Linda Rottenberg got into a taxi in Buenos Aires and discovered that her driver had studied engineering. This was the sort of detail another passenger might have filed away between checking the fare and finding the right address. Rottenberg wanted to know why he was driving a cab. Why had he not started a business? In her retelling, the conversation stalled over the very idea of an entrepreneur. The driver had an education. What he lacked was a plausible route from that education to a company of his own.
She has told the story for years, and its force lies in that mismatch. A person can have the ability to make something without having the connections, money or examples that make the attempt seem reasonable. Rottenberg was becoming preoccupied with the people who occupied that gap. The celebrated garage founders of American technology were an awkward model for someone without investors, useful introductions or, for that matter, a garage. An origin story imported from California could be inspiring and still offer very little help on Monday morning.
In 1997, Rottenberg and Peter Kellner co-founded Endeavor. Their proposal was to identify promising entrepreneurs in emerging and underserved markets, connect them with people who could help, and stay involved as their businesses grew. Argentina and Chile were the starting points. She remembers sketching the plan with Kellner on a napkin at her parents’ kitchen table in Boston. It is a nicely inconvenient detail for anyone who thinks the proper birthplace of an ambitious organization is an expensive office. The kitchen already had chairs.
A law degree, an unexpected departure
Rottenberg grew up in Newton, Massachusetts, in a family she describes as giving her permission to be curious. At Harvard, she studied social studies and encountered Joseph Schumpeter’s account of entrepreneurs as agents of economic change. Her student activities ran toward causes: she organized for the Dukakis presidential campaign and became Harvard’s first campus recruiter for Teach for America. She was interested in getting people to do something together. The object of that interest would change; the habit would remain.
Yale Law School supplied another credential and a useful discovery: she did not want to practice law. She graduated in 1993. Rather than follow the familiar sequence of clerkship, firm and settled profession, she went to Latin America, worked on legal education and later joined Ashoka, the organization supporting social entrepreneurs. Bill Drayton, Ashoka’s founder, became a mentor. The work brought her close to people using enterprise to change their communities, while leaving her wondering who would help ambitious founders build larger private businesses.
There is a particular freedom in realizing that a respected qualification does not oblige you to use it in the expected way. There is also the small matter of explaining this to your parents. Rottenberg’s career took shape through that friction between a reassuring résumé and an unreassuring plan. She had learned how institutions worked. Now she wanted to assemble one around people whom existing institutions were passing over. It required more than an argument about potential. She needed examples that other people could recognize.
A sheep farm enters the conversation
One early example was Wences Casares, who grew up on a sheep farm in Patagonia and wanted to build an online financial business. Local investors had rejected him. Endeavor helped him find capital and a chief operating officer for Patagon.com. Its sale to Santander became an early demonstration of the possibility Rottenberg had been describing. A founder from an unexpected background had built something that a major financial institution wanted to buy. The old objections became harder to repeat with a straight face.
Officenet, founded by Andy Freire and Santiago Bilinkis, offered another kind of example: office supplies. The business was a reminder that useful entrepreneurship need not arrive wearing a futuristic costume. There were ordinary commercial problems to solve, and substantial businesses to build around solving them. Endeavor brought founders into contact with experienced businesspeople who could help them think beyond the limits of their immediate surroundings. The introductions were practical. The public examples did a second job, changing what other aspiring founders thought they were allowed to attempt.
Rottenberg became known as “Chica Loca,” the crazy girl. She kept the nickname’s provocation and eventually turned it into the title of a book. There is wit in making a critic do your marketing, but the joke had serious work underneath it. Endeavor needed founders willing to dream beyond the local consensus and mentors willing to examine those dreams. An encouraging speech could get a person moving. An introduction, an experienced adviser or a better hiring decision could help keep a company moving after the speech was over.
“Crazy is a compliment!”
Linda Rottenberg
The second company is part of the first
Endeavor’s organizing idea eventually acquired a name: the Multiplier Effect. A founder builds a successful business, then mentors another founder, invests in a new venture or trains employees who later start companies. Success begins to travel through relationships. Rottenberg has argued that these connections deserve attention alongside revenue and valuations. They help explain how a place with a handful of conspicuous companies can develop a broader community of people capable of building the next ones.
That changes the question asked of a successful entrepreneur. How much value did the company create? Who else became capable of creating value because it existed? The second question takes longer to answer. Endeavor has mapped relationships among founders to make those less visible contributions easier to see. A mentor’s conversation does not ring an opening bell. An employee’s later business may carry a different name. Yet both can belong to the afterlife of the original company, spreading knowledge and confidence beyond its own balance sheet.
