How to bootstrap and still scale your startup

I launched my first tech startup when I was 22. I was working in civil engineering by day, and coding on nights and weekends. I was both sales and development. I went full time at 25. I owned sales while my partner owned development. All of my initial sales — a bunch of $500-$5,000 web sites — were through friends and family connections.

While networking one day, I met an executive from a large hospitality company. I told her what I did, and she invited me to come meet with her about a project she was about to put out for proposals. Next thing you know, my partner and I are writing a 7-figure proposal. During the interview, the hospitality executive asked me why she should give us the business when Microsoft and IBM had given her very similar proposals. I was 25… I said “I don’t see their CEOs here! Must not be that important to them.”

I closed the deal a week later. It was not easy. For the next month, I almost lost the project every day. Procurement kicked my butt. I learned about payment terms, default-cure language, insurance, and more. It was a whole new world. I also learned how to negotiate beyond price, scope and schedule.

Entrepreneurs: in order for your startup to be a success, your first $1m in sales MUST be executed by a founder of the company. It can’t be delegated. The first $1m is critical — not just from a cash perspective, but as a learning experience.

With this in mind, here’s my simple method for scaling the sales process: