The Greatest Minds: Interview with Kent Healy #6


1# Filipa Canelas: Who is Kent Healy? And what did he do to be where he is?1# Kent Healy: This is such a complex question because people are complex. No one is easily or accurately summed up in a handful of words, but, here are some labels that would apply to me today: Entrepreneur, Dad, Husband, surfer, artist, writer, and autodidact. The latter has been a significant guiding theme in my life for the past 15 years. I love learning, but that wasn't always the case. After moving from Northern California (USA) to New Zealand, the transition created challenges academically. I struggled to get my footing and my teachers simply labeled me as a mediocre student. And worse, I accepted that label and performed accordingly. When I was 15, however, that changed. A couple of teachers encouraged me to try harder and study differently. The new belief that I could do and be better combined with a few new (but not revolutionary) studying techniques changed my life dramatically. My academic performed improved substantially. This gave thrust to my then, unrefined ambition, and self confidence. With my newfound confidence I simply approached things from a different perspective with grander expectations and although it sounds a bit cliché, this put me on a very different life path. Shortly after I started my first business with my brother at age 14, then started writing books and speaking, and now, I co-own a few real estate holding companies. 

2# Filipa Canelas: As a successful entrepreneur and writer, you need to come up with ideas. Do you face creativity problems? If so, how do you get new ideas and topics for your projects?2# Kent Healy: My creativity is usually the result of occasional inspiration or frustration, with the latter being most common. Many things I write about come as a result of recognizing flaws or inefficiencies in myself or the world around me. Being solution oriented, I then get inspired to address the issue. Challenges in being creative come as a result of one of the following things for me:1) Too exhausted. Not resting enough. Overcommitting, etc.2) Too many unrealistic expectations leading to attempt perfection, which of course it completely stifling. Frustratingly, this is not always something that is easy to recognize while it's happening.3) Unhappiness. Sometimes I find myself neck deep in commitments that are not a source of inspiration and feel more like obligations. I am getting better at avoiding these, but like anything, it's a learning process. And I should note that unhappiness is different to frustration. Whenever I get "stuck" it's usually because I am burned out due to over-committing and not resting. So, as a result, the solution for me is to avoid new commitments and clear my plate — often while also trying to fit some restorative activities into the mix (exercise, surfing, art, meditation, time with friends, etc.). All of this is much easier said than done, of course, but recognizing the problem is an important start. 

3# Filipa Canelas: How would your schedule look like, if tomorrow you had 100% of focus + 100% of energy + 100% of time (24 hours). Basically, what would you do on a perfect day?3# Kent Healy: Assuming this would apply to an average workday (non weekend) I would do the following: Wake up at 6:30am. Meditate and stretch. Eat a light meal. Make and drink a coffee while playing with my daughter. Address work related items that require deep focus. Surf. Go back to work (phone calls, emails, meetings). Eat lunch with a colleague or friend. Return to work for a short while. Create some art (painting, drawing, sculpture). Play with my daughter. Eat dinner with the family. Watch a documentary (or part of one) with a cold beer or glass or wine. Go to sleep. 

4# Filipa Canelas: I read your book “The Success Principle for Teens” and it became one of my favourite books ever. It was exactly the book I needed to start believing more in myself and in my own ideas. How would you sum up the whole book in one paragraph?4# Kent Healy: The book addresses the fundamental ingredients in what could be a called a recipe for success. The principles Jack (my co-author) and I selected are those we feel are imperative to laying a foundation for success — however one defines it. 

5# Filipa Canelas: I’m a huge fan of morning rituals, because they changed my life. Do you have any type of ritual to begin a new day? If so, please describe it.5# Kent Healy: I use software at work (and also use it in my personal life) to help me track my various, tasks, projects and goals so I have a good handle on what exactly needs to done when I wake up each morning. As a result, I often just hit the ground running to accomplish the day's goals. I've been blessed to develop a large degree of discipline that almost always helps me literally "plow" through fatigue, doubt, fear, etc. As a result, I don't feel it necessary to "ready" myself for the day. However, I do label this approach as one of the "day warrior." This start to the day does help me initiate and maintain a "get it done" mentality throughout the day, but sometimes that comes at a cost. I can become impatient and frustrated with people who aren't working at my same pace.  However, the "day warrior" approach is not always the most productive one.  As a result, my alternative start to the day includes 30-45mins that I intentionally do not check my phone. I will make a my morning shake and a coffee and try to be present. This can change the tone for the rest of the day which helps when I have stressful meetings or certain types of people to work with that I require me to soften my pace and style of communication. 

