribou  Honig 26:42

you want all the state secrets here?


Will Bachman  26:45

surprising insights, some of the surprising insights that we that you wouldn’t necessarily expect?


Caribou Honig 26:50

Yeah. You know, I think that here’s a funny one, actually. So starting in year, year three, it was, we actually had an after party, you know, at one of the Vegas venues, and we actually brought in a name brand. Artists, I think our first year, trying to remember this sequence, I think our first year might have been salt and pepper. I think the second year was Billy Idol, for instance. And you’re part of the social engineering design there was we wanted to give the attendees an extra reason to stay that whole final day. Because if you go to these kinds of events, you do notice that there’s a bit of a drop off in the attendance on that last day, people are, understandably eager to get home. And so you know, maybe they take a 2pm flight out, so they’re only there in the morning of the last day or things like that. But if you can give them some sort of extra reason to, to extend through to the next morning, at least, then that benefits the event, right? Because again, it’s the robustness of the attendance, that makes these things fly. So when you’ve got a name brand at later that evening, then it just gives an extra nudge to keep people there. And then on top of that, it’s funny if they go and they really enjoy themselves, like they just sort of you get people ending on a high note, right? And it’s an emotional high note, back to the behavioral economics, right? You don’t you never want to ignore the emotional aspect of what’s driving someone’s behavior. And, you know, you sort of attend and you you see these things and feel them and it’s like, wow, that actually, people are are leaving on a high note. So someone cleverly commented, I went to insure Tech Connect, it was like, I went to a rock concert and an insurer tech conference broke out. Like, that’s what we want. That’s what we want people to feel like.


Will Bachman  29:11

Tell me about the what you’re able to share just on the economics of running a conference.


Caribou  29:19

Yeah. So it’s, it’s again, it’s much more interesting than I would have guessed. I mean, really, the economics of the conferences is quite simple. Your revenue is pretty much just two buckets. It’s ticket sales, and it’s sponsorships. That’s kind of it. And you know, the ratios between those two varies from event to event. It can be two to one and favorite tickets can be two to one in favor of sponsorship. It can be 5050. But like, that’s kind of your two sources of money for the event. And then you’ve got some pretty straightforward expenses. You’ve got the venue Have you got food and beverage at the venue, which is surprisingly expensive, because they mark it up 3,000% Because it’s Vegas, you’ve got your own staff, you’ve got some of the staff that you hire for the event itself. You know, it’s kind of straightforward. Economics there. You know, it costs, I’ll say, one to $3 million soup to nuts to launch an event. And I don’t just necessarily mean your one, right, it might be year one plus year two, plus even year three, or it all might be front loaded, but it kind of costs you you’ve got to plan to sort of consume one, two, maybe even $3 million, when you’re launching an event, when you make that decision. And that kind of holds true if the event is a smashing success, or if it’s kind of a lousy failure. Because you’re gonna, even if it’s a lousy failure, you can’t cut bait that quickly. And if it’s a smashing success, it actually starts paying for itself by year two or three anyway. So, you know, you’ve got to plan for a couple million dollars if you’re going to do this. But then if it’s a smashing success, you know, it’s not crazy to see, really good conferences, hit 10, or even $20 million of revenue. I mean, those are a little bit outlier. But those are well within the range of what I call a really good conference, and really good conference business. And then some of that should fall to your bottom line and start being a real profitable business.


Will Bachman  31:44

Are a lot of conferences launched every year and then fail like, is, I mean, is there just conferences out there? Just 1000s and 1000s of them?


Caribou  31:53

Well, there are 1000s and 1000s of conferences. It is a really big industry. I haven’t looked at stats recently, but I remember that a sort of b2b quote, in person trade marketing, which is, I think, how this would be classified. And, you know, since this kind of way, I think it’s something like $100 billion a year industry. So you spread that across a couple of dozen conferences, and you get something real. But no, I and yes, new conferences are launching every year. I don’t know, whether it’s measured in hundreds or 1000s. And you know, and I’m sure some conferences are dying, and COVID was kind of cold. Quite a few I think. I like to say it’s really hard to organize mass gatherings during a pandemic. Yeah. Like it’s really tough. What,


