#401 Inside the Investor’s Mind: Adrian Mendoza’s Journey from CTO to Venture Capitalist

The CTO Show with Mehmet Gonullu

In this episode of The CTO Show with Mehmet, we’re joined by Adrian Mendoza, General Partner and co-founder of Mendoza Ventures. Based in Boston, Adrian has carved a unique path from being a tech founder and CTO to a venture capitalist, specializing in AI, fintech, and cybersecurity investments. With firsthand experience navigating the startup ecosystem, Adrian brings a unique empathy and understanding to his role as an investor. He shares his journey from startup founder to venture capitalist, discussing the valuable lessons he learned along the way.

Adrian begins by describing his early career as a tech founder, where he built and sold two startups. His background as a founder-turned-CTO gave him a deep understanding of the challenges tech founders face, from bootstrapping and scaling to managing exits. In this conversation, he explains why he decided to move “to the other side of the table” as an investor, emphasizing his desire to bring an empathetic, founder-focused approach to venture capital. Adrian’s unique perspective has shaped Mendoza Ventures, where he and his partners are committed to creating meaningful connections between founders and investors.

The conversation delves into the VC world, demystifying how venture funds operate and what they seek in early-stage startups. Adrian outlines the typical process startups go through when approaching VCs, highlighting common mistakes founders make when pitching. He discusses the importance of finding the right investment partner—someone who understands both the technical aspects of the business and the market potential. Adrian also stresses the need for founders to view fundraising as a sales process, where it’s essential to qualify leads and tailor pitches to the specific interests of investors.

As an investor, Adrian offers valuable advice on how founders can improve their chances of securing funding. He talks about the importance of traction and revenue, explaining that repeatable revenue signals a startup’s potential for growth and scalability. Drawing from his technical background, he shares insights on due diligence, emphasizing how a strong architectural foundation in a startup’s tech stack is crucial for sustainable scaling.

More about Adrian:

Adrian is the founder and general partner at Mendoza Ventures which is both Latinx and woman-owned and the first Latinx-founded VC fund on the East Coast based in Boston. With 20 years’ of experience in building technology products and teams, Adrian is an experienced entrepreneur, operator, and veteran of the Boston startup ecosystem. Adrian founded Mendoza Ventures to take an in-depth-focused approach to venture capital, looking for founders who demonstrate domain expertise in one of his three focus areas across fintech, AI, and cybersecurity. Adrian prides himself on being a hands-on investor by setting up companies for success beyond just writing a check, creating strong funding syndicates, making customer introductions, and assisting with partnership conversations.

https://mendoza-ventures.com/

https://www.linkedin.com/in/adrianmendozavc/

00:00 Introduction and Guest Welcome

01:16 Adrian Mendoza's Background

02:39 Transition from Founder to Investor

04:34 Challenges and Insights for Founders

06:24 Understanding the VC Perspective

08:33 Qualifying Leads and Fundraising Strategies

15:00 When to Approach Angels vs. VCs

24:11 Adrian's Investment Philosophy and Red Flags

31:16 Building the Early Team

32:24 Flexibility in Founding Vision

33:12 Importance of Repeatable Revenue

34:38 The Reality of IPOs and Exits

37:30 The Role of a CTO in Startups

44:50 Challenges in AI Startups

51:24 Cybersecurity Market Insights

53:24 Innovations in FinTech

55:13 Global Investment Strategies

57:17 Impact and Inclusion in Venture Capital

01:00:46 Closing Remarks and Contact Information