Founder’s Reality Check: Raising Capital in A Challenging Market
Fundraising has become an increasingly demanding exercise for founders. Investors are more selective, capital is more expensive, and the bar for demonstrating sustainable growth, sound unit economics, and a credible path to profitability is higher.
For founders looking to scale, raising capital is no longer simply about telling a compelling growth story. It is about demonstrating business resilience, financial discipline and a clear understanding of how additional capital will create value.
Join us for a candid conversation between an experienced founder and an investor as they unpack the realities of raising capital in today's challenging market.
Featuring Andrea Baronchelli, Co-Founder & CEO of Aspire, and Arun Pai, Partner at Monk's Hill Ventures, this session will explore what it takes to build investor confidence, navigate difficult fundraising conversations, and make sound financing decisions without compromising the long-term health of your business.
Whether you're preparing for your next fundraise, reassessing your valuation expectations, or deciding whether external capital is the right path, expect practical insights and honest perspectives from both sides of the table.
What We'll Explore
The changing fundraising landscape: What has fundamentally changed in how investors evaluate companies, and which expectations have become non-negotiable?
Knowing when you're ready: Beyond revenue growth, what financial and operational fundamentals demonstrate that a company is ready for institutional capital?
Valuation and deal negotiations: How should founders navigate valuation expectations, dilution, down rounds, and difficult investor conversations?
Growth versus runway: How can founders balance expansion ambitions with cash preservation and the path to profitability?
Building investor confidence: How can founders communicate financial challenges, missed targets, and changing business assumptions credibly?
Alternative paths to growth: When should founders consider bootstrapping, strategic partnerships, or non-dilutive financing instead of venture capital?
Expect an honest discussion grounded in real fundraising experiences, including difficult conversations, rejected deals, and lessons learned along the way. You will also have the chance to ask our speakers questions directly during the audience Q&A.
Featuring
THE FOUNDER: Andrea Baronchelli, Co-Founder & CEO, Aspire
From Lazada’s founding team to building Aspire into a leading fintech platform serving 50,000+ businesses globally, Andrea knows what it takes to raise capital and scale through different market cycles. He brings a founder’s firsthand perspective on navigating investor expectations, balancing growth with capital efficiency, and convincing investors to back ambitious businesses when capital is harder to come by.
THE INVESTOR: Arun Pai, Partner, Monk's Hill Ventures
Having sat on both sides of the fundraising table—as a fintech entrepreneur and now an early-stage investor at Monk’s Hill Ventures—Arun understands what founders face when raising capital. With a background in investment banking at Lehman Brothers and Nomura, he brings a candid investor’s perspective on what makes a startup fundable, how investment decisions are made, and what separates founders who secure funding from those who struggle in a selective market.
Who Should Attend?
This session is designed for founders who have achieved initial traction in their home market and are preparing to scale into regional and global markets.
Particularly relevant for founders navigating the Seed to Series B stages who are considering their next fundraise, strengthening their financial fundamentals or evaluating alternative paths to growth.
Agenda
➡ 12:30 PM – 1:00 PM | Registration & Networking: Arrive, collect your name tag, and connect with fellow founders ahead of the session.
➡ 1:00 PM – 2:30 PM | Founder’s Reality Check: Raising Capital in A Challenging Market: Moderated discussion featuring Andrea Baronchelli and Arun Pai, followed by an open audience Q&A.
➡ 2:30 PM onwards | Celebrating Dare to Scale Cohort 1: Join us as we celebrate the founders completing the inaugural Dare to Scale cohort and welcome them into the wider Endeavor community.
About Dare to Scale
Dare to Scale is a founder-focused, non-dilutive support programme led by Endeavor and supported by Enterprise Singapore. Designed for Singapore-based founders and startups that have achieved product-market fit, the programme helps businesses scale beyond Singapore through access to experienced mentors, practical learning opportunities, peer networks and connections to global markets.
Through curated masterclasses, mentorship and founder-to-founder learning, Dare to Scale equips entrepreneurs with the insights, relationships and support needed to navigate the challenges of building and scaling high-growth businesses.
Learn more: www.dare-to-scale.com