The new millennium was a time of potential and panic. People worried Y2K would cause computers to crash and planes to plummet. Instead, the world just partied. At the Lincoln Memorial, President Bill Clinton got down to Tom Jones singing his ‘60s hit, “It’s Not Unusual.”

Smartphones weren’t a thing, the stock market was booming off dot-com innovation, Rosanne Barr was a blue-collar icon and superhero movies were about to launch into the stratosphere. But soon America would elect a new leader and their sense of security would collapse. 

Jews were integrated into American society in ways never imagined, to the point that the 2000 Democratic vice president nominee was an Orthodox Jew. Interfaith marriage rates were skyrocketing, and assimilation was at the forefront of everyone’s minds.

From this, the Joshua Venture was born.

Founded in 2000 and based in San Francisco, the Joshua Venture: A Fellowship for Jewish Social Entrepreneurs invested in young Jewish leaders, mainly those that were culturally focused and unorthodox — the type of people who would have ordinarily struggled to obtain funding from traditional foundations. Though its first iteration lasted less than five years, the programs that it helped launch — among them JDub Records, Heeb Magazine and Storahtelling — have shaped a generation of Jews and continues influencing the Jewish world 25 years later.

Funded by the Nathan Cummings Foundation, the Walter & Elise Haas Fund and Steven Spielberg’s Righteous Persons Foundation, the original Joshua Venture supported two cohorts and 16 projects. Fellows received mentorship and training as well as $60,000 — the equivalent of more than $110,000 in today’s dollars, according to the Bureau of Labor Statistics. At retreats, fellows learned everything from how to shape an elevator pitch to the art of shmoozing at cocktail parties.

While AIPAC, American Jewish Committee and the Jewish federation system held sway in the early 2000s Jewish world, they weren’t “the thing of the moment,” Aaron Bisman, a member of the second Joshua Venture cohort and the co-founder of JDub Records, told eJewishPhilanthropy.

There was an “innovation craze,” he said, where investors were looking for “new scalable ideas, new funding models, new ways of thinking.” The economy was thriving, and “it was a time when experimentation may be seen as feasible.”

Fellows were often in their early 20s and for some, like Bisman, these initiatives were their first jobs.

The Jewish community was “running a generational relay,” Rachel Levin, the former executive director of Righteous Persons, told eJP. To survive, the Jewish community had to be imaginative.

“If you wanted to look for innovation, you look at the margins, to young people who don’t always feel themselves as part of the community,” she said, referencing a speech given by historian Jonathan Sarna titled “The Great Awakening.”

The founders of Joshua Venture asked themselves, “What would philanthropy look like if it were a creative act,” Levin recalled. “If there’s any creative act, it’s Judaism and Jewishness, it’s thousands of years of invention and reinvention and creativity and storytelling.”

Because the Joshua Venture was influenced by tech startup culture, it didn’t micromanage fellows and took risks on projects whose impact couldn’t be measured in traditional ways. While the money was great, the emotional support from major players was a game changer, Jennifer Bleyer, who was part of the first cohort and created Heeb Magazine, told eJP. “You weren’t just out there on your own trying to do some weird thing,” she said.

Like many young Jews, Bleyer didn’t fit into stereotypical Jewish boxes, so her lifestyle magazine was for others who didn’t: young, sardonic readers who were Jewish and also deeply interested in popular culture — be it hip-hop, comics, cinema, comedy or punk rock. Heeb — dubbed “The New Jew Review” — featured interviews with the leading Jewish actors, musicians and comedians of the day, replete with references to their Hebrew school experiences.

“One of the things Heeb tapped into for a lot of people was being able to be Jewish and these other things, and there was not a sense of conflict,” she said.

The first cohorts “were all kind of showy,” Bisman said, “and we’re willing to be bombastic.” 

