The Google Bitch

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Grandiose-TIER Asset: The Google Bitch

Grandiose-TIER Hustle Asset

The Google Bitch: How I Faked My Way Through Chicago Politics

The Origin Story of The Executive Jokester: Part 3

Asset Class: The Intern

Rarity: Chicago Transplant

Special Ability: Hypersonic Search

Introduction: The Great Escape

If Annandale, Minnesota, was the frying pan of small-town boredom and police harassment, Chicago was the fire. And I jumped right into it.

At age 20, I needed a reset. The “Garage Days” were over. The delinquency had run its course. I needed to get out of the Wright County bubble before I became a statistic. So, I did what any rational kid from the cornfields would do: I signed up for Job Corps and requested a transfer to the south side of Chicago.

It was a culture shock that hit me like a freight train.

I went from a town where “diversity” meant someone was Lutheran instead of Catholic, to being the only white kid in the room. I lived in Southwest Chicago, surrounded by a culture I had only seen in movies. My friends were black, gay, urban, and hardened by a city that doesn’t care if you’re “Minnesota Nice.”

This wasn’t just a change of scenery; it was a demolition of my worldview. All the prejudices and small-minded thinking I had absorbed from people like my Uncle Tommy were dismantled in real-time. I learned quickly that respect isn’t given because of who you know; it’s earned by how you handle yourself when you’re the outsider.

I excelled in the Job Corps courses because, frankly, I was motivated by fear. I wanted to get home, but I wanted to go home successful. I wanted to prove I could survive in the big leagues. That motivation landed me the internship of a lifetime: Working in the office of Congressman Danny K. Davis.

Enter The Dragon: Tumia Romero

Politics is a blood sport, and Chicago politics is the UFC.

I walked into Congressman Davis’s office wearing a cheap suit that didn’t fit, carrying a briefcase that was probably empty, looking like I was ready to sell term life insurance. I thought I was going to be shaking hands and kissing babies.

Instead, I met Tumia Romero.

Tumia was the Deputy Chief of Staff. She was a force of nature. She didn’t walk; she marched. She didn’t talk; she commanded. She was one of those people who could handle three phone calls, a crisis meeting, and a lunch order simultaneously without dropping a beat.

She took one look at me—this terrified kid from Minnesota—and decided I was going to be her personal project. She didn’t assign me to file paperwork in the basement. She made me her Office Assistant.

But in my head, my job title was “The Google Bitch.”

The High-Speed Information Hustle

Tumia didn’t have time to look things up. She was too busy running the city. Her workflow was chaotic and terrifying. She would be on the phone with a high-level constituent, a lobbyist, or a rival politician, debating policy or solving a crisis.

Suddenly, she would snap her fingers at me. That was the signal.

She would cover the mouthpiece of the phone and bark a command: “Find out the unemployment statistics for the 7th District in 2018 vs 2020. Go.”

Then she would go back to talking smoothly on the phone, stalling for time.

My heart would hammer against my ribs. I had maybe 45 seconds before she needed that number. I would dive onto the computer, fingers flying across the keyboard. I became a master of “Boolean Search” before I even knew what it was. I learned to scan government PDFs, filter out the fluff, and find the exact piece of data she needed.

“Got it,” I’d whisper, sliding a sticky note onto her desk.

She would glance at it, nod, and seamlessly integrate the fact into her conversation: “Well, actually, if you look at the 2020 numbers…”

This happened 50 times a day.

  • “Who is the alderman for the 4th Ward?”
  • “What is the budget cap for the housing initiative?”
  • “Find me a restaurant near the loop that serves vegan options for a donor lunch.”

I was her external hard drive. I was her second brain.

The Lesson: Resourcefulness > Knowledge

This experience taught me the most valuable lesson of my professional life, one that I use in Real Estate every single day: You don’t need to know the answer. You just need to know how to find it faster than everyone else.

In school, they teach you to memorize facts. In the real world, memorization is useless. The world moves too fast. The laws change. The market shifts. What matters is resourcefulness.

Tumia taught me that it’s okay to say, “Let me check on that.” But you better be back with the answer in 30 seconds.

I learned to speed-read. I learned to summarize complex political jargon into three bullet points. I learned to anticipate what she was going to ask before she asked it. I wasn’t an expert in politics. I didn’t know the first thing about legislative procedure. But I became an expert in information retrieval.

The “Google Bitch” Methodology

There is an art to being a good “Google Bitch.” It requires three skills:

  1. The Filter: The internet is full of garbage. You have to ignore the noise and find the primary source immediately.
  2. The Synthesis: Tumia didn’t want a 10-page report. She wanted the “So What?” She needed the leverage. I learned to strip away the nuance and deliver the weaponized fact.
  3. The Poker Face: Sometimes, I couldn’t find the answer. I learned how to hand her a note that said “Data Unavailable, Pivot to Topic B” without looking panicked.

Returning Home

I eventually left Chicago. The pace was exhausting, and the cornfields of Minnesota were calling me back. But I returned a different person.

The “Delinquent” from Annandale was gone. In his place was a guy who had survived the South Side, navigated the halls of Congress, and served as the right-hand man to one of the toughest political operators in the city.

I brought that energy back to Minnesota. I stopped looking at problems as dead ends and started looking at them as search queries.

  • Client asks a question about zoning laws? I’m the Google Bitch. I’ll find the answer before they finish the sentence.
  • Need to know the history of a property? I’m the Google Bitch. I’ll dig up the permits from 1994.

I wear the badge proudly now. Being a “Google Bitch” isn’t demeaning; it’s a superpower. In an information economy, the person who can find the truth the fastest is the King.

Thank you, Tumia. And thank you, Google.

Get the “Chicago Intern” trading card at TheExecutiveJokester.com.

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