High Risks, Wild Rides & Big Wins With Yousuf Khan of Ridge Ventures
We covered everything from API to DPI—talking to Yousuf feels like unlocking a vault of timeless wisdom.
As I walked out of the recording studio, I couldn’t help but think, “What you hear is exactly what you get with Yousuf.” It’s rare to meet someone who instantly elevates your confidence, makes you feel energized, and comfortable — even when you’ve never met in-person. That, my friends, is Yousuf Khan in a nutshell: completely likable and unapologetically authentic.
During our two-hour conversation, his enthusiasm was infectious. Off-camera, I joked with him, "Yousuf, you speak entirely in Instagram-worthy, bite-sized content!" Everything he said could be clipped and shared as a reel — each segment a golden nugget filled with inspiration or practical wisdom. It's not often you meet someone with that level of mastery in both craft and communication. I left inspired, to say the least.
Another thing that stood out was how he constantly kept giving credit to others during the interview — his current and former colleagues at Ridge, Pure Storage, Moveworks, and others. He highlighted the collaborative nature of his journey, never positioning himself as a lone genius but as a leader empowered by collective effort. It reminded me of a powerful leadership truth: the best leaders don't seek to take all the credit; they uplift those around them. Venture capital, after all, is a team sport. You win and/or lose together.
Here Are Some Things That Stood Out To Me In Our Chat
Customer Mode, Not Founder Mode
One of the more thought-provoking moments was Yousuf’s view on being in “customer mode.” This idea, which contrasts with the more traditional notion of "founder mode," struck a chord. It’s also a widely contested topic dividing the startup world, especially on Twitter/X. Paul Graham famously wrote about the importance of founder-first thinking, suggesting that great products and companies are built when founders trust their instincts over external voices.
Yousuf, however, flips this notion on its head. He argues that founders must immerse themselves in "customer mode," meaning they need to develop deep empathy for their customers. He emphasized, “You have to be the customer to sell to the customer.” This is not just about listening to feedback — it’s about becoming obsessed with understanding customers at different scales and levels, particularly in the complex world of enterprise.For Yousuf, enterprise customers evolve constantly. Founders who thrive are those who engage across multiple touch-points: talking to stakeholders in IT, security, procurement, and finance, not just the C-suite. “Enterprise deals are made by consensus,” he said. “The more people who know you and your product across the organization, the greater your chances of success.” This approach isn’t just tactical; it’s strategic relationship-building at scale.
It’s about knowing not only what the customer wants today but also anticipating how their needs will evolve over time.Iterate, But Don’t Get Lost in Perfection
Founders often fall into the trap of endless iteration, hoping to perfect their product before scaling. Yousuf believes this is a flawed approach. “The entire tech industry is built on imperfection,” he said. “If everything were perfect, there’d be no room for innovation or startups.” In a world that often fetishizes perfection, Yousuf’s advice was refreshingly grounded.
He continued to cite examples like Zoom and Moveworks — companies that didn’t have every feature on day one but still won customers through exceptional focus and execution. Yousuf’s advice? Ship the best version you can, learn quickly, and continuously improve. Perfect is the enemy of progress.
Venture Capital’s Long Feedback Loop
Venture capital is a long-term game, and patience is key. Yousuf explained how one of the hardest aspects of the job is dealing with the delayed feedback loop. “You invest today, but it may take years to see if that decision pans out,” he said. This is why building strong relationships with founders and maintaining conviction in your thesis is crucial.
The line of progress is not drawn straight.
Be it venture or the startups, or even life, it’s a long journey, and the line of progress is rarely straight — but if you keep moving forward, success will follow.
This philosophy for navigating the highs and lows offers a subtle yet profound reminder — one that often goes unsaid but, when articulated, leaves you thinking deeply. It's about resilience, learning from each cycle, and staying focused on long-term value creation rather than getting distracted by short-term headlines.The Power of Storytelling
As Yousuf spoke about the power of storytelling, it became evident that he wasn’t just sharing advice — he was embodying it. Within minutes, I found myself completely engaged, realizing that storytelling with Yousuf isn’t just about relaying facts or anecdotes. It’s about weaving a narrative that makes you feel part of the journey. Few people in life, let alone venture, can capture your attention and energy the way he does.
Storytelling, as Yousuf explained, is essential for both founders and investors, and it goes far beyond just talking — it’s about creating a shared experience with the audience. He stressed that founders, in particular, need to master this skill, not just for raising capital but to communicate their vision and values with clarity and conviction — it becomes the foundation to a company’s success.
Crafting an impression requires more than just listing achievements or features. It’s about constructing a cohesive narrative: your background, the market opportunity, your product’s purpose, and the long-term vision — all while maintaining a level of authenticity that resonates and sticks. Yousuf's words reminded me that storytelling is the bridge between ideas and impact, and mastering it can be the difference between a pitch that fades and one that’s unforgettable.
As I reflected on our conversation as I finished editing the episode, I realized there’s a reason Yousuf Khan is so respected among his peers in both startups and venture. His success is built on more than just investment or tech/business acumen. It’s his relentless focus on relationships, empathy, and deep understanding of people that sets him apart.
Spending time with him was a reminder that great leaders elevate everyone around them — by being authentic, thoughtful, and endlessly curious. Whether he’s guiding founders through tough decisions, mentoring aspiring CIOs and VCs, or simply being a connector in the industry, his impact is driven by empathy and service. He’s not just in venture capital to invest in companies — he’s in it to build lasting relationships and help people succeed.
In today’s fast-paced TikTok and Instagram world, where hype and quick soundbites dominate, Yousuf’s grounded approach serves as a powerful reminder of what truly matters: listening, learning, and lifting others up.
If you want to learn more about Yousuf’s journey and insights, I highly recommend tuning into the full episode of The Desi VC Podcast. His stories, lessons, and advice are sure to leave you both inspired and motivated to take your own journey to the next level.
I’m incredibly grateful for this conversation and can’t wait to share more insights from our discussion. Until then, I’ll leave you with this: Be in customer mode. It’s never too late to start.
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A big thank you to my team and friends at F Inc. for making the production of every episode possible.
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