It’s Entrepreneurs’ Day – Interview with Ingvar Gudmundsson and Rut Steinsen – Founder and CEO of SimplyBook.me

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Today, we celebrate those with an entrepreneurial spirit – successful or not. It’s Entrepreneur’s Day, so we are interviewing our closest entrepreneurs, our founder, Ingvar Gudmundsson, and our CEO, Rut Steinsen.

The Story of Simplybook.me is freely available on our website, but we (make that “I”) thought it was a great time to find out more about the people behind the software. Creative thinkers, idealists, and driven and successful individuals are much more than their business acumen and job titles. 

Perhaps that’s the reason for SimplyBook.me being one of the best appointment booking systems worldwide. It takes more than business skills and a great idea to make a business thrive. Maybe, it takes entrepreneurs with imagination, compassion, and sticking to their ideals to work. I’m sure we’ll find out in our interview.

A Brief History of SimplyBook.me

The idea for SimplyBook.me began slowly, with a request from a business requesting booking software. It wasn’t difficult to see the benefits this software would have for thousands of other service businesses worldwide. So 2009 saw the birth of SimplyBook.me. 

In 2011, there were some significant breakthroughs concerning the name, branding and registration process. So they launched SimplyBook.me with its current name and a much-simplified registration process.

Technical bloggers worldwide soon started praising this simple appointment scheduling solution. This brought more visits, new sign-ups, link authority, and higher Google ranking and referrals.

The core of the SimplyBook.me product has always been the robust booking engine. But over the intervening years, so much functionality has been added to make it a customisable system to fit virtually any service business. 

Today, SimplyBook.me is one of the most successful online appointment scheduling software services on the market. They sign up thousands of new users every single month.

The Interview…

The interview with Rut and Ingvar was so full of priceless information we decided to split things up for better comprehension and to separate their different approaches to the building and development of SimplyBook.me. Both are powerful entrepreneurs, and their combined approach to SimplyBook.me is collaboration in poetic motion.

Ingvar Gudmundsson, Founder of SimplyBook.me & VP of Sales

Yes, he has two titles, not least because he is still very involved with company development but also because you can start a business, but you have to keep doing something as the company grows. However, Ingvar is so much more than a sales guy. He is a driving force behind product development and generating new ideas.

So, try to describe yourself in three words

Positive, Creative, Persistent

What was your key driving force to becoming an entrepreneur?

I have always been an entrepreneur and dreamer. This may be because I used to read a lot which seeds the imagination part of the brain. At a young age, my ideas were a bit crazy, like creating planes out of wood boxes, but fortunately, they became more reasonable with age. I have created and launched multiple projects through the years with SimplyBook.me being by far the most notable one.

Where did the idea for SimplyBook.me originate?

When we created it first, it was for a small company in Iceland, but we felt that many more would be able to use it, so we launched it as a SaaS in 2009. We didn’t get a lot of traction, only a few paying users, but enough to keep us dreaming. In 2011 we changed the name to SimplyBook.me, and since then, we have been growing nicely.

After more than 10 years of growth and development, what is next for SimplyBook.me? Where do you see the business in 1 year, 5 years, or 10 years?

We are already developing several side projects that support SimplyBook.me and can also work as stand-alone projects. I see us continue to grow worldwide and make users happy with a solid, secure system they can trust to help them run their businesses and increase their revenues.

How do you generate new ideas for SimplyBook.me and the growing number of brands in the same family?

We are very product driven and listen to users as well as using our own intuition. We try to figure out what is going on in the tech world and add new stuff accordingly. For example, we started accepting bitcoins in 2011, which made us lots of money since we never used them. We also launched a speaking bot many years ago, ready to accept voice bookings. Unfortunately, new stuff has no guarantee of success, so the bot, for example, was a failure, and almost no one was interested in using it. It was strange. We thought everyone would love it, but that’s life. You can’t count on anything.

At what point did you look at your business and consider it a success?

I am not sure there is any such time for any business, well maybe a few, but for most, it is not so. Look at FTX, the huge bitcoin exchange valued at tens of billions of dollars that then went bust in a moment. It shows that every day is just a new day to invent and fight, and never to look at it like it is a success or finished.

