Sergio Monsalve: "Helping others go the distance"

Sergio Monsalve is the Founding Partner of Roble Ventures , a Silicon-Valley based seed stage fund focused on the future of work. Prior to that, he had a long career as a Venture Capitalist at Norwest Venture Partners and as a founder and tech executive at companies like Cymerc, Portal Software, eBay, and Photobucket. Sergio has an undergraduate degree from Stanford University in Industrial Engineering and an MBA from Harvard University. Sergio was born in Mexico City and moved to San Diego, CA in Junior High, when his father, who was a serial entrepreneur, started a business in Tijuana/San Diego in the 1980s.?

When Sergio arrived in San Diego as a teen, he didn’t speak English, and while there were a lot of Mexican and Mexican American kids at his public high school, he didn’t quite fit in. He found his tribe amongst the kids in the International Baccalaureate program, “The Nerds,” and in his spare time he dedicated himself to swimming competitively. He had aspirations of competing in the Olympics - but at 5’6”, those dreams evaporated by the time he was 18 years old.

Sergio wanted to experience the east coast for college and wanted to apply to the Ivy League schools, but as the eldest of three kids - and the oldest son, his parents were not used to the concept of boarding for college and wanted him to live at home. They told him to attend either UCSD or any college in San Diego - and to come home for lunch. He was able to convince them to let him attend any California college and come visit often. He applied and was accepted to all his prospective colleges and he chose to study engineering at Stanford. When he arrived at Stanford, he felt like an imposter because everybody was wealthier and those who attended the east coast boarding schools, were better prepared. This was only made worse when his father’s business - impacted by lower-cost competitors out of China - started to go out of business. His father told him that he could no longer pay for Stanford. So Sergio dedicated his summer of Freshman year to package up his father’s business and sell it. The sale of his dad's business exposed him to what it was like to do small-scale M&A, which Sergio really loved. His father sold his business by the Fall which allowed him to pay off his debts but left him with very little money.? Sergio scrambled to pay for college by working with financial aid to apply for scholarships and loans - he graduated Stanford with over one hundred thousand dollars of debt.?

While at Stanford, Sergio learned how to sell by joining a club? where he would help connect Silicon Valley technology companies with International Summer interns. He got to know different businesses like Intel, and Oracle - and he fell in love with the possibility of working in tech some day. After he graduated with a degree in Industrial Engineering, he went off to New York to work on Wall Street at Morgan Stanley in the M&A department. And then he attended Harvard Business School - mainly to scratch the itch of attending a school on the East Coast. While the academic rigor and classes were interesting, at Harvard he focused on building connections and improving his social capital.

When he graduated from Harvard, he went back to Silicon Valley and got a job at a Pre-IPO company called Portal Software. The company went public in ‘99 and he cashed out enough to pay off his Stanford, and HBS school debts which at the time had ballooned to hundreds of thousands of dollars.? After a short stint at Portal, he took a leap to become an entrepreneur. He co-founded Cymerc, an online marketplace for tech hardware. He raised a large Series A round of $7M and he saw his paper net worth become millions. And then… the Dot-com bubble burst in 2001 ands he remembers that in one day 90% of his net worth disappeared. He was able to take his experience and become a category head at eBay for the same hardware vertical he had focused on at Cymerc. Back then eBay was the hot place to be and it was the only profitable public internet company at scale. At eBay, he was successful and was promoted several times while getting ever more options; as the eBay stock price emerged from the ashes over his 5 year tenure there, his stock options grew and at a certain point he decided that he was not excited about being on the large corporate hamster wheel. So he asked executives like Meg Whitman, the CEO at the time, and Jeff Jordan, President of the US business, if he could work on frontier related projects including incubations of new marketplaces, investments and acquisitions that would continue to help position eBay for the future. As part of that role, he discovered PhotoBucket, and he jumped at the opportunity to join this small but fast-growing photo-sharing company. He helped them raise a bit of capital from one of his early backers at Cymerc, Trinity Ventures and then a little over a year into the company, it was acquired by News Corp for $300M in cash. His backers made a solid quick return, and as Sergio says, while he lost them money at Cymerc, they more than made it back with PhotoBucket.

After his experience at PhotoBucket, Sergio became an EIR at the same fund who had funded him at Photobucket and Cymerc. Initially he thought he would start another company, but he became enamored with venture capital and after six months as an EIR, he joined Norwest Venture Partners full-time as a Principal and later as a Partner. He stayed at Norwest for over a decade and made early Investments in Udemy , Adaptive Insights, Kahoot! and many others; these three companies exited for a combined total of $8Bn and generated over $450M returns for Norwest. But as the fund size at Norwest continued to grow, so did the check sizes Norwest was writing. Sergio's interest as an ex-entrepreneur was in working with early stage entrepreneurs. So he decided to build a class at Stanford which he would teach to undergraduate and graduate students interested in entrepreneurship. This Spring 2025 will mark the 7th anniversary of this course which has grown in popularity and the GSB to over 50 students.??

December 31st of 2020, Sergio finally finished his board responsibilities at Norwest and on January 1st 2021, he founded Roble Ventures as a solo GP. As the founding GP of Roble Ventures, he is focused on supporting under-represented founders in the “future of work.” He named his fund Roble because it was the name of his dorm at Stanford and because it’s the Spanish name for Oak - a tree that can weather any storm. Roble Ventures now has 3 active employees and over 17 investments.

When asked if he outgrew imposter syndrome, Sergio says that he doesn’t think anybody ever outgrows imposter syndrome if you continue to try new challenging endeavors. In fact, Sergio credits this imposter syndrome as the source of his motivation and success. It is his motivation to show people that the kid who came across the border with very few resources, no language skills and little social capital can build success in a foreign place like America if they works hard and help other people succeed. As of today, Sergio spends a lot of his time mentoring new entrepreneurs and VCs who remind him of his younger self.?His largest source of pride now is helping those new founders go the distance.