John Holloway

Stay Uncomfortable. Always work towards a goal. Never cruise. The second you sit back and relax is when you begin to lose progress.


John Holloway is an entrepreneur and digital marketer with over 10 years of experience as a small business owner. He got started in 2008 while still in college. He launched a web publishing company in the gaming space, and quickly grew the traffic via search engine optimization. His network of sites was eventually acquired in 2011, paving the way for more ambitious projects.

In 2011 he founded an e-commerce business in the motorsports industry. He grew a large Facebook following of over 3 million subscribers. Through social media and organic search he was able to grow revenues year over year and was acquired in August of 2013. was launched in September of 2013 as a way for people to buy life insurance online without having to take the medical exam. Since launching NoExam, it has helped over 10,000 customers get life insurance.

Where did the idea for your company come from?

My friend was a life insurance agent, and he was complaining about how old school the entire industry was. He had mentioned there were a few products that were going online, and we decided to build a business around selling policies that didn’t require the medical exam.

What does your typical day look like and how do you make it productive?

The typical day starts at around 7:30am. I’m up early communicating with our web developers. After that it’s onto keyword research and content marketing to help grow our search traffic. This takes up most of my day. Some days there are new pages to publish or meetings but for the most part it is a pretty low key schedule. Mid day I’ll take a break and go to Jiu Jitsu or do some trail running. Afternoons are for tying up any loose ends for the day or to publish any new content that has finished the editing process.

How do you bring ideas to life?

Everything starts on a pad and paper. From there it usually makes it onto a Trello board. Depending on the idea, it will be shared with either a designer, developer, or writer.

What’s one trend that excites you?

Acquisitions in the insuretech industry. Large publishers seem to be buying up companies at great multiples. You never know!

What is one habit of yours that makes you more productive as an entrepreneur?

Waking up early. The 2 hours of work before anyone else is online is the most productive parts of the day. Very little interruption.

What advice would you give your younger self?

Save that money! You’re not special. Anything to curb that ego I had in my early 20’s when first experiencing success as an entrepreneur.

Tell us something that’s true that almost nobody agrees with you on.

Mountain bikes are better without gears and shifters.

As an entrepreneur, what is the one thing you do over and over and recommend everyone else do?

Get out of your comfort zone. Comfort means you are not moving forward. Business is competitive and if you are comfortable it means you aren’t in the fight. You are getting left behind if you are comfortable.

What is one strategy that has helped you grow your business?

Doing the same thing everyday for months and expecting nothing in return. Many entrepreneurs give up before they get over the hump. The hump is the grind that you have to conquer before you can stat seeing results. You have to put in the work and be willing to do it for nothing at times. Being an entrepreneur is all about delayed gratification. Win or learn.

What is one failure you had as an entrepreneur, and how did you overcome it?

I over extended myself on my ecommerce business. Way too much inventory and not enough sales to justify it. Luckily the business and inventory was acquired otherwise I’d sitting on 1000 motorcycle helmets. Lesson learned, tread lightly into unknown waters and always have an exit strategy.

What is one business idea that you’re willing to give away to our readers?

Social media coaching. Coach people on how to present their ideal image of themselves via various social media platform. Influencer marketing is big right now. Give them advice on how often, what types of posts, how many product posts, and overall image that companies want to see for their products. Seems like a hot market with lots of people looking for that magic bullet.

What is the best $100 you recently spent? What and why?

For me it’s Ahrefs. It’s an seo tool that helps me every day to figure out what topics to write about. It helps me keep an eye on what competitors are doing as well. I spend a lot of time looking at reports in Ahrefs.

What is one piece of software or a web service that helps you be productive?

Trello. I use it to manage all the different projects at home and at work. I use the agile workflow and just move things to the next column. There is always something to do in my Trello boards.

What is the one book that you recommend our community should read and why?

Rework by Jason Fried. It presents a different way of thinking about work. You don’t have to do things the old fashioned way, you can do them your way.

What is your favorite quote?

Discipline Equals Freedom – Jocko Willink.

Can be applied to many things in life, but mostly it equates to time management for me. Have the discipline to wake up early and you’ll have the freedom to go on a run in the afternoon. Have the discipline to not spend your money on material possessions and you’ll have the financial freedom to retire early. That’s the general idea.

Key Learnings:

  • Wake up early – Try to get several hours of completely uninterrupted work in first thing in the morning. Usually you can almost cram a whole days work into two hours.
  • Be humble – You aren’t special. You can always get better or learn more. Check your ego. You’ll up your game when you realize you have more to learn.
  • Stay Uncomfortable – Always work towards a goal. Never cruise. The second you sit back and relax is when you begin to lose progress.