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Start-up Advice

8 Entrepreneurs Share Their Best Advice For When The Going Gets Tough

How should you respond to adversity?

Matthew Baker




Despite the “overnight” success stories you read about in glossy business magazines, the overwhelming majority of successful businesses take years, if not decades, to build. It’s never easy. Entrepreneurs often ride a roller coaster of highs and lows that feel even more intense because they’re running the show. Steve jobs once said,

“I’m convinced that about half of what separates the successful entrepreneurs from the non-successful ones is pure perseverance.”

I asked a few highly successful founders to share their advice for other entrepreneurs going through a rough patch. Here’s what they shared.

1. Reconnect with your “why”

“It’s easy to get sucked into the minutia of the day-to-day tasks of building a business, so take the time to get back to your inspiration and reconnect with your mission and vision. Going back to your ‘why’ can help shift your mindset since it’s the only thing that matters.” – Payal Kadakia, ClassPass Founder and Executive Chairman

Related: Why Your Start-up Needs Some Legal Advice

2. Don’t sugarcoat things with your team

Bill Clerico wepay

“For an entrepreneur, it’s important to remember that it’s not just about you, but about your whole team, too. Your team can either be one cohesive unit that helps you get through a challenge, or they can become frantic and frustrated – making the situations worse and harder on you as a leader. When addressing low points, you should be honest with your team and not sugarcoat anything because they will understand what’s happening. At the same time, you should express context for those challenges, optimism about the long run, and where you ultimately want to end up. If you do that well, your team will come together, stick with you through the tough times, and bring a lot of energy.” – Bill Clerico, WePay CEO and Co-founder

3. Imagine someone else in charge

“I find that when I hit a low point in our business, I lose brain cycles to questions such as: How did I get here? What could I have done to prevent this? Am I good enough to solve this problem? It makes it hard to figure out a path forward. I have a little hack that helps in these moments. I imagine what would happen if someone I really admire took over my job tomorrow. It helps to picture someone I know well, someone with whom I’ve worked. I ask myself, what would this person do, and what would the outcome look like? I write it all down. Then I just go do it.” – Anna M. Counselman, Upstart Co-founder and Head of Operations

Related: 8 Pieces Of Sage Advice From Ernest Corbett of Tintswalo Safari Lodges

4. Keep a positive mind

daniel saks appdirect

“I believe strongly in the value of Positive Mental Attitude (PMA). Building a business is certainly not easy, but you can never underestimate the importance of positivity as a means to effect change. Staying close to your values and focusing on the end game, not the short term, helps to keep you pushing forward in those rough patches.” – Daniel Saks, AppDirect Co-CEO and Co-founder

5. Lean into the discomfort

“Many extraordinary athletes love to compete more than they love to win. Keep that attitude about the journey of building. Failing is absolutely necessary to be successful over the long term. There aren’t shortcuts, and it’s going to be hard. Instead of trying to avoid the discomfort, be brave and lean into it. Say, ‘I failed!’ and let yourself embrace whatever emotions come with that. These feelings are important because they motivate us to try something harder. Once you’ve done that, you can put blame and your failings aside and try to understand what made you fail. Then own it. Take responsibility. It’s a beautiful, unique lesson that only that scenario could teach you. Reflect and learn from it.” – Marcela Sapone, Hello Alfred CEO and Co-founder

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

6. Find people who can relate

Lauren Behrens Wu shippo

“No one tells you how hard it is to be a founder. From the outside, everything looks like an overnight success and everyone is always ‘crushing it.’ But, it’s simply not true. Success is a rollercoaster, and the ride doesn’t end. I’ve found having people to talk to and relate to has shown me that the emotional ups and downs are normal.

“Talk to people who can relate and will listen without judgment. Founders always seem to appear as if they have all the answers, but if you find others you can trust and have honest conversations with, you’ll find you’re not the only one having – Lauren Behrens Wu, Shippo CEO and Co-founder

7. Surround yourself with the right people

“In the company’s first two years, we were working from my parents’ basement with about 10 customers each paying us $10 a month. I was taking business calls from a furnace room. All the signs were there that we were failing, and I was close to calling it quits. I remember glancing over at my co-founder Levi, coding away at a desk and bobbing his head to some tunes.

“He was totally loving what we were doing, what we were building. I remember thinking, There’s a guy who’s way smarter than me, and he’s all in. I knew if I were to ask him how things were going, he’d say, ‘Mike, we had seven people try the product today, that’s amazing, right?’

