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Demystifying the Investment Process - Interview with Jake O'Shea

In today’s episode of If Not Now Wen, we’re so excited to talk with special guest Jake O'Shea. Jake is a professional match-maker and superconnector. He currently works as the Director of Portfolio Operations at Foundation Capital, building tools and systems to operationalize the firm's network and leading the 30yo firm's Platform and Portfolio Support functions.

Prior to Foundation Capital, Jake was Director of Platform at Capital Factory, where he was responsible for managing and developing the firm's value-add initiatives for portfolio companies. Jake is a co-organizer of AITX, a local Austin AI community. He is also cofounder of, a GPT-powered network management tool, and creator of ShowerThoughts, allowing you to turn your unstructured brain dump into a short summary with highlights and action items that are delivered directly to your inbox.

In this episode Jake gives an inside look into the venture capital business model and has an incredible way of demystifying the investment process in a way that is very clear and refreshing. He is an open book and gives clear steps and game-changing advice for founders.

We talk about:

🔹 The 3-step process for successful fundraising

🔹 Understanding the different rounds of funding

🔹 How to create an incentive for a lead investor to offer you a term sheet

🔹 Determining the right valuation for your company

🔹 How to build relationships with potential investors

Jake has such a big heart, and he is passionate about supporting others and creating a positive impact.  He is a leader with a wealth of knowledge and insights that are incredibly important for founders. I know you are going to love this episode and get so many amazing take-aways.

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