Being in the C-suite is a high-pressure job with long hours, board responsibilities, and intense scrutiny. But what is it like to be a top executive when you’re off the clock?
Fortune’s series, The Good Life, shows how up-and-coming leaders spend their time and money outside of work.
Today we meet David Shim, the cofounder and CEO of software company Read AI.
If you’re yearning for a personal assistant to take over pesky email-writing and note-taking during the workday, then Read AI just might have the fix for you.
The $450 million AI-assistant company out of Seattle isn’t Shim’s first rodeo. The 45-year-old serial entrepreneur has spent the better part of 25 years building and scaling companies; when he was a student at the University of Washington, he developed a consumer shopping portal named eccoBay.com, which was acquired by Ebay after just four months. He then went on to found LeagueTraders Inc., with a brief foray into hedge funds. After four years working in operations and marketing services roles across analytics companies like WebTrends and QuantCast, he ditched his nine-to-five life to once again be his own boss.
Read AI has raised over $82 million, with the latest $50 million Series B funding round valuing the business at $450 million.
Shim’s idea for Read AI was inspired by a common annoyance in one of his executive roles. The Gen X entrepreneur was the CEO of FourSquare from 2019 to 2020, after his ad intelligence company Placed was acquired from SnapChat Inc. by FourSquare. As a leader helming many meetings, he noticed “ghosts” in the online room—unengaged employees with their cameras turned off, often invited to a call when they didn’t need to be. To save people’s time and energy, David created “intelligent ghosts:” AI assistants that sit in on discussions, recommend changes to meetings, and send out notes before and after the calls.
Read AI has since raised over $82 million from backers, with the latest $50 million Series B funding round valuing the business at $450 million. In 2024, it surpassed one million monthly users—and just recently, the company introduced Sales AGI, where users can “vibe sell” by relying on the AI tools to help move deals forward.
While the Seattle-based entrepreneur has enjoyed many wins in scaling successful companies, he has a lust for life beyond the enticing numbers in his bank account. Shim is a self-proclaimed Diet Coke “connoisseur” and avid powerlifter in the gym, who has learned important business lessons from a childhood Nintendo game. He’s loves the gym—like Starbucks and Chipotle’s CEOs—who hopes to one day join the 1,000 pound club with lifting. And sometimes he splurges on travel—which includes covering trips for his friends and family to places like Patagonia and Singapore.
“Money is just a number to keep track [of], but creating time for experiences and the joy those experiences deliver is what you are going to remember,” Shim tells Fortune.
The finances
Fortune: What’s been the best investment you’ve ever bought?
Investing in my last startup, Placed, at every single round until we were acquired by Snapchat in 2017 for over $200 million. I deferred my salary for almost three years, rolling it each subsequent round at Placed. In our payroll, I think I was employee #5, even though I was the founder, as I didn’t directly take a paycheck.
More recently, I invested in a company called Dave via a Special Purpose Vehicle (SPV) via a friend and former colleague, Imran Khan. The SPV invested in $DAVE at $6 in 2023, and most recently, the stock is trading at $200 a share.
And the worst?
In my 20’s, I thought margin was an accelerant, and it was for a while, until I went all-in on a single stock with margin. I saw that the spread from the acquisition price for School Specialty Inc. was so wide, it was free money. It was not free money, and when the merger was cancelled, I rode the line of losing everything and more. I’m glad this was early in my career and net worth, as it was a great lesson for all my future investments.
Editor’s note: Buying on margin is a form of investing with borrowed money, which amplifies returns as well as losses. Education-supplies company School Specialty was an acquisition target in 2005 before Bain Capital and Thomas H. Lee called off the $1.5 billion deal citing “structural as well as market-related challenges.”
If you have children, what do your childcare arrangements look like?
Read AI, my current startup, is my baby. It’s always with me and always on my mind.
“I wear the standard tech uniform: hoodie, black shirt, jeans, and sneakers. With enough variation of each, one of your first decisions of the day is the easiest.”
What are your living arrangements like: Swanky apartment in the city or suburban sprawling?
I live in the South Lake Union neighborhood of Seattle, just a 10-minute Lime scooter ride from the Read AI offices in Downtown. If you came to my apartment, you’d find a minimalist one-bedroom. When you are a startup founder, you live and breathe the work, and everything else is secondary including furnishing your apartment.
Do you carry a wallet?
