A New Funding Framework
How One Executive Coach Is Rewriting the Rules of Startup Fundraising
Former 500 Global exec Vijay Rajendran on why your best investor might be your customer, not a VC
Summary
- Vijay Rajendran transitioned from Head of Portfolio Value at 500 Global, to executive coaching to create more direct, personal impact with founders.
- His book "The Funding Framework" emphasizes that venture capital isn't always the best first funding source, encouraging founders to validate through customer sales before chasing investors.
- He observes major funding trends, including shifts toward emerging regions, strategic capital, and growing skepticism of blitzscaling, advising founders to show "momentum and substance, not just sizzle."
- Looking ahead to 2025, Vijay is focusing on gAI Ventures, a new venture builder creating vertical AI companies, while continuing to develop tools and frameworks for leadership growth.
Introduction
Vijay Rajendran is a Berkeley-trained executive coach, entrepreneur, investor, and advisor with over two decades of experience in the startup and venture ecosystem. He previously served as Head of Portfolio Value at 500 Global, where he supported more than 2,700 startups across 81 countries, helping founders overcome challenges in fundraising, scaling, and leadership.
In March 2025, Vijay published The Funding Framework: Secure Startup Funding With Confidence, a practical guide widely praised within the startup community for its actionable insights into mastering the fundraising process.
This work complements his coaching practice and advisory engagements, through which he remains especially committed to supporting underestimated founders with personalized, group, and executive coaching programs.
Currently, Vijay partners with early-stage founders as an executive coach and strategic advisor at gAI Ventures and Climate Angels. These startup advisory platforms focus on accelerating innovation in generative AI, climate tech, and other high-growth sectors that drive systemic change and create long-term value.
gAI Ventures and Climate Angels provide strategic guidance in fundraising, market entry, and leadership growth, allowing startups to scale sustainably and turn innovative concepts into meaningful, long-term success.
Together, these platforms have backed dozens of startups globally in fast-evolving fields like artificial intelligence, clean energy, and frontier technologies.
Through his combined expertise and these partnerships, Vijay continues to empower founders and leaders to build resilient organizations and high-impact startups with a focus on authentic leadership, sustainability, and inclusive innovation.
HubSpot for Startups connected with Vijay Rajendran to discuss his evolution from venture capital to executive coaching, his approach to helping startup leaders succeed, and his insights for emerging founders.
"Coaching gives me the privilege of helping leaders navigate the tough stuff, the high-stakes decisions, the impostor syndrome, the moments when everything feels like it’s on the line."
— Vijay Rajendran
Transition to executive coaching
HubSpot for Startups: What motivated your transition from your role at 500 Global to becoming an executive coach for startup founders and CEOs?
Vijay: After years working in venture capital, I felt a pull toward a more direct, personal kind of impact, the kind you can only have when you're working one-on-one with a leader at an inflection point. Becoming an executive coach enabled me to shift from evaluating companies to empowering the individuals who build them.
I wanted to support founders and CEOs not just with capital or strategy, but with the mindset, clarity, and resilience required to lead. Coaching gives me the privilege of helping leaders navigate the tough stuff, the high-stakes decisions, the impostor syndrome, the moments when everything feels like it’s on the line.
Venture capital experience and coaching approach
HSFS: How has your experience in venture capital shaped your approach to executive coaching and leadership development?
Vijay: My background in venture gives me a sharp lens on what founders face. I’ve seen what works and what doesn’t across dozens of startups. That experience shapes how I coach. I help leaders think through strategic decisions, build genuine investor relationships, and grow into the kind of CEOs their companies need.
Whether it’s navigating complex term sheets or scaling leadership alongside the business, I bring a practical, investor-savvy approach to our conversations.
Insights from The Funding Framework
HSFS: Your book, The Funding Framework, offers practical advice for founders. What key insights or strategies do you hope readers will take away?
Vijay: I discuss a truth that many founders overlook: venture capital isn’t always the best or first source of funding. Sometimes the smartest money comes from your customers. I encourage founders to validate their business through real sales before chasing investors.
That not only builds a healthier company, it also puts the founder back in the driver’s seat. It’s about raising from a place of strength, not scarcity. But if they do want to raise, they should know that it is a learned skill based on storytelling, organization, outreach, and closing with confidence.
Meaningful coaching engagement
HSFS: Could you describe a recent coaching engagement that had a meaningful impact on a founder or leadership team you worked with?
Vijay: Recently, I worked with a founder who was struggling to break through a rough fundraising season. We focused on mindset, energy, and storytelling, and the shift was profound. She found her rhythm again. Her team felt it too.
The conversations became clearer, the decisions more grounded, and she started showing up with a sense of lightness that had been missing. That’s the kind of transformation that energizes me most.
The founder was indeed struggling to connect with investors, which directly impacted her ability to raise capital. Her product focused on a new solution for childcare, particularly in large cities. The mindset shift was pivotal. Specifically, she moved from a place of scarcity and self-doubt to one of abundance and confidence. This transformation in her personal energy and belief in her vision directly translated into more confident storytelling during pitches. The most significant mindset shift is that your story matters and that others want to know it and hear about it. If you believe that there are investors with a thesis that matters and that matches what you are focused on, then you should let your story bring that out and let those people find you.
"The most significant mindset shift is that your story matters and that others want to know it and hear about it." — Vijay Rajendran
Balancing multiple roles
HSFS: How do you manage your various roles as a coach, author, advisor, and philanthropist while maintaining focus and effectiveness?
Vijay: Like many of the leaders I coach, I juggle multiple roles: coach, author, advisor, and philanthropist. I’ve learned to prioritize based on what aligns with my values and where I can create the most leverage.
I rely on systems that help me manage energy more than just time, and I try to model the same intentionality I encourage in my clients. It’s a practice, and I’m continually refining it.
Trends in startup funding
HSFS: What major trends or challenges are you currently seeing in the startup funding landscape, and how are you advising founders to navigate them?
Vijay: Startup funding is evolving. There’s a clear shift toward emerging regions, more strategic capital, and a growing skepticism of the traditional blitzscaling model.
Founders today need to show momentum and substance, not just sizzle. Building strong investor relationships, based on absolute trust and consistent execution, is more critical than ever.
"Founders today need to show momentum and substance, not just sizzle."
— Vijay Rajendran
Future projects and goals
HSFS: Looking ahead, what projects or goals are you most excited about for 2025 and beyond?
Vijay: Looking to 2025 and beyond, I’m excited to spend most of my time on gAI Ventures, a new venture builder creating vertical AI companies. Whether coaching or investing, I'll be developing new tools and frameworks to support leadership growth and continuing to write and speak about what it takes to lead a startup.
My mission is simple: to help bold leaders become successful, and to do it in a way that scales their impact, not just their valuation.
Coaching founders to scale with vision and resilience
Vijay Rajendran shows how deep venture capital expertise, executive coaching, and philanthropy can together drive meaningful transformation. Through his work with startup advisory platforms, authorship, and strategic guidance, he continues to empower founders to navigate the complexities of scaling high-growth ventures with confidence and purpose.
With the startup ecosystem's evolution, leaders like Vijay play an important role in fostering innovation, inclusivity, and sustainable success. They ensure that the next generation of entrepreneurs is well-equipped to create a meaningful, lasting impact.
