Lessons From Luminaries: Bill Gates on Microsoft, Mistakes, and Advice For Today’s Founders

We are honored to have Bill Gates, one of the most successful entrepreneurs of all time, among our small group of luminary LPs whose financial capital and engagement power the next wave of Village Global founders.

Recently, Bill joined Julia Hartz, co-founder and CEO of Eventbrite and friend of Village, on stage in front of our founders and Network Leaders in San Francisco. They covered his entrepreneurial journey starting Microsoft, his current perspective on the tech landscape, and his views on philanthropy and social change more broadly. Some of the highlights of the conversation are below.\

Gates explains his thinking on work-life balance for founders and whether he would do things differently if he could do things over again.

“I think you can over-worship and mythologize the idea of working extremely hard. I didn’t believe in weekends or vacations, but once I got into my thirties I could hardly even imagine how I had done that. Now I take lots of vacations. My twenty year-old self is so disgusted with my current self.”

He says that he knew all the license plates of the individuals working at Microsoft at that time and could tell you who had been working evenings and weekends. He says that was not popular and would probably not recommend today’s founders work as hard but that much of that hard work transformed Microsoft into what it is today.

He admits his “greatest mistake of all time.”

“Particularly for platforms, these are winner take all markets. The greatest mistake ever is whatever mismanagement I engaged in to cause Microsoft to not have what Android is.”

He points out the leverage contained within software platforms, and when creating them, small mistakes can magnify themselves to turn into something “absolutely gigantic.”

Julia asks which changes he’s seen in entrepreneurship over the last few decades and what he’s learned from the next generation of founders.

“It’s nice that the idea of being a founder is a thing. That you can meet other people doing it, that if the first one doesn’t work out, it’s okay to do a second one, and that there’s all these people who want to hand you money now. ”

He points out that with lower barriers to entry, it also means that there is much more competition and that even if you have the requisite expertise and can build a team around you, you are competing against dozens of early-stage startups trying to solve some of the most difficult problems, like discovering drugs through machine learning.

He also walks through his thinking on whether as an early-stage founder, you should be thinking about giving back as soon as you can, or whether you should focus on trying to change the world through business and look to compound your returns within your company.

They move on to talking about philanthropy and development. Gates explains how similar his work at Microsoft is to his philanthropic work.

“I get to use 80% the same type of thinking that I exercised at Microsoft. It’s backing engineers, getting a sense of the team and asking, ‘what needs to be added to that team?’ … [but] our profit is lives saved, as opposed to a monetary measure.”

He points out that people dramatically overestimate the amount that the US spends on foreign aid and talks about how astonishing it is to learn for the first time that $500 can save a life in a developing country.

“By 2050, 90% of the extreme poor will be in Africa. Nigeria will be the third largest country in the world. Asia’s population is mostly going to stay flat or shrink. The world’s poor will increasingly be on one continent.”

He talks about some of the most important unsolved problems that people don’t appreciate in development and talks about the need for global cooperation and why an optimistic and “possibilist” attitude is required to solve international problems.

“The group that is least aware of the improvements in the world are professors at US universities. When they survey people to ask whether they think child mortality and the like has decreased, the people who are the furthest below 50% are professors at US universities, who manage to get all the way down to 20%. It’s the lowest group ever tested.”

He talks about the challenges that the US faces in education.

“The US has the highest dropout rate both in high school and college. We actually have more people who enter higher education than any other country but we have 12 other countries that graduate more people than we do. In terms of cost of education, the person who is in bad shape is the one that paid that cost, but didn’t get the degree.”

The majority of his philanthropic efforts are focused on improving health in the developing world, but the centrepiece of his work in the US is improving education. He admits that improving education has been “way harder than we imagined,” talks about their efforts in improving education, and explains why it’s such a difficult issue to solve.

He also talks about his book recommendations, how Microsoft approaches AI, and the role that elite universities might play in improving education overall in the US.

“The personal agent that knows everything about you and can proactively assist you in all areas of your life is the paradigmatic thing that collapses the current order of software industry.”
“Stanford doesn’t have a dropout rate, because they don’t let people in who would drop out. They succeeded the day the admissions department was done. They didn’t make those people hard working, they just picked hard working people.”

A handful of our founders met with Bill one-on-one afterwards to get advice on their companies. Here’s what they had to say about their experience meeting him:

Check out more photos from the event.

Village Global is an early-stage venture capital firm backed by some of the world’s most successful entrepreneurs. We’re not a traditional VC. We’re a network. From how we invest in startups to how we help founders — we operate as a network. When you raise money from Village, you’re not just getting money, you’re joining a network of the world’s most successful founders, including Bill Gates, Mark Zuckerberg, Sara Blakely, Diane Green, Reid Hoffman and others.

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