This Entrepreneur Shares the Most Important Factor of His Success

It's all about staying healthy -- mentally and physically.
This Entrepreneur Shares the Most Important Factor of His Success
Image credit: Courtesy of Harper Reed
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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.

A perennial question for businesses is how to find customers on the platforms they love to use. It seems like there is no one right way to crack the ecommerce code and become a hit -- but back in 2013, Harper Reed thought his idea could make a difference for up and coming businesses.

Reed’s first project about being the chief technology officer of President Barack Obama's second presidential campaign, was to create Modest, a platform designed to make mobile transactions simpler for online retailers.

His goal was to help any company, no matter the size, seek out new customers and sell its products anywhere. “We wanted to give retailers access to compete,” explained Reed.

Related: How to Make at Least $1,000 Your First Month of Ecommerce

The Chicago-based company officially launched February of 2015, and after a year in beta was bought by Paypal seven months later.

In 2015, Reed became PayPal’s company’s senior director of software development, and the head of commerce at Braintree, a subsidiary of Paypal that focuses on mobile payments.

Modest is now called PayPal Commerce, and it relaunched under that name in early 2016. The platform allows businesses to embed buy buttons anywhere online they want their products to be purchased -- from social media to apps and email promotions.

We caught up with Reed and asked him 20 questions to figure out what makes him tick.

1. How do you start your day?
I try and wake up relatively early. I listen to some music, and check Twitter. I also make sure I weigh myself and check how long I slept. I do that because knowing that data seems better than not knowing it. That's been my routine for the last five years. I also try and get to the gym in the morning a few times a week because I think it sets a good tone for the day. I started working out because it makes my mind clearer during the the day.

My approach to everything is iterative. Because I started programming at such a young age, when I think about behavioral changes, I think why did I do this in the order I did it? Why do I think this helps me be high performance? I constantly am in the process of saying that didn't work, what would make this better? I don’t always have standard routine. I’m constantly reevaluating if this [routine] is going to get me through the day and inspire me.

2. How do you end your day?
The main thing I try to do is have dinner with my partner -- that's a really important thing to me. I also love to read, I find that the end of the day, it is a good cool down exercise is to read a book.

Recently I’ve been reading Catch-22 by Joseph Heller. It’s a long book and is very funny. It talks a lot about government, and I found reading it to be a cathartic experience.

I was reading non-fiction books, but I found it wasn’t helping me to be rested. I needed to read something that helped me go into a lower gear, and that book has done a good deal of that.

3. What’s a book that changed your mind and why?
I recently read a biography of Elon Musk: Tesla, SpaceX, and the Quest for a Fantastic Future by Ashlee Vance. It didn't necessarily change my mind, but it shifted me to be a very strong admirer of his drive, power and what he has been able to achieve. It's amazing to watch Tesla and SpaceX and understand a little more about the path to it was really great.

4. What’s a book you always recommend and why?
One of them is The Girl in the Road by Monica Byrne. It's very intense and bizarre. I really like speculative science fiction, and the book is close enough to now to have some reality to it -- it's about environmental disasters. It talked about a future that i think is inevitable, the world ending as we know it.

The person who recommended the book to me is someone who is constantly pushing me and challenging me to think differently. And it isn’t written by a white man. I try to make sure the perspectives I’m reading are not coming from people like myself. It represents something that is drastically different.

5. What’s a strategy to keep focused?
I find that if I spend time in a gym, then the time after that, I am much more focused.

If I get a lot of sleep and read to decompress, I'm able to focus more. It's a lot about self care, because if you're worried or frustrated, it's going to be hard for you to focus on things around you.

I don't drink coffee; I drink a lot of green tea and water.

Related: 3 Simple Ways to Sharpen Your Mental Focus

6. When you were a kid what did you want to be when you grew up?
An astronaut. I still want to, in a way, it’s just so cool.

But I started programming when I was 5 or 6. My career choice has largely been what I wanted to do. I always knew that technology would be one of the threads. That I find myself here is not really a surprise, which is good and bad. It's good in that I'm able to do what I love, and it's bad in that this is not a story that everyone gets.

7. What did you learn from the worst boss you ever had?
I've had a lot of bosses that I didn't agree with, but the worst boss was very much my myself. So, I can't let myself slack off and if I do slacking off, I'm the one that's yelling at myself. I've worked with a lot of different employers, and none of them have been as aggressive as I have been.

When you’re part of a big organization like PayPal it’s kind of like the ocean. It moves and shifts and you work with a lot of people. When I think about what I would do differently with my own leadership style is a constant need to fight the last battle we had, instead of thinking about the future. I have to be careful that if I do start a new project, I need to not react to old concerns.

