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.
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What Investors Look for in Founders: Key Qualities & Red Flags
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.
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Gender Biases in Pitching and Fundraising
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:
- 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.
- 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.’”
- 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.
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Funding Options and Strategies for Early-Stage Founders
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.
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Timing and Approach for Seeking Funding
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.
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Alternative Investment Structures and Dividend-Type Businesses
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.
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Final Thoughts
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.
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About Author
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.
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“If you’re raising capital and want to shine when pitching to investors, I highly recommend you choose Victoria Yampolsky and the Startup Station as your resource for high performance results. Victoria is extremely well versed in all aspects of raising capital and the startup landscape. She provides clients with outstanding tools, applicable advice and thoughtful insights to support their fundraising efforts.
“Victoria is a rare find in the startup world. She’s brilliant with startup financial strategies and has this no-nonsense work ethic that proves to deliver results. Victoria worked with a participant of 2020 Startups, a startup founder, and within a couple of months the founder raised capital. Victoria has done several workshops and speaking engagements at 2020 Startups and is always insightful and held in the highest regard by the audience.”
“These workshops are extremely useful for all of us. Victoria is the kind of presenter/professional who inspires confidence. I’d recommend her to any startup trying to figure out how it needs to be organized, capitalized, and operated to have a good business model going forward. She focuses on fundamentals, which, too often, are sorely lacking in our ecosystem, and she knows her stuff backwards and forwards”
“Victoria Yampolsky is THE essential tool for any startup looking to present a viable financial model! If you are a founder who, like me, lacks the business/finance background – YOU NEED HER. If you are looking to show your investors a serious plan for growth and capitalization – YOU NEED HER. Victoria’s thoroughness and dedication will ensure no stone goes unturned in the FOUNDATION of your BUSINESS. And to top it all, she explains everything with such calm & clarity, it is an absolute delight to be working with her.”
Liz Wald has 25+ years’ experience building company operations and mobilizing global teams in emerging, disruptive industries.
Blair Severn is the Chairman and Co-founder of enabling ideas®, a Venture
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.
Irina Sychov is an expert in voice, pitching, and fundraising and the Founder of ANIMA Women, a community supporting women in business. A five-time startup founder, she has extensive experience with family offices in London and Miami. Irina gained recognition for her dynamic presence on the British show X Factor, impressing judges like Simon Cowell, which sharpened her skills in audience engagement and self-marketing—essential tools in the business world.
Marcia Dawood is an early-stage investor who serves on the Securities and Exchange Commission’s Small Business Capital Formation Advisory Committee. She is a venture partner with Mindshift Capital, a member of Golden Seeds, and the chair emeritus of the Angel Capital Association (ACA), a global professional society for angel investors.
Sanford is the Chief Strategy Officer of PowerUp Globally, a strategic and financial planning initiative aimed at revenue-generating seed-level female-led ventures.
Irina Sychov – Founder of Women’s Business Community 
Thierry Vodounou, PMP, is Managing Director & Founder, 
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.
“What I appreciated most about this program was the opportunity to stop during the work day and have an opportunity to reflect. In addition to having access to pre- and post-session materials that were profoundly useful (which I will undoubtedly go back to), being asked to stop, breathe, and process was a gift that carried throughout the day, week, and program. I recommend this program to any female founder or business owner in the midst of building her business.”
“Atending the Power Up Coaching pilot has been an absolute game-changer for me. Victoria and Hamp’s expertise, passion, unwavering support and genuine commitment to empowering women in the entrepreneurial space were evident in every session. Also, what truly made this journey unforgettable were the incredible women I met along the way. Sharing stories, challenges, and dreams with fellow entrepreneurs created a bond that transcended mere networking—it felt like finding a tribe where I truly belonged. It has equipped me with invaluable skills, insights, and a network of like-minded individuals who continue to inspire and support me on my entrepreneurial journey. The lessons learned and the connections made have become pillars of strength in my entrepreneurial journey, guiding me through the highs and lows with gratitude, grace and resilience. I know that the PowerUp Coaching program will always be more than just a program to me—it’s a part of my story, a chapter filled with growth, friendship, and empowerment. I’m immensely grateful to Victoria and Hamp and The Startup Station for helping me realize my potential as a woman entrepreneur.
“As a busy entrepreneur, I was drawn to PowerUp Globally Coaching Program’s focus on cultivating resilience, emotional intelligence, and a growth mindset for managing the inevitable stresses of building a business. From the first session, the small group size allowed a safe, supportive environment to openly discuss challenges. 
“What a valuable experience!
“Victoria really distilled down the financial model to the inputs that need to be discovered in order to determine business viability. Her attention to detail and experience show in taking those inputs and filling out the rest of the model. These are the real numbers that you need for investors.”
“Victoria provided me with great knowledge for the financial projection and reviewed my pitch deck where she provided me with great pointers. She definitely is somebody I count as my inner circle of advisors and recommend her as the go to person for any start up.”
“If you’re raising capital and want to shine when pitching to investors, I highly recommend you choose Victoria Yampolsky and the Startup Station as your resource for high performance results. Victoria is extremely well versed in all aspects of raising capital and the startup landscape. She provides clients with outstanding tools, applicable advice and thoughtful insights to support their fundraising efforts.
“We are a couple of engineers going through lot’s of trials and errors trying to launch our startup so meeting with Victoria was priceless in terms of getting a fresh unbiased perspective on our business model and getting advice on how to move forward.
