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 Degreed’s founder and co-CEO, David Blake.
The 41-year-old serial entrepreneur started out as a management consultant for Oliver Wyman in 2007, but his heart wasn’t in it. Blake’s true passion lies in education—and he has since dedicated his career to improve learning for students and employees alike.
Blake leads the $1.4 billion education technology company a long ways away from Degreed’s Silicon Valley roots. He moved to Salt Lake City Utah in 2020, where he's embracing little breaks from the chaos of the tech world
Blake’s lifestyle is working in unison with Degreed’s pace of growth; the business’ career-building programs are used by 30% of the Fortune 500 with over 50 million skills rated to far, and 460,000 learning pathways for the 10 million activated users. For the co-CEO, that means balancing a hectic schedule with frequent naps (taken anywhere) and binge-watching survival TV. He also sneaks in some video games between his other duties as the co-founder of BookClub and advisor for several companies like Sounding Board, Transfr VR, and OnDeck.
Despite a long list of to-do’s, Blake’s passion for education keeps the fire burning. Before starting Degreed in 2012, he was a founding team member at Zinch—a company that helped students find scholarships, acquired by $12 billion learning giant Chegg—and was selected as a top edtech entrepreneur by the Stanford School EdTech Lab. And even when he’s off the clock, education is still a huge part of his life: Blake and his wife run a microschool, where they teach their three children.
“I’ve dedicated my life to the future of education, and I wanted my children to benefit from those principles,” Blake tells Fortune. “I didn’t want my kids to be like the cobbler’s children with no shoes.”
The finances
Fortune: What’s been the best investment you’ve ever bought?
I spent about $15 on the book titled, The Millionaire Next Door. It reframed for me, early in my life, what the definition of success to be, and therefore in which ways and direction I’d strive with my life. This book is still guiding me today. I specifically recall a Buddhist teaching from the book, which was also picked up by Chuck Palahniuk and popularized in Fight Club, that ‘you own your stuff and your stuff owns you.’
And the worst?
Have you ever seen the movie Money Pit? I bought one of those.
If you have children, what do your childcare arrangements look like?
The most unique approach we’ve taken to parenting our three children is that we started a microschool. I’ve dedicated my life to the future of education, and I wanted my children to benefit from those principles. I didn’t want my kids to be like the cobbler’s children with no shoes.
What are your living arrangements like: Swanky apartment in the city or suburban sprawling?
As it turns out, homes weren’t built to run a classroom, so after a decade of living in San Francisco, we cast a wide net and looked for the right house in multiple states to be able to run our microschool. We ended up finding it in Utah, and moved back there in 2020. It’s been full on, suburban life for us ever since.
I am a big advocate for naps, and I can take them just about anywhere.
How do you commute to work?
When I am home, I commute by car. I enjoy the drive because it’s a great time for me to listen to audiobooks or podcasts, which help me stay current and sharp on a variety of topics.
Some of my favorite podcasts: Smartless, Room for Two, Faith Matters, Acquired, The Moth, The Weekly Show. Some of my favorite recent audiobooks: The Anthropocene Reviewed, I Hate the Ivy League, Blitzed, Greenlights, We Are Legion (We Are Bob)
Do you carry a wallet?
I haven’t carried a real wallet for nearly 15 years. I use a MagWallet attached to the back of my iPhone (no phone case, the way Steve Jobs intended), which holds my driver’s license and one credit card, which I rotate when I am traveling for work.
Do you invest in shares?
I focus my investing on private tech companies, a space I know well and where I can contribute both financially and with expertise. This familiarity allows me to vet deals effectively and support entrepreneurs meaningfully.
While this approach isn’t optimized for the highest yield, it aligns with my goal of making an impact. Helping good entrepreneurs succeed and generating meaningful returns is a win-win. As expected with early-stage investing, some deals have gone to zero. However, many have yielded returns, and a few, like Transfr and Podium Education, have been breakout successes.
What personal finance advice would you give your 20-year-old self?
Invest in Bitcoin.
What’s the one subscription you can’t live without?
Drift Co Scent-of-the-month. It’s a small luxury for $10 per month, and so good. Smell is the most underrated sensory experience and this little luxury makes me incredibly happy.
