Neil Patel

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In the realm of startups, few narratives are as compelling and instructive as Kris Bliesner’s journey. With a career from early-stage ventures to navigating hypergrowth and transition periods, Kris offers a wealth of insights into the dynamics of building and scaling businesses.

In this captivating interview, Kris shares his experiences, challenges, and triumphs, offering a roadmap for aspiring entrepreneurs and seasoned professionals. He talks in detail about founding three companies and evolving six in all.

Kris’ latest venture, Vega Cloud, has attracted funding from top-tier investors like Album VC, Cowles Company, Aleka Capital, Rudeen Management Company, and Spokane Angel Alliance.

In this episode, you will learn:

  • Prioritize customers and revenue realization to anchor your startup’s growth trajectory.
  • Embrace diverse experiences to lead technology teams through innovation and adaptation effectively.
  • Market timing and customer adoption are pivotal for startup success, highlighting the importance of readiness and receptiveness.
  • Strategic partnerships and investments are essential for navigating hypergrowth and scaling ventures effectively.
  • Bridge the gap between reporting and operations to optimize cloud management and drive efficiency in enterprise solutions.
  • Stay true to the core mission while fostering a customer-centric approach to build trust and drive sustainable growth.
  • Entrepreneurial resilience, adaptability, and unwavering commitment are the cornerstones of navigating the startup journey amidst challenges and triumphs.


For a winning deck, see the commentary on a pitch deck from an Uber competitor that has raised over $400M (see it here). 

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About Kris Bliesner:

Kris is the CEO and Founder of Vega Cloud. He was the Chief Technology Officer (CTO) and Co-Founder of 2nd Watch before that where he oversaw strategic and technical development of 2nd Watch’s cloud-based products and solutions.

Prior to co-founding 2nd Watch in 2010, Kris held many top IT positions with companies including Microsoft andAmbassadors Group.

As the CIO for Ambassadors Group (EPAX), Kris spearheaded the replacement of the company’s legacy ERP platform and implemented a business-first CRM system as part of a strategic overhaul of Ambassador’s IT infrastructure.

As a member of the core executive team, he helped drive strategic partnerships and advised on M&A.

As Microsoft’s Director of Sales, Marketing and Services Infrastructure, Kris managed content and communications tools for the company’s 60,000+ global Sales, Marketing, and Services workforce.

During his tenure at Microsoft, Kris received several awards and accolades, including two divisional “Field Productivity” awards and a Circle of Excellence award (top 1% of Microsoft).

In addition, Kris owned his own consulting business specializing in system architecture, database design, and software development. His clients included Onyx Software, Ascent Partners, National Flood Services, and Microsoft Corporation.

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Connect with Kris Bliesner:

Read the Full Transcription of the Interview:

Alejandro Cremades: Alrighty hello everyone and welcome to the dealmakerr show. So today. We have a really exciting guest. You know I guess that they has been evolving 6 different startup. Obviously he’s founded 3 of them and he’s gone through the whole cycle building scaling financing and all of that stuff. We’re gonna be talking about how to manage. Hypergrowth especially in a market that is early versus let’s say a market that is not as early also the difference say you know when you’re when you’re thinking about like really building something before it is really time when it’s kind of like early and then also transitioning from a big corporation to perhaps you know venturing to the. Startup world. So very exciting conversation I had and without further ado. Let’s welcome our guests today Chris Blier welcome to the show. So originally born and raised in Washington state give us a walk through memory lane. How was life growing up.

Kris Bliesner: Thank you.

Kris Bliesner: Good. You know there’s not a whole lot of of net new technology businesses happening here on the eastern side of Washington State so after college I moved to the Seattle area I did a couple of startups over there and worked at Microsoft really wanted to scratch that technology itch I studied computer science in school and so. Um, but took more of a less of a a physics side of computer science and more of a business management side of computer science. So I was interested in business and accounting and those kinds of things but also technology and software development. So it was a great opportunity see’s a fantastic market for that stuff so surely after college moved over and and had a great start to my career. There.

Alejandro Cremades: So Obviously you know like your career you know has been really incredible I mean you’ve done startups you’ve done corporations. But in this case, you know for you, You know you got into the whole startup world Bia shop the Globe. So. How was that team you know experience of venturing into into the world of of smaller companies.

