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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.

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Start-up Advice

Put On Your Wellies: It’s Time To Wade Into Risk

Entrepreneurs aren’t all leaping into the unknown like lemmings off a cliff, but they do need to consider it…

Chris Ogden




You’ve had a great idea. You’ve looked into its development. You’ve recognised that it has potential beyond just what Auntie Mabel and Mike From The Grocer think. And you’ve clearly nailed a pain point that can make money. Now it is time to take the risk of running with it.

Every big idea comes with risk. You can’t step out into the world of entrepreneurial thinking and business development without it. Your idea may fail. It will also be time consuming, demanding, hungry for money, and hard work. It is unrealistic to expect that your project will leap out into the world and be an unmitigated success.

It is also unrealistic to assume that it isn’t worth taking this risk.

There are steps that you can follow to ensure that your risk is managed so you aren’t blindly leaping off that cliff…

Step 01: Do your research

No, canvassing your neighbours, friends and family is not doing research. You need to know that your idea will appeal to a broad market and that it will have significant legs. This may sound like daft advice, but you would be surprised how many people think an idea will take off just because Susan in Accounting said so.

Step 02: Understand the costs

Projects are hungry for money and investment. Realistically work out your budgets and how much it will cost to take your project off the ground and then stick to it.

A calculated risk is a far better bet than one that shoots from the hip and hopes for the best. You can also use this as an opportunity to draw a clear line under where you will stop investing and end the project. If it keeps eating money and isn’t getting anywhere with results you need to be able to walk away.

Step 03: Know when to walk away

As mentioned before, this can be defined by a line you’ve drawn in the proverbial sand (and budget) but no matter where you draw this line, you have to stick to it. Often, when time, money and energy have been poured into a project it can be incredibly hard to walk away.

You think ‘but I have put so much into this, just one more’ and then it gets to a point where the ‘just one more’ has taken you so far down the line that walking away feels impossible. Leave. Learn the lessons. Apply them to your next project.

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Start-up Advice

Mind The Gap

The entrepreneur’s guide to finding the gaps and building the right solutions.

Chris Ogden




Innovation may very well be the key to business success but finding the gap into which your innovative thinking can fit is often a lot harder than people realise. Some may be struck by inspiration in the shower, others by that moment of blinding insight in a meeting, however, for most people finding that big idea isn’t that simple. They want to be an entrepreneur and start their own high-growth business, but they need some ideas on how to find that big idea.

Here are five…

1. Network

It sounds trite but networking is actually an excellent way of picking up on patterns and trends in conversation and business problems. The trick is to note them down and pay attention. Soon, you will find patterns emerging and ideas forming.

2. Look for pain

Just as networking can reveal trends in the market, so can spending time reading. The latter will also help you find common business pain points. These are the touchpoints that frustrate people, annoy business owners, affect productivity, or impact employee engagement.

Be the Panado that fixes these pains.

3. Luck


This is probably the most annoying of the ideas, but it is unfortunately (or fortunately) very true. Luck does play a role in helping you capture that big idea. However, luck isn’t just standing around and random people offering you opportunities. Luck is found at networking events, it is found in research and it is found in conversations with other entrepreneurs.

4. Luck needs courage

You may have found the big idea through your network, a pain point or pure blind luck, but if you don’t have the courage to take it and run with it, you will lose it to someone else.

Being bold in business is highly underrated because most people assume that everyone is bold and prepared to take big leaps into the unknown. However, not all brilliant entrepreneurs were ready to throw their family funds to the wind and leap into an idea – they were courageous enough to figure out a way of harnessing their ideas realistically.

5. Pay attention

This is probably one of the most vital ways of finding a gap in the market. Often, people are so busy that they don’t really pay attention to that niggling issue that always bothers them on a commute, or in a mall, or at a meeting. This niggling issue could very well be the next big business opportunity. Pay attention to it and find out if that issue can be solved with your innovative thinking.

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Start-up Advice

5 Things To Know About Your “Toddler” Business

As you navigate this new toddler phase of your business, here are five things to bear in mind.

Catherine Black




Ah, toddlers. Those irresistible bundles of joy bring a huge amount of energy, curiosity and fun to any family – but there’s also frustration and worry that comes with their unpredictability, as they grow and start to become more independent. If you own a business and it’s successfully past its “infancy” of the first year or so, it’s likely it will also go through a toddler stage of its lifecycle.

Pete Hammond, founder of luxury safari company SafariScapes, agrees with this. “Our business is now three and a half years old, and we’ve found that we’re not yet big enough to justify employing a large team of people to handle the day-to-day admin tasks, yet we still need to grow the business as well,” he says. “As a result, our main challenge is finding the time to step back and see the bigger picture. Kind of like when you are raising a busy toddler and you spend most of your time running after them!”

As you navigate this new toddler phase of your business, here are five things to bear in mind:

1. This too shall pass

Everything in life is temporary – and that goes for both the good and the bad. It’s as helpful to remember this when you’re facing the might of a toddler temper tantrum, as it is when you’re facing throws of uncertainty in your business. If your new(ish) venture is going through a rough patch in its first few years, it can be easy to think about giving up – but don’t. As long as you have an overall big idea that you believe can add value to your customers, keep pushing through the rough parts until you come out the other side.

2. Appreciate what this phase brings

The toddler years mean that the initial newborn joy is officially behind you. But these small humans also bring their own kinds of joy, as you watch them learn new skills, say funny things, and give affection back to you. While your two-year-old business may not hold the same exhilaration for you as it did during those first few months, there are now different things to appreciate about it: Maybe you’re expanding your product range, or employing new people who can take the workload off you.

3. Establish boundaries

Toddlers thrive on boundary and routine – and your toddler business will too. As it grows into a new phase, try and establish limits in terms of the type of clients you want to work with and the type of work you’ll do. It’s also a good idea to make a decision about the hours you’ll work and when you’ll switch off, which will help you establish a good work-life balance.

4. Take a break

Every parent with a toddler needs a break every now and then, even if that means a walk around the block (on your own!), a dinner out with friends, or even a few days away. The same is true for a demanding small business: every so often, remember to take time out to rest properly, where you switch off your laptop and completely unplug. You’ll return much more inspired and resilient to deal with the everyday uncertainty that it brings.

5. Give it space to make mistakes

While the unpredictability of a young business can be stressful and tiring, it’s also a time for trying new things without the risk of huge consequences if they don’t quite work. After all, it’s much simpler to change your USP if you’re a small business employing a few people, rather than a big company where 50 people are relying on you for their salary, or where you’ve received a huge amount of investment capital. While you may fail in some of the things you try with your business (in fact, this is almost guaranteed), see it as a toddler that’s resilient enough to pick itself up, dust its knees and keep moving forward.

During this phase of business growth it’s also essential to have the right type of medical aid cover. There are medical schemes such as Fedhealth which has a number of medical aid options and value-added benefits to ensure that your health and wellness is taken care of too. After all, the healthier you and your staff are, the more productive your business will be – during the toddler (business) stage and beyond.

While this phase can be frustrating, it’s a sign that your business is growing and adapting, rather than remaining in its infancy, and that can only be a good thing! So embrace the difficulties, learn from them, and watch as your business strides forward confidently into the next exciting phase.

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