Being a founder, entrepreneur, or a business owner can have many exciting and thrilling moments. But it is also punctuated with periods of doubt, slump, and anxiety. So how does one successfully and healthily ride the highs and lows of Entrepreneurship? In this series, called “How To Successfully Ride The Emotional Highs & Lows Of Being An Entrepreneur“ we are talking to successful entrepreneurs who can share stories from their experience. I had the pleasure of interviewing Chandra Clarke and Terence Johnson.
Chandra Clarke and Terence Johnson are award-winning entrepreneurs who built their basement start-up into a multi-million dollar company that was eventually acquired, all while raising four kids. Their new book, The Entrepreneurial Parent: Run Your Business, Raise Your Business, Raise Your Family, Leep Your Sanity! talks about how they managed it all.
Thank you so much for joining us in this interview series! Before we dive in, our readers would love to “get to know you” a bit better. Can you tell us a bit about your ‘backstory’ and how you got started?
Chandra Clarke: I started out as a reporter for a number of local newspapers, and had worked my way up to managing editor of a community weekly. Terry had recently graduated from Oxford and was working for a university consortium called The Europaeum when we met. I’m from Canada, Terry is from the UK. We met online, and we’ve been living and business partners ever since.
What was the “Aha Moment” that led to the idea for your current company? Can you share that story with us?
Chandra Clarke: For our previous company, Scribendi.com, that moment was definitely when a press release from a local police station crossed my desk, announcing a “marijuana bust.” Clearly, there was a need for an on-demand proofreading service. That was back in 1997. The concept took off almost immediately.
Terence Johnson: Our latest venture, TurnsandTales.com, is a board game café and indie bookstore. Since selling Scribendi.com I’ve been volunteering for a number of local charities and non-profits. After the subject of needing more things to do downtown had come up a few dozen times, I started to look at what might work and this idea resonated with people who were inspired by similar ventures in bigger cities. This is something we’re doing for our community, to bring the concept to our local downtown.
In your opinion, were you a natural born entrepreneur or did you develop that aptitude later on? Can you explain what you mean?
Terence Johnson: I don’t think either of us thought of ourselves that way, to begin with. Problem solvers, possibly. People willing to take leadership positions, show initiative, definitely. Advocacy and public policy work were what I thought I would be doing. But I’m not sure I saw myself going into business.
Chandra Clarke: Me neither, actually. Writing was going to be my thing. But it’s a hard way to make a living, and it turned out we were pretty good at business. And now we do all of those things.
Was there somebody in your life who inspired or helped you to start your journey with your business? Can you share a story with us?
Terence Johnson: One of the things I found out working in academia was that it’s not just students rushing to get an essay finished at 2 am who make grammatical errors. You can be brilliant in your field of research and still make howlers in English, particularly if you’re under time pressure. That’s why I knew Chandra’s vision of a proofreading service that would be available 24/7, ready to make you look good and communicate your ideas clearly, was worth investing the time and effort in.
What do you think makes your company stand out? Can you share a story?
What took Scribendi from a basement startup to a global company was our attitude to service, both for our customers and our globally distributed team of editors. We worked really hard to make sure everyone felt engaged and connected, no matter where they were in the world.
You are a successful business leader. Which three character traits do you think were most instrumental to your success? Can you please share a story or example for each?
Chandra Clarke: For me, I would say the character trait that has served me well is being organized. As an entrepreneur and as a parent, you find yourself switching between “modes” all the time and juggling the demands of your kids and your staff. I remember one day in particular: that morning, I had taken our son to playgroup and spent the morning on the floor with him and his toys. An hour after that, I was in my business clothes, seated at a boardroom table taking a call from a client and discussing currency conversion rates. You can’t switch back and forth like that without having everything ready to go ahead of time.
Terence Johnson: I would say mine would be thinking ahead, and putting myself in the shoes of other people, engaging with people, and finding out what it will take to empower them. One of my roles was (and still is) to manage our IT requirements. It’s not enough to be able to think about what you might need right now. You have to be able to think about what you might need in the next two or three years and start building toward that. You have to be able to think like your users and customers. How are they likely to use the system? When the system breaks because a user did something unexpected, the user isn’t necessarily wrong. What can we learn and change to fulfill their expectations? When evaluating the landscape of emerging technologies, which of them will actually make a difference to the people you serve? We dived deep into AI research early, and not to replace human “costs.” We did it to empower people to create more value in the same amount of time and grow the share of their time spent on more interesting tasks.
Often leaders are asked to share the best advice they received. But let’s reverse the question. Can you share a story about advice you’ve received that you now wish you never followed?
Chandra Clarke: Definitely. You’re often told to diversify, to protect against shifts in your industry or market. This might work when you’re a big company, but when you’re a small or medium venture, that advice can lead you to waste a lot of resources on something you can’t do properly… and meanwhile takes your focus off growing the thing you can already do well. We ventured into translation services at one point, and it was disastrous because we didn’t have enough spare resources to jump into it properly. Lesson learned.
Which tips would you recommend to your colleagues in your industry to help them create a work culture in which employees thrive and do not “burn out” or get overwhelmed?
