Matt Morchower: Deep Diving Entrepreneur

Matt Morchower is a serial entrepreneur. He co-founded Marquis Jets, which was later sold to Berkshire Hathaway, was the COO of Magnises – the exclusive card for millennials – and was the president of Clipper Jet. In our interview Matt shares his three-pronged theory to what a modern entrepreneur can be, how to become an entrepreneur, and dives into how he focuses to generate his own competitive advantage.


Below is the transcription from my conversation with Matt Morchwer.

What is the origin of your name? I’m from an area called Galitzia – 

George is from Romania – did that have anything to do with your ocnnection?

It did. goes back to my first job after college. I finished college, always had wanted to go into TV & The media  and got a job at CBS in a position they call an olympic researcher. It was for the ’92 olympics. And you spend the 2 years before the games, traveling around the world, by yourself, interviewing olympic contenders. You need that because its not like the NFL where all of the announcers know about Peyton Manning, etc. When you’re covering the olympics, there are all these figure skaters you’ve never heard of and bobsledders, so you have to put together biogaphics on all the athletes. So i spent 2 yeas going through all these countries that have a pre-olympic circuit. i’d go to an event one week in Valle-desaire france, figuring skating event the next week in Sophia Bulgaria, and I have event in Romania, and I’ve seen places in Europe & Eastern Europe that nobody has. I’ve been to Slovakia, And i’d sit down with 50 or 60 people, top athletes, get their bios, and then I came to New York and in the months before the olympics, write 2500 biographies on all of these athletes and their pronunciations, and the announcers, when they’re doing the events, they’ll say “Ok, this guy finished 3rd, lets go to the bio (that Matt wrote) and they’d say “Hey! so, and so is from…Mammoth California!”.  So, with George, I knew his neck of the woods. Over there, it’s not as entrepreneurial. Its becoming that way now, because they’ve seen the world of opportunity and the world shrunk. I just understood [george].

First job you got out of college was CBS – you had always wanted to work in Media. 

Its funny – I had always wanted to work in Media. Sports I sort of knew. I got the job at CBS because the games were in Albertville France, and I knew how to speak French.

They interviewed about 500 people for the job, and they wanted someone who knew about the world, who know about sports, olympics sports, could bounce off a plane and interview and speak french and interview. And I knew all that, and that was lucky. But going back to high school I knew i wanted to work in TV.

It goes back to a biography I read by a guy named Porter Bibb. He turned into a venture capital guy, started out as a writer. Wrote a biography of Ted Turner. And, high school was right around the time that Cable TV was becoming big. I always knew the name Ted Turner because he owned the Atlanta Braves and he was early in Cable TV. I was like “Wow, this guy has it made. He got early in cable TV, CNN, TNT, he owned a baseball team – he didn’t even graduate college”. And so i thought “I like the way this guy has put everything together.” In high school, you think that everything has been invented.

So I was 16 or 17, and i’m like he did “Ah, he did cable TV already, what’s left? I’ll just follow in his footsteps”. So I went to college – Amherst college in Mass. I had no inclination to be an entrepreneur i just knew i wanted to work in TV or Media in some way. And I got this job and loved it. I stayd at CBS for about 5 years. Then my boss at CBS said he was going to TNT in Atlanta – the sports division called Turner Sports. We’re gonna try to turn it around. We’ve got the NBA, NFL, Baseball. And I thought “ This goes back to when i was 16 and 17, and loved Ted Turner and his entrepreneurial nature and here I am going down to the empire he started.

It was great, because this tied it all together. I new I never wanted to be a Wall Street guy, i was a creative guy, i liked writing and video. And I thought “I am now going to work at Ted Turner’s crib.” I’d see him in the elevator – never too good for everybody. I had worked at other conglomerates before my entrepreneurial career where the CEO would get in the elevator and all of the sudden the security guards would rope it off before you could get in. Not that i’m talking about Lawrence Tisch at CBS, but that would be a good example.

