The Shenkin Letter
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The CFO's
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Straight talk on financial leadership, board governance, and building companies that last — written the way Bill talks. Direct. Credible. Occasionally sharp. No fluff, no pitch, no boilerplate. Just the kind of thinking that takes 40 years to earn.
600–900 words
Free. Always.
Under 5 minutes to read
Free. Always.
600–900 words
Under 5 minutes to read
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Every Issue
What You Get
Every Other
Tuesday.
The Shenkin Letter arrives at 7 AM Mountain on alternating Tuesdays. It is always four sections. It always stays under 900 words. And it always ends with an open invitation to reply directly to Bill or book a conversation.
Cadence: Every other Tuesday, 7 AM MT
Length: 600–900 words · Under 5 minutes
Tone: Direct. No corporate. No fluff.
Cost: Free. No paid tier. No upsell.
Platform: Sent via Agora · Archived here
01
The big idea
One Insight. 600–900 Words.
The lead idea of each issue — drawn from one of Bill's five content pillars. Written in Bill's voice: direct, experienced, occasionally blunt. Not edited into oblivion. This is what most newsletters call their "main piece." Here, it's the opening, and it leads with the conclusion.
02
One Number
A Stat That Changes How You See Something.
One financial stat, data point, or market figure — paired with Bill's interpretation. The number is always chosen to reframe something the reader thought they already understood. Not a data dump. A lens.
03
What I'm Thinking About
A Market Trend, a Governance Observation, or a Performance Angle.
Shorter — 100 words or less. A pattern Bill is noticing across client conversations, a governance principle he's been testing in the boardroom, or an observation from training that applies to running an organization. This is where readers say they most feel like they're inside Bill's head.
04
Office Hours
An Invitation to Reply or Book 15 Minutes.
Every issue closes the same way: a direct invitation for the reader to reply with a question, push back on the main idea, or book a 15-minute conversation. Bill reads every reply. This is the section that generates the most advisory and board seat conversations. The newsletter is not a broadcast. It's an ongoing dialogue.
Sample Issue
What a Typical Issue
Looks and Reads Like
This is a representative preview of The Shenkin Letter — formatted exactly
as subscribers receive it. Real topics, real structure, Bill's actual voice.
The Shenkin Letter — Issue #3 · billshenkin.com/newsletter
The Shenkin Letter — Issue #3 · billshenkin.com/newsletter
The Shenkin Letter
Financial leadership · Board governance · The long game
Issue #2 · Month 1 ~7 min read
CFO Leadership · Tax Strategy · Wealth Creation
Good morning —
Over the last several years, I've had conversations with entrepreneurs, real estate investors, and business owners who all shared one thing in common: they were spending enormous energy trying to minimize taxes after the fact.
That is tax defense.
And while defense matters, it's rarely where significant wealth is created. The people who consistently build and preserve wealth tend to approach tax differently. They don't wait until March to talk to their CPA. They build tax strategy into how they structure compensation, acquisitions, investments, exits, and ownership from the beginning.
That is tax offense.
Today's letter is about what that actually looks like in practice.
01 The Big Idea
Tax Offense vs. Tax Defense
Most tax planning in America happens backward.
The business owner has a good year. Income shows up. Maybe there's a surprise K-1. Maybe a liquidity event. Maybe a large capital gain. Then sometime between January and April comes the familiar question:
What can we do to reduce taxes?
By then, most of the meaningful decisions have already been made.
Real tax strategy happens before the transaction — not after the return is being prepared.
"The largest tax savings rarely come from deductions. They come from structure, timing, and intentional decisions made years before the taxable event occurs."
Tax offense means thinking proactively about:
How equity is issued
How entities are structured
When income is recognized
How compensation is designed
Whether a deal is an asset sale or stock sale
Where value appreciation will occur
How succession and estate planning align with ownership strategy
These decisions compound over time.
I recently reviewed a situation where founders were focused on maximizing EBITDA ahead of a future exit — which was absolutely the right operational focus. But they had never seriously evaluated whether they qualified for QSBS treatment, whether trust planning should occur before appreciation accelerated, or whether parts of the ownership structure would create avoidable state tax exposure during a sale.
Those are offensive tax conversations.
And they matter because once the LOI is signed, most of the leverage is gone.
The same principle applies to closely held businesses and family offices. Sophisticated families don't merely ask, "How do we reduce taxes this year?" They ask:
What assets should appreciate outside the taxable estate?
How should future generations participate in ownership?
Where do we create liquidity?
What is the most tax-efficient path to a transition event?
How do we avoid forcing future decisions under pressure?
Tax defense reacts to outcomes.
Tax offense designs them.
02 One Number
90%
Approximately 90% of privately held businesses in the United States are structured as pass-through entities.
Many of them were formed quickly, inexpensively, and without long-term exit strategy in mind. Years later, owners discover that the original structure — which may have saved a few thousand dollars early on — can create millions in unnecessary tax friction during a transaction or generational transfer.
