Matthew Kligerman on Raising $50 Million To Build A Conversion Platform and AI Sales Agents In Brazil

Matthew Kligerman’s path as a founder is a masterclass in vision, adaptability, and persistence. His entrepreneurial story is woven with bold moves, serendipitous moments, and relentless curiosity.

In this engrossing interview, Matthew talks about adapting his experiences as a climber into building, scaling, and financing his companies. He also reveals unique aspects of the adventure of building a company in Latin America.

Matthew’s company, Escale, has attracted funding from top-tier investors like Invus, QED Investors, Redpoint Eventures, and Kaszek.

In this episode, you will learn:

• Matthew Kligerman’s journey began with childhood ventures that taught him ingenuity and determination.
• During his college years, he leveraged an accidental discovery about SEO to build Legacy Links, a highly profitable .edu backlink marketplace.
• Experiencing inefficiencies in Brazil’s customer acquisition processes inspired Matthew to co-found Escale, a company transforming conversion funnels.
• Escale’s AI sales agents outperform human counterparts by 30% on platforms like WhatsApp, revolutionizing sales conversions.
• Matthew and his co-founders started with limited resources but scaled Escale with strategic partnerships and funding rounds.
• Matthew applied insights from his mountain climbing experiences, such as trust, adaptability, and teamwork, to entrepreneurship.
• After stepping back from Escale, Matthew plans to bring generative AI-driven customer engagement innovations to the U.S. market.

 

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About Matthew Kligerman:

Matthew Kligerman, based in Charlotte, NC, US, works at Growth stage companies. Matthew Kligerman brings experience from previous roles at ESCALE, Endeavor, and Citigroup.

Matthew Kligerman holds a 2005 – 2009 Ciências e Engenharia in Engenharia Mecânica e Ciência dos Materiais; Mercados e Estudos de Gestão @ Duke University. With a robust skill set that includes Entrepreneurship, Venture Capital, SEO, SEM, Customer Acquisition and more.

Connect with Matthew Kligerman:

• LinkedIn
• TheOrg
• Crunchbase
• RocketReach

Read the Full Transcription of the Interview:

Alejandro Cremades: All right. Hello, everyone, and welcome to the Deal Maker Show. So do today we have a really amazing guest. you know I guess that again, you know he’s done it, you know building, scaling, financing, and also so partially exited too. We’re going to be talking about secondary you know type of transactions. But again, you know we’re going to be talking about all the good stuff. I mean, in his case also, he’s a climber, so we’re going to be able to identify Some similarities you know around sleeping you know in vertical type of vi environments for for many days and how you perhaps you know learn stuff around business, partnerships. ah Again, he’s built stuff in Latin America. So I think that it’s definitely a different way of doing business you know compared to the US. But again, a lot to learn. So brace yourself for a very inspiring conversation. And without further ado, let’s welcome our guest today, Matthew Kligerman. Welcome to the show.

Matthew Kligerman: Thank you Alejandro. It’s great to be here, listen to your show a lot through my entrepreneurial journeys and it’s really nice to now be here with you.

Alejandro Cremades: Thank you so much, Matthew. So originally born in Florida. So give us a walk through memory e lane. How is life growing up for you?

Matthew Kligerman: It was really nice growing up there. I had, we grew up in a pretty normal upper middle class neighborhood and family. I had two great loving parents. um Both of them have a lot of entrepreneurial spirit and definitely gave a lot of it to me.

Matthew Kligerman: They were working professionals, but each had their own offices that they had built up from scratch. And yeah, it’s funny, a lot of my childhood in South Florida is peppered with door to door sales around the neighborhood that I lived in. ah You know, it’s funny, I think a lot of my later on business lessons ah grew out of some of these crazy childhood businesses and sales, I would just go around selling you know, for fundraisers, save the Amazon t-shirts, knock around all the doors of the neighborhood, or and remember my parents taking us to Costco to go buy big packs of muffins and drinks to sell on hot days at the swap shop, this flea market nearby, or rolling around toys in my little wagon and selling toys to kids around the neighborhood as a kid. ah And