Kris Bliesner: Yeah I think when you’re young, you’re probably more open to to taking risks probably because you just don’t know any better. But I think for me startups always always are fun to work at but when I was at Microsoft as a consultant contractor. They offered me a full time job. It wasn’t what I was thinking it was in the. Sort of ah an it group that I wasn’t super fun of at the time and so I thought okay maybe there’s something better out here and I looked around and and I found this job at at shoptic globe. It was a company that was just being bought by out of New York during the the hype cycle of the late 90 s and so a lot was going on. There’s there’s a buzz in the office. A lot of lot of excitement. Um, lot of new tech being created on the fly and so it just felt like a much more interesting place as a young person who was doing working on software and voma to say wow I can break barriers here I can I can work on new things that nobody else is doing and um, there’s a lot of of great opportunity here and so I think that was a lot of the excitement of. Trying out the startups for the very first time at shop the glow was was an amazing experience and and I still have lifeline friends from there today and several of them are our ceos actually of other very successful startup businesses. So I think it. It’s sort of ignited up a passion inside of a bunch of us for sure.

Alejandro Cremades: And also what was that the journey like to go from like more like the business development or corporate development to like the Cto I mean you’ve transitioned quite a bit and I know that going from the business side to the technical side and vice Versa is not an easy. Transition. So How was that for you.

Kris Bliesner: Yeah, you know I I realized that in order to effectively manage technology. You’ve got to try different positions. So I think it’s it’s really hard if you’re not if you don’t try out an engineering position or a testing position or or a project management position because it’s hard to manage those folks, you don’t know what they if you haven’t walked a mile on their shoes as they say. Um, and so early on I I job hopped around a bit to get some of those experiences so I could see what I wanted to do and I realized I definitely wanted to manage technology and so that sort of grew into the technology management side and once I was there I realized wow a lot of the things that you do with a technology management career. You could do as a Ceo of a technology firm. Um, and so there was some nice overlap there you you manage a budget you manage a pnl um, you do all those kinds of things and so for me, it was just a natural sort of thing to say hey listen I ah I love and and love working with people love working with technology love building new things. There’s a great way to sort of combine all those things together. And the Ceo role of ah of a technology startup.

Alejandro Cremades: So then so then for you, you know like when when you ended up going into into the startup world and you did that actually the first time around was with parking I how was that how was that for you because you guys were a little bit ahead of time.

Kris Bliesner: Yes, yeah, it was. It was an interesting time again. Parking eye was a technology. We developed to automate parking lot attendant stuff so back in the day and I’ll I’ll probably date myself with the younger folks but back in the day you you shove Dollar bills in in a slot somewhere and somebody would. Come along and collect them at some point it was a cash-based business and before you know pay stations were thing before automated sort of a lot of tennis where thing and so we developed a technology that that had a camera associated with it integrated with the pay station and was really really helpful to sort of cut labor out of the system and and. Really cutting edge but the reality was that was an industry that was wrot with folks that had 0 interest in technology they were doing just fine by collecting cash and and doing the business that way and so they weren’t really motivated to go out and buy these pay stations and to buy the cameras and it was. It was great technology that that sort of. Didn’t have the market ready to buy it and so we ended up actually selling that tech to a firm in the Uk who went bananas with it that that business I think grew over 100000000 and in enterprise value and like a lot because the market there was was ready for it right? They were already doing license plate recognition technology. And so the the concept of having automated pace stations was was easy for them to to get their brain around whereas the market in the us was was still I think a decade too early.

Alejandro Cremades: And how is it like you know for you like I obviously this experience um going through the full cycle being able to do also a transaction I’m sure that that gave you more visibility into the whole thing you know going from first base all the way to to to to to hitting the home run.

Kris Bliesner: Yeah, it does and and I mean the the thing with parking eye is it never really became a ah huge business for us in the us. So it was kind of a a small deal for us. But I think what was interesting was just working through the the concept of going from an idea all the way through to production deployments and and. And bringing in revenue from customers all all the things that are critical to to building a business having seen that and and done it from a founder perspective was was really eye-opening because when you’re working at big businesses when you’re working at Microsoft or when you’re working at you know somewhere else you you don’t have that experience. You don’t realize how much goes into taking an idea from concept. All the way to reality and and and invoicing the customer and and getting that done and that there’s a lot There’s a lot there and that’s why a lot of businesses struggle to to get off the ground is because there there’s an art in terms of how you launch product. How do you How do you find customers? How do you get them to pay for what it is. You’re building. How do you partner with them all those kinds of things.

