profile

Sure Shot Entrepreneur Newsletter

Practical VC, Upfront, Juno: The Sure Shot Entrepreneur Newsletter

Published about 2 months ago • 2 min read

Hello Reader,

Startup investments are taking longer to pay off. Founders, early investors, and employees want liquidity sooner. That's why secondary markets are booming! I truly believe this is a crucial structure for our ecosystem to stay healthy. I recently chatted with Aman Verjee from Practical VC, a Silicon Valley veteran who offers some fantastic insights on this trend. We also dove into the evolution of the startup world since the 1990s, all the way to the big question today: are we in a bubble? Aman says absolutely not! Tune in to the new podcast episode to hear our full conversation.

Last week, Oren Zeev and I had a fun fireside chat at an event organized by the Consulate Generals of India and Israel. We chatted about his awesome investments, current trends in artificial intelligence, and his super helpful advice to founders.

I'll be in sunny Los Angeles on Feb 24 and 25! If you're heading to the Upfront Summit, I'd absolutely love to connect. Let's grab a coffee!

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

Startup Corner: Juno

​Juno, the child disability insurance innovator, continues its strong momentum. In its first year since launch, nearly 100 leading employers have adopted Juno’s solutions to support working families and expand inclusive benefits. This rapid adoption highlights a growing recognition of disability insurance as essential workplace coverage, especially in an era where traditional benefits often fall short. As employers seek benefits that reinforce retention, equity, and long-term wellbeing, Juno’s early traction signals broad demand for innovative, human-centered insurance products.

New Podcast: Are we in a Bubble of Bubble Talk?

​Aman Verjee, General Partner at Practical Venture Capital was my guest in Episode 182. Aman explains why today’s venture ecosystem looks fundamentally different from the one many investors were trained in. Companies are staying private longer. Capital cycles are extended. Liquidity is delayed.

In that environment, secondaries are no longer niche. They are structural. They help align incentives, provide liquidity to early stakeholders, and reduce pressure on companies forced to wait years longer for traditional exits.

Aman’s broader point: we’re not just in a market cycle we’re in a structural evolution. Venture timelines have stretched, and the mechanics of liquidity have had to evolve alongside them.

That evolution changes more than portfolios. It changes how companies must be built.

Connected Insights: Endurance Is the New Alpha

If liquidity takes longer and companies stay private longer, then founder behavior must adjust.

​In Episode 83, my guest was Mark Suster from Upfront Ventures. Mark emphasized three traits that now feel even more essential:

  • Relationship-building before fundraising
  • Hiring deliberately, not reactively
  • Capital discipline from day one

When exits may take a decade, investor relationships must be built on trust and not just transactions, hiring velocity must match sustainable growth, and burn rate must assume capital won’t always be cheap.

As venture evolves structurally, founders who build for endurance — not optics — will define the next generation of winners.

Community Involvement: AYSO (American Youth Soccer Organization)

Outside of venture capital, Aman Verjee is passionate about the American Youth Soccer Organization (AYSO), a nonprofit dedicated to youth development through soccer. AYSO’s mission centers on inclusivity, teamwork, and personal growth by providing structured, supportive soccer experiences for children of all backgrounds. Aman believes that play and community engagement build resilience and character long before entrepreneurial journeys ever begin.

Have questions or feedback? Reply to this message and we will get back to you

This message is sent to Reader from: 616 Ramona St, Suite 20, Palo Alto, CA 94301
​
​Unsubscribe · Preferences​

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

Read more from Sure Shot Entrepreneur Newsletter

Hello Reader, My career journey is rooted in the exhilarating world of deep-tech—think semiconductors, algorithms, and those fundamental breakthroughs that literally built Silicon Valley! For years, deep-tech was venture capital, defining the industry and my path alongside it. While the startup scene has since exploded into everything from consumer apps to finance, deep-tech is back in the spotlight, driving the next wave of disruptive ideas. Want the inside scoop? I'm excited to feature...

4 days ago • 3 min read

Hello Reader, "Go to school, work hard, follow the rules." That was the path to success for many immigrant and middle-class families. But sometimes, an idea is so big, so timely, that you just have to drop everything and chase it, even college. This idea challenges the core values I grew up with and still hold as a faculty teaching at INSEAD, but I get it: sometimes you have to break the rules. That's where 1517 Fund comes in. It is a VC firm that exclusively backs entrepreneurs as early as...

18 days ago • 3 min read

Hello Reader, Sure Ventures primarily invests in the pre-seed and seed stages. We recently attended a conference for emerging manager VCs where Peter Walker, Head of Insights at Carta, shared a comprehensive analysis of industry trends. His presentation, which draws on approximately 500,000 transactions recorded since 2018, offers valuable insights into the current challenges and opportunities in venture capital. You can view the presentation here. Upcoming Event: I will be speaking to...

about 1 month ago • 2 min read