We’re honored to interview legendary American Entrepreneur, Josh Abramson on today’s episode of the M&A Launchpad Podcast. Josh Abramson’s is the Founder of Vimeo, CollegeHumor.com, BustedTees, and TeePublic. His entrepreneurial career began with the founding of CollegeHumor.com in 1999. Notably, his groundbreaking venture attracted significant attention, evidenced by a compelling $9 million offer before he completed college. This pivotal moment set the stage for a series of impactful endeavors, including the creation of Vimeo and BustedTees.com, culminating in their acquisition by Barry Diller’s IAC/InterActiveCorp for a reported $20 million in 2006. Josh stayed on with Diller for a short period and then left to start TeePublic.
With Josh’s leadership and entrepreneurial insight TeePublic grew to $41 million in revenue and $4.5 million in EBITDA before he decided to sell to RedBubble for $41 million.
In this podcast episode we walk through the ins and outs of Josh’s story, and he will shine light into mistakes to avoid as an entrepreneur and more!
We discuss:
- Structuring deals when selling to a public company and risks to avoid
- Weighing decisions on when to sell
- Negotiations with potential acquirers
- How to navigate what life looks like after a big exit
Additional Resources:
- Access our archive of video interviews on YouTube
- Checkout our upcoming Conference – https://malaunchpad.com/
- Get in touch with show hosts Casey Minshew and Feras Moussa at – info@equitylaunchpad.com
- Looking to invest in M&A opportunities or partner with an advisor to acquire, scale or sell your business? Visit Equity Launchpad
Transcript
00:00 all right on today’s episode we
00:01 interviewed Josh Abramson some of you
00:03 know Josh is the founder of college
00:05 humor Vimeo or buses brands that many of
00:08 us are familiar with and really a wealth
00:10 of information so on today’s episode we
00:12 talked about what you start with may not
00:14 be the same thing you finish with and
00:15 how to diversify in a business journey
00:17 in addition to that we also talked about
00:19 how to leverage things available to you
00:21 in your journey to help avoid boiling
00:23 the ocean and taking on too much risk
00:25 and last but not least we talked about
00:26 what it looks like to sell to a billion
00:28 dollar company how to mitigate risk and
00:29 some of the that he faced in that
01:31 Journey Casey tons of information where
01:33 some of your big takeaways multiple
01:35 exits he was a startup guy he got a
01:37 chance to do his own acquisition and he
01:39 was able to get a really big exit very
01:42 humble solid gentleman I was very
01:43 impressed awesome so excited about this
01:45 one so let’s hop right
01:49 in on today’s show we have Josh Abramson
01:52 he’s an American entrepreneur and
01:53 co-founder of the comedy website college
01:55 humor which I grew up on he was one of
01:57 the principal owners and founders of
01:58 connect Adventures whose properties also
01:00 include Vimeo busted te’s and the
01:02 co-founder owner and CEO of the
01:04 crowdsource T-shirt design company tuu
01:07 Josh welcome to the show thank you
01:08 thanks for having me great to have you
01:10 Josh yeah I know I’m excited to have you
01:11 on like I said I’ve heard your story a
01:13 few times so was exciting to kind of
01:15 have you participate on the show and
01:16 really learn a little bit more about the
01:18 mechanics of what happens right
01:20 everybody sees websites everybody
01:21 interacts with things but most people
01:23 don’t realize the proof in the pudding
01:24 and kind of how what it takes to make
01:26 the sausage and so you know with that
01:28 said I guess wanted to hear a little bit
02:30 about how’ you get started yeah so I got
02:34 started in 1999 I was a freshman in
02:37 college I went to school in Virginia my
02:40 best friend from high school and I you
02:42 know we did some like entrepreneurial
02:44 stuff when we were in high school but
02:46 you know super small level like you know
02:48 we would DJ the school dance and that
02:51 sort of stuff just trying to figure out
02:53 ways to make money that were a little
02:54 bit unorthodox um so when we got to
02:57 college we were kind of you know
02:59 shooting around ideas for ways to start
02:01 a business um had the idea to start a
02:04 website that was you know Advertising
02:07 based and you know saw some of these
02:10 businesses that were you know becoming
02:12 popular in that point in time um and we
02:16 were kind of you know going back and
02:18 forth on like what would that be like
02:19 how do we get people to come to a
02:21 website so that we can then put ads on
02:23 the website and make money um so we had
02:26 a couple bad ideas and then um one of
02:29 the things that was unique about
03:30 starting College in 1999 was that um
03:34 most people didn’t have high-speed
03:36 internet before they got to college at
03:38 that point in time and then they got to
03:39 college and all of a sudden you have a
03:41 brand new computer you have high-speed
03:43 internet and you’re surrounded by you
03:45 know tons of people so um it was a
03:48 really interesting moment for the
03:50 internet and for you know young people
03:52 who were sort of just becoming like Avid
03:55 web users so uh be you know this was
03:57 obviously many years before Facebook and
03:60 you YouTube and and websites like that
03:02 so the way that people were sharing
03:04 funny videos and pictures and that sort
03:05 of thing was really peer-to-peer you
03:08 know people would have their computer
03:09 signed up to the youd send the thing off
03:12 I all so that was really the idea was
03:17 let’s take all of the stuff that’s kind
03:18 of floating around the dorm rooms like
03:20 quite literally and just put it on a
03:22 website and then direct people to that
03:25 website and see if we could make it grow
03:27 and that was how kge schimer was born um
03:30 and that was again late
04:32 1999 um it was sort of you know crazy
04:36 for us at the time because it really GRE
04:38 quickly and um and it was you know from
04:43 like idea to like getting big checks
04:47 every month was like you know three
04:49 months um and that just felt insane so
04:53 well let me pause you there really quick
04:55 I got to ask you a question because you
04:56 know I went to college in 2005 so I’m a
04:58 few years behind you but again same
04:59 generation grew up from basically no
04:01 phones to phones from you know dialup to
04:04 DSL and similar to you I was I was an
04:06 internet entrepreneur at the time I had
04:08 kind a few different companies and the
04:10 one thing and I still remember pre
04:12 youube right because I actually looked
04:14 at building something similar to YouTube
04:15 and I remember scraping College Humor
04:17 Once Upon a Time and built my own
04:18 database of all of the same stuff what
04:21 gave you the confidence around the
04:22 server hosting cost because that was
04:24 always you know to me at the time and I
04:26 was still kind of young and naive and it
04:27 it was really expensive to host that
04:30 kind of content and so especially 1999 I
05:32 was looking at it 2002 2003 where even
05:35 then I was still I didn’t think the
05:36 economics worked and so what gave you
05:38 that confidence and what you know how
05:39 did that work back then this is a little
05:41 bit internet lore for those people on
05:43 the show yeah I mean so what was unique
05:46 about that moment in time is it was
05:48 pr.com Bubble Burst so there were ad
05:51 networks that would host your website
05:53 for free so you know there was one
05:55 called Blah Blah for example that went
05:58 under you know probably by the time you
05:00 started college but in 99 they were
05:02 going strong and you would literally
05:04 just put your website on their hosting
05:07 platform and then um they would put
05:10 banner ads on the top and bottom and you
05:12 would make you know a couple dollars CPM
05:15 for as many pages as you could possibly
05:16 generate and nobody was really super
05:19 sophisticated in terms of you know
05:21 conversion you know tracking and that
05:23 sort of thing so we were incentivized to
05:26 just get as many Pags as possible and
05:27 the more Pags we got the bigger check we
05:29 got at the end of the so it kind of
06:31 seemed like almost too easy and it was
06:34 um obviously that model did not continue
06:36 to exist for too long um but we started
06:39 right at the the perfect moment for that
06:42 because we started to get traction and
06:44 started to build confidence in the
06:46 business before the bubble bursts and by
06:49 the time it did we’d already made a
06:51 little bit of money and um and that was
06:54 actually you know when I think of when I
06:56 started to really come into my own as an
06:58 entrepreneur and like really
06:59 understanding how you know people on the
06:03 internet sort of you know how you can
06:05 actually make money on a website that
06:07 really came um in 2001 after the bubble
06:11 had burst and then those deals were no
