Being within the C-suite is a high-pressure job with lengthy hours, board tasks, and intense scrutiny. However what’s it wish to be a prime govt if you’re off the clock?
Fortune’s sequence, The Good Life, exhibits how up-and-coming leaders spend their money and time exterior of labor.
Right this moment we meet David Shim, the cofounder and CEO of software program firm Learn AI.
If you happen to’re craving for a private assistant to take over pesky email-writing and note-taking throughout the workday, then Learn AI simply might need the repair for you.
The $450 million AI-assistant firm out of Seattle isn’t Shim’s first rodeo. The 45-year-old serial entrepreneur has spent the higher a part of 25 years constructing and scaling firms; when he was a pupil on the College of Washington, he developed a shopper buying portal named eccoBay.com, which was acquired by Ebay after simply 4 months. He then went on to discovered LeagueTraders Inc., with a short foray into hedge funds. After 4 years working in operations and advertising companies roles throughout analytics firms like WebTrends and QuantCast, he ditched his nine-to-five life to as soon as once more be his personal boss.
Learn AI has raised over $82 million, with the newest $50 million Sequence B funding spherical valuing the enterprise at $450 million.
Shim’s concept for Learn AI was impressed by a typical annoyance in one in all his govt roles. The Gen X entrepreneur was the CEO of FourSquare from 2019 to 2020, after his advert intelligence firm Positioned was acquired from SnapChat Inc. by FourSquare. As a frontrunner helming many conferences, he seen “ghosts” within the on-line room—unengaged workers with their cameras turned off, typically invited to a name once they didn’t have to be. To save lots of folks’s time and power, David created “clever ghosts:” AI assistants that sit in on discussions, suggest modifications to conferences, and ship out notes earlier than and after the calls.
Learn AI has since raised over $82 million from backers, with the newest $50 million Sequence B funding spherical valuing the enterprise at $450 million. In 2024, it surpassed a million month-to-month customers—and only in the near past, the corporate launched Gross sales AGI, the place customers can “vibe promote” by counting on the AI instruments to assist transfer offers ahead.
Whereas the Seattle-based entrepreneur has loved many wins in scaling profitable firms, he has a lust for all times past the engaging numbers in his checking account. Shim is a self-proclaimed Weight-reduction plan Coke “connoisseur” and avid powerlifter within the fitness center, who has discovered essential enterprise classes from a childhood Nintendo sport. He’s a giant proponent of the easy “tech uniform” of a hoodie and denims. And typically he splurges on journey—which incorporates masking journeys for his family and friends to locations like Patagonia and Singapore.
“Cash is only a quantity to maintain observe [of], however creating time for experiences and the enjoyment these experiences ship is what you will bear in mind,” Shim tells Fortune.
The funds
Fortune: What’s been the most effective funding you’ve ever purchased?
Investing in my final startup, Positioned, at each single spherical till we have been acquired by Snapchat in 2017 for over $200 million. I deferred my wage for nearly three years, rolling it every subsequent spherical at Positioned. In our payroll, I believe I used to be worker #5, although I used to be the founder, as I didn’t straight take a paycheck.
Extra just lately, I invested in an organization known as Dave through a Particular Goal Car (SPV) through a good friend and former colleague, Imran Khan. The SPV invested in $DAVE at $6 in 2023, and most just lately, the inventory is buying and selling at $200 a share.
And the worst?
In my 20’s, I assumed margin was an accelerant, and it was for some time, till I went all-in on a single inventory with margin. I noticed that the unfold from the acquisition worth for College Specialty Inc. was so vast, it was free cash. It was not free cash, and when the merger was cancelled, I rode the road of dropping all the pieces and extra. I’m glad this was early in my profession and web value, because it was an ideal lesson for all my future investments.
Editor’s word: Shopping for on margin is a type of investing with borrowed cash, which amplifies returns in addition to losses. Schooling-supplies firm College Specialty was an acquisition goal in 2005 earlier than Bain Capital and Thomas H. Lee known as off the $1.5 billion deal citing “structural in addition to market-related challenges.”
When you’ve got youngsters, what do your childcare preparations appear to be?
Learn AI, my present startup, is my child. It’s all the time with me and all the time on my thoughts.
“I put on the usual tech uniform: hoodie, black shirt, denims, and sneakers. With sufficient variation of every, one in all your first selections of the day is the simplest.”
What are your residing preparations like: Swanky house within the metropolis or suburban sprawling?
I reside within the South Lake Union neighborhood of Seattle, only a 10-minute Lime scooter trip from the Learn AI workplaces in Downtown. If you happen to got here to my house, you’d discover a minimalist one-bedroom. When you’re a startup founder, you reside and breathe the work, and all the pieces else is secondary together with furnishing your house.
Do you carry a pockets?