What best motivates you? How have your entrepreneurial motivations changed since you first started?

Getting ideas into action. Unfortunately, this can be restrained by “production capacity”, so I have to hold off a lot with my ideas. Then again, this gives some time to reflect more and determine if they are good or not.

How does your business look different now vs when you first started?

The biggest difference is that we have much better protocols for everything, and I am no longer involved in everything that happens, which is very good.

What would you change about your business journey if you could go back?

We have always been very careful in running the business, so we have normally hired at a pace that we are 100% certain of being able to sustain. Knowing what I know today, we could have hired a bit more aggressively early on for faster production.

What would you now advise your young entrepreneur self when you started?

Build a good team early on and have confidence in future revenues to hire even more aggressively to grow even faster. Definitely try to build a team concentrated in one office or only in very few office clusters. Allow members to work from home, but with requirements to come to the office regularly to meet up.

What popular entrepreneurial advice do you agree/ disagree with? Why?

Never give up! Sometimes you have to know when something isn’t working and learn to let go or pivot.

How would you rank the key 5 skills needed to be a successful entrepreneur?

• Perseverance
• Good communication
• Efficiency
• Decisive
• Good mood/happiness

To achieve the above, good sleep is a must, and for good sleep and a good mood, exercising is a must.

Are there any missed opportunities that you wish you had leveraged?

I programmed a software called Logiledger back in 2002, which was an online accounting software.  I know now that Xero was established in 2006 and Freshbooks in 2003, so I was definitely on to something there.  But I didn’t try to get funding to take it all the way, which is a shame in hindsight as it was a great idea and the software was actually very good, even though I say so myself. The software was mainly used by companies in Iceland and got some hundreds of active clients.

Do you believe there is a winning formula for becoming a successful entrepreneur? What is yours?

There is no simple winning formula for anyone because success is a mix of a good product, the right timing and a bit of luck. 

Who is the one entrepreneur to be your greatest example and inspiration?

In fact, there is no one special, it may be to my disadvantage that I am not a big reader of some success books of other entrepreneurs, but I do read a lot of financial news where there are often some interviews with various entrepreneurs. They can often be inspiring, but not to the point that I am awestruck in some way or another.

What sacrifices have you had to make to be a successful entrepreneur?

I have been quite lucky in the sense that I have not made any decisions in my personal life that I have had to regret hence I can not talk about sacrifices in that sense. I have a good work/life balance and have kept that for most of my life.

What was the toughest moment you have experienced in your business practice? How did you succeed in getting over it and moving forward?

The toughest moments must have been in 2008 when the whole bank system of Iceland collapsed, and we lost almost all of our clientele. I had to let go of half the team but managed to keep the rest by working for other companies to have income for paying salaries while we got it going again. It was a tough time, but it made us do new things and is the reason where we are today.

What would you advise young entrepreneurs starting out an idea?

This depends very much on the idea. If it was a bad idea, I would probably just tell them to go work somewhere, get more experience, and see if they can come up with a good idea later. For those with great ideas, I would suggest finding good team members, going for it, and being prepared for hard times.

What would you name it if you were to write a book about yourself?

Live each day, no regrets!

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Rut Steinsen – CEO

You only need one title when you carry as much responsibility as Rut does for the smooth running of SimplyBook.me.

So, try to describe yourself in three words

Competitive, Optimistic, Energetic

(I completely agree with all three of these, from our brief 3-and-a-half-year acquaintance 🙂 )

Considering the fierce competition in today’s business world, how would you highlight SimplyBook.me’s competitive advantages? What makes it stand out of the crowd?

We have a whole lot of competitors, both local and international. I would say that our system stands out for three things:

• We provide businesses with a really professional and customisable booking website
• Businesses can choose from over 60 features, enable the ones that fit their business and pay accordingly
• We offer the best Live Chat in the market, with our agents being online 24h during the working week with 9 seconds average response time.

What are your hidden inspiration sources?

I mostly get inspired by either listening to podcasts where entrepreneurs and business specialists are talking about their experiences and results or by analyzing what our competitors are doing and seeing what we want to do better.