Terence Johnson: Having clearly defined roles and processes is really important. If your staff is always having to wing it, there’s a really good chance they’re going to do something wrong, which then can have knock-on consequences for their colleagues, the clients they look after, and so on. You don’t want a business where you’re constantly having to ‘put out fires.’ That’s exhausting for you and your employees. You need energy for creativity and mental space to innovate.
What would you advise other business leaders to do in order to build trust, credibility, and Authority in their industry?
Chandra Clarke: Seek out the certifications in your industry. If one doesn’t exist, consider developing one. And don’t forget to hustle for awards. It might take you a while to earn one, but they’re worth it.
Can you help articulate why doing that is essential today?
Terence Johnson: The barriers to entry in most industries have fallen considerably. Almost anyone can hang out in their shingle and claim to be in business. So you’ll have to work harder to stand out, and to earn the trust of your potential customers. Of course, that doesn’t stop with getting them in the door. You have to continue to earn their trust every step of the way.
What are the most common mistakes you have seen CEOs & founders make when they start a business? What can be done to avoid those errors?
Chandra Clarke: Buying the gold plated equipment when the bronze would do. This is especially true in businesses where cash flow is critical to operations. Definitely give yourself room to grow, but don’t buy the most expensive software with 400 features, the uber executive desk and chair set, or the embossed stationary. Buy just what you need to operate professionally, and level up from there.
Ok fantastic. Thank you for those excellent insights, Let’s now shift to the main focus of our interview about How to Successfully Ride The Emotional Highs & Lows Of Being An Entrepreneur. The journey of an entrepreneur is never easy, and is filled with challenges, failures, setbacks, as well as joys, thrills and celebrations. This might be intuitive, but I think it will be very useful to specifically articulate it. Can you describe to our readers why no matter how successful you are as an entrepreneur, you will always have fairly dramatic highs and lows? Particularly, can you help explain why this is different from someone with a “regular job”?
Terence Johnson: In our book, we talk about how entrepreneurial life is such a roller coaster. I think this is because it’s all so personal. In a job, you are usually one of many people involved in any given project, and more often than not, someone else higher up the food chain sets the parameters and objectives.
As an entrepreneur, you are the higher up. You make the decisions, you set the metrics for success or failure, and it’s typically your personal bank account on the line. So when you succeed, it’s a rush, and when you fail, it’s gutwrenching, and when you’re waiting to find out which way something’s going to go, it’s agonizing.
Do you feel comfortable sharing a story from your own experience about how you felt unusually high and excited as a result of your business? We would love to hear it.
Chandra Clarke: For sure. I think a good example was the first time we got a call, out of the blue, from an investment fund. Some private funds do this, they look at bigger players in certain industries, and they examine these players to see if they’re acquisition targets. We weren’t super big when we got this call, but clearly, we’d made enough noise to get noticed. That was an awesome feeling, as it was outside validation. Plus, it was also very encouraging: it meant we had something interesting enough to sell at some point (as we eventually did).
Do you feel comfortable sharing a story from your own experience about how you felt unusually low, and vulnerable as a result of your business? We would love to hear it.
Terence Johnson: Our first business was entirely based online. One evening, our system completely froze. Enterprise-grade, dual-redundant everything that had cost us a small fortune had still found a one-in-million way to go thoroughly belly-up. It was down for hours. That might not sound like much, but at the time we were offering eight-hour turnaround times on proofreading orders, and so we had dozens of orders we had to manually return, and dozens more we couldn’t access to the process. Our poor customer service reps were also busy fielding calls from anxious remote staff who couldn’t fulfill their tasks.
I was up for 36 hours straight trying to work with our service provider and hardware vendor to find the problem and fix it. And then we had all the late orders to either fill or refund, all the customer queries to cope with, plus all the regular orders that came in when the site was back up. The system continued to be fragile for some days after that, running off our disaster-recovery hardware rather than the primary. The real worry the whole time was that it might get so bad that it would force us to lay people off or set us back by years.
If you rely on software, always have a disaster recovery (DR) plan and backups that are physically separated from the primary site. We’d have been toast without that. Today, if you use cloud IT services, don’t put all your eggs in one basket, and with newer threats like ransomware, your DR should read data from your primary system and use a totally separate set of credentials.
Based on your experience can you tell us what you did to bounce back?
Chandra Clarke: The number one thing that got us through was not finger-pointing or laying blame. We could have wasted a lot of time arguing, getting angry with our service provider, shouting at people not moving fast enough, and so on. Instead, we got on with fixing the problem. Even afterward, when we were doing a root cause analysis, we made it about doing better in the future.
Ok super. Here is the main question of our interview. What are your “Five Things You Need To Successfully Ride The Emotional Highs & Lows Of Being An Entrepreneur”? Please share a story or an example for each.
Chandra Clarke: The number one thing you need is self-care. I know that’s become a bit of a cliché, and I’m not talking about spa days and vacations in Maui — although if you can manage that in the startup phase of your business, go for it. But basics, like decent amounts of sleep, actual breaks from work, and regular meals. You tend to think you can get away with not looking after those things, especially when you’re young. You can’t.
