编者注：硅谷社区基金会的先驱领袖彼得•希罗于2016年8月21日因癌症辞世，享年73岁。在科技世界中，希罗是一位变革型人物。eBay创始人杰夫•斯科尔称赞希罗是他“最早的慈善导师”。“超过30年来，他一直是硅谷社会变革世界的领导者。”我们今天再次发布这篇最初刊发于2000年的经典特写，意在回顾彼得•希罗是“如何在硅谷开创了一种最终演变为生活方式的慈善文化。”

不久前，57岁的硅谷社区基金会总裁彼得•德库西•希罗，与一位年轻的网络巨头坐在一起聊天。这位硅谷精英刚刚赚得高达数百万美元的财富，他决定拿出一部分投入慈善事业。“你对哪个领域感兴趣？”希罗很好奇。“孩子、教育，还是老人？”这位捐助者茫然地注视着希罗。“您觉得呢？”他问道。

这是美国新经济中一个引人注目的事实：如此多擅长创造惊人财富的科技精英，对于捐赠的艺术毫无头绪。在旧经济中，与财富相伴相随的是一种义不容辞的高贵责任感(noblesse oblige)。硅谷不是这样。尽管硅谷现在坐拥7.5万名百万富翁，但长期以来，这片土地一直以“网络-吝啬”(cyber-stingy)著称。事实上，1998年发布的一篇研究报告显示，四分之一年收入超过10万美元的硅谷家庭每年仅向慈善事业捐赠500美元，甚或更少。

硅谷如此吝啬的原因不难理解。许多科技大亨与这座新兴之城并没有多少渊源，而且太过年轻，从未认真思考过如何留下一笔长久的公民遗产——更没有想过在自己一命呜呼之后提供一笔。另一个原因是他们的世界观：科技企业家往往目光狭隘，信奉自食其力的理念；在他们看来，与不幸的人分享财富意味着，给员工发放更多的股票期权。

然而，日益众多的硅谷显贵已经开始分享各自的万贯家财，而率先为硅谷展示捐赠之道的，正是彼得•希罗。通过为该地区独特的文化引入一种不同寻常的慈善品牌：苛求、雄心勃勃、充满自我意识、创造性，甚至带有风险性——简言之，它具备一切硅谷最为人熟知的特质——他做到了这一点。而且，希罗的慈善事业正在收获巨大的回报。11年前，当希罗来到硅谷时，社区基金会仅有900万美元的资产。现如今，这个数字大约为6.25亿美元。该基金会每周平均向各类社区团体、教育项目、社会服务机构和文化组织提供高达100万美元的赠款。在硅谷，慈善正在成为另一个增长产业。

然而，为了让这个产业起飞，希罗不得不找出一种新的方式来宣扬慈善事业。他指出，那种常见的假设，即“捐赠是一种道德义务——你富得流油，他们穷得叮当响，”在这里根本行不通。

关键先生

日前，在位于圣地牙哥市中心的社区基金会总部，彼得•希罗接受了《财富》记者的专访。冷石灰搭配木炭色的色彩布局，让这里颇具一家不差钱的互联网初创企业的风采。该基金会为这个预算年度设定了一个创纪录的筹资目标：1.5亿美元。仅过了5个月，它已经筹集到1亿美元。

如果说希罗已经对硅谷产生了一种变革性影响，那是因为他一直在使用科技巨头们能理解的条款经营慈善事业。他或许具有一位前大学校长的威严（他的确是），但他也拥有斯坦福大学MBA学位，更不必提及他在企业广告和营销领域的职业生涯。在香料岛公司干了4年之后，希罗离开了商业世界。他当时说，“我终于下了这个决定，我真的不在乎自己卖了多少罐胡椒粉。”1989年，在完成缅因艺术学院校长任期之后，希罗接掌了当时的圣克拉拉县社区基金会。

希罗现在是硅谷慈善捐赠领域的“关键先生”——甚至在他的基金会并不直接受益的时候，亦是如此。1991年，通过策划一场合作筹资活动，最终为11家经常相互争夺稀缺资金的硅谷艺术团体筹得1200万美元，他赢得了这一地位。去年，另一家硅谷慈善机构United Way宣布，多达1100万美元的资金缺口使得该组织无法继续资助108个当地服务机构。最终主持紧急救援行动的，当然是彼得•希罗。“很少有人能够搞定这种事。”社区基金会董事利奥•查韦斯说。“在硅谷，信誉是很难获得的。”

