“Don’t embarrass me,” my sister hissed into the phone, her voice sharp with that familiar edge of condescension I’d heard my entire life.
“Dererick works for Nexer AI. They’re worth billions. His colleagues will be at dinner tonight, and I need you to just blend in. Can you do that for once?”
I sat in my apartment looking out at the San Francisco skyline, my coffee growing cold in my hand.
“Sure, Amanda. I can blend in.”
“Good. And please, for the love of God, don’t talk about your startup thing. Nobody wants to hear about another failed tech venture. Dererick’s colleagues are actual professionals.”
I said nothing. What was there to say? Amanda had been my older sister for 32 years, and in all that time, she’d never once asked what I actually did for a living. She decided my story when I was 23 and working out of a garage. And that story had never updated in her mind, no matter how many times I tried to tell her otherwise.
“Why? Are you listening?”
“I’m listening.”
“7:00 at Prospect. I’ll be there. And wear something nice. Not those jeans you always wear. Derek’s VP of product development. His boss might even show up. These people matter.”
The call ended. I looked down at my phone, then at my laptop, where three acquisition offers sat in my inbox, each one north of $800 million. I’d been fielding calls from Goldman Sachs all week about our IPO timeline. Tomorrow, I had a meeting with our lead investors about expanding into the European market, a move that would push our valuation past 2 billion. But to Amanda, I was still the family disappointment playing with computers in a garage.
I arrived at Prospect at 6:55 p.m., deliberately early. The restaurant was the kind of place where tech money met old money, where deals got made over Wagyu and wine that cost more per bottle than most people’s monthly rent. I’d eaten here two dozen times, usually with investors or board members. Tonight, I was here as Amanda’s charity case of a little sister. She spotted me immediately, her face doing that thing it always did, a quick scan of my outfit, a microscopic frown, a resigned sigh. I’d worn black slacks and a silk blouse, but clearly it wasn’t enough.
“You’re here,” she said, kissing the air beside my cheek. “Dererick’s running a few minutes late. Big meeting, you understand?”
“Of course.”
We sat at a table for six. Amanda’s hands were nervous, adjusting her napkin, checking her phone, reapplying lipstick. I recognized the anxiety. She’d always cared desperately about what people thought, about her position in whatever social hierarchy she’d constructed in her mind.
“So,” she said, not quite meeting my eyes, “how’s the job search going?”
“I’m not looking for a job.”
“Right. Right. Your startup. How’s that going? Still just you and a couple of guys in a garage.”
I took a sip of water.
“Something like that.”
“You know, it’s not too late to get a real job. Dererick says Nexer is always hiring. Maybe something in marketing or operations. Entry level, but it’s a foot in the door.”
“That’s kind of you to think of me.”
She leaned forward, lowering her voice.
“I’m serious, Maya. You’re 30 years old. You can’t keep playing entrepreneur forever. Mom and dad are worried sick.”
Before I could respond, Dererick arrived with three colleagues. He was exactly what I’d expected. Confident, bordering on arrogant, expensive suit, handshake that lasted two seconds too long. His colleagues were similar. Successful, self-assured, eager to talk about Nexra’s latest product launch.
“Everyone,” Amanda said, her voice bright with pride, “this is my sister Maya.”
“Nice to meet you,” I said, shaking hands.
“La is between things right now,” Amanda continued. And I watched her weave the narrative she needed, figuring out her next move. “But I keep telling her, Nex is always hiring.”
The colleague smiled politely. Derek launched into a story about their latest AI model, how they’d secured a contract with three Fortune 500 companies, how the company was on track to hit a billion in revenue next year.
“We’re revolutionizing enterprise AI,” he said, and I could hear the talking points he’d memorized. “Our CO is brilliant. She’s taking us public next year. This is the ground floor of something massive.”
“That sounds exciting,” I said.
Throughout dinner, I listened. Derek talked about quarterly targets and product road mapaps. His colleagues discussed the competitive landscape, how they were beating out smaller startups, how the market was consolidating, how only the big players would survive.
“These tiny companies,” one of them said, laughing, “they think they can compete. It’s cute, really. They don’t understand enterprise sales. They don’t have the infrastructure.”
Amanda glanced at me nervously, and I knew what she was thinking. That I was one of those cute doomed startups. I smiled and asked intelligent questions, playing the part she needed me to play.
Dererick’s phone buzzed during dessert. He glanced at it and his face shifted into something more serious.
