What's new

Update · About

The About page now opens with a short deck about the problems the firm works on

A nine-slide deck at the top of About starts from what people are stuck on, says what the firm does about each, and ends with who to write to.

Working paper · Research

AI-Prepared Dashboards Add Data Faster Than People Can Decide

This paper argues that AI-prepared dashboards and digests add information faster than people can act on it, and proposes a Decisions & NBA Board: a short queue of decisions, each with cited evidence, options, an owner with authority and a dated check on the result. It matters because a report that changes no decision is a cost. No hypothesis has been tested.

Working paper · Research

Communicating Engineering Team Effectiveness to Executive Peers

This paper proposes a field-testable operating model for CTOs: one traceable evidence base that executive peers can inspect for their own jobs without relying on the CTO's persuasion. It matters because senior leaders often judge engineering by remembered incidents and impressions. The six hypotheses have not been tested.

Working paper · Research

Unleash DD214 as the Olive Button

This paper proposes Olive Button, a Blue Button-style FHIR implementation pattern for DD214 service data that helps meet the 30-, 120-, and 180-day mandates of Executive Order 14426 using existing systems and standards. It matters because the order now requires records sharing at separation. The FHIR mapping is an implementation hypothesis, and the order does not mandate FHIR.

New · Site

One page lists the new releases, papers, episodes and essays

What's new collects releases, papers, episodes and essays in one dated feed, newest first, with filters by area and kind and an Atom feed.

Release · Press

Every Press book can now have an online companion

Worksheets, field tools, coaching guides and sources that belong on a screen now live at a stable address beside each book, starting with The Code Takes Care of Itself.

Keywords: companion

Update · Ventures

Ventures shows each company and fund with its entity, operator, rights position and closure condition

The Ventures page lists the ventures, companies and funds the firm has started and shows, for each, what its charter requires before the first hire, or says that it is not stated.

Challenges and Opportunities of Integrating AI into Health Systems

Episode 10 of The Shahid Shah Show.

New · Capital

A browser tool tests whether funding would speed up a repeatable customer motion

The seed and early-capital readiness tool says whether money would speed up a repeatable customer motion or only extend the search for one.

Stop Wasting Your Colleagues’ Time With Your Bad Writing

Bad internal writing is not a writing problem. It is a respect problem. Every vague document you send asks your colleagues to finish your thinking for you. AI made the slop cheap to produce and did nothing for the cost of reading it.

If It Isn't Written Down, It Didn't Happen

Regulated industries run on one rule: no document, no event. That sounds bureaucratic until you try to reconstruct a decision from six Slack threads and five different memories. Here's the pattern, and why AI just made it cheap.

Stop Telling People to Communicate Better. Instrument It.

Most companies don't have a communication problem. They have an uninstrumented one. Here's how I'd use AI to score communication behavior, turn complaints into structured findings, and leave the human judgments to humans.

Why LLMs Seem to Get Wobblier Near Completion

My working theory: these models are great at continuing and lousy at being done. The last stretch of a project probably needs different rules, not a smarter model — a canonical spec, scheduled audits, and a second model as judge.

Some Companies Are Already on Life Support. AI Just Hasn’t Pulled the Plug Yet.

Revenue is not the same thing as being alive. A test for founders of mature software companies: if you started this company today, knowing what AI makes possible, would you build anything resembling what you now operate?

Non-Technical People Belong on Technical Calls. They Just Shouldn’t Ruin Them.

The reflex when a business stakeholder derails a technical working session is to stop inviting them. That is almost always the wrong fix. What technical meetings need is rules of engagement, not walls around engineering.

Why Doesn’t Engineering Already Know This?

A guide for executives who think every technical problem should already be obvious to the engineering team. Simple after discovery is not the same thing as obvious before discovery, and confusing the two produces terrible management decisions.

New · Network

Network lists each search it is running: the thesis, who qualifies, and the signals so far

The hunts page shows what Network is looking for, one search at a time, and marks every count and candidate as illustrative.