06:14 longer there both from you know the
06:15 advertising deals were not there and the
06:17 free hosting wasn’t there so we actually
06:19 had to pay for our own hosting we had to
06:20 figure out how to sell ads um and that’s
06:23 when it got really hard but that was
06:24 also when it got exciting and that was
06:27 what led me to start to understand you
06:29 know how do you take an audience and
07:31 send that traffic towards a website to
07:34 get them to actually buy something and
07:35 and take a percentage of that or you
07:38 know selling ads to you know whatever at
07:42 the time it wasn’t brand ads because we
07:44 didn’t you know we hadn’t cracked that
07:45 nut yet but we were doing a lot of you
07:48 know conversion based stuff so like
07:50 selling posters selling funny t-shirts I
07:53 remember all posters.com I actually made
07:54 a lot of money on all posters like I
07:56 said I was kind of a slightly different
07:58 variation of what you had done yeah so I
07:00 mean we tried all sorts of stuff and all
07:03 posters was one of the best Affiliates
07:06 that we had and then we had a couple
07:08 t-shirt websites at the time that were
07:10 paying us a lot of money so that was how
07:13 the idea for bust toes.com came around
07:15 which was you know why don’t we build
07:17 our own e-commerce business and we can
07:19 use the traffic from College Humor to
07:21 you know generate Revenue through that
07:23 um and you know selling posters and
07:26 making posters was harder than making
07:28 t-shirts so that’s why we decided to do
08:31 t-shirts um the path of lease resistance
08:34 was off in the way in those days um so
08:37 that was how you know we started doing
08:39 e-commerce and then for a little while
08:42 by this point I graduated from college
08:44 and was really you know we were just
08:47 trying to build as much stuff as we
08:48 could and we were you know somewhat
08:51 focused on College Humor but also
08:52 focused on trying to build other things
08:54 so we built a you
08:56 know a social networking site for
08:59 college kids before Facebook that didn’t
08:01 really work um we built still remember
08:03 the r out of their strategy right it’s
08:04 all about strategy but really quick I
08:07 guess what was the revenue at and
08:09 expenses at at the time you were
08:10 graduating college from College
08:12 Humor so by the time we
08:15 graduated we were I think at the time
08:18 when we
08:20 graduated we we basically were making
08:23 the same amount as like a really high
08:26 paying job out of college so I I
08:29 actually can’t remember EX what our
08:30 Revenue was but I remember like when we
09:32 decided we were going to do it fulltime
09:34 we knew that we would be able to make
09:36 call it like $60,000 a year um so that
09:38 was sort of you know call it like
09:41 sometime during our senior year of of um
09:44 of college and then by the time we
09:45 graduated the business had continued to
09:47 grow and then that next year it really
09:49 grew so we ended up you know making
09:51 quite a bit more than that but that was
09:53 sort of you know once we got to that
09:55 threshold that gave us the confidence to
09:57 like not take an actual job um but you
09:02 know in that following year we launched
09:04 the t-shirt business and the t-shirt
09:06 business within a couple months was
09:07 making us more money than the college
09:09 humor business so then we started
09:11 focusing on that and then right around
09:14 that time we kind of finally figured out
09:17 I think the first Big Brand that I ever
09:19 sold advertising to was Toyota and
09:22 learned pretty quickly that you know I
09:24 can sell something to Toyota for
09:26 $440,000 that I would only be able to
09:28 sell for $4,000 to you know somebody
10:31 who’s focused on you know generating
10:33 conversions so that was when I started
10:35 to really understand how brand
10:37 advertising works and then once we
10:39 started to crack the nut on that and the
10:40 klege humor business you know started to
10:43 overtake um the t-shirt business very
10:45 quickly and that was when it started you
10:47 know right around them we moved to New
10:49 York City and then everything got really
10:51 crazy very
10:53 quickly now let me ask you about this
10:56 Josh is your family are yall
10:58 entrepreneurs like did you grow up in a
10:60 family of entrepreneurs or were you like
10:01 kind of the first one to to get this
10:03 creative just to go out and do um my
10:08 father ran companies so he and I guess
10:11 you could call him an entrepreneur
10:12 although I don’t know that he identifies
10:14 that way but um he you know when I was
10:17 really little he owned a juice company
10:19 so they would bottle juices and it it
10:21 was very different from the type of
10:22 business that businesses that I’ve had I
10:25 mean you go in and it’s like huge
10:26 stainless steel tanks and warehouses and
10:29 like Giant freezers and refrigerators
11:31 and you know it was like a very um it it
11:34 was a factory basically so I I grew up
11:36 seeing that um but you know the sort of
11:42 interesting thing to me about the
11:43 internet was you know even as early is
11:46 like you know when I first started
11:47 selling things on eBay or just you know
11:50 understanding that you could actually
11:51 make money just sitting at your computer
11:53 there was something very appealing about
11:55 that um and just the idea of having I
11:59 will I will admit first money I made
11:00 online was selling items on Diablo I and
11:02 I don’t know what I was thinking as like
11:03 a seventh grader giving some random
11:05 person my home address but I did and the
11:07 guy mailed me cash and you know he kept
11:09 on doing it for years so it’s definitely
11:11 some crazy times to to quickly just tie
11:14 it together because you just you kind of
11:15 unpacked a lot so I want to make sure I
11:17 understood it and the audience
11:18 understood it too so you went from
11:20 really leveraging an existing platform
11:22 they did all the hosting all the cost
11:24 and even did even all the ad sales for
11:25 you right you were just really focused
11:28 on kind of the the community so to speak
12:30 or the messaging right you know the
12:32 product which is called humor then that
12:34 went out you had to kind of go build it
12:36 up yourself and now you’re like holy cow
12:37 There’s real cost you know we have to
12:39 figure how to make this profitable right
12:41 and so then that led to just doing
12:42 affiliate marketing such as all posters
12:45 and I guess at that same time you had
12:48 higher expenses so then you shifted and
12:49 said hey we’re going to go build kind of
12:52 this this this t-shirt business right
12:54 and mimic what all posters did and I am
12:55 curious if all posters are still around
12:57 because I they were such a monster at
12:59 the time but anyways mimic that model in
12:01 t-shirts right you got a little bit of
12:04 traction there and I think it sounds
12:06 like you learned and you started
12:07 focusing more on that and then you learn
12:08 about selling to Brands and shifted
12:11 Focus back onto college humor while
12:13 you’re doing both simultaneous is that
12:14 right did I get it all correct yeah
12:17 that’s pretty accurate I me by the time
12:19 we moved to New York City it was July of
12:22 2004 and the next six months were really
12:26 pretty wild because suddenly uh you we
12:30 moved to New York City we were meeting
13:31 all sorts of amazing people very quickly
13:33 people who had started companies that we
13:35 you know read about and they wanted to
13:37 meet us and that was really fun we never
13:39 had that experience and then you know
13:42 pretty soon after that we started to
13:43 have you know the bioms and news corpse
13:46 of the world reaching out and and
13:48 expressing interest in buying the
13:50 company which um just had never even
13:53 occurred to me that we’d be able to sell
13:55 the college humor business for some huge
13:57 amount of money I remember somebody um
13:60 well specifically it was Nick Denton who
13:02 you know was the um founder of Gawker he
13:05 was telling me once that he thought our
13:07 business was worth $20
13:09 million which was like crazy you know if
13:13 you would asked me what I thought it was
13:14 worth I would have said a tiny fraction
13:16 of that and I think he was right but it
13:18 just didn’t even occur to me you know
13:20 it’s you look back and you know you sort
13:22 of take it for granted that you know
13:24 when you’re 23 you know a lot of these
13:26 things that might seem obvious to us now
13:28 are not so um so we moved to New York
14:32 and I think so much of the attention
14:33 that we were getting was focused on
14:35 College Humor um that it made it easier
14:39 to just kind of go all in on the college
14:41 humor business um even when you know
14:45 later in 2004 my business partner Jake
14:48 gladwick invented Vimeo in our office
14:51 and you know it was difficult because at
14:55 that point we were really focusing on