“That’s the CEO. Board meetings been moved to Monday morning, 9:00 a.m. sharp. All executives required.”
“On a Monday,” one of his colleagues groaned. “She doesn’t mess around. If she calls a meeting, it’s important.”
Derek turned to Amanda, squeezing her hand.
“Babe, I might need to prep all day Sunday.”
“Of course,” Amanda said. “Whatever you need.”
As dinner wound down, Amanda walked me to the valet stand.
“Thank you for coming,” she said. “And for not, you know, not what not making it weird. Dererick’s colleagues are important. His career is really taking off.”
She paused.
“I know you don’t understand this world, but appearances matter. The people you associate with, the impression you make, it all matters.”
I looked at my sister, really looked at her. She was 2 years older, but sometimes the gap felt like decades.
“I’m happy for you, Amanda. Derek seems nice.”
“He is. He’s going places. VP now, but his boss loves him. Could be seuite in 2 years.”
She lowered her voice.
“That’s the kind of stability you should want, Maya. Not this startup lottery ticket nonsense.”
The valet brought my car, a Tesla Model S, 3 years old, paid in cash. Amanda didn’t comment on it. He never did. I think she’d convinced herself it was leased or that I’d gotten some kind of deal.
“See you at mom and dad’s next week?” she asked.
“I’ll be there.”
I drove home through streets I knew well. Past the office buildings where I’d taken hundreds of meetings, past the coffee shops where I’d sketched out product ideas on napkins. Past the garage where this had all started 7 years ago. Seven years. That’s how long it had been since I’d left my job at Google to start Nexra AI. Yes, Nexra. The same company Derrick worked for. The same company Amanda thought was too prestigious for her disappointment of a sister to even understand. I’d founded it with two MIT classmates when I was 23. We’d bootstrapped for 8 months, living on ramen and determination before landing our first angel investment, then a seed round, then series A, B, C. We’d grown from three people to 800. We’d gone from one product to a full enterprise suite. We’d gone from hoping to make rent to turning down acquisition offers from Microsoft and Salesforce. And through it all, I’d never told my family, not because I was hiding it, because they’d never asked, because every time I tried to explain, they talked over me, changed the subject, or offered me career advice for jobs I didn’t need. My father thought I did something with computers. My mother told her friends I was still figuring things out. Amanda had decided I was a failure and no amount of evidence would change her mind. So, I’d stopped trying. I’d learned to blend in, to nod along, to let them believe whatever made them comfortable.
But Monday morning was going to be interesting.
I spent Sunday preparing for the board meeting. We had serious decisions to make, whether to accept Goldman’s IPO timeline, how to structure our European expansion, whether to acquire two smaller competitors or let them die on the vine. I reviewed the deck our CFO had prepared, made notes on the financials, and confirmed attendance with all board members. This wasn’t just any meeting. We were discussing the future of a company that now employed 847 people and held contracts with 60% of the Fortune 100. My executive assistant had confirmed everyone’s attendance, including the six new members of our leadership team who’d been hired in the past quarter. Derek Chin, VP of product development, had been with us for 3 months. His hiring had been my COO’s call. Derek had come from IBM with strong credentials and a track record of successful product launches. I’d met him briefly during his final interview, but he’d been nervous, focused on the COO and CTO. I’d asked three questions, nodded at his answers, and let my team make the final decision. We hired him a week later. He had no idea who I was.
Why would he? I was just another person in the interview room, another face in the building. He’d never asked my name. He’d certainly never connected me to Amanda. And Amanda had never connected Dererick’s new job to her sister’s startup thing.
Monday morning arrived with typical San Francisco fog. I dressed in my usual board meeting outfit, tailored black suit, white silk blouse, minimal jewelry. My driver picked me up at 7:30 a.m., giving me time to review notes during the 30inut ride to our headquarters in Soma. The building was sleek glass and steel, 14 floors of it, with our logo emlazed across the top. Nexer AI in letter 6 ft tall. We’d moved here 2 years ago, upgrading from our previous space when headcount had hit 400.
I took my private elevator to the 14th floor where the executive offices and main boardroom were located. My assistant Jennifer was already at her desk.
“Morning Maya. Coffeey’s ready. The boards arriving at 8:45. Full attendance confirmed including the new executives.”
“All six confirmed?”
“All six confirmed. Derek Chin asked if he should prepare anything. I told him just to review the product road map slides.”
“Perfect. Thanks, Jennifer.”
