Diana Goodwin is an entrepreneur, speaker, and startup advisor. She is the founder and strategic advisor at AquaMobile Inc. and the founder and CEO of MarketBox. Goodwin is considered a tech innovator and thought-leader in marketplace businesses, the gig economy, and scaling businesses internationally and can regularly be seen speaking at events, sharing her knowledge with both corporate and entrepreneurial audiences.

Where did you grow up and what was your childhood like? Did you have any particular experiences/stories that shaped your adult life?

I grew up in Mississauga, a suburb of Toronto, Canada. I was given a lot of freedom to pursue what I wanted. Whether it was soccer, swimming, or wanting to start my own newspaper, I was given a lot of room to explore and figure out what I was most passionate about. I was never pressured down a certain path or into one activity over another. As a kid, I was always trying to start new businesses—I loved to do that! And luckily my parents were good-natured about it. 

What is something you wish you would’ve realized earlier in your life?

That I don’t need to run myself ragged to succeed. I used to think that I had to constantly be doing something or else I was slacking. I’ve come to realize that it’s all about focusing on the critical tasks that will move the needle the most. It doesn’t have to be hard. 

What are bad recommendations you hear in your profession or area of expertise?

One of the worst recommendations I hear in my industry is to build custom software right away. 

If technology is not core to your business, this is a bad idea. I recommend the opposite: Launch something low-tech first, so that you can launch quickly and test to see if there is actually a market for your product or service. And, ideally, start generating money as well. 

I’ve seen too many founders sink their money into technology upfront, only to realize they got it all wrong and the concept doesn’t resonate with their users—or they don’t have any money left to actually market and sell the product. 

Tell me about one of the darker periods you’ve experienced in life. How you came out of it and what you learned from it?

A few years ago, things were moving along fine with my first business, AquaMobile, but I wasn’t feeling fulfilled the way I had been in the early days. When other entrepreneurs started asking me to spin out the AquaMobile software, I got excited again as I realized that my passion is helping entrepreneurs build businesses. Using the AquaMobile platform as a starting point, I created a new company called MarketBox, a sales and scheduling e-commerce platform designed to boost sales for service businesses with mobile and virtual workforces. 

Now, I get to help other service businesses—including mobile beauty salons, fitness studios, tutoring services, and pet groomers—grow with the help of my expertise. I’m grateful that, through MarketBox, I get to share my knowledge with other entrepreneurs.

What is one thing that you do that you feel has been the biggest contributor to your success so far?

Having grit. Not giving up when times get tough, knowing that they will get better.

What is your morning routine?

I get up around 7 or 7:30 a.m. I typically don’t use an alarm clock so it varies. First thing, I get up and drink a liter of water. Then I’ll do some tai chi or chi gong and do some meditation and visualizations, grounding myself and starting the day on a positive note.

What habit or behavior that you have pursued for a few years has most improved your life?

My morning routine! Hands down.

What are your strategies for being productive and using your time most efficiently?

I usually set aside a couple of hours in the morning to do deep work without meetings or interruptions—anything that requires more brainpower. I typically schedule meetings and more transactional activities later on in the day. 

I’m a big fan of the Pomodoro technique and use an app called Forest to track my time blocks.

What book(s) have influenced your life the most? Why?

The 4-Hour Workweek by Tim Ferriss

Tim Ferriss’ book was my playbook when I was first becoming a full-time entrepreneur. A lot of the principles are still applicable today.

Autobiography of a Yogi by Paramahansa Yogananda

Yogananda’s book was gifted to me by a friend. It really opened my eyes and played a part in me exploring my spiritual side more deeply. 

Do you have any quotes you live by or think of often?

“Do or do not, there is no try.” – Yoda

This reminds me to just go for it, do something wholeheartedly, and not make any excuses for failure.