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Sure Shot Entrepreneur Newsletter

Boost VC, Trinity Ventures, Joshu: The Sure Shot Entrepreneur Newsletter

Published 21 days ago • 2 min read

Hello Reader,

A career in venture capital might seem like a given for someone from a family with three generations of VCs. However, unlike many other fields, the venture capital landscape is remarkably level. Attracting top-tier founders and making early, successful bets on unproven ideas doesn't rely on legacy. Anyone with enough grit and business savvy has a real shot at building a successful VC firm, a truth that holds as much now as it did in the beginning.

William Draper, a Silicon Valley VC pioneer and a protégé of George Doriot, often called the father of venture capital, certainly established a distinguished legacy. His grandson, Adam Draper, is my latest podcast guest. Adam is now charting his own distinct course in the world of venture capital, following in his grandfather's footsteps.

– Gopi Rangan, Host of the The Sure Shot Entrepreneur podcast

Startup Corner: Joshu

Digital insurance is evolving fast. In a recent partnership announcement, Joshu joined forces with Herald to enable insurers and MGAs to launch and distribute digital insurance products faster than ever.

The integration allows Joshu’s no-code underwriting and distribution platform to connect to Herald’s multi-carrier API network, cutting time-to-market significantly and giving smaller carriers access to broader digital channels. In a crowded marketplace, speed, flexibility and execution become the edge, not just the idea.

New Podcast: Be the Quirky Underdog Building the Next New Thing

My guest in The Sure Shot entrepreneur podcast episode 176 is Adam Draper, a fourth-generation Silicon Valley venture investor who leads Boost VC and focuses on pre-seed, frontier tech, crypto, and deep-tech. He reflects on his family’s legacy in shaping venture capital and explains how his firm seeks “endeavors of consequence” where the boldest path can become the safest. Adam also explains how he evaluates “weird founder type” entrepreneurs. These are founders with high agency, obsession, and curiosity. Adam explains why he makes bets few others are willing to make. He argues that true advantage comes from being contrarian, nimble, and curious in a world chasing consensus.

Connected Insights: Successful Founders Are Naive Fast Learners

In Episode #88, Schwark Satyavolu, General Partner at Trinity Ventures was my guest. Schwark distills what he looks for in early-stage founders into two powerful traits: naivety and rapid learning. He argues that naivety means believing you can change the world even if you don’t yet know how. Fast learning means picking up everything that’s knowable about your focus area and doing it fast enough to out-learn competition.

He’s clear:

“If you’re naive but not a fast learner, that will be a disaster. If you’re a fast learner but not naive, you’re not ambitious enough.”

For founders, the message is simple yet profound: Don’t interrogate whether you can win. Investigate whether you can learn fast enough to change the game. Your edge comes from being the newcomer who learns smarter, adapts quicker, and outpaces the rest.

Community Involvement: The Ocean Cleanup

Adam Draper is proud of his support for The Ocean Cleanup, a non-profit engineering organisation aiming to rid the world’s oceans of plastic waste through tech-driven solutions. Founded in 2013, The Ocean Cleanup has developed systems to both intercept litter in rivers (which account for ~80% of plastic entering oceans) and extract legacy plastic from ocean gyres. Their goal is to remove 90% of floating ocean plastic by 2040.

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Sure Shot Entrepreneur Newsletter

Gopi Rangan

Enable Peace of Mind for all. We believe in mission-driven entrepreneurs at the earliest stages before the rest of the world realizes the impact of their visionary ideas. This newsletter pairs well with our podcast that shares all the funders and founders' knowledge to startup and scale your ideas. All the best, Gopi

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