Navigating Co-Leadership and Tech Innovations with Elizabeth Caley

I think a lot of the folks, a lot of your listeners are probably going to have done the same thing, which is as you go through your career in different organizations and working with different people, you're making lists, right? You're making lists of, oh, that seems to work. I see where they made that decision. I don't know if I would have made that decision. I like the way that manager handled that situation. You know, you're sort of like keeping track of like, hey, if I ever get to do this one day, I'm going to learn from this situation and this person.

Welcome to the Startup CEO Show. I'm your host, Mark McLeod. In this episode, I sit down with Elizabeth Kaley, co founder and CEO of Poppy. Elizabeth is a co CEO. That's not supposed to be a thing. It's not in the standard playbook, but she's making it work and we explore that in this episode. Her fellow co CEO and her have a really long standing relationship. And Y Combinator, when they ran a study on all of their companies, found that the biggest predictor of success was, was the length of time that the co founders knew each other. We dig into that and lots more in this episode. Check it out. Elizabeth, welcome to the Startup CEO show. It's a true pleasure to have you here today. How are you?

Thanks, Marc. It's an absolute pleasure to be here.

Amazing. We were just chatting a little bit before and it's been a minute since we saw each other last and like a totally different world pre Covid and all of that. So yeah, really, really great to see you and maybe just to kick things off, could you tell us what Poppy does? And I'm always fascinated by the origin story of a company, particularly because other than the fact that it's science based, it seems very different to your last company.

Yeah, I'd be happy to do that. So after we sold our last company, ran it for a few years in California, my co founder and I, Sam, decided, you know, we were serial entrepreneurs. We couldn't deny it anymore. And so we started thinking about what kind of company we wanted to run because we know it's, you know, if you're lucky, it's a, you know, 5, 7, 10 year plus process. And so we, we looked back at what, what kinds of technologies were intriguing us at the time. Breakthroughs, you know, what we had specialized in and still specialize in is things that are just about, you know, in research, but just about ready for prime time and finding those. So we had commercialized technology that came out of IARPA before in the US and done some very early machine learning work in our previous companies. And so we're like, what is just about ready that deserves to be more widely available and that we think we can actually help with scale. So we spent a little bit of time at an organization called SRI International.

I haven't heard of iarpa, but I have heard of sri.

Yeah, IARPA is essentially the information version of darpa. So still the fence, but on the data information side. But the question we had for the folks at SRI was Sam's background is biomedicine. And the last company, Meta, was a lot about surfacing biomedical research to scientists so that they could accelerate their science better. We asked all these researchers, these engineers, these leading edge thinkers, what would it be possible to do if we actually, instead of inventing a new drug or a new vaccine or a new medical device, if we actually took things that are taken for granted in biomedicine and hospital and labs and actually brought it out to the real world, so to speak, what if we brought it to buildings? And that was one of the original theses and we started to explore the measurement of airflow and how almost half of what we all get sick from every year is because we are spending time indoors, 90% of our time, typically breathing out, breathing in something that somebody else has just breathed out and that's how we get sick.

Sounds awful when you say it's just.

This, you know, air soup that we're all breathing all the time, 10,000 liters of it a day. And there are very few regulations, very few guidelines. Unlike food, unlike water, unlike outdoor air, Indoor air was a little bit of the wild west. And so in 2019 we said, who, who should care about this most? You know, long term care facilities, cruise ships, et cetera. And then the pandemic hit. And so we, you know, went to market much faster than we thought we were going to. And we built some hardware and we went out there and we started testing code in the air. A lot of things have happened since, but that's really where, where our origins came from.

So is this like a core technology that you've licensed, you've packaged it into a product and you just built a service around it? Like, I guess, what's the ratio between, I guess, stuff that you found versus stuff that you built?

Yeah, this one ended up being a little bit different than projects we've done in the past in which it's all our own ip. What we did was we found amazing researchers who have been doing like research in a niche area called, you know, the built environment and aerosol science in the built environment. And we made them all our advisors and we started researching how much sensitivity would you need? The first version was how much sensitivity would you need in order to detect something like Covid in the air or any other kind of virus or bacteria or potential things like mold. And given that it's so much more dilute than saliva or blood, is that actually possible? And we went through a whole bunch of different iterations of hardware, took advantage of 3D printing and a whole bunch of smart people putting stuff together and started experimenting at customer sites and then bringing stuff back to the lab and figuring out is our data, what we're showing with the samples that we've collected, does that actually represent illness of people in the buildings? And started iterating from there. And so it's all R.I.P. we've patented it. And then we patent all the updated versions since then, including some of the processes that are now part of an international engineering building standard. So we're the only ones that have the ability to do an automated version of a test that now is standardized in the H Vac industry. Cool.