8. Who has influenced you most when it comes to how you approach your work?
I don't know that I have one person I feel has really influenced me, but I try to glean from as much people as I can. In every experience you get an opportunity to learn about what you would and wouldn't do.

Working with so many smart people on the Obama campaign was an opportunity to glean a lot of things. All the leaders I worked under were amazing leaders. Regardless of whether I agreed with them, we were able to work together.

9. What’s a trip that changed you?
A couple of years ago I went to Johannesburg, South Africa. Living in Chicago, we live in a city that's aggressively segregated, and with that trip it was like seeing the logical conclusion of that systematic segregation of Apartheid.

Even though we're some years removed and there is healing and we’re starting to see the first South Africans born not under Apartheid, still seeing the pain and destruction of that society really opened my eyes and made me think about what happens if we don't fix our inequality issues in the US? How do we solve those problems?

It showed me a future image of Chicago. I worry about the United States with its history of how we treated people of color. I can’t help but imagine a similar reaction to what we saw happening in Johannesburg.

My hobby is trying to make the world a better place. How can I participate in preventing this future vision I see. How can I make a world that is more equal? I want to help Chicago. I think about this experience every day. We need education, community building resources and creating opportunities for people no matter where you’re from.

10. What inspires you?
The democratization of access, of giving people opportunities. One of the main reasons I was so excited when we sold our company to PayPal is because PayPal has been doing this for a while: giving people access to things only large companies with resources and wealth are able to accomplish.

Hearing our CEO speak about these things is really inspirational, because he really believes that this is a huge part of PayPal.

Related: Inspiration From 7 Legendary Business Titans

11. What was your first business idea and what did you do with it?
I was one of the few people with a computer at a very young age, so I sold, actually sold is probably a strong word, really just traded for candy, a lot of shareware. I downloaded software onto disks, had a small library and people could buy the disks.

12. What was an early job that taught you something important or useful?
My father was a property manager and we would often be on the crew doing the worst work -- picking up in yards, maintenance, sometimes the crew was the one that did evictions.

[The evictions] could be for any reason. You know, they could be bad actors or causing problems. Or they could have just lost their jobs and things got hard. That was a good lesson for me. You don't know when things are going to get rough, so protect yourself and others. Try your best and your hardest and hope that everything works out, because nothing is guaranteed.

13. What’s the best advice you ever took?
Manage politics by your outbox. Look at your outbox and see who you are emailing. [Usually] who you are emailing is related to who is supporting you. If you're not emailing people, then they are probably not supporting you.

14. What's the worst piece of advice you ever got?
If someone gives me bad advice I try to immediately forget it. I think advice is like assholes, everyone's got one. I try really hard not to give advice. When someone asks me for advice, I just talk about my own experiences.

I think advice often isn't real; it’s a little bit fake. We just need to be careful to say that advice is this important thing. I try really hard not to give advice. When someone asks me for advice, I just talk about my own experiences.

Experience is the most important thing. I like reading about history because you can learn from these experiences. I don't think you can actually learn from advice.

15. What’s a productivity tip you swear by?
There is an app called SaneBox  that helps me manage my email, and it's awesome. It's machine learning, and it works really well.

Related: 4 Tips to Better Manage Your Email Inbox

16. Is there an app or tool you use in a surprising way to get things done or stay on track?
My favorite app in the world is email. Right now I'm using Google Inbox. I think Microsoft's Outlook is very good. Obviously my phone is everything. Having that charged up and working is positive.

17. What does work-life balance mean to you?
There are a few things I have to do. I need to make sure I have dinner with my partner so we can connect and have some kind of non-work context to just ground yourself.

The second thing is I turn off my notifications at 11:30 pm. We’re so addicted to notifications.

It is about health. Often,  we look at jobs as things we just go to, but we don't realize how important our personal health is to our success. If we're not healthy, then it just doesn't matter. You're not going to do good, you're not going to be happy.

18. How do you prevent burnout?
Stay healthy. Being aware of your surroundings and really participating in self-care. What are the things that you need? Being able to express those needs is so important. That is hard; I'm not always good at it. Part of not having burnout is being self aware.

19. When you’re faced with a creativity block, what’s your strategy to get innovating?
I usually just play Minecraft.

20. What are you learning now?
I just bought a house, and I've been learning how to interact with the different ways people work, and comparing my own experiences in tech with someone who works as a contractor.

Working with these folks and learning how they work has been really interesting. I have been thinking about how I can apply it to what I do, or how can technology help them with their work?

Interview was edited for clarity and brevity.

Edition: May 2017

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