Matthew Kligerman: ah When i I spent all my summers growing up in Asheville, North Carolina, my granddad built a summer camp there and as a kid spent all my summers there just playing around having a blast and then ended up working just many different jobs at that camp from counselor to coordinating counselors to running a rock climbing program at the camp and You know, it’s funny, and as a kid, I just loved the camp for what it was. And as I’ve grown older, I look back on that a lot and what my grandfather built and seeing, you know, a thousand kids go through there every summer and all the memories that are formed for kids, the new experiences they have that push them outside their comfort zone. And more and more, I see this as a legacy that my grandfather built. He’s passed now, a legacy he’s built that’s really inspired me for

Matthew Kligerman: the companies that I’ve built to not just make money and be good businesses, but to have amazing impact for the people who are involved in them and create amazing experiences that help for their growth and create memories and journeys and friendships for each of them too.

Alejandro Cremades: So in your case, you know you ended up in getting into engineering. So that whole, obviously, you know seeing you know your family you know doing business and what you experienced too, you know I’m sure that that gave you kind of like ah you know some type of um perspective or approach into problem solving, let’s say, in business. But I guess problem solving as a whole and and then also engineering, what really sparked your interest to go in that direction?

Matthew Kligerman: Yeah, I’d say engineering. i studied I studied mechanical engineering. And I’d say that’s actually because I had this crazy physics professor in high school. He was this Cuban guy, Mr. Archibiletta. He was this Cuban guy.

Matthew Kligerman: who had studied nuclear physics in Cuba and had built a raft and sailed over to South Florida, got got onto land, and soon thereafter became my high school physics professor. It was way overqualified to be our professor, and he was incredible. And I think you know just discovering the mysteries of the universe and how things worked was incredible with him. And that definitely pushed me into engineering.

Matthew Kligerman: as well as a general affinity for math and sciences. my ah And then last, I’d say I’ve loved rock climbing ever since probably I was 16, I got into it. And um there are certain devices in rock climbing that the physics of how they work to to basically stick into the rock to support a falling climber is really interesting. They’re actually really interesting. Engineering marvel is how they were built. And I was pretty obsessed with the engineering behind them. And so those factors all made me want to go dive into the engineering world and take to that coming out of high school.

Alejandro Cremades: so In your case, you know obviously after do um you even even in Duke, you know you had the um the entrepreneurial you know kind of like bug, and and and you got started with legacy links. so what What happened with legacy links?

Matthew Kligerman: Yeah. Yeah. It’s funny to think about legacy links, you know, I wouldn’t even call it an entrepreneurial bug or a business at that point. you know It was really just this crazy little side hustle. ah when i was so When I was at Duke, i I was running the Outdoors Club there. and ah i was beyond I was the president of the Outdoors Club, but I was also the webmaster of the Outdoors Club website. ah This is at a time when the term webmaster still existed.

Matthew Kligerman: ah and i would I would just update HTML and stuff on the site, but one day I got an email from someone, some some weird marketing company, asking me if I could put a link onto our website and if they would pay the club $10 per month if I put this link on the site. and I thought about that. I said, wow, $10 a month.

Matthew Kligerman: that’s to me, you know, 120 bucks a year for this link that that sound like the jackpot that that was big money back then it seemed great. yeah We could buy a whole other climbing room for the club. Amazing. Put the link on and kept adding more that this company would give me and other companies started reaching out to oddly enough. I think we had 20 links on the website, we’re generating like 2400 bucks a year.

Matthew Kligerman: you know For me, this was huge money. we could you know find I think we bought a trip to Peru for finance, part of the trip to Peru with with a lot of this funds. But suddenly never something like didn’t quite make sense to me about this. you know why Why would these random companies like a LASIK eye surgeon in Colorado be wanting to advertise on the Duke Outdoors Club website? ah there’s there’s really no There’s no traffic that’s going to get to them from this.

