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