14:57 College Humor we’ had these other side
14:58 projects which you know the t-shirt
14:00 business was nice we had the sort of you
14:03 know the social networking thing was not
14:06 working so we sort of you know put that
14:09 to the side and then this new business
14:11 Vimeo comes about it’s like all right
14:14 well this is cool but we don’t have
14:16 unlimited resources um and I think
14:19 perhaps most importantly there was the
14:21 issue of copyright infringement and you
14:23 know college Scher was in the business
14:25 of using user generated content to
14:27 generate page views right and as a
14:29 result of that as you can imagine we
15:31 would occasionally get cease and desists
15:33 we got sued once or twice that was
15:35 really stressful um and you know when
15:39 Vimeo first launched and this was before
15:41 YouTube um you know the idea of people
15:44 uploading copyrighted material and sort
15:46 of a free-for-all I just all I saw were
15:49 the the legal bills um and as a result
15:53 you know put a lot of throttles on Vimeo
15:56 um you know kind of pushed for everybody
15:59 to f focus more on College Humor sure
15:01 enough you know YouTube launches a
15:03 couple months later and for a while
15:05 we’re neck and- neck in terms of
15:06 audience um I one of your first users
15:09 yeah yeah I remember loading videos on
15:11 VI in the mortgage business I was in the
15:14 mortgage business and we were putting up
15:15 content and there was just not a lot of
15:17 ways to get stuff up and that was it
15:19 that was that was one of your options
15:20 now and I remember like I had built a
15:22 clone of YouTube and Just again it goes
15:24 back to the legal risks and then the
15:26 hosting risk like both of those things
15:27 and at the time it was crazy to think
15:30 about building a business that can stay
16:32 not profitable for so long right with
16:35 that’s the problem you have to I was way
16:37 too young to understand that right and
16:40 that’s the that’s the whole business
16:41 model for YouTube right now obviously
16:43 it’s a very profitable business but at
16:44 the time I mean you have to look at it
16:46 there’s you know legal stuff are never
16:48 fun right and again we’re kind of this
16:49 is the important stuff that most
16:51 business owners don’t think about
16:52 getting sued is very very common if
16:54 you’re in business long enough you will
16:55 get suits and you know we deal with
16:56 those all the time right those happen
16:58 for a variety of reasons those are
16:59 always stressful and then in addition to
16:01 that just kind of does the business work
16:03 does it not should you continue to
16:04 double down or not and you know in the
16:06 Vimeo or the YouTube’s back in 2004 2005
16:09 I mean it was a model that really
16:11 shouldn’t have made sense right and and
16:13 but but question for you really quick
16:16 tell me what did the business look like
16:19 at 2004 or five and what I mean by that
16:20 is like what was the org right what did
16:22 you have teams doing you know around is
16:25 it a team focused on selling ads a team
16:27 focused on getting content team that’s
16:29 out there doing you know physical
17:31 promotion I mean what did the team look
17:32 like how many people was it at the time
17:35 and what were they focused on so by the
17:38 time we started Vimeo there was a period
17:41 where we had College
17:43 Schumer um our you know social
17:46 networking dating site we thought social
17:48 networking was more for dating at the
17:50 time so me calling it a social
17:51 networking site is a little bit um
17:53 revisionist history but that was sort of
17:55 what it was we were building that we had
17:57 our t-shirt business we had started
17:59 another t-shirt business that was a
17:01 little bit more fashion forward um and
17:04 of course College humer and Vimeo and I
17:06 think there were four of us doing all of
17:08 that at that time um so I don’t know I
17:12 had this yeah I had this idea which was
17:17 you know flawed at the time but for
17:19 whatever reason I was very reluctant to
17:21 hire people um I think I was just overly
17:25 cautious I’ve always been pretty
17:26 conservative just with how I think about
17:28 you know businesses and profitability
17:30 and and all of that type of stuff so I
18:33 think as a result of that um I really
18:36 waited a long time to hire people and
18:39 then the first few people that we hired
18:41 we hired um an engineer that proved to
18:44 be hugely impactful we hired an editor
18:48 somebody to help us on the editorial
18:50 side that was really helpful um and we
18:52 hired somebody from um Maxum magazine at
18:56 the time um to help with branded ad
18:58 sales we figured that that was like a
18:60 pretty good
18:03 um yeah so so that was sort of like the
18:06 core initial team um and of our business
18:10 partners you know I had my business
18:11 partner that I started the company with
18:12 Ricky vanine who was really more um on
18:15 the editorial side and and the you know
18:18 the content and that sort of thing um
18:21 our partner Jacob who invented Vimeo and
18:25 was a coder he was our only engineer and
18:28 then um um the most the last partner to
19:31 join his name was Zack Klein and he was
19:33 a designer and product guy so between
19:35 the four of us we sort of had everything
19:39 kind of covered but just not a lot of
19:41 coverage um so you know by the time when
19:45 we eventually sold the company in 2006 I
19:48 think we only had about 15 people or 16
19:51 people and I think the business that
19:54 year made about $3 million on $6 million
19:58 in Revenue
19:00 um so you know it’s small but profitable
19:04 and what’ youall sell it for for those
19:06 listeners so we sold it for we sold 51%
19:11 for $20 million and then $414 $40
19:15 million-ish valuation on the whole thing
19:17 right basically yeah and um basically
19:20 what is that 8X
19:22 Revenue um yeah I mean it was a little
19:25 tricky because the there was the media
19:26 business that was at a higher multip and
19:29 then the Commerce business which was at
20:30 a lower multiple um and I forget what
20:33 those were exactly but the
20:37 um you know it was also you know I would
20:42 never advise anybody to sell 51% of
20:45 their company but um again we were young
20:48 and a bit naive
20:50 and how how old were you at this point I
20:54 had just turned 25 so what is that
20:57 process like for 20 it sounds like
20:58 you’re part were around the same age yes
20:01 yep what’s that process about thinking
20:03 about
20:04 selling someone gave you they would give
20:06 you a $20 million offer
20:09 right what what’s that
20:11 like um well so I had an offer to sell
20:14 the business in 2000 or 99 or 2000 um
20:18 for $9 million when we had just started
20:21 and um didn’t take it in part because it
20:26 was unclear how much of that money we
20:27 would actually get based on how was
20:29 structured but i’ sort of you know like
21:32 that was before the Doom Bubble Burst
21:34 right so I’d had that experience of sort
21:37 of thinking about it a little bit um and
21:41 then you know fast forward to when we
21:44 had real companies trying to acquire us
21:47 that really started in Earnest in 2005
21:50 and it’s because um you know some people
21:53 from MTV networks had reached out to us
21:56 and um you know we just started having
21:59 conversations and we weren’t really sure
21:01 what those conversations were and then
21:03 you know the guy in the room is you know
21:05 gives us his business card and it’s you
21:07 know Executive Vice President of mergers
21:08 and Acquisitions we’re like okay well
21:10 like maybe they want to buy our company
21:12 so um we went through a super robust due
21:17 diligence process with um with Viacom to
21:21 the point where again just being naive
21:23 and young I was basically telling
21:25 everybody I knew that I was selling my
21:27 company to to BU aom because I thought
21:29 that it was a done deal basically um and
22:32 after spending many months on the deal
22:35 they ultimately just decided they didn’t
22:36 want to do it so that was late 2005 but
22:40 in the process of doing that we brought
22:42 on Allen and Company to help us with the
22:44 sale um and we also you know went
22:48 through the process with news
22:50 corporation which didn’t end up working
22:53 out either so by the end of that year we
22:56 were kind of like you know I guess we
22:58 just have to go back to work like those
22:00 deals didn’t happen um so then you know
22:04 in the New Year early in January we kind
22:06 of we went out and someone had told me
22:09 about the idea of doing a secondary
22:11 round and suggested you know maybe you
22:13 go to you know someone in private Equity
22:16 or you know figure out a way to take
22:18 some money off the table so you can keep
22:20 building the business and not have to
22:21 worry about selling it so we went out
22:23 and and got a couple of term sheets to
22:25 do a deal that looks like that um and
22:29 right around that same time IAC reached