Matthew Kligerman: And I looked into it in these companies and found out they were search engine optimization companies. There were companies that were basically helping their clients get to the top of Google. And I researched more into this and found out that the way Google’s algorithm worked, this is back in 2005, the way it was working was they Google had built out this custom link graph algorithm to be able to understand what how other websites and the internet are linking to one another. And essentially a when high quality websites link to another website, that shows ah so an authority ah ah into the graph for Google’s link graph and helps that website receiving those high quality links to rank higher. ah But then what was really interesting is I saw how much these SEO companies were charging their clients for those same links they were putting on my site

Matthew Kligerman: And I saw they were charging their clients 200 bucks a month. And you know all of a sudden, that $10 a month, it seemed like you know the jackpot, I just couldn’t, $200 a month just seemed you know and totally totally surreal. So I reached back out to those those SEO companies and asked them if they needed more links for their clients. And they told me they couldn’t get enough. If I got them sites, they would fill them up with links.

Matthew Kligerman: And we cut a deal to basically split it 50-50, more or less, I think, or or I’d get 50 to 100 bucks per link. And I reached out to all my best friends who had just graduated from high school, and then were at universities all over the states, ah and basically asked them to recruit websites at their universities for me. And I would pay each of them 10 bucks a month, each of the clubs that they recruited 10 bucks a month per link. I paid them not 10 bucks a month, I paid them $10 a month per link they got.

Matthew Kligerman: um And overnight, they all went after it, recruited a bunch of sites, and I built essentially the largest dot .edu ah marketplace in the world at that point in time.

Matthew Kligerman: ah um I didn’t realize this was very black hat SEO black hat SEO is you know, this is like the hacker side of SEO This is not following by Google’s rules at all. It’s definitely cheating their algorithm at the time it worked I didn’t realize I didn’t realize that It was this black hat side of things but it was really really effective and people paid good money to get a link on Stanford’s website or Princeton’s website um so that That business actually started growing quite a bit through so through school. We probably had about 30 people or so working for the company part-time throughout the country. ah and that Although we started off with this, you know at the time I didn’t really know what to call it, now I would call it more of a managed marketplace. ah and We ended up building on top of this because we saw how effective these links were to

Matthew Kligerman: the sites that we would that we would um link to, we actually ended up building out our own agency to then provide SEO services to customers and to provide much more of the services ah beyond just the link building side. And then we actually evolved that into building out our own lead generation web properties.

Matthew Kligerman: where we would build our own web properties, would use the links to then drive those properties to the top of Google very quickly for value value valuable search terms, such as car insurance, get leads, and then sell those leads to others in the market. ah And this you know at the time, honestly, I kind of thought this was a fun little side hustle. I didn’t really think much of it. It ended up teaching me a ton about digital marketing.

Matthew Kligerman: and ah Yeah, it led a lot to what happened later on in my life.

Alejandro Cremades: So in your life, i mean obviously you you ended up um you know coming out of basically the this experience, right? and And instead of like keep going at it, you decide to go into corporate America.

Alejandro Cremades: So so how did that happen?

Matthew Kligerman: Yeah. Yeah, I guess I didn’t really see this business as even a real business back then, even though when I look back on it, it was actually a really lucrative, great business. um I think I just felt i it would be helpful. And honestly, I’m not sure if this was right. But at the time, I thought it would be really helpful to go get a job in a real company to actually get real skills and learn. I didn’t really consider what I was doing real skills back then for some reason. They were probably the most real ones, though.

Matthew Kligerman: ah So yeah, when I when I graduated Duke, I ended up going to I was I was graduating in 2009. And basically, it was like just after you know, the 2008 market crash, probably the worst time to go into the job market. I really just would get any you know, was it was happy with any job I could possibly get in the finance space and in Wall Street.

Matthew Kligerman: I ended up getting a job working for Citi with an amazing boss, and I actually got quite lucky. I joined a job. It was not one of those typical investment banking or a typical trading desk. was was actually I was actually on a product team building out services and technology for fund managers to use to better manage their investment funds and firms.

Matthew Kligerman: which was actually really lucky. He was actually basically building a business with the bank. And so I did that. ah ah the The business I built in college, Legacy Links, I kept doing this as a side hustle. So I would be working at my desk, and then I have a client with an urgent request, and I would you know step into the bathroom to send some messages on my BlackBerry back then, or or so or step to the corner of the office and like do a kind of hidden phone call with a customer.

