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Hello Reader,
One of the challenges in venture capital is that the best decisions must be made before there is enough information to be certain.
Founders make decisions without knowing exactly how a market will evolve. Investors make decisions before a company has proven itself. Limited partners make decisions before a fund has produced results.
This week on The Sure Shot Entrepreneur, Justin Smith-Lorenzetti shares how he thinks about conviction, founder quality, and long-term relationships in venture investing. One of the ideas that stood out to me is that the strongest founder-investor relationships often begin long before a fundraising round.
We also revisit a conversation with Vivek Krishnamurthy on building relationships before you need capital
Upcoming Events:
July 30, Webinar: Founders Network: Pitch Practice
– Gopi Rangan, Host of the The Sure Shot Entrepreneur podcast
Startup Corner: Coterie
One trend catching the attention of insurers is the rapid growth of side businesses and gig work.
According to Coterie Insurance CEO David McFarland, nearly one-third of U.S. households now operate some form of side business, creating a large and growing market of entrepreneurs who need commercial insurance but are often underserved by traditional providers.
Coterie was built to serve this segment. The company uses technology to make it easier for small businesses, independent professionals, and micro-business owners to access commercial insurance through a streamlined digital experience and distribution network.
As more people turn entrepreneurial, whether through side hustles, freelancing, or small business ownership, the demand for simple, accessible business insurance is expected to grow. Coterie is positioning itself at the center of that trend, which helps explain why the company stood out to Justin Smith-Lorenzetti and Intact Private Capital as an investment opportunity.
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New Podcast: Have desire to build with unwavering commitment
In Episode 191, my guest was Justin Smith-Lorenzetti, Founder and Managing Director at Intact Private Capital. Justin shares lessons from investing in companies such as Turo, Coterie, and Shepherd. He explains why conviction matters more than checklists, how founder-investor relationships are built long before fundraising begins, and why focus is becoming an increasingly important competitive advantage in an AI-driven world.
Key Takeaways
- Great founders create conviction through their intensity, ambition, and determination.
- Founder-investor relationships are strongest when they develop before a financing round.
- Focus and discipline are becoming more valuable as AI increases the pace of change.
- The best investors identify exceptional people rather than simply evaluating markets.
- Respecting incumbents often leads to better startup opportunities than assuming disruption is easy.
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Connected Insights: Build Relationships Before You Need Capital
Vivek Krishnamurthy, my guest in Episode 34, discussed the importance of engaging investors before a fundraise so that conversations are grounded in trust, understanding, and shared context rather than immediate transactions.
Strong founder-investor partnerships are often built through many small interactions over time. By the time a financing discussion begins, both sides already understand how the other thinks and operates.
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Community Involvement: The Barry F. Lorenzetti Foundation
Justin is passionate about the work of The Barry F. Lorenzetti Foundation, which supports initiatives focused on mental health, healthcare, education, and community development.
The foundation reflects a commitment to creating long-term impact beyond business and investing, helping strengthen communities through philanthropy and social engagement.
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