Episode Transcript
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Speaker 1 (00:00):
Before we start, tell me where you're listening from in
the comments. Maybe you're someone who's faced rejection and wondered
what if. Maybe you're curious about how setbacks shape us
differently than success does. Maybe you're wondering what it feels
like to encounter someone from your past after your life
has completely transformed. This conversation is for you. Twenty eight
(00:22):
years ago, when I was a twenty six year old
with big dreams but an empty bank account, I met
someone who would teach me one of the most important
lessons of my life, not through acceptance or encouragement, but
through rejection so complete and devastating that it changed how
I understood myself, success, and what really matters in relationships.
(00:45):
Her name was Sarah, and for six months in nineteen
ninety six, I thought she might be the person I'd
spend my life with. I was wrong about that, but
I was right about something else. The experience would shape
everything that came after.
Speaker 2 (00:58):
Today.
Speaker 1 (00:59):
I want to sh share the story, not to embarrass
anyone or settle old scores, but because I think it
reveals something important about human nature, the role of rejection
in building character, and why the timing of when people
enter and exit. Your life matters more than we usually admit.
In nineteen ninety six, I was nobody special by conventional standards.
(01:21):
I had recently dropped out of Stanford's PhD program to
start a company with my brother called zip Too. We
were living in a tiny office, showering at the YMCA,
and eating more Ramen noodles than any human should consume.
I was passionate about the Internet's potential, convinced that we
were building something revolutionary. But I had no money, no
social status, and no evidence that my crazy ideas would
(01:45):
ever amount to anything. To most people, I looked like
another tech dreamer who would probably flame out within a year.
I met Sarah at a coffee shop in Palo Alto.
She was a graduate sudent in psychology at Stanford, brilliant, beautiful,
and came from the kind of established East Coast family
(02:06):
where success was measured in generations, not startups. She had
that effortless confidence that comes from never having to worry
about basic survival, never having to prove your worth to
skeptical investors or sleep on office floors. I was immediately smitten,
not just with her looks, though she was stunning, but
(02:26):
with her intelligence, her dry sense of humor, and the
way she could discuss complex ideas with the kind of
casual expertise that I envied. She seemed to represent everything
I wanted to become, sophisticated, cultured, connected to a world
of ideas and influence that felt miles away from my
South African childhood and my current hand to mouth existence.
Speaker 2 (02:50):
For three months, we.
Speaker 1 (02:51):
Dated in the way that broke graduate students and startup founders.
Date coffee instead of dinner, long walks instead of expensive entertainment,
hours of conversation about technology, psychology, philosophy, and the future
we thought we were building. I thought it was romantic.
I thought our financial limitations forced us to connect on
a deeper level, to focus on ideas and dreams rather
(03:13):
than material experiences. I thought she appreciated my passion for
changing the world, even if the world hadn't yet recognized
what I was trying to do. I was wrong about
almost everything. Sarah was polite about my circumstances, but I
started to notice things. How she would change the subject
when I talked about Ziptoo's potential, How she would compare
(03:34):
my situation unfavorably to her friends who were pursuing traditional
career paths. How she seemed embarrassed when we encountered her
Stanford's social circle and she had to explain what I
did for a living. The turning point came when I
invited her to a dinner party hosted by.
Speaker 2 (03:52):
One of my early investors.
Speaker 1 (03:54):
It was my first real opportunity to introduce her to
the world I was trying to build, to show her
that even though I was broke, I was connected to
people who believe in the future I was working toward.
She spent the entire evening making polite conversation while clearly
wishing she was anywhere else. Afterwards, she said the people
were interesting in that tone that meant exactly the opposite.
Speaker 2 (04:15):
She asked why I was.
Speaker 1 (04:17):
Wasting my time with these tech people when I could
be doing something more substantial with my life. That's when
I realized we weren't just from different economic backgrounds. We
had fundamentally different values about risk, ambition, and what constituted
a meaningful life. Despite the growing tension, I convinced myself
that our relationship could work.
Speaker 2 (04:36):
I was in love, or.
Speaker 1 (04:37):
Thought I was, and I believed that love could bridge
any gap in understanding or values. After six months of dating,
I decided to take the biggest risk of my young life,
not just emotionally but financially. I spent two thousand dollars
money I absolutely could not afford on an engagement ring.
