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編者注：硅谷社區基金會的先驅領袖彼得?希羅于2016年8月21日因癌癥辭世，享年73歲。在科技世界中，希羅是一位變革型人物。eBay創始人杰夫?斯科爾稱贊希羅是他“最早的慈善導師”。“超過30年來，他一直是硅谷社會變革世界的領導者。”我們今天再次發布這篇最初刊發于2000年的經典特寫，意在回顧彼得?希羅是“如何在硅谷開創了一種最終演變為生活方式的慈善文化。”

不久前，57歲的硅谷社區基金會總裁彼得?德庫西?希羅，與一位年輕的網絡巨頭坐在一起聊天。這位硅谷精英剛剛賺得高達數百萬美元的財富，他決定拿出一部分投入慈善事業。“你對哪個領域感興趣？”希羅很好奇。“孩子、教育，還是老人？”這位捐助者茫然地注視著希羅。“您覺得呢？”他問道。

這是美國新經濟中一個引人注目的事實：如此多擅長創造驚人財富的科技精英，對于捐贈的藝術毫無頭緒。在舊經濟中，與財富相伴相隨的是一種義不容辭的高貴責任感(noblesse oblige)。硅谷不是這樣。盡管硅谷現在坐擁7.5萬名百萬富翁，但長期以來，這片土地一直以“網絡-吝嗇”(cyber-stingy)著稱。事實上，1998年發布的一篇研究報告顯示，四分之一年收入超過10萬美元的硅谷家庭每年僅向慈善事業捐贈500美元，甚或更少。

硅谷如此吝嗇的原因不難理解。許多科技大亨與這座新興之城并沒有多少淵源，而且太過年輕，從未認真思考過如何留下一筆長久的公民遺產——更沒有想過在自己一命嗚呼之后提供一筆。另一個原因是他們的世界觀：科技企業家往往目光狹隘，信奉自食其力的理念；在他們看來，與不幸的人分享財富意味著，給員工發放更多的股票期權。

然而，日益眾多的硅谷顯貴已經開始分享各自的萬貫家財，而率先為硅谷展示捐贈之道的，正是彼得?希羅。通過為該地區獨特的文化引入一種不同尋常的慈善品牌：苛求、雄心勃勃、充滿自我意識、創造性，甚至帶有風險性——簡言之，它具備一切硅谷最為人熟知的特質——他做到了這一點。而且，希羅的慈善事業正在收獲巨大的回報。11年前，當希羅來到硅谷時，社區基金會僅有900萬美元的資產。現如今，這個數字大約為6.25億美元。該基金會每周平均向各類社區團體、教育項目、社會服務機構和文化組織提供高達100萬美元的贈款。在硅谷，慈善正在成為另一個增長產業。

然而，為了讓這個產業起飛，希羅不得不找出一種新的方式來宣揚慈善事業。他指出，那種常見的假設，即“捐贈是一種道德義務——你富得流油，他們窮得叮當響，”在這里根本行不通。

關鍵先生

日前，在位于圣地牙哥市中心的社區基金會總部，彼得?希羅接受了《財富》記者的專訪。冷石灰搭配木炭色的色彩布局，讓這里頗具一家不差錢的互聯網初創企業的風采。該基金會為這個預算年度設定了一個創紀錄的籌資目標：1.5億美元。僅過了5個月，它已經籌集到1億美元。

如果說希羅已經對硅谷產生了一種變革性影響，那是因為他一直在使用科技巨頭們能理解的條款經營慈善事業。他或許具有一位前大學校長的威嚴（他的確是），但他也擁有斯坦福大學MBA學位，更不必提及他在企業廣告和營銷領域的職業生涯。在香料島公司干了4年之后，希羅離開了商業世界。他當時說，“我終于下了這個決定，我真的不在乎自己賣了多少罐胡椒粉。”1989年，在完成緬因藝術學院校長任期之后，希羅接掌了當時的圣克拉拉縣社區基金會。

希羅現在是硅谷慈善捐贈領域的“關鍵先生”——甚至在他的基金會并不直接受益的時候，亦是如此。1991年，通過策劃一場合作籌資活動，最終為11家經常相互爭奪稀缺資金的硅谷藝術團體籌得1200萬美元，他贏得了這一地位。去年，另一家硅谷慈善機構United Way宣布，多達1100萬美元的資金缺口使得該組織無法繼續資助108個當地服務機構。最終主持緊急救援行動的，當然是彼得?希羅。“很少有人能夠搞定這種事。”社區基金會董事利奧?查韋斯說。“在硅谷，信譽是很難獲得的。”