The investment paid off, with fellows breaking into mainstream media. Heeb scored racks at Barnes & Noble and Borders bookstores and wooed celebrities for profiles including Sarah Silverman, Courtney Love and Drake. Bleyer was a guest on Howard Stern and the magazine was referenced on Comedy Central’s “Daily Show.” When Abraham Foxman, then-national director of the Anti-Defamation League and a regular foil of the publication, called a 2004 article “blasphemous to both Christians and Jews,” it only attracted more readers. The pinnacle came five years later when the magazine featured a full-page photograph in its “Germany Issue” of Rosanne Barr, dressed as a housewife version of Adolf Hitler, pulling a tray of burnt gingerbread men from an oven. The condemnations were resounding — in mainstream media and the Jewish press — only adding to the magazine’s well-founded anti-establishment reputation.

Meanwhile, Rabbi Amichai Lau-Lavie, a member of the first cohort and the founder of Storahtelling, which interpreted Torah through theater, made the cover of Time Out NY. JDub reggae-artist Matisyahu became an MTV sensation, dressed in full Hasidic garb, singing about wanting “Moshiach now.” 

JDub and Heeb brought Jewish content into secular spaces, Aliza Mazor, who held numerous positions at Joshua Venture including consultant, program director and interim executive director, told eJP. Their product was so good, she said, that when you attended a JDub show, your non-Jewish roommate insisted on tagging along.

But by 2005, the world looked much different than when the Venture began. The dot-com bubble burst and the stock market plummeted. Investors weren’t interested in risks. They wanted solid data showing a program’s impact, something difficult to do with art initiatives. During the Second Intifada, Jewish philanthropy pivoted back to Israel advocacy and combating antisemitism. At the same time, Levin and other leaders who started the Joshua Venture left their positions, and the organization fell into deficit just when the original funders had hoped it would become self-reliant.

In 2005, the organization shuttered, but four years later, the Joshua Venture relaunched with new funders: The Nathan Cummings Foundation, Lippman Kanfer Foundation For Living Torah, The Schusterman Family Philanthropies and The Stanford and Joan Alexander Foundation. Lessons were learned from the first go-round. This time, there would be greater oversight of programs with stricter impact measures aimed at issues funders cared about, such as inclusivity.

“The first version was very unique, and it was a point in time when [funders said], ‘Hey, let’s really ask young people what they want to be doing,’” Lisa Lepson, the executive director at the most recent iteration, told eJP. “When I went to restart the organization [funders said], ‘You know what’s hot now — impact. We need to have a strategy.”

Similar to the original program, the newer version, which ran from 2009 to 2016, provided three cohorts of two-year fellows with guidance, training and enough funding to quit their day jobs. A panel of fellows from the original program, including Bisman, mentored new fellows, speaking at retreats and providing inspiration.

In 2011, halfway through the first cohort, JDub announced it was closing. Over nine years, the label released 35 albums, three which went gold. Half of its budget came from sales, concert tickets and consulting fees, while the rest came from philanthropy.

Much of the problem was the lack of funding in the philanthropic world for second-stage startups, those that are up and running but still need support, said Bisman. “There’s a question of, ‘Why fund so many new things if you’re not going to fund their continuation?” 

Even before becoming a Joshua Venture fellow, Sarah Lefton, a member of the 2010 cohort who founded the Jewish digital storytelling company BimBam, was impacted by Bisman, who had invited her to sell shirts she made at JDub concerts.

Bisman’s honesty about his struggles helped Lefton, she said. “He got burned, and he was willing to talk about it, and he was willing to be angry and real, but also constructive and move on with his life.” Today, Bisman is senior vice president of marketing at Sesame Workshop.

The second iteration had its own struggles, too, some caused by the first iteration. After two years, the Texas-based Stanford and Joan Alexander Foundation pulled its funds when they found out about the Rosanne Barr photograph. Even though the issue had been published years earlier, at a time when Heeb wasn’t affiliated with the initiative, the Joshua Venture was left scrambling to fill the gap.

Another complication was that similar programs had been created to support Jewish startups, often funded by the same foundations, so in 2016, Joshua Venture merged with two such initiatives, UpStart and Bikkurim, with the merged program all falling under the UpStart name.

