Breaking Barriers’ Investor Panel: The Path to Success—Founders’ Biggest Wins and Hardest Lessons

Starting a business is never easy, and for founders looking to navigate the complex world of investment, understanding what investors are looking for can make all the difference. That is why we present the key takeaways from our recent conference, “Breaking Barriers: Female Founders and The Emotional Side of Venture Investing. On Day 1 of our conference, we had the privilege of hearing from a dynamic panel of investors who shared invaluable insights on what sets successful founders apart, the common red flags they look for, and how to approach the fundraising process strategically.

Nassim Sayani, an experienced investor, provided a clear breakdown of the qualities she values in founders.

According to Sayani, successful founders share several key traits:

• Hustle and Grit: The ability to keep pushing forward, even when the going gets tough.
• Commitment: Founders who demonstrate deep commitment to their mission and vision are more likely to succeed.
• Critical Thinking: Founders who can think on their feet, adapt to changing circumstances, and solve problems creatively.
• Founder-Market Fit: A deep understanding of the market they are entering and a passion for solving problems within it.

However, Sayani also pointed out some red flags that investors often see as warning signs:

• Hubris: Overconfidence that borders on arrogance can be detrimental, especially when it leads to ignoring feedback or market realities.
• Inability to Take Feedback: Founders who don’t listen to advice or adapt based on constructive criticism can quickly lose investor confidence.
• Lack of Transparency: Investors need to trust the founders they back, and transparency is key to building that trust.

Kelly Ann Wingert, another panelist, added that what founders spend money on during fundraising is a critical factor. She also emphasized the importance of a founder’s ability to pivot when necessary, noting that adaptability is a huge asset for early-stage companies.

The discussion took a thought-provoking turn when the panelists tackled the topic of gender bias in fundraising. Divya Reddy, who has worked extensively with both male and female founders, shared her insights on the subtle—but impactful—differences in how male and female entrepreneurs are perceived during pitches.

Female founders, according to the study Reddy cited, are often asked more “prevention-focused” questions—concerns about risks, potential failures, and what could go wrong—while male founders tend to face more “promotion-focused” questions that center on the opportunities, growth potential, and future success. This disparity in questioning reflects broader biases in how men and women are viewed as business leaders.

To overcome these biases, our panelists suggested three key strategies:

1. Create a Question and Response Framework: Anticipate the prevention-focused questions and craft responses that reframe them in a positive, promotion-focused light. This allows founders to steer the conversation toward their strengths and vision, rather than getting bogged down by doubts.
2. Start with a Big Vision: Women, in particular, may be conditioned to think in terms of scarcity and risks. Instead, begin your pitch by painting a bold, inspiring vision of the future. When you start with an aspirational and abundant view, it sets a confident tone for the rest of the conversation. Sayani reinforced this point by advising founders, particularly women, to adjust their framing. “Don’t say ‘help me,'” she advised. “Instead, say, ‘I’m onto something big, and I’d love for you to be part of it.’”
3. Focus on Financial Benefits in Storytelling
   When sharing your story, it’s crucial to highlight the financial benefits of your product or service and how it will generate value for investors. Start with the numbers—how the business will deliver returns—and then move on to the problem your product solves. This approach signals to investors that you understand their priorities.

The panel also delved into practical strategies for raising capital at the early stages of a startup. They discussed a range of funding options, including:

• Friends and Family Rounds: Often the first place many founders turn, but one that requires careful thought and clear communication.
• Angel Investors: Individual investors who are willing to take early risks, often in exchange for equity.
• Non-Dilutive Funding: Grants, pitch competitions, and other opportunities that allow founders to raise capital without giving up ownership or control.

While traditional venture capital (VC) is often top-of-mind, the panelists stressed the importance of networking and leveraging existing relationships. Alternative funding options, such as crowdfunding and revenue-based financing, are becoming more popular and offer different ways for founders to raise capital without the strings attached to traditional VC.

When is the right time to seek funding? Nassim Sayani provided insight into how the timing of a funding round can depend on factors like your business sector and your capital requirements. It’s crucial for founders to understand the economics of funding and be strategic about when they approach investors. This involves knowing how much capital you need, how it will be deployed, and whether your company is ready for that kind of investment. 

Sayani also warned against rushing into fundraising too early. Founders should have a clear plan and business model in place, demonstrating that they can use capital effectively and scale.

Kelly Ann Wingert shared her perspective on investing in dividend-type businesses, where investors receive returns through profit-sharing or revenue-based financing. This model is particularly appealing to investors who are looking for a more predictable, ongoing return on their investment.

Marcia Dawood, the panel’s moderator, recommended looking into Sage Growth Capital, an investment fund in Idaho that focuses on revenue-based funding, where investors are paid back through the revenue generated by the business. This model, according to Dawood, is gaining traction as it provides flexibility for founders and more aligned incentives for investors.

The Day 1 Investor Panel provided valuable insights for founders looking to navigate the complex world of fundraising. Whether you’re pitching to VCs or exploring alternative funding sources, understanding what investors want—grit, commitment, and a bold vision—is key to success. By developing a strategic approach to pitching, addressing gender biases, and exploring creative funding options, founders can significantly improve their chances of securing the capital they need to grow their businesses.

The journey to success isn’t easy, but with the right strategies, tools, and mindset, founders can confidently take the next steps toward turning their big ideas into reality.

Victoria Yampolsky is a serial entrepreneur, strategic CFO advisor for numerous early-stage start-ups and expert in financial modeling and valuation. She’s a passionate advocate for female founders and fair access to capital for all.

As the President and Founder of The Startup Station, a strategic CFO advisory firm and financial education platform for startups and small businesses, she has collaborated with over 150 founders across 15 industries, assisting them in raising more than $50M in venture capital funding. Hundreds of entrepreneurs worldwide took The Startup Station’s courses on accounting, financial modeling, valuation and startup finance.

Victoria founded PowerUp Globally, a non-profit program that helps seed-level female-led ventures grow and secure their next round of funding through sales and financial training. The program aims to close the gender funding gap. PowerUp also offers the Female Founder Mindset Gym, a resilience-building program for early-stage female founders.

Before venturing into entrepreneurship, Victoria spent nearly a decade on Wall Street in Deutsche Bank Research and IT Consulting at CapGemini.

Victoria holds a Bachelor’s Degree, Cum Laude, in Computer Science, with a minor in Mathematics from Cornell University, and an MBA, with honors, from Columbia Business School.