Gen Z is not the only one wearing uniforms. The 450 million-dollar AI startup boss says he lives in a hoodie and jeans “technical uniform”

luckThe series, The Good Life, shows how promising leaders spend their time and money outside of work.

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Today we meet David Shim, co-founder and CEO of the software company. Read AI.

If your personal assistant is eager to take over nasty email writing and notes during work hours, AI may have some fixes for you.

The $450 million AI assistant company from Seattle is not Sim’s first rodeo. The 45-year-old serial entrepreneur has spent most of his 25 years building and scaling companies. When he was a student at Washington University, he developed a consumer shopping portal for the name. ecobay.comIt was acquired by eBay just four months later. He then made a brief foray into hedge funds and founded Leaguetraders Inc. After working for four years in operational and marketing services roles across analytics companies such as Webtrends and Quantcast, he abandoned his 9-for-5 life and became his boss again.

Read AI has raised over $82 million, with the latest $50 million Series B funding round Business review $450 million.

Sim’s idea for reading AI was inspired by a common annoyance in one of his executive roles. gen x The entrepreneur was CEO of Foursquare from 2019 to 2020. After his advertising intelligence company was acquired by Foursquare from Snapchat Inc. As a leader in conducting many meetings, he noticed “ghosts” in the online room. To save people’s time and energy, David created “Intelligent Ghost:”.

Read AI After that, he raised over $82 million from the backer, and in the latest $50 million Series B funding round Business review $450 million. In 2024, we surpassed 1 million monthly users. Just recently, the company introduced sales AGI. Here, users can “sell” the “atmosphere” by relying on AI tools to advance their transactions.

The Seattle-based entrepreneur enjoys many victories in expanding successful businesses, but he has a desire for life beyond the attractive numbers of his bank account. Sim is a self-proclaimed diet coke “lovers” and an avid powerlifter who has learned important business lessons since childhood. Nintendo game. He is a big advocate for the simple “technical uniforms” of hoodies and jeans. And sometimes he’s scattered around the trip. Patagonia And Singapore.

“Money is just a number to track (OF), but making time for the experience and the joy their experience offers is something you remember,” Sim says luck.

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Finance

luck: What is the best investment you’ve ever bought?

I invested in my last startup, which was placed in every round until I got over $200 million in Snapchat in 2017. I postponed my salary for almost three years and placed it for each round after that. On our salary, I think I was employee #5, even if I was the founder.

Recently, I invested in a company called Dave through a special purpose vehicle (SPV) through a friend and former colleague Imran Khan. SPV invested in $6 in 2023, with the stocks trading at $200 per share recently.

And the worst?

In my 20s, I thought margins were an accelerator, but that was until I was all in on a single stock with margins for a while. It turns out that the spread from the acquisition price of School Specialty Inc. was very widespread and free money. It’s not free money, and when the merger was cancelled, I got on the line of losing everything. I’m pleased that this was an early stage in my career and net worth. This was a great lesson for all future investments.

Editor’s note: Buying at margins is a type of investment with borrowed money, amplifying returns as well as losses. Education-Supplies Company School Specialty was the acquisition target in 2005 before Bain Capital and Thomas H. Lee ceased the $1.5 billion deal, citing “structural and market-related challenges.”

If you have children, what does your childcare arrangement look like?

It’s my baby who reads AI, my current startup. It’s always the same as me and always in my heart.

“I wear a standard technical uniform: hoodies, black shirts, jeans, sneakers. Each variation is sufficient, and one of the first decisions of the day is the easiest.”

How about your life arrangements: Are there any fashionable apartments in the city or the vast suburbs?

I live in Seattle’s South Lake Union area and ride a lime scooter for just 10 minutes from my downtown Reading AI office. If you come to my apartment, you will find a minimalist one bedroom. When you are the founder of a startup, you live and breathe the work, and everything else is secondary, including the furniture in your apartment.

Do you have a wallet?

Yes, and now it has $220 in cash and three credit cards. American Express Platinum is my go-to card for large purchases, but my Bank of America The reward is for cashback. We try to move away from point optimization to keep cashback simple.

