The Questions Great Founders Ask (and Why They Matter)

At Blumberg Capital, we’ve found that the best founder–investor conversations often begin not with pitch decks or metrics, but with curiosity and a desire to learn faster.

The questions below, drawn directly from real founder–investor conversations across our team, reflect that mindset. They highlight how great founders think about alignment, transparency, timing, and the long-term journey of company building.

The Power of Asking Better Questions

Early-stage companies thrive on curiosity. Asking the right questions of your investors, your partners, and yourself can reveal blind spots, clarify expectations, and strengthen relationships. The questions we’ve heard most often lately tend to come from founders who are reflective, grounded, and intentional about the type of company they want to build.

They aren’t simply looking for capital; they’re looking for collaboration. Each question below reveals something about the founder mindset, including how leaders think about risk, value, and shared accountability.

What Kind of Board Member Would You Be if Things Didn’t Go to Plan Early On?

“This one stuck with me. Beneath the surface, it’s really asking: Are you in it for the long haul, or only when everything looks perfect?”
— Jacob Katz, Principal, Miami

It’s easy to build relationships when things are going well. The real test of partnership often comes when results fall short or challenges arise. By asking this question, founders are signaling something deeper: they want to understand how investors behave in moments of uncertainty.

The subtext isn’t about distrust; it’s about alignment. Founders want to know whether their board members will offer guidance, patience, and perspective when it’s needed most. This question reframes the relationship as a two-way commitment — one built on resilience and transparency.

What Risks Do You See in This Business?

“A simple question that signals transparency, strategic thinking, and a willingness to confront challenges.”
— Pramod Gosavi, Sr. Principal, San Francisco

No early-stage venture is risk-free. The best founders know this and invite feedback rather than avoid it. This question opens a space for honest discussion about potential pitfalls, from market timing and product differentiation to regulatory uncertainty.

It also tells investors that the founder is self-aware enough to value constructive criticism. In an environment where optimism is often necessary for momentum, this kind of realism stands out. Asking about risks early helps set a tone of openness that serves both sides long after the first funding round.

How Should We Be Thinking About Timing Expectations?

“This founder had their feet on the ground and understood the hard work ahead.”
— Juan Pujadas, Advisor to Blumberg Capital and Veteran Technology and Business Leader

Timing plays a decisive role in startup success. Launching too early or too late can make the difference between traction and stagnation. Founders who ask this question show they’re thinking carefully about pacing, not just in terms of product rollout, but also fundraising cadence and milestone setting.

It’s also a signal of maturity. A founder who can discuss realistic timelines is demonstrating both discipline and strategic foresight. For investors, it’s a clear indicator that the company is built on thoughtful planning rather than wishful thinking.

How Should We Navigate a Conversation with a Strategic Investor Who Wants to Buy Our Company Early?

“Founders should lean on their investors to help optimize outcomes — whether navigating a potential exit or hiring a C-level executive. While it may be a founder’s first or second time, investors and board members bring the advantage of pattern recognition, having been through similar situations dozens — if not hundreds — of times.”
— Bruce Taragin, Managing Director, New York

Early acquisition interest can be both exciting and complex. For a first-time founder, such a scenario can introduce hard questions: What’s the right valuation? Is it too soon? What would the team gain or lose by exiting early?

This is where the founder–investor relationship becomes a true partnership. As Bruce Taragin notes, investors have pattern recognition. Their experience across many similar situations can help founders weigh long-term strategic value against short-term opportunity. Asking for that guidance is a mark of trust and self-awareness.

How Can Geopolitics Serve as a Strategic Inflection Point?

“A great question, especially given how recent geopolitical developments and U.S. policies — including those related to technologies like semiconductors, quantum computing, AI, and cryptocurrencies — are reshaping industries.”
— Jacob Cohen, Advisor to Blumberg Capital and Associate Dean at MIT Sloan School of Management

Today’s founders operate in a world where global policy and technology are tightly linked. From export controls to AI regulation, macro forces can create both constraints and new opportunities.

By asking this question, founders show they’re thinking beyond the next product release or funding round. They’re considering how global trends could impact their trajectory. That kind of systems-level awareness can be a competitive advantage, helping companies anticipate change rather than react to it.

What Value Would You Bring to Our Company?

“An important reminder that founders should vet investors, too. The best partnerships bring expertise, connections, and alignment beyond capital.”
— Alejandro Hill, Associate, Miami & Yodfat Harel Buchris, Managing Director, Tel Aviv

Not every investor is the right fit for every company. Founders who ask this question are flipping the script by evaluating investors as potential long-term partners rather than short-term funders.

The best partnerships are multi-dimensional: they include operational insight, industry relationships, and shared values. By seeking clarity on an investor’s value beyond capital, founders ensure that their boardroom is filled with people who can accelerate learning, hiring, and execution.

Curiosity as a Competitive Advantage

Every question above stems from the same principle: curiosity. The willingness to learn, to ask, and to listen. At Blumberg Capital, we believe curiosity is one of a founder’s greatest competitive advantages.

When founders engage investors as thought partners and not just financiers, they gain more than capital. They gain perspective. They learn faster, make stronger decisions, and build companies with resilience at their core.

As one of our advisors shared, successful leaders don’t just ask smart questions; they also share what they’re learning and how they’re leading. That cycle of curiosity and reflection is what fuels great partnerships and great companies.