How do you make sure someone is asking the “dumb” questions

What Founders and Candidates Should Be Asking - But Often Don’t

In this episode of VHTB, Seyka Mejeur, Founder and CEO of AdAstra, is joined by Matt Gjertsen of Better Every Day Studios and Justus Kilian of Space Capital for a candid conversation about the kinds of questions that often go unasked. Specifically, the ones that don’t get asked enough in investor meetings, hiring conversations, and early-stage startup negotiations.

The conversation covers both sides of the table. Justus shares a set of questions founders should be asking investors, not just about capital, but how decisions are made, what the firm’s structure looks like, and who’s actually backing the fund. He also walks through questions to ask the individual partner leading your round, especially when you’re trying to understand how involved they’ll be after the deal closes.

Matt brings in examples from his own work, including how learning to say “I don’t know” or “can we slow this down” often leads to better results. Seyka shares moments from her work with technical leaders where simple, clarifying questions helped people get back on the same page, and how that applies in interviews, recruiting, and equity conversations.

Also covered: how to ask about liquidity, what candidates should know when a recruiter calls, and why experienced founders ask different questions.

Episode Highlights

00:00 Introductions and why “dumb” questions matter 

01:36 Founders and investors: the questions that don’t get asked

05:46 How to ask about decision-making and follow-on

06:47 The role of foreign capital and dual-use concerns

09:33 How to ask for clarification without overexplaining

13:14 Why experienced founders ask differently

17:02 What good equity communication looks like

21:00 How founders can make equity offers more transparent

22:00 Questions to ask the individual partner

24:00 Recap: questions worth asking early

Episode Takeaways

• Founders should be asking detailed, operational questions about how a fund runs and how involved their partner will be, not just about capital.
• “I don’t know” is a strength, not a weakness. Clarity builds trust faster than confidence does.
• Asking for equity details is reasonable and necessary. Teams should be prepared to talk in concrete terms.
• Recruiters should be transparent about their relationship with the company. Candidates have every right to ask.
• Simplifying technical conversations doesn’t water them down; it keeps everyone aligned.