That's really interesting. So different from the standard, I don't know, SaaS CEO that I have on here. This is fascinating stuff and way beyond my pay grade. I do want to dig in a little bit more, but, you know, it's not every day that I speak with a CEO where, you know, your prior company has impacted so many people, because there's probably a hundred percent chance that everyone listening or watching this show is a Facebook user. And of course, Facebook made the world's most expensive domain purchase everywhere. When they bought your prior company, meta.com of course they bought it for things other than the domain. Of course. Of course they didn't buy it. Mark bought it. But, you know, I don't know how much you can share, but I think it's just fascinating. I heard some wild stories from Sam during the time at the Chan Zuckerberg initiative. And he'd be just down there and like, I don't know, Bono would be walking through the office like any. Anything you can share. I think folks would just love to hear just a little anecdote about that experience because it seems like you. You all entered another world for a period of time.

Yeah, it definitely felt like that. Yeah. So. So Sam started a company called meta.meta.com and we were based out of Toronto mostly, most of the team. And it was an early machine learning company way before AI was cool, but we were taking advantage of the fact that especially Toronto had like a hotbed of cool, great AI researchers at the time. Before they had been farmed off by Google and Facebook and everywhere else. So we got to make some amazing breakthroughs in natural language learning and natural language processing. And then we were starting to commercialize. We had raised a few rounds and we were approached, which we thought was for an investment, but ended up turning into an acquisition of a brand new philanthropy. Ended up being, at least at the time, the best funded philanthropy on the planet, which was run by Mark and his wife Priscilla. And it was really just getting off the ground, especially the part that they wanted us to incorporate with, which was the science part. So what we felt was, it was very unusual. I don't know if it's happened before or since that a tech company gets acquired by philanthropy. But we, we joined and our team was actually bigger than their team at the time. So that was a fun, you know, like a different kind of acquisition in a way. And then it was, it was because our missions aligned. We, we had started the company because we wanted to help accelerate scientific progress and that's what they did too. So we were then enabled to make all of the products and technology we had developed for free to scientists, which was like a dream versus huge selling.

It to just remove the need to make revenue and just boom here.

So, so, you know, we were selling to life science companies and drug drug manufacturers for their research and then trying to give away as much as we could to scientists who weren't in those kind of labs. But it's like, okay, now everybody can use it. And so all of that was happening@meta.com they came to me early on, just after the acquisition and said, you know, we should move everything over to meta.org that's fine. We had meta.org as well. They're like, it's a philanthropy, it's a not for profit, so. Or it makes more sense and you should sell dot com. And I said, thanks for the suggestion. I don't think we should do it. At the time there was a competitor to Oculus called Meta. I don't know if they're still around either. And I'm like, I don't think the boss would love it if I just gave up meta.com and that they could potentially pick it up. So I'm just going to sit on it. Moved everything over to meta.org and then we were with the company for a long time, grew and ran one of their biggest tech teams. And then after we had left the company, all the rebranding and all that kind of work was happening. And so a lot of our logo, the.com, the domains, the trademarks, all that kind of stuff ended up shifting hands. And so now a scrappy Toronto startup ended up their domain being used by billions of people ending up in a given day. Which was definitely a weird thing to wake up to that morning.

When you went to godaddy way back when you probably didn't think the domain was going to have that kind of impact.

No, no.

So going back now to Poppy, you know, where I have been, Expo where I've obviously I follow you and Sam on LinkedIn and the things that I've seen in the early days were really around air quality and offices and you probably have other use cases. But I'm just curious, you know, the biggest change in Covid is from that came out of COVID is we stopped going to offices. By and large, especially in the startup community, it's pretty perhaps not as extreme in other verticals. And there was a time where, you know, as consumers we were obsessed with air quality and we were afraid. And you know, I just went to Costa Rica a few weeks ago and I was on a retreat and it was a really important one, so I didn't want to get sick, so I wore a mask and like my wife and I were like literally the only people on the plane with a mask and the only people in customs with a mask. So we've all moved on. So I'm just wondering, like, what is the, I guess the curve of awareness or interest in air quality and yeah, how is Covid and I guess now post Covid impacting your opportunity?

Yeah, it's a great question and I think if there was ever a test for how nimble can a startup be, it might be running a Covid related business during and after Covid or a business that started off in that space because it wasn't even, it was every week or even multiple times a week, depending on who we were talking to in what state and their political leaning in the states and especially in the us people's attitudes of what they were willing to do and not willing to do and whether they were looking for a solution or if they just didn't like the word anymore or whatever. Literally it was a constant tap dance of what's somebody feeling about the kind of thing that we're, we're offering. But what it did do for us very positively is it let us probably get, you know, five or Six years worth of product development done in an incredibly short period of time, because there were a lot of organizations that were willing to try anything. We're willing to work with small companies that never heard of before, like put hardware on the walls in their office, make changes when we tell them that there's something happening. So we got to stop outbreaks. We got to help businesses in a way that would be pretty hard in a regular environment. But what it did is it gave us, because we ran so many tests and worked with so many different kinds of organizations, from royal palace to subsidized daycares.

