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Sure Shot Entrepreneur Newsletter

Spero, Marathon Management Partners, Coterie: The Sure Shot Entrepreneur Newsletter

Published 19 days ago • 2 min read

Hello Reader,

The venture capital landscape is constantly changing. New talent joins the ecosystem at junior levels, developing their skills over time. Experienced leaders transition from successful careers into senior VC roles or launch their own firms. For me, launching Sure Ventures meant stepping away from lucrative, prestigious roles mid-career. It has been incredibly rewarding and, truly, the best job in the world.

This week, I'm highlighting two different perspectives on the industry. The new podcast episode features a conversation with Stephen Wemple, a young venture capital investor about his journey. Additionally, in the connected insights section, I revisit a past episode with Gokul Rajaram, a phenomenal leader, someone I admire, who recently founded the new venture capital firm, Marathon Management Partners.

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

Startup Corner: Coterie

​Coterie Insurance continues its momentum as one of the most innovative players in small business insurance. The company recently announced a strategic investment from Allianz X, strengthening its mission to make commercial coverage instant, accurate, and accessible for the 33 million small businesses across the U.S.

Coterie’s platform simplifies one of the most outdated parts of the insurance value chain: quoting and binding small business policies. By connecting trusted data sources and automating underwriting, Coterie allows agents, digital platforms, and partners to bind policies in minutes, not days.

Allianz X’s investment signals strong confidence in Coterie’s data-driven approach and scalable model. As small businesses seek modern, flexible coverage, Coterie is positioning itself as the infrastructure powering the next generation of commercial insurance.

New Podcast: Show Commitment to the Mission

My guest in episode 178 is Stephen Wemple, Principal at Spero Ventures. Stephen shares how an unexpected path—from a Fulbright year in Vietnam to early work in emerging markets—shaped his belief in entrepreneurship as a powerful force for impact. At Spero, he focuses on mission-driven founders and explains why everything in early-stage venture ultimately comes down to founder quality and authentic commitment to the problem.

Stephen describes how Spero evaluates early signals of product-market fit, why purpose-led teams often outperform, and how junior investors inside a VC firm can be invaluable partners during a fundraise. He also offers candid advice on first meetings: paint a clear picture of the future you’re building, show why the problem is inevitable, and let your conviction shine through.

Connected Insights: The Power of Early Believers

Gokul Rajaram was one of the earliest guests on The Sure Shot Entrepreneur podcast, and few embody the notion of an “early believer” the way he does. In episode #2, Gokul breaks down what it means to support founders at the very beginning: long before the metrics are impressive; long before market validation; and long before certainty exists.

Gokul emphasizes a theme that strongly echoes through my conversations with other guests on the podcast, including Stephen Wemple: great companies start with great partners. These are people who help founders clarify their thinking, pressure-test assumptions, and build discipline early.

AchieveKids

During my conversation with Stephen Wemple, I had the chance to reflect on my own involvement with AchieveKids, a nonprofit organization close to my heart and where I’ve served on the board for more than a decade. AchieveKids serves students with complex emotional and developmental needs, providing individualized education, mental health services, and life-skills training for children and young adults aged 5–22.

The organization partners with school districts to ensure that no student is left behind simply because traditional systems aren’t equipped to support them. AchieveKids’ mission is rooted in dignity, inclusion, and empowerment. These values resonate strongly with the spirit of entrepreneurship and long-term impact we discuss on the podcast.

Supporting AchieveKids is a reminder that innovation takes many forms, and some of the most meaningful happen outside the venture ecosystem, in classrooms and communities where the need is greatest.

​

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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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