Inside the Deal: VCs that led some of the biggest deals of all time

September 27, 2023
Startup Investing

This week we're taking a slightly different approach for our Inside the Deal series. We're highlighting six of the top investors from the 2023 Midas List, along with their most notable deals.

These investors have cemented their names over the years as some of the best VCs, negotiating the most profitable and impressive deals. To qualify for the Midas List, Forbes says investors are ranked by their portfolio companies that have gone public or been acquired for at least $200 million over the past five years, or that have at least doubled their private valuation since initial investment to $400 million or more over the same period.

Let's take a look six of the top VCs in the world.

Neil Shen

Who is he?

Neil Shen is a Chinese venture capitalist and entrepreneur. He is the founding and managing partner of the Chinese arm of Sequoia Capital. He co-founded Ctrip and Home Inn.

He has led Sequoia China to invest in many successful companies, including; Alibaba, Sina, ByteDance, Meituan,, Pinduoduo, Qihoo 360, DJI, Vipshop, and J&T Express. 

His best deals:

  • ByteDance, the parent company of TikTok
  • Shein, a fast fashion retailer
  • Meituan, a food delivery company

3 of his most powerful quotes:

"Entrepreneurship is about speed… So, if you like to do something and you feel like something is calling you inside, you better do it, right away. And that’s all about entrepreneurship."

"You will always make mistakes, but as long as you capture all the major trends, you’ll be doing very, very fine."

“The best way to find business partners is to look for individuals who match your business interests and have a wealth of knowledge and experience in the niche."

Vinod Khosla

Who is he?

Vinod Khosla is an Indian-American businessman and venture capitalist. He is the founder of Khosla Ventures, the Silicon Valley venture capital firm. He is also the co-founder of Sun Microsystems. 

Khosla made his wealth from early venture capital investments in areas such as networking, software, and alternative energy technologies. 

His best deals:

  • Affirm
  • Square
  • DoorDash
  • Instacart
  • OpenAI

A few failures Khosla talks about:

One of his early failures was a soy milk venture in India, which did not materialize as expected. Another early setback was with Data Dump, a company co-founded with Scott McNealy, but it never got off the ground.

Despite these initial failures, Khosla remained resilient and founded Sun Microsystems just three months later. Khosla's career also includes failures with ventures like Asera, BroadBand Office, Excite@Home, and Dynabook. 

Laurel Bowden

Who is she?

She was the first European partner of 83North, which manages $2.2 billion of assets in Europe and Israel.

Her best deals:

  • Doordash's $10 billion acquisition of Wolt (2021)
  • PayPal's $2.2 billion takeover of iZettle (2018)
  • Celonis's $1 billion raise at an $11 billion valuation

Garry Tan

Who is he?

Tan was born in Fremont, California in 1981 to Singaporean immigrants. He started programming at age 14 and found his first job by cold-calling the Yellow Pages. He is the founder and managing partner of Initialized Capital, which he left in August 2022 to become the CEO of Y Combinator.

He attended Stanford University from 1999 to 2003 and graduated with a bachelor's degree in Computer Systems Engineering. 

His best deals:

  • Coinbase
  • Instacart
  • Flexport

Mary Meeker

Who is she?

Mary Meeker is an American venture capitalist and former Wall Street securities analyst. She is the founder and general partner at BOND, a San Francisco-based venture capital firm. She focuses on investments in high-growth technology companies.

Her best deals:

  • Plaid and Canva stand at valuations of $13.5 billion and $40 billion, respectively.

Most recent investment:

Meeker recently invested in Yassir, an African super app that provides a range of on-demand services and contract management startup Ironclad, valued at $3.2 billion.

Luciana Lixandru

Who is she?

With roots in Romania, Lixandru is a prominent figure in the venture capital world. In March 2020, Luciana Lixandru made a significant career shift by departing from her long-standing position at Accel's London team to play a pivotal role in establishing Sequoia's inaugural European office.

Her best deals:

  • Led the Series A for Bucharest-founded software company UiPath, which went public in February 2021. It was valued at $35 billion at IPO, making it one of Europe's largest ever.

Other notable investments:

  • digital whiteboard tool Miro ($17.5 billion valuation)
  • virtual event platform Hopin ($7.75 billion valuation)
  • food delivery company Deliveroo (IPO 2021)

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