现在似乎很难理解的是，当希罗抵达硅谷时，他的基金会正陷于绝望。传统上，社区基金会严重依赖不参与具体事务的老年捐赠者。希罗说，“捐助者的角色是把钱捐给社区基金会——然后宁可老去。捐赠者只是在活着的时候承担临时责任。基金会从来没有想过为捐赠者提供终生服务。”在硅谷，这种方式根本行不通。“我的问题是，我们连一位过世的捐赠者都没有。”

在爆炸式增长的硅谷财富的帮助下，希罗重塑了硅谷的慈善事业。他将基金会转变为面向新捐助者的一站式服务中心——这恰恰是吸引该地区年轻的科技巨头所需要的。在某种程度上，社区基金会的存在正是为了让慈善事业更容易参与。捐赠者可以在那里设计一个基金，获得税收减免，避免运营自身基金会所涉及的种种行政麻烦。

希罗不遗余力地推动这个流程变得更加容易。他为每位捐赠者安排了一位员工，类似于一位私人银行家。该基金会悉心研究各类非营利性组织——就像券商分析师研究上市公司一样。它定期发布关于当地慈善事业、慈善机构的有效性和企业捐赠的研究报告，由此提供企业家渴望的那种基准。希罗还帮助新手制定慈善“战略”，并敦促他们建立一个多样化的捐赠“投资组合”：把一些资金投到成熟的非营利性组织，比如红十字会或当地食物银行（“个股”）；为基金会指定的“兴趣领域”（“共同基金”）拨一些资金；给一些或将产生优良业绩的前沿项目（“高价证券”）分配一块慈善基金。此外，希罗还经常向讲求实际的CEO们传播投身慈善事业的种种好处，比如享受税收优惠，还有利于招聘和留住员工，等等。

1997年，希罗抛弃了过于狭隘的“圣克拉拉县”一词，将旗下基金会的名称改为更具创业气息的“硅谷社区基金会”。现在，在一些备受瞩目的传道者的帮助下，硅谷的慈善事业已经翻开崭新的一页。eBay 联合创始人杰夫•斯科尔感慨道，“这里拥有如此多财富，但并没有足够多的良心。”这位35岁的亿万富翁已经在社区基金会建立了一只价值7000万美元的基金。“事实是，这个世界现在需要我们的帮助。”斯科尔说，一想到在自己的有生之年，能够对这个世界产生积极的影响，他就激动不已。“这真的是一件很酷的事情。”

当然，筹集大量善款和解决重大的社会问题，完全是两回事。有必要指出的是，尽管硅谷富可敌国，但这一地区仍然有许许多多的社会问题。希罗最大的挑战是，如何在新捐助者和真正需要完成的慈善事业之间，建立起一种富有成效的联系。

硅谷的命运

“硅谷的命运在何方？”从我们面前的大屏幕传来的画外音吟诵道。“我们是否将加入巴黎和君士坦丁堡这类永载史册，正在创造真正的人类事业的城市群？”抑或，这个声音问道，硅谷是否将成为“另一个终将萧条的繁荣都市？”

我坐在麦肯锡公司帕洛阿尔托办公室一个大型的U形会议桌旁边。围坐在周围的，还有公民团体“硅谷文化倡议”的二十多位成员。该组织即将为我们介绍一项新计划，其目的是说服硅谷领袖相信，文化很重要。这个计划就在我们面前摆放的黑色笔记本电脑上。呃，它是一款CD-ROM游戏。

这款名为《is.C3: 借助商业、文化和社区创造一个伟大的地区》的游戏，是一个模拟展示。其内容是，一位时年44岁的硅谷大亨遭遇车祸，不幸身亡，留下一笔高达5亿美元，旨在支持艺术事业的捐款。如何花费这笔钱，将决定硅谷是否可以达到“文艺复兴时期佛罗伦萨的文化高度。”

该组织执行董事约翰•克莱德勒介绍说，作为长达7个月劳动的结晶，这款游戏旨在劝说大约1000名硅谷领导人“接受文化很重要这一理念”。在一些地方，这种劝说或许是不必要的。但硅谷很需要，克莱德勒声称。“我们本可以创造一个PPT展示。但互动媒体是硅谷的方言。我们试图接触的很多人都玩游戏——电脑游戏。这是硅谷文化的重要组成部分。”

