By: Jordan Gerheim, CEO – Outside Chief Legal LLC
Why Did You Start Your Business?
The Important Question Behind Your Legal Decisions
Before contracts, disputes, and deals, there was your answer to a simple question: Why did you start your business?
You might have wanted freedom, a better income, more control over your time, or a chance to build something that outlasts you. Maybe you saw a gap in the market and decided you could serve customers better than anyone else.
Every legal decision you make either supports that original reason or slowly pulls you away from it.
Maybe One of These Reasons?
Here are some of the most common reasons owners share for wanting to start their business:
- To control their schedule and build a life on their own terms.
- To earn more than a salary job would pay over the long run.
- To build an asset that can be sold or passed on later.
- To take care of their family and create stability.
- To solve a problem they care about and serve customers well.
- To build opportunities and good jobs for their team.
None of these reasons are “legal” on the surface. Yet legal choices shape each one, from how you bring in partners to how you handle contracts, employees, and risk.
Why This Matters More As You Grow
When your business is small, many problems can be fixed with a conversation and a handshake. As you grow, the stakes rise. There is more revenue, more contracts, more employees, and more eyes on your decisions.
That is when misaligned contracts, missing policies, unclear ownership, and sloppy deal terms start to work against the reasons you started in the first place. Instead of more freedom, you feel pinned to the business. Instead of building an asset, you build a job that is hard to escape and sell.
Legal support should help you move toward your real goals, not just clean up messes when they spill over.
What Can Go Wrong When the Law and Your “Why” Are Not Aligned
When your legal setup is disconnected from your reasons for owning the business, patterns show up:
- You want freedom, but you sign vendor and customer contracts that lock you into lopsided terms.
- You want to sell one day, but your company records, contracts, and ownership documents are disorganized or incomplete.
- You want to see your team thrive, but you have no clear employment agreements, handbooks, or processes, so every tough decision feels risky.
- You want to protect your family, but your personal and business assets are tied together, and one lawsuit puts both at risk.
None of this happens overnight. It creeps in over years of “we will deal with that later.”
A Simple Example: “I Started This To Spend More Time With My Family”
Imagine a founder who left a high-pressure job to have more control of his time and be present with his kids. The business does well. But there are no clear roles, few written policies, and every contract question runs through him.
Five years in, he is answering emails late at night, managing disputes on weekends, and signing rushed contracts that make him nervous. He started the business for family time, but the way the legal and operational side grew is actually taking that away.
A better approach is to step back, clarify his real goals, then set up contracts, authorizations, employment documents, and decision rules that allow others to carry more of the load while still protecting the company.
How Outside Chief Legal Shows Up for Your Business
Outside Chief Legal exists for owners who want legal counsel that starts with their purpose. Our work is anchored in the decisions you need to make and what you are really trying to build, then we create a personalized legal strategy around that.
We often serve as subscription-based fractional or outside general counsel for growing companies that want proactive guidance across contracts, compliance, employment, and disputes. Instead of waiting for fires, we help you spot dry brush and clear it before it lights.
A Business “Checkup” Around Your Why
For many owners, the right starting point is not a pile of new documents. It is a structured conversation about why you started the business, what you want the next five to ten years to look like, and what might get in the way.
Outside Chief Legal often runs a business legal “checkup” that reviews your entities, key contracts, workforce practices, and common risk areas through that lens. The goal is to spot blind spots, rank them, and give you a practical list of fixes you can tackle in phases, not all at once.
Do This Next: A Quick Owner Checklist
Take ten minutes and work through this:
- Write down, in one or two sentences, why you started your business.
- Add one more line on what you want the business to do for you in the next five years (income, time, exit, impact, or a mix).
- Look at your current legal setup: entity type, ownership, key contracts, and basic employment documents. Ask: Do these actually support the picture you just wrote down?
- Circle your three biggest worries about legal risk or conflict in the business.
- Note any handshake agreements or “understandings” with co-owners, partners, or core employees that are not in writing.
- Ask yourself: If I wanted to sell this business or step back in three years, what would a buyer or new leader see that might worry them?
- Schedule time with your CPA and legal advisor to talk about the business as an asset, not just as this year’s tax return or one-off issue.
- Block one hour on your calendar for a focused discussion on a legal business checkup, so this does not slide down the list again.
You do not need all the answers right away. You do need a clear starting point and a small set of next steps.
Ongoing Support That Matches Your Reasons
Some owners only want help with a specific contract or dispute. Others want an outside legal partner who knows the business, the players, and the long game. Outside Chief Legal works as ongoing counsel on a subscription basis for owners who want prevention-focused support and a consistent sounding board as they grow.
That model fits especially well for leaders who say things like, “I want to grow this to sell,” “I want this to run without me,” or “I want to protect my family and my team while we scale.”
Bringing It Back To Your Why
None of this is about loving legal documents. It is about the reasons you had when you signed your first lease, hired your first employee, or put your name on the door. Outside Chief Legal is here for all of those reasons: freedom, income, legacy, impact, family stability, and a company you are proud of.
If you want to see how well your current setup lines up with your real goals, book a Risk-Free Strategy Session to get a proactive legal review focused on why you started, not just where you are stuck today.
Our Corporate/Business Counsel Services
Outside Chief Legal LLC is a modern, forward-thinking law firm serving as fractional chief legal officers and outside general counsel for businesses and their owners. With over 200 years of combined litigation, in-house, general counsel, and administrative legal experience, the firm delivers approachable, comprehensive counsel that blends legal expertise with practical business insight to help clients navigate ownership complexities with confidence. OCL is a trusted partner for founders, business owners, and leadership teams nationwide. Learn more about our firm, meet our team, or schedule a Risk-Free Strategy Session to talk with an attorney about how we can help your company.