Spotify is my longest-standing subscription. With kids in the house, it’s non-negotiable—they’d revolt if I ever turned it off!
Where’s your go-to wristwatch from?
What is time? I haven’t worn a wristwatch since I got my first cell phone. I aspire to one day purchase a Patek Philippe with the moon phases for my father. When I was young, he wore an inexpensive watch with the moon phases that I always loved.
The necessities
How do you get your daily coffee fix?
I’m Mormon, so I grew up without coffee. If you’ve seen Secret Lives of Mormon Wives (which I haven’t, but know the buzz), you know that Utahn’s are really just soda fiends. Dr Pepper Zero Cream Soda is my pick.
I’m sharp and at my best in the morning, so no caffeine is needed. I hit a slump at ~3:00pm every day, and power nap when I can. I am a big advocate for naps, and I can take them just about anywhere.
What about eating on the go?
In my 20’s it was a cheesesteak or a burger. In my 30’s it became a turkey sandwich or a burrito. Now that I am in my 40’s, it is salad+protein. My eat-what-I-want metabolism has betrayed me lately.
Where do you buy groceries?
Instacart.
How often in a week do you dine out versus cook at home?
I love cooking! My daughter does as well. She wants to be a chef and has taken over the family meals for 3-4 nights out of the week. My wife and I do date-night each weekend, and will eat a nice meal out and we try to host friends or family Sunday night.
Where do you shop for your work wardrobe?
The more senior the role in my career, the more I get to dress as I wish, and less as others expect. I was CEO by my late twenties, so it’s been a while since I was wearing anything besides what feels right.
I will say, as a Silicon Valley tech exec, the few times I’d wear a suit it was for foreign travel/meetings, where I was trying to respect their cultural nuances. What I’ve found is that people are often disappointed to find a tech exec dressed formally–I think they want to see the ‘hoodie & sneakers’-cliches played out.
Right now, my favorite piece in my closet is a jacket made by a friend, under her brand Bravo Charlie, who does vintage reclamation. She made me a jacket from a vintage sleeping bag–it’s amazing and is a conversation starter anytime I wear it.
What would be a typical work outfit for you?
Jeans, t-shirt, sneakers and a jacket.
Are you the proud owner of any futuristic gadgets?
Carv, it’s hardware that attaches to your ski boots to enable real-time, AI coaching as to how you are doing and what you can improve on in your skiing.
The treats
How do you unwind from the top job?
How do I manage stress? Napping, working out, stress eating, and during some chapters of the journey – therapy/coaching.
How do I spend my free time? With my wife and kids, running, skiing, video games (Polytopia), and my guilty pleasure: survival-TV shows.
What's the best bonus treat you've bought yourself?
At a major milestone in my entrepreneurial journey, I made a personal splurge and purchased an industrial orange juice maker.
When we acquired a startup in The Netherlands, I moved over there for a summer with my family. Each day, I’d stop at a little market to purchase fresh squeezed orange juice then walk through the quiet streets and bridges over the canals to the office.
Fresh orange juice takes me back to The Netherlands every time. It’s a hit of nostalgia and charm with every glass.
How do you treat yourself when you get a promotion?
I opt for bucket-list travel. For our 10th wedding anniversary, we biked our way through Thailand! I still consider that to be a trip of our lifetime.
Take us on holiday with you, what’s next on your vacation list?
I travel almost every week, and my family often joins. Beyond that, I only take 2-3 weeks of work-free holiday per year. This time is reserved for lake trips, where days are spent waterskiing, fishing, exploring, swimming, and cooking; ideally, without WiFi.
The quintessential trip as a Utahn isn’t to Zions or Arches National Park; it is to the National Recreation Area, Lake Powell. It’s the beauty of southern Utah’s grand red rock formations, but with the fun and recreation of water.
How many days of annual leave do you take a year?
As co-CEO, my schedule demands almost weekly travel, much of it international. My family has taken the approach of traveling together as much as we can, and much of that is anchored in my work travel as well as trips where they are on holiday and I’m working remotely. So, I’m able to travel with my family 5-6 weeks per year, but reserve the days off for days on the lake.
Fortune wants to hear from leaders on what their “Good Life” looks like. Get in touch: [email protected].
This story was originally featured on Fortune.com
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