Entrepreneurs — A Field Guide

Serial Entrepreneur:

Cannot, will not stomach the idea of working for someone else. Starts companies on the regular—some succeed, some fail. Learns from experiences and applies lessons to the next gig — which is always just around the corner, spurred by today’s latest great idea. Example: Used to run a neighborhood flower-delivery service until allergies made her quit. Now operating a lunchtime taco truck that sells Tex-Mex to hungry workers downtown, but has a great idea for an online clothing company that will sell stylish, lower-priced work attire to all the badly dressed office drones who crowd the taco truck every day at noon.

Weekend Entrepreneur:

Part-time businessperson who still holds a regular day job. Hasn’t been able to secure funding yet and isn’t entirely sure she wants to make the leap until she’s more confident of success. Example: A sales clerk at a big department store with an artistic streak. Having learned a decent amount about retail, both brick-and-mortar and online, she has a small side business making beautiful handmade scarves in her spare time and selling them over the Internet.

Forced Entrepreneur:

Can’t find a job; has no choice but to create his own. Example: A 25-year-old who once had a decent job with a local alternative newspaper but was let go last year when the economy tanked. Has talent and ambition but doesn’t have the experience or connections to get a new gig he likes. So he sets up an online neighborhood-listings guide and classified-ad network for people just like him — using low overhead and his own local knowledge to take on his former employer at its own game.

Social Entrepreneur:

Starting a nonprofit to help promote a pet cause; seeking only to draw a small-but-livable salary to make the effort worthwhile. Example: Former Peace Corps volunteer taps her connections to import slightly lower-grade fair-trade coffee beans from Ethiopia; sells them to U.S. customers, both online and in a small local shop, with most of the proceeds going to several humanitarian organizations.

Specialist Entrepreneur:

Has an in-demand skill that could be used to set up a business rather than just making money for someone else. Example: A gifted Web and graphic designer at a gigantic publishing house also designs cards, stationery and letterhead for friends as a favor. She prepares an exit plan for months and then quits her job. She sets up her own boutique out of her apartment and poaches a few carefully selected clients (with whom she enjoys a good personal relationship) from her former employer, undercutting the big firm by offering the same service as before at a fraction of the cost.

Solopreneur:

Prefers to be a one-man band, now and forever. Staff meetings? Small talk around the coffee machine? Coworkers who don’t flush? Screw that! Example: A former bus boy, waiter, and host who loves the culinary industry but can’t stand the hours, the stressed-out colleagues or the rude customers who leave bad tips. So he sets up a restaurant consultancy, vowing to take on just one client at a time, helping prospective restaurant owners with every aspect of opening an eatery— from choosing the décor to finding staff and purveyors.

Web-Driven Entrepreneur:

A hybrid of the Forced Entrepreneur and the Specialist Entrepreneur. Those who find themselves surprisingly able to take advantage of the Web — its technologies, its economies of scale, its viral capabilities, even its free or inexpensive continuing-education courses — to do what they never thought possible: open their own business. Example: An English major just out of college who never considered going to business school and hasn’t read any management books takes a three-month online course in marketing and soon starts a modest online consultancy to help other young small businesspeople promote their enterprises. Not tethered by geography, he soon signs up clients all across the country; work is done via e-mail, cellphone, and the computing cloud.

Second-Generation Entrepreneur:

Someone who takes over a modest family business and transforms it into something far greater than what it’s ever been before. Example: A young guy assumes day-to-day control of his family’s small neighborhood plumbing business when his father decides he wants to stop spending so much time running it. The son sets up a Website for the first time and also begins advertising online and around the neighborhood much more than his father ever did. Increased business from those modest efforts soon enables the son to expand the staff, upgrade service vehicles, and pay for continuing education so that he can branch out into electrical work as well.

Entertainment Entrepreneur:

Someone who works at a bar or club several nights a week because he likes the scene, the connections, and the money, but knows it’s not likely to replace his day job any time soon. Example: An 9-to-5 worker aspires to become a record producer, so he takes a job D’ing at a club two nights a week. This hardly represents an all-out push to try to make it in the music business, but it’s a slow-and-steady way — tortoise, not hare — to gain entry into a preferred career while retaining the security (if also the tedium) of a day job.

At-Work Entrepreneur:

A person with no desire — or no current chance — to start her own business, but who applies entrepreneurial ideas and vigor to her day job in order to get ahead where others merely tread water. Example: A woman with a solid, decent-paying job at a midsize company who comes up with clever, creative ways to maximize productivity and make herself and her department more efficient and better at what they do. The lessons she learns and the skills she gains will be invaluable should she decide to start her own business at some point in the future.