“What’s measured is managed” is an often-repeated business saying. When it comes to contracts, many small businesses aren’t measuring enough to manage for the best results. If your contracts process feels like a black hole where deals disappear for weeks, or you keep having the same internal debates about wording,…
When you’re a startup or small vendor negotiating a services agreement with a larger customer, “mutual” contract language may sound fair. But it can quietly shift disproportionate risk onto you. Here are three interrelated areas where this dynamic shows up most often: indemnification, limits of liability, and confidentiality. How Mutual…
NDAs aren’t usually more than a few pages long. They tend to look simple and fair. You’re on a deadline, and the other side shows no interest in negotiating such a tiny document. So why is your lawyer marking it up and asking to get on a call? Can You…
When most people think of a pitch deck, they imagine a high-energy startup founder holding forth in front of a room full of venture capitalists. But pitch decks aren’t just for VC-funded startups. They’re for any founder who needs to persuade someone to give them money, time, or trust. If…
Most pre-seed companies don’t have enough operating history to show long-term success. Sometimes, founders focus on metrics that signal momentum: downloads, usage, or even social media followers. This is even more applicable in the ultra-competitive, fast-moving area of AI. Founders, like anyone, pay attention to what they’re tracking. That’s why…
Most startup founders and small business owners plan obsessively for growth. Very few plan for shutdown. However, the day may come when the best thing for a company to do is to stop operating. In New York, this means completing a sequence of approvals, tax clearances, filings, and clean-up tasks….
If your business is a New York corporation, you may have heard from an investor or advisor that you should re-incorporate in Delaware, a process known as a “Delaware flip.” Doing this can be useful in many ways, but sometimes adds cost and complexity without delivering real value. This article…
Many founders and small business owners treat contracts as a necessary evil: something you endure at the end of the sales process. In practice, your contract is an important part of the sales process. It signals how you operate, how you treat customers, and how easy it will be to…
Dilution isn’t automatically “bad.” Most business owners would happily trade 50% of a $1 million company for 5% of a $1 billion one. The practical question is: how much ownership will you have to trade away to build a real business in your sector, and how can you make each…
If you and one or more co-founders are starting a corporation in New York, you may hear that it’s important to have a “founders’ agreement.” However, you may not have to draft a separate contract to get the legal coverage you need. Your commitments to your co-founders and your company…
In How to Find a Business Lawyer: A Practical Guide, we looked at how to identify lawyers who might be a good fit for the work you have in mind. For your initial meetings with those lawyers, here are some talking points you can use to get the best possible…
Finding a lawyer who understands startups and small businesses isn’t always easy. That’s true even now, despite the marketing promises of legal apps and websites. This post is the first of two. Here, I’ll cover how to decide whether you actually need a lawyer right now, where to look, and…
Like everything else these days, early-stage investing is in the middle of a seismic shift. Angels are using AI to source most of their deals, spot patterns in business models, and predict the odds of a life-changing exit. So what’s next for startups who are fundraising, and how can founders…
Do you light up when you talk about product design or customer pain points—but your eyes glaze over when someone starts holding forth about Kubernetes or JavaScript frameworks? Are you worried about finding the right technical lead to build your product, when your last programming experience was printing “hello world”…
In a world of security theater and corporate doublespeak, “we care about your privacy” is often just a tagline. Still, I’m hopeful that respecting customers’ privacy can be part of a viable business strategy, creating user trust and even driving sales. I’m inspired by clients who are building privacy-friendly apps,…
It’s no secret that as your company grows, you accumulate more contracts, and the contracts become more complex. Keeping track of all these agreements and understanding how they all relate to each other can become a daunting task. Without a system to manage your contracts, you may be risking missed…
Over the years, I’ve had the privilege of working with founders from all walks of life. They hail from New York City, the rural Hudson Valley, and everywhere in between; they represent age groups from Boomers through Gen Z; and they’re building everything from brick-and-mortar stores to virtual-only empires. And…
Every so often, clients send me a contract template they’ve come up with themselves. It may be a copy-and-paste from the leaders in their market, or something they used at another company and liked. Once, I was sent 3 separate templates so I could “pick the best wording from each”…
Disagreements between founders can be a huge drag on any new company. You’ve probably heard some cautionary tales, whether it’s Apple’s origin story or drama from local business owners. Before you launch your own company, be sure to ask your co-founders these pointed questions about how each of you will…
They may call themselves brokers, consultants, or facilitators. They say they know angels or VCs who are eager to invest in your company. In today’s challenging fundraising climate, it can be tempting to listen to their pitches. But before you do, be aware that paying someone to contact investors on…
As a startup or small business, it can be exhilarating to win a sale with a huge multinational. However, once the reality of contract negotiations sets in, you may wonder what you’re signing up for, literally. Large companies, especially in highly regulated industries like finance or healthcare, may want to…
As a founder raising seed capital, you know your revenue numbers inside and out. But can you convince investors that this revenue is sustainable? Angel investors are looking for companies that can deliver returns of 10x or more on their money. To show them you can scale profitably, you need…
Downtown warehouses vs. midtown highrises. All-night coding sessions vs. all-day meetings. Hoodies and flip-flops vs. business casual. At first glance, corporate managers and startup founders look like they come from different worlds. But doing time in a large enterprise can actually help you become an outstanding startup CEO. Advantage 1:…
As a B2B startup or small business, you’re looking to cast a wide net for potential clients. Whether you’re selling to medium-sized companies or multinationals, you need proven methods for reaching decision-makers. These may be C-level executives or senior managers, and they’re the ones with the budget and authority to…
An online search will tell you that data is “the new sand,” “the new oil,” “the new currency”, or maybe even “the new gold.” Although it may be hard to define data’s exact value, more and more small businesses are starting to exploit this resource to impress customers, grow sales,…
“We decided to go in another direction.” “We’re having budget issues.” “Your project sponsor is no longer with the company.” No matter how gently your client breaks the news, it’s painful when a pilot project fails. Your company was hoping for a successful proof of concept, or maybe a profitable…