Will Bachman  32:47

what did you guys do during COVID? What what was the impact on your we cried a


 Caribou  Honig 32:50

lot, we whimpered, we complain that all the things you’d expect, what we did some, some digital activity. But there’s, it’s not a substitute. It’s not even close. There can be value there. But it’s not the same value. And it’s not the same magnitude of value. And it’s not the same business either. Right? It is a classic getting nickels and dimes instead of dollars when you’re doing a digital kind of quote event. But, you know, we wanted to support the community that we had built, we wanted to continue creating mechanisms for the kind of education discovery and serendipity as best we could. And, you know, a whole lot of biting our fingernails and trying to figure out how to navigate what was essentially unprecedented. There weren’t nearly as many Vegas conferences going on during the Spanish flu.


Will Bachman  33:43

When When did you? When did you pause it? And when did you come back? Were you were you back in 2022? Or?


Caribou  Honig 33:51

Yeah, we were back in 21, actually. Because we were that’s for insuretech Connect we were because that’s a autumn conference. So it was it was manageable. But I’ll tell you, we another conference, we did the one transform, it’s focused on sort of future of work issues. That was scheduled for late March 2020. So the aisle back, okay, it’s like think about like March 1 2020. And we’re trying to figure out what to do. We’re having speakers and attendees and sponsors, asking is it still going to happen is gonna happen? We’re talking to the venue about Okay, are you still gonna be opening Are you still gonna be open? Just a mess trying to navigate that that was one of the hardest situations professionally, just like navigate and figure out. We ended up not doing the show entry for two years because it was March of 2020. Then march 2021. way. But that’s a funny one because COVID was a terrible headwind for for that conference for two years, because we couldn’t have the conference, but it was also an enormous tailwind for the conference in the long term. Because COVID really catalyzed much more interest among VCs, especially, but also among entrepreneurs and HR community around this future work concept. And, and especially, what kind of digital transformation can be happening in different parts of the workplace. And that’s exactly what the conference is all about. Right? So we went from having, you know, I don’t want to say, in some sectors, lukewarm receptivity to the value proposition of that event, conference, to people being very excited and interested. We’ve actually got that conference coming up in at the end of March. So about five weeks from now, six weeks and, you know, sort of tons of interest in it this year, I think we’re hoping to approach 3000 attendees, which will be great.


Will Bachman  36:00

Wow. Curious, your perspective. I can imagine it going in either direction. So after COVID now is we are sort of coming into that post COVID period still with us. But moving on in life, is it I can imagine one possible outcome is that people were cooped up for so long, they’re now like, eager to get back out there. And they’re even more anxious than before to go to events. Or I can imagine you saying, well, people just sort of change their behaviors. And they’re used to doing zooms now. And people even though they can travel, they might travel for personal reasons, they’re just like a little bit more reluctant to do work related travel, they just on the margin, they’ll stay home, which direction are you seeing?


Caribou Honig 36:44

I think we are experiencing a post COVID Bump, increase in interest by people in in these kinds of conferences. I think that what you’re seeing also is a little bit of retrenchment at the same time. So if you’re the go to conference in a sector and a category, then people still go to and actually, that’s like the one they have to go to. And what they’re doing is they’re cutting back on attending some of the third tier or some of the hyper specialized events instead. So you might pre COVID, maybe you went to four or five conferences a year, post COVID, maybe you go to two or three, but you really go to those two or three, right, and you spend the whole time there. And it goes back to efficiency. In some cases, like, it’s actually very easy to justify, for certain categories, certain kinds of attendees, at least, are like if they were really going to be jumping on 20 airplanes in order to go see 20 clients, right? Or to pitch, if you’re an entrepreneur, you’re an entrepreneur, and you’re gearing up to fundraise in a few months, going to make a whole bunch of trips to meet with 20 VCs, one on one. That’s a lot of travel and headache. There’s a lot of efficiency for you that entrepreneur, if you can meet with those 20 VCs in the course of two or three days at one location. How could you not go to that event, if that’s an opportunity, it would be it would be crazy, right in terms of the amount of travel you’d be committing to by not going to that event. So that’s the kind of, you know, value proposition or your we’ve had, in some cases, an executive team will come and in some cases will even say, okay, we can find you some extra space at the venue, the day before the conference. And you can have your executive team meeting there the day before the conference. And then everyone from the team can go at the conference and see what’s going on in the Expo Hall see what’s the innovations are meet with a bunch of people, your counterparts at other companies. I mean, I think that’s really valuable and can actually be almost, you know, recession efficient as we’re contemplating getting into a recession at the economy here. So I think there’s lots of ways to make it. Actually a really big plus for people.