Ted was a guy’s guy. Not only was he an Billionaire, but he was so down to earth! I thought – that’s the way to be.

the funny thing about turner, it was Big. CNN, TNT The braves, A movie studio – bought MgM – it felt flat and entrepreneurial. That was the first time I came upon the word “Entrepreneurial”. I just thought I had a job there. I realized it was an entrepreneurial culture, compared to when I worked at CBS.- which were some of the best years of my life, don’t get me wrong, and I’m still friend with people from CBS from 25 years ago. But it was just a much different – “we gotta prove something, we’re the new kids on the block” – and I just liked the flatness of it and the idea that “any idea was a good idea”. And I started thinking – what I didn’t realize at the time, but what I now realize was – entrepreneurially.  And i read some more books on people who started their own thing. I read a book on Famous Amos.

Then i devised my own take on what being an entrepreneur is.

You’ve gotta like to work. Within that, you’ve gotta either be fierce, or have a focus. If you want a dilbert job, to sit in a cubicle – nothing wrong with that – you’re probably not cut out for it.

My own version of what an entrepreneur is has 3 parts to it, under an umbrella.

1) We are all the entrepreneurs of our own lives. Doesn’t matter if you work at Xerox, Alcoa, Firestone. Because it just means your’e someone who thinks, and tries to come up with something people need or desire. IBM may be the only place you have the resources to do that. If you’re working – BMW has the thing where your car will stop if another car gets too close to it – someone thought of that. They didn’t start it in their basement with their friend. They had an entrepreneurial idea, just in a longer context.

2) Go work for a company that is entrepreneurial.

3) Have the idea yourself.

Why I like the 2nd way. Odds are you’re not going to come up with the idea that the entrepreneur would. Those are few and far between. I know a lot of people who sit around and think “whats the next big idea! because I want to start the company & be a real entrepreneur. Its a coffee cup on wheels!”. Thats ridiculous – you’e wasting your time. If you have a big idea like Zuckerberg or Biz Stone, or Henry Ford even – go for it. If you don’t have the idea, or an idea, don’t sit around waiting for it to strike, go work someplace entrepreneurial. Be the 150th hire at Facebook. Your’e in an entrepreneurial environment. You’re still an entrepreneur – if being compensated down the road is your think – thats great. If carving our a company’s path is your thing- thats great. But a lot of people say to me – “whats the best way for me to get into entrepreneurship”. I tell them that the worst way is to sit around waiting for a big idea. You’re never gonna get that – most places fail.

The hardest thing about entrepreneurship isn’t even the idea – its raising the money for it.  You want to spend years with your hat in your hand, trying to raise money for an idea that may or may not work? Or do you want to be employee 200 at google, trying to do something that creates change? Or, even better – do you want to work at Ben & Jerry’s and figure out a new lid for them?

All of the above is an entrepreneur.

Can we name 15 or 20 of them who have really don it and done well, gotten the money for it, and it has gone smoothly – it does something that peoople either need or want?

I’ve been wrong about a lot of things – but I don’t think there is a desire amongst people for a car that drives itself. I could be wrong, doesn’t float my boat, but thats an interesting entrepreneurial undertaking. If you do it for the sake of doing it – thats cool. I don’t know, driving is fine. Driving the way we drive is fine. Now, something that is more airplane-like, where you’re off the highway, soaring over things, cuts 90% of your travel time – that works for me. Even the best-sounding ideas don’t click.

Writers are entrepreneurial. There is a lot you can do that is entrepreneurial without moving to silicon valley.

You’re the entrepreneur of your own life – if you want to be.

Where did Marquis Jet come from? 

I was not a big flight guy. I didn’t grow up with airplane wings clipped to my Lapelle.

