Darren Cherrington, Esq. — Tax, Entity & Estate Planning

The Approach

Strategic tax, entity, and estate planning — designed as one system.

Most legal planning feels like buying expensive, one-off documents from a stranger in a suit. I do it differently. I help entrepreneurs, business owners, and investors build tax, entity, and estate structures that actually fit together — and I explain every piece in plain English, so you know what you’re signing and why it’s there. We meet by video, wherever you are, and I work with clients across the country. Flat fees on the work that can be priced flat, and a clear hourly rate when it can’t.

Why Work With Me

Three reasons clients choose to work with me.

01

Strategic & Engineered Precision

I came to law from engineering. My first job out of college was as a thermal systems engineer for Hyundai-Kia — proving out vehicles in the hardest conditions on the continent, from Death Valley in July to International Falls in January. Then I spent years as a patent attorney, protecting the inventions that global automakers and Fortune 500 technology companies are built on. Same work, different asset: what I protect now is everything you’ve built — designed the way an engineer would, with every entity, trust, and tax election working as one system instead of bolted together as problems come up.

02

Casual & Transparent Collaboration

You shouldn’t need a law degree to understand your own estate plan. I explain every structure in plain English, walk through exactly why we’re building it and what it does for you, and never hide behind legal jargon. Working with me feels like talking strategy with a friend who happens to be an attorney — not sitting through an intimidating legal lecture.

03

Predictable & Transparent Pricing

Great legal work shouldn’t be a black box or a big-firm privilege. My core services are flat-fee and posted right on this page, and when work falls outside those packages, it’s a clear hourly rate quoted before we start. I’ll also steer you away from the out-of-state “silver bullets” that get sold as tax magic and mostly generate filing fees and headaches. You’ll always know what you’re paying, why it’s worth it, and what it’s protecting.

The Design Review

What we look at.

A Design Review is a full read of how your business, your taxes, and your assets currently fit together — and where they don’t.

What you’ve already built

Your entities, who owns them, and whether the paperwork behind them still holds up. Most people pick up a structure or two along the way without anyone checking that the pieces match the business they have now.

How you’re being taxed

Your personal return and one business return, read side by side. S-corp status, a defensible salary-and-distribution split, the elections that fit your actual numbers — what’s already working, and what’s being left on the table.

Where the gaps are

The pieces that were never connected — assets sitting outside the structure, ownership that doesn’t match the plan, risk stacked in one place. You get a straight answer on what actually matters and what can wait.

The Process

How a Design Review goes.

Four steps over a couple of weeks. You know what’s happening at each one, and it ends with a clear list rather than an open engagement.

01

Before We Meet

I read your file

You send your personal return, one business return, and whatever entity documents you have. I spend up to an hour going through them before we ever get on a call, so the first conversation starts from your actual numbers instead of a blank page.

02

The First Call

Preliminary Review

Up to an hour by video. I walk you through what I found, you fill in the parts the documents don’t show, and we agree on what your plan actually needs to do. This is where most of the questions get answered.

03

The Drafting

Your Master Schematic and Build Sheet

Up to an hour and a half of drafting. I turn that conversation into a single-page picture of your structure and a numbered list of what to do about it. Both are yours to keep.

04

The Final Call

Final Review

Up to an hour to walk through both documents, make corrections, and answer whatever is left. That call closes out the engagement — no open meter, no surprise invoice afterward.

What You Walk Away With

Two documents you keep.

A Design Review ends with a picture of your structure and a list of what happens next.

Your Master Schematic

Engineers don’t start building until somebody draws the thing. Same idea here.

Your Schematic is a single page showing your whole setup — every entity, who owns what, how the income moves, and where your estate plan sits on top of it. For most people it’s the first time they’ve seen their own structure in one picture.

Your Build Sheet

The Schematic shows you what you’re building. The Build Sheet is how it gets built.

It’s your written recommendations turned into a numbered list — what to form, what to transfer, what to sign, and the order it happens in — with every item marked as mine or yours, so nobody is waiting on anybody.

Pricing

What it costs.

No mystery, and no meter running while you decide. Here’s what the core work costs, and how much of my time is built into each one.

Introductory CallUp to 1 hour by video, for new clients. A get-to-know-each-other call — your goals, where the business is headed, and one or two things that are pressing right now. $250

Design ReviewTax planning and entity structuring, flat fee. Includes up to 1 hour reviewing your returns and business documents before we meet, a Preliminary Review call (up to 1 hour), up to 1.5 hours drafting your Master Schematic and Build Sheet, and a Final Review call (up to 1 hour) that closes out the engagement. That covers your personal return and one business return; additional entities or partnership returns run about 30 minutes each at my hourly rate, and I’ll ask before I spend the time. $1,495

Consultations and other workQuoted in writing before anything starts. $450 / hour

The Design Review is priced below my hourly rate on purpose — it’s meant to be an easy first piece of work. Time beyond what’s included is billed at $450 per hour, and I’ll ask before I spend it. Anything outside a Design Review gets quoted in writing once we’ve talked through what you need.

Ready to build a plan that’s designed to last?

Schedule a consultation and let’s talk through what your business and family actually need. It’s a working call, not a sales pitch — we’ll cover where you are now, what’s missing, and what it would cost to fix it. And if you don’t need me yet, I’ll tell you that too.

Schedule a Consultation

Your business,your property,your family —planned as one system.