Right, like literally a royal palace.

Literally royal palace, yeah. And everything in between. Factories in Ohio and dake daycares in Oakland. We got to understand the problem, we think, better than anybody else. And we got the data that nobody else on the planet had ever done, because a lot of what we were doing was installed systems. So we saw how things changed hour over hour, and that really led us to our breakthrough. That is the core of what we do today, which is not about detecting Covid in the air, but it's really about measuring digitally how air flows in the building, which, believe it or not, didn't exist before this. And so it was one of those things where the pandemic helped us accelerate. Not only people understand people's sensitivity, what hardware works, what hardware doesn't work, what pricing, who buys, who cares? But it led us to a breakthrough because at the core of it, the public might not care as much anymore, Or a lot of the times you don't see the actions on the outside of people wearing masks or something because they're concerned about getting sick. But at the people running the buildings, especially commercial buildings, they're the ones that are dealing with not only health and occupancy, but energy and buildings. And that's the breakthrough that we had, which is exactly the same testing that we were doing. We're helping people, a building owner, save money. And in a time where occupancy is lower than average and lower than normal, it's actually a. A boon for us because it helps us help them adjust how much air is in their building based on how it's getting used at any point in time in the day. So it was one of those things that I probably couldn't have seen the path through. But because we were incredibly experimentally driven and always looking at the data and collecting the data and talking to the customers, it led us to where we are today, which is in a really good spot. Post Covid given a Whole bunch of people are working from home or there's hybrid situations. And basically the way buildings were built to be used are not the way they're actually being used today. And so that, Delta, is something that our technology can help owners take advantage of.

Could you expand on that point? What do you mean by that?

When a building's commissioned, an H vac system goes in for given predicted occupancy on this floor versus that floor, or this part of the floor versus that part of the floor, and that was probably for most of our office building stock, just to pick an example, was built 20 to 30 much longer in some geographies ago. And then you add in schools and factories and all sorts of other types of buildings, and they were probably built maybe 100 years ago. And how those buildings are actually getting used today and how much clean air per person is required in that building at different times of day at different times of year so that you're not wasting energy and actually contributing to the climate change events that are causing us to have a lot of these problems in the first place. You're saving energy, you're saving money. Because what we can do is we can help you match it to how a building is being used or a part of a building is even being used at any particular point in time and keep everybody in compliance with the new guidelines that are out. So nobody's breaking any rules or cutting any corners. It's like you comply, but most buildings are way over most of the time. How do we actually get you to keep people safe and save money at the same time with energy, do you.

Actually offer like a quantifiable roi? Is there, there's a business case for this?

Yeah, yeah. And.

Oh, that's really cool.

And because we're, we're about testing, what we do is we go in and we do a baseline test of a building or, you know, a portion of the building, and we say we think this is how much you can save. And then they make adjustments to the H VAC system based on our recommendations. And then we go in and we say you're in compliance and given your last couple years worth of utility bills, this is what we think you can save over the next year. And so we're just working through now getting all the proof for all of that. But it's all been done with independent energy modelers, specialty agencies that do this kind of thing full time. And the customers are starting to see the results on the energy side, which is absolutely amazing. And it's something that buildings are Dynamic enough that there's an ongoing benefit to knowing how your building is performing at any particular point in time.

So your customer is not the tenant, it's the building owner.

And that's the major shift that happened during the pandemic. So it's not always that. Sometimes it's a large Fortune 1000 corporation who has bank branches and head offices and they're the previous tenant. And so they have a lot of sway over the landlord. But often the time it's the people who own those buildings or portfolio properties that are, you know, looking at ways to save costs because of occupancy numbers.

Interesting. Well, I gotta say, now I'm only in my little startup bubble, but every CEO I speak with wants people to come back to the office. And I think with, with bigger companies, I know if some have mandated it. And so it just feels like this might play a role in, I guess, giving comfort for people to come back. I think there's reasons why they don't want to come back. You know, it's not just about safety. It's like, you know, you're up in Canadian cottage country right now and that doesn't sound unpleasant, but safety maybe is a part of it.

For some people it is. And a lot of what we were doing in the pandemic, we actually did the largest clean air survey of, we chose downtown Toronto and we surveyed hundreds of buildings. And we actually went in and we did testing all sorts of different spaces. So like where you probably go for lunch if you work downtown Toronto, the path for the go train, et cetera, et cetera. And you can see in the native, where there are places that are very over ventilated and where there are places where I wouldn't want to be without a mask. And the example you gave earlier on a plane, one of the original advisors we had on the scientific side, who has been research, did a bunch of this research actually for the usdod. Being on an airplane at altitude is one of the safest places you could be.