23:32 out to us and said you know they were
23:34 starting a new programming Division and
23:37 wanted to buy the business so that all
23:40 kind of you know came together pretty
23:42 quickly um and I think at the time I was
23:45 thinking of you know because we were
23:48 really having a fun you know it was like
23:50 it’s still probably the most fun thing
23:51 I’ve ever done blast and um so the idea
23:55 of selling the business you know we
23:56 really thought that there was a lot of
23:58 Runway left and we wanted to continue
23:60 working on it you know again we were
23:02 super young and we were having a good
23:03 time so the idea of selling 51% was
23:06 appealing because in my head you know we
23:10 still had a lot of upside um we figured
23:13 you know if it’s a home run and we can
23:15 you know we had a a put call Arrangement
23:18 so that we could you know force them to
23:20 buy the remaining 49% at certain points
23:23 down the road so it felt like we were
23:25 pretty well protected in the case of you
23:28 know big upside um and we were
24:31 mitigating our downside because we’re
24:33 taking a lot of money you know more
24:34 money than I thought I would ever maybe
24:36 make in my life you know off the table
24:38 um you know at 25 so that it all made a
24:41 lot of sense now the way that it
24:43 actually played out you know ended up
24:46 being a bit different than that and I
24:47 think you know one mistake that I think
24:49 a lot of people make in advice I give
24:52 just in any deal really but especially
24:54 something like this is I think people
24:55 tend to focus on the worst case scenario
24:57 and the best case scenario
24:59 um obviously if it’s you know the worst
24:02 case scenario the business dies you know
24:04 3 days after you sell it like that’s
24:06 fine like you at least you sold half if
24:08 it’s like an absolute home run and you
24:10 build the next Google and you sell the
24:12 other 49% and you make a billion dollars
24:14 like that’s awesome too but rarely is it
24:18 either of those two things it’s almost
24:19 always something in the middle um so I
24:22 think you know uh that was certainly the
24:26 case with us in hindsight we sold a
24:29 niche content business to a big public
25:32 company two years after Facebook and
25:35 YouTube were started right so like the
25:37 the world was changing and we were
25:40 inevitably going to get swallowed up
25:42 know I mean right place right time
25:44 because I mean every I remember every
25:45 Media company was trying to figure out
25:47 what does their online presence look
25:48 like right they needed to check that box
25:50 and people are actively looking and
25:52 unfortunately right like a lot of
25:54 sellers you get tunnel vision right
25:55 you’re F okay there more money than I’ve
25:56 ever made in my life and like you said
25:59 here’s what the worst case here’s what
25:60 the best case looks like but nine times
25:01 out of 10 status quo is what happens
25:03 right so what does status quo look like
25:05 and you know you you were almost if you
25:07 really think about it right if you think
25:09 about like the dig at the time and the
25:10 reddits right you were kind of that
25:13 Community right there’s content that
25:14 people are viewing and commenting on and
25:16 sharing and you know if you had the
25:18 ability to kind of make it your own who
25:20 knew who knows where it would have gone
25:21 right in the long term and so but again
25:24 that’s the that’s the risk of of selling
25:26 and you know you everybody wants to go
25:28 get that secondary round get liquidity
25:29 off the table and you know it comes with
26:31 I guess the territory you also I mean
26:34 you know Barry Diller has a reputation
26:36 of being a challenging person to work
26:38 for and you know for someone like me who
26:41 you know I wasn’t like a Wharton MBA you
26:44 know worked in finance for five years
26:47 whatever like you know I was a pretty
26:49 Scrappy entrepreneur who was used to
26:51 doing things the way that I knew how to
26:53 do them and all of a sudden now I’m
26:55 reporting to this like iconic
26:57 multi-billionaire who’s like really you
26:60 know uh can be difficult and likes to
26:02 yell and like it’s it was very
26:04 intimidating um and that was you know I
26:08 didn’t enjoy that um I’m not you know
26:11 there are some people who really thrive
26:12 in that environment I did not so I think
26:16 you know you’re now like running this
26:19 business which you know ultimately
26:21 whenever there’s a really big decision
26:23 it’s not your decision you learn that
26:25 pretty quickly and then you know you
26:27 have half of your worth tied up in a
26:29 business that you don’t control and
27:31 you’re kind of you know tied to it so um
27:34 so that you know the first couple months
27:36 or first year or so after the deal was
27:39 was great and then the wheels started to
27:42 fall off a little bit year two and by
27:44 year five you know by the time I left I
27:46 was like very ready to not do that
27:49 anymore no I mean I’ve heard that from
27:51 many people time and time again right
27:53 because whenever you go into it the
27:54 people that are there are a lot of times
27:56 very different three years later so the
27:58 people that supporting you or supporting
27:59 the vision saw where it can go you know
27:01 they moved up they moved out they move
27:03 they went elsewhere and now you have a
27:05 different person who maybe doesn’t have
27:06 the same vision of where to take that
27:08 company from kind of a from a corporate
27:11 leadership perspective yeah and I would
27:13 imagine you’re going from being a
27:14 full-fledged entrepreneur you know
27:17 whiteboarding doing whatever you guys
27:19 are doing and now you have a control
27:22 that kind of take kind of squeezes a lot
27:23 of that creativity I I at least would
27:25 imagine that’s probably how you felt for
27:27 sure there was that and there was also
28:30 you know the thing that I think about
28:32 the most during those days is you know
28:34 you go into these board meetings and
28:35 you’re
28:36 presenting um you know your plan and and
28:39 the things you’re working on and across
28:41 the table from me are you know guys you
28:43 know at least twice my age if not more
28:46 so um you know smarter more experienced
28:50 you know all the things but they don’t
28:52 understand my business as well as I do
28:54 or I don’t think that they do I don’t
28:55 think that they did um but that was sort
28:58 of you know beside the point you know
28:00 you you walk in and all of a sudden you
28:02 have these very intimidating guys poking
28:05 holes and everything that you’re saying
28:07 and you know you would walk out of those
28:09 meetings having signed up for a site
28:11 redesign or some shift in strategy that
28:14 you really didn’t believe in but you
28:15 weren’t able to argue it you know you
28:18 couldn’t be articulate enough in the
28:19 moment and you’re nervous and like you
28:21 know there was one time I was getting
28:22 yelled at and like I felt myself like
28:24 almost about to cry you know I was like
28:26 getting it was so emotional it’s I
28:27 wasn’t equipped for that um I didn’t
28:30 have the Reps to you know be able to
29:32 fight back in those circumstances nor
29:34 did I have the confidence um and things
29:36 weren’t going as well as we had
29:37 projected that they would so the
29:39 combination of all those things you know
29:41 makes it very difficult to be successful
29:44 I think no I mean I I used to work at a
29:46 Microsoft I used to work at Microsoft
29:48 and one of the biggest things you learn
29:50 early on is how to find your voice right
29:52 you’re in a room a lot of smart people a
29:54 lot of people that can you know chew you
29:56 out and it’s easy just to kind of be the
29:58 push over and whenever you have to make
29:60 big business decision impacts big big
29:02 impactful business decisions you have to
29:04 find your voice and that’s one of the
29:05 biggest things that you know in our
29:07 company we’re trying to coach people up
29:08 like speak up right like don’t hesitate
29:10 to give your opinion tell the person hey
29:13 no I’m I don’t think that’s the right
29:14 decision and here’s why and it’s okay
29:16 and I think that’s one of the biggest
29:18 mistakes most entrepreneurs do right is
29:19 they’ll grow grow grow get something but
29:21 then kind of lose their way for a
29:23 variety of reasons on that y so yeah so
29:26 snapshot so now you so you were 25
29:28 you’re there for five years so you had
29:29 your exit you’re there five years and
30:32 then what happens at that point you
30:34 decide to leave and then what what goes
30:36 from there because I’m sure you took a
30:38 tremendous amount of learning experience
30:39 from all of that so then for sure the
30:43 benefits are great so you know if you
30:46 recall the three businesses that we sold
30:48 was was college humor busties and Vimeo
30:50 pretty soon after the acquisition Barry
30:53 Diller decided in one of our meetings
