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Start-up Advice

3 Inspiring Business Lessons From Billionaire Media Mogul Oprah Winfrey

From safeguarding your brand to trusting your gut, there’s much to learn from the wildly successful ascent of Lady O, the ‘queen of all media.’

Kim Lachance Shandrow




Like many seasoned entrepreneurs, Oprah Winfrey views failure as “another stepping stone to greatness.” For her, it has been, and then some.

In 1977, decades before she became a billionaire media mogul, she was fired from her job as a reporter at Baltimore’s WJZ-TV. Her boss said she was “unfit for television news.” She was “devastated,” but she didn’t quit.

The “queen of all media” quickly rose from rejection and found her calling in daytime TV. Then came her eponymous talk show and 25 internationally syndicated seasons of success. The Mississippi native later launched her book club, magazine and TV network. Today, she sits at the helm of a multi-billion-dollar media empire.

“Lady O” is best known as an outspoken TV host, actress and philanthropist, but she’s also an incredibly accomplished founder. The chairman and CEO of Harpo, Inc., Winfrey made history when she became the first first woman to own and produce her own talk show. She’s now one of the wealthiest and most successful business leaders in the world.

Related: 10 People Who Became Wildly Successful After Facing Rejection

There are many inspiring lessons entrepreneurs can learn from her remarkable journey from a “poor, deprived ghetto girl” to self-made billionaire. Here are three:

1. Trust your instincts

Winfrey is a known to be a big believer in listening to her instincts and honouring them, a skill that she credits much of her success to. Trusting her gut has helped her steer clear of trouble in her personal and professional life, she claims. “I know for sure whenever your gut is out of kilter, trouble awaits,” she wrote in O Magazine.

“Your gut is your inner compass. Whenever you have to consult with other people for an answer, you’re headed in the wrong direction.”

During a 2011 OWN Network Lifeclass session, she expanded on why she feels it’s important to mind to your inner voice: “Listening to your life as it whispers to you first, so that it does not have to knock you upside the head with a brick or come crashing down on you as a brick wall, is one of the greatest principles of life.”

Lesson: Pay close attention to your instinctual reactions whenever you’re faced with a considerable business decision. Hearing – and heeding – even the slightest bit of hesitancy from within could potentially stop you from making poor choices that could impact your bottom line, now and in the years to come. In other words, as Winfrey says, “Follow your instincts. That’s where true wisdom manifests itself.”

Related: 24 Quotes On Success From Oprah Winfrey

2. Fiercely protect your brand

From her namesake talk show to O Magazine, from to OWN Network, Winfrey has worked tirelessly to transform her unique name from a stumper – which once prompted viewers to ask “What is an Oprah?” – into a household name.

To legally protect her brand, she’s trademarked every one of her companies and their many subsidiaries, and her legal team actively pursues those who infringe upon her trademarks. Most recently, on May 19, she filed a federal application to trademark a suite of foods and other goods branded under the name “Oprah’s Kitchen.”

Lesson: Strengthen your brand and safeguard it from misuse and dilution by trademarking your business name and logo. Doing so gives you the ability to control how they are publicly used and displayed.

3. Value your fans

One of Winfrey’s favourite things about her talk show was her famous “Oprah’s Favourite Things,” a sometimes hilariously high-energy segment (check this SNL parody) during which audience members found free goodies of all kinds tucked beneath their seats on set. The popular segment’s purpose was twofold: First, it was product placement promotional gold and, second, it enabled Winfrey to connect with her brand fans in a memorable and public way.

Related: 10 Successful SA Women Entrepreneurs’ Top Advice On Balancing Work And Family

“The surest way to bring goodness to yourself is to make your intention to do good for somebody else,” Winfrey, who gives away millions to charity every year, once said. The concept is simple:

What goes around comes around. Do good and good shall be done unto you.

Lesson: Surprise your customers and brand advocates with extra value from time to time, perhaps in the form of coupons, discounts and giveaways. Giving a little extra can go a long way when it comes to locking in their loyalty and repeat business.

