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This Successful Entrepreneur Explains Why You Shouldn't Put Time Limits on Creativity The League founder and CEO Amanda Bradford shares how prevents feeling creatively blocked.

By Nina Zipkin

Courtesy of Amanda Bradford

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.

If you're single, there are so many apps out there purporting to help you find if not a relationship, at least a date. But with so many options, it can lead to burnout. Or the feeling that with an endless string of people to swipe on, why choose anyone at all?

It's something of an imperfect system, and a problem that The League founder Amanda Bradford is excited to jump in and solve. "I want to be the company that fixes dating in the same way Google fixed search," Bradford told Entrepreneur.

Bradford comes at the dating game from the tech-focused background. She studied information systems at Carnegie Mellon and got her business degree from Stanford. Before launching The League in 2015, she worked in technical roles at Salesforce and Google.

She wanted to start the company because of the elements of the online scene that bothered her most: a lack of privacy and filters, and only being able to judge a person based on a photo alone. She was also put off by the fact that she could be matched with a colleague if they happened to come across her profile, leading to potentially awkward scenarios at work.

She was sure that other career-minded single folks felt the same, so she set about creating a platform that utilizing Facebook and LinkedIn would provide your background to potential matches upfront while making sure your work and social life stayed separate.

Today, the company has raised nearly $2.3 million in funding and operates in 20 cities, 12 of which launched just this year. There are now more than 100,000 people on the waitlist.

We caught up with Bradford to ask her 20 questions and find out what makes her tick.

Related: This Founder Shares Why In Order To Learn Fast, You Need to Fail Fast

1. How do you start your day?
I'm a night owl, so I go to bed pretty late, which means I start my day when the sun shines through my skylight. After showering, I check emails and do some reading on things happening in tech, the dating industry more specifically, as well as the news. I then look at my list of to-dos, so I can decide what I'm going to work on that day.

2. How do you end your day?
I like to end my day reading about business strategy so I get some good ideas as I nod off to sleep.

3. What's a book that changed your mind and why?
The Feminine Mystique by Betty Friedan. Reading such a legendary, iconic book over 55 years later made me appreciate just how far women have come in such a short time in gaining equality in the workplace. Though it's also disheartening to see how little things have really changed at the same time. The book caused me to question why that progress hasn't made it's way into household relationships at the same rapid pace and helped me reframe our mission statement.

What I want is to help move society towards redefining dating and letting go of antiquated gender stereotypes. To me, equalism is not forcing women to message first or to be "in control'. It is encouraging our users to seek intellectual equals and give them a platform that facilitates connecting based on more than just looks and attraction.

4. What's a book you always recommend and why?
Steve Jobs by Walter Isaacson. Steve Jobs was famous for charting his own course rather than the status quo directing him. Everyone told me that the dating space was crowded and that no one would invest in a solo founder. I think women CEO's have the responsibility to be as visible as they can to society at large, while still running their company effectively as a CEO should.

That means our job is twice as hard, but it's twice as important. Our society sorely lacks women role models in high-ranking positions and it's our responsibility to make sure society's youth has ample role models to look up to in all industries and professions and this concept of "girl job' and "boy job' is completely eradicated. "Getting out there" and reminding people that they can do or be anything if they put in enough blood sweat and tears is a top priority of mine.

5. What's a strategy to keep focused?
If I'm trying to "get in the zone", I put white noise on and turn off Slack and only check email once an hour. Ideally, I am isolated where I can't be distracted, [as I can be] easily distracted.

Related: This Successful Entrepreneur Explains Why Revenue Is Not the Most Important Thing (and What Is)

6. When you were a kid what did you want to be when you grew up?
I wanted to be an FBI agent with a computer science degree. I was inspired from Lucy from the Kay Scarpetta series by Patricia Cornwell, which I read religiously growing up.

7. What did you learn from the worst boss you ever had?
The worst boss I had was never around nor gave me feedback, so I learned how to self-manage and self-grade my own work. Looking at your own work from an objective eye is difficult and learning how to rely on tools [you find yourself], rather than other people helped me when starting The League.

8. Who has influenced you most when it comes to how you approach your work?
My mom. Not only does she have good ideas, she figures out what needs to be done and then does all the execution work needed to take her idea across the finish line. She is constantly learning, and I've never once heard her say, "I don't know how to do that."

9. What's a trip that changed you?
I graduated college a semester early and travelled alone to Australia, New Zealand and Fiji. I had to figure everything out on my own once I got over there, and I also met hundreds of other backpackers from all over the world. I learned that I love meeting and hanging out with people [who are] different from myself, and I also learned that I love independence and the autonomy of being able to make my own decisions about where to go and what to do. I believe this trip gave me the confidence I needed to start my own company later in life, without co-founders.

10. What inspires you?
Fixing the problem. We're making great progress at making online dating better, but I want to be the company that fixes dating in the same way Google fixed search. The process is broken and we have an amazing team that is behind us in our vision.

