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 Jonathan Siddharth, co founder and CEO of AI company Turing.
Siddharth helms a $2.2 billion business building large language models (LLMs) for industry powerhouses like OpenAI. But his passion for technology predates his founding of the unicorn company in 2018; as a teenager, he wanted to fuse his passions for AI and Formula 1. So he started a hobby project where he programmed a neural network to drive a car. The entrepreneur says that an early venture helped him eventually get into Stanford University, where he pursued a master’s degree in computer science.
“I have been fascinated by artificial intelligence since high school, when I began tinkering with neural networks before the subject was even taught in class,” Siddharth tells Fortune. “I would raid the library for every book I could carry, captivated by the idea of algorithms inspired by biology.”
Turing secured a $111 million Series E funding round this March, which doubled its valuation to $2.2 billion.
While getting his master’s degree, he met his future cofounder, Vijay Krishnan. Together, the pair launched an AI-powered discovery engine, Rover, in 2008. It received early acquisition offers from the likes of Google and Twitter, but the duo declined; at one point, Rover was even number one on Apple’s App store for content recommendations. They sold the company less than a decade later to Revcontent, and soon after, Siddharth got back on the horse.
“I felt an unfinished quest,” the serial founder says. “Rover had been a good outcome, but not yet in the league of companies I admired.”
One year later, Turing was born, named after the famed computer scientist Alan Turing. The business sought to tackle the talent problem it faced at Rover by using AI to identify world-class engineers and began placing top developers on cutting-edge teams. Then, everything changed when OpenAI came knocking. The AI behemoth asked Siddharth’s team to help GPT-3 learn how to code and use tools. ChatGPT was released just a few months later—its coding ability powered by Turing’s data—which Siddharth called a “proud parent moment.”
Today, Turing builds real-world AI systems for Fortune 500 companies across banking, insurance, retail, and advanced tech. It also partners with major AI labs to push the needle on coding, reasoning, and agentic workflows. In March, Turing secured a $111 million Series E funding round, which doubled its valuation to $2.2 billion. Alongside the AI business, Siddharth has served on the board of Quora, and continues to invest and advise startups through Stanford’s accelerator program StartX.
The CEO is constantly on the grind, having never taken more than two weeks off in total over the past seven years while scaling Turing. But when he finally gets a moment to unwind, it’s still all tech, all the time. Siddharth plays racing games on his PlayStation 5 and is “one of those rare humans” who actually likes Apple Vision Pro. He loves fast cars, Starbucks, and Domino’s pizza, and lives by a minimalist mindset to free up his brain for Turing.
“My love of Formula 1 and AI shapes elements of Turing’s culture: a relentless human-machine feedback loop where both driver and car push each other beyond previous limits and focus on learning rate,” Siddharth continued. “That ethos guides our pursuit of performance.”
The finances
Fortune: What’s been the best investment you’ve ever bought?
A top-of-the-line Kindle, around $300. The return on ‘joy-per-dollar’ is unbeatable. I’ve devoured countless AI texts, sci-fi epics, and entrepreneur biographies on its warm e-ink screen. If I could pack only one device besides my iPhone, the Kindle wins every time.
And the worst?
My attempt at being a “grown-up” with my car choice. After becoming a dad, I convinced myself I needed something more sensible and mature. So I sold my Porsche 911 convertible and bought a high-end sedan with all the luxurious bells and whistles.
It looked great on paper—quiet, comfortable, de-stressing, loaded with high-tech gadgets and AI—but after about ten months, I realized I’d made a mistake. I never had time to drive it, and when I did, I missed the raw exhilarating thrill of a sports car. I never felt like taking it out just for a joy ride.
I ended up selling it and learned two important lessons: first, I should stick with what genuinely brings me happiness rather than what I think I “should” have at this stage of life. Second, no half measures. We now have a lovely Honda minivan for the kids and it is a phenomenal family car with a mobile changing station. And I’m in the market again for a convertible sports car with two seats. Two focused tools for two different applications.
Within the first 15 to 20 minutes of meeting a founder, I can usually tell if they’re someone who will expand my thinking over time.