30:54 that he wanted us to shut down the
30:56 t-shirt business and at that point the
30:57 t-shirt business was making over a
30:59 million dollars a year in profit and
30:00 really without much of anybody’s effort
30:04 um so he he basically was like Jos I
30:06 don’t want you to spend a second of your
30:08 time on this business and if it you know
30:11 if it deteriorates like we’re going to
30:12 shut it down so it’s basically like
30:14 which is also frustrating right when you
30:16 own 49% of a business that makes a
30:18 million dollars a year and someone tells
30:19 you they’re just going to kill it
30:20 because they don’t want to think about
30:22 it like that was annoying um so you know
30:26 it kind of I can’t remember exactly but
30:28 it started percolating a little bit in
30:30 the back of my mind that like maybe
31:31 there was a way I could buy that
31:33 business out of IAC or take it because I
31:35 thought it was a really fun business um
31:39 and you know during the five years that
31:41 I was there we had to renegotiate our
31:43 deal a couple times because we bought a
31:45 production company that required some
31:47 capital and like there were all these
31:49 things and usually when you’re
31:51 negotiating against a company like that
31:53 you don’t get the better end of the deal
31:56 especially when they control your
31:57 business so um we ended up having to put
31:01 uh or push our put option out a couple
31:03 more years and you know we did get um a
31:05 nice employment agreement and you know
31:07 some increased compensation that sort of
31:09 thing so I was now sitting in a
31:11 situation where you know they had to pay
31:13 me for a couple years regardless of
31:15 whether I showed up or not unless you
31:17 know if they fired me they had to pay me
31:19 too so um you know at that point we
31:23 decided sort of collectively that we
31:24 were going to hire a CEO for college
31:27 humor and it wasn’t going to be me me um
32:30 and it was just clear that you know I
32:32 wasn’t it didn’t really make sense for
32:33 me to stay there any longer um but you
32:36 know they would have had to continue
32:38 paying me and I sort of LED them to
32:40 believe that I was happy to you know sit
32:43 in my office for the next couple of
32:45 years and not do anything um and just
32:48 get paid or they could give me all of
32:51 that money that they owe me um and some
32:54 of the stock grants that I’d had in the
32:57 form of this business that didn’t want
32:60 and um and everybody was super fair
32:02 about that transaction actually I think
32:04 because they didn’t want it it was not
32:06 thought it was a great
32:07 deal yeah so so um so that again that
32:11 was five years after i’ sold a business
32:14 um and then I you know May 1st 2011 I
32:19 put my pencil down um you know was my
32:22 last day at IAC and my first day of the
32:25 sole owner of the buses business so
32:28 um so right around then you know and at
33:31 that point in time I had like a floor to
33:32 ceiling glass corner office with like a
33:35 mini fridge with like coca-colas or
33:38 whatever that got like perfectly
33:39 arranged in like pencils that someone
33:41 sharpened every night you know it was
33:43 like a pretty fancy setup and then fast
33:47 forward like a month and we’re now in
33:49 like a very dingy Loft um in flat iron
33:54 with like a mouse problem and I was I
33:56 couldn’t have been happier well ask
33:58 whenever you were in the fancy corporate
33:60 office were you wearing a suit or no
33:02 that’s just the no it was we all dress
33:05 pretty casually you know you could kind
33:07 of tell the people who worked at
33:08 corporate because they all had you know
33:10 sort of business casual but you know we
33:11 were mostly wearing t-shirts and jeans
33:14 um but you know it never really felt
33:17 like once we were in the IC building it
33:19 never really felt like my home it felt
33:20 like we were working in like a big
33:22 company and I think a lot of people felt
33:25 the same way it just you know was no
33:27 longer our space
33:29 um so when I bought back the t-shirt
34:31 business I think there were six people
34:33 including myself so small team um but it
34:37 was a great team and everybody you know
34:39 got along really well and we all% owner
34:41 you’re 100% owner nice yep so all of a
34:44 sudden I own this business which I was
34:46 now making more money like on day two as
34:49 the owner of this new business than I
34:51 was making from salary from I and I
34:54 owned a company that was mine um so real
34:57 quick two so what did the business cost
34:60 you you know obviously it’s kind of
34:01 complicated because you accelerated
34:03 things you changed things what do you
34:04 what would you say it cost you and then
34:06 on top of that what was it actually
34:08 making day two so I think it was it was
34:12 basically three times eida plus the
34:15 value of the inventory so that you know
34:18 iida that year was like
34:20 $650,000 and then there was a couple
34:23 hundred thousand in inventory so it was
34:25 about $2.5 million that the business
34:28 cost but cash out of pocket was only you
35:31 know I think it was like
35:33 $250,000 out of pocket because the rest
35:35 was just money that they owed to me in
35:38 one way or another so that made it a lot
35:40 easier to swallow versus like having to
35:43 write a check that big that’s your first
35:45 acquisition that’s that pretty fantastic
35:48 yeah so it was it was great and then I
35:51 hired somebody to help me run the
35:53 business who ended up becoming a great
35:55 partner and helped me build my next
35:57 business um but you know we all of a
35:01 sudden it just felt fun again you know I
35:03 lost so much confidence being at IEC and
35:06 you know after selling a business and
35:08 then you know having it not work as well
35:10 as you would hoped that it would you
35:12 start to question your abilities and you
35:15 know I definitely had periods of you
35:17 know years really where I was like well
35:19 maybe I just had this one like you know
35:22 one little success or whatever you know
35:24 scale success um and that was it and I’m
35:27 not you know not actually that good at
35:29 this I just got lucky and it really
36:31 wasn’t until buying back that business
36:34 and being able to grow it and then
36:35 ultimately growing it into something
36:37 else that was even a much more
36:40 successful exit than the college humor
36:42 business had been um it took that for me
36:45 to feel confident again and realize okay
36:47 I know how to do this like I’m I’m not
36:49 an idiot even though you know Barry
36:51 Diller might think I am you know what I
36:54 love I love that you’re you literally
36:56 are the guy that he comes in and tells
36:57 you you do not R this business goes and
36:01 you’re like you know what screw you I’m
36:04 going to take this I’m going to I’m
36:05 going to buy it and I’m gonna take it
36:07 and I’m gonna grow it and I bet you that
36:09 was an internal motivation would would
36:10 you agree that like the day you took it
36:13 I’m gonna take this and make this great
36:16 there was definitely some of that I
36:17 think there was also a bit of you know I
36:21 remember there’s a guy who I know a
36:22 little bit who um right after I stopped
36:25 working at College Schumer and started
36:27 doing the the T thing I was at a party
36:29 and he came up and he was like I forget
37:31 how I put it but it was super
37:33 condescending it was basically like so
37:34 are you actually going to be able to
37:35 stay in New York City and raise your
37:37 family just with this t-shirt business
37:40 you know it was like you know you’re
37:41 doing this like it’s you know it’s like
37:43 a lemonade stand I think that was the
37:45 impression that I think a lot of people
37:47 had of it and College Humor you know
37:49 while it doesn’t really exist anymore
37:51 back in those days um in terms of you
37:54 know social credibility we were you know
37:56 we were getting invited to like all of
37:58 the cool things we were you know
37:01 constantly having very interesting
37:02 people reaching out wanting to meet us
37:04 like you know it felt very much in the
37:06 mix and that went away almost
37:08 immediately after I got out of that
37:09 business like you know nobody really and
37:12 I think it was also an
37:14 interesting you know lesson there there
37:16 were certain people who I realized you
37:19 know pretty quickly like oh those
37:20 weren’t actually friends there were just
37:22 like business contacts and that were you
37:24 know that wasn’t obvious to me I just
37:26 thought that I was like good friends
37:27 with these people and then all of a
37:29 sudden you know I’m reaching out and
38:30 realizing like they don’t want to get
38:32 lunch with me anymore you know so I
38:34 think there was a little bit of like you
38:36 know Screw all these guys you know
38:40 forget the naysayers so tell us about
38:42 this lemonade stand right what did it
38:43 you know you bought it what was the
38:45 revenue and where’d you get it to so the