Matthew Kligerman: ah And that that i was juggling these two things. And honestly, there was a lot of learnings from each from each one that helped the other was actually quite complimentary. And eventually, legacy links that business that I was running at the same time, we started actually breaking in into the VC and PE world out of New York, actually. And we started working with the portfolio companies of a handful of VC and PE investors.

Matthew Kligerman: We were doing really high quality work. We evolved a lot from that black hat strategy into more know quality long-term strategies. And I really, honestly, that was one of the most helpful experiences for me was working into that space. Because they for the first time, I got to see what incredible entrepreneurs looked like. I got to really you know go and go into meetings with them, pitch them. And I remember the first one I pitched on a project you know I got totally smacked down. you know I just ate humble pie completely. Prior to that, I would go talk to customers and you know I would just wing it and any so any deal you know i would I would generally close pretty effectively. This time, I talked to an incredible entrepreneur who was asking me, where iss the where’s the data? Where’s the preparation that you have for my specific company on this?

Matthew Kligerman: and Uh, it really up my game. I learned, you know, to go into meetings, another another level of data and preparedness, uh, to be able, and also just to know what excellence looks like, uh, in the world. It was really inspiring for me. And so that company, I essentially kept running, uh, at the same time I hired a manager to go run it while at, while at city, uh, city eventually asked me to go down to Brazil for a one year project down there.

Matthew Kligerman: And that ended up becoming a decade long, incredible journey.

Alejandro Cremades: Well, how do you go into entrepreneurship again? You know, how do you find yourself in breath sale and then also into the venture world again?

Matthew Kligerman: it

Matthew Kligerman: Yeah. I mean, honestly, at that point I was getting ready to leave Citi. I had a great boss, but there was a lot. I just felt like I wasn’t really learning or growing or using all of my skills and the way I could, but I didn’t know what I wanted to go build.

Matthew Kligerman: City offered me this chance to go down for a year to build a business down in Brazil. And honestly, it just sounded like a great adventure. Who wouldn’t want to go have a have a year down there, learn a new language, meet new people, have fun. So I went down there not expecting only thinking it’d be a one year journey. That was it. And I mean, first off, on a personal level, I completely fell in love with Brazil. I mean, the the more than anything, the people in that country are just incredible, you know, the most warm, welcoming, fun, loving people. it’s It’s really special and had a great time in in the year there personally. But also when I moved down there, you know I had to set my life up completely. And I had to go through the buying process as a consumer in Brazil with all these different brands. I had to go get internet from my home.

Matthew Kligerman: I had to go get a mobile plan for my phone. I had to go open up a bank account, get a credit card, get health insurance. And going through this experience as a consumer, it I felt like I had been teleported back like five to 10 years from the comparison in the US.

Matthew Kligerman: Very little was online. What was online was really inefficient acquisition flows. I think they would all take you to a call center once they generated a line where you wait on hold with an agent for 10 minutes, speak to someone you could barely understand over the phone.

Matthew Kligerman: calls getting dropped, you know terrible customer experience. And many of the times it wasn’t even digital. It was still brick and mortar stores or people who would literally come to your house to come sell you a health insurance product with a giant 100 page book of plans that you would try to understand that they probably didn’t even understand. And so going through that experience as a consumer there, it just made me hyper aware that brands and these in Brazil, it big brands were spending billions of dollars in digital marketing and just wasting it. I was just going down the drain with these inefficient conversion funnels and not being able to really, one, convert those customers effectively and also create great experiences for customers interacting with their brands. and I got really excited to build something in that space. Didn’t know what it would be at the time.

Matthew Kligerman: and so I quit my job at Citi and I convinced one of my business partners. We we have three business partners at Ascali, three founders, myself, Ken Diamond, and in a Brazilian, Daniel Hosa, who joined a little later in the story. ah I somehow convinced Ken, this guy ah who I kind of barely knew at the time, but we had a strong affinity for each other.

