John Hall – CEO of Calendar

John Hall is Co-founder of Calendar, a time management tool that helps users align their schedule with their values. A popular motivational speaker, Hall authored “Top of Mind,” a leadership and marketing book about differentiating one’s brand through helpfulness.

Where did the idea for Calendar come from?

My initial plan for Calendar was a thoughtfulness CRM. Basically, I wanted to create a tool to help people devote their time to the relationships that matter most to them. 

With my idea in mind, I called up Calendar’s other co-founder, who already had a vision for what the calendar could be. As we talked about it, we realized we had a chance to improve people’s lives by evolving the calendar for the modern world.

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

To get my adrenaline pumping, I work out first thing each morning. After dropping the kids off at school, I immediately jump into work. I rarely take breaks, so I really don’t stop until the end of the workday. Once I get into a rhythm, I stick with it in order to get as much done as possible.

How do you bring ideas to life?

I don’t bring ideas to life; my team does. I might generate the spark, but ideas come to life through execution and iteration.

What’s one trend that excites you?

As our days become busier, we’re valuing our time more highly. Everyday people are turning to time management techniques that were once practiced largely by the c-suite.

I don’t see that trend ending any time soon. In fact, we’re excited to be furthering it with new tools and data.

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

My speaking career helps me endlessly as an entrepreneur. After a few gigs, I started to show up on lists for sales speakers and guest speakers. Those mentions helped me secure more opportunities, which got me in front of more people.

Don’t underestimate the value of building trust directly with people. It’s an investment in your personal brand as well as your company: Many listeners later check out the companies I’m involved in, and some of them even sign on as clients.

What advice would you give to your younger self?

Build your personal brand, as I mentioned earlier. Speaking may not be for you, but it’s not the only option: Educate yourself, create content, and use online media to get your ideas out there. Personal branding can bring more opportunities to your career than you might think.

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

“The Bachelor” is one of the best shows on television for entrepreneurs. I love it: My wife and I grab a glass of wine, tune in, and forget all about the business world. When my mind is running 100 miles per hour after work, I need to watch something ridiculous in order to wind down.

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

Surround yourself with good people. What’s the point of the ride of entrepreneurship if you can’t share it with others?

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

I’m biased, but it works: At every company I’ve led, I invest in content strategy. I’ve found that creating great content (and publishing it in the right places) is key to building trust, getting top talent, and closing sales.

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

As a young entrepreneur, I made deals with people whose values weren’t my own. Now, I simply don’t work with those sort of people.

The great thing about entrepreneurship is that you get to choose who you do business with. I’ve deliberately surrounded myself with people who I trust and respect, and it’s made all the difference.

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

I’d like to see someone set up a site with one-page profiles that describe how others can help the user out. I’m always trying to find ways to help others. When that help is unsolicited, it’s not always obvious what I can do. I wish everyone could know exactly how to lend a hand to their friends.

What is the best $100 you recently spent?

I bought mixmax subscription for helping me with email communication. Love it! I always get behind on email and this has helped.

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

I use Appointment, a company I’ve invested in, to streamline billing and scheduling for a few of my other companies.

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

I can’t pick one; my two favorites are “Mean People Suck” and “You Don’t Have To Be Ruthless to Win.” 

Michael Brenner’s “Mean People Suck” is a cheeky, fun read about how compassion and empathy are more effective leadership tools than blame or anger. “You Don’t Have To Be Ruthless to Win,” written by Jonathan Keyser, is about self-service and truly helping people without any expectations back.

What is your favorite quote?

“You are the average of the five people you spend the most time with.” — Jim Rohn

Key Learnings:

  • Rather than take long breaks, embrace your flow state to get more done at work.
  • To elevate your career, build your personal brand via speaking opportunities and content.
  • Do business with people whose values align with your own. You’ll be happier and more successful.