Startupland

"Building a start-up is like jumping off a cliff and assembling the airplane on the way down." This book shows you how to take that leap without falling flat.

1. Your first start-up doesn’t have to be your last.

Starting a business is a journey filled with experimentation and learning. The author, Mikkel Svane, spent years trying various ideas before his eventual success with Zendesk. Early on, he ventured into 3D illusions based on 2D patterns, later transitioning into website development. These projects helped him understand the practical challenges of running a business, even as some failed.

One of Svane’s major lessons was realizing that truly great ideas often appear unexciting at first. The idea for Zendesk—a tool for helping businesses manage customer support—didn’t seem revolutionary to many around him. Even one of his core team members, Alex Aghassipour, was initially unimpressed, calling it “boring.” But Svane knew execution was what would make the idea impactful, much like how Dropbox made mundane file-sharing simple and fun.

Embracing failure and constantly iterating is key for entrepreneurs. Every unsuccessful venture adds to your pool of knowledge. Instead of being paralyzed by the fear of failure, founders should view each attempt as a stepping stone.

Examples

• Svane’s 3D illusion business taught him self-reliance, as he handled orders and logistics solo.
• The dot-com crash wiped out Svane’s web development project but prepared him for future crises.
• Dropbox’s success as an initially “boring” idea affirmed to Svane the value of execution.

2. Choosing the right investors matters more than choosing any investors.

In the rush to secure investment, many start-ups make the mistake of partnering with the first investor they can find. However, not all investors have your company’s best interests at heart. Svane learned this when his first angel investor tried to manipulate the Zendesk team by demanding endless paperwork, knowing they were desperate for funds.

When traditional investors proved problematic, Svane turned to friends and family to fund Zendesk’s early days. While asking loved ones for money was difficult, it resulted in much-needed capital without strings attached. One such connection even led to an unexpected $30,000 contribution from a colleague’s boss.

Later, after Zendesk had secured required funds, Svane jumped at an additional investment offer from an experienced angel investor. This move not only boosted their finance but also brought in valuable expertise, showing that building relationships over time is equally important as the investment itself.

Examples

• An early investor pressured Svane with delays and demands to gain leverage.
• Friends and family provided funding when more traditional sources seemed uninterested, keeping Zendesk afloat.
• Accepting an additional angel investment gave Zendesk the means to scale ambitiously.

3. A strong team is the backbone of your start-up.

Building and maintaining a great team can make or break a start-up. Svane emphasizes the importance of teamwork by recounting how Zendesk’s three founding members struggled but stuck together during challenging times. They were all working without pay, which tested their commitment to the vision. Svane even offered a small salary to one partner to keep morale and focus high.

Conflicts are inevitable in the high-pressure world of start-ups. For instance, tension arose when selling company shares meant the founders would lose majority control, leading to heated arguments and emotional strain. Yet, by staying aligned with their larger goal, the team overcame these struggles.

Like in team sports, the spirit of camaraderie within a start-up deeply influences outcomes. It’s not just about individuals contributing their skills; it’s also about trust, perseverance, and collective problem-solving.

Examples

• Sacrificing his personal finances, Svane paid one teammate a salary to keep him motivated.
• The team survived heated disagreements regarding the sale of company shares.
• Playing to each founder’s unique strengths kept Zendesk moving forward even in hard times.

4. The U.S. offers unparalleled opportunities for start-ups.

If you’re serious about making it big with your start-up, location matters—a lot. Svane attributes much of Zendesk’s success to its strategic move from Copenhagen to the United States. American culture, especially in tech hubs like San Francisco, thrives on optimism, risk-taking, and community. This environment encourages innovation.

Svane recounts attending a TechCrunch event in San Francisco, where he discovered nearly everyone was either familiar with Zendesk or using it themselves. This kind of exposure and concentration of talent would’ve been impossible in Denmark. The pooling of investors, tech innovators, and accessible markets made the U.S. the perfect launchpad for the company’s growth.

While relocating wasn’t easy, with logistical challenges and cultural differences to navigate, it was ultimately worth it. The move not only opened doors to more opportunities but also immersed the team in a thriving start-up culture.

Examples

• Denmark had limited internet adoption in the 1990s, contrasting with early U.S. internet enthusiasm.
• TechCrunch in San Francisco highlighted Svanes’s realization about community and visibility in the U.S.
• Relocating from Boston to San Francisco brought Zendesk a $6 million investment from Benchmark.

5. Start-ups impact families deeply.

Entrepreneurship doesn’t just affect the founder—it ripples through their entire family. Svane experienced immense financial stress while building Zendesk, pushing his credit card debt and even dipping into retirement savings. To avoid worrying his partner, Mie, he didn’t disclose the full extent of their precarious financial situation.

Frequent relocations for the business added more strain. Moving from Denmark to Boston and then to San Francisco meant uprooting his family from their comforts multiple times within a short span. Each move brought unique challenges, from broken air conditioners to accidental lockouts during chaotic early days.

Balancing family and start-up life isn’t easy, but it’s an essential lesson for entrepreneurs. Communication and resilience both within households and in business play a big role during turbulent phases.

Examples

• Svane used a $50,000 loan and maxed out credit cards to keep Zendesk afloat.
• The move to Boston involved personal discomfort, such as enduring a summer without air conditioning.
• The San Francisco relocation happened abruptly but was vital for Zendesk’s growth.

6. Recruiting requires adaptability and creativity.

Hiring the right people can be complicated, especially in a new country. Svane realized quickly that Danish humility was vastly different from American confidence. Where Danes downplay their strengths, Americans often assert their capabilities with boldness. This cultural difference initially puzzled the team during interviews in Boston.

To spot real talent amidst a sea of applicants, the team designed unique evaluations. For example, one HR recruiter would intentionally walk fast to gauge adaptability and attentiveness in potential hires. They also asked unconventional questions about travel experiences and life challenges rather than focusing solely on education.

These methods helped Zendesk select individuals who genuinely fit the company’s mindset and culture, a critical step for any start-up scaling rapidly.

Examples

• A candidate was assessed on how they reacted to speed-walking and splitting café bills.
• Zendesk recruiters avoided conventional hiring questions to target problem-solvers.
• Observing personality in non-traditional settings helped identify adaptable hires.

7. Mistakes are part of the process.

Every start-up stumbles. Svane made his share of errors in Zendesk’s early days, including an ill-timed pitch to investors during the 2008 financial crisis. Unsurprisingly, the deal fell through due to economic instability, teaching Svane that timing was as important as having a good idea.

Another misstep came in the form of underestimating employee needs. New hires arrived unprepared for quitstart-up norms, which left a poor impression on some valuable recruits. These moments emphasized the importance of internal processes like onboarding even at a small scale.

The toughest lesson came from customer backlash when Zendesk increased prices without explaining the move. The outrage tarnished their reputation online until the team publicly apologized and reversed the decision.

Examples

• The 2008 crisis derailed an early investment meeting in the U.S.
• Amanda Kleha’s skepticism about not receiving a computer on day one highlighted gaps in onboarding.
• A poor communication strategy about pricing changes led to customer dissatisfaction.

Takeaways

1. Treat early failures as learning experiences rather than roadblocks to success.
2. Focus on building a strong, supportive team that shares your long-term vision.
3. Always communicate openly—whether with investors, customers, or family—during chaotic periods.