“That kind of positivity kept me going in the early days. What I can offer is this: When you’re having that kind of self doubt, surround yourself with people who will inspire you and keep you going.” – Mike McDerment, FreshBooks CEO and Co-founder

Related: 15 Of South Africa’s Business Leaders’ Best Advice For Your Business

8. Know that there is no perfect plan

David Cancel

“Keep moving. Even if you’re not 100 percent sure what to do, make something up. In the early days of a startup, it can feel like you’re wandering through the desert. So imagine you’re there and you look 360 degrees around and everywhere you look you see the horizon. It looks the same in every direction and there are no landmarks that you can go toward. There’s no obvious way out of the desert, and you don’t know if you’re moving forward or you’re moving backwards, moving to the left or moving to the right. In other words, you don’t know if what you’re doing is getting you closer to your end goal or getting you further away from it. In these cases, you have to make it up.

“It’s not an answer that people want to hear, because for most people, building a business is about having a plan and an excel sheet and a formula that can predict everything. But, in the early stages, you have to recognise that you’re going to have to make some best guesses and maybe some of them are based on intuition. And then based on those guesses, you’re going to set some goals – like the number of steps you walk each day. Whatever your goals are, you’re going to make them up and you’re going to set daily, hourly, weekly goals that you can achieve. That’s how you get out of the desert.” – David Cancel, Drift CEO and Founder

This article was originally posted here on

Matt Baker is VP Strategic Planning at FreshBooks, a cloud accounting software solution for small business owners and self-employed professionals. He focuses on corporate strategy, long-term planning, market insights, and public relations. Prior to FreshBooks, Baker was an engagement manager at McKinsey & Company and a senior strategist at Google, Inc.

Company Posts

Register A Company In South Africa

With over 120 Start-up Services, Company Partners is the perfect Partner for Company, Tender and Contract compliance.

Company Partners




Company Partners is the leading Company Registration Service Provider in South Africa, offering a One-Stop-Shop for all the Company Registration and Tender Compliance Documents.

With over 120 Start-up Services, Company Partners is the perfect Partner for Company, Tender and Contract compliance.

Established in 2006, Company Partners guarantees that the services they offer meet the standards of the best in the industry. Over 30 full-time Consultants offer services and standards of the highest quality.

Company Registration Benefits

Your Company Structure is the first consideration you need to make when you want to register a new Company at the CIPC. The preferred choice of a legal entity for most Businesses is a Pty Company.

Related: Business Model Design – Picking The Business Model That Works For You

Here’s why:

  1. You protect your personal life and assets from your business when you register a company. If one runs a business, it is necessary to operate in a safe legal structure where your business assets and risks are separated from your personal ones.
  2. You look more professional when you operate under a registered company name. If you want to obtain a large contract or a tender, it appears more professional to trade in a Pty Company capacity than in your own name.
  3. Most Suppliers and Government Departments require businesses to be registered as a Company to apply for their Tenders and Contracts.

How to Register a Company

Step 1: Complete and submit the easy online sign-up form here.

Step 2: Your dedicated Consultant will call you to assist you with any questions you may have.

Step 3: Email your ID and easy supported documents – which your Consultant will explain.

Step 4: Within a few days you will receive your brand new Company ready to use for Tenders and Contracts, via email. You can contact your Consultant at any time on a toll-free number.

Related: New Fund For Small Businesses To Be Developed

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Luckily, getting your own Shelf Company is easy in terms of compliance. All that’s required is that you are at least 18 years of age, an ID document / Passport and a South African Business Address.

Why use Company Partners to Register a Company?

Fast timeframes: Your Company will be registered fast and effectively online. Your documentation is set-up in less than 24 hours, after which CIPC will process it.

Simple requirements: The only requirement for Company Registration is an ID / Passport. Everything gets done online, so you can be based anywhere in South Africa or the World.

Dedicated Consultant: Your own dedicated professional Consultant takes care of the entire process – he or she is available on his / her email and also on a toll-free number.

Professional Service: With years of experience of representing our Clients in Government, the entire process runs smoothly over the Internet. No lost documents and no frustration.

Company Partners completes all necessary applications correctly and reviews all the paperwork for you. You simply have to wait for your company documents via e-mail, confirming when you may start trading using your registration detail.

Related: Beauty Of Failure: The Art Of Embracing Rejection

After Company Registration

Any new Business needs guidance to prepare for Tenders and Contracts. After Company Partners gets you registered for your Company, Company Partners can assist you through the entire Company start-up process (optional).

That means they will ensure you have everything you need for a Tender or Contract application like a new PTY Company, BEE, Tax Clearance, VAT Registration, Logo Design, Website, Business Plan, COID, Letter of Good Standing, NHBRC, Accounting, Payroll and more.

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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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