If you have children, what do your childcare arrangements look like?
When it comes to childcare, we’ve established a flexible arrangement that adapts to the unpredictable schedule of leading a high-growth company.
We rely on trusted help for specific situations like date nights with my wife or when work demands spike, but we’re also intentional about creating family time that’s fully present and engaged. My wife also has help that comes in periodically for babysitting.
The biggest lesson I’ve learned is that there’s no perfect system. It’s about constantly adapting and finding what works for your specific family situation while ensuring your children get the attention and care they deserve.
What are your living arrangements like: Swanky apartment in the city or suburban sprawling?
Our house has a beautiful backyard that provides a quiet retreat from the intensity of the tech world. What I appreciate most about our location is that we’re just a stone’s throw away from a lovely park—it’s become a central part of our family routine and connects us with our community. The location strikes a perfect balance for me. We’re close enough to Stanford to tap into that innovation hub, yet far enough away to have space and tranquility.
I’m also strategically positioned between SFO and San Jose airports, which is crucial given how frequently I travel—I’ve refined my airport timing to an art form, sometimes…Okay, most of the time, pushing the envelope by leaving just 1.5 hours before an international flight.
How do you commute to work?
I typically Uber and my car becomes my mobile command center: I usually take non-stop Zoom meetings on the go and have a “to call” list while on the move. There’s a special kind of victory in turning mind-numbing traffic time into productive work hours—it’s like stealing time back from the Bay Area commute gods.
Do you carry a wallet?
I’m a minimalist when it comes to what I carry—I’ve engineered my pocket contents with the same ruthless efficiency our developers apply to eliminating redundant code. Rather than a traditional wallet, I carry three essential cards: a credit card, debit card and my ID. That’s it.
This streamlined approach removes unnecessary bulk and simplifies daily life. The fewer items I need to keep track of, the more mental bandwidth I have for the things that truly matter.
Do you invest in shares?
I have most of my eggs in one basket, which is Turing.
For my personal financial portfolio, I just invest in index funds and don’t think much about it. I also invest in select AI startups and companies like Aida, Fastrak.ai, Create.xyz, Toma and Parallel.ai, which are all primarily started by people in my network and aim to automate support, product management and product development.
My investment philosophy is quite simple: I ask myself whether I’d want to spend time with the founder. I like super smart, hard-charging founders going after a big market. This approach aligns with something I’m passionate about: improving my own learning rate. I want to surround myself with exceptionally smart people I can learn from. Within the first 15 to 20 minutes of meeting a founder, I can usually tell if they’re someone who will expand my thinking over time. I tend to invest very early in companies where I see this potential for mutual growth and learning.
What personal finance advice would you give your 20-year-old self?
Remember to have some fun along the way. Outside of all the work that you’re focused on, don’t forget to balance ambition with taking time to smell the roses. Or, in AI terms, your objective function should be some type of joint optimization around creating business impact and having fun.
Looking back, I realize that while building companies and pursuing big goals is incredibly rewarding, there’s also tremendous value in enjoying the journey. Financial success means little if you haven’t allowed yourself to experience life’s pleasures along the path to achieving it.
Sometimes the best investment is in creating memories and experiences that give you perspective and keep you grounded. The drive to succeed is important, but so is pausing occasionally to appreciate what you’ve already accomplished. I’m still working on this since my default is to always pick the next hill to climb and not look back.
What’s the one subscription you can’t live without?
ChatGPT Pro, hands down. ChatGPT has become absolutely indispensable to my workflow. It’s transformed how I approach problem-solving, research, and even everyday tasks. If a computer was a bicycle for the mind, AGI is like a jet engine.
Where’s your go-to wristwatch from?
I’m a relatively new watch nerd, but I’ve developed an appreciation for the Jaeger-LeCoultre Reverso. What fascinates me about this timepiece is its dual-face design—you can flip the watch to reveal a different face on the opposite side.
The Necessities
How do you get your daily coffee fix?