Alejandro Cremades: So then so then for you right? after this I mean you go into like a journey of having your own consulting. You know you also ended up working at Microsoft you know so how do you go from? you know, ultimately. Experiencing startups to going to like a larger corporation I mean that’s quite the shift.

Kris Bliesner: Yeah, it is you know? and and I would say it’s probably more driven by family and and personal needs at the time we had. We started to build a family have a couple of kids and so at that point you know you realize you want a little bit more stability in your life. Ah, because if startups can be off right? You don’t know where your next paycheck is coming and um, you know if you if you don’t hit something groundbreaking and things take off like a rocket chip which doesn’t always happen. Um, there’s a lot of ups and downs and that can be tough when you’re trying to put food on the table for your family and so for me having done that for a number of years I really wanted to to experience something a little more stable. Ah, for a little while and and and I knew I had a lot of capabilities that I could bring to the table for for a firm like Microsoft and so I really enjoyed my time there and and had some fantastic opportunities thanks to to the groups that I work with the teams I worked with and and my managers there. But I think at the end of the day it was another life. Ah, decision that sort of drove me to move back to Spokane take ah another job outside of Microsoft but for me, it was ah it was a great learning curve. Ah you know they they do their own things they’re they’re a factory in terms of developing software and so I was able to see software development from ah a large company perspective which was great so understanding how enterprises think about things and how that whole process works. And developed and and helped launch some really big products. There was part of the sharepoint 2007 chip cycle and and some other products there as well and so that that was a great experience for me to just go through and I think everybody who’s thinking about technology or thinking about software going through a ship cycle is important whether it’s at a startup whether it’s at a.

Kris Bliesner: Ah, big corporation and obviously the ship cycles at big corporations are longer so it takes a little while to get through but seeing it from end-to-end is something that’s super important because that that way you can understand you know what? what happens in the beginning what happens in the middle. What happens at the end and how it’s all related and that that certainly helped set the stage for. For me to to actually go out build software for a living.

Alejandro Cremades: So so at what point do you realize that they maybe it’s time to go out it again with second watch.

Kris Bliesner: Yeah, you know it was funny. We we we had built this interesting business with ambassadors. It was student travel educational student travel so you could get college credit for percent in your junior high and high school kids overseas and it was a great business. Doing really well and we started to play with the concept of cloud so this was probably 11008 Amazon had I think at the time 3 services e c two s 3 and I think simple queue service at the time or whatever it was and so we thought wow we we do these marketing campaigns once a year they’re three months long they’re they’re super intense. But. But then we’re done and and the the computing power is just sitting there like we had this huge data center we built and we had ah and ah secondary data center in Seattle for backup and it just felt odd that that we had to have this gear sitting there nine months of the year and not using it and so the cloud came out. We’re like oh wow you can pay by the hour and then you can give it back and you don’t have to pay for it anymore. There’s some There’s some interesting ideas here and so and then it leveraged Amazon’s global footprint and so we started experimenting with ambassadors around how we did that it worked so well for some of the workloads we did that I built a business plan for how could we get away with not having any infrastructure. Ah, running in in in a data center because as a small company if you’re not a a technology company running a data center is really really painful. You got to have a lot of specialty skillsets. You got to you’re working with 20 or 30 different vendors. Well all those vendors collapse into 1 or 2 vendors right? You’re getting all your stuff from Amazon now.

