
In this BlackBird podcast, host Andy Coomans interviews Jo Deferm, who started online surf-travel company BoardX around 2000 and grew it to ~5,000 young travellers and 120 monitors per summer before selling his stake after 12 years when the passion turned into stress. He then co-founded marketing agency Content Crackers, which grew fast to 16 people but served everyone from bakers to bpost and Carrefour; with external guidance the partners made the hard call to shut the brand down and relaunch as Webhero, focused exclusively on affordable digital services for freelancers and small businesses. That pivot meant abandoning 70% of the business, reinvesting personally and bringing a silent investor on board, and took two to three years to become cash-positive. Recently Webhero acquired the client base of a bankrupt competitor in a four-week deal — taking over the trade fund without contracts — retaining roughly half of the ~230 clients, and Jo now sees selective acquisitions as an interesting growth lever. He also discusses radical transparency: publishing an annual report including failures and sharing real-time figures with his team and investor.
Jo Deferm's thinking centers on a hard-won distinction between gut instinct and structure, and he is unusually candid about how long it took him to make that shift. "Ik denk dat de eerste 10, 15 jaar van ondernemerschap het meer gewoon op buikgevoel was," he says, adding flatly that "alle beslissingen werden op buikgevoel genomen" 3. Only in the last five years did he bring in coaches and consultants to hold up a mirror and help him see his own strengths and weaknesses 3. This is not false modesty: he traces a direct line from that early, instinct-only period to becoming the bottleneck in his own companies, both at BoardX and later at Content Crackers, because he never cleanly separated the roles of owner, manager and entrepreneur, which he now sees as the core structural mistake of most SMEs 2.
The BoardX story is his clearest illustration that growth and personal wellbeing are not the same thing. He didn't sell his stake because the surf-camp travel business was failing, it was still very successful, but because he had lost grip on a 130-person seasonal organization and, in his words, his energy and "goesting" were simply gone 3. Selling was a relief, not a target reached. This experience shaped a broader conviction that runs through everything he says afterward: company growth does not automatically make the entrepreneur happier, happiness is a function of life stage, pressure and personal fit rather than revenue 3. When he later describes the emotional cost of running an agency for years, the same logic surfaces again: "na vijf jaar kunt gij een koffiekoek niet meer," he says of Content Crackers, and once he stepped away from that grind, "dat was echt 10.000 kilo van de schouders" 2.
The pivot from Content Crackers to Webhero is the centerpiece of his entrepreneurial philosophy, and he describes it almost as an act of controlled destruction. Killing the Content Crackers brand meant giving up 70 percent of the existing business and required fresh capital, partners reinvesting plus a new investor, to survive two to three years of cash burn before the new model turned positive 2. He kept the whole team but shifted everyone overnight from client project work onto a single product, new roles from one day to the next, and calls it their best decision ever: "dat moment was de beste beslissing die we sowieso genomen" 3. He is explicit that this required nerve more than certainty: "Ge moet durven springen en soms denk ik wel van: we springen gewoon en we lossen het wel op" 2. In hindsight, he singles out branding as the most underestimated lever in a pivot like this, arguing that building the Webhero brand itself was one of the best investments of the whole transition 2.
He is just as deliberate about the mechanics that keep him and his partners honest. With a silent investor, alignment comes from radical transparency, a full shareholder agreement plus a shared real-time dashboard of the company's figures, rather than informal trust 2. Publicly publishing yearly targets and results, including the years he missed them, is something he treats as a discipline rather than a risk: it forces accountability because you cannot quietly lower a number you have already written down 3. He extends the same logic to people around him personally, saying he has made "een sport" of telling the right people what he is going to do, precisely because "die mensen houden mij accountable" 2.
On clients and growth strategy, his views are pragmatic and somewhat contrarian. Big-brand agency clients look impressive on a website, he says, but in practice they consume roughly 30 percent of capacity on pitches, carry 90-day payment terms and are difficult to work with, whereas small clients deliver higher impact and recurring, risk-spread revenue 2. This is tied to a philosophy about lock-in: Webhero deliberately works without long-term contracts, billing clients per year, betting that value delivered rather than contractual lock-in is what keeps people, and he notes that churned clients often come back 2. Because the target group is freelancers and small businesses at affordable pricing, he treats operational discipline as non-negotiable, staying affordable only works if operations avoid what he calls "bokkensprongen," erratic one-off exceptions that quietly erode margins and consistency 3.
The bankruptcy acquisition that grew Webhero shows the same appetite for speed balanced against real caution. The whole deal moved in about four weeks from the curator's first call, leaving no room for proper due diligence, so he limited risk by buying only the trade fund rather than shares or contracts 2. He is self-critical about the human side of that deal, admitting that communicating the takeover to the roughly 230 acquired clients too abruptly was a mistake, some felt rescued while others learned of the bankruptcy only through the announcement itself, and a softer transition would have served everyone better 2.
Underneath all of this sits a belief that entrepreneurship is a baseline set of literacies, not a personality trait. He argues plainly that "als ondernemer moet je... een beetje boekhouding kennen om te ondernemen," and that a working knowledge of digital marketing belongs in that same basic toolkit 3, while also insisting that knowledge only matters once it is applied: "Ge kunt veel boeken lezen, maar ge moet het nog wel omzetten in de praktijk natuurlijk" 2. His own admission, borrowed half-jokingly from his mother, that he carries "een lichte vorm van grootheidswaanzin" 3, reads less as bravado than as an honest account of the temperament needed to keep jumping into pivots, acquisitions and public targets without a guaranteed landing.
From public career histories · 14 entries
Jo Deferm tells how he went from running surf-camp travel company BoardX (5,000 youths/summer) to killing his agency Content Crackers and rebuilding it as Webhero, a one-stop digital partner for small businesses that now grows organically and via a first acquisition out of bankruptcy.
Serial entrepreneur Jo Deferm (Webhero, ex-BoardX, Content Crackers) explains how he evolved from pure gut-feeling entrepreneurship to structured, coached growth, why he sold his successful surf-travel company after losing all energy, and how pivoting a €500-website side project into a SaaS product became his best decision ever.