Caris Life Sciences Series - Part 3 of 3: The Future with Dr. Milan Radovich

Episode 9 of The Shahid Shah Show.

New · Ventures

The Care Delivery funds are described: one active under $1M, one in formation

Care Delivery Fund I is an active fund under $1M that incubates ten companies and programs, and Fund II is in formation, explored at $25M to $50M.

Native Alpha: Start With the Advantage You Already Have, Not the Opportunity You Just Noticed

Alpha, in investing, is the return you cannot explain by the market. Native Alpha is the business version: the unusual advantage already sitting inside your company, your customers, your data, and your relationships, and the discipline of letting it decide what you build, buy, fund, sell, and stop.

Test First, Discover Second, Build Third: A Practical Strategy for Brownfield and Legacy Software Engineering

For non-trivial changes to legacy systems, define the business outcome first, then how you will prove the change works, before you estimate or build it. Outcome, evaluation, bounded discovery, incremental implementation, in that order.

Alpha, Benchmarks, and Why I Borrowed the Word From Investors

Alpha in finance is the return you cannot explain by the market. Here is what that actually means, why investors bother separating skill from luck, and which parts of the idea carry over to running a company and which do not.

Capability Is Cheap Now. Advantage Is Not.

AI made building things dramatically cheaper, which quietly destroyed a lot of differentiation that was never real. How to tell commodity execution from differentiated execution, and where to spend the judgment you have left.

Someone Outside the Room Has to Care

Enthusiasm inside a company proves nothing. The strength of evidence for an advantage is measured by what somebody outside gave up to act on it, from a compliment at the bottom to a renewal at the top.

Product-Market Fit Does Not Tell You Who to Sell To

The same product can be ordinary for one buyer and transformative for another. Product-asymmetry fit and the Ideal Alpha Profile explain why the customer with the biggest problem is often the wrong customer.

Where Native Alpha Actually Lives, and How It Decays

Advantage is contextual, it hides at surprisingly small scales, it needs protection in the place it actually lives, and it expires. How to find it, where to put the fence, and when to admit it is gone.

First Principles Got Turned Into a Slogan

Reasoning from first principles means stripping a problem down to what you can verify and rebuilding from there. In executive hands it usually means ignoring people with experience. This is the real version, and how it fits with Native Alpha.

Caris Life Sciences Series - Part 2 of 3: The Access with Dr. Joseph C. Murray

Episode 8 of The Shahid Shah Show.

Caris Life Sciences Series - Part 1 of 3: The Science with Dr. James Hamrick

Episode 7 of The Shahid Shah Show.

Why Excuses are a Big Problem for Builders and Buyers

Episode 6 of The Shahid Shah Show.

Eliminating unnecessary processes before implementing new technology

Episode 5 of The Shahid Shah Show.

What Governance is Supposed to Mean in Digital Health

Episode 4 of The Shahid Shah Show.

Hard-won Lessons Selling to HDOs

Episode 3 of The Shahid Shah Show.

What Buyers and Builders should know about Prior Auth Interoperability

Episode 2 of The Shahid Shah Show.

Welcome and About the Show

Episode 1 of The Shahid Shah Show.

Working paper · Research

Plan EHR Integrations in Months, and Help Your Customers Shorten the Wait

This landscape review tells digital health executives how long an EHR integration takes and what shortens the wait. It gives a planning range of six to twelve months from kickoff to first customer live, most of it spent on customer and EHR-vendor steps rather than code. The range is a judgment from public sources, not a measured median.

Customer-Led Engineering: Software Development in the Age of AI

How modern engineering teams should evolve their processes, priorities, and incentives to remain relevant in the era of AI, agents and intelligent systems.

Why Email and Office Documents Are the Perfect UX for Starting Your AI Journey

It may sound legacy, but email and document-based workflows are the most effective user interface for launching real-world AI solutions. Here's why AI should start where customers already are.