Yes, and right now it has $220 in cash, and three credit cards. The American Express Platinum is my go-to card for big purchases, while my Bank of America Rewards is for cash back. I try to stay away from the points optimization, as cash back keeps it simple.
What personal finance advice would you give your 20-year-old self?
Invest in two things: yourself, and the S&P 500. Investing in individual shares isn’t the way to build wealth; spend the time you’d research a stock, investing in yourself, building up your skillset. This doesn’t mean stay out of the market; rather, stick with the indexes like the S&P 500, where they’ve consistently outperformed individual stock traders. The amount of time and risk associated with picking individual stocks didn’t justify the slightly better returns.
What’s the one subscription you can’t live without?
LimePass. (The electric bike, scooter, and moped company.) Last year, I was notified by Lime that I’m in the top 1% of riders in the world (673 miles in the last two years). I can leave my apartment at 8:50 a.m. and in 10 minutes be in a video conference with a cold brew. It’s another of my time hacks.
Where’s your go-to wristwatch from?
I’m a minimalist, so no wristwatch. The last watch I still own is a Tag Heuer that my father gave me for graduating high school. Which reminds me, I should probably get it serviced as I haven’t worn it in a decade.
The necessities
How do you get your daily coffee fix?
It’s a Starbucks Cold Brew, light ice, as regular ice means half as much coffee. Right before I unlock the Lime scooter, I order my cold brew.
After the cold brew, I am a Diet Coke connoisseur, which is only natural after drinking at least four a day for the past 20 years. I was having dinner with the Pepsi executive team at Cannes a few years ago, and my loyalty to Diet Coke had me request one from the waiter. We did not win that business that day.
What about eating on the go?
Read AI uses a service called Peach, which emails you in the morning options on what to eat for lunch, and delivers your choice to your office by noon. This brings efficiency not just to me, but the entire team at Read AI.
Where do you buy groceries?
Amazon Fresh and I are besties. It knows what I like, makes that list easy to access, and delivers it right to my door.
How often in a week do you dine out versus cook at home?
DoorDash and UberEats regularly fight for my attention. Where dinner is chosen based on what I can order online, and on my route to and from work.
Where do you shop for your work wardrobe?
It’s either online, or when I’m gifted clothing. It can be difficult to buy for me when it comes to the holidays or birthdays, but my friends and family can safely guess that I could use another shirt, pair of jeans, or jacket.
What would be a typical work outfit for you?
I wear the standard tech uniform: hoodie, black shirt, jeans, and sneakers. With enough variation of each, one of your first decisions of the day is the easiest.
Are you the proud owner of any futuristic gadgets?
Read AI. It gives me back about 10 hours a week, where AI can make your life simpler by attending meetings on your behalf, giving you nudges on deliverables, and helping discover opportunities that you might have missed. This ability to build a digital twin to improve my productivity has given me the ability to scale in a way that wasn’t possible a few years ago.
The treats
How do you unwind from the top job?
I like to lift heavy things. Last year, I set a goal to reach the 1,000 Pound Club, which means I need to lift a total of 1,000 pounds across bench press, deadlift, and squat. Right now, I’m at the 940-pound club with a goal of finding another 60 pounds to lift by the end of the year.
What’s the best bonus treat you’ve bought yourself?
When I grew up, I played a game called Genghis Khan on the Nintendo. It was a turn-based strategy game that I would spend an entire weekend playing as a 10-year-old. I believe this experience shaped the way that I think about life and business.
When I sold Placed to Snapchat in 2017, I purchased (i) a sealed version of that original video game that was graded, and (ii) a gold coin from that era of the Mongolian Empire when Genghis Khan reigned.
How do you treat yourself when you get a promotion?
I get a lot of joy from giving to others, and this isn’t the charity giving, which I still do, rather it’s the giving to friends and family. My father had always wanted to go to Patagonia with his brothers and sisters and in 2023, I was in the position to make that happen. Money is just a number to keep track [of], but creating time for experiences and the joy those experiences deliver is what you are going to remember.
How many days of annual leave do you take a year?
I do try to take at least two weeks off a year, with one week with my mother, father, brother and his family, and the other week with my friends. Family is more Cabo, while friends are Ibiza and Ko Samui.
Fortune wants to hear from leaders on what their “Good Life” looks like. Get in touch: emma.burleigh@fortune.com.