I had been working in TV about 8 years. I said “I DO want to try something entrepreneurial”. I don’t want to be locked into the big corporate monoliths. I want to start my own independent production studio.” There, I could use my own creativity, come up with show ideas, and pitch to the 200 studios out there. But, i said to myself “to do that, I should probably learn how to count”. So I went to business school – I went to Columbia and got my MBA. In hindsight, that was a horrible decision, because you can always hire someone to do that. I took a class in entrepreneurialism – snore – whats that gonna teach me?

I overestimated the need of being a balance sheet/incomestatement/equity table/ cashflow statement guy. And i guess I was just trying to make myself be a perfect spherical ball so when i started something nothing could get by me.

The key to starting something entrepreneurially was hiring the right people. And I learned that 6 or 7 years too late. I did business school, it was fine. Tell you the truth, Friends, contacts, that part was great. Could I have done with out throwing myself 150K in the whole? Yea, that would have been fantastic.

So, got out of school – I had known my partners Kenny Dichter and another guy for a while. And it was almost like you and I sitting here. We had always wanted to go into business together somehow. Those guys had been in the music business and were familiar with private jets. I was somewhat familiar with them from TV, and we started saying a lot of “What if?”. Like, Ok there are a lot of jets out there. What happens to their un-used hours?

So we did a lot of independent research on it. the more research we did, we realized that NetJets was there with some people my guys knew, and they had some excess capacity. Did we want to strike a deal with them and use their excess hours? We went through a lot of iterations. I co-wrote the business plan with the guys. NetJets signed on to let use their fleet & take their idle hours and sell a 25 hour jet card – and we co-founded Marquis Jet.

It was an interesting time in the world. Somehow the status symbol went from a Bentley to a Jet. And I don’t know why that jump was made. The 2nd part was that the TSA went nuts on people, people wanted to avoid airports. And there was a big wall street boom. So we put it all together – people could fly private, avoid having someone put their hand down their underwear, and save time, take the dog.

I never had a passion for jets, but i enjoyed the puzzle aspect of putting this together. It ended up working. The guys loved the jets space, I enjoyed it. Strong sales effort, contacts & connections, and it grew to the point that we could sell it to Berkshire Hathaway.

I took away the one lesson that has stayed with me. I like having and starting my own companies – OR – like i was saying, i like jumping in early on someone else’s company. I want to be comfortable, but I don’t need $100MM or anything.

We met with Warren Buffett – this is not a name drop – but he said something really interesting. “Look, my business happens to be the money business. That is the end result. You all should do whatever you like. It doesn’t matter how people keep score or what the end result is.”

He made a great observation. He said of course I have a lot of money, but everyone in tthis room has enough money to wake up in the morning and go to Paris if they want to. It might be a full coach fare, but you’ve got enough money without being a zillionaire. He said that Paris is the same for both of us. For you guys are starting, and for me who has billions. The Arc D’triumph is the Arc d Triumpm. We all probably have the same thread count sheets. There is no special TV for billionaires. We don’t have our own stations that we get to watch. Don’t get caught up in the money. You’re all gonna be able to do what you want to do in life.

That was interesting, and it taught me that I don’t need to break the bank, but I like doing things that I like. Entrepreneurial, non-entrepreneurial. It reinforced that I don’t need to be the lead dog in whatever I’m doing. And that informed the next few things I did.

So we finished Marquis Jet.

My next job was at a company called Magnises.

I had a professor in business school that said the best source of ideas will cost you a dollar a day. It lands on your front porch every day: The newspaper.

When you read the newspaper, you will see ideas, you will see startup companies, and things that start you thinking.

I was reading, and I read about Magnises, and so I decided to call them. This was a company that was marketing a black credit card for millennials.

To give them a real sense of worth – like i’m in my 20s, and this is a nice thing to show i’ve made it.

Before I joined, they made it so the perks and the benefits are relevant. Not a night at the Westin Skiing at Vail. Lets make it a Rick Ross concert, or an event where Tesla comes in and we test drive teslas at Monmouth airport. And, lets make it sort of clubby. So, you get your Card, pay a few hundred bucks for it, and we had a clubhouse in Greenwich village where people could hang out and network through this card.