Our worst days were, naturally, early on, when we were just starting out in business and when we had babies. In those “bad old days” I gave birth to our first child, had surgery, and ended up being back at my desk three days later because there was no one but me and Terry. Honestly, we were just blitzed most of that time, putting one foot in front of the other.
How do you find the time for self-care? Here’s the hard part: You have to ask for help. We entrepreneurs don’t like to admit when we need help. We’re doers! Problem solvers! We can do everything ourselves! That’s the road to crash and burn, though. Ask for help when you need it. Take it when offered, even if you think you don’t need it.
Terence Johnson: Next, I would say would be distance. As soon as you can afford it, get away from the business, even if it’s for a one-day conference for the business. The lows of business can feel very, very low when you’re nose deep in them. Being in a different location, away from your colleagues, can give you some much-needed perspective.
I remember being stuck on a programming issue for quite a while, and then I went away to a conference in a city three hours away. There’s just something about a whole different environment that jogs the brain. I came back with a solution, and several new ideas besides.
Chandra Clarke: Another thing that’s critical is a support network. It really, really helps to be to talk to other entrepreneurs at the same stage you’re at. My parents, for example, would often dismiss a concern I had about mounting expenses by saying, ‘oh, well, you can just write that off against taxes.’ Which kind of missed the problem of not having the money to pay for it in the first place! Other business people will be able to understand your pain, and maybe even share what worked for them.
Terence Johnson: I’m going to say that you need two support networks. One business-related and one not. The thing is, you can get completely wrapped up in your business, and that’s not healthy. So you also need people to talk to about other things. Other parents, fellow dog owners, that kind of thing. I remember feeling so much better when we finally started to have real free time, and I was able to take up model trains again. I had really missed my hobby.
Chandra Clarke: Finally, I would say the biggest thing that evened out the highs and lows for us was: hiring staff. We did everything ourselves for way, way too long.
For example, in the beginning, I was doing bookkeeping, as well as daily operations. I loathe bookkeeping. It’s detail work, and I’m not a detail-oriented person. I’m a systems and big picture person. Even knowing this, though, I’d beat myself up for not getting to it fast enough, for messing up as much as I did, and so on. When we first hired a bookkeeper, a major weight was lifted from my shoulders. We should have hired much earlier on. It would have freed us up for a bunch of higher-level stuff.
We are living during challenging times and resilience is critical during times like these. How would you define resilience? What do you believe are the characteristics or traits of resilient people?
Terence Johnson: Certainly having some perspective and a sense of history helps. For example, reading up on what people were like during the Spanish flu pandemic meant that I wasn’t terribly shocked or surprised at how things unfolded this time around.
Chandra Clarke: Having a good sense of why you’re doing what you’re doing also helps. Our café project has suffered endless delays and drastically inflated construction costs because of this pandemic. But we know that we’re filling a need in the community and that we’re building a ‘third place’ where people can chill in a safe, inclusive environment. That’s important, and that’s what sustains us when we get our contractor’s bills.
Did you have any experiences growing up that have contributed to building your resiliency? Would you mind sharing a story?
Terence Johnson: There are two kinds of resiliency. The “British stiff upper lip” kind only takes you so far. Understanding when to forge ahead and when to flex, learn from, or adapt to the situation is crucial — one that I picked up from Scouts, learning to navigate and sail small boats, and through volunteering alongside a wide range of people.
In your opinion, do you tend to keep a positive attitude during difficult situations? What helps you to do so?
Chandra Clarke: Most of the time, we do, I think. We help each other. When he’s feeling low, I’m the cheerleader and vice versa. It’s hard when we’re both in a funk, but fortunately, that doesn’t sync up too often.
Terence Johnson: When there seems to be a mountain in front of you, it helps to look back at the ones you’ve already climbed. I find it helps to talk things through, to see whether the apparently overwhelming problem can be broken down into smaller parts, or the apparently overwhelming to-do list reorganized.
Can you help articulate why a leader’s positive attitude can have a positive impact both on their clients and their team? Please share a story or example if you can.
Terence Johnson: Absolutely. The leader sets the tone and steers organizational culture. A leader who regards problems as problem-solving and learning opportunities are going to be a much more effective leader and have happier staff to boot.
Ok. Super. We are nearly done. What is your favorite inspirational quote that motivates you to pursue greatness? Can you share a story about how it was relevant to you in your own life?
Chandra Clarke: There’s a Steve Jobs quote that I love that I’ll share here. “…Life can be much broader once you discover one simple fact: Everything around you that you call life was made up by people that were no smarter than you. And you can change it, you can influence it… Once you learn that, you’ll never be the same again.”
I love that quote because it really frees up your thinking. I try to approach everything with that mindset.
How can our readers further follow you online?
Terence Johnson: You can ask for our book at your local indie bookstore, or at Amazon: Entrepreneurial Parent Business Family Sanity or Barnes and Noble: The entrepreneurial parent chandra clarke, and we’re also both on Twitter, @Terence_Johnson, and @chandraclarke respectively. We look forward to talking with you!
This was very inspiring. Thank you so much for the time you spent with
this. We wish you continued success and good health!
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