This article was originally posted here on

Start-up Advice

Alan Knott-Craig Answers Your Questions On Money And Partners

From starting the right business, to managing business partners and finding your magic number, there is a secret to happiness.

Alan Knott-Craig




If I get rich will I be happy? — JC Lately

Does money equal happiness? Mostly, yes. Research in the US shows that your happiness is proportionate to your earnings up until you earn $80 000 per annum. Thereafter, incremental income gains have a negligible effect on your happiness.

In other words: More money will make you happy as long as you’re poor. Once you break out of poverty and enter a comfortable middle-class existence, more money will not make you happier.

These are the top three for old folks:

  • I wish I’d spent more time with family.
  • I wish I’d taken more risks.
  • I wish I’d travelled more.

Therein lies the secret to happiness. Spend time with your family. Take risks. Travel.

But first, make money. Don’t do any of the above until you’re making enough money not be stressed about money.

Related: Your Questions Answered With Alan Knott-Craig

What is the magic number? — Mushti

The magic number is the amount of money you need to not worry about money ever again. If you don’t need toys like Ferraris, yachts and jets, the magic number is R130 million. Here’s the math: R130 million will earn R9,1 million in interest annually (assuming 7% interest). After tax that is R5,46 million.

Assuming you need 50% to maintain a good lifestyle, that leaves approximately R2,7 million for reinvestment, which is enough to keep your capital amount in touch with inflation for 50 years. The balance of R2,7 million (after tax) is for your living costs. In South Africa, R2,7 million will afford you a lifestyle that allows you to send your kids to a great school and university, to travel overseas a couple of times a year, and to live in a comfortable house.

Over time your living costs (and inflation) will eat into your capital amount. After 50 years you should be down to nil, assuming you earn zero other income in that time.

In 50 years, you will probably be dead. If you’re not dead, your kids will be able to support you (because they love you and they have a great university education).

I am the sole director of a company (the others still have full-time jobs and don’t want to be conflicted) and there is pro-rata shareholding based on our initial shareholder loans. However, I am putting in most of the hard work, together with one of the other actuaries. How best do I manage the director/shareholder dynamic? I obviously want to make as much progress as possible but there are times when I need the input from the others (and their responses aren’t always as quick as I would like). — Mike

If you have any perception of unfairness regarding effort/risk vs reward, deal with it NOW! You can’t do so later. The best approach is honesty. Call your partners together. Explain your thinking. Perhaps argue for 25% ‘sweat equity’ for yourself. Everyone dilutes accordingly. Ideally cut a deal whereby you have an option to pay back all their loans, plus interest, within six months, and you get 100% of equity (unless they quit their jobs and join full-time).

Equity dissent must be resolved long before the business makes money, otherwise it will never be resolved.

Related: Alan Knott-Craig’s Answers On Selling Internationally And Researching Your Idea

What do you think of WiFi in taxis?— Ntembeko

It’s a good idea, but not original. Before embarking on a start-up, you should survey the landscape for competitors. Just because there are none doesn’t mean no one has tried your idea.

It just means that everyone that tried has failed. You need to be 100% sure that you have some ‘edge’ that makes you different from everyone who came before you (and failed). Otherwise you will fail. What is your advantage that is different to everyone who came before?

Read ‘Be A Hero’ today


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Start-up Advice

What You Need To Know About The Lean Start-up Model

The Lean Start-up philosophy was developed by Eric Ries, a Silicon Valley-based entrepreneur who also sat on venture capital advisory boards. He published The Lean Startup in 2011, igniting a movement around a new way of doing business.





The model follows key precepts that include:

Taking untested products to market

The fact that too many start-ups begin with an idea for a product that they think people want, spending months (or even years) perfecting that product without ever testing it in the market with prospective customers.

When they fail to reach broad uptake from customers, it’s often because they never spoke to prospective customers and determined whether or not the product was interesting. The earlier you can determine customer feedback, the quicker you can adjust your model to suit market needs.

