The motivation to start a company wasn't about a guaranteed outcome but about embracing the ultimate test of one's capabilities. The realization that most founders, regardless of experience, are figuring it out as they go is empowering. It reframes the founder journey from a path for experts to a challenge for the determined.
The 'Grit' podcast wasn't created for general brand building. It was a targeted solution to a specific problem: Kleiner Perkins needing to identify and build relationships with the best CROs for their portfolio companies. This reframes content creation from a marketing activity to a strategic, problem-solving mechanism.
To land a role at his target company, which repeatedly said he was too inexperienced, Jubin secured 16 other job offers. He then sent each offer letter to the hiring manager as proof of his value, a persistent and unconventional strategy that ultimately succeeded in getting him hired.
Instead of relying on ad-hoc calls to finance or other reps, LLMs can act as a central nervous system for sales. By analyzing past quotes and data, AI can instantly recommend the optimal deal structure for a new quote—maximizing commission for the rep and aligning with business goals, putting revenue back in motion.
Most VCs fail at talent support by simply matching logos on a resume to a portfolio company. A better model is to first embed operators (e.g., fractional sales leaders) into the startup. This provides the deep, nuanced context required to find candidates who fit the specific business and culture, leading to better hiring outcomes.
The most effective operators, dubbed 'dolphins,' can fluidly move between altitudes: operating strategically at 10,000 feet with founders, managing at 5,000 feet, and executing tactically in the weeds at 1,000 feet. This ability to oscillate is a key trait to hire for, especially in advisory or early-stage leadership roles.
Jubin attributes his dual-sided personality—taking some things very seriously and others not at all—to his childhood spent between two households. His mother instilled hardcore discipline, while his father taught him irreverence. This combination of structure and willingness to challenge norms created a unique and effective leadership style.
By establishing a standing weekly reservation at a highly sought-after Chicago steakhouse, Jubin created a powerful networking asset. Senior leaders who couldn't otherwise get a table would ask to use his reservation for client meetings, giving him invaluable access and relationship-building opportunities far above his station.
Grit isn't just about perseverance through hardship. It's the ability to do something consistently over a long period. Jubin argues this is only possible when the work itself gives you energy and you genuinely enjoy it. This insight connects passion directly to resilience, suggesting you should align your career with your energy sources.