38:47 busted teas business we got it to I
38:51 think it was like was a couple million
38:53 dollars when I bought it in revenue and
38:54 like I said it was about $600,000 in
38:56 evida and then pretty quickly we grew it
38:59 to $10 million in revenue and just over
38:03 a million dollars um in profit and right
38:06 about that time realized okay this is
38:08 just not going to grow like there’s no
38:10 more opportunities for paid acquisition
38:14 like it’s just you know this is I think
38:16 as big as this business can get unless
38:18 it just turns into something else and
38:20 and that was when I had the idea for tuu
38:22 which was you know basically eliminating
38:25 a lot of the hurdles that the busted
38:28 business had and you know for example we
39:30 would release 16 t-shirts every week at
39:33 our Peak for the busted te’s business
39:35 and some of them would sell really well
39:36 and some of them wouldn’t sell very well
39:38 and there’s a fixed cost to releasing
39:40 those you have to design them you have
39:41 to come up with the ideas and we were
39:43 taking inventory so there was an
39:44 inventory cost some of them wouldn’t
39:46 sell you’re sitting on excess inventory
39:48 so the idea for tuu was really to open
39:51 it up and to create you know more of a
39:53 an Open Marketplace so that we could
39:55 attract designers and allow them to to
39:58 contribute and and get a portion of the
39:00 revenue and um and print everything on
39:04 demand as opposed to um taking inventory
39:07 and On Demand printing technology had
39:08 just gotten to a point where that was a
39:10 viable business you know that was I
39:13 guess
39:13 2013 and you know we we built that
39:16 business and put everything we had into
39:18 it and then after the first couple
39:21 months it just was not growing at all um
39:24 so I think we launched it in like March
39:27 and by November despite all of our
39:30 efforts no growth just kind of
40:32 depressing and and not really not really
40:35 doing much I remember coming home and
40:37 telling my wife like I think you know at
40:38 this point I’d invested several hundred
40:40 thousand dollars of my own money into
40:41 building it and I remember telling my
40:43 wife I think we’re gonna have to shut it
40:44 down I just don’t think it’s working and
40:46 then the holiday season happened and in
40:49 that business the holidays were always a
40:51 huge lift um in terms of Revenue and
40:54 conversion and we had a pretty good lift
40:57 for the holiday season and then we we
40:59 made some tweaks to the model and and
40:01 you know how we were compensating
40:02 artists and you know just some some
40:04 little things that all of a sudden you
40:06 know by January um usually after
40:09 December there’s a huge drop off for
40:11 January but for the business that year
40:14 actually grew into January and then it
40:16 started growing 50% month over month so
40:18 I think the first year of tuu we did
40:22 maybe $300,000 in revenue and then the
40:25 second year we did five million wow um
40:27 and then it just you know kept going
40:30 there so it was and at that point it was
41:32 like all right well this is the business
41:33 that we need to focus on and the bused
41:35 business just became you know an
41:37 afterthought and frankly like you know
41:39 my my idea you know I wasn’t aspiring to
41:43 just have this busted tease business
41:45 when I bought it back I was really
41:46 thinking of it as you know a starting
41:48 point and hoping that I would find my
41:50 way towards a Better Business um which
41:53 is exactly what happened but it wasn’t
41:55 clear what that was going to be and that
41:57 was you know I think that’s sort of like
41:59 at least for for me as an entrepreneur
41:01 it’s it’s always sort of happened that
41:02 way where you kind of have to just like
41:04 you know I think of that like scene in
41:05 Indiana Jones where he’s got to like
41:07 walk across the like you know huge um
41:11 cave or whatever and like you can’t see
41:13 where you know you just have to like
41:14 believe that your foot’s going to land
41:15 in front of you but you have to kind of
41:17 take the step not knowing where you’re
41:18 going to actually step and I um I think
41:21 that was the case with that business for
41:23 sure you just got to cross the chasm
41:25 right that’s the phrase so it’s you know
41:27 and it’s fun how it typ how it works
41:29 like that right because you don’t in
42:31 hindsight some of these things are so
42:32 obvious right but living and you have to
42:34 like live and breathe the moment because
42:36 it’s it’s almost obvious to public in
42:38 hindsight right like of course that
42:39 makes sense right like why not leverage
42:41 you know the ecosystem let people do
42:42 their own thing but then it’s you know
42:44 at the time if you really put yourself
42:46 into that you have to have been doing
42:48 busted te’s to be able to evolve and
42:51 understand the gaps there and the issues
42:52 there and not only that you had to have
42:54 technology catch up because I remember
42:55 buying you know off of T public and at
42:57 the time I’m like man how can they just
42:58 print anything right like the technology
42:01 had to catch up the whole thing had to
42:02 tie together and you know lo and behold
42:03 you have a nice healthy business yeah
42:05 and I think you know every business that
42:07 I’ve started really was you know college
42:10 humor was the first sort of original
42:13 idea that I had in a vacuum where I was
42:15 like all right we need to start
42:16 something like let’s do this everything
42:19 else you know the t-shirt business was
42:20 born out of that you know Vimeo was
42:23 ultimately born out of that you know the
42:25 TU business was born out of another T
42:27 business you know a lot of these things
42:29 were like I wouldn’t have been able to
43:31 come up with those ideas were I not
43:33 already working hard on the previous one
43:35 and that was as we talk about the next
43:38 deal um you know when I when I sold the
43:40 TU public business that was really the
43:42 first time where I was totally putting
43:44 my pencil down and had nothing nothing
43:46 really happening what ultimately
43:48 happened to Vimeo so Vimeo was a super
43:51 frustrating story I guess I’ll just tell
43:53 you what happened so basically we sold
43:56 51% of Vio along with college humor and
43:59 busted teas shortly after our
43:01 acquisition we decided we wanted to
43:03 pitch Barry Diller on Vimeo and
43:05 investing more money into Vimeo and and
43:07 you know having a proper go at that
43:10 business so that was you know I guess
43:13 what 2006 2007 so we went we asked for
43:17 $2
43:17 million which he gave to us to go build
43:21 out a team so we built out a team of
43:23 about a dozen people and like really
43:25 like some of the best engineers and
43:28 talented people that I’ve ever seen you
43:30 know building software we really found
44:31 some excellent people um and built what
44:35 really is like the you know Vimeo that
44:37 you see today I mean obviously the
44:38 functionality changed since then but the
44:41 design and really the like the nuts and
44:44 bolts of what made Vimeo Vimeo was
44:46 created in that year um so we started to
44:50 see some growth and then ultimately part
44:53 of the issue with the way that our deal
44:54 was structured was we had a put call
44:58 that gave us the option to sell our
44:01 shares at a certain point in the future
44:03 and that was going to be based on fair
44:05 market value and you know we weren’t we
44:09 knew that IC wasn’t going to sell Vimeo
44:11 so for Vimeo to be valuable to us in
44:14 terms of our Equity you know it was it
44:16 was tricky right it was it was hard to
44:18 figure out how that was going to be
44:19 valued so the money that we were
44:22 spending was really our own money
44:24 because even though Barry gave it to us
44:27 it was just coming off of our balance
44:28 sheet so all the money that klege
44:30 Schumer was making was being just sucked
45:33 up by Vimeo so it started to become
45:35 clear that as Vimeo was losing more and
45:37 more money that and kge humor was not
45:40 growing as much as we had hoped you know
45:43 kimer we knew had value and we knew we
45:45 were going to sell the rest of it for
45:47 however many millions of dollars and
45:48 that was going to go to us Vimeo was
45:50 basically you know just like a series a
45:54 level you know high-risk startup with no
45:58 monetization path really like we tried a
45:01 couple things without success so we got
45:05 to a point where you know Vimeo was
45:06 losing a lot of money and we kind of had
45:09 a gun to our head to say like either you
45:11 continue financing it yourselves or you
45:14 know we’re going to like take it and put
45:15 it in a different part of IAC that was a
45:19 a tricky moment because you know on one
45:22 hand you know it was still an exciting
45:24 business and we were passionate about it
45:26 but it was losing so much money and
