Should I Sue? The Founder’s Perspective

Dane Fogdall

March 5, 2026

Intro

For founders, one of the most stressful and frustrating experiences is when an agreement you made with someone is broken. It could be a supplier, customer, co-founder, or employee who broke the agreement, but the result is the same: you relied on someone and now they’ve put you in a difficult position. Perhaps you’ve lost out on business, your IP has been infringed upon, or your business’s function is being threatened. You might be thinking: is it time to sue?

Savvy founders want to and do enforce their rights, and a key method of doing so is through litigation. However, litigation is a significant step to take, so  as founders it’s important to ask not only “Can I sue?” but also, “Should I and what impact will this have on the startup?” 

Founders should consider the following five factors before undertaking litigation. These factors ensure that suing is the smart path to walk and will put the business in the strongest position going forward. 

Factor 1: Merits of Your Claim

Whether or not you have a strong legal claim is crucial to determining if you should pursue a lawsuit, as a weak litigation claim  will only absorb business resources.

Ask yourself the following when considering the merits of your particular claim:

  • Do you have a valid and enforceable contract? A written contract is stronger evidence than an oral contract or a handshake deal.
  • Can you demonstrate that you performed your own obligations under the contract or justify why you didn’t perform?
  • Is the other side’s conduct a clear failure to perform their obligations? Your dissatisfaction or a change in circumstances won’t suffice here.
  • Can you prove actual damages caused by the breach? Did you lose revenue, was there an extra cost, or delay, not just annoyance?
  • Does the other side have obvious defenses?

Factor 2: Money and Economics

Even if you have a strong claim, litigation may not make economic sense. It’s important to consider the following:

  • What is the size of potential damages you may receive? It’s possible that you may not receive much financially for the breach.
  • Can the other side be collected from? Even if you win, will the defendant, insurance or their assets actually be able to pay?
  • What is your budget for litigation? Legal fees, experts, discovery, appeals, and internal time devoted to the litigation can be substantial and pull your focus away from your operations.
  • What will the impact on your runway, credit and investor perception be? If cash is diverted into a lawsuit rather than developing the business your ability to raise may be impacted.

Factor 3: Business and Relationship Impact

In the marketplace, your relationships can be critical to your success and preserving them and your reputation can be paramount. Ask yourself the following when considering the reputational and relational impact of litigation:

  • Is the other side a mission-critical partner? Would suing destroy the relationship?
  • What signals does litigation send to the market?
  • Will this litigation impact future deals?
  • What will the significance be of internal distractions to your business?
  • What risks to your reputation exist if there is public litigation?

Factor 4: Alternatives

Litigation is a major step and often a serious escalation. There are alternatives to suing that may be a better fit for your situation, when considering a lawsuit consider the following alternatives as well:

  • A Pre-suit demand letter. This will test the other side’s risk tolerance, start a paper trail, and potentially prompt a voluntary resolution from the other side.
  • Negotiation. A negotiated amendment or work-around to a breached contract.
  • Mediation rather than trial. This resolution method is typically lower cost and confidential.
  • Contractual or ad hoc arbitration. This process can be faster and confidential while being binding; however, there may be significant financial cost akin to a trial.

Factor 5: Risk, Timing, and Strategy

In addition to the above factors, you should consider the following general risks and issues:

  • What’s your timeline/how long can you manage ongoing uncertainty? Litigation can take months or even years to fully resolve.
  • What’s your risk tolerance? Litigation is uncertain, trials can result in loss or low damages. 
  • Is there a need for the public resolution of a court, or is confidentiality more important?
  • What else is happening with the business? Is there a potential raise occurring, or an ongoing merger or acquisition? Is this the right time to litigate?

Founder Takeaway

Litigation is always a big step, and founders should consider all relevant factors before making moves. However, there are times when you either have no choice or the benefits outweigh the risks. At Founders Law, we help founders navigate the contentious and difficult situations that lead to litigation, providing counsel both as lawyers who specialize in startup law as well as corporate litigation. Our goal is to help founders make informed decisions, and when necessary, litigate on their behalf so they can succeed and grow their business.

