12 Business Leaders discuss the Role of Risk-taking in Building Wealth

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From strategic moves in real estate to the expansion of businesses, twelve seasoned professionals share their stories of how calculated risks have shaped their wealth-building journeys.

Spanning from lessons learned in real estate investing to calculated risks propelling business expansion, these insights delve into the pivotal decisions that can make or break financial growth. Discover the risks that reaped rewards and the wisdom gained from taking chances in the world of investment and entrepreneurship.

  • Lessons Learned in Real Estate Investing
  • Successful Shift to Hotel Investments
  • Daily Risk-Taking Yields Flipping Success
  • Investing in Personal Digital Brand Growth
  • Authenticity Drives Startup’s Viral Growth
  • Comic Convention Investment Brings Wealth, Connections
  • Google Ads Gamble Secures Clientele
  • Condo Purchase Defies Market Pessimism
  • Data-Driven Exit from Bitcoin Investment
  • Diversification and Long-Term Investment Strategy
  • Strategic Domain Investments Pay Off
  • Calculated Risks Propel Business Expansion

Lessons Learned in Real Estate Investing

As a successful real estate investor, taking calculated risks plays a big part in my wealth-building journey, but it’s not something I’ve done well from the beginning. For example, the first property I ever invested in was an old house that ended up having a lot of issues, like animal infestations.

Clearly, I took a poorly calculated risk by buying that property because I wasn’t aware of the problems before investing. But it did help me learn an important lesson: Taking risks becomes a lot more manageable when you’ve done your research and understand the magnitude of the risks involved. If you go in blind, like I did that first time, it’s much harder to make smart decisions.

Thankfully, I did end up earning big returns on that property (and properties I’ve invested in since), so the investment did pay off. And now, I always do my research before signing on the dotted line to help minimize risk. –Ryan Chaw, Founder and Real Estate Investor, Newbie Real Estate Investing

Successful Shift to Hotel Investments

As real estate investors, my husband and I take calculated risks regularly. The biggest risk we took was transitioning from apartment complexes to hotels six years ago. Moving into a completely unknown industry was an enormous risk, since our entire knowledge base and experience was around long-term rentals. Hotels go beyond rentals; they are a section of the commercial real estate market; they are full businesses with significant demands around 24/7 daily operations.

Our decision to move into this market was driven by reduced ROI in the multifamily space, and we sought a more profitable investment opportunity. This transition wasn’t just about moving into a completely unknown industry; it also required us to place trust in a business partner because, in order to secure financing, we needed to demonstrate an experienced operator who could soundly manage the hotel.

The risk paid off. This particular hotel has consistently delivered high returns: even during the pandemic. It’s led to additional hotel acquisitions and a strong friendship with our hotel operator partner. We’ve built up our expertise in the hotel industry through our experience with this first successful hotel, expanded, and gained a solid understanding of what it takes to run hotels profitably.

We’re exploring international opportunities. All because we took a calculated risk six years ago and moved into hotels. That initial leap of faith opened doors we never could have imagined at the time. –Nic Stohler, Creator, Nic’s Guide

Daily Risk-Taking yields Flipping Success

I take calculated risks every day in making offers on properties that I’m going to close on and list, or close on and flip. This risk comes in many forms, such as often not having 100% of the information from a seller, not knowing where the market is going to be a couple of months from now, or simply having a project run longer than expected. 

These calculated risks that I take daily have helped tremendously in the wealth-building journey, as I’ve been able to complete some very successful flip projects, such as one I purchased last year for $460,000. In this scenario, I opted for the seller to finance me 80% of the purchase price; it was a hoarder house, and I didn’t really know where the market was going to be by the time we finished.

 Fortunately for us, by the time we listed it three months later, we were able to get 20 offers and sell the property for $770,000. Sebastian Jania, CEO, Ontario Property Buyers

Investing in Personal Digital Brand Growth

They say insanity is doing the same thing and expecting different results. Building wealth is rarely easy and requires some level of risk. This year, I risked spending dozens of hours and thousands of dollars to grow my digital brand. 

To most people, pouring a lot of energy and money into a business that isn’t guaranteed success is scary and irrational. However, I took the risk anyway because I’d already spent years learning different skills and believed in what I was doing. Despite spending thousands of dollars, my business is now profitable after taxes and expenses. 

Even if my business had failed, I would’ve gained invaluable experience I could use toward my next investment. Building wealth can be risky, but you can reduce your risk by taking the time to understand your investment and assess your risk tolerance.-Chris Alarcon, Journalist/Owner, Financially Well Off

Authenticity drives Startup’s Viral Growth

As an entrepreneur trying to grow a personal finance startup, risks are inevitable. However, one risk that I took early on that paid off immensely was getting vulnerable and sharing my personal story so openly.

Deciding to base my entire brand voice and messaging around my own memoir was risky. I shared details about my failures and shortcomings during my debt repayment journey: not ideals I thought people might want to hear about. But I knew if I only showed the highlights, it wouldn’t be authentic or establish trust. I had to risk being judged or dismissed to remain genuine.

