The Desi VC with Akash Bhat E147 - Tips for B2B Enterprise Founders | Yousuf Khan (Ridge Ventures)
Yousuf Khan is a Partner at Ridge Ventures, a seed and Series A stage venture fund investing in enterprise and B2B startups. With a deep understanding of startup growth and scaling challenges, Yousuf not only drives Ridge’s investment portfolio forward but also provides hands-on support to founders, offering guidance rooted in his extensive experience across leadership roles. He currently serves as a board director for Ridge-backed companies, including Archera, Cerby, Chisel Labs, Lightyear, Rafay, and Rewind.
Before joining Ridge, Yousuf held several pivotal positions in leading technology companies. He was the first CIO of Automation Anywhere ($6.84 billion company), played a dual role as CIO and Vice President of Customer Success at AI-driven cloud platform Moveworks ($2.1 billion company), and served as CIO at two public companies, Pure Storage (PSTG) and Qualys (QLYS). His deep industry expertise also includes advisory roles with companies like Zoom, Productiv, and Material Security.
In this episode, Yousuf shares his journey into venture capital, discussing key insights on building a career in VC, the importance of founder empathy, and the role of self-awareness and diversity in investing.He offers practical advice on how VCs can create information arbitrage, draw value from feedback cycles, and support founders through challenges at scale. The conversation also delves into best practices and strategies for enterprise software founders, covering topics like customer obsession, board meetings, and leadership at scale.
⌛ Timestamps:
- Trailer (0:00)
- Introduction (1:40)
- Episode kick-off (3:44)
- Yousuf shares his experience in venture capital (4:26)
- Is venture capital for everyone? What should one expect? (5:20)
- Knowing your 'WHY' before starting a career in VC (7:13)
- How to become a venture capitalist (9:00)
- How VCs draw inferences from feedback cycles (11:44)
- Creating information arbitrage as a VC (14:41)
- The importance of diversity in a venture team (16:46)
- The role of founder empathy in investing (18:25)
- Authenticity: An underrated trait in founders (19:39)
- Why VCs should have self-awareness (22:07)
- Common problems founders face as they scale (25:07)
- Why very few CIOs become VCs (27:00)
- API to DPI: The journey of an investor (32:34)
- How to build a strong track record in venture (36:40)
- Speaking the talk vs. walking the walk (39:00)
- The importance of obsession in venture capital (41:06)
- Serendipity and opportunity in VC (43:01)
- Immigrant spirit, shared experiences, and gratitude in venture (47:37)
- How Yousuf handles failures or bad investments (59:06)
- Best practices for running board meetings (1:06:07)
- The science of creating a perfect board deck (1:08:10)
- How long it takes founders to master board meetings (1:10:35)
- Tips for founders on running their companies better (1:12:32)
- Why the technology industry is inherently imperfect (1:14:15)
- The importance of operating in "customer mode" (not just founder mode) (1:20:16)
- Advice for enterprise software founders (1:24:54)
- What’s ahead for 2025 (1:26:58)
- Advice Yousuf would give his younger self (1:30:10)
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