I settled into my office, which occupied the northwest corner with views of the Bay Bridge. The walls held my diplomas, BS and MS from MIT, MBA from Stanford, several awards from industry organizations, a framed Forbes cover from 2 years ago, the 30 under 30 revolutionizing AI, and photographs from our company’s history, the original garage, our first office, the series B celebration, the ribbon cutting for this building.
At 8:50 a.m., I walked to the boardroom. Our board members were settling in, two venture capital partners who’d led our series B, our CFO, our CTO, our general counsel, and three independent board members with expertise in enterprise software. The new executives sat together at one end of the long table looking nervous. This was their first board meeting, their first real exposure to how decisions got made at this level. Derek was among them, talking quietly with our VP of sales. He wore a sharp navy suit and looked confident, though I could see the slight tension in his shoulders.
I took my seat at the head of the table. Jennifer dimmed the lights slightly and pulled up the presentation on the large screen.
“Good morning, everyone,” I said. “Let’s get started.”
I watched Dererick’s face as I spoke, watched the exact moment he realized who I was. His eyes went wide, his mouth opened slightly, the color drained from his face. Arcio Marcus leaned over and whispered something to him. I couldn’t hear it, but I could imagine that’s Army Maya Chin. Dererick’s hands gripped the armrests of his chair. He looked like he might be sick.
I continued with the meeting agenda, professional and focused.
“We’re here to discuss three major items. The IPO timeline, European expansion, and potential acquisitions. Let’s start with the financials.”
Our CFO, Patricia, walked through the numbers. Revenue was up 340% year-over-year. We were profitable in three of our four divisions. Our cash reserves were strong. Goldman Sachs was projecting an IPO valuation between $210 and $2.4 billion.
“We have a decision to make,” Patricia said. “Go public in Q2, which is aggressive but captures market momentum, or wait until Q4, which gives us time to strengthen our enterprise division numbers.”
The board members discussed the options. I listened, asked questions, pushed back on assumptions. This was the work I loved. The strategic thinking, the calculated risk-taking, the building of something that mattered. Dererick hadn’t said a word. He sat frozen, staring at me like I was a ghost.
We moved to the European expansion proposal. Our VP of international sales presented the plan. Offices in London, Berlin, and Paris with a target of 200 European clients within 18 months.
“The investment is significant,” I said, studying the numbers. “47 million euro over 2 years, Marcus. Is our technology ready for EU data compliance requirements?”
“We’ve been working on GDPR compliance for 6 months,” our CTO replied. “We’re ready.”
“Then I’m in favor. Board.”
Six hands went up. The motion carried.
Finally, we discussed acquisitions. Two smaller AI companies were struggling, both with technology that complemented ours. We could acquire them for a combined $140 million, our general counsel said. Or we could wait for them to fail and hire their engineers for significantly less.
“What’s the ethical play?” I asked.
The room went quiet. This was something I’d learned from my mentor at Google. Profit mattered, but so did how you made it.
“The ethical play is to acquire them,” Patricia said slowly. “Keep their teams intact, preserve their technology, honor their vision, even if it costs more.”
“Then that’s what we do. Draft the offers, be generous with the founders. They built something valuable even if the market didn’t cooperate.”
The meeting continued for another hour. We discussed product road maps, competitive threats, talent acquisition. Dererick’s team presented updates on the new AI model they’d been developing. It was solid work, I noted. He might be personally disastrous, but he wasn’t incompetent.
As the meeting ended, people gathered their materials and headed out. The new executives clustered together, clearly overwhelmed by their first board meeting. Dererick approached me slowly like he was walking toward a firing squad.
“Miss Chin,” he said, his voice barely steady, “I… I didn’t realize that I was the CEO.”
I kept my voice neutral.
“Most people don’t unless they read tech news. You’ve been doing good work, Derek. The new model launch is ahead of schedule.”
“Thank you. I…”
He swallowed hard.
“I met your sister, Amanda. I know she’s mentioned you. She never said… I mean, she told me you were between jobs figuring things out.”
I smiled slightly.
“Amanda has her own narrative. I don’t correct her.”
“But you founded this company. You built all of this…”
“With a lot of help. We’re a team here.”
He looked like he wanted to say more, but Marcus called him over to discuss the product road map. Derek glanced back at me once, then walked away, his shoulders slumped.
