A Short Meeting. One Question. A Response Years in the Making.

A snapshot of my Silicon Valley adventure.

Photo by Jen Theodore on Unsplash

“So what do you want to do?” asked Bill.

Bill is a General Partner at a prominent Venture Capital firm. His resume is impeccable. He has numerous exits from investments in enterprise and communications infrastructure companies.

I had met Bill before, though he doesn’t remember. It was few years back. We were pitching a different company, and I barely spoke at that meeting. I don’t blame him for not remembering.

I do recall his stoic mannerism and pierce-through-your-soul stare. He only feigned interest in what my colleague presented that day. He apologized before taking a phone call during that meeting. An unspoken way to say he wasn’t interested.

On this day, I am sitting across from him again. This time just the two of us in the room. I am not here to pitch a new startup. No power-point presentation. No laptops in the room. Just a small table between us.

Bill stares at me, waiting for a response.

The question hangs in the air. No convenient distraction to swipe it away. It echoes in my ear.

I sit there. Not prepared to respond. Yet.

I am an outsider.

I came to the US as an Asian immigrant at age 14. It took me weeks to figure out that the blond kid from Science class was only asking me for gum, not making fun of my broken English. And eventually I figured out Sloppy Joe was the name of a cafeteria food item, not the long-haired kid from PE.

When I moved from Chicago to Silicon Valley, I remained an outsider. I had swapped enough Chinese for American that English was no longer a foreign language. But I was still on the outside looking in. Looking at all the headlines about startup fame and riches. The glory of startup founders. The king-making power of venture capitalists.

I let the seduction of lets make a dent in the world-while making a killing” manifesto reel me in.

If I can just crack through this Silicon Valley maze. This fraternity. This private club. I might just find my way out of this outsider’s mask.

So my wife and I leave our families and friends in Chicago. We get off the plane at San Francisco.

I am here. An outsider. And I want to start a company.

Not What I Envisioned

“What do you do for work?” asked the ER doctor.

It was my third visit to the ER in two weeks. I tried to remember what EKG stood for.

“I am unemployed, but trying to raise venture capital to start a company,” I said.

“Well, that must be the reason then. That’s why you are having these chest pains. The readings are normal. You just have too much stress,” said the ER doctor.

He was right. I had gone over a year without a paycheck. I worked and hustled and struggled. Days and nights. Weeks and months. Now over a year. No investor said yes. My optimism and drive were now replaced by anxiety and despair.

I thought I was dying.

Perhaps this is just not meant to be. Maybe I am just not cut out for this. Fear has a way of convincing me that I am not good enough. Not good enough to be one of those successful startup founders that I read about from afar.

And want to become.

Hope Comes.

Battles with self-doubt and fear can lead one to surrender. Give up. Believe the lies. Never to fight again.

And after years of rejections, I stopped fighting.

Is this how depression feels like? It is invisible yet cuts like a knife.

In that pit of despair, God finds me.

I surrender again. Not to give up. But to give in. To Him.

Then one phone call can swing things.

“Hi Allan, this is Randy. Please give me a call.”

This is where the cliche comes in: persist long enough, and good things may just happen.

Randy is a Silicon Valley luminary. He had made nine-figures as the VP of Sales for an Internet infrastructure company whose stock was north of $1,000 a share at one point. He was later the CEO of a high-flying router startup that had attracted over $250M in venture capital.

He is now the founder and CEO of a new startup, Network Vanguard Inc. And he asked me to join his founding team.

This is a life-saver of an opportunity. Of course I accepted the invitation.

Going Along for the Ride

“Allan, don’t ask any questions. Just come to my house tomorrow morning at 7:30AM. The rest of the team will be there too,” said Randy.

I arrive at his house in Los Altos Hills the next morning. The other co-founders were already there.

“What’s going on? Why did Randy summon us here?” I asked.

Randy walks in. He says, “I got a call from (famous venture capital firm #1). They want us to pick them instead of (famous venture capital firm #2) for our Series-A round. I asked all of you to be here so we can decide as a team. If we want (famous venture capital firm #1), we need to be at their office at 9AM.”

A few hours later, I witness the famous power brokers at (famous venture capital firm #1) pitch us on why Randy should take their money.

It was glorious. I got an inside look at the private club. This secret world. How did I get here? A seat at this table?

I was now a part of a venture-funded startup company. A company backed by (famous venture capital firm #1) and (famous venture capital firm #3). The last time these two firms came together was to back (household-name company that starts with the letter G).

My outsider’s mask was starting to loosen.

But it was Randy’s company. Not mine. I was just a passenger.

Time to Move On?

“You should go talk to my buddy Bill. He is a venture capitalist and has got tons of experience. He can give you advice on how to navigate this,” said Paul.