Kris Bliesner: Where you used to buy from hp emc dell cisco all these F5 all these other vendors you’re getting all that stuff now from one vendor it was like wow this is ah this is a shift in the technology landscape very akin to mainframe and client server this this cloud thing is is a really really big deal and so for me I wanted to experience more of that. But I realized um. That it was more than just one company I didn’t want to just do it once with ambassadors I wanted to do it all over the place and so we set out we looked in the market and said okay, what’s out there. Well Amazon said if you needed help you could go look at the forums send us an email and then maybe we get back to you. They really have a customer support desk or any of those kinds of things at the time and so. We thought wow what a great business we could set up to help companies figure this stuff out because we’ve done the math. You know it’s much much cheaper for non-technical technical businesses to have their data centers run in Amazon and all that gear running at Amazon because the rally is you don’t need to run at 24 7 nobody does right? All your stuff is is dynamic. But. The dynamic model doesn’t exist on-prem it exists only in public cloud and so that that business model changes. What spurred everyone to move stuff in so we formed second watchch and we quickly became Amazon Web Services goto partner and we did some of the largest data center migrations into public cloud that have ever been done. Um, for brands like Coca-cola Nike Starbucks Toyota Adobe Thompson Reuters you name the large brands we moved their data centers from on-prem into a to bs at the time and then eventually Microsoft and Google when they started to catch up but it was it was a really nice experience to sort of see this business idea of a market that was.

Kris Bliesner: you know super early so you know again we did some of the very first data center migrations we did the first worldwide data center migration where we had a data center in the us one in Sydney and one in Europe and we moved them all at the same time into into the cloud and so those kind of concepts didn’t exist before and so having gone through that that was a really unique experience.

Alejandro Cremades: So so in this case I mean you guys raised some money too I mean how much how much money did the company raise throughout. It’s a life and and what was that journey like to of of raising the money.

Kris Bliesner: Um, with it.

Kris Bliesner: Yeah, so I raised about $40000000 myself across 3 different firms. So we started with madrona you always start with friends and family. So we we certainly did that but but prior to this we really hadn’t had a big win yet. So the friends of family stuff wasn’t huge for us and so we moved quickly to ah. An institutional investor so that was madrono capital out of seattle they were great to work with and then we closed a growth round with Columbia capital out of Washington Dc and then then the the last round I closed was with top tier capital out of San Francisco um all great firms to work with did a great job supporting us. We sort of migrated the business from. Kind of a technology company in general to more of a professional services managed services business. That’s not my background I’m more of a software guy so we brought in a Ceo to run the business and he ended up raising probably another 20 or 30000000 I don’t know what the total was because I left in 2017 but but it was ah it was a great opportunity to see this market. Evolve right? So all this massive stuff back in 2008 there was. There’s very little run on Amazon um, the market for cloud computing didn’t even exist and I don’t even think gartner had a magic quadrant at that point um to where we are today where Amazon’s a $100000000000 run rate business from just the as portion alone. That’s a massive swing from where it was even you know a decade ago and so just to have been a part of that was was really awesome.

Alejandro Cremades: And what was it like to manage the growth you know, especially you know during the early days and what would that transition look like from early stage to to grow stage 2

Kris Bliesner: Yeah, it was it was hard in that it was. It was my first deal and I remember having that conversation with Columbia because they’d asked me specifically and had you been ah a Ceo of a growth firm before and I said no I you know I’ve been a Ceo before but not not of a growth firm and it’s something that had grown this fast and in a market like this and so. There was a lot of of learning and that can be painful. We definitely had our ups and downs being more focused on the migrations because that’s what the the customers were looking for it allowed us to have a lot of revenue come in the door quickly. But it was also a challenge to sort of staff because you had to have people to actually deliver the services and we had customers. Um, you know, big banks or other folks that were doing big moves that wanted to use every single person that we had on staff and we’re like okay that doesn’t feel good for me like we need other customers and so you know just trying to manage that ah that growth piece both on the customer side and the employee side was a bit tricky early on. But I think we finally figured it it out and. Um, it’s still a great business. They’re doing well I think they’ve rebranded themselves but that was that was a really fun experience and and I left that company so started with from an idea and and really just a couple of cofounders and then grew it to 20250 plus employees.

Alejandro Cremades: So what? what? what trigger there for you to ah want to make a move and and get going with vega because I mean obviously you see once say you’ve um, build a company like that and you’ve raised the all that money you know it turning pages is not that easy.