Will Bachman  39:19

Now, you mentioned that you want when someone sits at a table the lunch to have other valuable connections at the table people that they want to talk with. Do you like is there some sort of qualification to attend because you wouldn’t necessarily want someone there who is going to just kind of spam everyone that they meet someone who is not really super relevant to it, maybe they are selling like search engine optimization services are something you know that just that nobody really wants to hear about? Perhaps. So how do you how do you do like prequalify people or just I mean, because you have to balance versus on your side, you also want as many people to come as possible for, you know, more revenue, ticket sales. So we won’t


Caribou Honig 40:05

prohibit people from buying tickets and attending, right, sort of almost, in almost an under any circumstance. I mean, there’s bad behaviors that we could, you know, cause us to say, No, you can’t come. But that would be very exceptional, very bad behaviors. I think that, you know, the opposite end of the spectrum, if what they seem to be about as a company is just very uninteresting in our perspective, then, you know, they’re not going to get on stage. Because it is our job to curate what’s on stage. Like, that’s, that’s important and, and to avoid pay to play on stage as well. Now, if they want to be in the Expo Hall, you know, that’s a conversation. And if they’re willing to put their money where their mouth is, then maybe maybe we’re wrong, and maybe what they’re offering is actually more interesting than what we think. So, you know, if they want, if they want to pay for the space, probably okay with that. Now, again, if they’re, if they have a bad reputation in the industry, or something like that, that’s that’s a different matter, is


Will Bachman  41:09

that sell their wares, is that common in the expo industry, for companies to pay to then to be able to be a speaker on stage? Is that pretty common?


Caribou Honig 41:20

It’s, it’s more common than I’d like it to be. And we kind of pride ourselves, that’s something we really avoid, because it cheapens the quality of the product. And, you know, we, we are kind of product lead like this is, it’s about the experience, it’s about, we do NPS Net Promoter Score surveys at the end of the event, about sponsors and attendees, because we want to understand how we’re doing. And so, yes, we need to pay the bills. But in the ideal, ideal situation, there’s plenty of way to pay the bills without having people pay for the stage.


Will Bachman  42:06

And why Vegas? Do you do all your vents in Vegas? Do you know what’s special about that to people like going,


Caribou Honig 42:12

so we do all our events in Vegas, now, it’s a little bit that’s ultimately up to Jay. And, you know, I’m not quite as passionate about that as he is. But he has some pretty brilliant logic, actually, it starts with, there aren’t that many venues and that many cities around the country that can really handle the kind of numbers that we’re talking about? You can’t have a 5000 person conference in Richmond, Virginia, right, there’s just not the facilities for it. There are, you know, a handful of cities that can support that, but not that many, whereas that’s, you know, nothing for Vegas at these. Vegas also has great logistics and travel. Right, you know, obviously, tons of hotel rooms, but also the, the airline travel, there’s a lot of direct flights from all over the country and the world, to Las Vegas. So it’s easy to get to, relative to many other places. But the really important things I think about it are number one, that it’s it’s neutral territory, right? It’s it’s not, you know, in the heart of Silicon Valley, or based in New York City or something like that. So it’s nice that it’s neutral territory, and a little secret, by the way, people, particularly entrepreneurs, and VCs from the East Coast, are willing to travel to the West Coast, begrudgingly, but they will. But they prefer not to have to go quite that far. Entrepreneurs and VCs from the West Coast, almost refuse to go across the Mississippi River. So you know, at least doing it Vegas, it’s neutral territory. It’s not offensive to either the East Coast or West Coast folks, which is good. And then really important. So back to social engineering. Actually, this is your like this because it speaks directly to that. If you have places like New York and San Francisco, which are hubs, particularly technology and venture and things like that terrible, terrible places, in my view, to have an event like this, because what happens is that a lot of the most interesting attendees, and the speakers will just pop in from that area. They’ll come and speak or you know, come for half a day, and then they’re gone. Right? Because it’s easy. And even people who might come in from out of town as a speaker, let’s say, right, they’ll come in, they’ll do their their little presentation or their panel, and then they’ll spend the rest of the day outside of the events meeting with people in that city. Well, that’s useless. That is a very low value for the attendees. Right that this interesting person spoke but then left. And that doesn’t happen so much in Vegas, right? If you come in to an You bet in Vegas, there’s not another 20 people outside the conference that you want to go speak to, you can’t just pop in, right? For two hours and then pop back into your office. Because your office isn’t in Vegas, right? It’s in New York or San Francisco or Chicago or Miami or somewhere, but not they, but not in Vegas. So Las Vegas is actually an island. Right? Now, if people think it’s in the desert, no, it’s actually an island when you come there, but you are insulated, like an island, from the rest of the business world. And so you come there, you meet with the people who are at the event. And that’s back to that I’m trying to I’m trying to meet with the people that I know I want to meet with efficiently 20 In two days, I’m trying to get what kind of discovery there is in the serendipity, which only happens if people are actually staying in the proximity of the conference.


