Five Biggest Challenges a Start-Up Founder Will Face During the First Year

2 years ago . 4 min read
Five Biggest Challenges a Start-Up Founder Will Face During the First Year

It was 2:00 a.m. when my alarm rang. I had slept for only three hours because I needed to catch my flight to Yogyakarta to visit my start-up branch office. Before I went to sleep, I had a difficult discussion with my dad. He asked me to quit my business because it has no future and instead help him with his business. When I arrived in Yogyakarta, I was very tired because I had slept, on average, for only four hours a night that week. However, I still needed to lead a meeting with my team, so I tried to be energetic. This challenging situation continued for the first year of my start-up. In retrospect, it was my passion to create an Indonesian technology company that can rise globally that pushed me onward. From early harsh hurdles I lead my start-up, Nusantara Technology to be the first Indonesian technology start-up in SaaS and online media to join Y-Combinator Winter 2018, the most selective American incubator that funds start-ups and has helped build a number of highly successful companies like AirBnB, and Dropbox.

I would argue that being a start-up founder is one of the hardest jobs. The first year of a start-up is the most difficult because the start-up founder may face an unsupportive family; sweat equity, and long work hours. A start-up founder will fail nine times out of ten and face never-ending challenges and milestones.

1. An Unsupportive Family

Oftentimes, families will not support the founder’s decision to start a new company because the company is not guaranteed to succeed. During my first year leading Nusantara Technology, that period was one of the most difficult times in my life: the business was brand new and was slow to gain traction, and I needed to convince my family that my start-up could be successful.

2. Sweat Equity

Start-up founders use their first year’s profits to invest in products and the company's growth. Personally, I did not take a salary during the first year of building Nusantara Technology. I used my personal savings to live modestly, and my cofounders took a very small salary. We needed to continually reinvest in our start-up, and find a product market fit. It was not until the second year, when we closed our “Series A” investment and the business started to show a profit, that we earned a proper living wage.

3. Long Work Hours

The pace is intense and the start-up founder works hard, but the job is never done. Typically, start-up founders will have many sleepless nights due to workload and stress. I still remember once, one of our clients asked us to create an advertising campaign on our two sites ( and in 3 days and over a weekend. We decided to accept the project; we worked day and night for 3 days to deliver the product to our client.

4. Start-Up Founders Will Fail Nine Times out of Ten

Start-up founders are going to fail the majority of the time. There are two types of failures: product failure and rejection.

Every time we release a new feature on,, or, we will most likely face obstacles and failures. We completed over 50 trials to ensure the right advertising on our site and the right formula. Our goal is to deliver the best advertising campaign to our clients.

Besides product development failures, there are client acquisition challenges. During the early days, nine out of ten prospective clients rejected us.

5. Never-Ending Milestones

One should never assume that start-up founders have sufficient funding the job will be easier. The challenges will be harder.

Nusantara Technology cofounders realized that we took on more responsibility when we raised more money. Today, we work harder than when we had raised our first investment. Our goals are even tougher to achieve.

Therefore, before starting a company, you should ask yourself whether your dream is an obsession or whether it is driven by materialistic desires. Additionally, can you overcome these five challenges? If you can, your career—and your start-up—will most likely thrive. However, the chance of a start-up succeeding is slim, so you will need to be both passionate and lucky.

Steven Wongsoredjo is the Co-Founder and CEO of Nusantara Technology, a technology and media group created by Indonesians for the younger generation. Nusantara is also the second Indonesian startup company accepted into Y Combinator.

Written By
Steven Wongsoredjo