Kris Bliesner: No, it’s not and and and so a couple things needed to happen one. We wanted to do some secondary so we could get because we weren’t in the in the place where we want to sell the entire business yet still growing and so we did a couple of secondary transactions to get their early guys out. They did really well depending on what time you got out there. The guys got seven x or 11 x. On their return so that was nice and then they eventually sold the business to sttelemedia that was after I I left the business but I think for me, it sort of had shifted into this kind of consulting managed services environment which is all about billable hours and those kinds of things and I done a little bit of that my career but but wasn’t a huge fan of it because it’s. A really hard business to be a part of right? you you sort of have to go find your business every single year. It’s not recurring the managed services side can be but but that again those those contracts are tough to get and so it was just felt like it wasn’t the core. What I enjoyed doing which was really software development. We had done a little bit of software development early on with second watch. But when. We got big enough. We realized that the team of a dozen folks. We had working on it just wasn’t enough to compete with folks that were doing it for a living and so we we jettison that and bought a competitor cloud health technologies out of Boston we use their software to run our business on and I realized boy there’s still some huge gaps here. Um there’s huge gaps in the operational side of it just in the functional side of of optimization and so we thought wow what a market opportunity now that the market has matured and these guys have been in business for 10 years and they’re not addressing the gaps. Why don’t we create vega as a way to to address these market gaps that exist today.

Alejandro Cremades: So then vega give us a walk through there through how you guys ended up putting together the business model How you guys are making money.

Kris Bliesner: Yeah, so Vega was really designed around the idea that the market was stuck in this reporting bucket right? So cloud observability cloud health cloudability cloud checker were were built from the get go before multi-cloud was the thing before scale cloud was the thing really built as observability tool to help you understand your bill and. Where costs were going and maybe do a little bit of recommendations but they weren’t great and at the end of the day people were werent it was noise people weren’t doing what they needed to get done because there wasn’t automation to go get the work done so it was sort of like your cars broke. You take it to the mechanic and you say hey I need your help and the mechanic says well here’s the part you need. But I don’t have them and I can’t fix it for you. That’s a pretty frustrating conversation to have over and over with customers and that was sort of where the industry was prior to Vega and so we really wanted to bridge that gap between reporting and operations and so that was the real big aha moment for us was how do we bring our capabilities having run a managed service provider which is all about operations. How do we bring that capability from a decade of doing that and combine that with the reporting capabilities that we also had early on um and build out this platform designed from from the ground up as multi-cloud scale large enterprise um to be able to do these things right? So that I can not only tell you where you’re spending and how to fix it. But I can actually help you fix it right? I can bring that automation forward and today if you’re going to do what vega does you’re going to have to buy a half dozen or more tools and that’s frustrating as a cio right now I’m paying 6 different vendors. So my costs have gone up if a manager service provider my my margins have gone down because my cogs are are much bigger.

Kris Bliesner: Like it’s just it’s it’s a frustrating experience. It’s very much akin to the security landscape honestly and I think why you see Palo alto and a lot of those companies buying more and more and trying to become a platform because Cios and csos are are frustrated because they’re having to buy 20 different tools to protect their environment and do something that’s important for the organization. But now I got to integrate those tools and. Figure it all out. Um, they want to avoid that on the cloud optimization side. So Vega is a platform that they can purchase and they don’t have to go buy another 6 tools and so it’s a way for us to to retire a lot of that stuff and and be able to have a platform play that that felt like the right business model for us and it’s it’s shown itself in in our customer base.

Alejandro Cremades: And you guys have raised about a minute 11 eleven million bucks. So what did you do differently this time around when he came to getting external money.

Kris Bliesner: Yeah, you, you know for us friends and family this time around was a lot easier to get because and a lot broader because we’d done so well with S Secondwatch so this is ah a second business in the same market I think you know repeatability and and and people that have experience means a lot. Lots of investors means a lot to customers. It means that you’re not starting from scratch. You’re not going to run into the same robots you you know this market you know cloud we have a lot of expertise around the table I think over 100 years on the executive team alone of of cloud when you add it all up and so from our perspective you know, being able to bring that to the table meant we were starting from ah a place of power. Um, not a place of weakness and so for us that made it a lot easier to to raise dollars we we have raised more than half of that 11000000 has been friends and family so in in that sort of bucket right of of sort of angel which is great. So I think that’s a great ecosystem to raise from. We continue to do some of that when we have the opportunity to. Um, and then we brought in our our first institutional investor album venture capital in 2022 they did our seed round. They’ve been great to work with again, just focused in on b two b saas so the the other lesson I learned sort of going through this as an entrepreneur is that that the Vc community as a whole. Ah, is full of folks that are interested in in lots of different things so people will look at it from a broad market perspective and say hey listen we just invest in geographical areas like the bay area or Seattle or whatever it might be or we focus on a particular niche right? Software consumerhealthcaretech whatever it might be.

