✍️ Outsider Ink: Linda Rottenberg Rewind, Crazy Is a Compliment, The Multiplier Effect
Outsider Ink is a bi-weekly newsletter from Outsider Inc.
In the latest episode of Outsider Inc., we welcomed Linda Rottenberg, the co-founder and CEO of Endeavor—the global organization supporting high-impact entrepreneurs in emerging markets through capital and community. Linda rejected the conventional path, instead following her curiosity to solve big problems. She defined a new way to uplift entrepreneurs from the forgotten corners of the world and started a movement around ecosystem building to make success repeatable and lasting. Her bold vision and leadership set an example for anyone who's breaking barriers around antiquated business cultures and what she's created with Endeavor will pay dividends for years to come. This is an amazing episode you won’t want to miss. Tune in now ⤵️.
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Crazy Is a Compliment
In 2014, Linda published her best-selling book Crazy Is a Compliment: The Power of Zigging When Everyone Else Zags, where she persuasively argues that being called crazy is often a sign you're on the right track. Drawing on her experience building Endeavor and supporting entrepreneurs worldwide, Linda argues that the willingness to take intelligent risks and challenge the status quo is essential not just for startup founders, but for anyone looking to lead change—in business, life, and community.
The book blends inspiring stories with practical advice, showing that successful entrepreneurs aren’t reckless—they are “practical dreamers” who start small, learn fast, and stay resilient. Linda emphasizes that entrepreneurship is not only reserved for the young or well-connected. Whether it’s a corporate intrapreneur, a mid-career professional seeking major change, or a founder in an emerging market, the traits that matter most are hustle, adaptability, and the courage to act despite uncertainty.
What I really appreciate about Crazy Is a Compliment is how different it feels from the typical business book. Linda’s voice is refreshingly grounded—full of energy but also embodied wisdom. She’s not selling a formula; she’s giving permission for leaders to think differently and act decisively, even when it feels messy to do so. Her celebration of practical dreaming resonates; it bridges the gap between audacity and execution that so many boilerplate leadership books miss.
The Multiplier Effect
During the episode, Linda referenced Endeavor’s research on the entrepreneurship ecosystem multiplier effect, which shows how a small group of fast-scaling founders can disproportionately drive ecosystem growth when they pay their success forward. In cities like Buenos Aires, Istanbul, New York, and more, Endeavor demonstrated how a group of successful founders accelerated and solidified ecosystem development by mentoring, investing, launching new ventures, and circulating talent.
A key insight is that scale unlocks impact: founders who build meaningful companies are far more likely to become “influencers” who can be highly effective in supporting the next generation of entrepreneurs. Endeavor’s network mapping reveals that the most vibrant ecosystems often trace back to just a few key leaders whose continued engagement powers dozens or even hundreds of startups.
Crucially, ecosystem growth is nonlinear. It’s not about launching more startups, but about scaling a few whose founders stay involved. Without those leaders, ecosystems plateau. These findings reinforce the importance of cultivating breakout companies and entrepreneurial recycling—ideas that align closely with my work with Brad Feld in The Startup Community Way, which I wrote about in an earlier post of Outsider Ink.
Endeavor launched an interactive companion website to illustrate the multiplier effect in several key regions around the world. It’s definitely worth checking out ⤵️.
Episode Highlights
One of my favorite moments from the episode was where Linda gives a masterclass on how the flywheel of entrepreneurial ecosystem development gets sparked:
Later, Linda encourages outsiders who broke through and achieved success to openly share their stories, since doing so is critical for inspiring the next generation of leaders trying to break in from the outside:
I had a great time chatting with Linda about her journey building Endeavor, her earned wisdom on building ecosystems, and the numerous success stories of outsiders she’s witnessed close-up and shared in the episode—including her own journey. Linda is an incredible innovator, leader, and change-maker. I’d love to have her back.
Up Next
Tune in next week when we’re joined by Jason Seats. He was co-founder of Slicehost, a virtual hosting platform he bootstrapped to millions in annual recurring revenue from a small office in St. Louis before selling to cloud-computing giant Rackspace in 2008. Slicehost earned the admiration of the Collison Brothers, inspiring their early vision for Stripe. Jason was Chief Investment Officer at Techstars, the world’s largest and most geographically-dispersed pre-seed investor, where he also launched accelerators in San Antonio and Austin. As a Techstars Managing Director, Jason invested in multiple companies that reached billion dollar outcomes, and as Chief Investment Officer, he oversaw the deployment of hundreds of millions of capital to thousands of companies.