Matthew Kligerman: And we’d been mentoring each other on each other’s businesses at the time. Somehow I convinced this guy to come down to Brazil um with a one-way flight. I got him an apartment next to mine, a cell phone ship, and a bank account in my name. ah And convinced him to come down to help to explore this business idea with me and what could we go build in this space. And we got really you know we got really excited about built, we didn’t know what we wanted to build, but we knew there was this big gap in the market around ah efficient efficient customer acquisition for these brands. ah And so we started off actually building

Matthew Kligerman: ah a bootstrapped digital agency down in Brazil. Not that we wanted that to be our long-term business by any means, but at that point, we barely understood Portuguese. We didn’t know anyone to hire. We didn’t know any clients to go talk to. ah ah We just felt like we had to understand the market a little bit better. And we felt building an agency would be a way to start building a A-plus team of digital marketing talent, train that team, understand the ecosystem better, and be ready to actually go in to go build whatever that vision would be for ourselves. As we we did that for about 18 months, you know bootstrap that business, which was ah you know i mean such a scrappy experience. As I look back to it, you know it really feels like a Gabriela Garcia Marquez novel of this mix of fantasy, ah fiction, realism, all blended together. you know I can barely tell what was what as as I think back to those early scrappy days in Brazil.

Matthew Kligerman: And eventually, we moved into what became our long-term business model. ah from From the agency business, we started helping brands beyond just the digital marketing side of things, of lead generation, and actually into full funnel conversion, where we would not just generate the leads, but we would actually convert those leads into sales for our customers. And in doing that, we actually perceived the biggest challenge that brands had was specifically in that conversion side.

Matthew Kligerman: And then we went all in towards building out a conversion platform for brands in Brazil, for banks, for telcos, insurance carriers, to help them convert their customers more effectively. um this is a This is, I can share more in a little bit, but this is, that became the real Escali that we’ve now built.

Alejandro Cremades: So I guess say for Scali, for the people that are listening, what ended up being the business model? How is the company making money?

Matthew Kligerman: Yeah, so so basically we the product is we built out a conversion platform to help brands convert their customers more effectively. That conversion platform is a combination of lead scoring when a lead comes in to the to the platform to decide the chance of that lead being able to convert and a lead routing component to be able to decide what is the best channel to route that lead into. And then we will actually send that lead to our own, if it makes sense as part of the conversion routing, to our own sales ah ah conversion via chat. And that conversion via chat is now enabled with our AI sales agents to be able to convert those customers at a much lower cost and higher conversion rate.

Matthew Kligerman: We do the customer onboarding, marketing re-engagement, and then we send the conversion data back to the marketing platforms of the brands for them to actually have accurate marketing ROI attribution. ah Doing this effectively, what is our end product for the brands that we’re working with? It is higher conversion rates. On average, our customers increase their conversion rate by 50%. Our better success cases are over 200% growth in conversion rate and lower conversion costs.

Matthew Kligerman: The most recent aspect that we added on was the actual AI sales agent’s components. In the past, we actually would direct those leads into our customers’ call centers or into their human chat teams. Now that we’ve added AI sales agents on top, ah that basically connects into our customers into a knowledge base that we build from our customers on their products and how to sell. We connect and integrate into our customers’ ah systems for credit check into their systems for ah product availability, pricing, documentation, and contract finalization so that our AI sales agents can actually drive that conversion 100% via chat. In Brazil, this actually ends up being mostly via WhatsApp, which is the primary chat platform leveraged by consumers just to talk day to day in the market. And now it’s been greatly adopted by brands. And the way that we charge the business model specifically

Matthew Kligerman: is our our um value prop for brands is increasing their conversion rates, getting them incremental customers. And that’s how we get paid. We get paid for actually driving incremental sales for our for our brand for our brand partners. We implement the technology and we measure every transaction that gets processed with a platform and we get a percentage of each transaction. And where we really start making money is when that becomes incremental sales for the partners.

Alejandro Cremades: Now, you guys have raised a about 50 million bucks. I mean, you have 400 employees, which is a really remarkable. How has it been through the journey of ah of of raising this money you know in in in a country like Brazil?