对于这个话题，你只需问问萨利•奥斯伯格。作为圣何塞儿童发现博物馆的执行董事，她运营着一家价值450万美元，拥有70名员工和950万美元捐款的企业。然而，当一些崭露头角的科技慈善家前来参观访问时，他们经常问奥斯伯格，她是不是一名志愿者。“他们无法相信，这是一家真正的企业。”她笑着说。“他们的带宽正在扩大，还有很长的路要走。”

早前，高科技精英的慈善事业所反映的，只是捐赠者本人的狭隘利益，而不是社区的实际需要。即使现在，科技企业大约一半的捐赠往往是电脑和软件。尽管非营利性组织乐于接受电脑，但很多组织没有钱聘请炙手可热的IT人才。希罗说，“对于社区的真正需要，硅谷企业还理解得不够透彻。”就连比尔•盖茨也对科技慈善家痴迷于全球的“数字鸿沟”表示不屑。最近，在西雅图举行的一个会议上，这位微软公司创始人尖锐地指出，对于许多还没有解决温饱问题的人来说，高科技设备并非头等大事。

社区建设

希罗尤为重视的一个议题是，如何防止高企不下的生活成本逼迫众多中产阶级纷纷逃离，进而使得硅谷最终成为一个只有超级富豪才住得起的门禁社区。“我们有可能沦为一个只剩下富人及其仆人的排他性社区。”希罗说。

在位于东圣荷西的梅费尔区，希罗独特的社区建设品牌遭遇到最为严峻的考验。正是在这个拥有6500人，主要由拉丁裔构成的低收入社区，硅谷社区基金会开始实施其最复杂和雄心勃勃的项目。

这是希罗的“高价证券”之一——高风险，但有潜力获得巨大的回报。策划于1997年的“梅费尔改进计划”旨在永久性地提升整个街区的前景，包括其街道、住宅、学校和居民。该计划预计需要超过1500万美元的公共和私人资金（包括惠普基金会提供的500万美元），涉及76个独立改造项目，列举一个抽样：提高识字率、增加路灯、雇用交通协管员、改造一个被忽视的社区花园、建立家庭日托中心、进行健康检查、提供理财咨询、绘制壁画、提供高科技职业培训，以及培养居民的领导能力。所有这些都将被精心监测，基金会将基于数百个精心设定的定量基准，定期评估项目进展。

就本质而言，社区基金会正在扮演总承包商的角色：管理基金，为额外的“投资机会” 寻找捐助者，并监督这一切。希罗将梅费尔视为一个旗舰项目，“我们所做的一切事情的缩影。”具体的项目清单和目标，均是社区自身制定的，而不是基金会颁布的。所有这一切旨在建立“连接”——在拉丁裔和越南裔邻居之间；在居民和公共机构之间；在居民与企业职业培训计划之间。那个此前被忽视的社区花园已经成为“附近居民的客厅。”希罗说。

升级一个社区并非易事：经济前景的改善将鼓励许多居民迁出，除非梅费尔成为一个更具吸引力的社区。只是改善社区环境，但没有增加家庭收入，将招致“高档化”。“关键是可持续性。”基金会董事利奥•查韦斯说。“我们正在努力那些导致贫穷固化的问题。”退出战略是个大问题。“我们将密切观察当惠普基金会的资金耗尽，社区基金会的员工退出之后，这里将发生什么事情。”

风险慈善模式

在希罗办公室所处走廊的那一头，43岁的Infoseek公司创始人史蒂夫•基尔希创建了隶属于社区基金会的史蒂夫和米歇尔•基尔希基金会。基尔希是硅谷慈善事业最热诚的传福音者，也是希罗最热情的盟友之一。他已经留出7500万美元净资产，用于多种多样的慈善事业——比如United Way（他率先为这家慈善组织捐助100万美元，以解决其资金缺口）；跟踪有可能撞击地球的行星。在其新公司Propel位于圣何塞的办公室，基尔希激烈地抨击“一毛不拔”的亿万富翁，还抱怨说，他曾经恳请一位互联网公司CEO将一大块股票投入慈善基金，但遭到无视。这位CEO的净资产一度达到20亿美元。“对他来说，捐赠1%的净资产根本就不是事儿。”基尔希抱怨说。他迅速地说出一连串需要效仿他的科技亿万富翁的名字。“我几乎不是硅谷最富有的人。”他指出。“绝对不是。”