What personal financial advice would you give to your 20-year-old self?

Invest in two things. S&P 500. Investing in individual stocks is not a way to build wealth. Spend time researching your inventory, investing in yourself and building your skill set. This does not mean you’re leaving the market. Rather, they stick to indexes like the S&P 500. There, they always outperform individual stock traders. The amount of time and risk associated with selecting individual stocks did not justify a slightly better return.

What subscriptions can’t live without?

Reme pass. (A company that uses electric bikes, scooters and mopeds.) Last year, I was informed by Lime that I was in the top 1% of riders in the world (673 miles in the past two years). You can leave the apartment at 8:50am and after 10 minutes you can go for a video conference with the cold brewery. That’s another of my time hacking.

Where does your watch come from?

I’m a minimalist so I don’t have a wristwatch. The last watch I still own is the TAG Heuer my dad gave me to graduate from high school. It reminds me, I haven’t worn it in 10 years so I should probably sort it out.

Essentials

How do you get daily coffee fixes?

That’s Starbucks Cold brew, light ice, regular ice means half of coffee. Order a cold brew just before unlocking the lime scooter.

After a cold brewing, I am a diet cola enthusiast. This is only natural after drinking at least four times a day for the past 20 years. I had dinner with the Pepsi executive team at Cannes a few years ago, and my loyalty to Diet Coke was asked by the waiter. We didn’t win that business that day.

How about eating on the go?

Read AI uses a service called Peach. This will email you with morning options about what to eat for breakfast lunch and offer your choice to the office by noon. This brings efficiency not only to me, but to the entire Read AI team.

Where do you buy groceries?

Amazon It’s fresh and I’m the best. It knows what I like, makes that list easy to access and delivers correctly to my door.

How often do you eat in a week, compared to cooking at home?

Doordash And Ubereats fights regularly for my attention. Dinner is chosen based on what I can order online and based on routes to and from work.

Where do you shop in your work wardrobe?

It’s either online or when I’m dressed. When it comes to holidays and birthdays, it may be difficult to buy for me, but my friends and family can safely assume that they can use another shirt, jeans or jacket.

What is your typical work outfit?

I wear standard technical uniforms: hoodies, black shirts, jeans, sneakers. There are plenty of variations for each, so one of the first decisions of the day is the easiest.

Are you a proud owner of futuristic gadgets?

Read AI. It gives me about 10 hours a week. AI can make your life simpler by attending meetings on your behalf, giving birth to deliverables and helping you discover opportunities that you may have missed. This ability to build digital twins to increase productivity gave us the ability to scale in ways that are impossible a few years ago.

Treat run

How do you get from the top job?

I like to lift heavy things. Last year I set my goal to reach a £1,000 club. This means you need to lift a total of 1,000 pounds across bench presses, deadlifts and squats. Now I’m at a 940 pound club with the goal of lifting another 60 pounds by the end of the year.

What is the best bonus street you bought yourself?

When I grew up, I played a game called Jingis Khan at Nintendo. It was a turn-based strategy game, and I ended up playing the entire weekend as a 10-year-old. I think this experience has shaped the way I think about life and business.

When placed on Snapchat in 2017, he bought (i) a sealed version of the original rated video game, and (ii) a gold coin from that era of the Mongol Empire when Jinghis Khan reigned.

How do you treat yourself when you receive a promotion?

I get a lot of joy from giving to others. This is not a charity, it’s something I still do, rather it’s about giving to friends and family. My dad always wanted to go to Patagonia with his siblings, but in 2023 I was in a position to make it happen. Money is just a number to track (OF), but creating time for experiences and the joys that those experiences offer is something you remember.

How many days does the annual holiday take?

I take at least two weeks off a year, with my mother, father, siblings, his family, and another week with friends. His family is more Kabo, and his friends are Ibiza and Samui.

Fortune wants to hear from their leaders about what their “good life” looks like. Please contact us: emma.burleigh@fortune.com.