“I have the greatest appreciation for Victoria’s contribution in analyzing financial trends and developing the monetization strategies for my business. She is not only an experienced financial analyst, but she is also very creative and gave my business many important suggestions. I felt comfortable and willing to reveal information easily, which helped make the valuation process easier. Victoria can see the big picture almost immediately, and at the same time she is a stickler for details. These attributes make her a perfect financial advisor and mentor for entrepreneurs. Further, Victoria, once given a task, is completely dedicated to it. She has a keen ability to process and synthesize information and make the right decisions, and she comes with the highest recommendation.”
“Victoria is an amazing resource that every start-up should have. She is whip smart and diligent. We worked with her on the valuation of our company and she’s been an invaluable resource in refining our assumptions, revenue and expenditure models. If you think you understand the fundamentals of your own business model, talk to Victoria and get ready to learn so much more!”
“I had the pleasure of working with Victoria for building a working financial model for my business. Her expertise and acumen are not only impressive, but her personable nature made her a joy to work with as well. She was able to offer valuable insights and direction as we strategically built out a financial model, utilizing reliable data assumptions that translate to a usable document for my business. The result and end-product proved the value of both the time and monetary investment. I couldn’t recommend her enough as a resource for any entrepreneur looking to build out a financial model, financial roadmap and/or valuation of their enterprise.”
“Victoria Yampolsky came highly recommended by a colleague of mine and I’ve been fortunate to work with her! She completed the valuation and the financial model for our startup, EnergyPoints. Her unique framework for modeling early-stage ventures allowed us to refine our business plan and use strategy and industry standards to credibly formulate assumptions. Victoria is a Columbia Business School grad and CFA, and her company, The Startup Station, has done 100s of valuations and has an impressive track record. She presented her valuation to two national banks with our accountant, and in both scenarios, she was praised by the level of detail that went into her extensive valuation. I can’t recommend her highly enough!”
“Victoria was a key advisor for Predictive People – as an early stage startup we had tons of questions and we needed professional guidance to sort them out. I am really glad we had her by our side to solve them all, ending with a solid business plan and financial projections. I can’t recommend her more, she’s professional, fast, empathetic, and incredibly smart, a true partner for any startup.”
“Victoria is trustworthy, knowledgeable and customer-focused startup strategic CFO. I’ve been impressed since day 1 with the responsiveness, thoroughness and overall professionalism of Victoria. According to the traditional scenario of almost all early stage startups, the founders are involved in all processes of the company formation. So I am no exception without having a financial education, without professional Excel skills – I nevertheless decided to build a financial model on our own. Honestly, it seemed impossible. But in the end, we did it in a total of 3 weeks. I want to express my deepest gratitude for professionalism and incredible talent to motivate all of our team members. Victoria has a unique ability to get into the essence of the business very quickly, to think very flexibly and innovatively – which is very important for our startup.
“I was a student and client of Victoria through The Startup Station and cannot highlight enough how helpful the process was for our company in reaching our first funding milestone and personally for me. Victoria is a fantastic teacher and recommend her financial modelling courses to anyone. We also worked one to one to refine our company model/financial roadmap and Im proud of my newly developed, ninja-level Excel skills. Paraphrasing from someone famous “Clarity trumps confidence any day of the week” and it’s what I feel from working with Victoria.”
“Building a financial model with Victoria and The Start Up Station for a mutual client was an illuminating experience!
“Victoria is a rare find in the startup world. She’s brilliant with startup financial strategies and has this no-nonsense work ethic that proves to deliver results. Victoria worked with a participant of 2020 Startups, a startup founder, and within a couple of months the founder raised capital. Victoria has done several workshops and speaking engagements at 2020 Startups and is always insightful and held in the highest regard by the audience.”
“Victoria and The Startup Station Team were absolute game-changers for Ovaterra. Victoria served as my right-hand CFO through fundraising, M&A, liquidity crises and more — always guiding the ship with calm, detail-oriented and strategic advice. I would recommend her and her team to any Founder or executive who needs a strategic, fractional CFO to guide your business to the next level.”
“Victoria, we raised $1.4M! It’s finally 
“Victoria is one of the smartest, and most talented financial analysts out there. She has created the financial models for 2 of my companies, to which we have raised over $20M using her financials and valuation reports. She is very professional and always makes you prove the assumptions:) She will always be a vital part to my businesses.”
“In business, and especially with startups, getting to a place of clarity around the business and financial models can be challenging even for the most experienced professional. Victoria brings the right mix of business and financial know-how and quickly understands the moving pieces. As such, she’s able to provide an excellent product, a deeper sense of understanding about the project based on its’ needs, and a sense of calm and assurance that the challenges faced will be dealt with in a way that drives growth.”
“I had the pleasure of working closely with Victoria as fractional CFO of our startup. Her expertise in business and financial modeling is truly exceptional. Victoria played a pivotal role in helping our company think through every aspect of our business, and her ability to create a comprehensive model was nothing short of impressive. She not only provided a clear plan for our future but also identified areas where we could improve and grow.
“Victoria Yampolsky is THE essential tool for any startup looking to present a viable financial model! If you are a founder who, like me, lacks the business/finance background – YOU NEED HER. If you are looking to show your investors a serious plan for growth and capitalization – YOU NEED HER. Victoria’s thoroughness and dedication will ensure no stone goes unturned in the FOUNDATION of your BUSINESS. And to top it all, she explains everything with such calm & clarity, it is an absolute delight to be working with her.”