I returned to my office and pulled out my phone. 15 missed calls from a number I recognized. Amanda’s cell. There were also 12 text messages. Call me now. Maya, what the hell? Derek said you’re the CEO of Nexra. Why didn’t you tell me mom and dad are going to freak out? This is so embarrassing. You made me look like an idiot. How could you let me talk about Derek’s job when you own the company? Everyone at dinner is going to think I’m insane. Answer your phone. I can’t believe you did this to me. Call me immediately. I set the phone down and looked out at the city. Somewhere out there, Amanda was having a meltdown. Dererick was probably reconsidering his engagement. My parents would hear about this soon if they hadn’t already, and I felt nothing, no satisfaction, no anger, just a quiet, distant sadness.
Jennifer knocked on my door.
“Your 11 a.m. is here. The Goldman Sachs team.”
“Thanks. I’ll be right there.”
I stood up, straightened my jacket, and prepared for the next meeting. There was work to do, an IPO to plan, a company to build, hundreds of employees counting on us to make the right decisions. My phone buzzed again, Amanda calling for the 16th time. I turned it off and went to meet with Goldman Sachs.
The rest of Monday was a blur of meetings. Goldman’s team was eager, almost pushy about accelerating our IPO timeline. They saw a window in the market. Tech stocks were hot, AI was the next big thing, and our numbers were exceptional.
“Q2 is aggressive but achievable,” their lead banker said. “Your story is compelling. Female founder, MIT background, built this from nothing. Investors will eat it up.”
“I don’t want to sell a story,” I replied. “I want to sell a sustainable business.”
“It’s the same thing in the market’s eyes.”
We debated valuations, timing, risk factors. By the time they left at 400 p.m., I had a headache forming behind my eyes.
Jennifer appeared in my doorway.
“You have 17 calls from your sister, and your mother called the main line three times. She said, and I quote, tell Maya that family is more important than some meeting.”
I rubbed my temples.
“What did you tell her?”
“That you were in meetings with Goldman Sachs regarding our IPO and would call her when available.”
“And her response?”
“She asked what an IPO was. I explained. Then she got quiet and hung up.”
I almost smiled.
“Thanks, Jennifer. Also, Derek Chin requested a meeting with you. He seemed distressed.”
“Tomorrow, put him down for 2 p.m.”
That evening, I drove to my apartment in Pacific Heights, a two-bedroom place I’d bought 3 years ago when the company’s series C had closed. It was nice, but not ostentatious. The kind of place a successful professional might own. Not a CEO about to take a company public. I poured a glass of wine and finally turned on my phone. 43 missed calls. 37 text messages. Six voicemails.
I started with the voicemails. The first was Amanda, her voice high and strained. Via, what the actual hell? Derek came home and said, “You’re the co of his company. How is that even possible? Call me back right now.” The second was my mother. Maya, Amanda just told us you run some computer company. Is this true? Why wouldn’t you tell us? Your father wants to know if this is some kind of joke. The third was Amanda again, crying. You let me introduce you as between jobs. You let Derek talk about his important job. Everyone thinks I’m a complete idiot. How could you do this to me? The fourth was my father. Maya, your mother and I are very confused. Amanda says you’re quite successful, but we don’t understand why you’ve been lying to us. Please call us and explain what’s going on. The fifth was Derek, his voice carefully controlled. Miss Chin, this is Derek. I wanted to apologize for for anything inappropriate I may have said at dinner Friday. I had no idea about your relationship to Amanda or your position at the company. I hope this won’t affect my employment. Please call me. The sixth was Amanda again, angry now. You know what? This is typical. Everything always has to be about you. You couldn’t just let me have this one thing. You had to be the CEO of Derek’s company. You’re so selfish, Maya. Don’t bother calling me back.
I deleted all six and scrolled through the texts. They followed the same pattern. Shock, embarrassment, anger, confusion. My mother, why didn’t you tell us you were successful? Were your parents? My father, I don’t understand why you would hide this. We thought you were struggling. Amanda, everyone from dinner knows now. Dererick’s boss called him. They’re all talking about it. This is the most humiliating thing that’s ever happened to me. And then buried among the angry messages, one from Amanda sent at 9:47 p.m. Derek’s boss wants to meet me. He said he didn’t know the SEO was my sister. He called me Chin like I’m important because of you. This is so backwards. I’m supposed to be the successful one.
There was the heart of it. I was supposed to be the failure. That was the role I’d been assigned in our family’s story. Amanda was the successful older sister with the prestigious job and the impressive boyfriend. I was the little sister who couldn’t get her life together. Except none of it was true. And now the story had collapsed and everyone was scrambling to write a new one.
