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Andy began his legal career at Cravath, Swaine & Moore in 1987, where he was exposed to various legal practices under the mentorship of Bob Roseman, a top securities lawyer. His initial year involved due diligence, negotiations with regulators, and assisting in merger and acquisition strategies. Over time, he honed skills in drafting complex documents, compiling federal filings, and researching legal issues.

Despite a $175,000 annual salary, Andy grew disillusioned with the industry's indifference to costs, which were passed on to clients. Extravagant expenses were routine, from ordering dinners from upscale restaurants to hiring limousines for trivial tasks. Andy saw this as a reflection of a culture where money symbolized authority, and the more that was spent, the more prestigious the lawyers appeared. He questioned whether such spending was justifiable, even though it was a small fraction of the large sums involved in the transactions.

Amidst a growing sense of disillusionment, Andy found love with Liesbeth, a Dutch woman working at the UN in New York. When she returned to Amsterdam in late 1989, Andy sought a transfer to his company's London office to be closer to her. His timing was perfect as his employer, Cravanth, needed him in London to help with a client, BAT Industries, facing a hostile takeover. Andy worked on this intense corporate battle for nearly a year until it ended with the junk bond market's collapse.

After his European stint, Andy and Liesbeth chose not to return to New York immediately but instead traveled through India, Nepal, and China for six months. Post-travel, they settled in Holland and got married. It was there that Andy discovered witbier, a Belgian beer with a distinctive taste from Spanish orange peels and coriander, perfect for hot days. Enthused by the beer and encouraged by friends who enjoyed it at his wedding, Andy decided to introduce witbier to the American market, despite being on leave from his corporate attorney job and lacking business experience.

Andy embarked on an ambitious journey to launch his own beer company, starting with a solid business plan and a private placement memo to raise $500,000. He invested $75,000 of his own savings for a 40% stake and sought the remaining funds for 60% of the shares.

Facing initial skepticism from potential investors due to the absence of a product to sample, Andy cleverly used generic witbier from Holland to demonstrate the market's interest in such a beer. This move, coupled with a compelling story, helped him transport the beer to the U.S. without incurring extra charges, thanks to the sympathetic staff of KLM.

Andy Klein, co-founder of Spring Street Brewing, faced the challenge of raising capital for his company's expansion and the launch of a new beer, Amber Wit.

After a moderately successful round of fundraising, which garnered $400,000, Andy considered a novel approach inspired by Ben & Jerry's: selling stock directly to consumers. With his expertise in securities law, he prepared to file a registration statement with the SEC and state regulators, a costly process for small startups, but feasible for Spring Street due to Andy's ability to handle the legal work himself.

Despite the potential issue of share liquidity, as the company was too small to list on Nasdaq and unlikely to attract market makers, Andy proceeded with a unique strategy. He planned a public offering of 2.8 million shares at $1.85 each, which would be publicly tradable but not listed on an exchange, thus avoiding the pressures of being publicly listed.

After the stock offering for Spring Street Brewing closed, its website continued to attract significant attention, leading Andy to consider an innovative idea. Observing the continued interest in purchasing the company's stock, he proposed creating a digital platform, Wit-Trade, for trading shares among existing and potential shareholders without commission.

Despite not being listed on a traditional stock exchange, Wit-Trade aimed to facilitate transactions through a simple website featuring two bulletin boards for buyers and sellers. The initiative, touted as the first-ever digital stock market, launched on March 1, 1996, drawing considerable media attention.

Andy's innovative idea was to create an Internet-based investment bank, Wit Capital Corporation, to help early-stage companies find investors and provide share trading liquidity without the traditional costs associated with brokers. This concept aimed to revolutionize corporate finance by eliminating commissions, fees, and middlemen. Despite potential initial skepticism from larger companies, Andy believed that the adoption of this model by a community of investors would eventually attract major corporations.

The idea gained traction after being featured in a print article in March 1996, leading to the formation of Wit Capital with significant contributions from David Blumberg, a veteran of Merrill Lynch, and Bill Brown, one of Spring Street’s original backers. They raised $1 million from investors for a 10-percent stake in the company.

Recognizing the need for experienced leadership to build a stand-alone retail brokerage, David Blumberg and Andy turned to Julie Oliver, a seasoned professional from Arthur Andersen and Salomon Brothers, to join Wit Capital as CFO and head of retail brokerage. Wit Capital aimed to establish a fully automated discount brokerage, offering access to digital stock markets, news, initial public offerings, and venture capital investments, competing with firms like E-Trade Securities and AmeriTrade. The strategy was to attract investors and high-quality companies, thereby creating a self-sustaining cycle of growth and liquidity in the digital stock market.

Wit Capital's emergence as an Internet investment bank marks a significant shift in the financial industry, reminiscent of the early days of U.S. commerce where trading took place under a buttonwood tree. This modern approach democratizes access to investment opportunities, allowing individual investors to compete with institutional ones and brokers on equal footing. Internet investment banking is poised to transform capital formation and corporate financing, especially in areas like Initial Public Offerings (IPOs), Venture Capital Offerings, Private Placements, and Digital Stock Markets.

In traditional IPOs, companies relied on investment bankers to access significant finance, giving bankers leverage as gatekeepers to capital. They often underpriced IPOs to ensure a post-IPO share performance surge, benefiting institutional clients and generating substantial fees. Internet investment banks, however, can open IPOs to the public, distributing information more effectively and allowing transparent pricing through an open auction system.

Andy Klein, a visionary in the digital space, believes the Internet's true potential is just beginning to be realized. While it connects businesses and consumers directly, reducing costs, the real game-changer, according to Klein, is the communities it fosters. He sees these online communities as the "killer app" of the web, creating new kinds of interactions and opportunities.

Wit Capital is on a mission to harness this power by building a community of savvy investors. This network will not only engage in high-quality transactions but also provide a ready-made base of shareholders or customers for new ventures. As the community grows, it will generate additional value and benefits for its members, attracting even more participants in a self-reinforcing cycle.