現在似乎很難理解的是，當希羅抵達硅谷時，他的基金會正陷于絕望。傳統上，社區基金會嚴重依賴不參與具體事務的老年捐贈者。希羅說，“捐助者的角色是把錢捐給社區基金會——然后寧可老去。捐贈者只是在活著的時候承擔臨時責任。基金會從來沒有想過為捐贈者提供終生服務。”在硅谷，這種方式根本行不通。“我的問題是，我們連一位過世的捐贈者都沒有。”

在爆炸式增長的硅谷財富的幫助下，希羅重塑了硅谷的慈善事業。他將基金會轉變為面向新捐助者的一站式服務中心——這恰恰是吸引該地區年輕的科技巨頭所需要的。在某種程度上，社區基金會的存在正是為了讓慈善事業更容易參與。捐贈者可以在那里設計一個基金，獲得稅收減免，避免運營自身基金會所涉及的種種行政麻煩。

希羅不遺余力地推動這個流程變得更加容易。他為每位捐贈者安排了一位員工，類似于一位私人銀行家。該基金會悉心研究各類非營利性組織——就像券商分析師研究上市公司一樣。它定期發布關于當地慈善事業、慈善機構的有效性和企業捐贈的研究報告，由此提供企業家渴望的那種基準。希羅還幫助新手制定慈善“戰略”，并敦促他們建立一個多樣化的捐贈“投資組合”：把一些資金投到成熟的非營利性組織，比如紅十字會或當地食物銀行（“個股”）；為基金會指定的“興趣領域”（“共同基金”）撥一些資金；給一些或將產生優良業績的前沿項目（“高價證券”）分配一塊慈善基金。此外，希羅還經常向講求實際的CEO們傳播投身慈善事業的種種好處，比如享受稅收優惠，還有利于招聘和留住員工，等等。

1997年，希羅拋棄了過于狹隘的“圣克拉拉縣”一詞，將旗下基金會的名稱改為更具創業氣息的“硅谷社區基金會”。現在，在一些備受矚目的傳道者的幫助下，硅谷的慈善事業已經翻開嶄新的一頁。eBay 聯合創始人杰夫?斯科爾感慨道，“這里擁有如此多財富，但并沒有足夠多的良心。”這位35歲的億萬富翁已經在社區基金會建立了一只價值7000萬美元的基金。“事實是，這個世界現在需要我們的幫助。”斯科爾說，一想到在自己的有生之年，能夠對這個世界產生積極的影響，他就激動不已。“這真的是一件很酷的事情。”

當然，籌集大量善款和解決重大的社會問題，完全是兩回事。有必要指出的是，盡管硅谷富可敵國，但這一地區仍然有許許多多的社會問題。希羅最大的挑戰是，如何在新捐助者和真正需要完成的慈善事業之間，建立起一種富有成效的聯系。

硅谷的命運

“硅谷的命運在何方？”從我們面前的大屏幕傳來的畫外音吟誦道。“我們是否將加入巴黎和君士坦丁堡這類永載史冊，正在創造真正的人類事業的城市群？”抑或，這個聲音問道，硅谷是否將成為“另一個終將蕭條的繁榮都市？”

我坐在麥肯錫公司帕洛阿爾托辦公室一個大型的U形會議桌旁邊。圍坐在周圍的，還有公民團體“硅谷文化倡議”的二十多位成員。該組織即將為我們介紹一項新計劃，其目的是說服硅谷領袖相信，文化很重要。這個計劃就在我們面前擺放的黑色筆記本電腦上。呃，它是一款CD-ROM游戲。

這款名為《is.C3: 借助商業、文化和社區創造一個偉大的地區》的游戲，是一個模擬展示。其內容是，一位時年44歲的硅谷大亨遭遇車禍，不幸身亡，留下一筆高達5億美元，旨在支持藝術事業的捐款。如何花費這筆錢，將決定硅谷是否可以達到“文藝復興時期佛羅倫薩的文化高度。”

該組織執行董事約翰?克萊德勒介紹說，作為長達7個月勞動的結晶，這款游戲旨在勸說大約1000名硅谷領導人“接受文化很重要這一理念”。在一些地方，這種勸說或許是不必要的。但硅谷很需要，克萊德勒聲稱。“我們本可以創造一個PPT展示。但互動媒體是硅谷的方言。我們試圖接觸的很多人都玩游戲——電腦游戲。這是硅谷文化的重要組成部分。”