Over its 13-year run, spread over both iterations, Joshua Venture supported 38 fellows, with many programs still running, such as Matan, Keshet, Sharsheret, Wilderness Torah and Storahtelling — now known as Lab/Shul. Fellows whose programs shuttered became Jewish leaders, including sociologist Tobin Belzer and Jews of color advocate Yavilah McCoy.

Today, Matisyahu remains a face in mainstream culture, and many of JDub’s artists continue creating new music with a Jewish soul. Former Heeb writers and editors, many of whom got their break in journalism writing unpaid for the magazine, ascended the ranks in the Jewish and secular journalism scene, including eJP’s own managing editor, Judah Ari Gross. Relationships sparked at Heeb parties, with Heeb comics’ editor JahFurry singing reggae tunes, led to marriages between prominent Jewish leaders, then came baby in a baby carriage — and Jewish day school.

While many of the programs didn’t make it financially, “Everybody’s still doing the work in different ways,” Lefton said. BimBam closed in 2019 after 11 years of operation, pledging its assets to the Reform movement. Without major publicity, its YouTube channel has 121,000 subscribers and several videos have over a half-million views.

On the hierarchy of needs, once people have food and water, they need art to thrive, Lefton said, adding that people learn best through creativity. 

There are still programs working with artistic entrepreneurs, often influenced by Joshua Venture but with less funding. UpStart is still thriving, with Mazor cheering fellows on. Lefton currently runs Maimonides Fund’s Digital Storytellers Lab, a fellowship for 15 media creators. Another program founded in the early aughts, Reboot, has supported many influential films, podcasts and plays, including Alex Edelman’s Emmy and Tony award-winning “Just For Us,” which was on Broadway and streams on HBO and Max, and the Oscar-shortlisted film “The Anne Frank Gift Shop.”

There is a new generation of proud Jewish creatives breaking into mainstream culture, such as Lehrhaus, a Boston tavern and Jewish house of learning that was named one of Esquire Magazine’s best new restaurants in the U.S. in 2023 and one of Eater Magazine’s 38 Essential Boston Restaurants.

Similar to Heeb and JDub, Lehrhaus’ dreamers “mined Jewish ideas and identity and content and perspective to come up with original products that are grounded in authenticity, and that resonate broadly because of that authenticity,” Rabbi Charlie Schwartz, director of Lehrhaus, told eJP. “Exceptional culture will rise to the top.”

The impact of the Joshua Venture  shouldn’t be about counting numbers but about the passion it invigorated, Lau-Lavie, whose journey to running Lab/Shul is documented in the 2024 film “Sabbath Queen,” told eJP. “The old Jewish world is like, ‘How many members do I have?’ That is not how you gauge success. [You gauge success by] how many people are excited to show up? [By if] the Jewish world is a little more tolerant, less exclusive, more creative. Are we seeing that there are more opportunities and there’s a deeper sense of commitment to a Jewish life that isn’t the old binary.”

The fellows the Joshua Venture funded were young and experimental, and the fellowship was too. “There was definitely a sense that we were growing up together,” Bleyer, who left Heeb in 2003 after the financial side of publishing overwhelmed her, said. Today, she is a licensed master social worker who has written for New York Times and edited for Psychology Today.

Heeb went digital in 2010 and quietly stopped publishing in 2019, but it relaunched this week, at least partially. The new website now sells back issues of the publication and vintage Heeb T-shirts and stickers, but over the coming year, it plans to develop web shows, podcasts, social media content and live events, according to the new president of Heeb Media, Mik Moore. Bleyer is on the advisory board for the new iteration.

In time, Moore hopes to produce a yearly print magazine, which he believes people will love, pointing to the resurgence of LPs and Creem Magazine as examples of similar products making a comeback.

“In some ways, there’s a real parallel to when Jenn started Heeb the first time,” Moore said. “It was right after 9/11 and the beginning of the Bush administration, and this moment, coming out of Oct. 7 and the second Trump administration, There’s an open question about what Jewish culture is going to look like.”

He’s excited to give creatives the space to work their magic without “looking over their shoulder,” he said. “You work with great artists, you get great art, and if you can get great art, you will attract a community of people that appreciate great art.”