I also want to fix the lack of role models problem. I want The League to succeed at great scale, so we can serve as real-life-versions of the role models that I could only find through fiction books growing up. I want the people who work for The League and the highly ambitious users we match to serve as an inspiration for my nieces and for girls out there who may not have a role model directly within their small communities.

Related: The Entrepreneur Behind a $90 Million Company Shares How You Can Get Past the Naysayers to Build a Successful Business

11. What was your first business idea and what did you do with it?
I learned to make very complex, beautiful friendship bracelets in third grade and sold them for $5 and $10 each. My second business idea was selling mixed CDs with my own custom covers that I sold for $10.

12. What was an early job that taught you something important or useful?
My first job out of college was a sales engineer, meaning most of my job was how well you did your presentation. I spent days on end customizing the demo down to the last pixel on the dashboard, so the data looked superbly customized for the client, and the product would practically pitch itself, but I didn't spend any time on practicing what I would say in my demo. The result was I absolutely bombed my first pitch. My words were scrambled, I was stuttering and nothing that came out of my mouth could be called eloquent or persuasive in terms of why the client should buy our software.

I got the lowest score out of five of us on the team for my presentation. I was shocked because a few others on my team didn't practice much either, but their pitches sounded great and natural. It was the first time I realized that people have different strengths and weaknesses, and even though I was putting two to three times the effort into building out the product demo, they were performing higher because they were just better at pitching than me.

I'm wildly competitive, so it was a huge shock to my system not to be a top performer on my team. I learned life is not fair, and I started practicing eight to ten hours for each demo I would give. While it didn't happen overnight, my pitching skills improved drastically, and I was finally able to be on the same level as the guy who was "naturally good at pitching". Lesson learned: do the work.

13. What's the best advice you ever took?
Raise more money than you think you need. If it's there, and you're a first-time entrepreneur, take it. You will spend it, I promise.

14. What's the worst piece of advice you ever got?
Worrying about getting advisors. I think the whole advisor concept is a bit silly. Either you want to invest in the company, or you want to do a job and get paid for it in salary, plus equity. I think the advisor model is not clear enough on what the arrangement is and the way it is [constructed]. It just asks for miscommunication and disappointment.

15. What's a productivity tip you swear by?
It only takes one minute, but it helps us find information much much more easily. I re-label the subject lines of important emails with their distinguishing keywords and re-send them out, so I can search for them in my email. I also create a google doc with the same title and the content. That way, no matter where someone is looking, it should be in their email or drive.

Related: Stitch Fix Founder Explains Why the Worst Piece of Advice She Ever Got Was to Raise A Lot of Money

16. Is there an app or tool you use in a surprising way to get things done or stay on track?
We live and breathe by our Periscope dashboards here. They are sent to us daily and remind us the company's biggest priorities.

17. What does work-life balance mean to you?
Right now, given how fast we are moving and hiring, it just means me having two to three nights a week of more than three hours of downtime where I can think, strategize and relax.

18. How do you prevent burnout?
We launched in 12 cities this summer, and I was working at every single event, so I have some experience with this. When I start to feel burnout, to me that means I haven't spent enough time reflecting on all we've accomplished, and I haven't let myself take a step back and feel proud of the product, community, and team I've built.

Most of my coping tactics involve me taking some time away by myself -- even if it's just a day off here and there -- to unplug and get away, so I can reflect on everything that has gone well and give myself a pat on the back and really, really sit and appreciate all the hard work my team has put in to build this company. If you aren't doing that regularly, you will feel burned out, as there is always so much more ahead of you to get done. It can get overwhelming if you don't also look back at how far you've already come.

19. When you're faced with a creativity block, what's your strategy to get innovating?
For me, it's giving myself enough downtime to first find inspiration online and reading different opinions or techniques on whatever I'm trying to be creative about, and then giving myself time to create. I hate having time limits on creativity. I try to carve out, at minimum, a full day I can dedicate to a creative project.

I don't end up using all of the time, but having it blocked out and knowing this weekend is dedicated to completing X helps pump me up like it's a big game day or something like that. I try to get sleep the night before so I can do a full creative day and get the project 90 percent there in one sitting. That's my favorite way to work on creative things -- getting in the zone!

20. What are you learning now?
My biggest new learning has been in recruiting -- learning how to recruit and hire a senior leadership team for the business. The team we build will be what determines the future success of the company, so learning how to build, manage and retain a world-class leadership team is one of the most important skills a CEO can learn.

Related video: Mona Patel Had to Fight Her Heritage to Become a Successful Entrepreneur: What You Can Learn From Her Story and Courage

Nina Zipkin

Entrepreneur Staff

Staff Writer. Covers leadership, media, technology and culture.

Nina Zipkin is a staff writer at She frequently covers leadership, media, tech, startups, culture and workplace trends.

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