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The Surprisingly Simple Strategy This Founder Uses to Stay in Control of His Schedule

Imgur founder Alan Schaaf swears by this two-step process.


Editor’s Note: Entrepreneur’s 20 Questions series features both established and up-and-coming entrepreneurs and asks them a number of questions about what makes them tick, their everyday success strategies and advice for aspiring founders.

Courtesy of Imgur

If there is a meme that is suddenly everywhere, it very likely got its start on Imgur, the online image sharing community. Case in point: 2015’s black/blue versus white/gold dress.

In 2009, Alan Schaaf started  Imgur for just $7 (the cost of a domain name) from his dorm room at Ohio University. The business started as a tool to make it simpler to upload and host any kind of images on the web -- not just photos, but photoshopped images, screenshots and GIFs as well.

Since it’s dorm room launch and unveiling on Reddit, Imgur has grown to become one of the most trafficked sites on the internet. The company now has 150 million active users and more than 5 billion pageviews each month.

Schaaf believes that the community has grown the way it has because while many social platforms are utilized to further a personal brand, “Imgur offers a rare place for people to express themselves in a real way without the fear of social judgment,” adding, “Everyone has an equal chance of sharing their story to millions of people, because it’s not about who you are, but about the quality of your content.”

The company has had some major milestones over the last few years. In 2014, Imgur received it’s first and so far only investment: $40 million from and Reddit. And in 2015 it hit 150 million monthly active users and won the Webby Awards for Best Social Media and Best Community Website.

We caught up with Schaaf for our 20 Questions series to find out what motivates him and makes him tick.

Interview was edited for length and clarity.

Related: Take Back Your Mornings (Infographic)

1. How do you start your day?
When I come into the office the first thing I do is I plan out what I want to accomplish that day. I write it down in my notebook and make sure I accomplish it before I leave that day.

2. How do you end your day?
I go through that notebook and review any notes that I took, and I check off everything on the list. I also walk the floor and chat with people and see what they are working on and how their day has gone.

3. What’s a book that changed your mind?
I don't have much time to read. I'm more of a problem solver. I'll have an idea or a problem and I'll learn what's necessary in order to do the idea or solve the problem. If I need to read a book then I will, but it usually comes down to researching on the internet and reading blog posts.

4. What’s a book you always recommend?
One of my favorite sci-fi books is Ender’s Game by Orson Scott Card. I would recommend it to anyone who loves sci-fi. It’s a perfect intro to sci-fi.

5. What’s a strategy to keep focused?
My routine of writing down what I want to accomplish every day is something I developed pretty early on working on Imgur.

I bootstrapped the business for five years.It was really just me the first two years. That meant I wore every hat that exists, and I figured out the only way I can accomplish things is to map them out, make sure I don’t get distracted and accomplish what I set out to do at the beginning of the day.

6. When you were a kid what did you want to be when you grew up?
I wanted to be the guy that rode on the back of the garbage truck and threw garbage in the back. When you're 4 years old and you see guys hanging off the back of a big truck that's driving down the street, it's pretty exciting!

Related: Inspire Loyalty With Your Leadership: Here's How

7. What did you learn from the worst boss you ever had?
I’ve never had a boss. What I have learned about management is that everyone is different -- there is no one perfect strategy. Different people respond to different things in different ways. To be a good manager, you have to figure out what motivates that particular person.

8. Who has influenced you most when it comes to how you approach your work?
My parents. Ever since I can remember, my mom has been self-employed. She used that term, but she was actually an entrepreneur. She wanted to do it herself, she didn’t want to hire employees, wanted to support herself and her family by what she loved doing. That was inspiring.

And another quality she has is if there is work to be done, she does it. She’ll just figure out a way to do it and do it. I learned a ton from that: to be scrappy. You don’t need to hire professionals, there is always a way to get it done. Nothing ever blocks you except for yourself.

My dad used to be a lawyer and then stopped and moved to Thailand to teach English 10 years ago. I see how his life is exactly how he wants it to be.

One time he was sailing and found a patch of land. He docked his boat, traveled around the town, tracked down the guy who owned the land and bought it. He built his own house on the land exactly how he wants. That’s super motivating: You have the ability to drop everything and do what you want to do how you want to do.

9. What’s a trip that changed you?
The first trip to visit my dad in Thailand. That trip was the first time I was really out of the country and experienced a completely different part of the world. It was beautiful, and everything was completely different than it is in the U.S. It made me want to see more of the world, and since then, I've traveled to 20 other countries and plan to see as much of the world as possible.

10. What inspires you?
The goal that JFK set for the U.S. to accomplish: put a man on the moon before the decade was out. He inspired an entire nation to reach for the stars. He didn't know how we were going to do it, but he knew we must try.

And in 1969, we did it. I think about that goal and mission, and because of it, set ambitious goals for myself and for my company. Even if I don't know exactly how we're going to accomplish them at the time, I know that doing so is necessary for us to have a big and meaningful impact on the world.

Related: Buzz Aldrin Wants You to Know -- the Sky Is Not the Limit

11. What was your first business idea and what did you do with it?
My first business idea was a company called Soft Administrative and Networking Solutions. I was 15 and I knew a lot about computers, so I traveled around to different people in Granville, Ohio and fixed their computers. Technically, my mom drove me around. When I went to college I transitioned the business over to a friend, and he took over my clients.

12. What was an early job that taught you something important or useful that you still use today?
In college I started working at a technology call center. It taught me how to work with people, and it taught me a lot of patience. We would help people with anything -- some programs we had never heard of before. We would just Google it and then walk the person through on the line.

13. What’s the best advice you ever took?
As you go throughout your day, write down thing that energize you. It could be anything -- talking to someone, eating lunch.

You also need to write down the things that drain you. It could be different types of meetings or projects. You do this for some time and after awhile you find common themes.

Use this to try to neutralize your energy at the end of the day. Take control of your schedule, so you don’t burn out.

14. What's the worst piece of advice you ever got?
I don’t remember the worst advice. It was probably so bad that I wrote it off.

Related: You Must Stop Doing These 5 Things to Be Productive

15. What’s a productivity tip you swear by?
Coming in at the start of the day and writing down what I want to accomplish.

16. Is there an app or tool you use to get things done or stay on track?
Google Keep, a note-taking app by Google. I walk around with my notebook all day. If I don’t have my notebook, I use that, and it syncs to all my device.

17. What does work-life balance mean to you?
Work-life balance doesn’t mean a lot to me. I have work time and decompress time, but work doesn’t only have to be related to Imgur. I always have a part of my life where I’m building or working towards something new.  

18. How do you prevent burnout?
I have to take what I call decompress time. I have to stop working towards something and just entertain myself. I love playing video games. It’s mindful to me that I enjoy something that doesn’t line up to building something. It’s just pure enjoyment. I turn off my brain, so I can then set out to do something meaningful at a later time.

19. When you’re faced with a creativity block, what’s your strategy to get innovating?
You have to go someplace different. Get out of your environment. We have break out spaces in the office. One is called the Cave, It’s a nice quiet space with no windows that I like using. I learned in college that I could not study in my apartment. So, I found a bunch of nooks and crannies in the library, and as soon as I would enter those spaces, all the creativity would come back.

20. What are you learning now?
I’m a programmer at heart. Now I’m learning as much as I can about JavaScript and Node, React and Redux and all the different tools that come with that.

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