🌟 Hey there! This is a subscriber-only edition of our premium newsletter designed to make you a better founder, investor, and technologist. Members get access to the strategies, tactics, and wisdom of exceptional investors and founders.

Friends, 

I could not be more excited to share two pieces of news with you. 

Firstly, we are launching a brand new series called “Letters to a Young Founder.” After the extremely positive reception from readers to the “Letters to a Young Investor” series, we’re expanding the format to speak to current and future entrepreneurs. 

Fundamentally, we believe that the best tactical and strategic advice comes dressed as a story or recollection. “Letters to a Young Founder” brings insights to life from the perspective of exceptional, time-tested founders.

Secondly, we’re launching the series with the one and only Vinod Khosla. Over the past four decades, Vinod has been a critical figure in the tech industry, both as an entrepreneur and investor – or “venture assistant,” as he prefers to be called. Vinod co-founded Sun Microsystems in 1982, a hugely successful and influential computing firm responsible for inventing or popularizing essential technologies like Java, Unix, RISC processors, and many more. 

At Kleiner Perkins, Vinod incubated several successful businesses and made some of the greatest VC investments ever. He continued that hot streak at his own firm, Khosla Ventures, which remains a top-tier franchise today, responsible for backing OpenAI, Stripe, Block, DoorDash, Faire, and countless others. 

Over the next four correspondences, Vinod and I will delve into these chapters of his life and the stories behind them. In the process, we’ll surface vital lessons for the founders building the great businesses of tomorrow. (Given Vinod’s career, there will also be a huge amount of investing wisdom.)

To ensure you receive all of Vinod’s wisdom and maximize the value of these lessons, sign up for our premium newsletter, Generalist+. Not only will you get Vinod’s full insights delivered directly to your inbox, you’ll unlock the wisdom of our full catalog. That includes exclusive interviews with legends like Reid Hoffman and tactical “Founders Guides” showcasing advice from the entrepreneurs running AngelList, Vanta, Mercury, and others. Our work is designed to make you a better investor, founder, or technologist. 

Sign up for just $22/month to unlock Generalist+’s unique narrative intelligence. 

Lessons from Vinod

1. Embrace risk. If Vinod had followed his father’s advice, he would have joined the Indian army. His willingness to leave India and try his hand at entrepreneurship in the United States laid the groundwork for an extraordinary career. Founders must often act against the wishes of their family and friends to build their businesses. 

2. Be hungry for information. Growing up in Delhi in the 1950s and 1960s, Vinod didn’t have easy access to information from the rest of the world. That didn’t stop him from learning. As he shares, he went to extreme lengths to find stories about entrepreneurs. Great founders are learning machines, willing to overcome obstacles to get the information they need to develop. 

3. Failure doesn’t matter. Vinod started a business described as a “disaster” by his co-founder, but it’s rarely discussed. Why? Because it doesn’t matter, Vinod says. Entrepreneurs are remembered for their successes, not their failures. The most important thing is to try – something many people don’t dare to do.

Mario’s letter

Subject: The making of an entrepreneur
From: Mario Gabriele
To: Vinod Khosla
Date: Friday, March 1 2024 at 14:04 PM EDT

Vinod, 

It feels slightly surreal to be writing to you. As an avid student of Silicon Valley’s history, I’ve studied your accomplishments at Sun Microsystems, Kleiner Perkins, and Khosla Ventures in detail. I have great respect for the impact you’ve had on our ecosystem and the world at large. I couldn’t be more excited to explore those chapters of your life, and share the lessons learned along the way with current and future founders. 

If I’d been a little bolder, we might have had a version of this conversation six years ago. I vividly remember seeing you at the first Y Combinator Demo Day I attended in 2018. I didn’t have the courage to introduce myself back then and regretted it for a long time afterward. I feel fortunate to have a second chance now. 