The organization’s structure reflects its preference for people who know the terrain. Local business leaders help fund offices and build mentoring networks; selected entrepreneurs gain access to an international community. Endeavor concentrates on the scale-up phase, when a business has already established a model and needs help growing. In 2013, it began opening U.S. affiliates as well. Underserved places were hardly confined to distant countries. In 2018, Rottenberg received the Heinz Award for Technology, the Economy and Employment, recognizing this work connecting entrepreneurship with economic opportunity.
When the mentor also writes a cheque
Mentorship could open doors, but entrepreneurs also needed investment. Endeavor Catalyst launched in 2012 as a rules-based co-investment vehicle. The change brought a nonprofit supporting founders into direct financial participation in their companies. Rottenberg has described the transition as the hardest of her career. Some board members worried about the organization drifting from its mission. The entrepreneurs wanted it to invest. Building an institution meant facing disagreement inside the institution, too.
The fund made the relationship more concrete: Endeavor could support founders and share in their companies’ success, with investment returns helping sustain its work. In the organization’s 2022 impact report, Rottenberg described Catalyst as part of the effort to become self-sustaining. It is an unusually literal version of paying success forward. The businesses receiving support can help finance support for others. The model depends on actual companies doing well, rather than on an endless supply of persuasive speeches about what they might someday achieve.
There are limits to what a headline number can explain. Assets under management belong to an investment vehicle; revenues belong to entrepreneurs’ companies. Neither is Rottenberg’s personal fortune. Her work sits among those businesses, funds, advisers and local teams. It is the work of making a useful relationship possible, then making it repeatable. Her current public biography also lists board roles at Globant and Pershing Square SPARC Holdings, and advisory work at Yale. The former student who wanted an unconventional route now helps other people navigate theirs.
Crazy, with a sensible pair of shoes
Her 2014 book, Crazy Is a Compliment: The Power of Zigging When Everyone Else Zags, took the lessons beyond Endeavor’s selected founders. Its audience included people working inside companies, nonprofits and small businesses. Rottenberg’s argument was that entrepreneurial habits could be useful without everyone quitting a job to create a technology startup. The practical problem was how to take a chance without turning an entire life into collateral. “Crazy,” in this account, could coexist with caution about what one stood to lose.
The book became a New York Times bestseller and appeared in Spanish, Portuguese, Italian, Korean and Japanese. At Stanford that same year, she discussed the tension between ambition and execution, including the need for people inside established organizations to think entrepreneurially. Her experience had made her skeptical of a narrow founder costume or a single prescribed route. A person could bring initiative to an existing workplace. The interesting question was what they were prepared to try, learn and change.
She also had to learn to change her own management. Rottenberg has spoken candidly about being a perfectionist and a poor delegator in Endeavor’s early years. Becoming a mother to identical twin daughters helped her relinquish control and say no. She and her husband, author Bruce Feiler, live in Brooklyn. Her advice to “go big and go home” puts a welcome boundary around the appetite for growth. A growing organization requires other people to own decisions. So does a household, where the chief executive title carries considerably less authority.
“Go big and go home.”
Linda Rottenberg
Elsewhere has an AI opinion
The word Rottenberg now uses for overlooked entrepreneurial markets is Elsewhere. In a speech published in March 2026, she argued that discussions of artificial intelligence give too little attention to founders building applications around local needs. At the 2025 Athens Innovation Summit, she interviewed Google DeepMind co-founder Demis Hassabis and Greek prime minister Kyriakos Mitsotakis. The setting brought the geographical question into view: where should consequential technology be built, and who gets a say in its direction?
Her July 2026 interview about Japan returned to the everyday difficulties of growing a company. AI might make an early product easier to build, she argued, but founders still face hiring mistakes, disagreements and investor conflicts. Experienced peers can offer judgment formed by having endured comparable situations. The attraction of an entrepreneur network survives the availability of instant answers. A useful adviser may be the person who tells you something inconvenient and stays in the conversation afterward.
In July, she also made her first visit to Bucharest for Endeavor Romania’s fifth anniversary. The chapter’s account described a gathering of founders and business leaders concerned with ambition, international visibility and giving success back to the next generation. It was a recognizably Rottenberg subject, nearly thirty years after the taxi ride. She was still asking people to enlarge their sense of what could be built where they lived. Endeavor’s stated Vision 2035 aims for a footprint of 100 markets. The napkin plan has acquired a long itinerary.
The charm of her story is that the original problem remains legible. Someone has talent. Someone else has experience, capital or a useful introduction. Between them is a distance that neither a motivational slogan nor a postal address can fully explain. Rottenberg has spent her career organizing people across that distance. The taxi driver’s question became a question for investors, institutions and founders themselves: what would make starting possible here? Her answer keeps arriving in the form of another person willing to help.