More Insights & Articles

VC & Startup
March 2, 2026

What Form of IP Protection is Right for You and Your Start-Up

As a founder, one of the most valuable assets you possess is your intellectual property: your ideas, technology, inventions, business practices, and branding. Early on, this is often all a startup really has, and it’s often the basis of your pitch to potential investors.
January 17, 2026

Founder Control, Board Governance, and Voting Power: What the Chicago Bears Teach Startup Founders About Dual-Class Stock and Long-Term Control

The Chicago Bears are often discussed as one of the NFL’s most historic franchises. From a corporate governance perspective, however, the Bears look far less like a traditional sports team and far more like a founder-controlled company. For more than a century, ownership and decision-making authority have remained within the hands of the Halas family. That structure closely mirrors the way many startup founders seek to retain control of their companies’ cap tables and boards even as outside investors come in and enterprise value scales into the billions.
VC & Startup
December 16, 2025

Do You Need a Holding Company? A Founder’s Guide

Understanding whether a holding company is right for your venture—and how it works—can provide a significant advantage in scaling your business safely and strategically.
November 18, 2025

Controlling your IP Means Controlling Your Future: What Stephen Curry’s Under Armour Split Teaches Founders About Brand Ownership

Stephen Curry’s recent split from Under Armour after more than a decade of partnership highlights a simple truth. Control of your intellectual property is control of your future. For founders, IP is often the most valuable asset they will create. It determines leverage, long-term valuation, and whether the brand they built remains theirs as the company grows.
VC & Startup
November 4, 2025

Founder Equity Splits & Re-Splits: Getting It Right Before You Raise

Getting your founder split right (and fixing it when it’s not) is one of the most important legal and governance steps before your first institutional raise. At Founders Law, we advise clients to treat equity structuring as a living process—something that should evolve with the company rather than remain static. Here’s how to think about it pragmatically, and what to do if the original allocation no longer fits your company’s reality.
November 3, 2025

Who We Are: The Law Firm for the Founder of the Future

We’re a next-generation law firm built for the realities of the modern founder: fast-moving, resource-conscious, and navigating technologies that are transforming every industry. Our practice combines experienced legal insight with proprietary automation tools that eliminate inefficiency while preserving the substance and nuance of real legal work.
VC & Startup
October 26, 2025

How Venture Capital Evaluates Quantum IP Portfolios

In quantum computing, intellectual property is the business model. Unlike software startups, which can iterate toward product–market fit, quantum companies are capital-intensive, research-driven, and often pre-revenue for years.
VC & Startup
October 25, 2025

Intellectual Property for Quantum Startups: Building Defensible Innovation in a Non-Classical World

Quantum computing has reached the transition from laboratory research to commercial deployment. As superconducting, photonic, and ion-trap systems mature, founders are discovering that while the physics is complex, the law can be even more so.
VC & Startup
October 24, 2025

Equity Incentive Plans: Because Team Retention Requires More Than Free Pizza

Equity incentive plans (“EIPs”) are legal frameworks that allow companies to grant equity-based compensation to their executives, directors, and employees. These plans are particularly valuable for startups that want to attract top talent without paying high salaries in the early stages.
VC & Startup
July 2, 2025

Negotiating a Founders’ Agreement

Negotiating a legally-binding agreement between co-founders that determines, in advance, what will happen in a variety of situations where co-founder disputes often occur can be the difference between your startup failing or succeeding.
VC & Startup
May 16, 2024

Data Rooms and Due Diligence: Raising Capital from Investors

The data room is one of the most important aspects of the due diligence process of any fundraising round.
VC & Startup
April 15, 2024

The Big FAQs About TOU

TOU are a set of rules and guidelines that govern the use of a website, app, or online platform
VC & Startup
March 27, 2024

Operating Agreements for LLCs

The operating agreement directs the internal mechanics of the business and aligns the goals of its members by contractually binding them to its terms.
VC & Startup
March 13, 2024

The Art of Startup Resilience: Surviving and Thriving in a Bear Market

Ten ways that startup founders can stand out and get access to capital in a bear market.
VC & Startup
March 4, 2024

Understanding Equity Rounds: A Primer on Pre-Seed vs. Seed vs. Series A

In order to secure the proper funding, founders must first understand how the different financing rounds typically work.
VC & Startup
February 8, 2024

83(b) Elections: Advantages & Disadvantages

Individuals who own equity in a startup face uniquely complicated tax issues that require efficient strategies to minimize immediate and future tax liability.
VC & Startup
January 31, 2024

Seller Financing in Sale Transactions

While it involves more risk, seller financing can be very beneficial for all parties involved.
VC & Startup
January 29, 2024

Delaware C-Corporations: The First Choice for Founders and Investors

For startups looking to sustainably grow using equity funding, founders should seriously consider the default of a Delaware C-Corporation.
VC & Startup
October 31, 2022

What is a Certificate of Incorporation?

A Certificate of Incorporation (also known as a charter) is a document that establishes the legal existence of a corporation.
VC & Startup
October 17, 2022

Playing it "SAFE" with Pre-Seed Financing

For those founders seeking pre-seed investment to fund this period of validation, a “SAFE” – or, Simple Agreement for Future Equity” – can be an ideal mechanic.
VC & Startup
October 17, 2022

Term Sheets - A Crucial Brick in a Solid Foundation

When used correctly, term sheets can shorten deal cycles, prepare the company for future rounds, and limit legal spend on both sides of the deal.