Sergio Monsalve, Roble Ventures & Stanford | What Makes Stanford and Silicon Valley Special in the Startup Ecosystem

The audio and video are in Spanish. These notes are a translation.

What makes Stanford unique?

To try to answer this question, today I spoke with Sergio Monsalve, Founding Partner of Roble Ventures, a venture capital fund that invests in founders creating technologies for education and work. He is also a professor of entrepreneurship at Stanford.

Sergio has been an investor in major companies such as Udemy and Kahoot!.

We talked about Stanford’s role as a cradle of founders, what makes it so special, and how you can connect with investors in Silicon Valley if you did not attend this university.

This episode condenses more than 20 years of experience in Silicon Valley. I hope you enjoy my conversation with Sergio Monsalve of Roble Ventures.

Youtube Timestamps*

[1:05] - Silicon Valley and Stanford

Sergio has played multiple roles in his career: executive, professor, founder, investor, and he is also involved in social initiatives.

What do you need to know to understand the life he has led?

He arrived in Silicon Valley more than 20 years ago.

How has Silicon Valley evolved since he arrived?

Silicon Valley is the global center of technology and entrepreneurship.

Sergio is Mexican and invests both in the US and in Latin America, and he has lived most of his life in the US.

Does being in Silicon Valley give a founder or a professional a considerable advantage?

Mercado Libre, Nubank, Cabify, and several more of the successful startups in Latin America and the world have connections to Stanford.

Being on the inside. What would he say is Stanford’s secret recipe?

Stanford is in another category when it comes to starting a company, in terms of the resources and connections it can give a founder.

Is there anything else he thinks the university does that allows it to position itself as a cradle of unicorns?

Talking with founders, many feel it is “unfair” how easily a founder who comes out of Stanford (and other universities at this level) can raise capital and have access to Silicon Valley.

Sergio cares about diversity and has even invested in founders without that background.

What does he tell those founders when they feel that as they go to raise capital or talk with investors?
What does he recommend founders do to connect with investors or advisors in Silicon Valley, without going through a university like Stanford?

The San Francisco and Silicon Valley ecosystem has a different culture from the ecosystem of Mexico or Peru, even though they are startups and technology.

What would Sergio recommend to someone who wants to come to Silicon Valley to work, start a company, or simply look for opportunities?
What does he think is needed on the mindset or culture side, does he think there are particular things that Silicon Valley embraces more, and that if you have them it would be much easier to connect and build relationships?

[27:24] - Investing in Unicorns

His first years as an investor were quite difficult.

Sergio told us what happened and how he lived through this stage

Sergio is very methodical in the way he evaluates investments, and we have heard him say that he likes to “predict the future.”

What is a framework or mental model for thinking about the future when you want to start a company?
Sergio told us what the 5 or 6 criteria are that he looks for in a founder’s mindset.

[44:41] - Advice for Students

He is a professor of one of the entrepreneurship classes.

What is the piece of advice he finds himself giving most in his day to day as a Stanford professor to his students?

[46:03] - Rapid-Fire Questions

What is the worst entrepreneurship advice he has been given?
What has been the most influential book on his path through the world of startups?
What would he like to change about the world of startups?