Building bridges: Why Portugal is attracting and i...

Building bridges: Why Portugal is attracting and inspiring a new generation of US start-up founders

Jonathan Littman at RedBridge Lisbon

By: Chris Graeme

RedBridge co-founder and best-selling author Jonathan Littman explains just what makes Portugal so attractive to this segment

RedBridge is a new association for a cross-border community created by and for international entrepreneurs who are passionate change-makers looking for a more holistic approach to business between Lisbon and the San Francisco Bay.

Behind the elegant 19th-century façade of a Lisbon downtown mansion, something quite remarkable is happening. Here is a meeting, or rather meetings, of the minds of a burgeoning group of young entrepreneurs from Portugal and the San Francisco Bay Area, and other countries too.

All share certain things in common. First and foremost is a love of Portugal, the Portuguese culture, gastronomy and way of life, as well as the relaxed, easy-going manner of conducting business and an innovative genius which is down to a more organic, lateral and less linear way of thinking.

These entrepreneurs and investors also have a mindset in common which rejects a wholly exploitative approach to doing business, but rather seek a holistic, sustainable path which gives back to the environment and adds to the culture and the Portuguese people and their way of life.

The association is called RedBridge and was founded in 2022 by international best-selling author Jonathan Littman, Portuguese marketing guru Hugo Antonelo, US entrepreneur Nathan Hadlock, Lisbon-based lawyer Filipa Pinto de Carvalho, and serial entrepreneur Paulo Gaspar. Since the first event on April 30, 2022, RedBridge has hosted 10 events.

I attended one of these meetings in October, which took place in the informal setting of a rustic urban garden on the grounds of a 19thcentury palace located on the city’s Rua Vítor Cordon. Music was playing and people chatted animatedly with cans of beer and glasses of wine in hand against the stunning backdrop of a sleepy River Tagus and its iconic 25 de Abril bridge from which this association takes its name – RedBridge.

The symbolism is not lost on me. Interestingly, this bridge has a ‘relative’ in the US: It was built by the same company (American Bridge Company) that constructed the San Francisco Oakland Bay Bridge (but not the Golden Gate Bridge). And after just a few months RedBridge is already creating a bridge between Californian and Portuguese entrepreneurs with innovative like-minded ideas, and know-how spanning the United States and Portugal.

Busy moderating a top-calibre line-up of start-up founders and university academics, Jonathan Littman met me in Cascais. A San Francisco Bay native from Sausalito – quite a coincidence really since it is twinned with Cascais – his father was English, and during a break from his studies at the University of California at Berkley (he later earned a degree in Rhetoric), Littman travelled widely throughout Europe and even spent time as a caretaker of a castle in Italy.

Charming, gregarious and expansive, his character and mannerisms are typical of intellectuals whose minds are brimming with ideas and enthusiasm.

The founder of, The Innovation Hub, and the co-author of the international IDEO bestsellers The Art of Innovation and The Ten Faces of Innovation Littman has been leading immersive seminars and delivering keynotes on entrepreneurship, start-ups, and innovation in the US, Europe, and China for a decade.

An adjunct professor at the University of San Francisco, Littman tells me he also teaches Creativity, Innovation, and Applied Design, an interactive approach to tapping anthropology and cross-pollination techniques to uncover unique insights and prototype new products and services.

Littman’s nine books, four of which have been optioned for film, have covered such topics as computer hackers, technology, sports, and business. As a journalist, he has written for Forbes and the Los Angeles Magazine, and he was a contributing editor for Playboy.

Giving back to Portugal

RedBridge, Littman tells me, is a curated club of entrepreneurs where the unofficial membership requirement is to have the right mindset. Still in its infancy, the membership fee is reasonable, although the price will be higher for corporations.

“We aim to attract people who want to give back to Portugal. So many times, I have come across people who want to join a club just to net clients. Too often they are men. Here, we are looking for phenomenal entrepreneurs and professionals who want to help us build this RedBridge community network from the roots up,” says Littman, who points out that they have no desire for this public association to be a profit-making enterprise.