基尔希所扮演的是挑衅者的角色，他不停地戳指硅谷的良心。希罗则寻找新的方式扩大捐助者群体。例如，多年来，他一直在竭力招揽忙碌的新科技百万富翁主动敲响他的房门。现在，他开始主动出击。基金会安排一位“捐赠辅导员”进驻思科公司庞大的企业园区。这是一片无可争议的沃土：思科在硅谷拥有1.8万名员工，其飙升的股票甚至让一些秘书都成为百万富翁。希罗还试图挖掘硅谷印度裔社区的财富——约20万社区成员估计拥有总值达500多亿美元的净资产。希罗表示，许多移民希望支持家乡的事业，但缺乏这样做的途径。因此，虽然社区基金会很少捐款支持本地区之外的事业，更遑论海外，但希罗正在尝试着开发一只基金，以方便印度捐助者回馈祖国，并支持硅谷的慈善事业。

他的基金会还成立了一个备受关注，面向年轻捐助者的“风险慈善”团队：硅谷社会风险基金，简称SV2。SV2以西雅图和奥斯汀的同行为榜样，吸引了100名风险投资家和企业家作为其“合作伙伴”。每人每年至少捐赠2500美元。社区基金会把这笔钱汇聚在一起，并辅之以匹配资金，以提供赠款。在“风险慈善”模式下，捐助者对非营利性机构实施风险投资公司经常进行的那种审查，然后提供专业知识，以推动其“投资”最大化。它坚持建立“指标”来衡量回报，并寻找“可扩展性”和“退出策略”。

风险慈善模式已经吸引了大量的嗡嗡声，以及质疑声。总部位于旧金山，资产达2.4亿美元的沃尔特和伊利斯•哈斯基金会执行董事布鲁斯•西弗斯表示，多年来，思虑周到的捐赠者一直在严格地审查他们所资助的非营利性组织，并坚持要求良好的业绩。但他担心，尝试将风投原则应用于非营利性组织，很容易走入歧途。“在商业世界里，有一个简单的测试：你赚到钱了吗？社会世界并没有一个与之对等的东西。”西弗斯也怀疑互联网精英们究竟带来了多少有用的知识。“仅仅因为他们依靠开发软件程序赚了大钱，并不意味着他们懂得如何开发教育项目。他们是瓷器店里的蛮牛，很可能会把事情搞砸。”西弗斯说，他听闻有一家非营利性组织的主要商业捐助者这样询问该组织高管：“给我说说，在这个领域，我们如何碾压竞争对手？”

当然，所有这些危险仍然是理论上的——这是一个不要过于极端化地使用某种方式的问题。希罗本人也对风投慈善的某些信条抱有一丝疑虑——如何才能衡量一家博物馆的“产品”？但他很高兴地看到一批新人投身慈善事业。毕竟，SV2的意义不仅仅在于资助非营利性组织，另一个至少同等重要的作用是，它还能够培养一批新的捐助者。eBay的斯科尔将SV2称为“年轻慈善家的训练轮”。

这家只限于受邀请人群的组织，已经多次登上全国性媒体头条——事实上，甚至在它发放首笔赠款之前，它就获得媒体关注。（首笔赠款为22.5万美元，受益者是当地一家非营利性组织，其宗旨是帮助出身于低收入家庭，成绩不佳的小学生。）好几位基金经理试图加入SV2，以期结识这些年轻的百万富翁。但没有人想被搭讪。“我们为成员提供的是一个安全的地方。”该组织一位成员说。另一位成员表示，SV2需要精心招揽“理想的成员，即热门CEO和热门风投家。”

“就慈善捐赠而言，我们没有历史，也没有榜样。”SV2联合创始人，风投公司Mayfield Fund管理合伙人邝伋荣说。“我们希望SV2能够缩短这个学习过程。”

希罗表示，假以时日，SV2所采用的风险慈善模式可能会不断演变。“随着他们对慈善事业的了解不断加深，他们的慈善捐赠可能会变得更加传统。” 这只是利用硅谷令人惊叹的财富的另一种方式。真正迫切的问题是，如何创造一个艺术繁荣发展，中产阶级具备购房能力，穷人活得有尊严，而且能改善自身处境的社区。要想让所有这一切成为现实，希罗说，“我们需要创造一种文化，让慈善成为硅谷的生活方式。如果我们不这样做，人们会说，‘我不敢相信这些家伙竟然搞砸了。’” (财富者文网)

译者：Kevin

本文最早发表于2000年11月27日的《财富》杂志。

Editor’s Note: Peter Hero, the pioneering leader of the Silicon Valley Community Foundation, died Sunday from cancer. He was 73.

