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June 27, 2025 8 mins

Loeb Enterprises II President, CEO, & Founder Michael Loeb joins Bloomberg's Carol Massar and Tim Stenovec from the Uncharted Annual Summit in Southampton, New York. They talk entrepreneurship in the fintech space.

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Speaker 1 (00:02):
Bloomberg Audio Studios, Podcasts, Radio new We saw that with
the stocks pairing games today.

Speaker 2 (00:09):
It's just a reminder that when we think we can't
be surprised, we still can as certainly as investors, and
that plays out the markets react very quickly, very swiftly,
and you can see that clearly in the trade. All right,
you are listening and watching Bloomberg BusinessWeek Daily, Carol Master,
Tim's Stanevik life here and I believe we can go
to our guest. We're doing this at a real time.
You guys are seeing the sausage be made. Michael Lobe

(00:31):
is with us. This is his home, this is his event.
He's the founder and CEO of lob dot NYC, and
he co founded Uncharted a few years ago, and I
got to talk to you this morning. So I feel
kind of doubly blessed to get some more time with you.
The event is underway. Tell us about what you're hearing
some of the things so.

Speaker 3 (00:48):
Far, well, I think that there's a great deal of buzz.
Most people are saying exactly what you are, which is
that they're doubly blessed just to be here and get
to know everybody else. But I mean, the if you
were to take a look at the background, you would see,
you know, six hundred people talking to six hundred other people.

(01:12):
It's quite the event. And what we really want to
do is foster relationships between investors and companies, between companies
and companies, and between you know, CEOs looking for talent
and talent looking for CEOs. So I think I think
a good time is being had by all. And certainly

(01:34):
the weather has been totally cooperating. I think you had
something to do with that, So I thank you for that.
You're very welcome, right So, yeah, little tiny Wendy, if
you could take that down.

Speaker 1 (01:45):
It's just kind of perfect. It beats the weather we
had earlier this week. I was a little concerned about that.
You know, an event like this, you've been doing this
for a few years, started during the pandemic, started a
lot smaller. How do you And I heard you say
earlier today and your partner say this too, Noah, that
he is running into people constantly. You say, yeah, they
raised money as a result of being here. They found
a co founder here, they found employees here. How do

(02:08):
you measure the success of an event such as this
In the days, weeks and months following.

Speaker 3 (02:12):
It, right, I wish we could because I should have
a big on all that.

Speaker 1 (02:16):
Yes, so we were just talking to Damon John like
you know, shark tank kind of thing. Yeah, maybe you
could kind of get in on that.

Speaker 3 (02:21):
I don't know it for a long time. So, you know,
I got to tell you we do solicit testimonials of
exactly the things that you're talking about. We have quite
a few of people saying, you know, I met my
founder there about two years ago. Uh no, and I
get an invitation and who was shrouded in mystery? And

(02:44):
it was three women who had us go to an
event downtown and they brought us up on stage. Everybody
started a clap, And what that was is these were
three women never met before. They were all, you know,
elite athletes, and they decided they're should be a fund
supporting elite athletes that they had a different point of view,

(03:06):
a different sense of how to compete, and they all
got along very very well, and that thesis led to
a fifty million dollar fund. So it's that type of
thing that you know, really propels us.

Speaker 2 (03:17):
Well, talk to us about you know capital, how much
is out there for startups?

Speaker 3 (03:20):
Wow? You know It's funny things go in cycles. As
you know, this is not an up cycle for capital formation.
Last numbers I looked at and they're a little bit stale,
but you know, down sixty or seventy percent. Certainly the
secondary market, if that's any indication at all, does illustrate that,

(03:42):
you know, there's a lot of illiquidity looking to get liquid.
Not nearly as frothy as it used to be was IPOs,
even though that's starting to unlock a little bit. So No,
it's it is hard and the money does gravitate these
days to AI, so you need, you know, if you have.

Speaker 2 (04:01):
So when there is an idea, when there is a startup,
that's where it goes.