Over the coming months, I cannot wait to hear the lessons and lore you’ve accumulated from being on the frontline of innovation over the past forty-plus years. You’ve founded hugely consequential companies, assembled insanely high-performance teams, landed some of venture capital’s biggest-ever hits, and built a franchise investment firm. But such successes do not arrive overnight and even great founders often have to pay their dues. In this first correspondence, I’d like to focus on the years before Sun Microsystems and the many wins that followed. 

One of my persistent obsessions is the provenance of exceptional entrepreneurs. Where do they come from? What were their families like? What were they interested in as children? How would they describe their younger selves? What were their earliest startup endeavors? What difficulties did they encounter? How did they manage their first commercial failures? Hidden in these anecdotes and recollections, it feels as if you can often find the making of an entrepreneur. 

Given your profile, others have written about these subjects. I know, for example, that you were raised in India, the son of an Army officer, and that you headed to America for your Master’s degree and MBA. I also know that before you founded Sun Microsystems, you tried your hand at a soy milk business, started Daisy Systems, and then followed it up with the lesser-known Data Dump. These are the beats of a biography, but I can only imagine that there is greater depth in each of these moments. 

For example, did you ever consider following your father’s footsteps into the Army? Did he approve of your journey into entrepreneurship? Did you have any role models in the Indian business world (I know you’ve talked about Andy Grove as an inspiration, though obviously he was based in the US)? Where did the soy milk idea come from and how far did you get with it? Why did your Data Dump co-founder Scott McNealy call it a “huge disaster,” and what lessons did you take from it? How did it set the stage for Sun? 

For those earlier in their entrepreneurial journey, I think there’s real value in understanding your story and early activity with finer fidelity. 

Sending you my very best on a sunny, windy day in New York state. 

Best,

Mario

Vinod’s response

Subject: The making of an entrepreneur
From: Vinod Khosla
To: Mario Gabriele
Date: Tuesday, March 26 2024 at 10:41 AM PDT

Hi Mario,

I’m glad to have this conversation with you. 

I am happy to write this for entrepreneurs because I have never considered myself an investor. In fact, I call myself a “venture assistant,” which used to make my former colleague and friend John Doerr mad. He thought it sounded weird, but it explains how I think of my job. I assist entrepreneurs, working with them to build bigger, better, and more impactful companies.

You asked about my early life and the companies I founded before Sun. The truth is that while I was growing up, I basically never met anyone outside the Indian Army. Nobody I knew had a business or tech background, and there weren’t any role models in India at that time. Today, you have Indian CEOs at Microsoft, Google, IBM, Adobe – the list goes on. We just need Meta and Apple. But that wasn’t the case when I was a kid. 

My father definitely wanted me to join the army. He had been orphaned at two or three years old and was conscripted at age 15 into the British Army before getting shipped to Egypt to fight under Lord Mountbatten. He thought joining the army was the best thing that ever happened in his life – it was family, security, all the things he didn’t have.

I was always intrigued by science. That’s actually how I first became interested in technology. When we were living in the Delhi cantonment – a military section of the city – I used to take a bus to an old part of Delhi. I used to call it the “slice of life” Delhi because you could find all these used items, including magazines to rent. They were coming from the U.S. and Europe, so they were old. How old depended on the type of magazine – if it was something like Electronic Engineering Times, it might be a year or two years old; if it was Time, it might be only six months old. I would rent the magazines, read them, and then take the long bus journey back the next weekend. 

I’ve spoken before about how, in those magazines, I read about Andy Grove at Intel and was inspired by his story. Here was an immigrant who had founded a cutting-edge technology company in America. Once I moved to America and began my journey, I got to know Andy pretty well and told him that story. I wouldn’t say we were close friends, but we’ve known each other for a long time. 

He’s very much a no-nonsense person, which I love. Every year at Khosla Ventures, we have our CEO Summit in May. I remember calling him in 2007 and asking if he’d speak to our founders. He responded, “Sure, but I’m going to completely disagree with your focus on biofuels. I’m going to talk about why electric is much better.” I said, “Go for it.” He’s so direct like that. ...