Iværksætterhistorier’s Esben Brandborg Østerby: “Follow the high school party principal”

On his podcast, Iværksætterhistorier (Entrepreneurial Stories), Esben Brandborg Østerby interviews Danish entrepreneurs about the journeys behind their ventures. Østerby told ARYZE about how he became a podcaster, what he has learned about entrepreneurship, and some of his favourite stories about Danish start-ups.

When I approached Esben Brandborg Østerby in the hallway of ARYZE’s shared office space to ask for an interview, it was only after he cheerily agreed that he asked, “Who are you?”  During our conversation, his enthusiasm for entrepreneurship was tangible – a good thing, seeing as his job is to interview Danish entrepreneurs about their ideas, roadblocks and successes.

Østerby, who now goes by the acronym Mr. Podcast Pippi, did not create the Iværksætterhistorier podcast, but rather started as a fan. When the original host lacked the time necessary for the show, Østerby reached out to see if he could be of any help. He decided to get involved, starting as a co-host and, eventually, taking over the show. 

He loves his job because of what he calls the “high school party principle” – which he has taken from famous entrepreneur Gary Vaynerchuk – the idea that if you can invite cool, smart people to something interesting, they’ll be more likely to make time to hang out with you. Østerby says: 

“Let’s say you are a freshman in high school and you want to hang out with the cool seniors. If you just say ‘Can I come to your party’, you won’t succeed. But if you make your own original event and make that popular, they’re way more likely to join you.”

Iværksætterhistorier’s Esben Brandborg Østerby

This is especially true when that event adds value for them. He believes that by appealing to their narcissistic side – by inviting them to make a speech, give advice, or, in his case, speak on a podcast – you can easily build relationships with inspiring people:

“We are all little narcissists inside: we all want to share our own opinions, values, stories and knowledge. You have to make them the expert – cause who doesn’t want to be the expert!” 

Østerby has learned a lot from doing just that, and now has much to say about the start-up scene, particularly in Denmark. Østerby believes that Danish startups and scale-ups face different challenges than those in other places. He thinks that while funding at any stage is indeed possible, the Danish ecosystem lacks the mindset of big international scaling:

“I believe it’s most likely grounded in our culture. We lack the American dream mindset. We are simply not taught to think big from childhood and that is a problem. However, public interest in entrepreneurship is, fortunately, increasing. One reason is because the Danish Foundation for Entrepreneurship works closely with educational institutions in all stages to secure more innovation courses. Another is the popularity of national TV shows like ‘Løvens hule’ (The Danish version of Shark Tank). We still have a long way to go, though.

Read about the stories at Iværksætterhistorier and listen on Spotify, Apple Podcast or wherever you get your podcasts here.

Although Danish entrepreneurs benefit greatly from low barriers to company creation, high access to mentorships, meaningful government support, and myriad networking opportunities, Østerby believes that there is a big gap between the amount of publicity focused on entrepreneurship and the number of people that actually start their own companies:

“The numbers speak for themselves. We’ve seen a significant decrease in new companies created, as there has been an 18% dropdown compared to last quarter.”

Despite warning that “there is no one piece of advice because every case is different”, Østerby believes it is important to focus on sales rather than product. Developing a product is, of course, extremely important. However, if entrepreneurs cannot sell – first their idea to investors and later their product to consumers – then there is little chance they will succeed. As a part of selling, Østerby highlighted the importance of transparency; entrepreneurs must fight the urge to protect their company behind NDAs and should instead spread their message as far as possible. For this reason, content production is key: 

“We scroll ninety meters per day on social media; you’ve got to be in that feed, and people love transparency.”

The more people who know about an idea, the more feedback entrepreneurs can get, and, therefore, the better they can be. On that line, Østerby says, networking is key – and entrepreneurs should be persistent. His philosophy: 

“If people don’t have time now, that doesn’t mean they won’t have time later, so keep trying”. 

He argues that it is important for entrepreneurs to send personalised messages explaining why they want to make the connection. Just connecting on LinkedIn is the digital equivalent of handing out business cards to strangers: it is not enough. 

Østerby highlighted the key difference between advice and mentorship: 

“Just because people give you support, it doesn’t mean they believe in you. Your close friends and family aren’t your allies. Often they don’t understand your chosen path, but they don’t want to let you down, so they clap you on the shoulders and cheer for you, but honest feedback is critical. It is important to find mentors that know who you are, your background, and how you work, but who can give you the right push.”

He argues that it is important to know your company’s values to sift through the advice. 

“You need one-hundred bad pieces of advice to get one good one. Advice is free, but you need to have your own mindset and filter that inspiration into the context of who you are.” 

Ironically, he added, “but don’t take my word for it!”

Similarly, it is important to know your strengths and weaknesses as an entrepreneur, and to find partners that will complement those skills. 

Østerby’s favorite start-ups? “There are so many. So, so many.” 

One favorite is Greenspeak, a Danish mobile company that donates 100% of its profits to a charity chosen by its users. No one in the company earns more than 30,000 DKK per month, and if you call them, their director himself will answer.

Østerby also listed ZliideTechnology, an omni-channel, app-based self-checkout service for retail stores. The company had a rocky start that nearly ruined them: their founders came extremely close to signing away 50% of their company to a rich fisherman. They were only nineteen at the time, and are now thrilled and relieved that they held out for a more advantageous funding stream and a greater capitalization table. 

Yet another favorite startup story of Østerby’s is that of AirHelp, a company which advocates for air passenger’s rights when their flights are delayed, cancelled or overbooked. In its early days, the startup invested all their money into attending the world’s most prestigious accelerator program, Y Combinator in San Francisco. The investors told them that if they received an email, they did not get the investment, but a phone call would mean good news. The meeting did not go well, and the founders went out drinking tequila for hours waiting for their result. When they finally heard back, it was in the form of an email. Disappointment, they opened it only to read: “What is your phone number?”

These examples only scratch the surface of the innovative and exciting entrepreneurial stories that Østerby has to tell. To learn more about Danish startups and the stories that made them, please visit the Iværksætterhistorier website. For more insights into entrepreneurship, visit ARYZE’s blog

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