45:29 there was a very easy path to imagine
46:31 where it would lose so much money that
46:32 it would just wipe out everything that
46:34 we had an equity value for the business
46:37 so as a result we ultimately gave up our
46:41 Equity um in exchange for not having to
46:44 finance the the losses um and had you
46:48 know argued at the time to retain some
46:50 amount of equity um but we were not
46:53 given that equity which that part still
46:56 irks me a little bit because I think it
46:57 would have been fair for us Neo with a
46:00 billionaire got a little bit mean when
46:03 somebody you know uh you know when you
46:06 have leverage you know you’re meant to
46:08 use it so I don’t fault them for that um
46:11 I just regret being in a position where
46:14 I had such little leverage because also
46:16 you know you’re still working for them
46:17 and your your willingness to like truly
46:20 go to the mat against people like that
46:24 in your you know in that position is
46:26 very slim so
46:28 um so we lost that that battle and so so
47:32 next time you want to give away Equity
47:33 just let me in case you know we’ll be
47:34 happy to kind of you know take you up on
47:36 it and had YouTube sold to Google at
47:40 that time or not yet yeah and I think
47:42 that’s worth mentioning like you know we
47:45 had I sort of assumed that we had lost
47:48 right like I didn’t see a path for Vimeo
47:51 to become worth you know when it had its
47:53 IPO it was worth eight billion dollar
47:55 it’s not worth that anymore but um you
47:58 know I never in a million years saw that
47:02 when YouTube became YouTube I in my head
47:05 figured all right well like that was our
47:06 shot and we missed it um and you know so
47:10 Vimeo was turning into something else
47:12 but it was always you know a thorn in my
47:15 leg um and and frankly like you know my
47:19 just like way of thinking about
47:22 businesses is not always conducive to a
47:25 company that is pre Revenue spending as
47:28 quickly as possible to try and get users
48:31 with no monetization strategy I’m much
48:33 more simple-minded and coin operated
48:36 when I think about companies I like you
48:37 know generating revenue and profits and
48:41 you know I can wrap my head around that
48:43 um it’s harder for me yeah we get
48:45 approached by a lot of those kind of
48:47 businesses that have no assets you know
48:49 no Revenue it’s the hope of basically
48:51 growing it enough to be able to sell the
48:52 thing and those are those are risky
48:54 businesses right so so Josh as we start
48:56 to kind of get into the wrap up of
48:58 what’s going on here so what did you
48:60 sell
48:01 tuu um tuu was acquired for 41 million
48:05 in
48:06 2018 exciting and you were solo owner or
48:09 did you Shar some of the equity I never
48:12 raised any money we had an equity pool
48:14 for our employees um but I was the you
48:18 know I put the money up for the business
48:19 it was it was my company um and so six
48:23 years later do you feel like the the
48:24 buyers were happy with it I know for a
48:27 fact that they’re happy with it because
48:28 you can look at their um it’s a public
49:31 company and the the business has grown I
49:34 guess I don’t know four times over from
49:37 what I sold it for I don’t know exactly
49:40 what the profitability is because I
49:41 don’t know that they break that out um
49:43 in their annual report but um but the
49:46 business has grown dramatically um which
49:49 is you know both exciting but also a
49:51 little bit annoying um but you’re still
49:53 happy you sold it at that time right and
49:55 hindsight you know it’s not like the the
49:58 the the kind of the situation with IAC
49:01 where you kind of really the back of
49:02 your head like maybe we shouldn’t have
49:04 right in hindsight it’s a little is a
49:06 great number yeah I mean it’s some to me
49:09 as um you know it’s like when you run
49:10 into your ex-girlfriend or whatever like
49:13 you want them to be happy but you don’t
49:14 necessarily want them to be Blissful you
49:16 know but you built that and that’s the
49:18 beauty behind it so so what now so okay
49:20 you’ve got your exit you got a big exit
49:23 and uh so in 2018 so what then becomes
49:26 it what are the new Ventures what’s what
49:29 are you up to now what’s that next phase
50:30 in in in Josh’s career from 2018 to
50:33 today so I really try to divest myself
50:37 from all responsibilities immediately so
50:40 I sold the business in November of 2018
50:44 and by January 1st 2019 I was unemployed
50:49 um and really wanted to just you know
50:52 have as much space as possible to try
50:54 and figure out what the next thing was
50:56 um and you know I started I made some
50:59 early stage Investments I you know
50:02 joined a board or two um you know sort
50:05 of started just thinking about like what
50:08 are next steps and exploring different
50:10 opportunities um I found a business that
50:12 I wanted to acquire later that year um
50:17 to the point where I had a fully formed
50:19 you know long form document that was I
50:22 thought we were you know maybe a week or
50:24 two away from closing we’ already done
50:25 most of our diligence it was you know
50:28 trying to move very quickly and
50:29 ultimately the founder decided that he
51:31 didn’t want to sell the business so I
51:33 was really disappointed because it was a
51:35 perfect match for me it kind of touched
51:38 on some things that I was excited about
51:40 personally um and it was the type of
51:43 business that I knew I could grow really
51:45 well um and that sort of got me and it
51:47 was in the wine space it was a wine Tech
51:49 business um and uh and I thought it was
51:53 you know and it was a community it was
51:56 there was a lot of really appealing
51:57 things about it um but when that
51:60 happened it occurred to me that you know
51:02 doing something in a space that I was
51:04 really passionate about I’ve been
51:05 collecting wine
51:06 for almost not quite 20 years but a long
51:10 time and um and I thought it would be
51:12 really fun to Pardon and you collect
51:14 watches right I do although fewer now
51:18 than you know when I first sold my
51:20 business I went a little overboard
51:21 perhaps but you’re one of those watch
51:23 guys see this is my watch right here a
51:25 Samsung G smartwatch so it’s kind of
51:27 interesting Josh you you go from being a
51:29 startup guy right being able to take a
52:32 company grow and now you’re looking for
52:35 you know already existing businesses
52:37 generating cash that you can buy and you
52:39 can grow uh fits very similar with our
52:42 meth methodology of what we look for
52:44 right is is businesses that are existing
52:46 we don’t have to go in create the
52:48 concept create the the initial five
52:50 years of grind but then we can acquire
52:52 and then we can bring our skill sets and
52:54 bring in those things to make it better
52:56 so is is that kind of where your mindset
52:58 is now in your life where you’re
52:59 thinking hey I don’t want to do the
52:00 startup thing I really want to take
52:02 something that’s a little more mature
52:04 and then add your entrepreneur you know
52:06 G grow it yeah that that value and grow
52:08 it yeah ideally and I think you know I
52:11 have a a wine business that I did end up
52:14 buying um a large piece of um and I’ve
52:17 enjoyed that a lot um and that was sort
52:21 of the thinking there was you know it’s
52:24 partnering with somebody who really knew
52:25 wine much better than I did and
52:28 understood um just the wine industry
53:31 much better than I did but I understood
53:33 e-commerce and you know building a tech
53:35 business better than they did so it felt
53:37 like a nice complimentary relationship
53:41 um things like that I mean I guess you
53:45 know more simply put it’s it’s for me
53:47 it’s about finding projects that are
53:50 exciting that I enjoy working on more so
53:53 than anything else and and also just
53:55 finding people that I like working with
53:57 like I have no appetite to go work with
53:00 people who I think are losers or not
53:04 even losers you know just not fun to be
53:06 around painful people you spend more
53:08 time with them than usually your spouse
53:09 right I like to say the no [ __ ] rule
53:11 right you know I mean that’s it’s got to
53:12 be good yep so working with people that
53:15 aren’t fun is a
53:17 non-starter um I don’t you know
53:19 obviously as an entrepreneur and as a
53:21 business person you care about the
53:23 financial success of a venture but truly
53:26 it’s it’s not the most important thing
53:28 to me at all I care a lot more about
54:31 just enjoying the thing and I also feel
54:32 like you know if I’m learning and I’m
54:34 able to you know be productive and
54:36 contribute to something like that’s you
54:38 know I care more about that and and I
54:40 think about making Investments now more
54:44 in terms of things that will take up
54:47 time in a productive way for me that I
54:49 can add value to versus you know I
54:51 stopped Angel Investing almost entirely