Speaker 3 (04:04):
It goes there, right. And what folks don't I think,
really realize or appreciate is the forces at play in
venture and venture funding, venture capital, which is I sometimes
call it a beauty contest, and that is because there's
one breakout winner in a category and then all the

(04:25):
LPs are asking their gps, you know, what is your
AI strategy? And if the answer is, you know, we
think it's a little over sold, we think it's a
little bit you know, frothy. Whereas there's going to be
a couple of winners and a lot of losers. We're
taking a wait and see attitude. The answer is bye bye.
I'm bringing my money to that fund that made that investment.

(04:46):
So a lot of pressure for them to jump in.
And it's in those situations that you know, not so
good deals are made.

Speaker 1 (04:55):
Right, So yeah, does it you know, in terms of cycles,
does it feel like this AI cycle is different than
previous tech hype cycles? And the reason I ask and look,
nobody wants to hear or utter the phrase this time
is different. But if you look out at the private
markets right now, you've got skyhad evaluations. I think many
would argue for open AI right, for anthropic, for perplexity.

(05:17):
You have meta platforms coming in and dropping billions of
dollars to buy forty nine percent of an AI company
that barely existed. You have founders being poached. We're talking
one hundred million dollar signing bonuses force an individual to
go to a large company.

Speaker 3 (05:33):
Right, So I'm I look at my mailbox every day,
I'm looking for one hundred million dollar check hasn't come
in yet, Right, So if you're going to range.

Speaker 1 (05:40):
You know, you know, make make your web your web
browser or your you know, your website dot ai and
maybe it'll happen.

Speaker 3 (05:47):
I don't know that. So to me, and this is
not quite answering your question, but I'm it's all about me,
So I'm going to answer it from my perspective, which
is that to me, it feels different. Now, what does
it feel like? I've been around for long enough, so
I'm something of the elder statement statesman here. I've been

(06:08):
around long enough that I've seen a few cycles. This
feels like the late nineties and the late nineties was
the advent of the internet, right, and it feels this
profound now. You know, people can say, well, you know,
if we look back two or three years, it was
NFTs and that was a false positive, and before that
it was blockchain, which was sort of a false positive.

(06:30):
And before that it was cannabis, and before that it
was bitcoin. But this one feels real, and this has
the possibility of disrupting entire industries. I had breakfast, by
the way with a friend this past week. He has
a unicorn business is worth almost two billion dollars. He
has two hundred and seventy people, and he said, Michael,

(06:53):
by year end it's one hundred and twenty.

Speaker 1 (06:55):
Meaning he is going to lay people off because AI
has been selefficient.

Speaker 3 (06:59):
Right, fast growing company, super fast growing company.

Speaker 1 (07:02):
That's really scary, I know, but that's what's going on.
And so do you think so do you think there
is something? Do you think there is something to what
Dario Amadae has said, who's the founder of Anthropic. Among
the co founders of Anthropic, there are many that in
a couple of years we're going to see a serious
uptick in unemployment as a result of this tech, like

(07:23):
this is something policymakers need to be freaking out about
right now.

Speaker 3 (07:26):
Yeah, well, look, I respectfully disagree, and all I have
to go on is history and starting in the seventeen hundreds,
right when there was that industrial revolution in England, and
we've burned down all the factories with a spinning wheel,
thinking everybody would be unemployed. That has not happened, but
markets employment people have an amazing ability to retrain themselves

(07:49):
find the opportunities. In the end, I think we're going
to be okay. Is there going to be some displacement.
There's always some displacement. I hope you find out find
something that we can have less lawyers because we'd use
less wars. But I think at the end of the day,
you know, brilliant people are going to find find their way.
And the people you're talking about are very smart people, engineers.

(08:12):
They will find their way. We're always going to need them.
And you know, this is going to be like every
other labor saving prediction. This is going to be just
another one.

Speaker 2 (08:21):
All right, We're gonna unfortunately have to leave it there.
But thank you for inviting us. This has been fun.

Speaker 3 (08:26):
Thank you for inviting me. Guys, I believe this is yours.
Oh that's not what they told me. They said after today,
it's all yours. That's not right, Michael, so nice.

Speaker 2 (08:39):
Oh the key is please Michael Lowe, founder and CEO
of Lobe dot NYC. All right, coming up next, we're
also going to get to I guess I want to
say almost another serial entrepreneur, another biggest
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