Paul is my mentor. He is also a Silicon Valley luminary. He also enjoyed success with another company whose stock was north of $1,000 at one point. He was that company’s founding VP of Engineering.

We met when Randy recruited him to be Network Vanguard’s VP of Engineering.

But by now, Paul had already left Network Vanguard. And I was considering the same. It had been more than two years since Network Vanguard’s founding. Internal strife and conflict were threatening to bring down the company. Diverging product directions can do that to promising startups.

I needed advice. Stay at Network Vanguard? Split up the company to accommodate the fighting camps? Leave? And to do what?

“Do you think Bill will want to meet with me just for advice?” I asked Paul.

“Don’t worry. I will set it up for you,” said Paul.

Just Here for Advice

“I will be at Bill’s office at 9AM. We will have you dial into the meeting,” I said to Mitch.

Mitch came to Network Vanguard through Paul. He is the most brilliant technologist I have worked with. And he was also wrestling with the same questions I had. We both wanted to see a healthy resolution from the Network Vanguard situation.

He was based in the UK, so only I was to attend in person.

I felt anxious as I walked into Bill’s office on Sand Hill Road in Menlo Park. I didn’t know what to expect from Bill. I still had vivid memories of my first time meeting him years ago, when he ended that pitch meeting by taking a phone call.

Will it be different this time? Does he remember me? Is it better if he didn’t? Have I prepared enough for this meeting? Should I bring my laptop? What if he deems me not good enough? Is my lack of a Stanford degree OK? What if he thinks I am an imposter, an outsider?

Will he dismiss me with yet another unspoken gesture?

At least Mitch will be on the phone. And I am just here for advice.

The Answer

Hi Allan, I am Bill, he said, smiling.

That’s a good sign. Smiles are good. I focus on not pondering whether it was good that he doesn’t remember me.

“Hi Bill, great to meet you,” I said.

It’s a small conference room. Nondescript. A projector in the corner. A phone on the table. I sit down, a bit calmer now. Let’s see where this goes.

We get Mitch on the phone, and exchange pleasantries with Bill.

“Paul tells me you want advice on Network Vanguard. Tell me more,” said Bill.

I smile. Not to be friendly, but to make myself feel confident.

I spend the next five minutes setting the context. I painted a picture of how Network Vanguard got here, the issues facing the company, and the dilemmas Mitch and I felt.

Bill listens. Gaze focused on me. I meet his stare. It tells me he hears me. I continue.

“So we think there are great assets that Network Vanguard has built. We need your advice on how to best proceed, both for maximizing the value of those assets, and also for our own career paths,” I said.

Bill stares at me. Nods, but doesn’t say a word.

The silence is piercing. I wonder what it means. I await his response.

“That’s interesting,” said Bill. “Maybe there is nothing else you can do at Network Vanguard.”

Not quite what I expected.

“That might be the case, Bill. The good news is that we have learned quite a bit from our experience at Network Vanguard,” I said.

“Tell me more,” he said.

“Well, for one thing, we are seeing that demand for mobility is only going to increase. We see this trend with every customer we talk to, from Telecom Italia to T-Mobile to Sprint,” I said.

“But here is the thing. Today’s mobile networks were not designed to handle this level of explosion in demand. Things are going to break. The mobile operators are going to struggle. They need a new solution,” I continued.

“We see the need for much smaller cellular base-stations, deployed everywhere, in order to meet this explosion in demand. And when that happens, new network elements will be needed at the core networks,” I said.

All of a sudden, Bill smacks the table. I stop dead in my tracks. Startled.

He looks at me, eyes brimming.

“OK now that’s exciting. You’ve got my attention,” he says.

Quite a turn of events, I thought.

“So what do you want to do?” he asked.

My mind races. Bill’s eyes squarely on me. He wants an answer.

But it’s a question I hadn’t considered. I am just here for advice. Wasn’t he supposed to counsel me on what to do? Why is he asking me this? I am pretty sure Mitch hadn’t thought about it either. We certainly hadn’t discussed it prior. What do I say?

I need to say something. I need his stare to go away.

An answer came to mind. A very bold one. One I felt scared to say, yet yearned for deeply. I hope Mitch doesn’t disagree with me once I respond.

“We want to start our own company,” I said.

“Good!” Bill smacks the table again. “That’s what I do for a living,” he said.

I walk into the parking lot in a daze. I arrived here fifteen minutes earlier for advice. Now I walk out with a $250k seed investment commitment.

My phone rings. It’s Mitch. I am sure he is just as shocked. I need time to process what just happened.

I think I am starting a company.

As an outsider.

Some individual and company names in this story have been changed.

Founder of two Silicon Valley companies. CEO of KeyWise AI. Board Member of U of Illinois Chicago College of Engineering.