54:54 somewhat recently because you know that
54:56 writing Small Checks Into startups and
54:59 then getting a you know an update once a
54:02 year or whatever that’s not very much
54:04 fun I I would much rather write a larger
54:06 check into something have a real seat at
54:08 the table and and potentially get you
54:11 know additional upside because of my
54:13 involvement um or your hands dirty yeah
54:17 I mean it’s you know um I really enjoy
54:21 working and um the most depressed I’ve
54:24 been as an adult where the you know
54:28 shortly after selling both of my
54:29 companies um so I think it’s sort of
55:32 counterintuitive and people it’s also
55:34 the type of problem where you know few
55:37 people will give you sympathy for that
55:40 um but you know the truth is uh you know
55:45 being rich and bored Is Not Great a good
55:50 recipe and that’s where getting people
55:52 at a similar caliber around that’s the
55:53 power of like a mastermind group right
55:55 talking to people that have been there
55:57 and done that I mean we were nominated
55:58 for entrepreneur of the year and the the
55:00 most impressive thing was the people in
55:01 the room that have had the same
55:03 challenges right from you know from the
55:06 lawsuits or bankruptcies to you know hey
55:08 I sold a business and I don’t even know
55:10 what to do with myself right how do I
55:11 keep myself busy I mean it’s you know
55:14 people as much as there’s no sympathy
55:15 for it it’s real things that people got
55:17 to get out there and find someone to
55:18 kind of relate to for sure and it’s also
55:21 very difficult if you’re in a situation
55:23 like I’m in you know you can either I’ve
55:26 had offers to go take CEO jobs I don’t
55:28 want to take a CEO job that’s a very
56:30 different you know I think a lot of
56:32 people who are maybe not you know uh
56:36 super experienced as business people
56:38 don’t necessarily understand the
56:39 difference between being the CEO of a
56:40 company you started and the CEO of a
56:42 company that someone else owns it’s
56:43 obviously a very different job um you
56:46 know so I could go take a CEO job don’t
56:49 want to do that I can take board seats
56:51 that’s good for like one day a quarter
56:54 so that doesn’t really you know do too
56:56 much to to make you feel satisfied dayto
56:59 day um or you know like so it’s often
56:03 like you know two extremes and it’s hard
56:06 to find things that are in the middle
56:08 and I’ve I’ve been able to piece
56:10 together a couple you know really
56:11 interesting Consulting projects um some
56:14 businesses that I have an ownership
56:15 stake in that I’m you know involved with
56:17 dayto day um but those are you know
56:19 they’re hard to find and um you know for
56:23 it to feel the way that running company
56:27 that you’re all in on and focused you
56:29 know 100% of your time on it’s it’s
57:32 really hard to compete with that and to
57:33 piece it together with a lot of these
57:35 other small things and it takes years to
57:38 do that at least it’s taken me that
57:41 absolutely you know those first world
57:42 problems but they are problems indeed to
57:44 have and so Josh Amazing Story love your
57:47 story uh we hope to get to know you more
57:50 um you know real quick just what the
57:52 listeners that are listening right
57:54 you’ve had a pretty amazing track record
57:56 you may look back and go wow you know a
57:58 lot of jumps and hurls and all that but
57:00 for the new entrepreneur or the person
57:02 that’s you know in Corporate America
57:04 they’re wanting to make that leap of
57:05 faith into entrepreneurship maybe buy
57:07 their own company you know what’s your
57:09 words of wisdom for I mean I always
57:14 think about these things is just like
57:16 Risk mitigation like I think um the idea
57:20 of like just jumping all into something
57:22 is is daunting but I think most things
57:25 you can take a really small bite out of
57:28 it and and Chase it down and you know
58:30 pretend that you’re starting tomorrow
58:32 right even if you didn’t quit your job
58:34 yet just start doing the thing like you
58:36 know think about like you know as if you
58:39 were working on it full-time like what
58:41 are the things you would do and and and
58:44 I’ve found in my experience oftentimes
58:46 within three months of doing that you
58:49 discover a this is harder than I thought
58:52 it was going to be or B this is like an
58:54 even bigger opportunity than I realized
58:56 and you know I think every idea when
58:60 you’re just like sitting with your
58:01 buddies having beers or whatever can
58:02 sound really great and then it’s not
58:04 until you really start to do it that you
58:06 understand the the full scope of the
58:09 challenges and or the full scope of the
58:10 opportunity as it as it could be so I
58:13 think um trying to figure out a way to
58:16 do something on the side and just like
58:19 really you
58:20 know just tease it out a bit and and
58:23 understand what the work is actually
58:25 going to look like I think is is really
58:27 smart and I think sometimes people just
59:30 you know get excited and and maybe jump
59:32 in a little prematurely 100% I mean too
59:35 many people think it’s about All or
59:37 Nothing versus you know it’s about
59:38 taking risks but taking strategic risk
59:41 right and understanding pieces to kind
59:42 of get you further along in the process
59:44 all right so now it’s time for our
59:46 rocket round and this is where we’re
59:48 gonna ask the guest three questions
59:50 right so first question what do you what
59:53 do you do in your free
59:55 time in my free time um I have two
59:58 daughters uh they’re 9 and 11 so I’m
59:01 mostly with them I cook dinner at home
59:03 just about every night um so I really
59:05 enjoy cooking I’m you know I’m in the
59:07 wine business I really enjoy wine so I
59:09 spend a lot of time um writing about
59:11 wine thinking about it um and I play the
59:14 piano so those
59:16 things since I have two daughters too I
59:18 have to ask you have you mastered the
59:20 braids
59:21 yet I have not my wife is the braider in
59:24 yeah I got them figured out so you know
59:26 I’ll teach you the tricks one day um
59:29 next question what’s been just kind of
60:31 your multiple your most memorable moment
60:33 in your business journey I don’t know I
60:36 mean I think there’s so many of them um
60:40 you know I think there was a moment when
60:42 we were you know within a like a one
60:45 month period we got flown to you know
60:49 the VMAs to sit in the owner’s box with
60:52 all the MTV Executives then you know I’m
60:54 on Richard Branson’s Island with him and
60:58 you know a bunch of other people that
60:59 are amazing for a week and then I’m at
60:02 you know the Allen Company Ranch like
60:04 you know that all happened within like a
60:06 month and then I’ve never been invited
60:08 to any of those things since right so it
60:10 was just like this moment of like you
60:13 know when you’re young and you’re sort
60:14 of on this up trajectory um and the
60:17 attention that you’re getting is a bit
60:19 infect you know it’s just it’s crazy
60:21 right so like I think that feeling was
60:23 was pretty wild um and also you know an
60:27 interesting lesson in like you know it’s
60:29 these things come in waves and what’s
61:32 popular and what’s getting a lot of
61:33 attention one day is not necessarily
61:35 going to the next awesome all right last
61:37 question is so what’s your favorite your
61:39 resource or tool that you like to use in
61:41 business or just in your own personal
61:43 education what do you enjoy I mean I
61:45 like to read a lot of non-fiction um not
61:48 just you know I sort of gotten a little
61:51 sick of business books but I do enjoy
61:53 reading biographies of people who have
61:55 done impressive things um but as far as
61:58 like a you know specific tool I mean
61:01 it’s mostly uh you know reading it on my
61:04 Kindle but I don’t reading is a fair
61:06 answer have you read that new Elon
61:08 biography yet I have not it’s sitting on
61:10 my desk and I have not opened a page yet
61:12 but one day I’m G start that one up
61:14 awesome Josh it’s been amazing I mean
61:16 definitely really enjoyed the
61:18 conversation last question for for those
61:20 that are interested I mean if someone
61:22 wants to get a hold of you how can they
61:23 get a hold of you I’m Josh Abramson on
61:25 Twitter I guess right there you go
61:28 perfect Josh thank you very much for
61:30 being that show it’s been a pleasure
62:31 wealth of knowledge and you are kind of
62:33 the canonical example of a seral
62:34 entrepreneur awesome thanks guys I
62:36 really appreciate it thanks for spending
62:37 time with us right talk to you soon
62:40 thank you for listening to the m&a
62:41 Launchpad podcast if you’ve enjoyed
62:43 today’s podcast and would like to
62:44 support us please leave us a rating and
62:46 a review after you listen I’m Casey muu
62:48 and I look forward to talking with you
62:49 next week