對于這個話題，你只需問問薩利?奧斯伯格。作為圣何塞兒童發現博物館的執行董事，她運營著一家價值450萬美元，擁有70名員工和950萬美元捐款的企業。然而，當一些嶄露頭角的科技慈善家前來參觀訪問時，他們經常問奧斯伯格，她是不是一名志愿者。“他們無法相信，這是一家真正的企業。”她笑著說。“他們的帶寬正在擴大，還有很長的路要走。”

早前，高科技精英的慈善事業所反映的，只是捐贈者本人的狹隘利益，而不是社區的實際需要。即使現在，科技企業大約一半的捐贈往往是電腦和軟件。盡管非營利性組織樂于接受電腦，但很多組織沒有錢聘請炙手可熱的IT人才。希羅說，“對于社區的真正需要，硅谷企業還理解得不夠透徹。”就連比爾?蓋茨也對科技慈善家癡迷于全球的“數字鴻溝”表示不屑。最近，在西雅圖舉行的一個會議上，這位微軟公司創始人尖銳地指出，對于許多還沒有解決溫飽問題的人來說，高科技設備并非頭等大事。

社區建設

希羅尤為重視的一個議題是，如何防止高企不下的生活成本逼迫眾多中產階級紛紛逃離，進而使得硅谷最終成為一個只有超級富豪才住得起的門禁社區。“我們有可能淪為一個只剩下富人及其仆人的排他性社區。”希羅說。

在位于東圣荷西的梅費爾區，希羅獨特的社區建設品牌遭遇到最為嚴峻的考驗。正是在這個擁有6500人，主要由拉丁裔構成的低收入社區，硅谷社區基金會開始實施其最復雜和雄心勃勃的項目。

這是希羅的“高價證券”之一——高風險，但有潛力獲得巨大的回報。策劃于1997年的“梅費爾改進計劃”旨在永久性地提升整個街區的前景，包括其街道、住宅、學校和居民。該計劃預計需要超過1500萬美元的公共和私人資金（包括惠普基金會提供的500萬美元），涉及76個獨立改造項目，列舉一個抽樣：提高識字率、增加路燈、雇用交通協管員、改造一個被忽視的社區花園、建立家庭日托中心、進行健康檢查、提供理財咨詢、繪制壁畫、提供高科技職業培訓，以及培養居民的領導能力。所有這些都將被精心監測，基金會將基于數百個精心設定的定量基準，定期評估項目進展。

就本質而言，社區基金會正在扮演總承包商的角色：管理基金，為額外的“投資機會” 尋找捐助者，并監督這一切。希羅將梅費爾視為一個旗艦項目，“我們所做的一切事情的縮影。”具體的項目清單和目標，均是社區自身制定的，而不是基金會頒布的。所有這一切旨在建立“連接”——在拉丁裔和越南裔鄰居之間；在居民和公共機構之間；在居民與企業職業培訓計劃之間。那個此前被忽視的社區花園已經成為“附近居民的客廳。”希羅說。

升級一個社區并非易事：經濟前景的改善將鼓勵許多居民遷出，除非梅費爾成為一個更具吸引力的社區。只是改善社區環境，但沒有增加家庭收入，將招致“高檔化”。“關鍵是可持續性。”基金會董事利奧?查韋斯說。“我們正在努力那些導致貧窮固化的問題。”退出戰略是個大問題。“我們將密切觀察當惠普基金會的資金耗盡，社區基金會的員工退出之后，這里將發生什么事情。”

風險慈善模式

在希羅辦公室所處走廊的那一頭，43歲的Infoseek公司創始人史蒂夫?基爾希創建了隸屬于社區基金會的史蒂夫和米歇爾?基爾希基金會。基爾希是硅谷慈善事業最熱誠的傳福音者，也是希羅最熱情的盟友之一。他已經留出7500萬美元凈資產，用于多種多樣的慈善事業——比如United Way（他率先為這家慈善組織捐助100萬美元，以解決其資金缺口）；跟蹤有可能撞擊地球的行星。在其新公司Propel位于圣何塞的辦公室，基爾希激烈地抨擊“一毛不拔”的億萬富翁，還抱怨說，他曾經懇請一位互聯網公司CEO將一大塊股票投入慈善基金，但遭到無視。這位CEO的凈資產一度達到20億美元。“對他來說，捐贈1%的凈資產根本就不是事兒。”基爾希抱怨說。他迅速地說出一連串需要效仿他的科技億萬富翁的名字。“我幾乎不是硅谷最富有的人。”他指出。“絕對不是。”

