Mastering Buyside Deal Sourcing: Part Two - Conducting The Call
The Deal Sourcing Call: Your Gateway to Meaningful Investment Relationships
Apologies, this is a bit of a long post but hear me out. You've worked hard to get an initial call. The cold emails, the warm introductions, the networking events—all of that effort has broken through to this opportunity. Now you have 30-60 minutes with a founder or CEO, and it's crucial to recognize this call for what it truly is: an opportunity to nurture a relationship that could lead to a deal. This is the long game, and first impressions matter immensely. You have to come prepared.
It's Not an Interview—It's an Authentic Conversation
The biggest mistake sourcing teams make on initial calls is treating them like a formal interview or due diligence session. This approach immediately creates an adversarial dynamic that undermines relationship building. Instead, approach the call as an authentic conversation that comes from a place of genuine interest and curiosity in the business, the market, and the people behind it.
Authentic conversations flow naturally. They build on previous points, explore tangential but relevant topics, and create space for both parties to share insights. When founders feel like they're being genuinely heard rather than interrogated, they're more likely to open up about the real challenges and opportunities in their business—information that's far more valuable than rehearsed pitch deck talking points.
Be Willing to Challenge—Thoughtfully
While the call shouldn't feel like an inquisition, you also can't be a passive listener. Part of demonstrating your value is showing that you can think critically about the business. Be willing to challenge assumptions when appropriate, but do so from a place of curiosity rather than skepticism.
The key is framing these challenges as collaborative exploration rather than confrontational questioning. You're not trying to poke holes in their strategy; you're trying to understand how they think about their business and whether they've considered the key risks and opportunities.
Building Relationships Takes Time and Intentionality
Remember that you're building a relationship, not just evaluating an investment or acquisition opportunity. The best deals often come from relationships that have been nurtured over months or years. Even if this particular opportunity isn't the right fit, the founder might start their next company, or recommend you to a peer, or join another portfolio company as an executive.
Show genuine interest in their story. Ask about their background, what led them to start this company, what they've learned along the way. Share relevant experiences from your own portfolio or investment experience when appropriate. Look for ways to be helpful beyond just potential funding—introductions to customers, advisors, or other investors can go a long way toward building goodwill.
Preparation Is Non-Negotiable
To make any call go well, preparation is essential. You cannot wing it and expect to build credibility or add value. Your homework should cover three key areas:
Company Research: Dig into their website, product demos, customer testimonials, and any available content. Understand their product positioning, pricing model, and go-to-market strategy. Look for recent news, partnerships, or product launches.
Market Understanding: Develop a general understanding of the market landscape, key trends, and competitive dynamics. You don't need to become an expert overnight, but you should understand the basic value proposition and how this company fits into the broader ecosystem. Research the main competitors and understand the differentiation thesis.
Question Strategy: Prepare a list of thoughtful questions in advance, but don't treat it as a rigid script. Your questions should demonstrate that you've done your homework and are thinking seriously about the opportunity. Mix tactical questions about the business with strategic questions about market positioning and vision.
The Long-Term Mindset
Approach every call with a long-term perspective. Even if this specific opportunity doesn't lead to an investment, every interaction is a chance to build your reputation in the market and expand your network. Founders talk to each other, and word spreads quickly about which investors are thoughtful, prepared, and genuinely helpful.
Be responsive after the call. If you're not interested, communicate that clearly and promptly, ideally with constructive feedback. If you are interested, move quickly to outline next steps. Either way, look for opportunities to be helpful—whether that's making an introduction, sharing a relevant article, or simply providing thoughtful feedback on their strategy.
Our Approach at Ocean Crest Advisory
This is exactly how we approach calls at Ocean Crest Advisory. We come to every conversation with genuine interest in your business and the entrepreneur or CEO, not as a box-checking exercise to fill out data in our CRM for our clients. We bring our experience and thorough preparation to truly connect with CEOs and founders. Their time is valuable, and we treat it as such.
