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Investing in Student-Led Startups with Founder’s Cupid

Jun 8, 2023

Sydecar and Bobby Housel

In 2021, Bobby Housel was returning to the University of Michigan following a gap year and was anxious to catch up with the founder friends he had made at school. Fueled by this excitement, he started hosting small gatherings of his closest founder friends. Quickly, he observed that  these entrepreneurs were a lot more interested in meeting each other than catching up with Bobby. 

What became clear was that college entrepreneurial programming was failing in two primary ways. Firstly, it was failing to connect the top college founders with one another. At a large school like Michigan there are more than ten different entrepreneurial communities for students. Beyond that, they are massive, lumbering institutions shrouded in red tape and forced to cater to the “average” entrepreneur. This means the top 10% of founders find themselves ignored by most college entrepreneurial programming.

As Bobby held more of these meetups, it became clear there was an opportunity to build a better community for top college entrepreneurs. He soon teamed up with Barry Sabin to launch Founder’s Cupid, a community to help tell founders’ stories through strategic media partnerships, introduce them to their first hires, and provide other support.  

What started as a community focused on connecting like-minded founders has quickly evolved into much more. They now reach three university ecosystems and over 350 founders. From telling founders’ stories through strategic media partnerships to introducing them to their first hires, Founder’s Cupid does whatever it takes to support the top college founders. In addition to providing education and community, Founder’s Cupid launched a syndicate in 2023 to connect pre-seed and seed founders with capital and mentorship. Their first two investments in Ultima Insights, a fintech AI company for investment research, and Fundwurx, a corporate social responsibility company for SMBs, are set to close in June. 

More than Just Consumer Startups

Housel and Sabin believe that colleges across the US are letting value slip through the cracks when it comes to student founders. Common beliefs about this population – from the lack of experience and perspective to the belief that student founders exclusively build simplistic consumer companies – result in this population not being taken seriously. 

But these dated biases are an opportunity for open-minded investors. College students are gaining work experience earlier, sometimes leaving high school with 1-2 internships already under their belt. Students can develop industry expertise through internships, cutting-edge knowledge through university research, and the fresh eyes needed to rethink a stagnant industry. Investors who recognize these shifts will find themselves ripe with opportunity to invest into promising student-founded companies .

Student Founder Communities Must Be Flexible by Default

Balancing schoolwork, extracurriculars, and company building is an extraordinary challenge for student founders. The support that comes from joining a founder community is valuable, so long as membership is flexible and doesn’t become an additional obligation.

Founder’s Cupid has built its community upon radical openness and activities that are opt-in. In letting founders choose when they engage in the community, the community never becomes a burden. Student founders are busy individuals. A required commitment to a community is counterproductive to their startup’s success. 

In connecting students with alumni investors, Founder’s Cupid seeks out investors that have the skillsets and willingness to help in a concrete way. Intelligent matchmaking is key to ensuring that no one’s time is wasted. Founder’s Cupid focuses on delivering value in every match  by seeking out alumni investors that both want to be involved with their alma mater and have conviction in the school’s talent pool.

Betting on Student Founders for the Long Run

Students can be some of the most motivated and visionary founders. But they have different challenges to navigate, from discouraging parents, demanding classes, and the general distractions that come with  the college experience. Investors working with student founders should understand the unique challenges that they face so that they can provide better, tailored support.

Student founders are often stretched in a million directions. While top student founders are wizards of time management and optimization, they typically don’t operate like other founders. Their work on their startup may be concentrated on weekends and evenings, or they may have to ease up on their speed of execution during finals week. 

Student founders are more likely to pivot as they refine their personal mission and gain knowledge from their studies. But, even if their first idea doesn’t find product market fit, the entrepreneurial itch often found within student founders will likely lead them to another exciting idea before too long.  From an investor’s perspective, supporting a young founder early in their journey can pay dividends. Rest assured that they will come back to the investor with opportunities for years. Some investors describe this as “tagging founders” -- investing money super early as a way to keep tabs on them for years to come. 

Investors can expect to be more hands-on with student founders than they might be with more experienced company builders. Investors who demonstrate an ability to help and advocate for student founders, not only further win their trust, but can supercharge their growth. 

Knowing these differences will help you navigate the promising pool of student-founded startups. Startup investing is already a wild experience. Investing in student startups will make the entire process more wild and rewarding in every way. 