Will Bachman  45:55

That was so fascinating to hear. I have never really heard that perspective on Vegas. And it really helps me understand the city so much better. The value is that it’s not where people are living and working. Yeah, that’s, that’s interesting. Tell me a bit about the future of work. So you have this conference on the future of work? What are some of the things that you expect us to be seeing in two or five or 10 years? Yeah, so


Caribou Honig 46:23

it’s funny how a person’s career takes these windy roads. And like I was back back in the harbor days, I was physics and philosophy. So not exactly the natural glide path being a conference organizer. But, you know, actually, I found the conference thing with insurtechs Connect. So fun. I actually left, the VC firm that I co founded, started this, this other one, again, with my partner, Jay, focused on future work, whatever the heck that means. And one thing led to another, we’re actually now I’m joined back up into another venture capital firm, that’s entirely focused on that topic, right. So it’s funny how these things sort of twist and turn to each other. So So I’ll give you my perspective, both from the, you know, what I see at the conference, but also what I see as part of the this venture capital team. So as I say, COVID really served as a catalyst for digital transformation in the workplace, there’s a lot under that there’s a lot of evolution in health care and benefits associated with this. So you know, as, as I’m sure most people listening to this know, you know, COVID comes along, employers are trying to figure out how to help their employees, you know, almost literally stay sane, when they’re working from home, maybe with a kid or two in the background, right, getting much less of the in person interaction with their colleagues, but still needing to be productive. And, you know, really something of a mental health crisis for the employees. So employers are trying to figure that out, you know, circa 2020, and a whole lot of what we would call digital point solutions, serving topics, like mental health for employees, already were in place, but now the sort of need for them dramatically increases. And the willingness of employers to lean into providing some of these these ancillary benefits, right, increases dramatically as well. So, you know, so for us as investors, right, we were some combination of fortunate and Smart Investing ahead of that in some mental health solutions for employees. But we’ve also seen lots of other digital health point solutions, that, again, make sense to be provided by the employer as part of a total package. And a lot of the dialogue around that is actually well, if I invest in this ancillary benefit, could have actually saved me the employer, some money in the medium to long term, you know, if I, if I invest $5, every month for every employee and making sure they’ve got good mental health benefits or good addiction, treatment benefits, those that actually saved me $20 A month in some other health costs that would be incurred, if this person doesn’t get the mental health or addiction support, like that kind of calculus has really been happening. And, and I think that actually, you know, both the CHRO, the head of HR and the CFO, right, can sort of both get behind that kind of proposition. Yeah, well, we’ll spend $5 more per month on these employees on this benefit. And we’d have good almost actuarial reason to believe it’ll save us 20 bucks a month. That’s a good catch. So that’s a good benefit to invest in. So we’re seeing that we’re also seeing now this is going to start getting super nerdy again, but you know, what I would call the SAS application of human resources. Right. So what I mean by that right SAS application, right verticalized Software as a Service, new solutions coming into place, replacing a whole lot of processes that are happening by employers that combine, you know, Microsoft Excel, email at a bunch of HR admins doing things that can be done a lot more efficiently, and a lot better for the employer and the employees in software. An example this employee leave, like, employees take leave all the time medical leave, parental leave, things like that. And many companies are administering that with Microsoft Excel, and email and a couple HR admins. And it makes for a lousy experience for the employee, hey, what’s the status of my leave? Is it approved yet? It’s costly for the employer, that kind of stuff is just beautifully replaced with the right kind of software. So we’re invested in a company that has that provides that kind of software to employers to help them and the employees better manage their leave, right. And then like, it’s, it’s kind of, in some ways that sort of backwater area, like, it’s not something that it doesn’t have the sizzle of self driving cars. But it’s actually really important that if you’re that employee, you know, taking leave, and you want to find out the status of it, and how many more weeks you have left, and things like that, that’s actually really important for your life, day to day. So that’s another and then, you know, there was a lot of infrastructure being built, I’m I’m a FinTech InsurTech. Guy these days, given my background. And, you know, we’re seeing companies that are building the infrastructure to unlock payroll data, right for the benefit of employees to get better loans, things like that. So there’s just all sorts of different different dimensions, where there can be innovation around this. I’m too, too old and set in my ways to actually think of very many of these ideas, but it’s great seeing the entrepreneurs, one after the other, just demonstrating great ideas, and then proving it.


