Investing to WIN #034 — Why Finding Your Why Matters in Real Estate Investing Businesses

(with Garret Wong)

Many investors chase deals, doors, and cash flow without ever asking why they’re doing it. When the market shifts or life throws a curveball, that lack of clarity creates burnout, doubt, and stalled momentum.

In this solo episode, Garret Wong explains why defining your personal “why” is the foundation for long-term success in real estate and in life. Before you set your next investing goal, this conversation challenges you to get clear on what truly drives you.

Duration: 12:00

Date: Oct 24, 2023

Guest: Garret Wong - Founder, Upper Edge Property Management

WATCH THE FULL EPISODE:

Want the full experience? Watch directly on YouTube to support the channel and get recommendations for similar episodes.

What You’ll Learn

• How to apply Simon Sinek’s Golden Circle to your real estate career

• The difference between what you do and why you do it

• A practical approach to uncovering your personal “why”

• How a clear why statement guides daily decisions and long-term goals

• Why fulfillment at work directly impacts investing performance

• How to stay committed to your vision during setbacks and uncertainty

Memorable Moments

"I truly believe you have to find your why."

"Everybody deserves to wake up feeling fulfilled."

"Your why should guide every decision you make."

Episode Summary

Many real estate investors focus on strategy, returns, and scaling without first defining their deeper purpose. This episode addresses a common blind spot: building a portfolio without clarity on why you’re building it in the first place.

Garret Wong explores Simon Sinek’s concept of “Start With Why” and explains how the Golden Circle framework applies not just to companies, but to individuals. The surprising truth is that most people know what they do and how they do it, but struggle to articulate why they do it. That lack of clarity leads to frustration, burnout, and misaligned goals.

This episode is for investors who feel busy but not fulfilled, successful but not satisfied. After watching, you’ll be equipped to define a clear why statement that shapes your investing decisions, strengthens your leadership, and creates long-term alignment between your business and your life.

Chapter Timestamps

[00:00] – Why fulfillment matters in real estate investing

[01:30] – Understanding Simon Sinek’s Golden Circle

[03:06] – How to begin discovering your personal why

[04:34] – Crafting a clear and actionable why statement

[06:08] – Staying committed to your purpose during challenges

[07:39] – A challenge to define your why before setting goals

About Garret Wong

Garret Wong is the Founder of Upper Edge Property Management and host of the Investing to Win podcast. He has built his career around real estate investing, property management, and leadership development.

Through his work, Garret focuses on helping investors build sustainable portfolios while maintaining balance and fulfillment. His approach blends practical investing experience with a strong emphasis on purpose-driven decision making.

Full Episode Transcript

Hide
Show

00:00.37

wongga

Hello listeners this is Garret Wong your host of the investing to win podcast another solo episode for you today if you've been listening to the last few episodes. You'll note that I'm talking a lot about fulfillment at work fulfillment in your life. And yes, this is a real estate podcast. But I I think I'm just on just on the theme of balance lately maybe because I've been so busy maybe because I had those 2 life scares in 2022 and I truly believe that in order for you to get out of your own way and be. Successful in real estate investing to even choose your goals of real estate investing which you want. It's super important to find your why? Okay so that's ah, it's kind of a spoiler find your why is a book that. Really changed and shaped my thinking. The author is Simon Sinek who is renowned for his you know expertise in leadership and management kind of incorporat but he also has um, a personal component to it. So. I think today I'm just going to spend a few minutes maybe outlining how I found my why and obviously you know I'm pursuing my passion now. Yes I have the management company but I'm a little more passive in that and my why you know is to.


01:30.30

wongga

To help people and problem solve but also in the context on the context of real estate and real estate development. So let's let's back up a little bit so Simon Sinek he has this book. Um, find your why and start with why and he really applies it to. Companies and we did this for our company and I think that's important to to delve into that before you understand why you need to apply it to a personal level so he has the concept of the golden circle and he's got 3 terms in here. The what the? How and the why and really what he when he refers to a company. It's many companies know what they do, they might even know how they do it but many companies don't know why they do it. Why do they exist. So. We did that as a company and when you try to translate those concepts over to the personal realm the why then is your purpose or belief that inspires you the how would be the actions you take to realize your why and the what. Is the result of those actions and what you deliver to the world. So when you're talking about trying to go through why to personal discovery Simon Sinek recognized the need for a practical approach to internalize in this philosophy. That's where you know find your why comes from.


03:06.68

wongga

It's not just a manual, but it's it's kind of a beacon leading you to the path of self-realization. It's kind of experiencing a paradigm shift you direct your energy towards your your life's true calling and while that mind so might sound a little corny. You know when you think about it. Something that he said and he had some videos in the company portion of it is everybody deserves to wake up in the morning go to work and feel fulfilled and if you're listening to this and that's not you. Don't wake up in the morning and you're completely fulfilled excited to go to work then there's a problem because how long should you be okay in that situation is it temporary have you been doing it for years. You know like I said about bull setting. So. When you're talking about unveiling your your unique why the process really starts with gathering and this is straight from his book. This isn't from me but the process starts with gathering stories and identifying themes from your life. This discovery involves understanding what makes you come alive or feel fulfilled so I can't tell you this obviously this is a self-discovery process. So as you go through this crafting your wise statement. It's not a mundane task. It's kind of a declaration of your identity. It's.


04:34.32

wongga

Should be succinct. It should be clear action oriented providing you with a guideline for making your life's big and small decisions because if your why statement is your guiding light that everything around you everything you do for the rest of your life should be around that Why statement. So when you find your y statement you really then have to embrace it. Um, when you embrace it. It's going to amplify exactly what you understand of every struggle all of those Journeys contributing to that larger personal Narrative. You have to understand your why, but that's the beginning not the end I talked about a journey So an ongoing journey that's with challenges. Of course you're going to find its why statement. But you're going to encounter personal doubt external pressures. But these are the tribulations to test the strength of your commitment to your why? So you know I challenge you for call to action because if you discover your why? It's a gift not just to yourself but to those around you to those in your life to those that share. All those little moments with you So Share your why you want to live by it and let it resonate with those people around you if you can do that you're going to inspire. Ah you know, inspire others you're going to create a ripple effect that extends far beyond your personal sphere.


06:08.67

wongga

Journey might be by you as an individual but again the destination should encompass spreading that message for you now I know that I'm speaking very abstract. So let's get maybe down to details I want to challenge you okay because I went through my personal why statement I know what it is and if you're listening to this and you don't know what your why statement is I'd encourage you to even read the book read the book. Get some focus in your life. Make sure that when you get up every day every action that you're taking whatever your why might be is to fulfill that why? Okay, um, yes, like I said the journey is going to have its challenges but you want to embrace that journey. It's about growth about passion and purpose. So. Yeah I'd invite you to embark on that journey. Um, it's made me a better person. It's made me focus for sure. Um, and I'm I'm happier because of it because I no longer feel like I'm spinning my wheels and when things get tough I remind myself of that. Why. And it has definitely made me a better person. A better business person better husband a better friend and a better leader. So I hope you got something out of this short little solo episode find your why start with why by Simon Sinek look it up.


07:39.72

wongga

And drop me a comment um on one of my social media channels I'd love to see if this has inspired you to really you know, find that journey and and change your life if you feel that you're not fulfilled but anyways, um, that is it for today we will. Begin next week talking about real estate I've got some really cool podcast guests coming up in all different spheres and different asset classes. So I think you're going to enjoy that but find your why because otherwise you won't know if that is what you're really going towards and focusing on. Until next time invest to win.


Want more episodes like this?

Join my email list and I’ll send the best insights from real estate + business + investing.