The Tech Dilemma is about one problem: why software organizations fail to deliver, and what actually fixes it.

I have spent 25+ years building companies. Thirty of them. Twenty failed. Ten became multi-million-dollar wins. I am the CEO of Sonatafy Technology, a Software Delivery Acceleration Systems company, where I work with executives whose software delivery has stalled and who are tired of being told the answer is more engineers.

I also host Software Leaders Uncensored, a podcast featuring candid conversations with CTOs, CEOs, and engineering leaders across 195+ episodes. Those conversations became the 2026 Software Delivery Failure Index, a study of why software projects actually fail. The patterns that emerged are the backbone of this newsletter:

• The Backlog Illusion: motion mistaken for progress

• The Coordination Tax: friction at the seams between teams

• The Ownership Gap: nobody accountable for the outcome

• The AI Validation Gap: delivering AI nobody can prove is working

I have published 248+ articles in Forbes, Entrepreneur, CIO, and Inc., and I am the author of the Amazon bestseller Fail Hard, Win Big and co-author of The Backlog Illusion.

The Tech Dilemma is not theory. It is what actually breaks and scales companies, written by someone who has done both.

Start with the data: Download the Free 2026 Software Delivery Failure Index

Go deeper:

• New here? Read the Start Here guide to the four failure patterns

• Sonatafy Technology: www.sonatafy.com

• Software Leaders Uncensored: www.softwareleadersuncensored.com

• The Backlog Illusion: www.thebacklogillusion.com

• Speaking and leadership: www.bookstevetaplin.com

• 30-20-10 Entrepreneurship story: www.failhardwinbig.app

• LinkedIn: www.linkedin.com/in/stevetaplin