The earlier strategic planning begins, the more options exist.
03 What I'm Thinking About
One of the biggest mindset shifts founders and executives struggle with is understanding that tax strategy is not separate from business strategy.
It is business strategy.
I've seen leadership teams spend months debating marketing spend, pricing models, and hiring plans while treating tax structure as an annual compliance exercise delegated entirely to outside preparers. Meanwhile, the ownership structure quietly determines how much of the eventual outcome the founders actually keep.
The best operators I know understand something important:
Every major financial decision has three outcomes:
Operational outcome
Legal outcome
Tax outcome
Elite leadership teams evaluate all three simultaneously.
And frankly, this is where experienced CFOs and board members create disproportionate value. Not by preparing returns — but by helping management see around corners before decisions become irreversible.
04 Office Hours
If this issue resonates with you, it may be time to shift from reactive tax conversations to proactive tax architecture.
Whether you're:
Preparing for a future liquidity event
Evaluating entity structure
Thinking about succession planning
Navigating complex partnership issues
Building investor-ready financial infrastructure
Or simply trying to become more intentional about long-term wealth preservation
— these are conversations worth having before the pressure arrives.
Reserve 15 minutes with Bill. No pitch, no deck. Just a direct conversation about your business, your goals, and whether strategic financial leadership could materially improve the long-term outcome.
Reserve 15 minutes with Bill. No pitch, no deck. A direct conversation about what you're working on and whether his experience is relevant to your situation.
(720) 506-4105
[email protected]
Englewood, CO
BILL Shenkin
CeFO | A Numera Company
Financial leadership for high-net-worth families and entrepreneurs
cefo.net
BILL Shenkin
(720) 506-4105
[email protected]
Englewood, CO
CeFO | A Numera Company
Financial leadership for high-net-worth families and entrepreneurs
cefo.net
Past Issues
The Complete Archive
Every issue of The Shenkin Letter lives here — searchable, filterable, and permanently available to subscribers and non-subscribers alike.
1
Month 1 — Publishing Soon
Why I'm Writing This Newsletter — And What You'll Actually Get From It
The welcome edition. Why Bill decided now is the time to share 40 years of pattern recognition directly — and what readers can expect from every issue that follows. Personal, direct, sets the tone for everything ahead.
02
Month 1 — Publishing Soon
Tax Is Offense, Not Defense. Here's What That Actually Looks Like.
First strategic issue. One tax planning insight for business owners that most CPA firms will never tell you — because it requires thinking about the year before the year you're in. The difference in retained wealth is not incremental.
03
Month 2 — Publishing Soon
What a $2 Billion Acquisition Taught Me About Financial Readiness
The Colorado Rockies story and what Bill learned guiding companies through acquisition processes. Built for shareability and designed to be the most-forwarded issue of the first quarter. Previewed above.
04
Month 2 — Planned
The Board Governance Question No One Is Asking — And Why That's a Problem
A Pillar II deep dive aimed directly at PE sponsors and family office principals evaluating board talent. The question management hopes the board never asks — and why asking it is the entire point of independent governance.
05
Month 3 — Planned
Estate Planning Is the Most Ignored Financial Strategy in Family Business
High-value for the family office and family business audience. The decisions that protect generational wealth are almost always made 10 years before the wealth event. Most families wait until the urgency begins. By then, half the options are gone.
06
Month 3 — Planned
CFOs: Stop Being the Last Voice in the Room
Pillar I leadership provocation. The CFO who waits to be asked is already playing the wrong game. This issue is about what it looks like when financial leadership actually leads — and why most CFOs are trained to do the opposite.
New issues publish every other Tuesday beginning Month 1. Subscribe below to receive every issue the moment it publishes.
The Readership
Written for
People Who Make
Real Decisions.
The Shenkin Letter is not written for everyone. It's written for the people who actually have to live with the consequences of financial leadership decisions — and who appreciate being treated like adults.
CFOs navigating PE-backed growth
PE Sponsors evaluating portfolio talent
Founders planning an exit in 3–7 years
Family office principal
Independent board directors
Operating Partners
M&A and deal advisory professionals
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Conference organizers scouting speakers
More From Bill
The Newsletter Is Where It Starts.
Here's Where It Goes.
All Content
Read Every Article, Podcast, and Video in One Place
Every insight published in the newsletter becomes an article, a podcast clip, or a short-form video in the Insights archive. If you want to go deeper on any topic, that's where it lives.
For PE Firms & Family Offices
Put the Thinking to Work in Your Organization
If any issue of the newsletter raised a question you want to explore in your specific context — board governance, fractional CFO, or tax strategy — a 15-minute call with Bill is the right next step.
For Event Organizers
Bring This Thinking to Your Conference Stage
Every newsletter pillar maps directly to a keynote program. If a topic resonates with your audience, it can be built into a full speaking engagement for your event.
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