Friend Your Funders First | Caren Maio at Funnel

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Caren Maio 00:00
We spent a lot of time with a core group of early customers, we shadowed them. We spoke to them as frequently as we could, and really try to understand what their pain points were. And help them solve for them.

Alexander Ferguson 00:19
Caren, I’m excited to continue our conversation now and hear your journey. As a tech leader, I’m sure there’s been the highs and lows. To begin, tell me your story. Like how did you get to where you are today?

Caren Maio 00:33
Gosh, the peaks and valleys the roller coaster of entrepreneurship. Yeah, so it’s, it’s been a wild ride. I’ve loved every second of it. Even the lows, you know, when you recognize them for what they are, and know that the you know, that the high will follow. It’s just been it’s been a journey for sure. I got into this industry. And it’s interesting, because when I think about Prop tech, that word didn’t even exist when when we started building, building our or software. But I was a frustrated apartment Hunter, right. So like I had experienced the pain of moving again and again. And I was insanely frustrated by it. And I felt like there had to be a better way, right? You hear entrepreneurs talk about that all the time, there has to be a better way. I felt that. And I very much wanted to scratch my own itch because I felt this pain. And I also had this, I don’t know, just this deep curiosity and interest in real estate. Whenever a friend would say that they were looking for new apartment, I was that weirdo that would raise your hand and say I’ll help you. And people would be like, Why this process sucks. But I was just so intrigued by it and fascinated by it. So that’s that’s how I initially started. But again, did not have real estate experience. I didn’t even really have Tech experience, I didn’t have Tech experience my co founder dead, which was why I felt like we would be a great fit. So he started building the tech and I kind of did everything else initially,

Alexander Ferguson 02:01
your background was different in marketing and sales. And so that’s what you knew well, and then probably selling

Caren Maio 02:07
myself short. It wasn’t like I didn’t know how to do anything. Yes, my background was in marketing and sales, but it certainly wasn’t in certainly wasn’t in real estate.

Alexander Ferguson 02:14
Mm hmm. So a lot a lot of learnings to get that initial beginning part finding maybe your your CTO, your co founder and talk to me like what did it take to get the initial funding and kind of get off the ground and get started any tactics that that you used, maybe another entrepreneur learn from?

Caren Maio 02:32
For sure. Yeah, so um, I’ll caveat this by saying we did have what I believe was a big leg up because Mike and I, we were we were part of an accelerator program called TechStars, which many folks might be aware of, they were making their way from Boulder to New York City to launch their first cohort. So that was almost like an I mean, that was an acceleration, just even in relationship building, which is really what I wanted to use it for. I wanted to kind of introduce ourselves to that sort of New York City tech ecosystem, which at that point, was just starting to percolate. So that’s really how I how I viewed TechStars. For us, we needed to figure out obviously what we were building. But I also wanted to just meet like minded individuals and see who we kind of gelled with. So it was massively successful for us in that regard. We were able to secure mentors as part of that program. And many of those mentors ended up becoming our early stage investors, as well as advisors to the business. My biggest takeaway from that, which I always try to convey to any any early stage entrepreneur, I, I speak to his date before you get married. It’s true in all aspects of life, right? But use the opportunity, you know, if you approach an investor, whether it’s a VC or an angel, whoever they may be, and you say, Hi, my name is so and so nice to meet you. I’m raising money, you’ve done something wrong. As a founder, you should always be building relationships, and particularly relationships well in advance, right. So this is something that I try to do with hiring something I try to do with investors. It’s building relationships before the actual transaction happens, right? Particularly in the case of fundraising, right, this is this is ideally, someone who’s going to be with you, right for the long haul. And this is going to be a very important relationship, and you’re going to have great conversations and you’re going to have tough conversations, and there’s going to be hard decisions that need to be made. So you need to know who you’re dealing with on the other end, right. It’s as much of an interview or dating process for you as a founder, as it is for the investor.

Alexander Ferguson 04:41
You have your funding, you kind of get started, you’ve done the dating, and now you get married to that and then you’re moving forward getting the first few customers and clients using a service. That’s that’s also initial thing to make that happen. Any tactics that that work for you that you can share.

