Tuesday, 14 October, 2025

From Bootstrapping to Wall Street: The Legal Maze of Startup Fundraising


Reading Time: 5 minutes

By Michele Cea, Partner, Cea Legal L.C.

 

Introduction

 

In the high stakes world of entrepreneurship, raising money isn’t just about convincing investors to believe in a vision. It’s also about navigating an increasingly complex legal landscape that can determine whether a company thrives, or stumbles before it reaches scale.

 

This guide traces the financing journey of startups, from the beginnings of bootstrapping to the high-profile leap of an IPO, while unpacking the legal complexities that accompany each stage. It aims to help founders grasp the capital options, the trade-offs they entail, and the agreements that formalize those deals.

 

Bootstrapping / Friends & Family

 

To begin, there are three main goals. In order to validate assumptions quickly and cheaply, it is imperative to launch a minimum viable product (MVP), which is the simplest version of a product that can be released to the market to test whether people actually want or need it. Secondly, by launching an MVP, founders can gather real feedback from users, measure interest, and learn what works (or doesn’t).

 

Let’s say you’re building a food delivery app, the MVP would be a simple website where people can place orders from a limited menu. If enough customers use it and like it, then expand with features like live tracking, mobile payments and restaurant reviews.

 

Thirdly, begin assembling a basic team to create a foundation that moves your idea from concept to company. To fund this, entrepreneurs mainly turn inward to personal savings, or family and friends. The typical investment range ranges from $1,000 to $100,000.

 

Even at this stage, the legal paperwork matters. Some founders structure contributions as loans with promissory notes, essentially a legally binding contract where the borrower promises to repay the lender. Others use SAFEs, a legal agreement that allows an investor to purchase equity in a startup at a future date. Early investors receive minimal formal rights, founders should communicate risks and avoid overpromising. However, if equity is offered, cap table dilution should be tracked from the outset. Sometimes, convertible notes are used, which are a type of loan that gives investors the right to convert their debt into equity at a predetermined event. Historically, convertible notes are the most popular choice for early-stage investing, but SAFEs have become increasingly popular.

 

Angel Investment

 

At the angel stages, the goals shift toward finishing product development, landing the first paying customers, and sharpening product-market fit, often while rounding out the founding team. The typical investments range from  $25,000 and $500,000, and are sourced from high-net-worth individuals and angel networks. Deals are usually structured through convertible notes, SAFEs, or, in some cases, direct stock purchase agreements. Angels may ask for modest rights, such as advisory input or basic financial updates, but compared with later-stage venture capital, the terms remain relatively founder-friendly.

 

Seed Stage

 

By the time the startup reaches the seed stage, the ambitions and the stakes have grown. Founders are no longer just testing ideas; they are expanding their teams, building tractions in the market, and laying the groundwork for institutional investment. The main capital sources are seed funds, angel syndicates, and early-stage VCs. The typical investment ranges from $500,000 to $2,000,000, enough to fuel hiring and establish repeatable sales and marketing strategies.

 

A common legal agreement is a preferred stock purchase agreement, which is a formal legal contract between a company and investors of its preferred stock. Another is investor rights agreement (IRA), sets out the rights and obligations of the company and the investors and covers registration, information, and preemptive rights. The Founders’ Stock Restriction Agreement refers to the equity interest that is issued to Founders at or near the time the company is formed. Equally as important, there are two main types of leading cap table management software platforms that help startups with equity administration, compliance and fundraising. Carta offers a free plan for early companies but becomes costly as you scale, while Pully is known for flexible, transparent pricing and user-friendly interface for growing companies. It is important to note that preferred stock at the seed stage, typically carries terms such as 1x non-participating liquidation preference, guaranteed board representation, anti-dilution protections, and a suite of major investor rights.

