My Sister Called Before Dinner And Told Me Not To
My Sister Called Before Dinner And Told Me Not To Embarrass Her In Front Of Her Boyfriend’s Tech Board Friends, Because His Company Was Worth Billions And My “Startup Thing” Still Sounded Like A Garage Phase To Her. I Sat Through Wagyu, Wine, And His Speech About The Brilliant CEO Taking Nexra AI Public, While Amanda Kept Warning Me To Blend In And Stop Acting Like Entrepreneurship Was A Real Career. She Thought I Was Still The Family Disappointment In Nice Slacks. Then Monday Morning, Her Boyfriend Walked Into The Boardroom And Saw Me Sitting At The Head Of The Table.
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
Nex 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. “Derk’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. Derrick says, “Next 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 Nex’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. Why 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, Nexer 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 CEO 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 wounded 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 seven
years ago. 7 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 Derek 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
- 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 letters 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.
Coffees ready. The boards arriving at 8:45.
Full attendance confirmed. Including the new executives. 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. Dererick 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. Arcidio Marcus leaned over and whispered something to him. I couldn’t
hear it, but I could imagine that’s Ario 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.
Derrick 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 mapaps, 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? Em 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. 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. May
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.
See more on the next page