Safe. Yeah, safest, that's right. But not, not on the ground, not.

Taxiing, and definitely not in those walkways. And so it's that kind of information that led to the White House pushing basically the standards body, the engineering standards body that is global. ASHRAE Whitehouse said, how do we set building standards so that we pandemic proof our country in the future? And that was part of one of the standards that we helped write. How do you actually test for it? And the goal of that standard called ASHRAE241 is to have an equal level of risk, a low but equal level of risk, regardless of what kind of building your own home, you know, multifamily residential. So in a condo building or apartment building, at a school, you know, shopping for your groceries or going, you know, to the office or to the factory. And that's how those standards have been set. And that's what, you know, we're measuring too, on 99% of the time these days.

Fascinating. So we just talked about office versus not you're at home today. What are your thoughts on pros and cons of remote work?

It wasn't such a big shift for me personally or I think a lot of our team because it's a way I've worked in a long time, but that's because I was in tech for my entire career and at large multinational tech companies. So I remember 20, 25 years ago, even before I joined Microsoft and helped work on the Unified Communication product, which was the pre teams product, I was managing a team in like 11 different countries around the world. And so the tools have gotten a lot better. And the situation of more individuals working from home versus like three people are in this office and have to work with three people in that office and 20 people in that office, the dynamics have changed a little bit. But the pro for us as a smaller organization has been I can hire the right person regardless of where they are. And so we've been able to put together like a team of extreme experts who have family and live in Denver, Colorado and will never leave Denver, Colorado. And we're exactly the right person for us and what we're doing at this time. And I can have them as part of the team. So. But the benefit, the downside obviously is getting together, forming some relationships. You know, the creative process that you get when you've got a whiteboard and no screens and that sort of thing. So you got to figure out the balance. You got to get the rituals right. You got to like read the room all the time and check in with people. But I feel like probably for the rest of my life it's going to be very, very hybrid for me and my teams.

Do you bring people together physically on some cadence?

Yeah, we do. And it's one of those things where we're a little bit overdue, but the sort of momentum that builds up to it is great too. It's like picking the spot and what do we want to do and how much do we want to have it a bit work versus just like hanging out together. And again As a smaller company, I think we've got a lot more flexibility on those sorts of things. But we're able to figure out almost everybody on my team has had a baby in the last year. How do we actually get people off site so that their partners don't murder them for being away? So I, it's, it's an important part of it.

Here you go. I gotta go. It's a business trip.

Somewhere warm and sunny. Sorry.

Yeah, yeah, bye.

Yeah, so that's the, that's the benefit of running a small team. And a lot of our team came with us from the last company. So we've been working together for years as well. And so a lot of the friendships and sort of the foundation has been there for a long time and I think that's just made it really comfortable, like a pretty seamless way of operating for us as a group.

So that little anecdote that you brought up about kind of a lot of the team following you is, brings up kind of where I wanted to go next, which is the relationship between you and Sam. Y Combinator did a study looking back at all of their companies, of which there are many, and found that the single biggest predictor of success was how long the co founders knew each other prior to starting the company. And you guys have a long relationship. I would just love if you could tell us about how that's evolved over time, how you manage that dynamic. I'm curious to unpack the co CEO role as well, but maybe we'll deal with that afterwards. Maybe just talk about that dynamic between the two of you and how it's evolved over time and how you manage it.

I've been really lucky in that I've had close business partnerships with two or three people throughout my career and ones that have cross crossed a couple companies as well. So I had a mentor. He, we started, you know, he was a mentor for me. He joined the company and basically was like popped in above me. And I was very grumpy about the whole thing because I was like one down from the C suite really early on in my career. And I'm like, who's this guy? And he just sat in my office for the first three months and like listened to what I did and how I was running things. And like we became incredibly close friends and colleagues after that because he respected and listened and taught me a whole bunch of stuff I didn't know, but in a way that felt really, really collaborative. So I've been fortunate to have a couple of relationships like that over the Years. And when I first met Sam, he was co running Meta with his sister Amy. Speaking founders that have known each other for a long time. Yeah, seriously, what is that, 15, 20 years? I think by the time they started the company, he was born. And so I saw in both Sam and Amy this understanding of what it really means to trust somebody else and collaborate with them and coming in as their COO and helping them with the stuff that I had a whole bunch of experience which was scaling companies and bringing big things to marketing. The openness from both of them of just like, I'm going to try and absorb, I'm not going to be threatened, I'm not going to say like, wait, that's not your business, you know, that's your lane go. But actually building that trust. And I said to him, I think on day one I'm like, you're not going to trust me, you know, on everything. Day one, I am going to earn your trust. And I know I have to earn your trust in order for you to feel comfortable with me running big parts of the organization that you've built. And we've just sort of iterated on that ever since. So every three months, every quarter, we sit down and we like, how are we leading together? How do you know what's working well, what's not working well? How do I want to stretch my skills and maybe do a little bit more of what you're really good at and vice versa, but that not just trust, but also being able to manage together through times of incredible stress, I think is what leads to a resilient co founder partnership. And I'd have a really hard time starting a company right now without Sam, without a co founder that I trusted that implicitly.