I didn’t call anyone back. Not that night. Instead, I opened my laptop and reviewed the deck for tomorrow’s executive team meeting. We had deadlines to hit, features to ship, clients to serve. The drama of my personal life was exactly that, personal. It had no place in the boardroom.
Tuesday morning, I arrived at the office at 7:00 a.m. The executive team meeting was at 8:30, followed by Derek’s one-on-one at 2 p.m. The executive meeting went smoothly. We discussed hiring targets, budget allocations, and the upcoming all hands where we’d announced the IPO timeline. Dererick was professional, participated appropriately, and avoided making eye contact with me. Afterward, Marcus pulled me aside.
“Dererick’s freaking out. He thinks you’re going to fire him.”
“Why would I fire him? His numbers are good.”
“Because he’s dating your sister and apparently said some dumb things at a dinner party.”
“That’s not a fireable offense.”
“You should probably tell him that before he has a breakdown in the bathroom. Third time this morning.”
I sighed.
“I’ll talk to him at 2.”
Derek arrived for his one-on-one exactly on time, looking like he hadn’t slept. He sat across from my desk, hands clasped tightly in his lap.
“Thank you for seeing me, Miss Chin.”
“Maya is fine when it’s just us. And you’re not fired if that’s what you’re worried about.”
His shoulders sagged with relief.
“I… thank you.”
“I was concerned that the situation with Amanda might—”
“Your relationship with my sister is your business. Your performance here is what I care about, and your performance has been excellent. The new AI model is ahead of schedule and under budget. You’re doing exactly what we hired you to do.”
“I appreciate that, but I feel I should apologize for Friday night. The things I said about startups, about competition.”
“You didn’t know who I was. And honestly, you weren’t wrong. Most startups do fail. We just happened not to.”
He relaxed slightly.
“Amanda is very upset. She feels embarrassed.”
“I understand.”
“She wants to know why you never told her or your parents.”
He paused.
“If I’m being honest, I’d like to know, too. This is a billiondoll company. You’re about to go public. How does your family not know?”
I considered how much to share. Dererick was my employee, but he was also dating my sister. Whatever I said would likely get back to her.
“They never asked,” I said finally. “I tried to tell them in the beginning, but my father would change the subject. My mother would offer career advice. Amanda decided I was a failure and nothing I said could change her mind. After a while, I stopped trying.”
“But surely when the company got bigger—”
“Derek, what does Amanda tell you about me?”
He shifted uncomfortably.
“That you’re figuring things out, that you’ve had some career struggles, that she worries about you, and—”
“In 3 months of dating her, did you ever ask my name?”
You went pale though I didn’t.
“Did you ask what company I worked for? What I studied in school? Anything specific about my life?”
“She said you didn’t like to talk about it.”
“She said that because she doesn’t want to hear the answer, because if she knew the truth, she’d have to rewrite the story she’s been telling herself for 10 years, and that story is important to her.”
Dererick was quiet for a long moment.
“She called me this morning. She’s angry that I brought you into her workplace. She doesn’t understand why I didn’t tell her you were my souk.”
“What did you say?”
“That I didn’t know. That you were just Maya to me. Another person in the building.”
He rubbed his face.
“She accused me of choosing you over her.”
“And what did you say to that?”
“That she was being irrational. That you’re my boss and I’m grateful to have this job. That her feelings about you don’t change my professional obligations.”
He met my eyes.
“She didn’t like that answer. She wants me to quit.”
The words hung in the air between us.
“And are you going to?” I asked.
“No,” he said firmly. “This is the best opportunity of my career. I left IBM specifically for this role.”
And he hesitated.
“I’m starting to see some things about Amanda that concern me.”
I said nothing, just waited.
“She’s very focused on status, on appearances, on being better than other people.”
He shook his head.
“I thought it was just ambition, but after this weekend, I don’t know. The way she talks about you, the way she’s more upset about being embarrassed than about having completely misunderstood her sister’s life. It’s not not what you signed up for.”
“Yeah.”
I stood and walked to the window. 14 floors below, people moved through their lives, walking to meetings, grabbing coffee, checking their phones. Ordinary people doing ordinary things.
“My advice as your co, don’t make career decisions based on personal relationships. This job is good for you. Stay.”
“And your advice as Amanda’s sister?”
“I’m probably not the right person to ask.”
I turned back to him.
“But for what it’s worth, my sister is terrified of being ordinary. She spent her whole life trying to prove she’s special, important, better than everyone else. That’s why she needs you to be impressive. That’s why she needs me to be a failure. It’s all part of the story that makes her the hero.”
