First struggle was to decide a good name for hosting company, can't really find a good .com or .net domain
Getting first 100 customers is the biggest trouble, we remember we paid for our first server without revenue at all for about 2 months and were in loss for about an year, but after 1 year we started growing and now after 2 years we have over 400 VPS customers, lots of web hosting clients
We even had lots of of problem as founders of our company are from India and could not get a good payment gateway in India and other problems, so first we setup company in Singapore and now recently moved to US