Will Bachman  52:28

I want to ask you turn the dial back to Harvard, and what were the courses or professors that, if any, that continue to resonate with you?


Caribou  Honig 52:41

Yeah, you gave me a heads up that you might ask this question, which I appreciate. Because this would be a really tough question to write on the fly. So good news, bad news, right? I don’t have a specific professor or class. I’m like, Okay, this inspired me and sent me on my way. I almost have the opposite. Right? In that, you know, here here I was a cheery freshman thinking that maybe I can do physics as a career. And I take the entry physics math class, it might have been, like math two, V three, a or something. And it absolutely kicks my ass, right? You know, I was like a smart, high school math guy. And then I take this entry, math for physics majors class, get a C plus. And I’m like, Alright, I still want to do this, I still want to learn college level physics, sharpen my skills. But you know what, I’m pretty convinced that I ain’t going to be earning no Nobel Prize in my career. And rather than banging my head for 40 years, doing physics and making barely a contribution, maybe I should have an eye towards what I’m going to do after that, instead of that. And so, in a sense, having that class be so hard for me, set me on on a good path of finding an area where I could actually make some sort of meaningful contribution. In my field.


Will Bachman  54:19

I might have been in that class with you. I took math 22 A, and there was like math 21 A, which was linear algebra based, like regular, you know, linear for non physics majors. 22 A was for physics majors. And I remember that it was this photocopied textbook that Yes. Okay. Like


Caribou Honig 54:39

the stars and stuff? Yes. Some sort of weird star math or something.


Will Bachman  54:44

And the challenge with that textbook was that it was the preprint version. And there was a lot of errors. So you would be trying to understand why is this e to the t? Like you’d work it out and try to derive it just doesn’t make sense. And then it’d be like, go to the portal. Esser and oh, yeah, that should be like e to the l sorry, or e to the minus t, like.


Caribou  55:05

So you’re That’s exactly it. You and I were in that class. And I don’t know how you did, but I got a C plus. And that sent me on my way.


Will Bachman  55:16

All right. That was, at the end of the semester, I gave the professor like, two or three pages of irata. Because, you know, he tried to derive the equations, and it just didn’t make sense. Normally, you can trust the textbook, but this was like, the textbook itself was a bit of an exercise. So caribou? Where can people find out about you and about these conferences, you can share any links or other ways of for people where people can go to find out more what you’re doing? And yeah, so


Caribou Honig 55:51

I mean, look, the easiest way, I’ve got a pretty good couple of breadcrumbs on on the Google Now. So if you care to Roenick, I usually show up. I actually, actually, battery easier to remember, if you Google stupid career decisions. I am last time I checked, the number one organic result. So just look for stupid career decisions. And you’ll find me


Will Bachman  56:19

that’s not that’s quite, quite impressive. I’m now definitely gonna go. Go check that out. Because I’m curious for that link. We will include that link in the show notes. And I’m surprised that you’re the number one result for caribou Hornik because there’s probably so many caribou out there. But care stupid career decisions. Okay. Caribou. This has been amazing. Thank you so much for joining


Caribou Honig 56:43

  1. It’s my pleasure. Thanks for having me.