(04:58):
This represented weeks of person expenses, money that should have
gone toward keeping Zip to alive. I planned what I
thought was the perfect proposal, a picnic in the hills
overlooking Silicon Valley, the place where I was convinced we
would build our future together. I had prepared a speech
about how I might not have much to offer her now,
(05:19):
but I was committed to building something significant, not just
for myself, but for us.
Speaker 2 (05:26):
I never got to give that speech.
Speaker 1 (05:27):
When I showed her the ring and started to explain
my feelings, she stopped me before I could finish. Not gently,
not with the kind of caring rejection that preserves dignity.
She looked at me like I had just suggested something
absurd and slightly offensive. Elon, she said, I care about you,
(05:50):
but I need to be realistic about my future. I
can't build a life with someone whose biggest accomplishment is
a website nobody's heard of.
Speaker 2 (05:59):
I needs to build it. I need security.
Speaker 1 (06:02):
I need someone who's already proven they can succeed in
the real world. She went on to explain that while
she found my entrepreneurial spirit admirable, she couldn't take seriously
the idea of marrying someone who might never amount to anything.
She had goals for her life a nice house, financial security,
social status, a partner her family could respect, and I
(06:24):
simply didn't fit into that picture. The rejection was clinical, thorough,
and devastating. She didn't just say no to the proposal,
she dismissed the entire premise that I might ever become
someone worth saying yes to. I drove home in a daze,
the ring in my pocket feeling heavier than any rocket
I would ever build. I sat in my tiny apartment,
staring at the symbol of hopes that had just been obliterated,
(06:49):
and experienced what I can only describe as a complete
emotional collapse. For about three days, I questioned everything.
Speaker 2 (06:57):
Was she right?
Speaker 1 (06:59):
Was I deluding myself about Ziptu's potential? Was I wasting
my life chasing impossible dreams when I should be pursuing
traditional career paths that would provide the stability and respect
that clearly mattered to people I wanted to impress. But
then something shifted. The hurt began to transform into something else. Determination,
not the petty kind of determination that seeks revenge, but
(07:21):
the deeper kind that seeks vindication. Not vindication for her,
but for the values and vision she had rejected. I
realized that Sarah's rejection wasn't really about me personally. It
was about what I represented. I represented uncertainty, risk, the
possibility of failure. She wanted guarantees that I couldn't provide,
(07:43):
not because I lacked commitment or capability, but because the
future I was trying to build didn't yet exist. Her
rejection clarified something crucial. I needed to find people who
could believe in possibilities before they became realities. People who
could see potential rather than just current circumstances. People who
(08:03):
are excited by the uncertainty of building something new rather
than threatened by it. I won't lie and say her
rejection didn't motivate me.
Speaker 2 (08:12):
It did.
Speaker 1 (08:13):
Every time Ziptu faced a crisis, and there were many.
I thought about Sarah's dismissive tone, her certainty that I
would never amount to anything, not because I wanted to
prove her wrong, but because I wanted to prove that
her criteria for evaluating people were wrong. She had judged
my worth based on my current financial status rather than
(08:36):
my future potential. She had valued security over ambition, conformity
over innovation, established success over pioneering effort. These weren't just
personal preferences. They were fundamental disagreements about what makes life meaningful.
Her rejection taught me that some people can only love
you after you've succeeded, not while you're struggling to succeed.
(08:57):
That some people need social validation of your worth before
they can recognize it themselves. That some people are attracted
to the fruits of achievement but repelled by the process
of achieving. This became a filter for every relationship that followed,
not a test of gold digging or superficiality, but a
deeper question. Can this person love the person I am
(09:20):
when I'm building something uncertain, or do they only love
the person I become after I've built it. Two years later,
Ziptu was acquired by Compac for three hundred seven million dollars. Overnight,
I went from broke entrepreneur to multimillionaire. The transformation was surreal,
not just financially but socially. Suddenly people who had dismissed
(09:43):
my ideas were calling them visionary. Women who had found
my circumstances unappealing now found them fascinating. I started PayPal,
which sold to eBay for one point five billion dollars,
then Tesla, then SpaceX, then a dozen one other ventures
that grew my net worth into the hundreds of billions.