Matthew Kligerman: Yeah, well, I mean, in those in those early days, you know, it was we didn’t raise money initially when we started the business, you know, is at first completely bootstrapped. And, you know, we their office was in my in my apartment back then. And we had clients, but it took us almost um six months or more to actually open up a bank account. The process was so complex by then. And um ah and I remember, you know, we would I would take the Metro every day or every other day to Avanita Paulista, where there was one ATM machine that would work with my debit card. And I would do the maximum withdrawal from my debit card from the ATM and come back because at that point, we probably had about 15 people working for us full time out of the apartment, I’d come back, and I would pay people in cash, you know, whatever it was 120th of their salary.

Matthew Kligerman: And then the next day I would go back to the ATA and withdraw the maximum amount and get people the next one-twentieth of their salary. Eventually, you know, we actually got kicked out of my apartment as an office. The building did not let us stick around there in the residence, so we had to go figure out what our new place would be. We ended up be getting our new office above a little pizza restaurant in Sao Paulo.

Matthew Kligerman: and Yeah, we grew the business, you know, basically, we were able to open up the bank account to start getting paid by customers and grew the business initially cash, you know, but his own cash flows. But then we saw this bigger vision to build out this conversion platform that would require more serious product investment, ah and a much bigger opportunity. We closed our first customer on this a big telco in Brazil. And once we did that, we then raised our first institutional round of capital.

Matthew Kligerman: um Back then, there weren’t many options in Brazil. I think there were maybe only two investment funds back then who were investing in tech, software businesses, early stage with you know standard VC type terms. And we were lucky enough that one of them chose to invest in us. they led that They led that first seed round and we had a handful of angel investors join along in that journey. They joined too. We raised about 1.1 million in that first round.

Matthew Kligerman: we That gave us enough capital to go build up the platform, go launch this first customer. We grew their sales dramatically. but We became their biggest sales channel, actually. And then we ah we closed an additional telco partner and raised additional capital for that. And so we then raised capital from Global Founders Capital. Our first investor who who led that round was Redpointy Ventures. ah The second round was GFC. Redpoint followed along in that round.

Matthew Kligerman: continued scaling, we then branched off into additional sectors. Our platform is very built out in a handful of sectors that has a lot of system integrations with and data integrations with. And so we expanded from telco into health insurance and into banking. When we did that first expansion to health insurance, we closed around with Kasek, which ah were the original builders of Metacada Liberty and incredible operators and partners for the business. We closed about $7 million with them in our Series A round. We then went into the banking space and closed some partnerships with some large Brazilian banks, helping them to convert on products like auto finance loans, collateralized loans, account opening, credit card, home equity and others.

Matthew Kligerman: ah and When we did that, we then closed our most recent round, which was with QED and with Invis. QED is some FinTech investors who have a lot of experience that was really relevant to our expansion to the banking space and also knew our business model very well. And Invis was is a ah family office out of New York, ah Evergreen Investment Fund.

Matthew Kligerman: We always wanted to go build a long-term company. We never wanted to build something to sell, something we would one day perhaps sell, but ah ah built a company that whenever we have the option to sell, we would always want to go double down on and and keep taking to the next level. And they were great investors who fit with our vision, strong evergreen fund and really long-term thinkers and brought a really good private equity perspective ah to the table too. So that’s kind of the major history of the rounds.

Alejandro Cremades: So in in your case, eventually you um you came back um and now you’re in in North Carolina to um basically be with family, be closer. I mean, obviously, Brazil is quite a trip. So you came back in and and you took the executive chairman you know role there. Now,

Alejandro Cremades: In your case, you know you ended up the company you know hasn’t sold, but you did a a a per partial exit. and I think that this would be interesting for the founders that are listening you know to be able to to understand how typically these structures would work.

Matthew Kligerman: Yeah.

Alejandro Cremades: But in your case, you ended up doing a partial exit via secondary. so how How does that typically work and in what can you share you know with the founders listening on maybe how they should think about that or go about it?

Matthew Kligerman: Sure, I don’t know if I can speak to how it generally works, but I can I can speak to my experience and in and how it worked. For us, it was actually pretty organic as part of our fundraising rounds. ah We.

Matthew Kligerman: were lucky enough to ah be oversubscribed in our rounds. We were pretty cash efficient, didn’t need to take on much capital, and ah we had multiple investors wanting to participate in the in the company. And it it just seemed like an appropriate opportunity for us. you know as As entrepreneurs, you know you have so you’ve so much concentration in one business.