Hero was a transformative figure in the tech world, described by Fortune editor-at-large Peter Elkind in a 2000 profile as the man who taught Silicon Valley, “the land of the ‘cyber-stingy,’” to care about philanthropy. He did it, Elkind wrote, “by channeling the area’s distinctive culture into an unusual brand of charity: demanding, ambitious, self-conscious, creative, even risky—in short everything you’d expect from Silicon Valley.”

In an online posting, founding eBay president Jeff Skoll, whose own charitable foundation has become a powerful force for good, praised Hero as his “original philanthropic mentor” and “a leader in the Silicon Valley social change world for more than 30 years.” Between 1989 and 2006, under Hero’s leadership, the Community Foundation’s assets multiplied from $9 million to more than $1.2 billion.

We republish Elkind’s fascinating profile of Hero below, which chronicles how Hero worked “to create a culture where philanthropy becomes a way of life in Silicon Valley.”

Not long ago, Peter deCourcy Hero, the 57-year-old president of Community Foundation Silicon Valley, sat down with a young dot-com mogul who had resolved to direct some of his newly minted millions toward charitable causes. “What are you interested in?” Hero wondered. “Children? Education? The elderly?” The donor looked at Hero blankly. “Whaddya got?” he asked.

It is a remarkable fact about the new economy that so many of those so skilled at generating mind-boggling wealth are so utterly clueless about the art of giving it away. In the old economy, riches were accompanied by a powerful sense of noblesse oblige. Not so in Silicon Valley. Though now home to a reputed 75,000 millionaires, it has long been known as the land of the “cyber-stingy.” Indeed, a 1998 study showed that a quarter of the Silicon Valley households with incomes over $100,000 gave $500 or less a year to charity.

The reasons for this lack of generosity aren’t hard to figure out. Many tech tycoons have shallow roots in the boomtown community and are far too young to have thought much about leaving behind a lasting civic legacy—or to provide one by kicking the bucket. Then there is their world-view: Tech entrepreneurs tend to be narrowly focused apostles of self-reliance who think sharing the wealth with the less fortunate means issuing employees more stock options.

Yet more than a conspicuous few have begun to share their largesse—and it is Peter Hero, more than anyone else, who has shown Silicon Valley how to give. He has done it by channeling the area’s distinctive culture into an unusual brand of charity: demanding, ambitious, self-conscious, creative, even risky—in short, everything you’d expect from Silicon Valley. And it’s posting big returns. Eleven years ago, when Hero arrived in the area, the Community Foundation held just $9 million in assets. Today that figure is about $625 million. The foundation hands out an average of $1 million in grants a week—to neighborhood groups, education programs, social-service agencies, and cultural organizations. Philanthropy is becoming another Silicon Valley growth industry.

To get that industry off the ground, however, Hero had to figure out a new way to sell philanthropy. The assumption “that giving is a moral obligation—You’re rich, they’re poor; you have to give your money away—that doesn’t fly out here,” notes Hero.

We are talking in Hero’s office at the Community Foundation headquarters in downtown San Jose, where the cool lime-and-charcoal color scheme offers the flavor of a well-funded Internet startup. A scrawled phrase on the obligatory whiteboard—“$576,920/day”—breaks down the foundation’s record fundraising goal for the budget year: $150 million. Just five months along, it has already collected $100 million.

If Hero has had a transforming effect on Silicon Valley, it’s because he operates in terms that tech moguls understand. He may have the gravity of a former college president (which he is), but he also has a Stanford MBA under his belt, not to mention a career in corporate advertising and marketing. Hero left the business world after a four-year stint at Spice Islands, when, he says, “I just finally decided I didn’t care how many more jars of pepper I’d sold.” In 1989, after serving as president of the Maine College of Art, he took over what was then called the Community Foundation of Santa Clara County.

Hero is now Silicon Valley’s go-to guy in the realm of charitable giving—even when it doesn’t directly benefit his own foundation. He attained that status in 1991 by masterminding a collaborative $12 million capital campaign for 11 showcase Silicon Valley arts groups—including the ballet, symphony, art museums, and opera—that had historically battled one another for scarce funding. Last year, when the local United Way—ostensibly a competitor for charitable dollars—announced a shocking $11 million shortfall that left it unable to fund 108 local social-service agencies, it was, of course, Hero who presided over the bailout. “Very few people could have pulled it off,” says Leo Chavez, chancellor of the local community college district and a Community Foundation director. “In this valley, credibility is hard to come by.”

