CFO Insights - Finance, M&A & Capital Markets

Perspectives on capital allocation, M&A, fractional CFO strategy, and financial leadership for business owners and institutional investors.

Gregg Carlson is a CPA and CFA Institute member with 25+ years of CFO, Controller and financial analyst leadership across public companies, cannabis operators, gaming and hospitality businesses, and institutional investors. He has closed $700M+ in transactions. These articles apply that experience to the financial decisions founders, operators, and investors face.

To discuss a specific situation: gregg@gregg-carlson.com


Gregg Carlson Gregg Carlson

Valuing the End of 280E for Adult-Use Cannabis

Medical cannabis is already relieved from 280E — adult-use is the question that remains. Using McKinsey’s ROIC-versus-WACC framework on the five largest multistate operators, eliminating 280E on recreational sales is worth roughly $2.5 billion of intrinsic equity value, about 47% of their combined market capitalization.

Excluding goodwill, these businesses earn 15–19% on invested capital before tax, yet 280E drags the after-tax return to near zero. The gap is tax policy, not operations — and it is reversible. The probability of that change, however, remains unknown and should not be relied on.

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The Cannabis Finance Problem Just Changed — What Rescheduling Means for 280E, Banking, and Capital

Rescheduling changes more than the tax line. As 280E relief, banking access, and a lower cost of capital begin to converge in 2026, the financial model of the U.S. cannabis operator is being rewritten.

This piece looks past the headline at what actually shifts for operators and investors — effective tax rates, access to institutional lending and capital markets, refinancing windows, and the capital-allocation moves a CFO should be positioning for now, while the timing of full relief stays uncertain.

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AI Adoption for the Domain Expert Practitioner: What I Learned and How You Should Approach It

I have been applying AI tools to my CFO and financial advisory practice since ChatGPT became publicly available in 2022. The foundation that made that application productive from the start was not AI skill — it was 25 years of financial domain expertise that allowed me to direct AI effectively, evaluate its outputs critically, and integrate it into professional work that clients could rely on.

Andrej Karpathy frames the current moment precisely: everything is a skill issue. The AI capability is there. For domain experts, the bottleneck is lower than it is for generalists — because professional judgment is the most important variable in AI-assisted work.

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The Controller Function in the Age of AI: What Business Owners and Senior Management Need to Know

The Controller function — month-end close, account reconciliations, financial reporting, GAAP compliance — is the finance role most immediately transformed by AI.

AI automates the mechanical. It does not replace the judgment. Revenue recognition under ASC 606, complex accruals, intercompany eliminations, lease accounting under ASC 842, inventory costing methods, and management reporting context all require professional judgment that no current AI system can reliably provide. A business that replaces its Controller with AI tools alone will produce faster financial statements that are less reliable.

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AI at Scale: Three Approaches to Capital Allocation — A Corporate Finance Case Study Using Amazon, Microsoft, and Google

Amazon, Microsoft, and Google are each spending $80B–$200B on AI infrastructure in FY 2026 — a combined commitment approaching $600 billion. But the strategies are fundamentally different: Amazon is building vertically (custom chips + cloud), Microsoft is monetizing through distribution (Azure + Copilot + OpenAI), and Google is leveraging its model advantage (Gemini + Search + Cloud). The capital allocation choices each company makes today will determine their competitive positions for the next decade.

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Understanding Financial Statements: What Your P&L, Balance Sheet, and Cash Flow Statement Are Actually Telling You

Most business owners read their financial statements once a year, usually at tax time, after their accountant has already prepared them. The value in financial statements is not in confirming what happened — it is in telling you what is happening right now and what is likely to happen next.

The three financial statements are not three separate documents. They are three views of the same business, linked together. The income statement tells you whether you made money. The balance sheet tells you what you own and owe. The cash flow statement tells you whether you have cash. A business can show profit on the income statement and simultaneously run out of cash.

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Amazon (AMZN) Valuation After Q1 2026 Earnings: A Two-Stage DCF Analysis Across Seven Business Segments

Amazon’s Q1 2026 earnings beat across every major line: $181.5B revenue (+17% YoY), $23.9B operating income at a record 13.1% margin, AWS growing 28% to $37.6B (fastest pace in 15 quarters), and Advertising at $17.2B (+24% YoY) crossing $70B in TTM revenue.

Amazon is not one business — it is seven with radically different economics. AWS and Advertising, which represent approximately 31% of revenue, generate the overwhelming majority of economic value. Valuing Amazon without separating these segments produces a meaningless blended average.

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Raising Equity Capital: What Founders and Owners Need to Know in 2026

Equity capital is the most expensive form of financing measured in permanent ownership dilution. Every percentage point you give up is permanently gone unless you buy it back at a higher price later.

The most common mistake founders make is negotiating valuation hard and terms lightly. The terms — liquidation preferences, anti-dilution provisions, board composition, protective provisions — determine your actual economic outcome far more than the headline pre-money figure.

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AI in the Small to Medium Business (SMB) Finance Function

What AI and agentic AI actually do in your accounting and finance function — 18 concrete use cases, a three-phase implementation roadmap, and the regulatory framework every owner must understand before deploying AI in a financial context.

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