In a recent LinkedIn post, Tobi Oluwole discusses a fundamental connection often overlooked by founders: the parallel between raising capital and acquiring customers. Oluwole argues that these two critical business functions, frequently compartmentalized as distinct tasks, are in fact driven by the same core strategic motion.
The common perception, Oluwole points out, is to treat them separately. “One is ‘fundraising.’ The other is ‘sales,'” he writes, highlighting the conventional, yet in his view, flawed, approach. Instead, Oluwole posits that the underlying process is identical.
“But it’s the same motion every time: Figure out who you need, find them, get their attention, start a conversation.”
Oluwole draws on his experience from both building companies and assisting those in the fundraising process to support his assertion. He emphasizes that the challenge of identifying and engaging with potential investors mirrors the process of finding and converting customers.
The Shared Search Problem
At the heart of Oluwole’s argument is the idea that both investors and customers represent a ‘search problem.’ As Tobi Oluwole notes, “a cold investor and a cold buyer are the exact same search problem.” This perspective reframes the initial outreach and engagement strategies, suggesting that a unified approach can be more effective.
Identifying and Engaging the Target Audience
Oluwole elaborates on the practical application of this unified strategy, particularly in the context of leveraging tools for efficiency. He explains that the methods for locating the right individuals, whether for investment or purchase, involve similar filtering and identification techniques.
“Finding the right investors & customers using filters, lookalikes and buying intent”
This shared methodology extends to the crucial step of initiating and nurturing conversations. Oluwole suggests that understanding the recipient’s needs and motivations is paramount, regardless of whether they are a potential investor or a customer. He highlights the importance of tailoring communication based on genuine interest and signals.
“Reading intent signals and changing your message based on what someone actually cares about”
Furthermore, Tobi Oluwole advocates for the use of structured workflows, particularly AI-assisted sequences, to manage outreach efforts for both fundraising and sales. This approach, he believes, can streamline the process and increase effectiveness.
Leveraging Workflows for Dual Objectives
The insights shared by Oluwole point towards a more integrated strategy for startups. By recognizing the commonalities between fundraising and sales, founders can potentially optimize their efforts and resources.
Tobi Oluwole is scheduled to conduct a live session with Apollo.io on September 16th to delve deeper into these workflows. The session aims to provide practical, actionable guidance, demonstrating how to utilize tools effectively for both identifying investors and acquiring customers. The focus, as Oluwole stresses, is on the practical workflow rather than a theoretical discussion of the go-to-market landscape.
“This isn’t a panel about the state of GTM. It’s the workflow, start to finish.”
This session, featuring insights from Elana Gold of Two Roads Capital and Brandon R. from Apollo’s GTM team, is designed to offer a comprehensive, start-to-finish guide. It underscores Oluwole’s belief that a unified, strategic approach to outreach is key to achieving success in both securing funding and driving business growth.
📝 About This Content
This article is based on insights shared by Tobi Oluwole on LinkedIn.
📅 Originally posted on September 9, 2026 | View original post on LinkedIn →