That was all laid out before I got there. And they were hiring a COO, and thats where I excel: getting things done and making them happen.

I came on board as the COO, made sure everyone stayed in their lane and did their job. Along with the CEO, We came up with something that was an unintentional finding. People who joined Magnises for this card were self-selecting. Something I learned in TV is Advertisers try to reach their audiences through TV with the right demographic.

Millennials were impossible to reach, and marketers were tearing their hair out because they couldn’t reach them.

I said “Look, we have this self-selecting group that has opted into this card. We have a space, why don’t we have products sponsor events and evenings for these 5,000 people – influencers – who have the card in NY?” We got a lot of brands in the door – Tesla, Tito’s vodka, a lot of fashion companies”. The would sponsor events and market to our client base, and word would get out, and the advertisers were saying “we now have a hook into these millennials!”

We expanded into washington, soon into florida. I’m still on the (advisory) board, so I stay in touch with it. Once you have a national footprint, and 100,00 people with this card – it is an opt-in marketing tool, where the people who belong to it want to do fun stuff – we can bring them the fun stuff.

We can have Audi A-1 sponsor something for us and park the car outside. We could have an affordable private jet company sponsor some stuff. We can do the same thing with new coffee shops.

So we have an incredible group of Millennial Influencers that we can now take to advertisers who will pay to market to them.

Why is it self-selecting? 

They had to apply for the card. That was the whole thing – we made the card seem sexy enough – that, when you live enough of your life online, here is a way for you to join some other millennials in our Greenwich Ave clubhouse space on a weekly basis for happy hours or for special Chefs tastings or for nights out with James Blake at Zegna where you can get a suit fitted for you.

We made the perks cool, and things you can do as a group. They like that sort of Offline compliment to their online lives. We felt the pendulum swinging a little towards group gatherings, great networking and the ability for products to come in and throw them a great evening.

This is going full throttle? 

Beyond full throttle. It hit Washington with an immediate 5000 people signed up for it. Look out for South Florida and Boston and when it hits LA and the West coast. It will be 100k or more people with this. That is a great critical mass for people for marketers to access. That is a funny one because it was someone else’s idea, i came in, we played around the edges, and it turned into something a little different, but not something I started. I was one of the early guys in, and I took pride in it. I don’t need to be the guy with his picture in Manhattan Scene or New York Magazine. I just like doing my work.

I like the fact that starting a new company is a puzzle.

Where does that drive come from? 

Not sure. You can be entrepreneurial at a TV network by coming up with a great idea for a show, but I also saw a lot of waste and abuse at networks. I saw a lot of mediocrity there. a lot of people were let go in layoffs who shouldn’t have been. It seemed like a lot of these places weren’t created to be nimble. It was always frustrating, and I thought I had enough ideas and could come up with a different way to do things.

Being at a new venture lets you road test those things. You don’t necessarily have to wait your turn, and I’ve always been a little bit impatient. That is the thrill – we created something that didn’t used to be there. I always loved that concept, that people are using what we created.

Where did clipper jet come from? 

I could not have been happier at Magnises. I would have loved to be a part of it going national. To clarify, I’m on the board of advisers there, not on the board of directors. I still love watching it, and I still meet with the CEO. Wasn’t looking to leave. Came back from Thanksgiving 2014.

Remember how I said business schools was a waste? Compared to people i’ve had as mentors, it definitely was. I’ve been lucky – i’ve had great mentors in my life, and i’ve lucked into them, and a lot of the time they were 20 years older than me. I had a mentor, guy named Pete Pappas, worked at American Airlines for about 20 years. He introduced me to some guys who were starting Clipper jet.

Marquis Jet was Pioneering in the way it brought pritnvate flight to a new demographic. You didn’t have to be in the top 3% of the country to afford it.