It ended up paying off hugely. By bravely recounting even my toughest setbacks on my blog and social platforms, readers connected with my transparency. They saw themselves in my story. This drove immense word-of-mouth growth for My Millennial Guide in those early days when marketing budgets were non-existent.

Had I played it safe and kept my journey vague and surface-level, I doubt my message would have resonated so strongly. I’m grateful every day that I took the risk to stay true to my vulnerable, unconventional backstory: it fueled my wealth-building journey tremendously.Brian Meiggs, Founder, My Millennial Guide

Comic Convention Investment brings Wealth, Connections

Life is all about risk, and your wealth-building is an area that’s no different. Over the years, I’ve taken plenty of risks that have helped me grow my wealth. 

One of those is investing in a local comic convention. I saw them make a call for investors to seed some of the celebrity stars they were looking to bring in. This seemed like a great opportunity to invest but also a risky proposition. Thoughts of “What if the stars don’t pan out?” or “How will this impact other opportunities?” flooded my mind. 

Thankfully, I took the risk, and it’s paid off not only in my wealth but also in the relationships that I have built. Due to the investments, I’ve received annual returns and opportunities to see new investment opportunities through the people I’ve met. –Joseph Lalonde, Leadership Coach and Author, Reel Leadership

Google Ads Gamble secures Clientele

I took an $8,000 risk that led to my financial success. When I started my content writing agency in my twenties, I had about $8,000 in my bank account. I knew it would take a while to gain traction and find writing clients, so I took a risk.

I invested $1,000 monthly into Google Ads in an effort to get clients. I gave it my all and knew that if I couldn’t find a new, high-paying client within the next eight months, I’d have to return to my 9-to-5 job.

Fortunately, this risk paid off because I got my first client after four months, and by month six, I filled up my schedule. Because I took this calculated risk early on, I can now live a comfortable life and travel the world.Scott Lieberman, Owner, Touchdown Money

Toronto Condo purchase defies Market Pessimism

Living in one of the most expensive housing markets in the world means hearing a lot about a supposed real estate bubble. For decades, people in Toronto have claimed we’re on the verge of a mega-correction, and because of this, I’ve watched friends stay out of the housing market; for some of them, it’s now too late to buy in.

It’s a good lesson not to let unwarranted negativity seep in.

I bought my condo when I knew I could handle the payments and wanted a reliable place to live. Then I tuned out the speculative chatter, knowing that pessimists always tend to be louder than optimists. My property has increased dramatically in value, and I’m so glad I didn’t succumb to the naysaying that is practically a pastime in this city.Travis Hann, Partner, Pender & Howe

Data-Driven Exit from Bitcoin Investment

Taking calculated risks sometimes plays a large part in a wealth-building journey. If you can analyze the data and make an educated move, then it will likely turn out alright. Wealth-building, being what it is, however, there are times it just won’t.

I’ve always relied on tech-based data points when making calculated risks. Being a CTO, I put my position and my knowledge into play in order to maximize the financial return in my personal life. For example, I had invested in Bitcoin before the financial crash. For a while, it was alluring to keep my money and savings tied up in the platform, but after analyzing data points provided by other crypto agencies, I had a feeling that it was time to pull the money out, so I did.

This was approximately two months before the crash, and since then, I haven’t put a ton of stock into investing in the crypto sphere. Jack Vivian, Chief Technology Officer, Increditools

Diversification and Long-Term Investment Strategy

For me, calculated risk has meant diversifying my portfolio by combining riskier investments, such as individual stocks, with less risky investments, such as mutual funds, and always maintaining a long-term perspective. I think I have benefited greatly from resisting the urge to sell when others are fearful and from resisting the urge to hold on when others are greedy.

Remember, though, that everyone’s circumstances vary, and what may be a calculated risk for me might not be for you. It’s crucial to assess your own risk tolerance, conduct thorough research, and potentially seek advice from financial professionals before making significant financial decisions.Meredith Lepore, Content Strategist/Editor/Writer, Credello

Strategic Domain Investments pay off

We all take calculated risks, but some of us take larger ones than others. I haven’t been the best at calculating my risks, but I’ll tell you that when I stay within my circle of competence, the ability to weigh the risk versus reward becomes easier. 

For example, I purchased multiple premium website domains, several of which led to a 10x payoff by simply waiting for another party interested in the domain. This only worked because I knew the industry for these specific domains. I was certain that these were underpriced given where the industry was headed.Jason Vaught, Director of Content, SmashBrand

Calculated Risks propel Business Expansion

Taking calculated risks is an important part of building wealth for any business. There is always going to be some level of risk involved in the growth of your business. If you don’t know how to calculate potential outcomes of those risks, it’s going to be a gamble whether you succeed or fail. At Oxygen Plus, we’ve taken a number of risks, such as expanding into new markets. We could have easily spent more of our budget on marketing to the same audience, but our growth would have slowed significantly and possibly even stopped.

By calculating the potential that other markets provided for us to grow, we could determine where to look first to expand. We also assessed the potential for failure, which meant we could create backup plans for if our expansion didn’t work. That’s something we’ve always done when taking calculated risks, and, in the times when things haven’t gone our way, we could still fix things quickly and come out on top.Lauren Carlstrom, COO, Oxygen Plus


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