Venture Evolved
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Venture Evolved

Revenge of the Nerd

This story is about a good friend of mine who wished to remain anonymous given the content of the story. We wrote this story together. Enjoy.

Photo by Jefferson Santos on Unsplash

It was an unusually crummy weather day in 2005, and my wife and I decided to go to a movie.

As we were exiting our parked car to go into the theater, my wife inquired if she had to bring along her big purse. I’m always amazed on the occasions that I have to lift it. It is so heavy, I once checked if it contained a boulder collection or several preschool children.

“Naaaah, leave the purse, I said. My thinking: this was a pretty safe part of the city, and she didn’t need her purse in the theater and who wants to schlep a heavy purse for no reason?

The movie turned out to be awful, and we talked about the chain of bad decisions that resulted in the production of this opposite-of-a-masterpiece. Little did we know that this conversation would be a foreshadow.

We casually returned to our car following the movie. What’s an orange cone doing near our car? And why is the rear window broken? That’s odd. The steroid-fueled MLB home run race was back in 1998, and we weren’t anywhere near an MLB stadium. Little glass cubes were everywhere as if the Antwerp Diamond Exchange had relocated to this nondescript parking lot to save on rent.

“My purse is gone!” my wife shouted. We left her purse in the car. I shouldn’t have told her to leave it. That was a really stupid mistake.

This is going to take a ton of time to fix. I have to cancel all our credit cards and my wife will have to get a new license. I don’t have time for this. This is stressing me out. And we have to fix the car and I can’t be without it for more than a day. At least it won’t cost that much to get back to normal.

“Oh my god, they have my license, our address, and our keys!” uh oh. Cancelling credit cards is going to be the easy part.

We sprung into action, calling our neighbors. We explained the situation, and begged them to enter our apartment and get our dog. They retrieved the dog, and while we were on the phone, gave us the play-by-play walking through the apartment. They reported everything was absolutely in order. What a RELIEF. It was still going to take a lot to unwind this mistake but at least the damage and violation of our privacy was contained. It’s a big mistake, not a catastrophic one. We dodged a bullet.

We next strolled to the police department to report the broken window and stolen purse. As we swam through the viscous police bureaucracy, it became clear that in our big city, this was a banal crime deserving of approximately zero police resources. And that’s zero rounded up. We drove home with our newly remodeled rear window/air conditioning system, looking forward to putting this incident behind us.

We pushed open our door, and the familiar and precise squeak from the door hinge greeted us. You might think that persistent squeak would annoy us, but it’s a reminder that we are home; it’s an invitation to relax. But not this time. As we walked through our apartment, something seemed “off.” Our neighbors came down with our dog and they said this was the state of the apartment when they fetched him.

Clothes were sticking out of our drawers. Items strewn about on tables and desks. We were slightly concerned that our neighbors had thought that clothes hanging out of the drawers was “normal,” but that’s another story. I am kind of offended. I wonder what state their apartment is in.

Then my wife yelled, “my jewelry’s gone!” At the same moment, I noticed my laptop was gone.

“OUR DOG MET THE ROBBER!” I shouted. I am not sure why that preceded my other ingenious insight: “WE’VE BEEN ROBBED!”

It took awhile to contain our emotions and the feeling of violation. When we recombobulated ourselves, we called the police department to file another report. This time we got a little more attention. They arrived and took fingerprints of both our apartment and the car. The officer said, “We never find any prints,” and sure enough they did not. Are all the CSI shows entirely manufactured bullshit? It was late now, there was nothing to go on, and it was time to go to bed. Because of my stupid mistake, we had just been violated, we lost a lot of valuable things — both financially valuable and emotionally so. We probably would never recover them, but at this point it was more about calming ourselves down so our emotions did not spiral out of control.

My car’s window was still broken and the thief still had my car keys. To be safe(r), I parked it in an underground lot not associated with my apartment. In driving to that lot, I happened to be looking up at the sky and saw a shooting star. I’ve seen hundreds of these while up in the mountains, but this is extremely rare to see one from within a city. Today truly was unique. One decision.

I couldn’t really sleep well that night. I opened my eyes at 4 am with an epiphany: I had remote access software installed on my computer, and I could access that software’s site to see if my laptop has been “online” after the theft. That is, of course, if the robber(s) hadn’t wiped the drive clean.

But dumb enough to steal from me also meant dumb enough to not reformat the hard drive, and indeed, the remote access software website showed that the laptop had briefly gotten online later that night after the theft. Suddenly the feelings of despair and violation turned to smoking cauldron of exhilaration, fear and vengeance. Time to NSA this bastard.

