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Sure Shot Entrepreneur Newsletter

Practical Venture Capital, Upekkha, Lumber: The Sure Shot Entrepreneur Newsletter

Published about 2 months ago • 2 min read

Hello Reader,

Ever wondered what happens when an early-stage VC spills the beans? Well, wonder no more! I recently sat down with the insightful Patrick Mork on his new podcast show, "Mork Unfiltered." We dove deep into my experiences with over 100 founders, covering everything from my own missteps in venture capital to actionable tips for founders to get the most out of working with VCs like me. Get ready for some honest reflections, hard-earned lessons, and a few personal stories that might just surprise you. Tune in to our candid conversation here!​

And speaking of influential voices, on The Sure Shot Entrepreneur podcast, I had the pleasure of chatting with none other than Silicon Valley legend Dave McClure! He's a true pioneer in the VC secondaries market, a segment that's become a cornerstone of our vibrant ecosystem. You won't want to miss his insights!

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

Startup Corner: Lumber

​Lumber, an AI-powered workforce management platform for the construction industry, is addressing one of the industry’s biggest problems—labor inefficiency, which costs the U.S. economy $30–40 billion a year.

In its recent acquisition of BuilderFax, Lumber introduced digital credentialing to simplify how contractors validate labor skills. Workers can now manage their credentials via a free wallet, and project leads can verify them instantly. Combined with Lumber’s AI-driven payroll, time-tracking, and gamification tools, this solution brings transparency and productivity to every job site.

Lumber isn’t just optimizing workflows. It’s making the construction workforce smarter, faster, and more empowered.

Podcast Entries:

Secondaries are Essential for the Venture Capital Market

​My guest in episode 169 is Dave McClure, founder of Practical Venture Capital and co-founder of 500 Startups. With decades of experience in the venture capital industry, Dave shares a fresh perspective on why secondary transactions have become a critical component of today’s venture ecosystem.

He explains how extended liquidity timelines, delayed IPOs, and investor fatigue are increasing the relevance of secondaries. Dave breaks down different types of deals (GP-led, direct company-level) and what he looks for in investments: companies with $50–100 million in revenue and a clear path to exit in 3 to 5 years. He also warns against overhyped valuations and emphasizes the importance of disciplined deal-making.

🎧 Get Dave’s perspective on how secondaries are reshaping venture capital.

Connected Insights:

Take Advice from the Right People at the Right Time

​In episode 150, my guest was Rajan Maruthavanan of Upekkha. Rajan offers a complementary perspective on alternative exit strategies. With over 120 pre-seed SaaS investments under his belt, Rajan shares how he supports founders through M&A by emphasizing stakeholder alignment, strategic timing, and peer-informed decision-making, rather than reactive moves.

While Dave McClure, in episode 169, underscores the growing role of secondary share sales, continuation funds, and creative deal structures in a world of extended liquidity timelines, Rajan brings the founder’s lens, emphasizing operational nuance and timing.

Together, these episodes present a candid, multi-layered look at how venture capital players can navigate and shape modern liquidity paths.

Community Involvement: New Story Homes

Outside of venture capital, Dave McClure champions New Story Homes, a nonprofit dedicated to solving the global housing crisis. The organization builds 3D-printed homes for communities in Latin America, using modern technology and radical transparency.

Dave admires how New Story approaches housing the same way startups tackle software problems by building scalable, data-informed, and human-centered solutions. With 100% of donations going directly to construction, New Story has already helped more than 14,000 people find safe, permanent homes.

Their work is a powerful example of how innovation and empathy can meet real-world needs.

​

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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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