Matthew Kligerman: which is amazing and great. It keeps you completely focused and with total drive. But at the same time, you know it i mean it’s definitely is you know a little nerve wracking on that crazy roller coaster of entrepreneurship. you know I talked about a lot of the high moments and successes of raising rounds and getting new clients and expansion, but there’s definitely dark, challenging moments in that journey too. And but when all your wealth is tied up in one single asset, that’s a little it’s a little scary at times.

Matthew Kligerman: So for us, and we’ were raising when we were raising these rounds with investors, it was ah our last couple of rounds. um Basically, ah we talked to investors about the idea about buying out a portion of mine, my co-founder’s shares, um as we were to get them the equity participation that they wanted into the company, um and also take a few chips off the table to help us sleep better at night.

Matthew Kligerman: ah It was enough for us to help us sleep a lot better, um but not so much that you know we were not completely vested in the business. you know Still 95% of our net worth and and is focused on the company, but it was a nice breath of fresh air and relief for us. And for our funds, it it was ah it was small enough that they didn’t worry about ah you know misaligned interest or anything like that.

Matthew Kligerman: ah but relevant enough for us to sleep better and honestly probably make better decisions for the company because we could focus more on building the biggest company we could with the greatest value and worry a little bit less about risk mitigation.

Alejandro Cremades: So then in this case you know for you I mean you are um you’re a climber and you’ve climbed the El Capitan which he is a you know obviously we’ve all seen the documentary of free solo and you know incredible without the ropes but Climbing a mountain to a certain degree is just being a founder because you it’s just like the the hardships and the uncertainty. I think that you you kind of like experience that too. so I guess from climbing mountains, from maybe climbing El Capitan where you’re like five days climbing, sleeping you know in vertical ah mode,

Alejandro Cremades: What kind of lessons you know have you taken or you find similar to entrepreneurship when it comes to, let’s say, leadership but or when it comes to um you know maybe like business?

Matthew Kligerman: Yeah, so so it’s interesting that Escali, the company actually, you know it’s the infinitive although it means scale in Portuguese, it’s the infinitive of scale, it’s also the infinitive of climb. ah And it was always a very large metaphor for us in the company. And that’s because my my business partner, co-founder, Ken, and Daniel, the other co-founder, I just got him to agree to go on a adventure with me soon up a cliff. and But Ken, when he first arrived in Brazil, we traveled around a bunch and I took him on some pretty wild climbs together.

Matthew Kligerman: I mean, they were they were things. And then I look back, you know he was definitely not at all prepared for the experiences, but it was actually incredible what we did as a team together. We climbed some really big faces, thousand foot faces in Brazil, took them on some amazing adventures. And honestly, it was an amazing test of our partnership together to go through real hardship together, scary scary experiences looking down at 600 feet below you.

Matthew Kligerman: and have trust in one another, have really strong communication, be able to interact in really stressful environments well, to plan together the logistics around it. Honestly, it was an amazing way for us to go test our partnership before launching launching the business. and When I climbed El Cap, that was with Ryan Williamson, one of my best climbing partners. we’ve We’ve done a few routes in Yosemite.

Matthew Kligerman: On the El Cap one, we ended up sleeping for four or five nights on this vertical face as we got to the top. ah And yeah, I mean, when I think about the experiences that we had together or with other folks, um friends of mine, Ted Hester, we climbed some stuff in Patagonia together. I think through those experiences and those partnerships that I had with people, I think there’s so many lessons around partnership, honestly. you know and and the And the partnership, not just the physical element of the partnership, there that is one component of it. When you’re going after a route, often it’s good to have people with complementary skill sets who can lead different sections of the route based off what they’re strongest at, if they’re stronger at ice climbing, or stronger at free climbing with their hands, or stronger at aid climbing, put a little little equipment in the rock ah to be able to pull on.

Matthew Kligerman: Uh, but also not just the physical component of that partnership, but also just the emotional component of that partnership to be able to support each other, energize each other, to be able to look at an objective that honestly seems almost impossible and absurd initially, but to be able to train together for that. And then when you’re going on that objective to then take it step by step, you know, it’s, it’s when you look at that man from far away, it seems impossible. And, and.