I spend what can only be described as a small fortune on Starbucks every year. My go-to order is a triple tall nonfat latte with three pumps of classic sugar—admittedly not the healthiest choice, but it fuels my day. During the holiday season, I become slightly obsessed with their gingerbread lattes.
There’s something about that ritual of stepping into a Starbucks, wherever I am in the world, and getting that familiar cup that helps create a sense of consistency in an otherwise unpredictable schedule. That dependable caffeine boost has become an essential part of my daily rhythm.
The former CEO of Starbucks is a friend and I can see that in their in-store experience—the barista training and culture—that this is something they are very intentional about.
What about eating on the go?
I often eat on the go! Most of my meals happen at my desk or between meetings. Being vegetarian, I gravitate toward simple options that can be eaten quickly and discreetly during Zoom calls.
When I travel internationally for conferences like ICLR in Singapore, I have a guilty pleasure: seeking out familiar chains like Pizza Hut, Taco Bell, and Domino’s. There’s something about these places in Asia. For some reason, in my opinion, the food tastes better compared to their U.S. counterparts! This contrasts with our Turing team offsites, where I stick to a predictable routine—just get me a veggie sub from Subway and a Red Bull, and I’ll be good.
The only exception to my on-the-go eating habit is dinner with family, which I prioritize. In the current pace of the AI industry, traditional meal times often get compressed or repurposed as working sessions, but those family dinners remain sacred.
Where do you buy groceries?
Honestly, I actually don’t know! Groceries just appear in our home thanks to my wife. She has a very high bar for what’s healthy and nutritious (she is actually a certified nutritionist), so I’ve happily entrusted this aspect of household management to her.
How often in a week do you dine out versus cook at home?
I order in frequently. With the demands of running Turing and family life, efficiency becomes paramount. We often have food delivered rather than cooked at home—there is a wonderful woman-owned start up called Planted Table that we love. They offer organic, whole food meals delivered right to your door. We are big fans!
When I do dine out, it’s typically for work meetings with my team, customers, or candidates. Evvia in Palo Alto and Madera at the Rosewood Sand Hill are some of my favorites. Rosewood holds special significance for me since it’s where I proposed to my wife, having created an elaborate ruse involving a fake Saturday “offsite” meeting with my team. The Rosewood has been the site of many important Turing milestones since then, so despite being somewhat of a Silicon Valley cliché, it remains a personal favorite.
During my personal time, I try to eat at home when possible, with guilty pleasures including South Indian food (especially dosas, which are like thin crepes from India) and, I’ll admit, Taco Bell and Domino’s.
Where do you shop for your work wardrobe?
I’m a big fan of online shopping. My wife serves as my head of design in this department, as she’s very savvy about what to wear. Currently, I really like Quince and Lululemon, particularly their performance fabrics that are great for travel. I’m drawn to clothes you don’t have to press or think much about.
My approach to wardrobe is minimalist by design. I want to eliminate decision fatigue. My closet is mostly grayscale: black or white shirts, simple jeans—with multiple versions of the same items. About 50% of the time, my black t-shirts will have a Turing logo on them.
I apply what I call the “barbell strategy” to my clothing: really basic everyday items on one end, and a couple of nice suits that I splurge on at the other. There’s very little in between. I either dress very comfortably or dress up formally; nothing in the middle. This approach saves mental bandwidth and simplifies my routine, allowing me to focus on more important decisions throughout the day.
What would be a typical work outfit for you?
A typical work outfit for me would be a black t-shirt or shirt and blue jeans, with the t-shirt featuring a Turing logo about half the time. I deliberately keep my daily wardrobe simple and consistent. I usually operate at the extremes: either very comfortable casual wear or formal business attire, with very little in between. My wardrobe adapts to context, especially when traveling between casual Silicon Valley settings and more formal international business environments.
I have a particular fondness for my first Turing-branded jacket—it’s become something of a personal trademark. For important meetings or events, I’ll upgrade to one of my few nice suits that I actually do splurge on, but that’s reserved for occasions that truly call for it.
Are you the proud owner of any futuristic gadgets?
