A Rookie Entrepreneur’s Biggest F*ck-up Moment

Lounge area in Google Singapore, where the leadership retreat was held [Summer 2017]

“Tell us the story of your biggest f*ck up moment,” said the Google facilitator to a group of 20 tech entrepreneurs. They flew in from startup communities around the world to Google’s Launchpad leadership retreat.

When it was my turn to tell my story, my throat turned into a knot and tears filled my eyes with a swell of regret. I began to speak.


I’ll tell you this much. Amos was a genius.

Literally. He had the IQ of 190. To put it in context, Bill Gates’s IQ is 160. Amos pictured 3D objects in his head, and made them on rapid prototyping machines in his basement.

As far as I could tell, Amos never miscalculated anything.

Amos drank diet cokes like water. At least two 1-liter bottles a day. He drove like a mad man. He enjoyed mountain biking, but to his dismay, his girlfriend wasn’t into it.

I met Amos at Johns Hopkins University, where we shared countless meals and worked many late nights together. Eventually, we co-founded a little company to build wireless networking products.

A Do or Die Milestone

Each of our products comprised of a circuit board and about 200 electrical parts. Amos would soldered parts onto a board and never make a mistake. Amos’s devices were perfect on the first try.

In comparison, when I assembled a device, I’d make so many mistakes that it wouldn’t even turn on. I’d spent hours debugging my board.

Our first customer was the Washington Hospital Center. The director of the center stuck his head out for us and got our product approved by the hospital. This was no small feat, as getting approval for wireless equipment upgrades at a hospital is tougher than dragging a 747 through mud. We were scheduled to install our products at the center on January 1.

Little did I know, the month leading up to January 1 would be the most grueling time of my career.

A Horrible Call

About a month before, our progress hinged on Amos getting our products assembled in time. Amos locked himself in his basement to assemble the final boards.

A few days went by. We didn’t hear from Amos. Then I got a phone call.

The person on the phone was a teammate of mine. He said:

“Amos is dead.”

A moment of pause. Then my teammate continued.

“The hardware boards are in his basement. We’ve got to get the boards out of his basement.”

I let out an epic wagnerian cry of broken senseless sense of human loss and suffering, to put it lightly. Whyyyyy!

What do you mean Amos is dead! Amos is like family! We know his family! We’re raising a baby startup together! We’re on a mission to upgrade wireless infrastructure for hospitals. We were going to save lives!

Then, my rational side took over. I spoke in a cool, calm voice. “I will get those devices out of his basement. We have an installation on January 1st.”

A Tunnel-vision Desire

Over the next few days, I tried getting ahold of Amos’s mom. I couldn’t reach her, so I left her voicemails. I’d say, in a squeaky voice, something like:

“Anna, I am so sorry about Amos. But can I get my equipment from his basement?”

We didn’t tell the hospital about Amos because we didn’t want them to call off the installation. We didn’t want to ruin the mission.

We didn’t go to Amos’s funeral because we had to work.

We didn’t want to ruin the mission.

Days went by. We realized we weren’t going to get the hardware out of his basement.

We debated our options. Should we postpone the installation? We’d ruin our reputation with the hospital.

The schedules of their staff were coordinated and ready for us to do this installation. They were preparing an event at the annual American Burn Association meeting to showcase what we’re doing.

We wanted this so badly that nothing else mattered to us. I was 25 and I was ready to move mountains.

The only viable option seemed to be to rebuild the devices. We had 10 days left.

It would have taken Amos a month to build these devices, and Amos didn’t make mistakes. Now we had to what Amos did, with less time.

Over the next week, teammates and I stuffed ourselves in a lab to re-build the hardware. I don’t remember sleeping. I re-ordered the electronic parts, re-produced the circuit boards, stood by in the electronic shop as components were printed onto boards, examined each NEMA enclosure as they came off the assembly line in the custom fabrication shop.

A Miraculous Day

On installation day, my teammates and I lugged our fresh made devices to the Washington Hospital Center.

“How’re you feeling?” I asked. He replied:

“Scared shitless.”

We did the installation that day. Surprisingly, the software worked.

In the weeks that followed, we expanded installations to more departments in the hospital.

We presented at the Annual Burn Conference.

The director and those who stuck their neck out for us became our advocates.

The Biggest F*ck Up

Eventually, I had time to reflect on what happened.

My team thought of ourselves like pioneers — we were out there to enable better patient care, using technology.

Many obstacles got in my way, but I became good at overcoming them. I saw everything as a speed bump that can be overcome.

Then when Amos passed away, I let the passing of a close friend become another speed bump to me. I treated his death like just another speed pump.

But I don’t want to see everything as a speed bump.

Eventually, the startup shut down. I went on to work on more startups.

I continued struggling to build a company that cares about its people as much as its cares about their mission.

But I never again feel so consumed by the mission. Not like the way I felt in that first startup with Amos.

Maybe because a first startup is like a first love. After you’ve been hurt once, you never want love again because you don’t want to get hurt again.

Or maybe because I became aware of the importance of finding balance between having a passion and not letting my passion consume me.

Thank you for listening folks.


“Thank you for sharing Tia. Did you talk to his mom again?” someone in our group asked.

“For years, I felt guilty about the voicemail I left her. Eventually I reached out to tell her how I felt about Amos and how much I missed him. I slowly forgave myself.”

“How long ago was this?”

“Almost a decade ago.” I said, clumsily.

“Do you have a bigger, more recent, f*uck up story?”

“Not really.”

“Maybe you’re not making enough mistakes.”

The group nods in unison.

“I’ll work on that,” I said.

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