Kris Bliesner: And my experience. The folks that have a niche tend to provide more value because they they have pattern recognition right? So you look your portfolio companies look a lot alike. They can share so when you sit down and you meet with other ceos you’re meeting with other b two b sas ceos and not you know the Ceo of a dog walking service like that’s not going to help me. Right? And so I think that’s the difference when you look at sort of finding specialized investors versus non-spealized early stage because those those are the times when you actually need some advice. You don’t want those folks running it and I never build a board or a company for for the investors of the board to run it but they can provide advice and and really be helpful and and. Ability for for them to do that is much more focused because all their portfolio companies are b two b saas so it allows us to have some common oddity around it.

Alejandro Cremades: So then so then in this case for you guys you know vision is a big one to secure money, get everyone involved employees I and you guys have like about 50 employees now if you were to go to sleep tonight and you wake up in a world criz where the vision of vega is fully realized what does that world look like.

Kris Bliesner: You know I think this market so the market today is about four hundred a billion I think it’s going to a trillion that the market that we service infrastructure and platform as a service in the next seven years it’s it’s tremendous I think there’s a billion dollar opportunity here for us I think that we can grow this company. It’s as large as we we want to grow it. Um, either by ourselves or with a partner I think there’s a lot lot of opportunity. We’re seeing that across the board in our pipeline and in the customers we’re bringing in that the industry as a whole is frustrated. They’re overpaying right? There’s a lot of waste in the system. We save our customers 25% on average. That’s even when we displace competitors and so that means you’re. Getting the value out of the competitor and also you’re still wasting money and again when you’re when you’re spending millions of dollars a month on public cloud and we can save you 25% those are it’s it’s a real sticky environment right? And so I think there’s a lot of of opportunity here.

Alejandro Cremades: So so obviously you know here we’re talking about the um, the future but I want to talk about the past with a lens of reflection if I put you into a time machine Chris and I bring you to that moment where you were thinking about starting something of your own and then.

Kris Bliesner: Check.

Alejandro Cremades: Say you had in the early two thousand s and you had the opportunity of let’s say have a chat with your younger self. What would that they be that business. You know piece of advice that you would be sharing before launching a business. What would that be and why given why you know now.

Kris Bliesner: Yeah I think a couple things one um revenue is king and so customers and and paying revenue is a customers paying you is is King and so focusing more on that versus raising money I think a lot of folks jump to hey I can find an investor who’s interested in my idea and then we’ll we’ll figure out how to build a business after that. Um, that’s that’s a hard row to Hoe I think from my experience you want to have part of product market fit is finding customers that are willing to part with their their card earn dollars and pay for your solution that that does something for them right? And so that that that mathematical formula that has to happen. There. Is really tough to get right because you have to have ah a business need you you can’t just have an idea searching for for business for business need right? like you, you’ve got to solve a core problem and I think the businesses that do really well recognize that they’re customer focused. They partner early early on with their customers and they they bring them along in the journey. So because the the risk that you have is that you tend to focus on on something shiny, right? like you’re doing some cool tech and tech is is oh always always in this bucket right? of hey it looks awesome. This is really cool. Why aren’t people paying for it. Well maybe you’re too early. Maybe maybe there’s not a market for that. maybe maybe the solution that that exists is good enough. There’s a lot of reasons why businesses won’t work and I think from my experience I would love to just go back and say hey listen focus on customers of revenue solving those problems. You will always have a business and then then you can decide how big the business is right? So whether it’s a eventually scale business or whether it’s you know a lifestyle business Whatever.

Kris Bliesner: Um, but but you need to to start with the business problem and the customers first.

Alejandro Cremades: I love it so Chris for the people that are listening that will love to reach out and say hi. What is the best way for them to do so.

Kris Bliesner: You can hit me out on Linkedin I’m on on Linkedin that’s a great way to connect that way. We can share on that way and and I I try to answer those messages once a week or once every couple weeks it’s I’m a little bit busy but that’s an easy way. Um, that’s probably the easiest way honestly to get all of me.

Alejandro Cremades: Well hey you see enough. Well Chris thank you so much for being on the deal maker show today. It has been an honor to have you with us today.

Kris Bliesner: Thanks alandra.


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