Dererick nodded slowly.
“What happens now?”
“You keep doing your job. I keep doing mine. Amanda decides whether she can handle the cognitive dissonance of having a successful little sister.”
I returned to my desk.
“Is there anything else workrelated we need to discuss?”
“No. Thank you, Maya.”
After he left, I finally called my mother. She answered on the first ring.
“Why?”
“Hi, Mom.”
“You have some explaining to do, young lady.”
I almost laughed at being called young lady when I was 30 years old and about to take a company public.
“What would you like to know?”
“For starters, why your father and I had to learn from Amanda that you’re apparently some kind of executive running a billion dollar company.”
“I’m the CEO and founder. We’re valued at approximately $2.2 billion pending our IPO.”
Silence then.
“Your father wants to talk to you. Hold on.”
Muffled sounds of the phone being passed.
“Ya, this is your father.”
“Hi, Dad.”
“Your mother and I are very confused. We thought you were working on a small startup, some kind of computer project.”
“It was a small startup 7 years ago. We grew.”
“Why didn’t you tell us?”
“I tried. You asked me once what I did and I said I founded an AI company. You said that’s nice and asked if I’d seen your golf clubs.”
“I don’t remember that.”
“I do. It was at Christmas 4 years ago. I tried to explain that we just closed a $50 million funding round. You interrupted to tell me about Amanda’s promotion at work.”
Another silence.
“Maya, were your parents? We should have known.”
“Should you have? When was the last time you asked me a specific question about my work, my life? Anything beyond how are you?”
“We ask about you all the time.”
“You ask Amanda about me. You ask if I’ve gotten my life together. You ask when I’ll find a real job, but you’ve never actually asked me what I do.”
I heard my mother’s voice in the background.
“Let me talk to her.”
The phone exchanged hands again.
“Maya, we’re trying to understand. Why would you hide something like this?”
“I didn’t hide it, Mom. I just stopped trying to force you to see it. You decided who I was 10 years ago, and nothing I said would change your mind.”
“That’s not fair.”
“Isn’t it? When was the last time you introduced me to someone without apologizing for me first? Without saying I’m still figuring things out or going through a phase.”
“We were trying to be supportive.”
“Were you, or were you trying to maintain the story where Amanda is the successful one and I’m the struggling one? Has that story made sense to you? It was comfortable.”
My mother’s voice went cold.
“You’re being very cruel right now.”
“I’m being honest. There’s a difference.”
“Amanda is devastated. She says you humiliated her in front of Dererick’s colleagues.”
“I sat at a dinner and listened to Derek talk about his job at a company I founded while Amanda introduced me as between jobs. How exactly did I humiliate her?”
“You should have told her who you were.”
“She never asked. In 30 years, Mom, she has never once asked me a single genuine question about my life. She decided I was a failure and she needed me to stay that way so she could feel superior.”
“That’s a horrible thing to say about your sister.”
“It’s the truth, and you enabled it. Both of you did.”
“You praised her for getting a middle management job at a regional bank while I was raising $100 million in venture capital. You bragged about her $80,000 salary while I was turning down acquisition offers for $400 million. You believed her story because it was easier than seeing me.”
I heard my father’s voice again, muffled.
“What’s she saying?”
“She’s saying we failed her,” my mother said, and her voice cracked. “That we didn’t see who she really was.”
“Because you didn’t want to,” I said softly. “It was easier to have one successful daughter and one struggling daughter. It was a simpler story.”
“Why?”
My mother was crying now.
“We didn’t mean. We thought—”
“I know, but intention doesn’t erase impact.”
“What do we do now?”
“I don’t know, Mom. That’s up to you.”
I ended the call and sat in the silence of my office. Through the glass walls, I could see my team working. Engineers debugging code. Product managers in intense discussions. Salespeople on calls with clients. These people knew who I was. They saw me clearly. My family never had.
Jennifer knocked.
“Your 3 p.m. is here. The TechCrunch interview about the IPO announcement.”
“Give me 5 minutes.”
I pulled up my email and found a draft I’d been working on for weeks, a message to our entire company about the IPO, about what we’d built together, about the journey ahead. I added a new paragraph. Many of you know that I’m a private person. I don’t do much press. I don’t share details of my life outside these walls. That’s because this company is built on substance, not stories. On results, not reputation. On the work we do together, not on who we are individually. But I want you to know this. Every single person in this company matters. Not because of your title or your salary or how impressive you sound at a dinner party, but because of the work you do, the problems you solve, the value you create. Never let anyone make you feel small for choosing substance over story. I sent it to all 847 employees.