Caren Maio 04:58
Sure, yeah, I mean, I’ll say I’ll state that it’s it’s a hustle, right? A lot of blood, sweat and tears went into it. And particularly for us, right? We, when we were starting out and starting to have conversations with owners and fee managers in New York City, I mean, New York City. It’s a tough racket, right? It’s I mean, the New York City Real Estate community, it’s very close knit. And we didn’t come from that world, right. So we were sort of outsiders trying to get in. And I think we did a great job with that. And I and I think the reason why was because we we, first of all, we were empathetic, right, we listened, we didn’t try to tell people, what we thought their problems were, we spent a lot of time with a core group of early customers, we shadowed them. We spoke to them as frequently as we could, and really try to understand what their pain points were, and help them solve for that. Right. And, you know, I’d say, you know, in working in that way, and frankly, providing that great experience early on, we also leveraged those folks and said, Hey, listen, you know, if you have other folks in your network, who you think would benefit from this, or who you think we should be speaking to, please introduce us, we made it very easy for those introductions to happen, whether it was forwardable emails or anything else. But for every interaction I had with an owner, I tried to get for five, you know, five more introductions, right? And really expand our network that way.

Alexander Ferguson 06:21
being conscientious and purpose purposeful in getting more referrals after each relationship five, that’s That’s powerful. Shoot for the stars and get one too, it’s more than you would have if you weren’t trying. You also was a pivot from customer to then b2b focused. And I think it’s natural for every business as you’re starting out to continually evolve, get where, how are we solving this problem? The route problem improving the the the leasing experience hasn’t changed. But talk to me, how did they come to that realization? How do you make that shift? Sure.

Caren Maio 06:57
Yeah. That’s a great question. So two years in, so this was after TechStars, we had raised a little bit of friends and family money. We were I mean, like, again, listening, right? So we started talking to we initially built a b2c product. It was renter facings, it would help renters kind of clip or bookmark listings that they found everywhere, organize it, and ideally make a better decision on where to live faster. So we did that we were building that. And we learned from users where it was like, hey, this information I’m clipping from all these sites, it’s wrong. It’s inaccurate, the apartment was rented weeks ago, I’m having all of this pain. Can you solve for that? So that was sort of like that moment where we’re like, we can’t solve for that based on the current iteration of the product or what we’re building. But let’s find out why that exists. Then we went to sort of the the other side, right, the businesses and we said, hey, we’re getting a lot of complaints about X y&z How are you running this process now? And after a series of conversations, and hearing well, I use spreadsheets and people are I use accounting software, and people are I use 10 different systems and people. That was the lightbulb moment where we said, this has been solved for in other in other industries, it will be solved for. It’s just a matter of when and we felt like we were equipped to solve that problem. So that’s how we pivoted from b2c to b2b. Say, Okay, well, let’s deliver technology to these folks. Because it’s not that they don’t want to provide a great apartment leasing experience, it’s that they don’t have the technology to do so. So let’s build that technology for them.

Alexander Ferguson 08:35
After you’ve made the shift, and you realize are this is a problem, and we can solve this because it’s going to be solved. Scaling. How do you go from just a few clients, few customers on it, and then to, to, you know, 10s, hundreds and more. What tactics have you found that have worked?

Caren Maio 08:53
It’s a great question. Yeah. So I’d say you know, that’s, that’s a tale as old as time as far as challenges go, right. I think focus is something that we probably didn’t do all that well. And that’s on me right in the beginning, because he you want to try to figure out where where you had that fit. And then I think as we as we’ve grown, and as we’ve matured as an organ as an as an organization, right? We’ve learned where that where that kind of sweet spot was, right. So when you ask me, right, like the right type of customer, we are focused on a very particular type of customer, particular unit size. And we’ve been able to, to really kind of whittle that down to understand, okay, who is the right customer for us? And then how do we approach them and how do we sell into them? How do we have those conversations that took time? Right, to really figure out it was a lot of pardon my French throwing shit against the wall and trying to figure out what what would stick right. But once you figure that out, having that laser focus and being very surgical, is very, very important. And I think we’ve we’ve figured that out over time, right and not trying to be all things to all people and getting comfortable saying no, when it’s not the right fit.

Alexander Ferguson 10:06
You know, your target audience and you said, there’s a sweet spot that you can you work within? How do you get in front of those folks? Is it? Is it simple just calling them emailing them? Do you do a lot of your own Pay Per Click ads? Like how do you get in front of someone and say, You I have your solution? You just don’t realize? I haven’t?

Caren Maio 10:24
Yeah, yeah. Well, so I think, you know, certainly marketing for any company, there should be a lot of testing going on, right? There should be a lot of iteration around it around what works trying to figure out okay, now that you know who your customer segment is, where do they hang out? What did they read? Right? Trying to kind of reverse engineer Okay, now, now who I know who I’m going after, what’s the best way to get their attention? Right. For us, we use a combination of, Well, historically, it was always conferences, events, We’ve obviously had to pivot around that and start to layer in other things like digital marketing. But it’s just it’s, you know, again, it comes down to listening, trying to understand, Okay, now that I know who my customer is, how do I reverse engineer that and figure out kind of what they’re reading, where they’re hanging out who they’re talking to, and make sure that we get our name and our product? Top of Mind.