The ‘build-measure-learn’ feedback loop is a core component of lean start-up methodology

The first step is figuring out the problem that needs to be solved and then developing a minimum viable product (MVP) to begin the process of learning as quickly as possible. Once the MVP is established, a start-up can work on tuning the engine. This will involve measurement and learning and must include actionable metrics that can demonstrate cause and effect.

Utilising an investigative development method called the ‘Five Whys’

This involves asking simple questions to study and solve problems across the business journey. When this process of measuring and learning is done correctly, it will be clear that a company is either moving the drivers of the business model or not. If not, it is a sign that it is time to pivot or make a structural course correction to test a new fundamental hypothesis about the product, strategy and engine of growth.

Lean isn’t only about spending less money

It’s also not only about failing fast and as cheaply as possible. It’s about putting a process in place, and following a methodology around product development that allows the business to course correct.

Progress in manufacturing is measured by the production of high quality goods

The unit of progress for lean start-ups is validated learning. This is a rigorous method for demonstrating progress when an entrepreneur is embedded in the soil of extreme uncertainty. Once entrepreneurs embrace validated learning, the development process can shrink substantially. When you focus on figuring the right thing to build — the thing customers want and will pay for, rather than an idea you think is good — you need not spend months waiting for a product beta launch to change the company’s direction. Instead, entrepreneurs can adapt their plans incrementally, inch by inch, minute by minute.


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Start-up Advice

Start-Up Law:  I’m A Start-up Founder. Can I Pay Employees With Shares?

Bulking up employee salaries with equity is a common method to attract, retain and incentivise top talent.




Every early stage start-up company battles with restricted cash flow and not being able to pay market related salaries to their employees. Bulking up employee salaries with equity is a common method to attract, retain and incentivise top talent.

Can I pay salaries with shares?

South African labour laws require that employees be paid certain minimum wages, and “remuneration”, as defined within the Basic Conditions of Employment Amendment Act, either means in ‘money or in kind’.  ’In kind’ does not include shares or participation in share incentive schemes, as determined by the Minister of Labour. As such, there is no room for start-ups to completely substitute paying salaries with shares or share options. However, there is no restriction in topping up below market related salaries with equity via an employee share ownership plan (‘ESOP‘).

Related: 7 Ingredients Of Small Business Success Online

Employee Share Ownership Plans

There are a variety of ways in which employees can be incentivised, and it will always be important for the start-up founders to consider what goal they wish to achieve by incentivising their employees.

ESOPs can be structured in several ways, for example: employees may be offered direct shareholding in the company, options for the acquisition of shares in the future; or alternatively, a phantom / notional share scheme can be set up.

ESOPs permit employees to share in the company’s success without requiring a start-up business to spend precious cash. In fact, ESOPs can contribute capital to a company where employees need to pay an exercise price for their share options or shares.

The primary disadvantage of ESOPs is the possible dilution of the Founder’s equity. For employees, the main disadvantage of an ESOP compared to cash bonuses or bigger salaries, is the lack of liquidity. If the company does not grow bigger and its shares does not become more valuable, the shares may ultimately prove to be worthless.

Related: 7 Strategies For Development As An Entrepreneur

Key Features

Some key features to consider when setting up an ESOP are:

  • ELIGIBILITY – who will be allowed to participate? Full time employees? Part-time employees? Advisors?
  • POOL SIZE – what percentage of shares will be allocated to incentivise employees?
  • RESTRICTIONS – will employees be able to sell their shares immediately?
  • VESTING – will there be a minimum period that service employees will have to serve with the start-up to receive the economic benefit of his or her shares?

Employee share ownership plans are great corporate structuring mechanisms for attracting and retaining employees, as well as fostering an understanding of the company ethos and encouraging loyalty and productivity. It is essential when implementing an ESOP that all the tax implications are considered and that the correct structure and legal documentation are in place.

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