Clipper jet was the next iteration of Marquis. Selling seats on private jets individually. It was broadening. The idea was to take people out of first class on delta, and for maybe 35% more, drop them in a Gulfstream.

I had done something that was Groundbreaking before – i had been involved with it. I wasn’t the guy who operated it day to day and make it happen, but I knew it – the business plan, the evolution, and the sale. The Clipper jet guys were doing the same thing, and said “Lets bring on someone who has innovated before”. They said they could give me X, Y, Z, and be president of the company. What do you say? They made me the offer I couldn’t refuse, when I wasn’t looking to leave. But I couldn’t turn it down.

I wasn’t the guy who ran Marquis, but this would be largely my show. So, when it came time for the marketing, branding, sales, customer service, all of that, retention -that would fall in my lap. So I took it.

We had a waiting list of over 100 people to get going, we had our new model.

Here’s the bad part of the entrepreneurial world, especially for the person who has the idea – the raising money part.

My boss at Clipper, who had been at American [airlines]for about 20-25 years, didn’t have the track record and entrepreneurialism. He had a commitment for the money, then he didn’t, then he did, then he didn’t. Ultimately he didn’t, because he hadn’t shown entrepreneurial success in the past.

Again, the hardest thing about a) is it gonna catch on but b) can you raise money?

Its sort of like the TV or Movie business. Matthew Perry did friends, so he now gets 10 free shots at another sitcom.  Stephen spielberg did Jaws – he then got 10 free opportunities to direct another movie. The guy who finished 2nd to Matthew Perry in friends and didn’t get the job? Maybe he hasn’t worked since then. So,  you do it once, you get another shot. Look at Jack Dorsey – He did twitter, and then he could raise money for square. Its like 1 hit buys you the ability to get new hits. 

Does the first idea need to be the first idea? 

No. But as long as you’ve taken in a dollar from someone, not wasted it, either gotten them a return, or come up with something that was ahead of its time, or developed them as a contact, or been trustworthy with their dollar.

My Dad used to say “ I’d rather have a dollar than not have a dollar.” Why wouldn’t you, you just bought a coke? Whereas before, you weren’t buying a coke!”

And, if someone invests something in you, and you can show them that you’ve done your best to make it work, and you’ve had a mini success, but not a big one, you’ve met a lot of people in that Angel or VC firm – it is much easier to go into their office again. Especially if you’ve shown yourself to be funny or creative.

for my years when I was running my TV production company, and would pitch shows to guys in hollywood, it was never a bad meeting, because they’d say “nah, Morchower we don’t want that show. But, lets get a drink later”. If it was halfway intelligent, they don’t want to miss the next one. 

If it was a good meeting, he’s gonna remember you, and the next time you call, he’s gonna be like “yea, come in!”.

There is no such thing as a bad meeting, unless you insult someone’s wife or husband, or anything you’ve seen in Seinfeld.

This is a little tangent:

whenever you’re looking for money, and your’e using a powerpoint, you cannot have a single typo. You can’t have a single bulletpoint that is a little more indented than the other bullet.

And people are like “Ah Matt, you’re so anal”. It fits into the Fierce Focus – I’m focused on that bulletpoint being a little askew from the others. People think to themselves – if he’s making mistakes on the small things, what is he gonna do on the big things?

when you hear news news anchor say “there is traffic down on Houston st.” , its like “I hate to say it, but your entire news cast is tarnished! because if you can’t get this news right, how do I know that you just explained…common cause properly to me”. Its a credibility killer.

Read the rider! Its the easiest thing to do. Making Facebook was hard. Putting out your presentation should be really easy. Don’t spell There wrong. Its a pet peeve but it something that hits me. Thats how you get laughed out of the room.

As of last December, it has opened up a whole new world to me. Out of Clipper, out of Magnises, and once you’ve done it a couple of times, a lot of people start calling to you, start coming to you.