Littman says that whilst Portugal has a talented crop of high-tech engineers, they tend to lack international contacts and connections for know-how and investment, which is why California and the Bay Area have been so inspirational for the founders of Portugal’s start-ups.

“What California has done well is to embrace talented immigrants. We communicate and move projects along in California at a very accelerated pace, and most of the world does not have that same level of exponential efficiency and speed,” he explains, adding that it is not just about technology. The San Francisco path is more like a 100 metres dash. It is about “efficient thinking moulded by very good thinkers.”

Common ground

So, what is it about Portugal and Lisbon that entrepreneurs from California and elsewhere find so appealing?

First, they have found common ground. These young and dynamic business leaders have relocated or travel back and forth from the United States to Portugal because they have realised that the Portuguese, with their laid-back, out-of-the-box thinking, can teach them a thing or two about actually living; working to live, and not living to work.

Second, as their own country becomes ever-more politically and socially divided, these US entrepreneurs have come to value the certain quiet modesty that the Portuguese naturally have, their fine food and wines, and calm society, far removed from gun law issues, school shootouts, and the political divides laid bare by the turmoil that ensued with court cases over the storming of the Capitol building.

Jonathan Littman stresses that Americans, particularly Californians, love Portugal because of the ‘good life’ (a boa vida), living by the sea, the ease of making true friends, the entrepreneurial thirst that the Portuguese possess, and the feeling of being in the ‘California of Europe’. In fact, he was so enamoured of the attitude, lifestyle and creative thinking in Portugal that it inspired him to pen a feature article for the Los Angeles Magazine under the headline ‘The New California Dream is in Portugal’.

The author and innovation consultant points out that Lisbon, like San Francisco, has a vibrant expat community. In the Portuguese capital, you’ll encounter Brazilians, French, Ukrainians, British, Africans, Italians and Americans, increasingly Californians.

And it has not just been the retired relocators seeking a second home near a beach under the sun. Since 2017, a number of high-profile celebrities have either moved to Lisbon or spend a considerable amount of time in the city famed for its unique golden light.

The black and white cobbled pavements or calçadas, pastel-painted mansions, and houses with bright blue, yellow and red window lintels and doorways, quaint narrow winding alleys with their secluded cafés and restaurants from which the rich aroma of freshly ground coffee and grilled sardines with fresh bread wafts: this is Lisbon.

RedBridge co-founder Hugo Antonelo points to the innovative energy that young people have in Portugal, and says it was no accident that Lisbon was chosen by Paddy Cosgrove, the founder of Web Summit to host the annual technology conference held in the city since 2016.

Portugal now has seven unicorns and most of them are connected with California and Silicon Valley in one way or another, so changes had already been happening in Portugal’s development as a major start-up destination and innovation hub,” says the FunnyHow co-founder.

Antonelo highlights the similarities between Portugal and Lisbon with its Estoril Riviera, and California with San Francisco and the Bay Area; the surfing, the beach lifestyle, the iconic landmark red bridges, the yellow trams and even the hills – both San Francisco and Lisbon are built on seven hills. “There is more than work that connects people from California with Lisbon in particular and Portugal as a whole,” says Antonelo

“Companies are people, and we are thinking about people first. I opened my office in San Francisco in 2019. I met Jonathan and we agreed there was a stream of people coming to Portugal from California after the pandemic, and Portuguese moving to California.

In fact, Jonathan and I were two such examples,” he explains, adding that TAP’s direct flights to San Francisco were also a boon. When the pair realised the momentum, they thought creating a club for the community of entrepreneurs that had links to both countries was a great idea to “break the expat bubble”.

“We wanted to help this California community to break out and meet Portuguese entrepreneurs, talent and investors, and create a mix of those two worlds,” continues Hugo Antonelo.


The idea for a cross-border association was already sprung in San Francisco with the founding of a very exclusive club for innovative entrepreneurs called Shack15. Jonathan Littman explains how he discovered it and met Hugo Antonelo.