(10:03):
Each success validated not just my business instincts, but my
conviction that the future belongs to people willing to risk
comfortable presence for extraordinary possibilities. But success also revealed something
troubling about human nature. Many of the same people who
had been skeptical or dismissive during my struggling years now
(10:24):
claimed to have always believed in my potential. They rewrote
history to position themselves as early supporters rather.
Speaker 2 (10:31):
Than late converts.
Speaker 1 (10:33):
This revisionism wasn't malicious, it was psychological self protection. Nobody
wants to admit they lacked the vision to recognize potential
before it became obvious. But it taught me to be
very careful about who gets credit for believing in me
and when that belief actually began. In two thousand and eight,
twelve years after her rejection, I encountered Sarah again at
(10:55):
a Stanford alumni event. I was there as a donor
and speaker. She was there as an alum and psychologist
with a successful private practice. The interaction was awkward in
ways that neither of us had anticipated. She approached me
after my speech, clearly nervous, and attempted to resume our
(11:15):
relationship as if the rejection had never happened. She mentioned
how she had always admired my ambition and had followed
my success with interest over the years. I was polite,
but distant, not because I harbored resentment. I was genuinely
grateful for the lesson her rejection had taught me, but
because I recognized that her renewed interest wasn't really about
(11:38):
me as a person.
Speaker 2 (11:39):
It was about me as a symbol of success, wealth,
and status.
Speaker 1 (11:45):
She had learned that I was worth two billion dollars
at that point, and suddenly all her previous concerns about
stability and security seemed to have evaporated. The same uncertainty
and risk taking that had made me unsuitable twelve years
earlier now made me fascinated. During our brief conversation. She
made several references to how different she was now, how
(12:07):
she had developed more appreciation for entrepreneurial spirit and had
come to understand that traditional paths aren't the only roots
to success. She seemed to be auditioning for a role
in my life, rebranding herself as someone who could appreciate
the journey, not just the destination. But I knew better
people don't fundamentally change the values in their thirties. She
(12:29):
had learned to appreciate successful entrepreneurs, not struggling ones. She
had developed tolerance for calculated risks that had already paid off,
not faith in uncertain ventures that might fail. The conversation
was cordial but brief. I wished her well in her
practice and her life, and we parted ways. I haven't
spoken to her since, though I occasionally hear updates through
(12:51):
mutual acquaintances. Sarah's rejection taught me several lessons that shaped
how I approach relationships, both personal and profit. First timing
matters enormously in human connections. People enter and exit our
lives when we need them to, not when we want
them to. Sarah rejected me exactly when I needed to
(13:14):
learn that external validation isn't necessary for internal worth. If
she had accepted my proposal, I might have become dependent
on her approval rather than developing my own conviction. Second
rejection often reveals incompatible values, rather than personal inadequacy. Sarah
wasn't wrong for wanting security and stability. Those are legitimate desires.
(13:36):
But I needed someone who could find security in shared
purpose rather than external circumstances, who could find stability in
mutual commitment rather than financial guarantees. Third love requires faith
and potential, not just appreciation. For actualization, the right person
for me would need to love the person I was becoming,
(13:57):
not just the person I had already become. Need to
see possibilities that others couldn't see, to believe in dreams
that others found unrealistic. Fourth, success changes how people perceive
your past, not just your present. Once I became wealthy,
many people retroactively decided that my early struggles were visionary
(14:17):
rather than foolish. This taught me to be skeptical of
people who claimed to have always believed in me, especially
if their support only became vocal after my success became obvious.
I'm genuinely grateful to Sarah. For rejecting me, not in
a petty look what you missed way, but in a
(14:39):
deeper sense of appreciation for the clarity her rejection provided.
Speaker 2 (14:44):
If she had said yes, I.
Speaker 1 (14:45):
Might have spent years trying to conform to her vision
of success rather than pursuing my own. I might have
chosen safer past to prove my worthiness to someone who
valued security over innovation. I might have become successful in
conventional terms while abandoning the unconventional dreams that eventually define
my life. Her rejection forced me to clarify my values,
(15:08):
to choose between approval and authenticity, between fitting in and
standing out. It taught me that the right person would
be attracted to my ambition rather than threatened by it,
excited by uncertainty rather than paralyzed by it. More importantly,
it told me that rejection can be redirection. When someone
says no to you, they're often saying no to a
(15:29):
version of yourself that wouldn't have served your highest purpose anyway.
