The Startup Playbook, 2nd Edition

Introduction

The fact that I (Will) was essentially bankrupt wasn't even the bad part. The bad part was I had to admit that my parents might have been right about what a stupid idea joining a startup was and, to add insult to injury, I had to ask if I could move back in with them.

You see, as a sophomore in college, I was so convinced that the startup path was right for me that, against my parent's pleadings, I quit school to join a fledgling company. As far as I could tell, everything was going incredibly well, and I'd made a great decision—until the day the company announced it was folding. What? It didn't make sense. And, to make matters worse, no one could explain what caused the meltdown. It wasn't even clear if anyone really knew.

Despite the failure and with no idea why the company crashed and burned, I thought I could do better. So, I acquired some of the assets from the failed company and created my own startup, DataWare Logic. I was sure I'd find success where the last company hadn't.

It didn't turn out well. In eighteen months, the new company was dead, and I went home with my tail between my legs.

After two failed startups, I still had no idea what had gone wrong or how either unraveled. There were customers, computers, and contracts, but no more cash. Not only was there no one to ask—I didn't know anyone who had even tried a startup—but I didn't even know what to ask. I had no wisdom, no knowledge, and no help.

Starting a Company Is Easy. Starting a Sustainable, ...