#AskGaryVee Episode 143: Unethical Investors Vs. Soft Entrepreneurs

“with any of your businesses?” – No, I don’t think
I’ve ever been reckless with my businesses, hence
why they’ve been successful. I think the only reckless
thing I’ve ever done which has caused me
non-successful ventures is trying to bite off
more than I can chew. Sometimes I’m doing way too many things including now, including always. So there’s a level of
recklessness within it, but on an overall collective, it’s not reckless because
it’s a net net score game and I win in business. And so no, I don’t find
myself to be super reckless. I think I’m very much on the offense, but there’s a level of practicality. I’m very P and L driven, profit and loss. That means cash flow, understanding how not to
put myself out of business. I think I leave a lot of
profit on the table each year. I definitely could have a
lot more take home money from Vayner Media, for example,
in the last three years, but I continue to invest in my businesses. Some may think that’s, not reckless, but maybe leaving something on the table? I look at it as long-term investing, not worrying about short-term cash. So no, I don’t think I’m
a reckless businessman. That’s it. No.

“and now Kim Kardashian? “Are subscription media
sites next celeb frontier? “And will you?” – The answer is yes. Will I have one? I, maybe, ya know? Maybe, I mean, that’s a
really interesting question. I’d be really fascinated, and I know Staphon’s holding
up the Scope right now. I’d be really fascinated
if I decided to paywall The #AskGaryVee Show or my
content, what would happen. My intuition is that I would
lose 90% of my audience, but the 10% that were the most passionate would find a rationale to pay for it. I do believe paywalls
are an intriguing play. If you look at somebody like Howard Stern. Went to a radio paywall. I think, until he went back
out into America’s Got Talent, he almost disappeared off
the face of the earth. He made a lot of money, but his brand took a hit. For example, I’m gonna
assume a lot of you, and a lot of you, which
are both one in the same, are gonna buy a lot of #AskGaryVee books or go to some of my speeches
where this is a jab. The content is free, but it’s
a gateway to brand equity that then kind of allows me to monetize on the back end. I do think that there’s a huge opportunity for paywall subscription based. I think there’s a lot of money in it. I do think a lot of people
are gonna go that route. I think you’re gonna see moves by YouTube, I think as we have a long
tail of micro-celebrity, more people will go there. And so, Trouty, I do think
there’s a frontier in that. It is something I debate doing. I tend to believe more in the fact that I’m not a Beck or a Kardashian, so I don’t have as much equity. I think at super scale, when
you have broad awareness, you have a better chance
of having meaningful scale and who will pay. I think there’s more upside
in me continuing to provide disproportionate value on this show and my engagement to keep
building up that equity. I’m looking for that depth. I don’t have that level of width. But yeah, I think it’s a
very good business model, and I do think that people will pay. I do think eight, ten,
twelve, twenty dollars a month for getting what you really want is not out of the question
if you have a lot of affinity for any content, sports, individuals, and
definitely celebrities. And so, yes and maybe. Staphon, what were they saying
on the Scope about that?

“just broke up, and I’m
feeling really depressed. “For the last four years,
I’ve had someone to talk to “about literally everything in
my life, and now that’s gone. “It’s hard to believe that
a four year relationship “ended in 20 minutes. “I was saving and planning
on proposing to her “in the next few months, and
now that’s not gonna happen. “I feel empty, I feel
a void, I feel blank. “Got any advice on how “to pick the pieces of my life back up?” – Jesus. (laughs) You couldn’t have warned
me this was coming? Well, ya know, I mean,
if this was my buddy, the first thing I would
desperately try to do is I always feel like the
quickest cure for heartbreak off a long-term relationship
is a scummy move of hooking up with as
many girls as possible. I think it helps in a weird way. I really do. I think,
I really do think it helps. So I think, there’s only
meaningful relationships and then kind of like the
vanity of relationships when you break this down, and so he’s coming from a meaningful place and I think the vanity of it all, like the one, the one
micropositive that guys cliche will think about in this moment is, “Well, I can hook up with chicks,” and I think you have to go all in on that. That will last for about three
weeks to three months of fun and is a softener. I think you need to recognize
that you got off easy. I don’t know if it’s Bronx Tale or one of those gangster movies where the guy owes the kid, the kid owes the kid 20 bucks, and he goes and chases him,
and then the gangster grabs him and goes, “You got off easy. “You found out he was a
scum bucket for 20 bucks.” You know, brother, I
gotta be honest with you. I think you got off easy. I mean, it’s a hell of a lot
better that you didn’t propose, that she was, I give her credit. She, a lot of people, a lot of people mail it in and get married to
people that they ultimately aren’t fully 100% infatuated,
in love, and for full life, and I think people are mailing in. Now that divorce is so easy, I think that people just kinda do it, and I actually think, in a
weird way, you got lucky, and I actually give her a lot of credit that she, after a four and
a half year relationship, had the backbone and the guts
to go through a tough process I’m sure for her as well. And so I actually think you
look at this as a positive. I’m an optimist. It’s easy for me to say, but I think at some level,
you take a step back and recognize as much as it hurts now, it would have been tougher and hurt more to unwind after marriage or, what’s so difficult for so
many, after having children which creates such a different dynamic and becomes extremely difficult. And so, you know, there’s
not much I can say that’s gonna make it
feel a whole lot better. Maybe just talking it out and getting the question on the show. The e-mail was asking
for it to be on the show? Or are we just taking somebody’s random? Oh it just, it came in, OK. So, that’s it man. I think, go hook up with some chicks to ease the pain for a few minutes, and then take a step back and
recognize it’s a positive, and then try to learn from the experience and find out the qualities
you really loved in her and try to replicate them in
the next relationship you have, and you know, maybe even find the things that you didn’t like as much in her and try to close the gap and find somebody you love even more.

