Three decades of deciding where the effort actually pays off.
I did not start with a plan. I started with a job, then a door, then a decision. The discipline I bring to technology capital today is the same one that ran every one of those choices.
Effort is not the goal. The outcome is.
I learned that on a shop floor long before I learned it in a boardroom. Every decision since has been the same question in a different setting: where does the time and the money actually return value? That question is the whole of how I think about technology now.
Doors opened. I chose which ones to walk through.
- Before the plan
I was working long before I had a plan
I worked through school. An ice cream counter, a bookstore, a Dairy Queen. I was earning before I had any idea where it led. What I took from those years was plain: do the work, and stay alert to the door you have not noticed yet.
- The first door
A Kroger manager handed me an application
He walked in, handed me the form, and asked me to fill it out. That was the opening. I took the job, stayed through college, and entered management training. The lesson was not that the door appeared. It was that I chose to walk through it.
- The next door
An opportunity in San Antonio, and H-E-B
A larger operation, a new market, higher expectations. I learned corporate management there and took on more responsibility. I started to see the business as one connected system rather than a set of separate tasks, and that changed how I read every decision after it.
- Into technology
The same question, now about systems
That wider view led me into technology, where one question kept returning: is this decision returning value, or just generating activity? I went on to serve as a three-time Chief Information Officer and as a Chief Privacy and Data Officer, across some of the largest names in grocery and retail.
- Today
The same principle, at a larger scale
Across those years, as an employee and later as an advisor, I worked with many organizations and many leaders. The wins taught me what good looks like. The failures taught me more. Jacob Meadow Associates is what I built from both.
Today I am Founding Partner of the firm. The principle has not changed since the shop floor. Treat technology as capital, expect a return, and measure the outcome. Now I bring it to executive teams and boards making decisions worth far more than the ones I started with.
I still teach the same idea I run on.
Whether the audience is a board weighing a platform decision or a room of students deciding what to build, the message holds: the tool is not the point, and the effort is not the point. The outcome is. The work is choosing the approach that gets you there.
The thesis, before it was a thesis.
I found the leak nobody could see.
At a regional grocer, the business was losing an estimated 1.5 million dollars a year to pricing discrepancies it could not quantify. I stood up real-time business intelligence that exposed the gap at the point of sale and began closing it, cutting those losses by eight percent in the first pass. You cannot price what you cannot see, so I made it visible.
I modernized the riskiest system in retail.
The point of sale is the backbone of a retailer, and most technology leaders will not touch it. I moved it off a legacy platform onto the cloud across a multi-location grocer, through the inflection point where the wrong call stops every register in the company at once.
I took capital out of the foundation.
I moved an entire data center to private cloud and replaced the backup estate for more than four hundred servers with a cloud service, removing the capital and operating cost of hardware the business no longer needed to own. The same capability, with less capital tied up in it.
I built resilience into the network.
Across every location, I re-architected the network and its security onto a modern, zero-trust model. The result was steadier uptime, fewer outages, and lower network cost, which are the conditions a store needs to actually serve its customers.
Three-time Chief Information Officer. Chief Privacy and Data Officer. Founding Partner.
Berkeley Chief Executive Officer Program, Berkeley Executive Education, 2026
I took it to be a better chief executive for my own firm, and to understand the decisions my clients face from their side of the table.
Two rules I have kept the whole way.
Say yes to opportunity unless there is a real reason not to
Fear is not a real reason. When a decision frightens me, that is usually a signal the decision matters, not a signal to avoid it. The doors that built this career were ones I could have talked myself out of.
Respect effort, but never mistake it for progress
I have watched three months and seven thousand lines of work produce nothing, and a better approach solve the same problem in an afternoon. Effort is not the result. Direction is what pays.
The same discipline, applied to your portfolio.
For boards and executive teams ready to treat technology the way they treat capital. Run the audit, set the method, or bring me in to speak.