Sure, and proper now it has $220 in money, and three bank cards. The American Specific Platinum is my go-to card for large purchases, whereas my Financial institution of America Rewards is for money again. I attempt to avoid the factors optimization, as money again retains it easy.
What private finance recommendation would you give your 20-year-old self?
Spend money on two issues: your self, and the S&P 500. Investing in particular person shares isn’t the best way to construct wealth; spend the time you’d analysis a inventory, investing in your self, increase your skillset. This doesn’t imply keep out of the market; reasonably, persist with the indexes just like the S&P 500, the place they’ve constantly outperformed particular person inventory merchants. The period of time and threat related to selecting particular person shares didn’t justify the marginally higher returns.
What’s the one subscription you’ll be able to’t reside with out?
LimePass. (The electrical bike, scooter, and moped firm.) Final yr, I used to be notified by Lime that I’m within the prime 1% of riders on this planet (673 miles within the final two years). I can depart my house at 8:50 a.m. and in 10 minutes be in a video convention with a chilly brew. It’s one other of my time hacks.
The place’s your go-to wristwatch from?
I’m a minimalist, so no wristwatch. The final watch I nonetheless personal is a Tag Heuer that my father gave me for graduating highschool. Which jogs my memory, I ought to in all probability get it serviced as I haven’t worn it in a decade.
The requirements
How do you get your each day espresso repair?
It’s a Starbucks Chilly Brew, mild ice, as common ice means half as a lot espresso. Proper earlier than I unlock the Lime scooter, I order my chilly brew.
After the chilly brew, I’m a Weight-reduction plan Coke connoisseur, which is just pure after ingesting at the least 4 a day for the previous 20 years. I used to be having dinner with the Pepsi govt crew at Cannes a couple of years in the past, and my loyalty to Weight-reduction plan Coke had me request one from the waiter. We didn’t win that enterprise that day.
What about consuming on the go?
Learn AI makes use of a service known as Peach, which emails you within the morning choices on what to eat for lunch, and delivers your option to your workplace by midday. This brings effectivity not simply to me, however the complete crew at Learn AI.
The place do you purchase groceries?
Amazon Contemporary and I are besties. It is aware of what I like, makes that record straightforward to entry, and delivers it proper to my door.
How typically in every week do you dine out versus prepare dinner at residence?
DoorDash and UberEats commonly struggle for my consideration. The place dinner is chosen primarily based on what I can order on-line, and on my path to and from work.
The place do you store to your work wardrobe?
It’s both on-line, or after I’m gifted clothes. It may be tough to purchase for me in terms of the vacations or birthdays, however my family and friends can safely guess that I might use one other shirt, pair of denims, or jacket.
What could be a typical work outfit for you?
I put on the usual tech uniform: hoodie, black shirt, denims, and sneakers. With sufficient variation of every, one in all your first selections of the day is the simplest.
Are you the proud proprietor of any futuristic devices?
Learn AI. It provides me again about 10 hours every week, the place AI could make your life less complicated by attending conferences in your behalf, supplying you with nudges on deliverables, and serving to uncover alternatives that you simply might need missed. This capability to construct a digital twin to enhance my productiveness has given me the flexibility to scale in a approach that wasn’t potential a couple of years in the past.
The treats
How do you unwind from the highest job?
I wish to raise heavy issues. Final yr, I set a objective to succeed in the 1,000 Pound Membership, which suggests I must raise a complete of 1,000 kilos throughout bench press, deadlift, and squat. Proper now, I’m on the 940-pound membership with a objective of discovering one other 60 kilos to raise by the tip of the yr.
What’s the most effective bonus deal with you’ve purchased your self?
After I grew up, I performed a sport known as Genghis Khan on the Nintendo. It was a turn-based technique sport that I’d spend a whole weekend enjoying as a 10-year-old. I imagine this expertise formed the best way that I take into consideration life and enterprise.
After I offered Positioned to Snapchat in 2017, I bought (i) a sealed model of that authentic online game that was graded, and (ii) a gold coin from that period of the Mongolian Empire when Genghis Khan reigned.
How do you deal with your self if you get a promotion?
I get quite a lot of pleasure from giving to others, and this isn’t the charity giving, which I nonetheless do, reasonably it’s the giving to family and friends. My father had all the time needed to go to Patagonia along with his brothers and sisters and in 2023, I used to be within the place to make that occur. Cash is only a quantity to maintain observe [of], however creating time for experiences and the enjoyment these experiences ship is what you will bear in mind.
What number of days of annual depart do you’re taking a yr?
I do attempt to take at the least two weeks off a yr, with one week with my mom, father, brother and his household, and the opposite week with my associates. Household is extra Cabo, whereas associates are Ibiza and Ko Samui.
Fortune needs to listen to from leaders on what their “Good Life” seems to be like. Get in contact: emma.burleigh@fortune.com.
