The Seller's Playbook

Thinking About Selling Your Business?

Practical lessons for business owners on valuation, preparation, buyers, and closing. Written by Regina Fisher, based on her experience of more than 40 closed transactions.

Regina Fisher

‍Founder, Sierra Bay Partners

Business owner imagining a buyer showing interest, next to the steps of a business sale

The Seller's Playbook

Why Most Business Owners Have the Wrong Idea About Selling Their Company

Most owners think a sale starts when a buyer shows interest. Why preparation, process, and a defensible valuation decide the outcome.

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Illustration: Your business is probably not worth what you think

The Seller's Playbook

Your Business Is Not Worth What You Think—Here’s Why

Buyers pay for proven cash flow and low risk, not effort or potential. What really drives the value of a privately held business.

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Aerial view of brick rows with the words The Biggest Mistakes Owners Make Before Selling Their Business

The Seller's Playbook

The Single Biggest Mistake Owners Make Before Selling Their Business

Waiting until a sale feels urgent costs owners value and deals. Why preparing early builds leverage before a buyer ever shows up.

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Business owner daydreaming about a buyer who writes a check right away

The Seller's Playbook

The Buyer Who Is Supposed to “Just Get It”

Buyers issue LOIs on evidence, not stories. A real example of why past success and future potential do not carry a valuation.

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Financial projections marked too optimistic next to a checklist of plausible assumptions

The Seller's Playbook

Projections Don’t Get Deals Done. Plausible Assumptions Do.

Lenders ask what must change in the operation for projected numbers to happen. How sellers can support credible assumptions.

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Chart: Why deals fall apart after LOI. Non-QoE diligence findings 25.3 percent, QoE EBITDA discrepancies 21.3 percent

The Seller's Playbook

A Signed LOI Is Not the Finish Line

Most deals that fail after a Letter of Intent fail in due diligence. What 2025 data shows and how sellers can prepare before going to market.

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Note on a desk: The Sub-$10MM Deal Market Is Hotter Than You Think

The Seller's Playbook

The Sub-$10MM Deal Market Is Hotter Than You Think. But Only If You Know How to Show Up.

Buyers and lenders are active in the market for businesses under $10MM. Why a buyer-ready story and clean financials decide which deals close.

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The Seller's Playbook

Set Your Price. Or You Can Sell Now. But You Can’t Have It Both.

Price, structure, and timeline are three levers in a business sale. A real story of why locking all three draws interest but no closing.

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The add-back trap: every dollar hidden in add-backs can reduce valuation by three or four dollars

The Seller's Playbook

The Add-Back Trap That Cost an Owner 60% of His Valuation

Personal and startup expenses run through a business can cut its value by more than half. Why clean books are real money at the sale.

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The Seller's Playbook

It’s a Great Time to Sell Your Business. But Don’t Misread the Market.

It is a strong seller’s market with many active buyers. But educated buyers still price in risk. Why preparation and realistic pricing matter.

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High demand. Preparation is king. Regina Fisher playing bocce

The Seller's Playbook

Demand Is High. Preparation Is King.

BizBuySell data confirms strong buyer demand and more selective buyers. Why acquisition-ready businesses win in today’s market.

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Lead conversion: a funnel turning grey spheres into gold

The Seller's Playbook

Maybe You Don’t Need More Leads. Maybe You Just Need to Convert More of Them.

Lead generation is easier than ever. Turning a lead into a client still happens in a conversation. Why conversion is the skill to build.

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Owner dependent is not necessarily unsellable: 3x on $800K or 4.3x on $600K

The Seller's Playbook

Does Your Business Really Have to Run Without You Before You Can Sell It?

Many buyers want to be owner-operators. Why owners should run the numbers before replacing themselves to prepare a business for sale.

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$1M EBITDA times 5 multiple equals $5M business value?

The Seller's Playbook

$1 Million EBITDA Doesn’t Automatically Mean a $5 Million Business

The multiple reflects the risk behind the earnings. Why two businesses with the same EBITDA can sell for very different prices.

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Seesaw: $210,000 in tax savings against $700,000 in value lost at sale

The Seller's Playbook

$210,000 in Tax Savings Could Cost You $700,000 at the Sale

Minimizing taxable income and maximizing business value work in different directions. How to document expenses now to protect your price.

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Lender pre-approval letter stamped not enough, next to a checklist of what a business broker asks buyers for

The Seller's Playbook

How I Verify a Buyer Before They Meet My Client

A pre-approval letter is not proof. What a business broker asks every buyer for before introducing them to a seller.

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Business buyer telling friends about his new business at a Fourth of July backyard barbecue

The Seller's Playbook

Finding an Interested Buyer Is Real Easy

Buyers find attractive businesses on their own. Getting one comfortable enough to close at a justified price is where the real work happens.

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BizBuySell Confidence Index chart of business buyer and seller sentiment from 2013 to 2026

The Seller's Playbook

Small Business Sales in Q3 2026: Plenty of Buyers, but Not for Every Business

BizBuySell Q3 2026 data shows strong buyer demand but choosier buyers. What the $1 million dividing line means for business owners.

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Hand-carved stone sculpture next to a white bathtub under the words Owner Dependent

The Seller's Playbook

Owner-Operated or Owner-Dependent?

A hands-on owner is not automatically a valuation risk. The real question is whether the business can keep making money without the owner.