The person who rejects you for your lack of conventional
success is probably not the person who would celebrate your
unconventional achievements. Sarah's rejection was part of a larger pattern
I've observed throughout my life. People's ability to see potential
as directly related to their tolerance for uncertainty. Those who
(15:50):
need guarantees before they invest emotionally are rarely the ones
who helped create the extraordinary. This applies to business partnerships, friendships,
romantic relationships, and even family dynamics. The people who believe
in you when you're unknown are fundamentally different from those
who believe in you after you're proven. Both serve purposes,
but only the first group can walk with you through
(16:12):
the valley of uncertainty that precedes every meaningful achievement. This
doesn't make either group better or worse morally, but it
does make them suitable for different roles in your life.
Sarah was honest about her limitations. She couldn't invest in potential,
only in actualized success. That honesty, while painful at the time,
was actually a gift. Twenty eight years later, I think
(16:35):
about Sarah whenever I meet someone new, whether in business
or personal contexts, not because I'm comparing them to her,
but because she taught me to recognize the difference between
people who can love you through uncertainty and people who
can only love you after certainty. This lesson has served
me well in choosing business partners, investors, employees, and friends.
(16:57):
The best relationships in my life have been with people
who saw something in me before the world did, who
bet on potential rather than proven results, who were excited
by possibilities rather than intimidated by them. Sarah couldn't be
that person for me, and that's okay. She found someone
who could provide the security and stability she needed, and
(17:19):
I found people who could provide the faith and vision
I needed. We were incompatible, not inadequate. Her rejection taught
me that the right people will see your value before
the world validates it, will believe in your dreams before
they become reality, will love the person you're becoming more
than the person you've already been. If you're facing rejection
(17:39):
right now, whether romantic, professional, or personal, consider the possibility
that it's not about your inadequacy but about incompatible values
or timing. Ask yourself, is this person rejecting who you
are or who you're not yet but could become. If
someone can only appreciate you after you've succeeded, they probably
(18:00):
weren't meant to walk with you through the process of succeeding.
If someone needs external validation of your worth before they
can recognize it, they probably aren't equipped to provide the
internal validation that sustains you through difficult times. This doesn't
make rejection painless, but it can make it purposeful. Every
no can redirect you tord yes that actually serves your growth.
(18:24):
Every person who can't see your potential can clear space
for someone who can. The goal isn't to prove rejectors wrong.
It's to prove your own vision right. The goal isn't
to make them regret their decision. It's to make yourself
grateful for the clarity it provided. Sarah rejected me before
I was a billionaire, and I'm glad you did not
(18:44):
because her rejection motivated my success.
Speaker 2 (18:47):
My success was motivated by much.
Speaker 1 (18:48):
Deeper purposes, but because her rejection revealed our fundamental incompatibility.
Before I committed my life to someone who couldn't appreciate
the journey, only the destination. Twenty eight years later, I
can say with complete honesty that she made the right
decision for both of us. She needed someone who could
provide immediate security and conventional success. I needed someone who
(19:12):
could embrace uncertainty. And unconventional dreams. We both found what
we were looking for, just not with each other. Her
rejection taught me that the right person doesn't just love
who you are, They love who you are becoming. They
don't just appreciate your current achievements, they believe in your
future potential. They don't just accept your dreams, they share them.
(19:34):
Sarah couldn't be that person for me in nineteen ninety six,
and that's the greatest gift she ever gave me, because
it forced me to become the kind of person who
could eventually find and recognize that right person when they appeared.
Rejection isn't always personal failure. Sometimes its divine redirection toward
something better suited for who you are meant to become.
(19:56):
Share this with some one who needs to hear that
rejection can be protection, that timing matters more than we realize,
and that the right people will see your value before
the world validates it. Subscribe If these conversations help you
think differently about setbacks and relationships, and remember the person
who can't love you through uncertainty probably isn't meant to
(20:17):
celebrate your certainty. What rejection in your life turned out
to be a redirection towards something better,