Then I straightened my jacket, checked my reflection in the window, and went to talk to TechCrunch about taking a 2.2 billion company public.
The interview lasted an hour. The reporter was sharp, asking about our competitive advantages, our path to profitability, our vision for the future of enterprise AI. She asked if it was hard being a female CEO in a male-dominated industry. It’s hard being any. So, I said, “The gender part is just one more variable to manage.”
“Do you have advice for women in tech who face skepticism or dismissal?”
I thought about Amanda, about my parents, about every dinner party where I’d been introduced as the disappointment.
“Keep building,” I said. “Let your work speak louder than anyone’s doubts. And remember that their inability to see you is their limitation, not yours.”
The article went live Wednesday morning. By noon, it had 50,000 shares. My phone, which I’d kept off since Tuesday, showed 127 missed calls when I finally turned it on Wednesday evening. Most were from numbers I didn’t recognize, journalists probably or recruiters or people who’d suddenly discovered we were connected on LinkedIn, but 15 were from Amanda.
I listened to the most recent voicemail. Her voice was different now. Smaller. Why I read the TechCrunch article. I saw the photos of you in the office. I didn’t know. I mean, I knew you were smart, but I didn’t understand. A long pause. Dererick broke up with me. He said, “I don’t actually see people. I just see status symbols.” He said, “I treated you like a status symbol, too. A negative one, but still.” She laughed, but it sounded broken. I don’t know what to do with that with any of this. Another pause. Mom and dad are freaking out. They keep asking how they didn’t know. And I realized I didn’t know either as I never asked. I never wanted to know. Her voice dropped to a whisper. I’m sorry, Maya. I don’t know if that means anything to you, but I’m sorry.
I saved the voicemail, but didn’t call her back. Not yet.
Thursday, we held the all hands meeting to announce the IPO. 847 employees packed into our largest conference room and the overflow spaces. I stood on the small stage and told them what we’d built together. 7 years ago, we were three people in a garage. Today, we’re going public. But the number doesn’t matter. Not the valuation, not the stock price, not any of it. What matters is that we built something real, something that solves actual problems for actual people, and we did it together. The applause was deafening.
Afterward, Dererick approached me.
“That was a good speech.”
“Thanks.”
“How are you doing?”
“Better. I talked to my therapist about the Amanda situation. Apparently, I have some patterns to work on.”
He smiled. Riley, but I’m grateful for this job, for the clarity it’s given me about what matters.
“I’m glad you’re staying.”
“Me, too.”
Friday afternoon, I finally called Amanda.
“Hia,” she said, and I could hear she’d been crying.
“I got your voicemail. All 15 of them. Just the last one.”
Silence. Then,
“I’ve been thinking a lot this week about what kind of sister I’ve been, what kind of person.”
Her voice wavered.
“Dererick was right. I don’t see people. I seek categories. Status, where people fit in the hierarchy I’ve built in my head.”
“I know.”
“You were supposed to be the struggling one. The one who made me look good by comparison. And when that turned out to be completely false, I didn’t know how to handle it.”
“Amanda, let me finish. Please.”
She took a shaky breath.
“I’ve spent this whole week being angry at you, for embarrassing me, for not telling me, for letting me look like an idiot. But the truth is, I’m the one who made myself look like an idiot by never caring enough to actually know you.”
I walked to my office window looking out at the city lights.
“I read every article about you I could find,” Amanda continued. “Forbes, TechCrunch, the Wall Street Journal profile from last year. And I kept thinking, this is my sister, my little sister, and I don’t know her at all.”
“No,” I said quietly. “You don’t.”
“Can I?” Her voice was so small. “Can I get to know you? The real you.”
“I don’t know, Amanda. Can you handle it if the real me doesn’t fit into your hierarchy? If I don’t make you look good by comparison?”
“That’s fair. That’s more than fair.”
She laughed sadly.
“God, I’m such a mess. Dererick’s gone. Mom and dad are having some kind of crisis about their parenting. And I’m realizing that I built my entire identity around being better than you. And now that’s gone. And I don’t know who I am.”
“Maybe that’s a good thing.”
“Maybe the truth is I’m proud of you. I should have said that first. I’m proud of you and impressed and kind of in awe. You built something incredible and you did it while we all dismissed you. That takes… I can’t even imagine how strong you had to be.”