基爾希所扮演的是挑釁者的角色，他不停地戳指硅谷的良心。希羅則尋找新的方式擴大捐助者群體。例如，多年來，他一直在竭力招攬忙碌的新科技百萬富翁主動敲響他的房門。現在，他開始主動出擊。基金會安排一位“捐贈輔導員”進駐思科公司龐大的企業園區。這是一片無可爭議的沃土：思科在硅谷擁有1.8萬名員工，其飆升的股票甚至讓一些秘書都成為百萬富翁。希羅還試圖挖掘硅谷印度裔社區的財富——約20萬社區成員估計擁有總值達500多億美元的凈資產。希羅表示，許多移民希望支持家鄉的事業，但缺乏這樣做的途徑。因此，雖然社區基金會很少捐款支持本地區之外的事業，更遑論海外，但希羅正在嘗試著開發一只基金，以方便印度捐助者回饋祖國，并支持硅谷的慈善事業。

他的基金會還成立了一個備受關注，面向年輕捐助者的“風險慈善”團隊：硅谷社會風險基金，簡稱SV2。SV2以西雅圖和奧斯汀的同行為榜樣，吸引了100名風險投資家和企業家作為其“合作伙伴”。每人每年至少捐贈2500美元。社區基金會把這筆錢匯聚在一起，并輔之以匹配資金，以提供贈款。在“風險慈善”模式下，捐助者對非營利性機構實施風險投資公司經常進行的那種審查，然后提供專業知識，以推動其“投資”最大化。它堅持建立“指標”來衡量回報，并尋找“可擴展性”和“退出策略”。

風險慈善模式已經吸引了大量的嗡嗡聲，以及質疑聲。總部位于舊金山，資產達2.4億美元的沃爾特和伊利斯?哈斯基金會執行董事布魯斯?西弗斯表示，多年來，思慮周到的捐贈者一直在嚴格地審查他們所資助的非營利性組織，并堅持要求良好的業績。但他擔心，嘗試將風投原則應用于非營利性組織，很容易走入歧途。“在商業世界里，有一個簡單的測試：你賺到錢了嗎？社會世界并沒有一個與之對等的東西。”西弗斯也懷疑互聯網精英們究竟帶來了多少有用的知識。“僅僅因為他們依靠開發軟件程序賺了大錢，并不意味著他們懂得如何開發教育項目。他們是瓷器店里的蠻牛，很可能會把事情搞砸。”西弗斯說，他聽聞有一家非營利性組織的主要商業捐助者這樣詢問該組織高管：“給我說說，在這個領域，我們如何碾壓競爭對手？”

當然，所有這些危險仍然是理論上的——這是一個不要過于極端化地使用某種方式的問題。希羅本人也對風投慈善的某些信條抱有一絲疑慮——如何才能衡量一家博物館的“產品”？但他很高興地看到一批新人投身慈善事業。畢竟，SV2的意義不僅僅在于資助非營利性組織，另一個至少同等重要的作用是，它還能夠培養一批新的捐助者。eBay的斯科爾將SV2稱為“年輕慈善家的訓練輪”。

這家只限于受邀請人群的組織，已經多次登上全國性媒體頭條——事實上，甚至在它發放首筆贈款之前，它就獲得媒體關注。（首筆贈款為22.5萬美元，受益者是當地一家非營利性組織，其宗旨是幫助出身于低收入家庭，成績不佳的小學生。）好幾位基金經理試圖加入SV2，以期結識這些年輕的百萬富翁。但沒有人想被搭訕。“我們為成員提供的是一個安全的地方。”該組織一位成員說。另一位成員表示，SV2需要精心招攬“理想的成員，即熱門CEO和熱門風投家。”

“就慈善捐贈而言，我們沒有歷史，也沒有榜樣。”SV2聯合創始人，風投公司Mayfield Fund管理合伙人鄺伋榮說。“我們希望SV2能夠縮短這個學習過程。”

希羅表示，假以時日，SV2所采用的風險慈善模式可能會不斷演變。“隨著他們對慈善事業的了解不斷加深，他們的慈善捐贈可能會變得更加傳統。” 這只是利用硅谷令人驚嘆的財富的另一種方式。真正迫切的問題是，如何創造一個藝術繁榮發展，中產階級具備購房能力，窮人活得有尊嚴，而且能改善自身處境的社區。要想讓所有這一切成為現實，希羅說，“我們需要創造一種文化，讓慈善成為硅谷的生活方式。如果我們不這樣做，人們會說，‘我不敢相信這些家伙竟然搞砸了。’” (財富者文網)

譯者：Kevin

本文最早發表于2000年11月27日的《財富》雜志。

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.'”