What You Can DIY vs Hire (Legal Edition) for Solo Businesses

Solo work rewards speed. Legal work punishes sloppy speed.

The goal isn’t to “DIY everything” or “hire everyone.” It’s to spend money where it buys down real risk, and DIY the rest with confidence.

This guide is general information, not legal advice.

Recommended Reading Order (Legal Cluster)

1. Start here: How to choose an entity and set up the basics
2. Contracts next: Contract basics for solos
3. You are here: DIY vs hire (legal)
4. Then: Common legal mistakes (and how to avoid them)

The 3-Question Filter (Use This Before You Spend Money)

When deciding whether to DIY or hire, ask:

1. What’s the downside if I get it wrong? (annoying vs business-ending)
2. How likely is it I’ll get it wrong? (clear checklist vs nuanced judgment)
3. How often will I reuse this? (one-time filing vs reusable contract)

If the downside is severe and the likelihood is non-trivial, hire.

Usually Safe to DIY (With Good Checklists)

1) Basic entity formation (in straightforward cases)

Often DIY-able when:

• single owner
• standard state/jurisdiction path
• no special licensing/regulated constraints

Still do the basics:

• separate finances
• keep simple records
• don’t pretend entity formation replaces insurance/contracts

2) Basic business hygiene

DIY:

• business bank account + bookkeeping workflow
• invoice templates and payment process
• organizing contracts, receipts, and policies

If you’re early-stage overall, the Solo Readiness Checklist tool can help you prioritize.

3) First-draft contracts (for low-risk, low-dollar work)

DIY can work when:

• project size is small
• deliverables are clear
• you’re not in a regulated/high-liability space

Use the structure from: Contract basics for solos.

The trick: treat your first draft as a baseline, then upgrade when deal size grows.

Worth Hiring For (High-Leverage, High-Risk Areas)

1) Anything regulated, licensed, or professional-entity-related

If your profession has licensing boards, ethical rules, or required entity types (PLLC/professional corporation), hire or at least get a consult. The cost of “oops” can be massive.

2) High-dollar contracts and enterprise clients

Hire when:

• contract value is meaningful to you
• client paper includes heavy indemnities, security addenda, or complex terms
• the client wants to own everything (including your pre-existing IP)

One professional review can prevent a contract from quietly nuking your business later.

3) Hiring employees, complex contractor setups, or multi-owner arrangements

Hire for:

• employee onboarding/compliance
• contractor classification questions
• equity/ownership agreements (operating agreements, buy-sell terms)

4) Trademarks and IP strategy (when your brand actually matters)

DIY brand basics:

• consistent name, domain, and positioning

Hire when:

• your brand name is core to your business (and you’re investing in it)
• you’re expanding into multiple product lines/markets
• there’s a real risk of conflict

5) Privacy, data, and security (builders + data-heavy services)

Hire or get specialist help when:

• you handle sensitive user/customer data
• you’re selling B2B and customers ask for security terms
• you operate across jurisdictions with complex privacy requirements

“DIY First, Then Hire” Upgrade Triggers

Use these triggers to decide when to level up:

• Your average project size crosses a threshold where one mistake hurts (pick your threshold).
• You start reusing the same contract stack repeatedly and want it tightened.
• A client hands you a contract you don’t understand (or don’t like).
• You’re adding owners, employees, or complex compensation.
• You’re entering a regulated or higher-liability category.

Segment-Specific Guidance: Where Pros Usually Pay Off

Builders

Often worth hiring for:

• terms/privacy tuned to your product and data collection
• contractor IP assignment (if you outsource design/dev)
• enterprise security addenda review (as you move upmarket)

Advisors (consultants, coaches, fractionals)

Often worth hiring for:

• contract review if you’re stepping into high-stakes advisory roles
• conflict-of-interest language if you serve multiple companies in a niche

Pair this with good scope control: Scope Creep guide.

Agencies

Often worth hiring for:

• an MSA that protects your pre-existing IP and sets acceptance rules
• subcontractor agreement template (if you bring in help)

SMBs

Often worth hiring for:

• licensing/permits guidance in your locality
• liability/insurance alignment with your actual services
• consumer-facing terms (deposits, cancellations, warranties) if they’re common in your trade

How to Hire Smart (So You Don’t Waste Money)

• Bring a one-page summary: what you sell, typical client, typical deal size, biggest worry.
• Ask for “standard positions” and red lines (what you should never accept).
• Request templates you can reuse (SOW, MSA clauses) so it pays off repeatedly.

Next Steps

• Entity decision: Choose a business entity as a solo
• Contract stack: Contract basics for solos
• Avoidable traps: Common legal mistakes

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