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 while every CEO is one-of-a-kind, there are some patterns that emerge. No matter what industry they’re in, most founders I’ve met fall into one of a few categories. I think of them as the Corporate Survivor, the Impresario, the Classic Entrepreneur, and the Local Legend.

The Corporate Survivor: Been There, Done That

“Sales strategy? I just call my 5 best friends, who are all Fortune 50 CTOs.”

The Corporate Survivor has spent years climbing the proverbial ladder, and has the war stories to prove it. After decades of PowerPoints and politics, these seasoned leaders are finally free to work on their own Big Ideas. Organization and process come naturally to them, and they know what it takes to attract and manage the best talent.

What their business looks like: Corporate Survivors aren’t usually disruptors. Instead, they create incremental solutions for specialized markets. These founders often begin with the end in mind, starting their company with the express goal of selling out in a few years. Many of them already have the relationships that will help them get bought up by a private equity fund, or by a large multinational in their industry.

Corporate Survivors’ companies tend to grow slowly and steadily once they have a critical mass of customers. Often, they bring their semi-retired executive friends along for the ride, hiring them as consultants.

Where to find them: In their well-appointed home office, on the road nurturing their network, or celebrating milestones with their team and/or extended family (who are frequently the same people).

Their superpowers: They’ve earned deep insights and a broad perspective by living through their market’s wildest ups and downs. They don’t lack for capital, since they’re able to tap into their substantial savings – or better yet, their old colleagues – for financial support.

Their kryptonite: You can take the founder out of the big corporation, but sometimes it’s hard to take the big corporation out of the founder. Hour-long meetings and decisions by committee may feel like the right way to manage after decades in a huge multinational, but these habits can turn into distractions that slow a small company to a crawl.

The most successful Corporate Survivors figure out how to internalize the pace of startup life, leading with urgency as well as precision.

The Impresario: The Ultimate Portfolio Career

“So as soon as my venture studio gets funded, I can lease the podcast equipment for my co-work building, you know, where I host the weekly crypto meetup.”

If you ever met a designer-marketer-researcher-consultant with 4 different business cards, you met an Impresario. You may be following one online right now. If something’s trending today, you can bet they were posting about it a month ago. By their 30^th birthday, this eclectic character has typically launched multiple LLCs and maybe a nonprofit or two.

What their business looks like: Digital natives and opportunistic in the best way, Impresarios are building the things we’ll all want tomorrow. Their projects can look less like a company and more like a loosely connected ecosystem. They often stay solo for as long as possible, hiring contractors only when it’s time for a growth sprint.

An Impresario may have multiple entities that supply each other with goods and services, or collaborate to bring different ideas to life. Consulting companies, co-working spaces, art collectives, and venture studios are all good fits for Impresarios, letting them explore different areas of interest and make novel connections. An Impresario’s business plan may be hard to explain on a bank loan application (and if we’re honest, much of it is running on vibes) but somehow it all works.

Where to find them: Ubering between meetings, headlining at a tech conference, or adventure traveling somewhere you never heard of. Don’t worry if you miss them; there’s a good chance they’re streaming their day in real time.

Their superpowers: Boundless energy, a nose for finding and monetizing the next new thing, and a knack for inspiring others to follow (and fund) their visions.

Their kryptonite: “Wow, I love that question. I was talking about that yesterday on my podcast with this author who won a Pulitzer last year. Let me just send this text, it’s my head of sales. Oh hey, I have to get on a Zoom with the investors. Sorry, you were saying?”

Impresarios do best when they partner with skilled operators who can pull the founder’s ideas into the realm of reality and profitability.

The Classic Entrepreneur: Their Own Boss From Day One

“And I want it closed by the end of the week.”

This is who we normally think of when we picture a founder. Classic Entrepreneurs never had a regular day job, or maybe they worked in an office that one year and swore to never do it again. They were the ones selling candy out of their backpack in grade school, coding their own apps in high school, and skipping the college career fair because they already had a payroll to manage.