Do I have a lot of great ideas for the next big thing? No. But, do I know a lot of people who may? Yes.

So, in the last couple months, I’ve worked part time at a VC firm LunaCap. Thats How I met George.  Thats how I understood how they do what they do. I am working as the interim COO at a company called SomaDome that has created a personal relaxation pod. You lay in it, put on headphones, and the ceiling is decorated with crystals with different colors. The headphones have Bi-Aural sounds that calm your brain, and there is a soothing voice. Who knows, maybe Alcoa is going to buy it and put it in the lobby for their workers who are stressed before a meeting.

It could also be a piece of gym equipment. If i’m at Equinox and I want to calm down after my workout or after my day, I’ll use it. It is calming to the point that, we haven’t rolled it out formally, but we’ve had about 1000 incoming inquiries about it.

The Ojai spa in California bought it – people get charged a mini surcharge to use it. In a couple of months, these surcharges have bought in another 10k for people who want to use it, and we split that with the resort. We’re still nailing the business plan, and there is a whole assembly line function to it.

People from Dubai are interested in it. My CEO went there because they have all those nice hotels there. Someone wants to buy the exclusive distribution rights to it for Australia. We need to slow down and get the business plan set – the puzzle.

Are we really going to start marketing to Dubai? Or do we want to get it here first? After you get 1000 incoming calls, where do you go? That is a puzzle. Then, staffing it up is a puzzle. So, that is part of my time.

I just started a female-oriented nutritional supplement company called expert alternative. I make a point, and maybe everybody should – to never work with a friend or family member. it never works out well, I never hire friends or family because you want to have the ability to get rid of them, you don’t want to be arguing with them over money.

This is the first thing i’ve really done with a friend, who runs the uro-gynocology department up at Mount Sinai. He has developed a lot of vitamin and herb based uro-gynacological products for women. so, he started this company, and i’m not gonna go into the intricacies of the first product yet because we’re 2 weeks from launch.

When i said there either has to be a need or desire for it – there is a need for it. there is a certain surgery that women have that cost the insurance companies $33 billion dollars per year that may or may not be necessary. And we think we can cut that in half. the funny thing is – when you talk about taking a deep dive to becoming a subject expert – I did that in Jets, and now I have done it with the uterus!

My partners is the scientist, but i’m handling the branding, marketing, the site & the outreach and the ads. I said to him, “chuck, i need to learn what it is we’re selling here”. so he brings out his little ceramic diagram.

Its interesting, he said “after everything you’ve done, when you hit it big, you’re gonna be tooling around with a license plate that says Uterine King”. I’m like OK – i’ll take it,  helping people!

How do you focus to create progress? 

Everyone has a competitive advantage. Some guys are really gregarious and they can walk up to Barack Obama and say “Hey you should hang my painting in your office!” Thats not me. I’ll talk to him, but i’m not gonna pitch him. I didn’t come out of the womb a salesman, and i’m not a Rhodes scholar.

My theory is people may out-smart me, but they’re never going to out-work me. the one thing i’ve honed is my research skills, to the point that some of the guys and my friends just laugh. At the end of the day, they think I stick my fingers into the internet and download all the information from it. I research things like crazy. Competitors, subjects, topics, anything that has anything directly or remotely to do with a product that we’re working on – I know. I don’t want to seem bragadocious here, but everyone has their skill. Yours is that you drill down with questions, you have an instinct with what is interesting and what people want to hear. Mine is this insatiable appetite for information. It bleeds into my regular life as well. It really get to work at work.

