Original article on Baaz
Entrepreneurship is a turbulent adventure. One moment the wind is at your back, the next you are adrift on open water with no land in sight.
It is not for everyone. It calls for perseverance, a dash of luck, and a great deal of work. Blink, and suddenly ten years have passed. For Drillster and TOPdesk that is reality this year. The companies are festooning the office to celebrate 11 and 25 years of entrepreneurship respectively. It is the perfect moment to reflect on the journey so far. What have been the highlights, the setbacks, and—above all—the lessons they want to pass on to (aspiring) entrepreneurs? We asked Marco van Sterkenburg, CEO of Drillster, and Wolter Smit, CEO of TOPdesk.
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Drillster, the adaptive learning application for businesses, turns eleven this year. Founders Marco van Sterkenburg and Thomas Goossens saw firsthand how quickly knowledge slips away after a training session, course, or certification exam. Out of that frustration Drillster was born in 2011. They developed their own learning methodology that combines adaptive learning, microlearning, instant feedback, and question-led learning in a single tool. Thanks to timely reminders that prompt people to refresh knowledge, employees keep crucial expertise and competencies top of mind so they can perform with the right knowledge at the right moment. Marco reflects: “It feels like yesterday that we discussed building a smart learning app that would keep you up to date. I saw enormous potential for the corporate world. We secured our first investor, hired our first colleague, and got started. Step by step we kept building.”
Progress did not come overnight. “Those first years were true pioneering,” Marco recalls. “You are defining the market while figuring out how to shape your product. That made us very flexible, and at times less focused. Eventually you find the focus, and then you have to professionalise. It is not enough for the service and the product to be strong—everything around them has to be right as well. Early customers will forgive a startup the odd mistake, but as you grow, everything needs to work flawlessly. That is why we tightened our processes and procedures over time.”
Looking back on eleven years of entrepreneurship, Marco is proudest of the impact Drillster has had on organisations. “The greatest compliment is that companies now do what inspired us to start Drillster: they stop relying on periodic certification and testing. It is the ultimate proof that the tool and the methodology work. We have convinced major brands that occasional exams or refresher courses are not effective, whereas a continuous learning solution is. Seeing that become reality is incredibly rewarding.”
Service management provider TOPdesk is blowing out no fewer than 25 candles this year. The very first version of TOPdesk was built in 1993 in an attic in Delft. The idea came from Frank Droogsma. Fresh out of university, he worked at a help desk and saw how disorganised things could be. Drawing on his knowledge of the dBASE III+ database, he created something better. “That is when I entered the picture,” Wolter explains. “I had the programming experience to turn Frank’s idea into a production-ready product.” The result was TOPdesk 1.0: a DOS application that enabled smaller help desks to structure their work. Its unique feature was that it could be installed using just a few floppy disks—no heavy servers required. “Our goal was to help organisations deliver services in a smarter, better, and more straightforward way,” Wolter says. “That original idea still underpins the current version of TOPdesk: taming the complex chaos of a service department in an effective, pragmatic manner. It makes the work more enjoyable, and once one department adopts it, others usually follow.”
Over the past quarter century, TOPdesk has grown into a SaaS solution implemented worldwide. Wolter notes, “The most visible change has been our size. We now have 900 employees in eleven countries across four continents. I am proud that, even at that scale, we still maintain a strong, family-like culture.” What moves him most is when customers and employees come together. “I can keep enjoying our high customer ratings, but I get the same energy from seeing how engaged our colleagues are. Whenever that comes together at an event, it sends shivers down my spine.”
Entrepreneurship offers an abundance of special moments. That is why both Wolter and Marco find it hard to single out one highlight. “There are so many,” Wolter explains. “Visiting our international offices, hosting big events, or witnessing our growth time and time again. Reaching the summit is not what matters most to me. I genuinely enjoy the proverbial journey. It might sound a bit airy, but that is truly how it feels.” Marco’s favourite entrepreneurial memory goes back to the early years, when it first became tangible that Drillster was taking off. “The day we moved into our first office is still one of the best moments. We had been working on ideas for a while, but having a place of our own made it all very real.”
Entrepreneurship comes with ups and downs. Marco and Wolter have faced their fair share of the tougher side too. For Drillster, the early years required grit. “Funding was limited in the beginning,” Marco shares. “We were still building the product. On top of that, it was highly innovative. Adaptive learning was barely known, and for many companies it seemed a big leap compared to traditional learning. The reality was stubborn: the market simply was not ready yet. It took a long time to win customers and continue product development. At times our cash reserves were almost depleted. Those were tough moments.”
Wolter adds that entrepreneurship is not automatically fun. “It is a process of trial and error—and that is supposed to be enjoyable. You have an idea, you experiment, but not everything works. That is just part of the deal. What I found hardest was when people decided to leave the company. Your first thought is often that you have slipped back a few squares on the game board. Yet it is inevitable that some people will grow faster than the organisation itself.”
For both leaders, the lesson is to learn from the inevitable setbacks. With roughly 35 years of entrepreneurial experience between them, they have plenty of advice for (aspiring) founders. Marco says, “Who you build with matters. A team made up of people with identical skills or roles will not work. You cannot have six CEOs. A team of the same profiles eventually leads to conflict or friction. Surround yourself with complementary people so you head in the same direction and can strengthen one another.”
Wolter emphasises keeping joy in the journey. “Do not forget to have fun along the way. You only live once. It would be a shame to look back after achieving success and realise the ride was no fun at all. Entrepreneurship is fantastic. Do not hesitate to take the leap. Just know that things will not happen by themselves—and rarely as you initially envisioned. A healthy dose of perseverance and adaptability are your most important allies, especially at the start.” Marco adds, “If you have a strong idea and a clear vision, commit to it and stay the course. Do not let others throw you off balance. You will meet plenty of people with well-meant advice and their own ideas. Ultimately you must make your own decisions. Listen carefully to customers, scrutinise your product, but keep your own ambition and vision front and centre. If you do that, success will come—as long as you keep going all in.”
Want to read more about Drillster’s first decade? To mark the 10-year anniversary we published a book full of stories, interviews, and fun facts. You can download the book here for free.
https://drillster.com/nl/book-drillster-10-years-of-learning-with-you/
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