Such an important relationship. Right. It's different now that we're remote, but like certainly back in office times, we spent more time with our co founders than we did with our actual spouse. It's like your business marriage, such an important relationship. And maybe let's talk about the CEO role and then may come back and ask a few more questions. But yeah, it exists, but it's not the norm, it's not the standard. How do you divide the world between you? And just how does the co CEO thing actually work?

It certainly does make certain investors nervous. And I think we both realize that Series B beyond, it's probably not going to be the way that we, you know, we have to run a company, but we know that we're going to co lead kind of no matter what, always. But it's amazing how people are only comfortable with, oh, we need a single throat to choke. Single accountable person. It's like, you got two accountable people. Like, isn't that better anyways? And we never, never have, never will blame each other. Great. So. But I understand that it's a lot of the time it doesn't work. And I've just spoken a few times on, like, the downsides of co CEO relationships and where I've seen them fail through some of the companies I've mentored. For us, it is that constant communication of, like, who's doing what and who's taking the lead on what. Our guiding principle is. Like, the team can never be confused. The team can never. Like, if the team ever came to us and said, we're confused with who should we should go to for what, or we're hearing one thing from Sam, one thing from you, if that's a problem, we will change how we're leading. And luckily that hasn't happened. But we're really careful about that because the purpose is for this to go faster in places where we try not to be in the same room at the same time unless it's absolutely required. So you basically get a CEO in more places at any given point in time. We have certain superpowers that are very distinct from each other, but we've got a Venn diagram of where we overlap a lot. We try and be as interchangeable as possible, and we also make sure that the team and anybody external we're dealing with understands where. That's actually a little bit more of a Sam thing than an EC thing. But I'll understand enough that I can relate it to Sam or loop Sam in, for example, so you're not wasting your time talking to me about it or vice versa.

You divide certain functions between you. Obviously, Sam's very technical. I assume he's driving product, but how does that split work?

Yeah, whenever I answer this question, it always feels more black and white than it actually is. But we try and take advantage on the places where we don't overlap. We try and take advantage of our individual superpowers. So. So product is actually one where we collaborate a lot. Because Sam's superpower is he sees things other people don't see and he can make impossible things happen. And that's often around technology and breakthrough in data. He'll be running experiments at his house with some stuff he's ordered offline and being like, I think this is possible, but nobody's ever done it. Let me try. And a few weeks later, I'll get a report back being like, I think it's possible, or it could be, you know, getting to help write a standard that changes the building industry. Like, I didn't think that was possible. And Sam did it. And that's a Tuesday for Sam.

That's awesome.

And my superpower is, okay, so we think this is a thing that is possible and maybe it's a year away or two years away or something else, and I can just sort of close my eyes and this is how we get there. Right? Here's plan A, B and C. Who we need, who's on the team, what kind of strengths they have, who we need to align externally. How do we explain it to them? Simply, how do we get people? How do we set our goals? Just picturing how we get from A to B. And we collaborate. So on product, for example, Sam's doing all that forward scouting stuff and I care a ton about people's experiences. So it comes from being head of product, like what the user experience is with it. But in this role it's how does the user experience it, how does the buyer experience it? Because that's probably different than the user. How does the team experience? How does a new team member joining Poppy experience their first week of onboarding? I focus on the experience of the customer or the user or something like that. The two of us come together on that. Then of course, our head of product makes it all happen and weighs in and helps guide what we're doing.

The number one quality I look for in CEOs that want to be coached is self awareness. And, you know, another way of looking at that is humility, because that's really what allows you to see the truth, the good, the bad and the ugly. And certainly my observation of both of you, you both, you know, you come from very large companies. Before you had a great success with Meta, you were in this rarefied stratosphere hanging out with Bono. And yet you're very humble and Sam's very humble. And I think that's actually a key part of why this works. I'm curious just given how tight the two of you are as you've started to build out the leadership team, Is it like there's this founder unit and then there's everyone else? Does it end up creating a two tiered leadership team? How do you avoid that?