“When I first came to Lisbon, I realised this was the place to be but continued working in San Francisco while also visiting Lisbon and giving lectures. I had trips scheduled for April 2020 and then Covid-19 started,” he says, adding that he immediately began taking Portuguese lessons via Zoom with a teacher in Braga.

In the fall of 2021, Littman was finally able to return to Lisbon. “I met all of these interesting and creative people including Hugo Antonelo whose office is in the building where RedBridge is now.” Needing a place from which to work, Littman asked him if he could base himself in his office for three months, the maximum he could stay in Lisbon under the terms of his visa. At a party, Antonelo asked him: “Are you just here to have fun, or do you want to do something with your life?” It was the beginning of a partnership and the birth of an idea.

“I invited Hugo and one of his business partners, Paulo Gaspar, vice-president of the Grupo Media Capital and Chairman of FunnyHow, who has been very active in investing in California, to San Francisco. We went to Shack15, a club for entrepreneurs and investors – actually a misnomer since it is a spacious, elegant building in the maritime area of San Francisco Bay founded by a Norwegian investor in January 2020,” he recounts. “It was the best ‘thinkubator’ that I had ever seen, and I immediately invited Portuguese entrepreneurs and we had a brainstorming session in the autumn of 2021.”

Littman had secured a new client called BYFoods whose flagship product is a Portuguese custard tart or pastel de nata branded as ‘Nata Pura’. The company wanted to take it global. Their immediate goal was the United States, and so he hosted an event for them at Shack15 on April 27, 2022, with 300 custard tarts delivered. Later that fall, Littman led a much larger event featuring pastel de nata and Portuguese wines. ‘Why Californians Love Portugal’ was attended by around 150 people, including the Portuguese Consul General in San Francisco, Pedro Pinto, and serial entrepreneur Torben Rankine. Shack15, seen very much as RedBridge’s ‘sister club’ in San Francisco, also helped host a state dinner for Portugal’s President Marcelo Rebelo de Sousa when he visited the Portuguese and Portuguese-descendant business community there last September.

Design thinking

Partner and co-founder of RedBridge, Nathan Hadlock is a good illustration of a US entrepreneur who has traded his life in San Francisco for Lisbon. An advisor to the Golden Visa fund Pela Terra, Hadlock is examining creating sustainable farmland in Portugal.

He says: “We’re working towards solving agricultural problems here in Portugal, particularly issues with soil. Conventional agriculture that has lasted hundreds of years has completely exhausted this critical part of the system. In our project, we work with operators to change their practices and focus more on soil – meaning cover crops, animal grazing and organic amendments.”

Nathan has now been living in Portugal for two and a half years, his first time based out of the US. “I am seeing this country through the eyes of an immigrant. I always wondered why all the most successful companies in the US were founded by immigrants, and how they could see opportunities and problems that I didn’t. Now I am experiencing this for the first time.”

It’s really exciting here in Portugal; everywhere I look I see business opportunities and for Americans, specifically those from San Francisco, where a lot of the technology and business and funding models are cutting-edge, it’s good to share that knowledge here in Portugal.”

However, Hadlock says that whereas Americans often miss the point about the meaning of sustainable business and see things in a very extractive way, the Portuguese really value people and putting back.

“We should be creating companies and products that make life better, rather than products that just monopolise your time even more and get you to buy things that are not really needed and are soon discarded.”

It is a view shared by Jonathan Littman who is a proponent and expert in ‘Design Thinking’ which takes a more holistic and innovative approach to maximising products and experiences. This holistic approach is one that California which, he says, has been struggling to recover from an existential crisis as a state that many of its own residents believe is in decline, could learn from.

Portugal offers a second chance to live the California good life enjoyed in the past. I expect we’ll see lots more entrepreneurs seeking culture waves and tech opportunities turn up in Lisbon and Portugal’s other major cities.”

Follow RedBridge on Linkedin or visit the website.


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