Spend a single afternoon inside a diversified holding company and you will see an endless stream of founder meetings, some scheduled months in advance, others arranged on the fly because a promising idea surfaced overnight. We invest capital, time, talent, and technology, so every conversation must help us decide whether the next venture belongs in our ecosystem.
Over the years we have refined a set of favorite questions that act as guideposts during these talks. We will not spill the exact wording here (there is no substitute for an authentic, in-the-moment conversation), but we can pull back the curtain on why we ask what we ask and how those answers shape our investment decisions.
Investing is never just numbers on a spreadsheet. At the early stage, it is mostly a test of conviction: do we believe this founder can turn today’s sketch into tomorrow’s sustainable enterprise? Crafting the right line of inquiry helps us find that conviction quickly, respectfully, and without putting the founder on the defensive. A hurried or generic interview wastes everyone’s time and usually pushes a promising partner toward a different source of capital.
When a founder walks through our door, they might be bracing for a dragon’s-den style grilling. We disarm that mindset by framing the session as the first page of a long-term collaboration. Good questions communicate curiosity and empathy at the same time. They reveal whether we share a vision for the business and whether the chemistry feels right for a multi-year journey.
Even seasoned entrepreneurs occasionally rehearse slick sound bites. The clues we trust most rarely come from the headline answer. We watch for:
Reading those signals tells us more about future execution than a perfectly memorized pitch ever could.
Every business is unique, but the underlying issues that determine success are surprisingly constant. Think of them as lanes on a freeway; by steering the conversation through each lane, we gain a panoramic view of what lies ahead.
We start by mapping how boldly, and realistically, the founder sees the future. Instead of reciting market size statistics ourselves, we encourage the entrepreneur to articulate where they are placing the biggest bet: customer pain, timing of adoption, and the wedge that lets a newcomer outmaneuver incumbents. We listen for the marriage of ambition and restraint. A grand vision is inspiring; a grand vision anchored to an identifiable beachhead is investable.
Strategy collapses without craftsmanship. Our inquiry in this area probes how the founder sets priorities, tracks progress, and reallocates resources when facts on the ground change. We are not looking for a textbook methodology. We are looking for a habit of disciplined iteration: prototypes on Friday, feedback on Monday, and measurable learning the next Friday.
If the founder already runs that cadence with a two-person team, we trust they can scale the habit as head-count grows.
A great idea inside a toxic culture seldom makes it to Series B. Accordingly we dig into hiring philosophy, decision making norms, and the founder’s approach to role design as complexity increases. A telling moment arrives when we ask them to describe a recent disagreement inside the company and how it was resolved. A mature leader sees conflict as a design problem, not a personal affront.
Some founders are numbers-first innovators, comfortable slicing retention cohorts but less eager to paint a big picture. Others are gifted storytellers whose metrics spreadsheet looks like it was rushed the night before. We need to hear both sides. Revenue composition, gross margin path, cash burn versus milestones, every data point must reinforce the overarching narrative. When numbers and stories diverge, we pause the process until reconciliation occurs.
Finally we zoom in on the human behind the plan. Startups are emotional roller coasters; stamina and mental flexibility matter as much as technical talent. We look for hints of how the founder recharges, who holds them accountable, and how they process failure. A founder who can laugh at a past misstep without diminishing its seriousness signals maturity we value highly.
The same question landed at the wrong moment can backfire. Early in a relationship we ask broad, open-ended prompts to gather context and establish trust. As we edge closer to an investment decision, the conversation becomes more granular: customer acquisition cost by channel, supply-chain contingencies, IP protection.
We schedule these deeper dives only after the founder agrees that exploring sensitive details is worth everyone’s time. Respecting that pacing shows we understand the pressures of running a young company while courting investors.
We never forget that founders disclose proprietary insights during these meetings. We set clear confidentiality expectations and, when appropriate, sign mutual NDAs before the first slide deck appears. Those simple gestures lower the guardrails so we can have forthright, data-rich conversations.
It sounds obvious, but too many investors hijack the meeting with war stories. We cap our own airtime to roughly thirty percent. That forces the founder to fill the silence with what really matters to them, not what they assume we want to hear. Paradoxically the less we speak, the more genuine information we receive.
After the meeting ends, we regroup internally with notes still fresh. Each theme discussed above becomes a checkpoint:
No single criterion outweighs the rest. A brilliant product may buy time, but if the culture or unit economics are flawed, we decline. Conversely, if a founder demonstrates world-class grit and a knack for rapid iteration, we may lean in even when traction is embryonic. The key is an honest, holistic appraisal, grounded in everything the founder revealed, intentionally and unintentionally, during our discussion.
The art of questioning founders is less about trapping someone in a logic puzzle and more about choreographing a conversation that surfaces character, competence, and compatibility. When that choreography is done well, both sides leave the room energized. The founder feels understood rather than interrogated, and we step away with a clear sense of whether the company belongs inside our holding company’s portfolio.
Years of trial and error have taught us that thoughtful questions accomplish three things at once: they elevate the founder, sharpen our investment hypothesis, and set the tone for a partnership that might last a decade. Ask poorly and you squander trust before the term sheet even hits the table. Ask artfully and you create the foundation for shared success, no matter how unpredictable the road ahead.
Ryan Schwab serves as Chief Revenue Officer at HOLD.co, where he leads all revenue generation, business development, and growth strategy efforts. With a proven track record in scaling technology, media, and services businesses, Ryan focuses on driving top-line performance across HOLD.co’s portfolio through disciplined sales systems, strategic partnerships, and AI-driven marketing automation. Prior to joining HOLD.co, Ryan held senior leadership roles in high-growth companies, where he built and led revenue teams, developed go-to-market strategies, and spearheaded digital transformation initiatives. His approach blends data-driven decision-making with deep market insight to fuel sustainable, scalable growth.