It's a really good question. And to the self awareness part, the, you know, we have brought in, like, I'm thinking of a senior sales leader who so, so good at what she does. Just like one of the, you know, 30 years of selling enterprise software or being parts of teams that sell enterprise software, she's probably like one of the two best I've ever, I've ever worked with. And I think she was, she was concerned. She was really worried about, you know, am I going to be in the room when you guys are making decisions and talking about things. And, you know, she had very strong opinions on, you know, how are we going to sell and scale. And so it was a lot of deliberate work to make sure because, you know, co founders, we're talking to each other like, you know, dropping the kids off at school and like, oh, we got a call at one and I've got meetings until then. And you've got meetings until then. So we're going to like have 15 minute catch up on what we're doing this today. Oh, and this other thing comes up that we should probably be having this conversation with that sales leader too. But we're just catching up. But we end up making a decision because you got to make decisions really fast. We had to very deliberately make sure that we weren't doing that and that we were, you know, we're a very slack lease culture. We have been forever. I think that's one of the keys for remote working or hybrid teams is that one of the things we do is it's Slack and it's, and it's open Slack channels. And so unless it's like about an HR issue, nobody like DMs just shouldn't exist. It should, should, it should be in an open slack channel. And so though you do have phone conversations like that, rule of thumb is like, as soon as you're done, you, you put it in a Slack channel so everybody can see it. They don't have to read if they don't care. They don't have to subscribe to every channel. Nobody has to read every single thing. But if you're interested in the decisions being made or the conversations happening and you want to weigh in, then you have access to those things. And so those are the kinds of things that again, as co founders who've been working so long together and often can read each other's minds at this point, we very deliberately have to put an effort into so that everybody feels like they're in the tent making the decisions, even when a lot of them happen really fast.

I have mixed feelings about Slack culture. I know why you do it and you're promoting transparency and also asynchronous collaboration. What I find is that people address each other Differently when they're just banging out on a keyboard versus actually interacting. And then of course, often it's faster. There's this giant thread going back and forth and like, let's just get on a zoom and bang it out. And one thing that's fascinating, I had Aydin, the CEO of Fellow, on this podcast a few episodes ago. And their mission is to make meetings suck less.

I saw that.

Yeah. And yeah, I'd love to thank somebody.

For taking on that mission.

It's a daunting task ahead of them. But the way he described to me, like, every meeting, if you use Fellow in your company, every meeting is a podcast. So you can go back afterwards and listen to it. You can listen to it at 3x speed while you're like on the treadmill. So just another interesting, maybe more high fidelity way to create the transparency that, that you're. You're going after here.

I, I love that idea. And, and for us, you know, if it's an internal meeting, 99 of the time, again, it's recorded and so people can listen. But I like the idea of, you know, the 3x speed and the, you know, we do a lot of looms, but looms are meant to be short and they're less. It's not about decision making. It's more like one person conveying information. Exactly.

A little update.

But I think all of those are tools in the tool belt that you should always be, you know, looking at and figuring out the culture you want for your organization, how you want your team to run. Given that, I think, you know, again, for a lot of tech companies, hybrid or tech companies our size, anyways, hybrid is going to be the way it is for a long, long time. You can't sit stagnant on it and be like, oh, we'll just have a, I don't know, like a slack huddle. And that's good enough. I'm fascinated. Even a former business partner of mine, Ryan Dochak, he had a. We started a company together. We were way too early. First go out of, out of the gate and did not go anywhere. Then he started a company called Tunnel Bear, sold that to McAfee.

Oh, I remember that. Wow, I haven't heard that name in a long time.

And since, you know, that acquisition was completed, et cetera, he started again with a lot of the original folks, a company called, with a product called Throw that just got released. And it's basically a way. I've always amazed at the company culture he's able to build in his companies and It's a plugin, and it basically lets you throw things at people on your team. And it's a lot more than that, but it's sort of like how you would act if you were actually physically in the space together. Right. And if you were in a goofy, fun loving culture of people, it's like, I'm going to like, send you the CEO, like an award for, you know, most wordiness in a meeting and, you know, as somebody's presenting or something like that. So I love the fact that there's innovation around these kind of tools that. That can bring us together more and reinforce it.

You were probably doing a bunch of these things already because you and Sam had such a tight collaboration. But this is your first time officially in the CEO chair, and I'm wondering what was the biggest challenge? Is it the same, is it different? And if it was different, how have you prepared yourself?