I don’t know if it is a photographic memory, but it is why I don’t make those mistakes, and I can pick out the blip in the sales collateral, all the way down to knowing all about uro-gynacology, knowing all about Jets. In the TV business, i was probably the only producer who understood the electromagnetic spectrum. Why? I don’t even know. seemed like it was kinda important, because that where our signal goes. It had nothing to do with my day-to-day, but I’m like “alright, if i’m gonna work in this field, so i’ve gotta know it”. to the point that, when i have a meeting with someone – whether it is with a VC or a potential partner in something. I make it my business to know more about their company than they do. So, when i was running my TV company and pitching my show to some development company at MTV, I would walk in there knowing Viacom’s stock price, and their board, and what All of the viacom networks are looking at. So, i’m pitching to someone at MTV, but i still know what VH1 and CMT and BET and Nickelodeon were doing. I don’t know why, but I just thought “you know what? I’m gonna learn all this, because if it comes up, i want to seem like a subject matter expert.

That’s my one skill: never being unprepared. For this, i listened to the podcast, got down and dirty, got a sense of the things people told you that were interesting, and the directions to go. A lot of people probably come in here and wing it with you, and they may be 20x more informative or entertaining than me, but this is how I know how to do it.

I know the number 1 rule in business is don’t tell everything you know, and #2 rule is refer to number one. With that in mind – is there a resource that you use – scholarly articles? or just exhaustive everything?

Exhaustive everything. Ok, for our new uro-gynacological business, I was reading National Institute of Health experiments on Rats, where they were taking VitaminA, K, and green tea extract to see if they had the proper effect on these lab rats, that ultimately led to what my partner discovered worked on people. Learning how much the insurance company spent on surgeries. The demographic which certain urogynacological issues happened, occur with people. It gives us an advantage because – guess what – now I know the demographic that suffers from malady A, Ok i’m gonna go find websites that target women between 21-45. Bingo-  that came from web research. I still go to the library and buy books. And i just enjoy it. And I try to know everything about everything. Not because I’m smart, i just retain it.

I have no idea what happened in the Peloponnesian war – but when it is something i’m working on, or something tangential to it – or if I have a meeting with a VC, I will know which 10 of his deals really did well for him, and which boards he is on, and if he has a little play money on the side. I’m like “oh, i kinda like how you took 10 million there and bought a share of the Mets”. Maybe it starts a conversation on the mets, but it shows you’ve done your homework, and I think people appreciate that.

Where do you focus? 

At the gym. Or when i’m running. When my brain is more free. When i’m at work, i’m focused on what I’m doing. I have what my friends call AFD – Attention Focus Disorder. So, at work i’m focused on what i’m doing. Where i’m focusing freely, letting my mind wander, i’m at the Reservoir or at the gym, and thats where some of the more far-out things come. Not to say I think about work all the time – I don’t. But in the office, lets focus on what we’re doing. Outside of the office is where the more creative things come to you.

Where I don’t focus is at home. When i’m at the apartment, i’m at the apartment. I don’t like working there. I’d rather stay in the office until Midnight and when I get home it is my time. Watch TV or read or catch up with things, but home is where I don’t focus on work at all.

Tell me about your Bruce Springsteen Shirt. 

I’ve got about 30 shirts that have Bruce Springsteen on it. It happened by accident – big Bruce Guy. April 25 when he continues his tour at the Barclays Arena will be my 50th show. So I have 50 bruce shows before I turn 50.

when you go to 50 shows, you probably go to 50 shirts, and you can’t help but wear them, and I found that, no matter where i’m wearing one, at the gym, at the park, at the airport, someone always has something to say. and sometimes it helps with work – which is great when it does – or it is a way in to ask them questions about whatever i’m working on. It worked really well when i was doing travel stuff.  It works other places to – leads to a “what do you do?” – or maybe it leads to a different conversation and 1 out of every 100 leads to something thats like “hey, lets have lunch, i like what you do”.

That was trial and error. Wearing the ralph lauren shirt with the little polo thing on it – you’re not starting any conversations with anyone. I’m not so sure Elton John’s shirt would. But there is something about Bruce that everyone likes talking about – especially when i run into someone from around here. “Hey that shirt looks a little tattered! – I was at that show in ’81”.