“What happened to Tumblr anyway?” – Is Medium the new Tumblr? I think Tumblr is a more
creative outlet visually whereas Medium, I think,
is more creative outlet in written form. Tumblr was bought by Yahoo, and any time you’re bought
by a very big media company, it’s going to slow down its innovation. They need to integrate
a still very big app. Go look in the Apple top charts. It’s still well entrenched in the top 100, top 125. So I think they’re totally different. I think they’re both very
viable communication platforms that matter in society. I have the benefit, personally, of being an investor in both. Early investor in Tumblr and in Medium. Big fan of both. We spent a lot of time, you and I, jamming in Medium. So, I don’t think it’s the new Tumblr. I think Tumblr’s still there. What happened to Tumblr? I think it’s a different
animal now, and I think, depending on how you want
to communicate to the world, for example, I think Tumblr
has been a tremendous anonymous platform for people where they don’t have to be themselves and they can have pseudo
names or pseudo context or hotsaucemaster.tumblr.com is a place where you don’t have
to be necessarily your name and you can communicate to the world, and I think that really
works for a lot of teenagers and a lot of youth. Medium, people tend to be
themselves on that platform and has been a gateway for them to be discovered as great
writers or interesting writers. So they’re different, and that’s my two cents
on those two platforms, and if you’re watching this
show or listening to the show, and you haven’t played with
either platform lately, I think one of the great
things about this show is not just listening or
watching or being entertained, is to take action. And so let’s do a little
homework assignment for episode, what are we, 143? What? – [India] Three.
– Yeah, 143. I challenge you, Vayner Nation, to go out and post three things on Tumblr, if you haven’t in years,
if you never have, and to write three articles on Medium if you haven’t in a
while or you never had. I think that, to me, is the energy as we get closer to episode
200 that I wanna start doing which is I want to
create more practitioners in the amount of people that
are listening and watching to this show right now that have never created content for either
platform is stunningly high, and I want to motivate
you, right this second, to go out and do it because
you will learn from it and it will make you stronger and better and that’s something I really
wanna do out of this show. Not just entertain.

“with vulturous, unethical investors? “Would you put ’em on blast?” – Yeah, I mean, if they’re truly vulturous or unethical investors, I’m more than willing
to put them on blast, but something about this question makes me also wanna say make sure that is true. The level of thin skinness in young, first-time business people, let me just say this for the record. The audacity that is running rampant in startup land, that you’re a 22 to 24
year old entrepreneur with zero proven record, and
you’re going to the world, and you want them to give
you one million dollars at a six million dollar
valuation on your idea pisses me the fuck off, and so the answer is yes to both. I would equally put an entrepreneur that is out of their goddamn mind that has not contextualized the insanity of the
marketplace that we live in as I would as an investor
who is being vulturous or unethical and doing the wrong thing, but please recognize sitting
in this ecosystem as I am, I have had a lot of
kids come to me and say, “Can you believe this other investor “that’s part of our deal?” And when I look at it, it is very normal. I would even say, 10 years
ago, soft negotiating, but by the thin skinness
of our society right now feels aggressive to this
23-year-old idea Ricky, and so I would say absolutely,
I would put them on blast, but boy would I double check that I don’t look like an
asshole five years from now for crying about somebody
just business negotiating, and I didn’t like it
because I’ve been so used to the world giving me eighth place trophies and Mom doing my homework and having no repercussions for anything for the first 22 years of my life.