Yeah, I definitely think there's been a couple of differences. I think a lot of the folks, a lot of your listeners are probably going to have done the same thing, which is as you go through your career in different organizations and working with different people, you're making lists, you're making lists of, oh, that seems to work. I see where they made that decision. I don't know if I would have made that decision. I like the way that manager handled that situ. You're sort of keeping track of like, hey, if I ever get to do this one day, I'm gonna learn from this situation of this person. And so I've been, you know, sort of lining those up. And I came to entrepreneurship later than a lot of folks, and. And so I had a lot of backlog and then co leading with Sam, even though technically CEO, CEO relationship, we were both taking notes of, like, hey, if we could do this all over again, what would we do differently? What would you do the same? And so that was a lot of the conversation when we started the company back in. I think the. For me specifically moving from COO to CEO is I had to be more comfortable with mess. And that was. That still is uncomfortable for me. And Sam knows it's uncomfortable for me, and I know I'm uncomfortable with it and I got to deal with it, but a lot of the times, at least the way I approach COO roles and I think a lot of people do, is the CEO has an idea or a goal or something, and you've got to take that mess, that thing that's going to disrupt the business or whatever, and you've got to figure out how to make it work. And so you're, you're not cleaning up the messes. That's maybe the wrong phrase, but you're like creating, organizing the chaos, some of that. And, and if I had organized all the chaos and we were achieving the goals we set out, then I've done my job as the COO and people were happy and we're hitting our goals. And as CEO, it behooves me to make mess now. It behooves me to bring things into the company that are very uncomfortable and we don't know how to do yet. And I don't know if my team's up for. And God, if we change one more thing, the whole thing might fall apart. But it's the right thing to do for the business. And so I have to be comfortable with making this. And Sam helps coach me through that because again, he's so fixated on this is an impossible thing that is possible now. And so that's a great way that we complement each other on what we're comfortable with and what we're not comfortable with.

I love that. I can imagine as a former CEO whose job was to bring order to chaos, that mess would be troubling for you. But I equate mess with speed, which I think is the primary strategy and primary tactic for a venture backed startup. Right. All else being equal, getting to the same place faster tends to be more valuable. And so if you're tidying up every little thing and putting out every little fire along the way, you're just going to go slow.

Oh yeah, I entirely agree with that. And that is perfection has never been the goal for me. But, but making it so that your team, their tolerance level of risk taking and doing something new is typically a little bit less than yours as a founder. Right. Like you're, you're in this, you know, you've got a different reward structure, et cetera. But I, as in a CEO role, I would be spending a lot of time being like, what, what can this team do? What, you know, what, who do we need to add into the team? What part of this that this person can handle? And it's going to be growth for them, but they can do. And now as a CEO, sometimes I just have to forget that and be like, we'll figure it out. We're just going to create a mess and figure it out.

So as we start to wind down, I want to go back to your prior experience, you know, being inside some big companies, Microsoft, Hummingbird, etc. And I've personally had a mixed track record hiring people out of really big companies because their definition of operating is different. Like their definition of operating is, well, I'm going to hire a bunch of people and I'm going to delegate really well and going to get stuff done. And you've made that transition. I'm just wondering what are the really, for anyone who's thinking about hiring leaders from big companies, you know, what are, what, what is the magic that comes from that, that you took with you and what is like the stuff that we really need to get rid of so that these leaders can succeed inside a more kind of startup environment?

It's, it's an, it's an amazing question because it is really a trade off that I think when you're from a larger company and you're interviewing with a smaller company, you might not realize how much your interviewers like with everything you say, trying to figure out if you can make it like in the new world. Right. And I, I feel like I've benefited from experience because not only have we brought corporate folks into smaller environments, but we've also done a lot of work bringing academics out of academia and into or like researchers into, you know, the four.

That's not for the faint of heart.

And then we've learned a lot. So I think that list of like, what do you do, how do you vet, you know, and prep somebody for how much of a shift it's going to be? You know, I've got one list for academics that I've got one list for folks in corporate. But the, in corporate, there's so much you have to, there's so much you have to shed, right? There's a lot of people I work with at Microsoft, I don't know, 15 years ago now who are still at Microsoft and they've never changed companies. And you call them lifers, they live wonderful lives, they're very happy people. But I have a really hard time. Like you have to give up the reward system that you have literally based your life around, right? In academia as an example or being a researcher, you are rewarded for discovering something nobody else has discovered before. And it could be a tiny, tiny little thing, but you get to write a paper on it and hopefully get it in a good journal. And that leads you one step closer to tenure. You're always finding that one little thing that's new, where the business we're all in is having something that works and figuring out how to scale it. Not always looking for a net new thing that may or may not be actually Valuable to a customer. And in corporate, it's a lot about what I find. It's about what people are used to being rewarded for and how fluid job descriptions can be and how egoless. On good days, a good startup team job responsibilities are incredibly clued in. People's, you know, where people would say their toes are being stepped on. Like, it's not, it's not a problem. There's enough work for everybody. Right? It's not about titles. It's not, it's not, you know, this is my lane. That's your lane. It's like it's all hands on deck almost all the time. And so if you're a person, like, no, that's my lane, you know, because you're thinking that's what you're going to get your performance review about, you know, 11 months from now, that, that's the kind of mind shift you gotta, you gotta get people out of. And so that, you know, living a little bit in chaos, but also just not having an ego about what, what you do versus other people do, I think are some of the, some of the two, yeah, the two biggest tickets we look at when we're trying to help somebody make a transition coming out.

