Jess Li
Jess Li
May 23 · 4 min read
Nick Friedman

I spoke with Nick Friedman, co-founder of Board (YC W19), a new type of mortgage company recreating the future of homeownership. Board upgrades any offer to a cash offer and provides greater access and transparency for both sellers and buyers throughout the home purchase experience.

Nick and I discussed advice for founders, his own journey, the importance of people and communities, and the Y Combinator experience.

Never get married to a single idea. One of the biggest mistakes founders can make is building a product in isolation, providing a solution that does not meet the market’s need or desires. Always speak with your target customers and be ready to continuously iterate on everything from your UX and platform to your approach to your underlying technology. Finding product market fit is both an interactive and repetitive process. For Nick, especially in the beginning, he and his team were ruthless in refining their model. They would often “disrupt” themselves hours, days, or even months after coming up with a new idea. The longer the interval, the harder it was to switch to the better idea. It took nearly two years of iterations, failures, and moving all over the country to finally land on Board as it stands today. Nick stressed how different of a company they would be if they would have gotten complacent too early on.

Go to the people at the top. Strive to speak with decision makers at companies in the ecosystem for customer or partnership research. If you are working with a regulatory framework, speak with the person who created the regulation. Learning from these experts brings you to the source of the problem of interest and closer to the ideal solution. Through these conversations, you develop tremendously more valuable understandings of the landscape and are much more able to refine your strategy ahead. Nick and his co-founder Adam are known amongst their investors, friends, and team to never be shy about this. Cold calling everyone from executives at Fannie Mae to celebrities on Million Dollar Listing, they became experts at talking to “strangers.” Combined, Nick and Adam called about 2,000 bank CEOs one week in an attempt to find a banking partner.

Use your student network. Even for entrepreneurs, the university alumni network can be invaluable. And never be afraid to reach out to the most senior people — frequently others feel the same way and as a result, these leaders actually receive limited outreach from students and may in fact be quite willing to engage and mentor.

Take advantage of unconventional challenges and opportunities. Entrepreneurial tendencies are frequently found through the most seemingly unlikely pursuits. For Nick, in elementary and middle school, he had actually been quite introverted. But later events, such as a devastating sports injury, led him to try new, out of the box activities. This included beatboxing that was, at first, quite outside of his comfort zone but later proved very much in his wheelhouse and quite formative to his development as an entrepreneur. Through beatboxing, Nick began to perform, give speeches, and do TedX talks. These platforms gave Nick a newfound confidence that he took with him into college and ultimately drove his decision to drop out and pursue Board.

Find the right people. When in college at Williams, he met his best friend who later became his co-founder at Board. Together, they truly felt they could solve any challenge. Nick stressed the importance of finding complementary, smart, and incredible people as they (rather than any underlying venture idea) truly make the entrepreneurship experience.

Later in their Y Combinator interview and final acceptance, Nick recalls that the uniqueness of their team was truly what stood out as a main differentiator.

Y Combinator — “the best form of peer pressure you can ever have.” At Y Combinator, you are placed in a community of some of the most motivated and talented people of all time. Hearing their updates each week and feeling their drive as founders truly drives you to work harder and reach new heights each day. Ultimately, Y Combinator represented a mindset change rather than some list of facts learned. The takeaway was in the people and the novel way of thinking the community brought about. One of the coolest parts about Y Combinator for Nick was the weekly dinner speakers. Getting a raw look into some of the most successful companies to come out of Y Combinator was invaluable. Nick and his team are going through a lot of the same challenges that large and successful companies are still going through today. There is no “formula” to running a business, but rather a multitude of experiences that founders can share and draw from to help them adapt to their crazy lifestyles and the new situations that they face every day. This community of entrepreneurs is something Nick and his team will have forever.

Profiles In Entrepreneurship — PIE

An intercollegiate publication that feature advice and stories from the brightest figures in entrepreneurship.

Jess Li

Written by

Jess Li

Harvard 2019 | Head of Content @ Elpha & Harvard in Tech | Early Stage VC @ Soma Capital | Pilates Enthusiast & Runner

Profiles In Entrepreneurship — PIE

An intercollegiate publication that feature advice and stories from the brightest figures in entrepreneurship.

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