I’m a huge gadget nerd; virtually everything in the Apple Store has found its way into my home, and I’ve even converted my parents and in-laws to Apple’s ecosystem. I’m one of those rare humans who owns and actually enjoys using the Apple Vision Pro. While it’s not at a price point that’s sustainable for mass adoption (at nearly $5,000), it offers a fascinating glimpse into the future of augmented reality.
My passion for tracking and measurement led me to simultaneously monitor my heartbeat through three different devices at one point: my Oura ring, Whoop band, and Apple Watch. I tend to overdo it with devices! Recently, I placed an order for the PlayStation 5 Pro to play racing games…As a teenager, I was obsessed with racing games like Need for Speed: Porsche Unleashed, which featured only Porsche cars.
My most recent acquisition that I’m particularly proud of is a Moleskine smart notebook. What I love about it is how discreet it is; it looks like a regular notebook with a regular pen, but it automatically transcribes my writing to an app on my phone, captures sketched diagrams, and records voice. I’m drawn to “under the radar” tech: devices that don’t broadcast their technological sophistication.
The Treats
How do you unwind from the top job?
When I can carve out the time, I escape into reading and gaming—particularly racing games like F1 and Need for Speed—which provides the perfect cognitive context-switching after a day of meetings. It’s actually a nostalgic connection to my roots in AI; my first serious coding project was programming a neural network to drive a car, which ultimately helped me get into Stanford.
What’s the best bonus treat you’ve bought yourself?
My most recent splurge wasn’t actually for myself. I bought Taylor Swift tickets for my wife. Taking that time off together was the real treat. Sometimes the most meaningful indulgences aren’t about acquiring things for yourself but creating experiences for the people you care about.
How do you treat yourself when you get a promotion?
As a founder and CEO, traditional promotions aren’t really part of my journey anymore, but I do celebrate meaningful company milestones. The honest truth? My first reaction after closing a big round or deal is pure relief followed by exhaustion. After working intensely for weeks, months, or years, my celebration typically begins with an uninterrupted 8 to 12 hour hibernation—sleep is the ultimate luxury when you’ve been running on adrenaline.
My celebration style continues with deliberate solitude—reading a book or going for a drive alone to decompress, followed by a date night with my wife, where we talk about anything but work. While we certainly celebrate as a team, I’ve learned that creating space for quiet reflection helps me recharge before the inevitable moment—usually within 24 hours—when my mind starts racing about how to 10x whatever we just accomplished.
Take us on holiday with you, what’s next on your vacation list?
My vacations fall into three distinct categories. First, there’s family time—we recently escaped to Hawaii, where we embraced what I call the ‘vacation bubble’ at resorts where you can stay on property and enjoy the amenities. Dating profiles might glorify hiking and adventure, but my ideal getaway involves minimal movement and maximum relaxation, though traveling with two very young children certainly keeps things interesting!
For the second category, I reconnect with friends for more high-energy experiences—concerts or Formula 1 races. After experiencing the Miami Grand Prix last year and even taking a hot lap with the Mercedes F1 team, I’m eyeing Monza in Italy next. And then, there’s my automotive passion bucket—I’m planning to attend the Pebble Beach Concours d’Elegance, though for now I’m the guy who pulls up to Menlo Park Cars and Coffee in a minivan.
Beyond leisure travel, family connections remain essential—regular visits to India where my parents live—provide grounding amid the intensity of the AI world.
How many days of annual leave do you take a year?
I should preface this with some humor—while we have unlimited PTO at Turing, and I’m a firm believer that people need regular time away to recharge, I’m probably the biggest offender when it comes to not taking enough time off. The honest answer is “not much.”
I don’t think I’ve taken more than two weeks in the past seven years since starting Turing, and even in those two weeks, I’m not really out and usually end up working on something. The reason is that I have a hard time switching off my brain, which is a product of my personality. Entrepreneurship is something I live and breathe, and it’s intertwined with my passion for AI. With technology advancing at such a breathtaking pace, it’s challenging to step away for extended periods. That said, I recognize this isn’t sustainable or something I should model for our team. Like many founders, I’m working on practicing what I preach about the importance of disconnecting occasionally. It remains a work in progress!