6# Filipa Canelas: What is the most precious advice you can give me if I want to write a book as a high-school student?6# Kent Healy: First and foremost, you need a topic that you are really passionate about. Writing for the sake of writing will make you better writer over time if hold yourself to high standards, but if you want to write a phenomenal book you will need a fire in the heart and mind — something you cannot stop thinking about and must put into words to quiet or relieve the mind. The second piece of advice would be routine. The more consistent you can be about your writing time and process, the more effective you will be. Be sure you block out set time in your calendar in advance. Never "wait" for space to "free up." Finally, what has always worked very well for me personally (when writing non-fiction, anyway), is outlining the structure of the book with chapters and subheadings and then write in bullet point form below each section. Writing in bullets gives yourself mental permission to simply extract thoughts from your head. Staring at blank pages and trying to fill them can be overwhelming. Writing bullets, on the other hand, seems more manager. In my experience, the bullets become longer and better quality over time as you continue to revisit and revise them. Then, the bullets develop in to stand alone ideas that organically grow in size and clarity. 

7# Filipa Canelas: What was the lowest point in your career/life and how did you overcome it?7# Kent Healy: My personal nadir struck in 2008, when the economy entered a tail spin. I had worked very hard for 4 years to make my business fun efficiently and profitably, but the market no longer offered the same degree of opportunity. Schools and businesses slashed their budgets for books and speakers and almost overnight. To add to the pain, I was extremely emotionally and physically exhausted at the time. For the years prior, I had prioritized work above all else and made a lot of personal sacrifices to get the business off the ground. As a result, changes in the economic climate was a hard and painful punch to the stomach. During this time I didn't leave my house for about 2 straight weeks. Quite literally, I didn't set foot outside. I never considered "giving up," "giving in" or "quitting" but I did need time to reflect and recharge. I emerged looking at business quite differently. During these 2 hermit weeks, I identified all the challenges of my business model and everything that needed to change so it was no longer such a draw of time and energy.  I did make difficult and brutal business changes in the following months, but the economy simply worsened. I realized my financial goals would never be accomplished within my existing business over the next few years. That's when I took the knowledge I had learned about business and recognizing opportunity and tried to identify a market "need" (rather than attempting to "force" my existing business onto a ailing market). The news headlines at the time continued to point to the real estate market crash. Knowing there is always opportunity during market crashes I brainstormed with my brother and Dad to figure out how we could enter the real estate market. That is a separate story in itself, but ultimately, the conversations that followed marked the beginning of my real estate career. My desire to make this opportunity work immediately demanded all of my attention. There was no reason, or time, to focus on the past. Wallowing in the past was simply not a productive option. 

8# Filipa Canelas: If you could only live by one principle what would that be? And why?8# Kent Healy: Constant improvement. As I wrote earlier in this interview, this principle is largely responsible for almost all the results I enjoy today. With a commitment to tirelessly improving oneself, all areas of life improve – not just for yourself, but for everyone around you. 

9# Filipa Canelas: What are you now working on?9# Kent Healy: I own and manage a couple of real estate holding companies with my brother and father and this keeps me plenty occupied.  In 2009 I put everything I had into my newly founded real estate company and took on every opportunity I could within that realm. We've experienced incredible and rapid growth, but once again, I find myself needing to slow down and recharge. I hope to pleasantly "pump the brakes" for several months as I think about what may lie ahead. I will always be involved in real estate because I appreciate the business model so much. I've developed a great knowledge/experience base in the space so it makes expansion more enjoyable. With that said, I would like to start a new professional chapter sometime in the next year or so. What that may be, I'm not certain. 

10# Filipa Canelas: Where can we stalk you, Kent Healy?10# Taylor Clark: Haha. I like how you stated that. It's best to connect on Facebook, Twitter, Instagram, and of course, my blog. 

Quick Questions: 

The Last Book you Read:Frankly, it's been a long time. I don't recall. I do, however, constantly listen to audio books and podcasts where exceptional people are interviewed. I do this mainly as I drive or exercise. I also watch a lot of documentaries.

Dream Job when you were a Kid:Astronaut. Indiana Jones type explorer. Batman.

Favourite Quote:These are two of my own creation that constantly remind myself of... 

  1. Perception is the problem. And the opportunity. (more here:
  2. The first rule of any game is to know you are in one. (more here:

25$ life-changing item:A set of Bodum double walled glass cups. When I make coffee each morning they look great and keep my coffee warm. They also keep my beer cold and don't sweat/leave water marks/rings on my tables. (

Favourite place to work:In my office. I have all the resources I need there within an arm's reach. I am able to be far more productive there than anywhere else. I used to enjoy working from bizarre locales and combining work with pleasure. But these days, I like to intensely focus on work when I work. The goal is to be as productive as possible during work hours and then leave the work behind when I exit the office.