They are also good luck. Any time i have a meeting and i’m dressed, the undershirt is a bruce shirt, or I sleep in one the night before I wear one to bed.

You don’t read books or watch TV on the plane – what do you do on the plane? 

The best ideas come from newspapers. I get really janky if i miss the times from a given day. or Vanity Faire or Sports illustrated. Airplanes are my catch up on the newspaper time. And, i’m sitting there i my seat, tearing out articles, stuffing them in my pockets. “this looks interesting – this guy is starting a new sports portal” i’ll cut that out, who knows if i’ll ever know him. I’ll get on a plane and i’ll have 2.5 weeks of the NYTimes or the Post and all that, and i’m reading it for fun or for the sports.

have you ever been surprised at what is in the newspaper? 

2 things surprise me: when people i knew from college or growing up are in the NYtimes, always throws. me. Even my partner in my Expert Alternatives business is a doctor.  I go to his office and I walk in and say “hey, where’s the adult supervision here!?” and he said “I am the adult supervision!” so when i see my friend quotes in the paper, yea that throws me.

When they fired Dick Costolo, that surprised me. Then, you see the letters to the editor, people saying “you know, i never really understood how to use twitter” Wow, thats interesting, it is kind of confusing. From the last week or two, the big debate about encrypted or non-encrypted phones. Its kinda weird you have some terrorist’s phone, and they’ve decided his right to privacy is more important than decrypting the phone – thats not political I’m just saying in this one case – little things like that surprise me.

reading about where advances come from. I never knew WhatsApp came from guys just out of the Israeli military. You never know whats gonna hit you, where and why. Look, i’ll look about new tech magnates – one just bought an  NFL team – so i see that some guy who just bought the Jacksonville Jaguars made his money in Semiconductors. So let me find out some more about this guy.

How did you meet George? 

Through LunaCap. LunaCap is a venture debt firm. A thing i’ve always been interested in because as time goes by, i’m realizing some of my strengths, i like being day-to-day and having skin in the game, but I also like the challenge of the “entrepreneur in residence” thing – and I’ve been trying to balance the two. And I’ve always wanted to learn about the venture capital/venture debt space. So i’ve been in there part time, and George has been too. So we met, and we got to talking about all the thing he had done, and Boston Technologies. I love writing and he is working on Lending Times now, telling me about the difficulties of creating good copy on a daily basis. we just started brainstorming about how many exits there are on that. And we got together. Pipeline guys like that are interesting. Even if you get together for coffee, and you’re not talking about anything, he always got a pipeline of ideas.

Now you’re writing for TV? 

If I had to start life older when I was 22 – i’d try to be the next tom Friedman, Nick Christoff. Life is long, maybe at some point, i’ll flip into that. I think we’re gonna live to be alzheimer’s free, heart trouble free, living to 110 old.

What would you say to younger people? 

First you’ve gotta decide if you’re a worker. I love going to work – I don’t think i’ll ever retire. If you’re motivated to go to work, be a worker. Don’t waste your time sitting around trying to come up with an idea. either go to work – get whatever job you can. If you want to work entrepreneurially, find a job at a startup, live at your parents if you have to. If the thing that comes along is a job at Xerox – take it and be innovative there. For your early 20s, take whatever job you can get and just try to break down the walls, be creative and think about it. If you really want to turn innovative with it, start looking at things like Angel list – things like that. They’re not only soliciting money on those things, but they’re soliciting people. Junior manager of marketing – go do that. Go work for free as an intern somewhere. At Magnises, our interns were fantastic, and we couldn’t wait for them to graduate. Again, i hate to say it, go work for free someplace that is a startup. The difference between what the people on staff are making and what you’re making – pretty minor. You’re probably gonna be in the same tax bracket. But first, get whatever job you an get, and try to engineer change, and then if you really want to work at a startup, go work at one but do not sit around trying to come up with an idea. Let it find you. 

Thanks Matt. 


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