In 2021, Bobby Housel was returning to the University of Michigan following a gap year and was anxious to catch up with the founder friends he had made at school. Fueled by this excitement, he started hosting small gatherings of his closest founder friends. Quickly, he observed that  these entrepreneurs were a lot more interested in meeting each other than catching up with Bobby. 

What became clear was that college entrepreneurial programming was failing in two primary ways. Firstly, it was failing to connect the top college founders with one another. At a large school like Michigan there are more than ten different entrepreneurial communities for students. Beyond that, they are massive, lumbering institutions shrouded in red tape and forced to cater to the “average” entrepreneur. This means the top 10% of founders find themselves ignored by most college entrepreneurial programming.

As Bobby held more of these meetups, it became clear there was an opportunity to build a better community for top college entrepreneurs. He soon teamed up with Barry Sabin to launch Founder’s Cupid, a community to help tell founders’ stories through strategic media partnerships, introduce them to their first hires, and provide other support.  

What started as a community focused on connecting like-minded founders has quickly evolved into much more. They now reach three university ecosystems and over 350 founders. From telling founders’ stories through strategic media partnerships to introducing them to their first hires, Founder’s Cupid does whatever it takes to support the top college founders. In addition to providing education and community, Founder’s Cupid launched a syndicate in 2023 to connect pre-seed and seed founders with capital and mentorship. Their first two investments in Ultima Insights, a fintech AI company for investment research, and Fundwurx, a corporate social responsibility company for SMBs, are set to close in June. 

More than Just Consumer Startups

Housel and Sabin believe that colleges across the US are letting value slip through the cracks when it comes to student founders. Common beliefs about this population – from the lack of experience and perspective to the belief that student founders exclusively build simplistic consumer companies – result in this population not being taken seriously. 

But these dated biases are an opportunity for open-minded investors. College students are gaining work experience earlier, sometimes leaving high school with 1-2 internships already under their belt. Students can develop industry expertise through internships, cutting-edge knowledge through university research, and the fresh eyes needed to rethink a stagnant industry. Investors who recognize these shifts will find themselves ripe with opportunity to invest into promising student-founded companies .

Student Founder Communities Must Be Flexible by Default

Balancing schoolwork, extracurriculars, and company building is an extraordinary challenge for student founders. The support that comes from joining a founder community is valuable, so long as membership is flexible and doesn’t become an additional obligation.

Founder’s Cupid has built its community upon radical openness and activities that are opt-in. In letting founders choose when they engage in the community, the community never becomes a burden. Student founders are busy individuals. A required commitment to a community is counterproductive to their startup’s success. 

In connecting students with alumni investors, Founder’s Cupid seeks out investors that have the skillsets and willingness to help in a concrete way. Intelligent matchmaking is key to ensuring that no one’s time is wasted. Founder’s Cupid focuses on delivering value in every match  by seeking out alumni investors that both want to be involved with their alma mater and have conviction in the school’s talent pool.

Betting on Student Founders for the Long Run

Students can be some of the most motivated and visionary founders. But they have different challenges to navigate, from discouraging parents, demanding classes, and the general distractions that come with  the college experience. Investors working with student founders should understand the unique challenges that they face so that they can provide better, tailored support.

Student founders are often stretched in a million directions. While top student founders are wizards of time management and optimization, they typically don’t operate like other founders. Their work on their startup may be concentrated on weekends and evenings, or they may have to ease up on their speed of execution during finals week. 

Student founders are more likely to pivot as they refine their personal mission and gain knowledge from their studies. But, even if their first idea doesn’t find product market fit, the entrepreneurial itch often found within student founders will likely lead them to another exciting idea before too long.  From an investor’s perspective, supporting a young founder early in their journey can pay dividends. Rest assured that they will come back to the investor with opportunities for years. Some investors describe this as “tagging founders” -- investing money super early as a way to keep tabs on them for years to come. 

Investors can expect to be more hands-on with student founders than they might be with more experienced company builders. Investors who demonstrate an ability to help and advocate for student founders, not only further win their trust, but can supercharge their growth. 

Knowing these differences will help you navigate the promising pool of student-founded startups. Startup investing is already a wild experience. Investing in student startups will make the entire process more wild and rewarding in every way. 