Alexander Ferguson 11:13
You make an excellent point that there are often conferences and events. And that’s a lot of folks that they were it was a great place to do it. Get in front of them, you see them. And now that’s shifting now, though, do you feel it’ll eventually come back to that that you able to do those same things again? Or is it going to be just a new normal of how you reach and be able to scale your conversations? And that’s a

Caren Maio 11:33
great question. I think that’s the multimillion probably multi billion dollar question everyone’s trying to answer is this. Is this it? Is this how we operate now? Or is there is there? Are we going back to the to the to the old way of doing things? I think it’s probably going to be a hybrid, I think there will be a new normal. I don’t know if this is necessarily our new normal today. I hope it’s not I think we’ll be evolving into something beyond that. I don’t think though, it’s going to be going back to the way things were done before. I think we’re going to be said that I mean, that would be taking a step back, I think that there’s a lot that there are a lot of lessons to be learned from the year we’ve had. And I think the silver lining would be I mean, I think it would be all for naught, right? If we just reverted back to our old ways and didn’t learn a thing. I think we should be intellectually curious, I think we should be looking to move forward and take the best of what was done before and try to improve upon it. So as it relates to events, I don’t know exactly what that means. I think either there’s no substitute for that in person interaction. Will every event need to be in person every interaction need to be in person? I don’t think so.

Alexander Ferguson 12:47
I like your perspective, that it’ll be a new normal. So everyone is saying that, but it’s it’s still somewhat, it’s still true of combination of what was and yet what will be. But it’s knowing what you’ve learned from already coming up to this point that you can, I guess, apply going forward, your growth is exciting to see over the past several years and be able to sounds like there’s momentum, you know, you said that road trip that you made in 2019. And going into this year, the efforts are to pay off. If you had to say one thing you’re most excited about going in 2021? What would you say that is?

Caren Maio 13:24
So I’m very interested to see the growth, the change the innovation, and maybe that will be companies products, just whatever that may be, that will that will come as a result of of the of the really tough, just wild, unprecedented year, we’ve had, I do think that there will be some silver linings from it, and I’m excited to experience them and and and see what they are

Alexander Ferguson 13:51
as the leader and to to bring the whole team forward that has its own challenges that come with it. How have you kept the culture thriving and strong? And the team growing any lessons learned there of being able to grow the team and keep the culture strong?

Caren Maio 14:12
Yeah, well, so as as one of the founders of this company, I think we’ve we’ve had to kind of iterate on our communication style and what works for three people won’t work for 30 and won’t work for you know, you know, as you grow, but I think the one thing that’s always remain true, is we are a transparent group of people. And we over communicate. And I think that in a period of time where there’s a lot of anxiety and fear, which is natural, over communicating is the best antidote for for that anxiety is what I’ve experienced. And you know, fortunately we have a great group of leaders and just a great group of people within the company like you know, the the folks who the folks who we have on the roundtable there meeting and they all have that same level of commitment to transparency and being straightforward and communicating as early and as often as we can. With everyone on the team, which is great.

Alexander Ferguson 15:13
Our communication and transparency makes comfortable, more comfortable workplace, more trusting workforce, how big is your team? No.

Caren Maio 15:22
So our team is a little over 40, although we are in a period of hiring very, very actively, so that will be a much, much higher number in the next few weeks.

Alexander Ferguson 15:34
That’s it. That’s exciting. If anything, that’s the foundation that you set, though, as you grow, that every new leader that as you’re hiring, and has to manage people, that same mentality stays with.

Caren Maio 15:44
Exactly, exactly. That’s why I think having a really core group of just just being very clear about about who you are the culture, you want to build the values that are important to you, I think that’s so important, because that sets that foundation as you as you grow, where you’re able to really understand, okay, are these the right folks we’re bringing on board? And really making sure that that culture stays strong, right, I think it’s important to have a strong culture, whatever you’re building, because I think it’s very important for those folks to self select into it, and really be bought in.

Alexander Ferguson 16:19
Where have you gone to learn and grow and innovate. So any books, or podcasts or audiobooks that you can recommend or pop into your head of I get it. I’ve really enjoyed this one. This is where I get I’ve gotten insight, anything you can share. Yeah, so

Caren Maio 16:35
I’m a big one of my favorite books is the hard thing about hard things. It’s just like it’s table stakes for me, like whenever anyone new starts in the organization, I’m always like, please, please, please read that book. There’s also a really great book called Positive Intelligence that talks about how often your mind works for you versus against you. And probably no shocker there it more often than not works against you, and talking about things that you can do to really get your mind working with you. So those are probably two of my favorite books. And the ones that I recommend other founders team members read whenever, whenever I get a chance to talk to anyone about about about books.

Alexander Ferguson 17:19
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