Tears stung my eyes.
“Thank you.”
“Will you have coffee with me sometime? When you’re not busy taking over the world.”
“I’d like that.”
“Really?”
“Really. But Amanda, if we do this, if we try to build an actual relationship, it has to be real. No performances, no status games, just two sisters trying to actually know each other.”
“I can try. I want to try.”
“Then let’s try.”
We set a date for the following Tuesday. After I hung up, I sat in the growing darkness of my office and let myself cry, for the years of being invisible, for the sister I’d never really had, for the possibility that maybe finally we could start again.
Monday morning, the IPO paperwork was filed. By Wednesday, we’d set a date, June 15th. By Friday, Goldman Sachs was projecting we’d open at $2.4 billion. None of it felt as important as the coffee I had with Amanda on Tuesday.
We met at a small place in North Beach, far from both our offices. She was already there when I arrived, looking nervous and tired and more real than I’d ever seen her.
“Hi,” she said.
“Hi.”
We ordered coffee. For a moment, we just sat there, two strangers who happened to share DNA and a childhood.
“I don’t know where to start,” Amanda said finally. “Tell me about your job. Your actual job, not the impressive sounding version. What do you do every day?”
He blinked, surprised.
“I manage a team of five people in commercial lending. We process loan applications for small businesses. Honestly, it’s kind of boring, but I’m good at it.”
“That sounds valuable. Small businesses need financing.”
“It is valuable, but it’s not… I’m not a VP. I’m not changing the world. I’m just doing a job.”
“Most people are just doing a job. There’s no shame in that.”
“I know. But I spent so long pretending it was more than it was. Pretending I was more than I was.”
She met my eyes.
“Because I was scared that if I wasn’t more, I was nothing.”
“You’re not nothing, Amanda. You never were.”
“Then why did I need you to be less? Why did I need you to fail?”
“Because you learned that love is conditional. That our parents approval depends on achievement, that you have to earn your place in the family hierarchy.”
I stirred my coffee.
“We both learned that. I just responded differently.”
“How? How did you keep building when everyone around you said you’d fail?”
“I found people who saw me. My co-founders, our early investors, the team we built, they saw me clearly, so it mattered less that you didn’t.”
Amanda’s eyes filled with tears.
“I want to see you clearly. I want to be someone who sees people clearly.”
“Then start by seeing yourself clearly, not the version you think you should be, the actual person you are.”
We talked for two hours about her real job and my real job, about her breakup with Derek and what she’d learned from it, about our parents and the ways they’d failed us both, about the possibility of something different. As we were leaving, Amanda hugged me. Really hugged me, not the air kiss performance from before.
“Thank you,” she whispered. “For giving me a chance. Thank you for asking for one.”
June 15th arrived warm and clear. I stood on the floor of the NASDAQ exchange with my co-founders Marcus and Jennifer, watching our stock price climb. We opened at $54 per share, valuing the company at $2.6 billion. My parents were there looking proud and confused and desperately trying to understand the daughter they’d never really known. Amanda was there too, standing off to the side, clapping when the bell rang, taking photos for her Instagram with the caption, My sister is a badass. No qualifications, no explanations, just truth.
After the ceremony, as we celebrated with champagne and congratulations, Amanda pulled me aside.
“I know this is your day, your moment, but I wanted to tell you I started therapy to work on the status thing, the comparison thing, all of it.”
“I’m proud of you for that and I’m proud of you for this,” she gestured at the celebration around us, “for all of this, for building something real while I was busy building something fake.”
“Your life isn’t fake, Amanda. It’s just been hiding behind a story.”
“Well, I’m done with that story. I want a real one.”
He smiled and it was genuine.
“Starting with having a sister who actually knows me and who I actually know. I’d like that.”
We stood together and watched the stock ticker. Two sisters finally seeing each other clearly.
The company continued to grow. We expanded into Europe, acquired those two startups, launched three new products. By the end of the year, we employed over a thousand people. But the thing I was most proud of wasn’t the stock price or the revenue or the awards. It was the coffee dates with Amanda every Tuesday. The phone calls with my parents where they asked real questions and listened to real answers, the slow, difficult work of building actual relationships instead of performed ones.
Dererick stayed at the company and ended up being one of our best executives. He started dating someone from our legal team, someone who saw him clearly and liked what she saw. Me. I kept building, kept leading, kept choosing substance over story. Because at the end of the day, that’s all any of us can do. Build something real, see people clearly, let ourselves be seen. The rest is just noise.