While it seems hard to fathom now, when Hero arrived in Silicon Valley his foundation was in desperate straits. Traditionally, community foundations—there are more than 500 of them in the U.S.—relied heavily on bequests and gifts from elderly, uninvolved donors. Says Hero: “The donors’ role was to give away their money to the community foundation—and then, preferably, to die. Donors were merely to be suffered as a temporary responsibility while they were living. The whole idea of serving donors in their lifetimes was not really on the radar screen.” In Silicon Valley, that approach simply wouldn’t work. “My problem was, we didn’t have any dead donors.”

With the obvious help of a staggering explosion in local wealth, Hero reinvented Silicon Valley philanthropy. He did it by turning his foundation into a one-stop service center for new donors—precisely what was needed to involve the area’s young tech tycoons. Community foundations exist partly to make philanthropy easy. Donors can set up a fund there, take their tax deduction, and avoid the administrative headaches of running their own foundation.

Hero goes to special lengths to make the process even easier. Each donor is assigned to a foundation staffer, something like a private banker. The foundation provides research on various nonprofits—much as brokerage analysts cover public companies. It regularly produces studies—on local philanthropy, on charities’ effectiveness, on corporate giving—offering the sort of benchmarks entrepreneurs crave. Hero also helps newbies develop a philanthropic “strategy.” He urges them to build a diverse giving “portfolio” by directing some of their money to well-established individual nonprofits, such as the Red Cross or the local food bank (the “individual stocks”); by socking some away in foundation-directed “field of interest” pools (the “mutual funds”); and by allocating a piece to “highfliers,” cutting-edge programs that might generate spectacular results. Offering the hardheaded appeal that sells in his market, Hero talks to CEOs about philanthropy’s tax advantages—and even how it can help employee recruitment and retention.

In 1997, Hero discarded the parochial Santa Clara County moniker in favor of the more clearly entrepreneurial Community Foundation Silicon Valley. Now, with the help of some high-profile evangelists, philanthropy has turned a corner. “There was all this wealth and not a lot of conscience,” says eBay ebay co-founder Jeff Skoll, a 35-year-old billionaire who has established a $70 million fund at the Community Foundation. “The fact is, the world needs our help now.” Skoll says he is thrilled at the idea that he can make a difference during his lifetime. “This,” he declares, “is a really cool thing.”

Raising lots of money, of course, is one thing. Tackling big social problems—and for all its riches, Silicon Valley has plenty of them—is quite another. And that’s Hero’s biggest challenge: making productive connections between the strong-willed new donors he is managing to attract and what really needs to be done.

What will be the fate of Silicon Valley?” intones a voice-over from the big screen in front of us. “Will we join the pantheon of cities that history has judged as creating true belles époques of human enterprise”—cities like Paris and Constantinople—or, the voice asks, will Silicon Valley become “just another boomtown that went bust?”

I am seated at a large U-shaped conference table at the McKinsey & Co. offices in Palo Alto, along with two dozen members of a civic group called Cultural Initiatives Silicon Valley. Sleek black laptops, loaded and fired up, sit in front of us. We are here to be introduced to the group’s new plan for convincing area leaders that culture is important. It is..a CD-ROM game.

The game—catchily titled “is.C3: Creating a Great Region Through Commerce, Culture & Community”—is a simulation. It goes like this: Bruce Largecap, a major Silicon Valley tycoon, has been run over by a Mercedes SUV at the tender age of 44, leaving behind a $500 million endowment to support the arts. How you spend it will determine whether Silicon Valley can attain “the sustained cultural heights of Renaissance Florence.”

The product of seven months’ labor—and $250,000 worth of foundation grants and donated services from the likes of Apple aapl , Adobe, and the games division of Lucas Arts—the game is aimed, says John Kreidler, the group’s executive director, at getting some 1,000 area leaders “engaged in the idea that culture is important.” In some places this sort of persuasion might seem unnecessary—perhaps even self-indulgent. But Kreidler says it’s needed here. “We could have created a PowerPoint show. But interactive media is the vernacular of Silicon Valley. A lot of the people we’re trying to reach play games—computer games. It’s part of their culture.” Kreidler goes on to make the sort of good-for-bidness culture pitch that was familiar to residents of Texas in the oil-boom days—evidence that arts are a hard sell here.