What will you never compromise on with your business?

As a leader, I would say my integrity. I try to set my core values in life that apply to our business, too and have those guide me. In terms of the business, our employees’ well-being is always a priority and secondly, to make sure we run the company in compliance with all regulations.  

We want to manage our employees’ workload so that they can maintain a good work-life balance and thereby become long-term happy employees.

How does your typical working day look? 

Wake up at 7:30 and sleepwalk to the coffee machine for that first cup of coffee. 

Drop my son off at school at 8 am and then start working after that.  Usually, I start by going through emails, checking for chats and looking at stats from the day before. 

Then after that, the tasks can vary greatly, whether that is to discuss upcoming features, chat about marketing activities, have a product meeting etc. 

At lunchtime, I play tennis for an hour, which I absolutely love as it kind of resets the day.  Then I come back, take a quick shower and have lunch by the computer as I start working again. 

The working day then usually ends around 18:00, and I start preparing dinner as I enjoy cooking for the family.  In the evenings, I either chill at home with the family watching TV or playing the piano. Otherwise, I’ll meet some girlfriends for golf simulators, movies or cosy chitchats.  I am usually in bed between 22:00-23:00 and try to be asleep before 23:00 to get my 8 hours of sleep!

How do you define success or failure?

While you are running a company, you don’t define whether your business is successful or not.  I mean, obviously, you want to run your business on the right side of the zero:)  But in my mind, I consider it a success knowing that 50 people choose to work with us. If those people feel happy working for SimplyBook.me, feel they can contribute, work independently, are listened to, look forward to going to work and can maintain a good life-work balance, then that is what I consider success.

What are your milestones in creating a stable company culture and friendly working atmosphere?

We have always kept three milestones in mind from the outset:

• Flat company culture – everybody can contribute.
• Possibility to grow within the company – retain great talents.
• Culture of independence where we trust our people to do their job well.

Top 3 places on the globe that you haven’t conquered yet but would love to?

Since we are based here in Limassol, we would love to conquer Cyprus as we believe that the market is underdeveloped regarding online bookings!

Then we are very much trying to enforce our position in the French and the German market as we believe that they are ready now for appointment scheduling taking over their service businesses.

What’s your personal method for balancing work and life?

I try not to sit by the computer in the evenings, to give myself a total screen rest after work.  Of course, something might come up, but I usually do pretty well in managing the balance in a normal working week. 

It also really helps to do some sports or play the piano if I need to clear my mind. Both playing tennis and the piano are extremely difficult if I try to think of work at the same time:)

What takes you out of your comfort zone? What are your ways of handling these situations?

We all get stressed when we need to do something that is out of the ordinary, like presenting to an important crowd, taking important calls etc.  For me, it always works best to prepare well, and then I do well even though I might feel stressed in the midst of it…but usually, that has worked well.

What is the one issue about your life experience you would alter if you had the chance to?

I really do not focus too much on the past, but of course, it is easy to think about business decisions in the past that one should have made differently now when you know how the market evolved.

What do you consider to be your weaknesses?  

Lack of tech and programming skills. It can be frustrating not knowing better what is needed to implement new features/changes. 

What advice would you give your 20-yr-old self, knowing what you know now?

Don´t take life too seriously.  If you always give it your 100% best, everything will turn out just fine.   We only live once. We should do what we do well, but at the same time, enjoy the ride. Appreciate our health, admire all the beautiful things life has to offer with its nature and first and foremost, nurture the relationships with friends and family well. Those are the things that really matter in our lives forever.

What lessons have you learned from your failures?

Not to overthink.  Not to get too stressed when you are dealing with people in higher positions.  At the end of the day, we are all the same kind of creatures here on this earth, and most of the time, people are friendly and polite irrespective of their position.  Prepare well, and you will be fine.

What would you name it if you were to write a book about yourself?

What a ride!

Altogether Now!

The different approaches and complementary skill sets between both of these incredible people enable this company to work well and develop.

It takes a delicate balance of skills and cooperation to merge the power of ideas and the control of minutia, and these two blend perfectly.