Kristin Cripps

Follow your dreams. Look at what you want in life, why do you want it? Start planning the steps of what you need to make it come to fruition.


Kristin Cripps moved out at the age of 16 and was making $635 a month at a grocery store and naively thought that would be enough to live off with rent of $530, plus utilities and food. She quickly learned differently. Luckily, she had a quick turn around with learning how to bartend. She was able to leave that apartment and its cockroaches, and a friend informed her that her rent in Toronto was more than her mortgage in a small town not too far away. After that, she purchased her 1st home at 19.

When she wanted to rent out that home and move to her next purchase, however, she was told by everyone under the sun not to do it, and every horror renter story one could think of, so she sold it. It later re-sold, and the next owner made a good chunk of change off it. She mentioned it to someone who had told her to sell it and he said, “Why didn’t you keep it as a rental?” That is when she decided to stop listening to other people and do her own thing. She began investing in rental properties and doing flips and quickly turned her counting quarters bartending job into a multi-million real estate operation.

Now transitioning into events, online courses, and speaking engagements. She is also in the middle of writing two books with a third idea simmering on the back burner. Through the funds she has acquired from real estate investing, she wants to show everyone how they too can live their dreams now and not wait until they’re retired to have the extra income. She’s had nightmare tenants, blown off ceilings in renovations, gutted homes, built homes from scratch, owed over $900,000 in back taxes and bills and turned it all into a thriving empire, and now she wants to teach you so you don’t make the same mistakes.

Where did the idea for your career come from?

I had been in real estate for well over a decade and found myself at a conference in Bali when a gentleman was asking me how I had accumulated so many properties and wealth, and I told him the short of it over dinner. He said, “That needs to be a course so more people can copy you,” and hence the first seed was planted. I also had been throwing parties for clients for years. These started out once a year at my home and quickly grew to 400-600 people, multiple times every year. So fittingly my next venture was doing events for not only my clients but other people. I also figured because I love to travel, doing speaking engagements would be a fun way to tell more people across the globe about how they too could live the life of their dreams. I love motivating others and showing them if I can do it, anyone can!

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

Regardless of what country I’m in I always start with something motivational on Youtube while I do a quick exercise routine. I also like to write in my gratitude journal, where I write everything as if it is now (but yet it is future). Then after that, it’s quite varied depending on where I am located in the world. Perhaps I’m off gallivanting in another country taking in the sites, having a massage or shopping. I might be working on a new project, off to a staff meeting at my real estate brokerage or headed to a job site to talk design with my builders, go over plans, changes or additions. Often at night I will read or review my goals, listen to some Spanish tunes and dance up a storm or tackle something I have been putting off (or of course there is always sushi).

How do you bring ideas to life?

I always have a ton of journals and notebooks going. I jot down ideas and if I don’t feel I’m the most knowledgeable in a certain area I will look up someone who is to help and collaborate with. I hate settling and am always trying to better myself, my businesses and relationships with those around me. If you’re not growing, you’re dying so why not live the most abundant life possible?!

What’s one trend that excites you?

I would say personal development. We are blessed to live in such a time when there is so much valuable information at our fingertips and how that is propelling the human race forward. I love that people are trying to be healthier, quitting the jobs they hate, going after their dreams, solving environmental issues, working together to create more peace, delving into cures and solutions for disease and prevention, banding together to help as many as they can, abolishing old rules and regulations that are not serving us or animals. It is incredible.

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

To never be stagnant. Keep expanding, keep growing, keep learning. Whether people chose to do so via YouTube, books, podcasts, attending seminars, etc. whatever best suits their learning style. Never stop growing your mind, and your body. Your soul will thank you.

What advice would you give your younger self?

If you are always thinking that people will screw you over or that you are the only one that can do it best, you will end up with people deceiving you and you will be exhausted and burn out. From not taking anyone else’s help or always being on guard you will never fully live in the moment. Life is not so hard, don’t make it so. Enjoy every day and let go of all your stories! That is all they are, not your daily truth.

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

It just takes baby steps to get to anything massive. I suppose I say that because I feel like many people just don’t do. People complain about multitudes of things, but they go home after work and binge on Netflix, Facebook or Instagram and don’t take the baby steps required to propel their lives towards something bigger or healthier for them.

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

Get up when you fall. It is guaranteed that there are always going to be things that don’t go your way, but the key is to never give up. Learn from it and keep trucking forward. Do you want to live your life on the sidelines or on the field? Get in the game and play your heart out!

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

Systems and coaches. Okay, that’s two but I never claimed to follow instructions well. Systems to make sure everyone gets the same superior service and coaches to point you in the right direction when you may not possibly see it or to advise you of other capable humans when you need advice, guidance or growth. Hard stop.

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

I have had more than one, and I think any true entrepreneur or business owner would tell you the same. I had a spa once which was costing me more every month in advertising, wages, products and so forth then it was bringing in. I assessed the in’s and out’s and realized my heart wasn’t in it, there was no passion. Even if it made me rich, I wouldn’t have been happy, so the doors closed forever. What is yours, why? What makes you tick? If you made no money at your current job would you still do it for the love of it? If not, what job would you do for free?

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

Follow your dreams. Look at what you want in life, why do you want it? Start planning the steps of what you need to make it come to fruition. You are the only person that sets the bar for yourself so make sure you set it high and keep re-adjusting as you attain each milestone!

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

My internet bill. There is just so much knowledge online. I also buy a lot of books. I try my best to listen to motivational and inspirational people and keep any negative, self-doubt talk, or drama clear from my space.

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

It sounds dumb but I’d say either my YouTube app or Spotify. Youtube fills my mind with growth and rewires it because I get to choose what I put into it and Spotify lifts me up and keeps me on my dancing toes.

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

I just read Disrupter

By: Miki Agrawal

She kicks ass. I love anyone who goes after their dreams. But when they can do it with such humility and give back the way she does and just be so genuine it is truly admirable (that is a huge run-on sentence but get over it lol).

What is your favorite quote?

“I am in love with people I have never met and places I have never been”
– Unknown

Key Learnings:

  • That they can do anything they put their mind to.
  • Don’t let anyone tell you that’s a dumb idea or that will never work.
  • Don’t live in the past.
  • Invest in real estate as soon as possible, don’t wait 10 years or for the perfect house, do it now!