Just ask Sally Osberg. As executive director of the Children’s Discovery Museum in San Jose, housed in a bright, engaging building on the edge of downtown, she runs a $4.5 million enterprise, with 70 employees and a $9.5 million endowment. Yet when budding tech philanthropists arrive to visit with her, they often ask whether she is a volunteer. “They can’t believe this is a bona fide business,” she chuckles. “Their bandwidth is widening—but they have a ways to go.”

Early on, high-tech philanthropy reflected the narrow interests of the givers more than the needs of the community. Even now, tech companies provide half of their corporate giving in the form of computers and software. While nonprofits are glad to have computers, many—in the overheated job market for trained techs—can’t hire IT staff to keep them running. To deal with that problem, the foundation is trying to set up a network of IT “circuit riders” who would service the equipment at various area nonprofits. “There’s not a lot of understanding,” says Hero, “of where the needs are.” Even Bill Gates—who donated hundreds of millions to wire libraries and schools—has become scornful of tech philanthropy’s obsession with the global “digital divide.” At a recent conference in Seattle, he pointedly noted that technology isn’t high on the priority list for people who don’t have enough to eat.

High on the list for Hero is preventing high costs from pushing out so many middle-class people that Silicon Valley becomes, essentially, a gated community for the absurdly wealthy. Already government agencies are having to subsidize housing costs for police officers and public school teachers. Nonprofits face the same challenge. A recent Community Foundation grant will pay apartment deposits for dancers with a local ballet company. “We’re in danger,” Hero warns, “of becoming a community of rich people and their servants.”

Nowhere will Hero’s particular brand of community-building be put to the test more than in the Mayfair neighborhood of East San Jose. It is there, in a low-income, mostly Hispanic community of 6,500—the birthplace of farm worker organizer César Chávez—that the foundation is presiding over its most complex and ambitious project.

This is one of Hero’s highfliers—risky, but with the potential for big returns. Hatched in 1997, the “Mayfair Improvement Initiative” is aimed at permanently upgrading the prospects for an entire neighborhood—its streets, its homes, its schools, and its residents. Projected to involve more than $15 million in public and private funding (including $5 million from the Hewlett Foundation), it involves a breathtaking array of 76 separate improvement projects. To name a sampling: boosting literacy, adding streetlights, hiring crossing guards, renovating a neglected community garden, establishing home day-care centers, conducting health screenings, offering family financial counseling, painting murals, providing high-tech job training, building residents’ leadership skills. All of that will be meticulously monitored, with regular assessment of progress toward meeting hundreds of carefully established quantitative benchmarks.

The Community Foundation is serving, in essence, as general contractor—managing funds, finding donors for additional “investment opportunities” (the proposed Cesar Chavez Sports Complex goes for $1.5 million), and overseeing it all. Hero sees Mayfair as a flagship project— “a microcosm of what we’re about.” The list of projects—and goals—was developed by the neighborhood, not handed down. Everything is aimed at building “connections”—between Hispanic and Vietnamese neighbors; with public agencies; with corporate job-training programs. The community garden, Hero says, has become “the neighborhood living room.” A weekly farmers’ market has drawn outsiders into the community. There’s even a program to teach fundraising skills—so Mayfair residents will learn how to get private-foundation millions on their own.

Upgrading a neighborhood is not easy: An improvement in residents’ economic prospects will encourage many to move out, unless Mayfair becomes a more attractive neighborhood. And simply making neighborhood improvements without increasing household income will invite gentrification. “The whole issue is sustainability,” says Leo Chavez, who has been heavily involved in the project. “We’re trying to fix the issues that sustain poverty.” The big question, he notes, is the exit strategy. “We’ll see what happens when the Hewlett money runs out and the Community Foundation staffers pull out.”

Down the hall from Hero’s office, Steve Kirsch, the 43-year-old founder and former chairman of Infoseek, has established the Steven and Michele Kirsch Foundation—affiliated with the Community Foundation. Kirsch is Silicon Valley philanthropy’s most fervent evangelist and one of Hero’s most passionate allies. He has set aside $75 million of his net worth for charity, which he has been parceling out to causes as diverse as the United Way (he wrote the first $1 million check for the bailout) to tracking asteroids threatening to strike planet Earth. In the San Jose offices of his new startup, Propel, Kirsch rants about tight-fisted billionaires, bemoaning the case of one dot-com CEO who ignored his pleas to put a chunk of stock into a charitable fund. For a time, he was worth $2 billion. “He could have given 1% and never even missed it!” Kirsch complains. He quickly rattles off the names of tech billionaires who need to follow his example. “I’m hardly the richest guy in Silicon Valley,” he notes. “Not by a long shot.”