Of those big companies. I don't know what's the right way to say this. Did you have to like depoliticize yourself? Like just turn down like the, the force fields and the protection mechanisms and the territorialness? Was that a thing?

I, I, I think that's one of the reasons why I only did corporate for the first 10 years of my life. And, and because it's a long time, actually, it's, it's a long time. Started in consulting, which was fascinating because I got exposure to all sorts of different kinds of businesses, you know, almost all over the world and how they ran. And again, on my list, I'm like never working for a company. I'm never doing this, never doing that, because I had to for, you know, six months or so in a lot of cases. And then being head of product, where I took that role seriously, regardless of the company I was at and where I did well was where I had the political clout or the blessing from above that I could get my fingers in other departments in order to make the product better. And so one of the organizations I worked for, hired as a first head of product, first product manager, had a product, built a product management team, designers, et cetera, but realized I could fix product, but what I really needed to do was help fix the R and D process and Then once that was fixed, I really had to fix support because they weren't supporting the product very well. And then it's like we're not really explaining the product well. So I'm going to have to go into marketing and say like at least product marketing, can I help fix that?

Sounds like you were a CEO. You were a CEO in training.

Yeah. And that, that actually I think is what, what, what worked. And a lot of organizations, you know, I wouldn't have been allowed to do any of that, but I was lucky that the, the organizations I had picked there, like, yeah, if that's what it's going to take to help us sell the product because we're a product based company, then let's go do it.

Yeah. I've often felt that the best product leaders are mini CEOs, so maybe final question. You have all this diversity of experience. You were a consultant, so you can take anything and put it on a two by two matrix. You've been in the big companies, you've been in the startups. Looking back, what advice would you give to your younger self? You know what, digest all the lessons into like, I don't know, a couple of nuggets.

I think what I would. Two things. One is having these different points of view has been incredibly helpful. So I remember after Ryan and I, so the consulting gave me exposure to a bunch of different things. Being head of product gave me exposure to not just product stuff but a whole bunch of other departments and, and how product based companies run. And then after Ryan and I failed at our first company together, I'm like, what I realize I don't know anything about is fundraising and I don't know anything about VC. And so I actually started my PhD program on and my primary thesis was around do accelerators actually accelerate? And so I started interviewing accelerators and getting involved in them. And then I worked for a very early Canadian vc, early stage Canadian VC back in a long time ago too. Because I'm like, I need to know how they make decisions. So I'm going to actually spend six to nine months in their organization before I go try and start something else. Now a whole bunch of that information can be found online and through podcasts, etc, so maybe that was like more time investment than people are willing to make now. But just realizing the points of view I don't understand. So having been in big companies helps me so much now because I sell to big companies and so I know how their decision making works and how much it's about. It's really Easy for people to say no and it's really hard for them to say yes and all that kind of stuff that has benefited me tremendously. And then the second thing I think is less about any given role or any given company. But I should have been more blunt. I should have been worried with people all the way through. And I think back on the amount of time I have wasted of just not saying exactly how I felt or how I thought and just in a non emotional way, but just not having people guess right and how much more quickly things could have moved if I wasn't trying to be polite or not step on somebody's toes or not get somebody in trouble or whatever it was. I think that sort of clarity of communication and preciseness and what you call bluntness is something that I wish I had been more comfortable with early on in my career. Gender, maybe nationality, maybe all of those things make it a little bit. I feel like it made it a little bit harder for me to get to where I am today. And it's still not perfect, but I.

See that, you know, pattern recognition, I think, yeah, gender is a role, plays a role also. Just age, you know, younger we're insecure and older we're like, this is it. I. I'm totally comfortable in my own skin. I've got experience and you just need to hear the truth.

The number of times maybe you do, but I have in my head, it's like, life's too short. I'm just gonna say it.

Yeah, yeah, yeah. And this goes back to speed, right? Being direct promotes speed, which is everything for a startup.

Yeah, exactly. Right.

Well, Elizabeth, thank you so much. This has been a really great conversation and really great to see you again. Thank you so much for making the time.

Thanks, Mark. It was a pleasure to be here.

Hey, thanks for listening to the Startup CEO Show. If you'd like to connect with me, be sure to visit my website at Markmcloud me or follow me on LinkedIn @the Mark McLeod or Twitter @Mark McLeod underscore. And if you want to tune in again next week, be sure to subscribe on YouTube, Spotify, Apple, or wherever you get your podcasts. We'll see you next time.