The car might not have turned up and fingerprints, but the laptop might have a lot of digital fingerprints. I started by recording the IP address and started amassing information for the police department. I also made it my mission to figure out a way to remotely control my laptop when it was online. But this was risky; if the perp was in front of the computer while I remoted in, he (I guess it could have been a she) would be notified, and that might prompt him to turn it off or reformat the thing. I had to be stealthy.

I staged a remote session with my work computer so I could see exactly what notifications where shown. I altered the configuration of the software to reduce the notifications as much as possible. I decided to set my alarm for 4 am to try to see if the thief had left my laptop online for night. Nope. It was off. I became obsessed with this detective lottery. In my more bold moments, I was even checking periodically from work, but alas my laptop was rarely online. My initial adrenaline from discovering this opportunity began to diffuse.

Meanwhile, my credit cards showed fraudulent charges at three gas stations and a McDonald’s (what can I say, the thief had good taste). I mapped out those addresses on Google maps and could see what path the thief took from the movie theater to our apartment. I contacted each place of business in order to review their security camera footage. But either they didn’t have any equipment or it was not working! Frustrating.

My hunt to find my laptop while it was still online continued. Then one Friday around lunch time — bingo — the laptop was online. My stomach dropped and my heart stopped. Now what? I hadn’t prepared for what to do next.

I logged in and had control of the laptop, but had no clue whether the thief was watching. I saw my desktop picture was different — it was a man and a couple kids at a nearby amusement park. I checked the timestamp and geolocation of the photo and low and behold it placed the thief ten miles from the movie theater the day before. It was hard to reconcile this happy family picture with the crime he would commit against me the next day. As excited as I was, I didn’t want to press my luck. It was the middle of the day, after all. I logged off, proud of the restraint I displayed as if I were a pirate having sprung open a full treasure chest- only to take the single gold goblet at the top before shutting the lid.

I resolved to try again very late that night, and indeed the laptop was still online! I moved the mouse a little and waited….I wanted to see if he would move it. Nothing. Yes, it was 4am but since he rarely left it on overnight, I thought if it was on, he probably was in front of it. So I moved it again. Nothing. Then I decided to act fast and open up the webmail he was running. I got his Yahoo email address, but he had not also included a First/Last name in the email setup. Damn. Then, as I was futzing around in his Yahoo account, he took control of his mouse. HOLY SHIT. I froze and was stunned. This was the 21st century version of victim and perpetrator finding themselves suddenly face to face. Thankfully, he must have assumed it was a computer glitch, because he didn’t log off. But I did. I was sweating.

As dawn broke, I called the police with as much information as I had captured, and they said this is good, but not enough for a warrant. They essentially said, “keep going — it’s your computer and you have every right to snoop around it.”

Within a few days, my daily 4am “checks” yielded several sessions where I was lucky to have logged in while it was left online. He didn’t seem to be in front of it. Then I really went to town. I read through and screenshotted dozens of emails. I learned the following surprising things:

  • The first/last name he used in email
  • The kind of car he drove
  • His grandmother’s occupation
  • In what part of the city he lived
  • That he also ran a “dog walking service” through Craigslist. I screen captured the Craigslist listings. He had written, “I love dogs,” and this might have been true, as our poor dog was completely safe and unaffected by the whole ordeal.
  • He was a college football fan….of the college I went to a mere 1,200 miles from where we both lived. OUCH.
  • That he had two kids with a girlfriend
  • That he was cheating on her with other women and men

I spent hours compiling all of this into detailed reports for the police department.

This was now enough for the police to subpoena the address using the IP address and other information I had collected. When I handed over the full dossier, the head of the detective unit declared, “if you ever want a job as a detective here, we will hire you on the spot.” Years later, when I applied to work at the CIA (another long story), I included these docs in my application packet.

The police got a warrant for an arrest the next day and knocked on the door at 7 am — the earliest they could serve a warrant. The thief ran through the house and tried to hide in the dryer. Needless to say, that didn’t work, and he was arrested.


  • They collected my laptop and scores of other electronics
  • His “shtick” was hanging out at movie theater parking lots and watching whether women left the car with their purses. He must have done this dozens of times
  • He pleaded guilty to a felony — breaking and entering
  • He went to prison. He’s probably out right now on good behavior and reading this on another stolen laptop
  • We have since never left any purses in any cars

I have always wondered if he figured out — perhaps while he had time to think in prison — that the strange movement of the mouse was me.



Jason is a venture capitalist, business school professor and former software engineer. Jason is a Partner at Origin Ventures and he has been in the venture business since 2001. He also teaches the venture capital and private equity lab class at Chicago Booth.

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Jason Heltzer

Dad, venture capitalist at @OriginVentures, @chicagobooth professor, Chicagoan. I was a nerd before it was cool to be a nerd.