Canadian Entrepreneur . Lean Startup . Technical Founder . Marketlike.co . Toronto Based-startup . MaRS Innovation Client
I've bootstrapped a startup and built a solid social marketplace platform from the ground up with budget just under $5K which would've cost me $15K to build locally.
Having a strong technical background is both a curse and a blessing as an entrepreneur. It's only a blessing if you know how to use it. I worked as a programmer for outstanding companies for 4 years and had been working part time as an entrepreneur half of time until I decided to jump off the cliff and build my own dream. Even though I thought I knew everything about lean startup, the first 5 months of being an entrepreneur was not productive because I still had my programmer's mindset. So if you have the same background as I am, and looking to be an entrepreneur.. Please don't make the same mistakes as I did.
Based on my experience, the biggest challenge is getting the right talent that can pull off a quality work, I have done this by sending out small tasks to different developers and evaluate their works after. (But I guess this isn't your issue since you have 4 yours experience of working together). The next challenge I faced was time difference. Both parties need to be flexible enough with their schedule meaning working in the evening to get things resolved right away. Exchanging email with hours/one-day-delay to reply kills the momentum and motivations.
Let me know if you would love to get more information about my experience with outsourcing.