Chris Gladwin, founder of Cleversafe, sold his company to IBM for $1.3 billion and later raised $65 million for a new venture.
Chris Gladwin, founder of Cleversafe, sold his company to IBM for $1.3 billion and later raised $65 million for a new venture. The video discusses his entrepreneurial journey from founding Cleversafe to its acquisition by IBM, highlighting his experience in creating and selling successful technology startups.
it's very interesting to watch us apply all of our technology entrepreneurship thinking to the outdoor recreation industry and doing things that have never been done before you know that would be the advice which is you've got to get the timing right like just because you can make it doesn't mean the market wants to buy it [Music] alrighty hello everyone and welcome to the deal maker show so today we have an entrepreneur that has done it not once but multiple times you know what they call the full cycle of the entrepreneurial journey so i think that again you're going to be very much inspired the ups the downs you know the successful exits uh the capital racing i mean you name it without further ado let's welcome our guests today chris gladwell welcome to the show hey great great to be here looking forward to the conversation so originally born and raised there in ohio so how was like
growing up in ohio pretty midwestern you know pretty um i guess uh stereotypical you know just went to school mowed some lawns you know got good grades that's pretty much what i did and obviously you didn't get to out of ohio much until you went to university so i guess how was your your upbringing there in in ohio i mean anyone in the family that was into building companies or business or how did you get that bug no not not really um i don't know it was just always something that i wanted to do and um and i remember one of the companies we'll talk about later music now we had a musician as a guest speaker guy named corki siegel and uh we asked him like how do you write songs and he said you just have to learn to let them out you know if you're really a songwriter they're inside of you and i think that's true uh at least for me and i think a lot of people that are entrepreneurs you just
have to let it out it's what you do it's who you are and you just gotta express it absolutely so obviously getting out of ohio that happened with mit so uh how did you land in mit i mean how was that for you like getting out of the out of the state of ohio for the first time how was that um you know i had been out a little bit but never more than like a weekend or you know a week vacation and it was culture shock you know going to boston and like a subway and homeless people and tall buildings and all that kind of stuff was was was was new to me but mit is just a phenomenal place and for me it was transformative it really gave me the experience to kind of operate on a global scale in terms of kind of innovating that that's mit is just wonderful in that respect and especially engineering so i mean probably you were you had that problem solving in you yeah for sure i mean it i mean mit
still kicks your butt believe me you know you everyone that goes like you're the smartest kid in high school and then you go there and you're just like average and uh that's a good experience really because it it really challenges you and makes you work harder and also makes you humble you know you realize you know you're not that great you know you've got to work just as hard as everybody else so obviously the first the first gig you know really out of out of school was martin marietta and then after that you did seniors data systems which was essentially the segway to to building your first baby you know your first rodeo so so tell us how was that segway into cruise technology and and you know like that incubation process and bringing it to life and so forth i was really fortunate in a lot of ways because um that was what enabled me to start my first kind of big venture back startup
cruise technologies um but i but back then it was pretty uncommon i think it's even still pretty uncommon for someone really young and experienced kind of early in their career to lead a company with you know a lot of employees and a lot of capital that goes into building hardware but fortunately i had helped build that division at xena theta systems while i was there that we spun out into this new company so i had the advantage of i knew every customer i knew all the engineers i just i just knew the business and so even though i i was relatively young and i didn't have a lot of experience i really was i knew that business better than anybody and so that's why i got the opportunity which was phenomenal and how did you guys capitalize this business so there was a in the um in the mid 90s there was uh a battle um for kind of the dominant you know end using computing end-user computing
architecture and the pc had really kind of risen to prominence but there was a real battle um that sun and netscape and oracle waged to establish an alternative architecture which was really a network computer a a thin client and um so we were in that battle cruise technologies and we were the company that made all the all the mobile or wireless thing clients in the market except one so all the motorola's products all of ibm's products wise products telus's products et cetera like behind the scenes we made all those for them um so that was pretty cool to be in that battle the problem is microsoft and intel ultimately won and you know uh it was just like by ourselves you know little cruise technologies ultimately couldn't compete with those giants yeah and obviously in this case you guys ended up selling the business you know to uh to motorola and ntc and and and that was kind of like the
the end of this rodeo but then you started another one music now so yeah you know obviously as they say once an entrepreneur always an entrepreneur so tell us about music now and before music now one lesson that you learned with cruise technologies well i mean i think that one for sure the lesson was i thought that the way to really be successful as a new technology company was to to do something that was just really really hard and to build a team of people that knew how to do that better than anybody else in the world the problem with that is in is you can overshoot the market so so basically we were building ipads 20 years before the market was ready for an ipad and obviously the market now you look at it and yeah mobile computing and thin clients essentially you know most of how apps operate today is more and more than client so we were right about a lot of stuff but if you come to
market decades early it's not going to work so that that was the big lesson was you you got to time the market that's the most important thing so that you enter the market right as there's some kind of new demand for what you bring so music now was the next one and you alluded to it earlier so so how did the music now come about well the way i started music now um was really a calculation um you know at that time music was a plastics distribution business which is music would be printed on a cd that that dominated but i thought that you could see this every year bandwidth was getting faster and hard drives were getting bigger and cpus were getting faster and so i i thought as soon as you know kind of the basic cpu that comes in any computer could decode or encode compress or decompress music in real time in other words as fast as you can listen to it and then as soon as the bandwidth
that goes to most houses you know for broadband is fast enough so you can hear in real time something that streams in and then as soon as the average size of the hard drive which was always increasing uh you could hold an advertised music collection on about a third of a hard drive i thought as soon as those three things happen this thing's going digital and in in and that was right and that's uh that's why we started music now i know you see here another another exit so you sold that to circuit city so what was the lesson learned from music now well you know we were a little bit early there too um but what really made that business unable to go is we couldn't get the rights um needed um to do that effectively i mean i i don't need to do a focus group with you to know that we all knew that that what the the market really wanted was to buy a song for a dollar like that was obvious but we
just couldn't get that right at that time all we could do was sell a whole album for 15 like again you don't need to do a focus group to know that's not going to sell as well as a dollar song we just couldn't get the right to do it and apple did and that's a whole nother story we don't have time for today apple was like almost out of cash almost out of business when they launched the ipod and itunes and you know two trillion dollars later here they are but i think the lesson there was you just got to be in the right place at the right time and and we weren't got it so at least you know this was the segway to your biggest exit to date with clever save so yeah i'm sure that you know at this point you had two two startups you know under your bill two companies that you had built from the beginning all the way to the exit to doing the transaction but you know i'm sure that in cleversafe you
were able to…