USVP, Upfront, Insurate: The Sure Shot Entrepreneur Newsletter


Hello Reader,

Today’s startups can reach customers anywhere in the world. But with AI and rapid tech adoption leveling the playing field, “technology advantage” has become an illusion. The real battleground is execution.

Execution means ruthless focus on your niche, your target market, and nailing product–market fit. Yet the biggest threats to that focus aren’t always obvious. In a new podcast episode, my guest Jacques reveals how flattering inbound interest can quietly derail your market entry strategy.

In a previous conversation with Mark Suster, we explored another hidden edge: deep, intentional relationship-building with investors. Founders who take the time to explain their value proposition and market dynamics earn more than funding. They build the trust they’ll need when the pressure’s on.

I am also excited to share a new program I plan to launch for founders in the INSEAD community: Doriot’s Disruptors. Here is the link to apply to the program. Please share with founders in the INSEAD community. Interested entrepreneurs are welcome to join one of the information webinars on Aug 12 at 5 pm PT or Aug 14, 9 am PT.

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

Startup Corner: Insurate

Insurate is revolutionizing workers' comp insurance by using AI and data to reward safety. In a space often burdened by outdated actuarial models, Insurate’s Propensity Safety Score™ provides a forward-looking measure of risk, helping safe businesses get the premiums they deserve.

A new partnership with Markel Insurance brings this tech-driven underwriting approach to even more employers, reducing costs and improving outcomes for frontline industries like construction, manufacturing, and transportation.

With a simple premise—“the safer you are, the less you pay”—Insurate is bringing fairness and insight to commercial insurance.

Podcast Entries: Your Biggest Danger Is an Inbound

My guest in episode 171 is Jacques Benkoski, General Partner at U.S. Venture Partners. Jacques, a seasoned VC with a background as a CEO and operator, challenges startup myths and highlights how focus, not speed, leads to lasting category leadership.

Drawing on decades of experience, Jacques unpacks the noise of today’s venture ecosystem and shares a structured framework for market entry that rejects randomness. He illustrates this with an example: a cybersecurity startup that won by zeroing in on medical devices (a high-value, focused niche) rather than casting a wide net.

Jacques also opens up about the psychological toll of entrepreneurship, reminding founders that what they need most isn’t just capital but a thought partner; someone who helps them reflect, regroup, and keep perspective.

Connected Insights: Build genuine relationships with venture capital investors

In episode 83, my guest was Mark Suster, General Partner at Upfront Ventures. Mark brings a valuable lesson: founders must prioritize building genuine relationships before fundraising. Suster believes that cultivating trust and understanding the venture from both sides results in better alignment and partnerships, not just checks.

Like Jacques in episode 171, Mark highlights how startups can thrive by slowing down to build clarity and connection rather than rushing toward capital or unfiltered pushback. Financial success follows strategic patience and relational depth; not the other way around.

Community Involvement: Technion

Beyond venture capital, Jacques Benkoski serves on the board of his alma mater, Technion (Israel’s top technical university). He also actively supports nonprofits focused on fostering connection in conflict zones. Jacques advocates for cross-border dialogue and engagement especially between individuals with long histories of political tension.

In a striking example, he once brought a Syrian CEO to a conference in Israel. It was a gesture that changed perspectives and built new bridges.

In his own words, “People need to know each other… and forgetting the conflict, see what could be done.”


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

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, Typos on a slide deck are not a concern for me, and I prefer engaging with entrepreneurs in the early stages of their pitch deck development. However, the conventional pitch deck remains a significant tool for many venture capitalists. It serves effectively as pre-meeting reading or post-meeting review material. The critical aspect is the seamless alignment of your narrative, actual presentation, and the deck itself, ensuring clarity and comprehension. The deck should amplify...

Hello Reader, At Sure Ventures, our core mission is to empower individuals with peace of mind, and we believe true peace of mind begins with good health. Unfortunately, the current healthcare landscape is riddled with inefficiencies and challenges. It's time for innovative solutions to disrupt the status quo. The U.S. healthcare industry is a colossal force, reaching approximately $4.9 trillion in 2023 and accounting for a staggering 17.6% of our nation's GDP. It's one of the largest sectors...

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...