Matthew Kligerman: At the end, it’s really just one step at a time to go in that journey. And I think you learn there’s failures, like you don’t always go hit hit the summit, you know, sometimes you got to make good decisions to to come back. But you can figure out, you know, generally, there are many times where we didn’t hit the summit the first time, but we would replan restrategize, come back the next day or the next week or the next year, more learned, more prepared.

Matthew Kligerman: more trained, and go after and then have success reaching the objective. And so I think there’s a lot of these parallels that connect to business and the adaptation, needing to prepare and learn. And also to have honestly like ridiculous confidence in your ability, not necessarily to execute perfectly, but to be able to have the skills enough to improv along the way, figure it out, shift plans,

Matthew Kligerman: and then be able to execute the mission. So ah yeah, there’s a lot of lot of interesting parallels that and learnings. Maybe one last one I would share is also on risk mitigation ah and being able to execute really well under extreme stress. you know in In climbing, there’s many times where you are physically pushing at your limit and you need to you know put in little metal pieces into the rock to anchor you in.

Matthew Kligerman: And you have to be thinking really sharply at those moments. And you need to be able to both execute physically at your highest level while mentally staying really sharp. And to be able to block out the fear, of course, to be aware of the danger, but to block out the fear element that impacts your mental and physical capabilities. And honestly, entrepreneurship is very similar. There’s dangers all the time. You need to execute really well and sharply and not let the fear impact you.

Alejandro Cremades: So once an entrepreneur entrepreneur, always an entrepreneur. So obviously now that you have a little more time, what can we expect in from Matthew as the next chapter?

Matthew Kligerman: Yeah, you know, I’m so I spent the last I took a after moving to exec chairman, I took a sabbatical with my wife, traveled around, had a blast. But it was funny, you know, I always kind of looked at that sabbatical as, as, you know, it’s a trailer of the world and rock climb as you know, the the goal, the goal, you know, of where where to go get to after after the day of the company.

Matthew Kligerman: But within a month of that, I realized that is not fulfilling for me. As amazing as it was and fun, I just love building things. I like creating value in the world and for others. And ah i I was excited to go go back into it. I spent a little bit of time over this past year helping other friends of mine building businesses, a climate tech fund launch in the US.

Matthew Kligerman: a ah growth stage fund expand in the US market or another growth stage professional services company expand. But but I’ve now actually gotten some clarity on something I’m excited to go build into the US market. ah And it actually leverages a lot of what I felt from the experience in Brazil. When I went to Brazil, like I mentioned initially, I felt like I had this crystal ball from the US.

Matthew Kligerman: and saw the world five to 10 years ahead of Brazil and could bring the best practices of conversion into into the Brazilian market. And now I feel like it’s the other way around. As I come back to the US s from Brazil, Brazil has actually leapfrogged the US s in technology in many ways. ah And one of those ways is the way that brands interact with the customers and around um being able to to to engage with the customers via WhatsApp. That’s one of the one of the ways that it’s just so much easier in the Brazil versus the US. I’m really excited to go build a business in Brazil ah to enable, or build a business in the US, s to enable US brands now to engage with customers via chat with Gen AI agents throughout the entire vertical of what they need for customers from not just the conversion side, but from

Matthew Kligerman: the ongoing customer support and the ongoing re-engagement of that customer, the ongoing fidelity of that customer, and looking at a particular vertical to go build that into. And ah it’s in the very early discovery stages, but excited to be diving into this.

Alejandro Cremades: So, Matthew, for the people that are listening that would love to reach out and say hi, what is the best way for them to do so?

Matthew Kligerman: um My LinkedIn is good, Matthew Kligerman, Gmail is there, matthew.kligerman.gmail dot.com. other one.

Alejandro Cremades: Amazing. Well, hey, well, easy enough. Well, Matthew, thank you so much for being on The Deal Maker Show today. It has been an absolute honor to have you with us.

Matthew Kligerman: Thanks so much, Alejandro. It was great to be here with you too.

*****

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