Bitcoin evangelist Michael Saylor has made $370 million from MicroStrategy stock sales this year

MicroStrategy
founder
and
bitcoin
evangelist
Michael
Saylor
entered
into
a
stock-sale
plan
with
his
company
last
summer
that
allowed
him
to
unload
up
to
400,000
shares
in
the
first
four
months
of
2024.

It
was
a
timely
agreement
for
the
59-year-old
crypto
billionaire.

With
the
plan
more
than
90%
of
the
way
to
completion,
Saylor
has
netted
about
$370
million
from
this
year’s
stock
sales,
thanks
to
the

stratospheric
rise
in
value
of
MicroStrategy,
which
is
effectively
a


bitcoin
holding
company.

Saylor,
who
started
MicroStrategy
in
1989
as
a
software
and
tech
consulting
business
and
still
serves
as
chairman,
has
emerged
as
a
bitcoin
hero
in
recent
years,

telling
CNBC
last
month
the
cryptocurrency
is
going
to “eat
gold.”
His
company
has
used
its
balance
sheet
and
tapped
the
capital
markets
to
acquire
more
than

214,000
bitcoins
since
announcing
its
strategy
to
enter
the
crypto
market
in
mid-2020.

Those
assets,
equal
to
about
1%
of
the
total
number
of
bitcoins
minted
to
date,
are
now
worth
about
$13.6
billion,
accounting
for
the
bulk
of
MicroStrategy’s
$21.3
billion
market
cap.
The
stock
has
been
a
Wall
Street
darling
of
late,
climbing
91%
this
year
—
despite
a
37%
pullback
from
its
March
high
—
after
soaring
346%
in
2023,
one
of
the

best
performers
across
the
U.S.
stock
market.

Saylor
is
the
largest
MicroStrategy
shareholder,
with
Class
B
holdings
worth
about
$2.3
billion.
At
the
end
of
2023,
Saylor
owned
another
400,000
Class
A
shares
due
to
an
option
he
received
in
2014.
Those
are
the
shares
he’s
selling
with
speed.

Buried
near
the
end
of
its

third-quarter
earnings
filing
on
Nov.
1,
MicroStrategy
announced
that
the
company
and
Saylor
had
entered
into
an
agreement,
called
a
10b5-1
plan,
in
September,
allowing
the
founder
to
sell
as
many
as
5,000
shares
every
trading
day
from
Jan.
2
to
April
25
of
this
year,
up
to
a
total
of
400,000
shares.
The
shares
were
tied
to
a “vested
stock
option,
which
expires
if
unexercised
on
April
30,
2024.”

As
of
this
week,
Saylor
has
sold
370,000
shares
totaling
$372.7
million,
according
to
filings.
His
Class
A
holdings
are
down
to
30,000
shares
as
of
the

latest
sale
disclosed
on
Thursday.

MicroStrategy
didn’t
respond
to
requests
for
comment.

Mark
Palmer,
an
analyst
at
Benchmark,
called
the
stock
sales “entirely
programmatic”
because
of
the
trading
plan
executed
last
year
and
not
at
all
a
reflection
of
Saylor’s
confidence
in
MicroStrategy
or
his
view
of
the
stock
price.

There’s
a
differing
view
in
the
retail
investor
world,
however.
Numerous
posts
on


Reddit
suggest
that
Saylor
is
perhaps
selling
for
other
reasons,
with
some
members
of
the

r/MSTR
subreddit
speculating
that
he’s
using
the
cash
to
buy
bitcoin
directly.
Some
say
they’re
selling
along
with
Saylor.
The
stock
is
down
29%
in
April,
while
bitcoin
has
dropped
11%.

Palmer,
who
has
a “buy”
rating
on
the
stock,
countered
that
such
a
point
of
view “would
be
a
misread”
by
investors
and
traders.

“What
we’re
seeing
here
is
very
straightforward
and
all
of
it’s
been
disclosed
already,”
Palmer
said. “It’s
easy
for
those
who
either
may
not
understand
the
details
or
those
who
understand
the
details
but
might
have
a
short
on
the
stock
to
twist
things
around
a
bit.
As
is
typically
the
case,
it’s
easy
enough
to
find
the
truth.” 

Even
with
the
stock
sales,
the
majority
of
Saylor’s
wealth
remains
wrapped
up
in
his
Class
B
holdings
of
MicroStrategy,
along
with
the
17,732
bitcoins
he
purchased
in
2020
that
are
currently
worth
about
$1.1
billion.

Much
of
the
rally
in
bitcoin
and
related
investments
has
to
do
with
the
emergence
of

bitcoin
exchange-traded
funds,
which
received
regulatory
approval
earlier
this
year,
and
the
upcoming

halving
this
week.
The
technical
event
happens
every
four
years,
cutting
rewards
for
bitcoin
miners
in
half
and
reducing
the
pace
at
which
new
bitcoins
enter
the
market.

In
a
market
where
consumers
can
buy
bitcoin
directly
on
various
exchanges
or
choose
a
host
of
new
ETFs,
Saylor
has
said
the
ongoing
advantage
of
MicroStrategy
is
that
it’s
a
leveraged
bitcoin
play
without
the
management
fee.
The
company
can
raise
money
to
go
deeper
in
crypto,
and
last
month
said
it

reeled
in
$782
million “to
acquire
additional
bitcoin.”
The
cash
came
from
a
convertible
debt
sale
at
0.625%
interest.

“Is
there
any
company
in
the
world
that
you
wouldn’t
like
to
invest
in
that
could
borrow
$1
billion
at
less
than
1%
interest
to
invest
in
your
best
idea?”
Saylor
said
on
CNBC’s “Squawk
Box”
in
March.
He
added
that
the
company’s
leverage
leads
to
volatility,
which “attracts
capital,
and
we
can
then
leverage
more.”

Benchmark’s
Palmer
said
there
are
plenty
of
reasons
to
remain
bullish
on
MicroStrategy,
especially
with
the
halving
just
around
the
corner.
Following
past
halving
events,
the
price
of
bitcoin
has
jumped.

“If
I
were
in
a
situation
where
I
had
shares
in
MicroStrategy,
this
is
time
where
I’d
very
much
want
to
be
holding
on
to
them,”
Palmer
said.