In 2021, Bobby Housel was returning to the University of Michigan following a gap year and was anxious to catch up with the founder friends he had made at school. Fueled by this excitement, he started hosting small gatherings of his closest founder friends. Quickly, he observed that  these entrepreneurs were a lot more interested in meeting each other than catching up with Bobby. 

What became clear was that college entrepreneurial programming was failing in two primary ways. Firstly, it was failing to connect the top college founders with one another. At a large school like Michigan there are more than ten different entrepreneurial communities for students. Beyond that, they are massive, lumbering institutions shrouded in red tape and forced to cater to the “average” entrepreneur. This means the top 10% of founders find themselves ignored by most college entrepreneurial programming.

As Bobby held more of these meetups, it became clear there was an opportunity to build a better community for top college entrepreneurs. He soon teamed up with Barry Sabin to launch Founder’s Cupid, a community to help tell founders’ stories through strategic media partnerships, introduce them to their first hires, and provide other support.  

What started as a community focused on connecting like-minded founders has quickly evolved into much more. They now reach three university ecosystems and over 350 founders. From telling founders’ stories through strategic media partnerships to introducing them to their first hires, Founder’s Cupid does whatever it takes to support the top college founders. In addition to providing education and community, Founder’s Cupid launched a syndicate in 2023 to connect pre-seed and seed founders with capital and mentorship. Their first two investments in Ultima Insights, a fintech AI company for investment research, and Fundwurx, a corporate social responsibility company for SMBs, are set to close in June. 

More than Just Consumer Startups

Housel and Sabin believe that colleges across the US are letting value slip through the cracks when it comes to student founders. Common beliefs about this population – from the lack of experience and perspective to the belief that student founders exclusively build simplistic consumer companies – result in this population not being taken seriously. 

But these dated biases are an opportunity for open-minded investors. College students are gaining work experience earlier, sometimes leaving high school with 1-2 internships already under their belt. Students can develop industry expertise through internships, cutting-edge knowledge through university research, and the fresh eyes needed to rethink a stagnant industry. Investors who recognize these shifts will find themselves ripe with opportunity to invest into promising student-founded companies .

Student Founder Communities Must Be Flexible by Default

Balancing schoolwork, extracurriculars, and company building is an extraordinary challenge for student founders. The support that comes from joining a founder community is valuable, so long as membership is flexible and doesn’t become an additional obligation.

Founder’s Cupid has built its community upon radical openness and activities that are opt-in. In letting founders choose when they engage in the community, the community never becomes a burden. Student founders are busy individuals. A required commitment to a community is counterproductive to their startup’s success. 

In connecting students with alumni investors, Founder’s Cupid seeks out investors that have the skillsets and willingness to help in a concrete way. Intelligent matchmaking is key to ensuring that no one’s time is wasted. Founder’s Cupid focuses on delivering value in every match  by seeking out alumni investors that both want to be involved with their alma mater and have conviction in the school’s talent pool.

Betting on Student Founders for the Long Run

Students can be some of the most motivated and visionary founders. But they have different challenges to navigate, from discouraging parents, demanding classes, and the general distractions that come with  the college experience. Investors working with student founders should understand the unique challenges that they face so that they can provide better, tailored support.

Student founders are often stretched in a million directions. While top student founders are wizards of time management and optimization, they typically don’t operate like other founders. Their work on their startup may be concentrated on weekends and evenings, or they may have to ease up on their speed of execution during finals week. 

Student founders are more likely to pivot as they refine their personal mission and gain knowledge from their studies. But, even if their first idea doesn’t find product market fit, the entrepreneurial itch often found within student founders will likely lead them to another exciting idea before too long.  From an investor’s perspective, supporting a young founder early in their journey can pay dividends. Rest assured that they will come back to the investor with opportunities for years. Some investors describe this as “tagging founders” -- investing money super early as a way to keep tabs on them for years to come. 

Investors can expect to be more hands-on with student founders than they might be with more experienced company builders. Investors who demonstrate an ability to help and advocate for student founders, not only further win their trust, but can supercharge their growth. 

Knowing these differences will help you navigate the promising pool of student-founded startups. Startup investing is already a wild experience. Investing in student startups will make the entire process more wild and rewarding in every way.