Justin Donald; The Lifestyle Investor

Steve D Sims
3 min readOct 6, 2021


Are you currently living your dream lifestyle?

We only get one life. But, unfortunately, many of us choose to live it on autopilot.

Instead of planning our life, we let circumstances, careers, or our business make our lifestyle decisions for us.

Justin Donald is a different kind of financial planner.

Rather than looking at the dream lifestyle you’d like to have in 10, 20, or even 30 years from now, he asks different questions, like:

  • Imagine your dream lifestyle. What does it look like?
  • What would you need to start living your dream lifestyle now?
  • If you could live your dream lifestyle right now or even in the next five years, how would that make you feel?

These are questions we should ask ourselves daily, but most people never do it, and the ones that do, think about it in some kind of far-off dream scenario, not an actual real-life plan.

We sat down with Justin and talked about his book The Lifestyle Investor on the latest episode of The Art of Making Things Happen with Steve Sims.

During the podcast, Justin shared his path to creating a lifestyle for himself and how that helped him create a path for other entrepreneurs like him.


Along the road of trial and error, there is the tendency to want to save yourself in one fell swoop, but that’s just not realistic.

Justin states when he realized he didn’t want to be handcuffed to his business forever. It was after an 18 hour day. He was at the office, alone, and it was dark out.

He thought to himself, sure, he’s making good money, but is that all that I need? Do I want to be working this hard with a family or when I’m old?


It was then he started a two-pronged approach. First, he decided to let go of some of the control over his business. Instead of working overtime, he spent his time looking for the right people who could do that job well (at least at 80% of what he could).

That freed up his time for his second approach, acquiring assets that would allow him to live the lifestyle he wanted to live even if his business wasn’t thriving.

He states there were many failures, but that’s all part of changing your business. He admits that he never had any home runs that changed his predicament in life. It’s always just been a series of singles and doubles.


Crucial to understanding how to build his dream lifestyle was learning from others playing the game of life at a higher level than him.

He states that when he expanded his network, it opened him up to different people and strategies. It opened his eyes to ways to invest in new ways. For example, the more he spoke with very affluent people. He realized many people don’t just rely on the stock market for growing their money.

Instead, he found that many of them didn’t have any money in the stock market. Instead, they were investing in private equity of owning parts of businesses that aren’t publicly traded, real estate, and other investment opportunities.


If you’re interested in how to start investing like Justin and build your dream lifestyle today, you can learn the same process he used in his book, The Lifestyle Investor.

In it, he shares the exact strategies he used to build his dream lifestyle. You’ll also get his ten commandments of cash flow investing and financial freedom.

Not only that, but 100% of the money raised from his book goes to Love Justice International Charity that protects youth from human trafficking.

If you’re looking for more great content like this, head to The Art of Making Things Happen page and find more articles and podcast interviews.

Want to join a room full of entrepreneurs just like Justin, head over to Sims Distillery and join the private group with some of the wealthiest entrepreneurs on earth.