Kyle Ladewig is the Founder & CEO of Out Of Office, a company with a mission to help remote workers get out of the house and meet people while they work.
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1) To kick things off, could you tell us a little about your career background and current role?
I started my career in commercial real estate and I still think of myself as a “real estate guy,” even though I’ve been working at tech companies for the last 6 years. You can stalk me on Linkedin if you want my resume, but it’s probably more interesting to hear what I learned from each job and how my experiences led to founding Out Of Office.
When I was 22 I was a commercial real estate broker in San Francisco, selling buildings worth tens to hundreds of millions of dollars. That job taught me how to prepare for meetings, how to sell, and how to act older than I was.
I quit brokerage and stumbled into a few consulting projects for startups trying to break into the real estate industry. I turned those gigs into a one-man consulting company for 5 years, where I did everything from running sales at ClassPass to helping Lyft develop a strategy for autonomous cars.
Sometimes I was working for 4 companies at once, so I learned how to manage my time and set expectations with executives. I also learned that office politics are very real and, for better or worse, as a “consultant” you can jump in and out of the drama because there’s some arms-length separation.
I founded Out Of Office a couple years ago with Steve Flory, to tackle the problem of finding a great place to work when you work remotely. Out Of Office combines a lot of my passions, from reimagining real estate to connecting people in real life and empowering professional independence.
2) What does a day in the life look like for you? Can you take us through a recent workday?
I’m an early riser, at least by most tech startup standards. I’m usually up by 6:30AM and in a workout class by 7AM. I know if I don’t workout in the morning, I’ll never get around to it.
Plus it’s nice to start my day focusing on something other than work, and exercise gives me an energy boost going into the workday. Most days I’m hosting a Work Club in San Francisco, so that’s usually my second stop.
As CEO, it’s my job to do the stuff that doesn’t clearly fall under anyone else’s job description, and to remove blockers so our team can do what they’re really good at. So I’m constantly context switching throughout the day, which is one reason I love being at Work Club.
Having a crew of coworkers helps me stay focused and avoid feeling stressed about all the priorities I’m juggling.
3) Does your current role allow for flexible or remote working? If so, how does that fit into your life and routine?
Not only is Out Of Office a distributed team, but we’re also building apps for remote work, so our mission and our lives are all about flexibility. We start every day with a 15-minute video standup at 8:45AM. Most days, between the morning standup and Slack/Asana, everyone is clear on priorities and what they’re responsible for.
We hire domain experts with 8+ years experience who are comfortable with the ambiguity and unpredictability of a startup. That means I spend very little time worrying if mistakes are being made, and almost no time worrying if everyone is being productive.
4) What does work-life balance mean to you and how do you work to achieve that goal?
I said before that I don’t worry about whether our team is working, but I do worry about everyone’s work-life balance. In fact, our official mission statement is “We give you a great place to work, so that you can better balance your life.”
So we have an unlimited PTO policy, fully covered health insurance, and stuff like that. Day to day, luckily we’re building a product (Work Club) that forces us to get out of the house and interact with other people in real life.
We genuinely enjoy doing it too, because remote work just isn’t sustainable if you’re spending 40+ hours a week alone on your couch – humans need human interaction to survive.
5) What do you think are some of the best habits or routines that you’ve developed over the years to help you achieve success in your life?
The first is that I’m obsessive about staying on top of my email. My inbox isn’t always at zero, but it’s pretty damn close. I don’t know when I developed this habit, but I think subconsciously I’m so appreciative when people are responsive that I want everyone to think the same about me.
The second habit is a trick to expand your network – I learned this from a mentor of mine when I was looking for my first job out of college.
You’ll be shocked by how many people will take meetings from cold emails, as long as you put thought into the message and make it insanely easy for them to say yes (include 4-5 times you can meet and offer to go to them). But the trick is about turning one meeting into two or three, by asking people for intros to other people they recommend you meet.
In general, people love being helpful and they love flexing – introducing two smart people is a great way to do both. If you don’t ask for intros, chances are you’ll never get them.
6) Are there any books that have helped you improve over the years?
I’ve worked on a lot of marketplace businesses, and the best book I’ve read on the topic is Who Gets What And Why by Alvin Roth, followed closely by The Platform Revolution by James Foster.
If you want to sell – and everyone needs to sell at some point – you should read Pitch Anything by Oren Klaff (twice) and Building a Story Brand by Donald Miller.
Finally, if you want some philosophical stuff that’ll change your perspective on life, read all three books by Yuval Harari (don’t stop at Sapiens) and Being Mortal by Atul Gawande.
7) What is the number one thing you do to make sure you get the most out of your day?
This isn’t really a “thing to do,” but more a perspective to have. In most jobs, including mine, the decisions you make aren’t life or death. The same goes for mistakes – there are very few career-ending mistakes you can make in one day.
If you sweat the small stuff, you’ll go to bed stressed every night wake up feeling like you’re already hours behind. The easiest way to stay focused on the long-term is to be comfortable with a few mistakes and bad days every now and then.
8) If you could read an interview about work-life balance by anyone, who would that be?
I’m a big Kanye West fan, so I’d read any interview with him. Especially when it comes to work-life balance, because the guy has had multiple successful careers (musical artist, producer, fashion designer, etc.) while also raising a family. Plus, he’s struggled with mental health issues, and that’s a topic that needs to be de-stigmatized.
9) Do you have any last thoughts on work, life or balance that you’d like to share with our readers?
It’s pretty clear that the biggest workplace change over the next 5 years will be the exponential growth of remote teams. Big cities are too expensive, hiring top talent is super competitive, and most people’s work fits in a backpack so I don’t see how companies can keep employees locked up much longer.
But, like most workplace trends, everyone tends to focus on the benefits and ignore the risks. If you think remote work has no negative side effects, you’re gonna screw it up.
The number one problem remote workers face is dealing with isolation and loneliness – we think we have a solution with Work Club, and I’d love to hear ideas or feedback from the BTG community! If you’d like to learn more about Out Of Office & Work Club, check them out here!
If you’d like to have a conversation with us about how you balance the grind, get in touch with us!