Table of Contents

Introduction

Introduction: The First Rule of Holes

"The first rule of holes: when in one, quit digging." — Molly Ivins

I founded my first SaaS company with my high school best friend. He had graduated from the University of Texas with an Electrical Engineering degree and had been working in the family computer business since he was fifteen. We hatched the idea sitting in a hot tub at a mutual friend's party and would soon discover that inspiration born in hot tubs is far inferior to inspiration born in showers.

The early years were a relentless cycle of two steps forward, one step back. I often told people our business model was so good that even we couldn't kill it — like the plant your mother gives you when you leave for college, the one you never water that somehow survives the semester. She nurses it back to health over the summer and hands it back to you hoping you've learned something about botany. You haven't, of course. You proceed to water it with beer.

The turning point came in a conference room heated argument we'd been having for over an hour — one of those circular debates about an issue we deemed monumental at the time. A Board member from Lebanon named Tony had been sitting quietly through the whole affair. Finally, when it was clear we'd made no progress, I asked Tony for his opinion. His response became a watershed moment for me. He simply asked, "Brent — what is the first rule of holes?"

The first rule of holes is that when you're in one, you stop digging. This is sage advice I've carried with me and shared with fellow travelers throughout my years as a business owner, investor, coach, and consultant. I find myself returning to it often, asking which end of the shovel I'm holding.

When we are digging in our business, we rarely take time to plan. We are oblivious to the unnecessary holes we're creating, unaware that working harder and faster is only making things worse. As Benjamin Franklin put it, "If you fail to plan, you are planning to fail."

Stopping the digging is only the first step. It doesn't remove you from the hole you're already in. What it does is create the space for a sequential plan of escape — and no two paths will ever look the same. However, there are tools and a framework from which to choose the best route for each situation.

What is certain is that inaction is itself a form of action. Staying in the hole may feel safe in the short term, but it will eventually become your undoing. The Beyond Bedlam process is the construct for a roadmap out. It does not guarantee success, and it doesn't presume to answer every specific question. What it does is address the main issues to be considered on the journey, provide real examples, and suggest overarching principles to guide your thinking.

The journey is organized into five sequential steps: Stakeholder Input, Value Analysis, Infrastructure Alignment, Fractional Decisions, and Measured Implementation.

The components of each step are enumerated and illustrated with examples drawn from my own SaaS experiences. I've offered considerations for each topic — but they are general and by no means exhaustive. Like any process, this one is constantly being refined and adjusted to account for changes in technology and the marketplace.

Where possible, I've deliberately avoided endorsing specific technical solutions, since the shelf-life of any particular recommendation is short. Instead, I've focused on the underlying issues that must be confronted. For more current and specific guidance, I'm building that out through the blog at www.beyondbedlam.com — a format better suited to the pace of change in this industry.

Part I

Stakeholder Input Chapters 1–16

Before a single line of code is written, the most valuable intelligence in the organization lives in the people closest to the problem. This section is about listening before building.