These founders are inseparable from their company, and vice versa. Unlike Impresarios, who often juggle multiple ventures, Classic Entrepreneurs commit to one business idea. They eat, breathe, and sleep their industry. They’re fluent in finance and excellent managers – at least for workers who are willing to go above and beyond for the business.

What their business looks like: Lean, hungry, and optimized, these companies shine in niche markets. Every employee in the company knows how they contribute to the bottom line. The company stock is closely held by the founder and a handful of trusted lieutenants, but in good years, profit flows freely to high performers.

Classic Entrepreneurs are masters of building deep expertise while staying alert for expansion opportunities. Although the Classic Entrepreneur is deeply attached to what he or she has built, selling the company is always an option if the price is right.

Where to find them: Powering through a 10-hour day of 15-minute meetings, then pitching clients over dinner and drinks. A regular at industry events, and if they’re at an awards ceremony, they probably won it.

Their superpowers: Endearingly relentless, Classic Entrepreneurs close their deals on time and under budget by any means necessary. Their conversation is utterly devoid of BS – and sometimes low on niceties, since they have zero fear of conflict.

Their kryptonite: Tight deadlines, strict budgets, and startup energy aren’t for everyone, so finding the right talent at the right price can be hard. Even with great employees, delegation can be a challenge for CEOs who are used to managing everything themselves. These dynamics can combine to trip up Classic Entrepreneurs, creating hiring gaps and missed opportunities.

As their companies grow, these founders will need to create an entire level of management under them to handle day-to-day work. Getting a little distance from the company they built will help them refocus, strategize, and lead their teams to new heights.

The Local Legend: Keeping It Close To Home

“So when Bob and I bought our first building here in 1989…” 
(only later do you realize that Bob has a street named after him and is your Congressman’s dad)

Local Legends are the community leaders, homegrown franchises, and mom-and-pop shops who serve our day-to-day needs. Whether they inherited family businesses or started from scratch, these entrepreneurs are re-imagining Main Street for the next generation.

Most business owners are passionate about their industry, but these founders are the most likely to give an uninterrupted 20-minute lecture on the intricacies of their job – and specifically, how it relates to their neighborhood. If you listen carefully, you can hear the whole history of their city or county in their stories.

What their business looks like: Beloved hometown institutions, these small LLCs, corporations, and DBAs are usually closely held. Outside investment investment is limited; capital comes from loans, and many of these companies are bootstrapped. While their target markets are tiny compared to those of most startups, their customers are fiercely loyal.

These kinds of companies also grow slowly, so they operate like early-stage startups for longer. The owners are more likely to wear many hats, with creativity at a premium because income, and therefore budget, is unpredictable.

Where to find them: Sponsoring a local charity’s 5K run, in line for coffee at a Chamber of Commerce breakfast, or chatting with you as they ring you up at the register.

Their superpowers: These business owners have years (sometimes decades) of experience in their communities. They don’t need algorithms to tell them what their customers want, because they talk to them every day.

Their kryptonite: Local Legends are sometimes not as tech-savvy as some of their CEO peers. This is understandable; for them, buying into the latest trends can be prohibitively expensive and just plain unnecessary.

That said, many of these bosses would benefit from doing one or two low-cost tech experiments per year. Smart uses of software or online marketing might even give them an edge over some of their big-box competitors.

Celebrating All Types Of Founders

Whether you’re a strategic Corporate Survivor, visionary Impresario, tireless Classic Entrepreneur, or community-rooted Local Legend, you bring something unique to the table. Your history, instincts, and personality are all part of your edge, and will leave a mark on your company for as long as it’s in business. Whatever it is you’re building, I can’t wait to see what you do next.

Do you see yourself in one of these founder types? Every business has its own legal needs — and we’re here to help you meet them. Contact us if you’re a founder or business owner located in New York or Massachusetts and looking for advice on corporate or transactional matters.