SATURDAY, AUGUST 22, 2026
Published Daily in New York & Silicon Valley.
Latest News 21 AUGUST, 2026

What VCs Actually Want from Founders: Insights from a $1B Fundraising Expert

Founders who understand their company's financial reality can raise funds with more confidence and leverage.
NEWS DESK PUBLISHED: AUGUST 21, 2026
📖 3 MIN READ

Understanding the Financial Reality of Your Business

Investors value founders who have a strong grasp of their company’s financial reality. Messy data, misunderstood metrics, or waiting until you’re nearly out of cash to start fundraising can cost founders leverage, valuation, and even a term sheet. In this article, we’ll delve into the key takeaways from a conversation between Isabelle Johannessen and Sasha Orloff, founder and CEO of Puzzle, on what investors look for during fundraising.

Raising Over $1 Billion: What Sasha Learned

Sasha Orloff, a seasoned entrepreneur with multiple companies that have collectively raised over $1 billion, shares his insights on fundraising. He emphasizes the importance of understanding the financial reality of your business and having a strong grasp of key financial metrics. This includes revenue growth, quality of revenue, runway, margins, sales efficiency, and profitability. By being aware of these metrics, founders can raise funds with more confidence and leverage.

Financial Metrics Founders Should Know

Sasha highlights the critical importance of revenue growth and the quality of that revenue. Investors want to see consistent revenue growth, and the quality of that revenue is also crucial. Founders should be prepared to discuss how they plan to achieve and sustain revenue growth. Additionally, they should have a clear understanding of their company’s runway, margins, sales efficiency, and profitability. By having a solid grasp of these financial metrics, founders can demonstrate their company’s potential for growth and sustainability.

Investor Expectations and Fundraising Diligence

As a startup grows, investor expectations change. Founders should be prepared to adapt to these changing expectations and provide the necessary financial information to support their fundraising efforts. Sasha shares his experience of nearly losing a term sheet due to an unprepared data room. He emphasizes the importance of financial organization and compliance in influencing investor confidence and startup valuations. By being prepared and transparent, founders can build trust with investors and increase their chances of securing funding.

Why VCs Don’t Expect Perfection

Sasha stresses that VCs don’t expect perfection from startups. Instead, they want founders to be honest about what’s working and what’s not. By acknowledging areas for improvement, founders can create a stronger pitch and build trust with investors. This approach also allows founders to focus on their strengths and showcase their company’s potential for growth.

Building Puzzle and the Future of Accounting

Sasha’s own fundraising and finance frustrations ultimately led him to build Puzzle. He aims to revolutionize the way startups manage accounting and understand their financial health. By leveraging AI and machine learning, Puzzle can provide founders with accurate and timely financial insights, enabling them to make data-driven decisions and secure funding with confidence.

Conclusion

In conclusion, understanding the financial reality of your business is crucial for securing funding. By being aware of key financial metrics, adapting to changing investor expectations, and being transparent about areas for improvement, founders can raise funds with more confidence and leverage. With the right approach and tools, startups can overcome common fundraising challenges and achieve their growth potential.

TravelSpots AI

Online Assistant

Hello! I am **TravelSpotsDaily**'s virtual assistant. Do you need any recommendations for travel destinations, food, or itineraries today? 😊
Explore Locations

Map & Regional Filter

Filter by Region