While Kirsch plays the provocateur—the finger-pointing conscience on the shoulder of Silicon Valley—Hero looks for new ways to expand the donor ranks. After years of wrestling with how to bring busy new tech millionaires to his door, for example, he’s now hatching schemes to go to them. The foundation has placed a “giving counselor” on the sprawling corporate campus of Cisco Systems csco . It is indisputably fertile ground: Cisco has 18,000 employees in Silicon Valley, and its soaring stock has made even some secretaries millionaires. He’s also trying to tap the wealth of Silicon Valley’s 200,000-member Indian community, with an estimated combined net worth of more than $50 billion. Many immigrants want to support causes in their homeland, Hero says, but don’t have a vehicle for doing so. So while community foundations rarely initiate giving outside their own regions—and almost never operate overseas—Hero is exploring the idea of developing a fund through which Indian donors could support projects in blighted neighborhoods in both their homeland and Silicon Valley.

Finally, there is the foundation’s high-profile “venture philanthropy” group, aimed at young donors: the Silicon Valley Social Venture Fund, known as SV2. Modeled after counterparts in Seattle and Austin, SV2 has attracted 100 “partners” from the ranks of venture capitalists and entrepreneurs. Each contributes at least $2,500 a year. The money is pooled—and matched with Community Foundation funds—to provide grants. Under the “venture philanthropy” model, the donors subject nonprofits to the sort of scrutiny a venture capital firm would apply, then offer their expertise to maximize their “investment.” It insists on establishing “metrics” to measure returns and looks for “scalability” and “an exit strategy.”

The venture-philanthropy model—which has drawn plenty of buzz—has its skeptics. Bruce Sievers, executive director of the San Francisco-based Walter and Elise Haas Fund, a foundation with $240 million in assets, says thoughtful donors have been rigorously scrutinizing nonprofits they fund—and insisting on good results—for years. But he worries that it’s easy to go too far in trying to apply VC principles to nonprofits. “In the business world, there’s a simple test: Do you make money? There’s nothing equivalent in the social world.” Sievers also questions how much useful knowledge dot-commers bring to the table. “Because they’ve made a lot of money developing a software program doesn’t mean they know about developing education programs. They’re a potential bull in a china shop.” Sievers says he knows of one nonprofit executive who had a major business donor turn to her and ask, “Remind me: In this field, do we crush the competition?”

All those dangers, of course, remain theoretical—a question of not taking an approach too far. Hero, for his part, is a bit wary of some of venture philanthropy’s tenets—how can a museum’s “product” be measured?—but he’s delighted with the fresh recruits to charity’s cause. SV2, after all, is at least as much about training new givers as it is about funding nonprofits. eBay’s Skoll, who’s a member, calls it “kind of like training wheels for young philanthropists.”

Already the invitation-only organization has generated scads of national press—in fact, it was getting media attention even before issuing its first grant (which turned out to be $225,000 to a local group that helps underperforming low-income elementary school students). Several money managers have tried to join to get access to the young millionaires. But no one wants to be hit on. “One thing we are providing to our members is a safe place to be,” says a member of the group. SV2, urges another, needs to carefully target “the ideal people to become members of this group—the hot CEOs and the hot venture capitalists.”

“We had no history and no role models for doing philanthropic giving,” says SV2 co-founder Kevin Fong, managing partner of the Mayfield Fund, a Menlo Park VC firm. “We want SV2 to shortcut that learning process.”

Over time, says Hero, the venture philanthropy model embraced by SV2 may well evolve. “As they get to know these charities, their charitable giving may become more traditional.” It’s all just one more way to harness the astounding wealth of Silicon Valley. And that’s what is truly urgent, Hero says—creating a community where the arts can flourish, middle-class people can afford a home, and the poor can live in dignity and better themselves. For all of that, says Hero, “we need to create a culture where philanthropy becomes a way of life in Silicon Valley. If we don’t do that, people will say, ‘I can’t believe these guys blew it.'”