 

Series A – Growth Stage

 

By the time a company reaches its Series A round, the conversation shifts from survival to scale. The goals are no longer about proving the product works but about building revenue, expanding market share, and putting serious operational and compliance systems in place. The capital now comes from institutional venture firms, with investments that often stretch from $2 million into the tens of millions. The paperwork grows into complex, too: companies adopt Amended and Restated Certificates of Incorporation, issue Series A Preferred Stock, and put in place detailed voting agreements and employee stock option plans. Investors come armed with protections such as veto rights on major decisions, rights of first refusal, drag-along rights, and a suite of mandatory reporting requirements. And with board seats increasingly occupied by venture appointees, the company takes on a more formal, institutional character, reflecting the higher stakes of growth.

 

Series B/C/D – Expansion & Maturity

 

At Series B, C or D rounds, the ambitions are unmistakably larger: expansion into new markets, strategic acquisitions, and sharpening profitability, all while laying the groundwork for an eventual sale or IPO. The capital is sourced from late-stage venture funds, growth equity firms, and sometimes corporate investors, with check sizes easily ranging from $10 million to well over $100 million. Legal agreements are increasingly sophisticated, covering new preferred stock issuances, updated voting and information rights, and co-sale provisions. The balance of power tilts toward investors, who often secure senior liquidation preferences, stacked payout rights, and pay-to-play provisions. Governance, too, becomes more intricate, as larger boards and multiple classes of stock formalize decision-making in ways that reflect the company’s maturity, and the heightened stakes at this stage.

 

Private Equity / Pre-IPO Rounds

 

In the final stretch before going public, companies often turn to private equity and crossover funds for capital injections that can range from $25 million to half a billion dollars. These rounds are less about proving growth and more about consolidating financials, tightening compliance, and shaping the executive bench to meet the scrutiny of public markets. The legal background becomes more muscular, with recapitalization agreements, voting trusts, and registration rights forming the framework. Investors at this stage may push

for majority control, swap in new management, and enforce stricter governance standards. Exit strategies are written into the fine print, complete with drag-along provisions and staged liquidity rights.

 

IPO – Initial Public Offering

 

Finally, an initial public offering (IPO) is the moment a private company steps onto Wall Street, raising hundreds of millions of dollars while giving early backers a chance to cash out. It also marks the start of life under far stricter rules: companies must file detailed reports with the SEC, answer to new boards and audit committees, and disclose their earnings every quarter. The process is managed through underwriting deals with banks, regulatory filings, and lock-up agreements that keep insiders from selling too soon. For founders and investors, it’s both a windfall and a turning points as the company now answers not just to venture capitalists, but to the public markets.

 

 

 

Michele Cea is a founding member of the firm. Mr. Cea graduated from Catholic University School of Law in Milan, Italy (J.D., 2009, with honors), and Fordham University School of Law in New York (LL.M., 2011, Cum Laude).

Prior to completing his LL.M at Fordham Law School in 2011, Mr. Cea worked in a boutique Italian corporate law firm, where he was primarily dealing with shareholder agreements and various business transactions. In New York, Mr. Cea collaborated as a foreign attorney with a preeminent white-collar law firm in matters related to financial frauds, securities regulation and corporate compliance, among others. Mr. Cea was also employed as an Associate in the New York office of an International law firm, where he represented European clients operating in the U.S. In this position, he gained a valuable experience in the business law and real estate practice area, including corporate formation and dissolution, commercial transactions, residential and commercial real estate, trademark registration and business immigration.

Mr. Cea founded his own practice focused on representing foreign nationals and companies operating in the United States. He has extensive experience with international corporate matters, real estate transactions and  non-immigrant visa petitions, such as extraordinary ability and investor visas.

Mr. Cea is licensed to practice in New York (2013) and in Italy (2012). Mr. Cea is fluent in Italian and conversational in Spanish. Mr. Cea is a member of the New York City Bar Association, the New York State Bar Association.

Learn more at https://cealegal.com/.

 

Connect with Michele Cea on social media:

Instagram: https://www.instagram.com/cealegalnyc/

LinkedIn: https://www.linkedin.com/in/michelecea/

 

 

Check out more business stories here. 

Explore more insights at https://dailybusinessjournal.com/.

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