How Senior Officials Should Think About AI Roadmaps

AI roadmaps are not just technical plans; they are trust strategies, implementation guides, and accountability tools. An AI roadmap for a government or a mission-driven organization has a few essential components, and a test tells whether it is ready to execute.

Why Machine Attestation is Key in the Age of CMMC

Under the DoD’s CMMC Program, maintaining continuous compliance is crucial, and machine attestation provides the consistency and accuracy human checks can’t match. By automating compliance tracking, contractors can ensure real-time verification, creating a robust audit trail and reducing compliance risks across contract lifecycles.

Healthcare’s Cybersecurity Crisis: Leadership Challenges and Strategic Solutions

Healthcare's cybersecurity crisis is critical, with outdated defenses exposing patient data and trust. Zero Trust is now mandatory, and delays in breach detection can cause immense damage. Effective leadership, including fractional CISOs, is essential for modern defense. Inaction isn't an option, proactive steps are necessary to safeguard against sophisticated threats.

CTOs: The Overlooked Asset in a VC's Portfolio

Venture capitalists often overlook the strategic importance of a Chief Technology Officer (CTO), mistaking technical co-founders as a simple checkbox. A seasoned CTO bridges vision and execution, aligning tech strategy with business goals, mitigating risks, and driving innovation, key factors that can make or break a startup's success.

Transforming Healthcare with Advanced Applications of High-Performance Computing

High-performance computing (HPC) has revolutionized healthcare, particularly in fields like oncology and biomedical engineering, where it enables researchers to perform complex simulations and genetic analyses far quicker than traditional methods. The transition from conventional numerical analysis to dynamic generative AI has further expanded the capabilities of this powerful technology, not only enhancing patient care but also reshaping expectations for rapid medical innovation.

From Vulnerability to Strength: The Role of CISO Services in Cyber Resilience

There was a time when no one really needed a CISO. Today, an organization would be dangerously insane not to have one. And that CISO had better be top-notch. The role of the Chief Information Security Officer (CISO) has evolved significantly from being solely a technology-focused professional to becoming a strategic business leader

Embrace Compliance as Code

Exploring the benefits of transitioning to a 'compliance as code' model by reflecting on successful implementations of other 'as code' models.

Role of a Part-Time Chief Technology Officer (CTO) in Regulated Industries

Explore how a Fractional CTO can navigate the complex technological landscape in heavily regulated industries, making compliant and informed decisions.

Systems that require human attestation to prove compliance are not secure

While a system may meet all the necessary regulations and standards, it can still be vulnerable to threats and attacks because of human attestation.

Staff Retention Might Be More Important Than Recruiting

Staff retention refers to the ability of a company to retain its employees over a period of time. It is a crucial aspect of any organization, especially in the technology sector where skilled professionals are in high demand.…

Enterprise Architecture: A Guide for Tech Leaders

Enterprise architecture is a strategic framework that helps organizations align their business and technology strategies. It provides a holistic view of the organization’s structure, processes, and systems, enabling effective…

The Benefits of Hiring a Fractional Chief Technology Officer

A Fractional Chief Technology Officer (CTO) is a senior-level executive who provides part-time, strategic guidance and leadership in the technology domain. Unlike a full-time CTO, a fractional CTO works on a contract basis,…

The Importance of Chief Information Security Officers in Federal Government Contracts

A Chief Information Security Officer (CISO) is a senior executive responsible for establishing and maintaining the enterprise vision, strategy, and program to ensure information assets and technologies are adequately…

How a Fractional Chief Technology Officer Can Drive Innovation

A Fractional Chief Technology Officer (CTO) is a highly skilled and experienced technology executive who works with companies on a part-time or project basis. They provide strategic guidance and leadership in the development…

Compliant Insecurity in Government Agencies and Contractors

I challenge the conventional wisdom on cybersecurity, focusing on the problem of 'compliant insecurity'.