Have you heard the news -- Oprah recently netted $110 million from the sale of two million shares of her ownership stock in Weight Watchers. Today, the once struggling diet program is back on top and more profitable than ever, thanks to a 10 percent investment by the media mogul in 2015 for a reported $43 million. 

Needless to say, $110 million is a great ROI for the initial investment over a three year hold. This is one of a few investments in Oprah's massive diversified investment portfolio, including her ownership shares in Teavana, now owned by Starbucks. 

The larger lesson that every savvy investor can learn, especially women, is the importance of generating passive income by investing in other businesses during early phases or stages of delayed growth. Weight Watchers was in a phase of delayed growth and valued at only $7 per share before securing funding. 

The name of the game is consistent passive income. 

You have the potential to build a diversified portfolio of investments, which focuses on generating passive income by investing in high performing/potential concepts, inventions, and innovators, without the need to be a large-scale venture capitalist. Throughout the years, I have acquired equity in more than 20 under-performing companies and the returns have accelerated the growth of my company. Other celebrities such as Beyonce have backed WTRMLN WTR, a female owned watermelon water company based in New York and several others. 

So it is time to make your money work for you. But before you invest, there are 5 things you must know about achieving the highest cash-on-cash return with the least effort. 

Always bet on the "under-dog"

Invest in relatively under-performing business models that have tremendous upside potential. Weight Watchers is a perfect example of a company that was leading the diet program scene 10 to 15 years ago. Thanks to celebrity spokes-people such as Jennifer Hudson and Jessica Simpson, the tides were beginning to turn. However, Oprah was watching the numbers and while the competition focused on discounts and other gimmicks, Oprah is always aware of her brand power and credibility. 

Under-performing companies can become lucrative investments. Whether you add cash, brand power, visibility or infuse new ideas; there is an up-side to investing in underestimated assets. 

Take a seat on the board .

You do not want to lose control of your investment. Every company that we partner with requires us to remain close to the investment with contributing interests on the board, hence, maintaining a voice on the growth of the company. In addition to Oprah having a seat on the board, she has become the face of the brand, notably the success of Weight Watchers over the past three years can be attributed to the Oprah Effect. 

Your investment must be accompanied by a guarantee that your contributions and suggestions for growth will be heard. A seat on the board will establish clear directives and goals in return for your investment. 

Play the "long game." 

 It is best to consider companies that have a long term investment strategy, which gives you more time to improve the company and on-board the right team to make your investment profitable. The long game is based on a patient approach to investing for a long-term pay-out, that will present lucrative options at the end once the company begins to perform. A long game exit can last for years, even decades, but once the company is solvent, you can decide if it is best to execute one of your exit options as outlined in your operations agreement. The key is to be patient. 

Know your strengths.

Avoid investing in businesses that fail to utilize your strengths as a leader. As an investor, you must know the value of your time and expertise, as well as the benefit to the growth of the company. For example, if your core competency is fine dining, avoid investing in a real estate company that specializes in triple net lease tenants. Oprah's connection with her investments are solely based on her core strengths, of which, she has been vocal about her desire to live a healthy life. In addition, she also uses her influence to connect her audience to what is important to her, hence, Weight Watchers is a win-win for every investor.  

Do your due diligence

Once you are in the investor drivers seat, you need to know everything about the company. Hire a law firm and accountant to review the financials before signing on the dotted line. Understandably there are risks with investing in an under-performing asset, however, your due diligence clause will give you enough time to create an improvement plan. This is the key to forecasting an on-boarding strategy that works.