Speaker Bio

Charlie O’Donnell is a well-known figure in the NYC startup community, having worked as an early-stage investor for nearly 20 years. He founded Brooklyn Bridge Ventures in 2012 and has helped source investments for notable companies such as GroupMe, SinglePlatform, Moat, and Backupify. His fund has made nearly 100 investments since its founding, making it one of the most active pre-seed and seed round investors in the city. Charlie has also been recognized as one of the 100 Most Influential People in NY Tech five times by Business Insider and is an active member of the NYC entrepreneurship and technology scene.

Top 3 Takeaways

1. Aligning with your investors on your company’s vision is crucial, as conflicting views can hinder growth. [Investors]

• Ensure that each investor in your cap table aligns with your team’s vision. Ask them about their investment thesis, portfolio companies, and industry expertise, and discuss your product vision and go-to-market strategy with them to identify any misalignments. Having investors who do not align with your vision can lead to conflicts and potentially hinder your company’s growth.
• Choose wisely when deciding who will have influence and power over your company. Aside from their investment, investors can bring valuable insight into hiring, understanding the market, or strategy.

2. Focus on your core competencies and delegate tasks outside your expertise to others in order to scale your business effectively. [Scaling]

• As a founder, focus on fortifying your strengths and filling in your weaknesses. No one can do it all, and in order to scale, the best founders strategize to build their personal core competencies and co-found, hire, or outsource for the additional positions on their teams.
• As Charlie O’Donnell advises, don’t expect yourself to be an expert in every area – play to your strengths and delegate tasks that fall outside your expertise. For example, if you’re a machine learning expert, focus on using your skills to develop your product and hire a Google Ads specialist to handle your marketing campaigns.

3. Approach negative feedback with an open mind and evaluate it holistically, as it may point out areas for improvement. [Product Development]

• Assume negative feedback has truth and try to evaluate it holistically. Rather than rejecting feedback outright, take a step back and see the perspective of the giver of the feedback. If it applies, then use it to improve the product. If it doesn’t apply, then you can move forward understanding how and why it doesn’t apply.
• It’s easy to become defensive when receiving negative feedback, but Charlie O’Donnell advises founders to approach feedback with an open mind and try to understand where the feedback is coming from. Sometimes, negative feedback can point out real areas for improvement, so it’s important to consider it carefully before dismissing it outright.

Interview Highlights

I. Investor Questions

Q: What type of companies do you invest in?

As a generalist investor, I look for companies that meet certain criteria. Firstly, I prefer to invest in startups that have less than 750K in funding as I like to be involved from the beginning of their journey. This is because it becomes increasingly difficult to invest in companies that have already raised more capital, as more diligence is required to analyze the data that comes with more funding.

Secondly, I focus on investing in companies based in NYC as it’s an area I’m familiar with and can easily visit. I like to invest in companies that I can bike to, or at the very least, take the train to New Jersey and bike back.

Lastly, I invest in companies that are easy to understand or have a validated, strong customer base, even if they operate with complex technology. It’s important to me that I can grasp the product or service a company is offering and see the potential for its success.

Q: What value do you bring to the cap table?

As an investor, I offer direct and honest feedback to startups and have frank conversations about the reality of the company. I can help with narrative creation, reviewing pitch decks and identifying areas that need improvement. Additionally, I am always happy to leverage my network to support the growth of the companies I invest in.

Q: [Audience Question] How can I capture the attention of a VC? Is it appropriate to send multiple emails if I don’t get a response or should I stick to one email?

VC’s get a FLOOD of emails! In the words of Charlie: “I give away money for a living…imagine the inbox!” Feel free to send a follow-up email (or several!) if you don’t receive a response the first time, and don’t use overly flowery language. Get directly to the point about what your company does and where you’re headed. Remember to highlight where you’re headed, since this VCs are looking to jump on a ticket for the future as opposed to rewarding the past.

Also, personalize your email! Perhaps mention something they’ve written about or something you like about their team or previous investments. If you’re reaching out for advice, make the question specific and easy to respond to as opposed to asking for general thoughts. If you happen to run into a VC, don’t try to give them your full pitch on the spot, especially if they’re in a rush! Introduce yourself, ask for their email to send your deck over, and follow up over email. This helps to get your name and company known and also ensure they have the time to review the details more closely later on.

II. Founder Advice

Q: What sets great founders apart?

First, they choose their investors carefully! If an investor does not align with the founding team, there is bound to be a lot of friction in the company execution. Life is too short to have someone you can’t agree with on the team!

Second, great founders learn fast! They’re similar to the president, who learns how to navigate Congress, hire great staffers and a great advisory board, and learns a wide range of applicable material.

Finally, great founders have a willingness to ask questions and get help, even when there’s a lot of pressure to know everything. A great founder could have just raised 100 M and will be able to transparently share which parts they don’t know without wasting time pretending they know it. For example, if you’re a great technical engineer and you don’t know how to build a Google Ads campaign, hire or outsource to someone who does! Nobody expects you to know everything – they expect you to know your strengths and find others who can fill in your gaps.

Q: When pitching, how do you balance long-term vision vs short-term profits and day-to-day reality for the company? For example, if you’re pitching Amazon, would you pitch a book marketplace (as AMZN started off as) or the future of Amazon (a global marketplace across products and industries.)

When pitching, it’s important to balance both the current stage and the long-term vision. You should communicate the core mission of the product and relate it to the vision. For example, if you’re pitching Amazon, you could say something like “the business today is just books but the business tomorrow is a global marketplace.” However, even if the company never reaches the final vision, it can still be a successful business. Take OpenTable for example, it still works even with just one restaurant. As the business grows, there are more opportunities for it to expand and become more popular.

Q: What slides are critical for the pitch deck?

A pitch deck should include a brief company overview and a compelling vision statement to showcase the team’s capabilities. It’s important to have a Total Addressable Market (TAM) slide, but it’s not necessary to inflate the TAM to look bigger. Some emerging markets may not have a solid estimate of their size until the product matures. Finally, investors may be interested in markets that don’t exist yet, like Spark (a podcast editing company) or VR/AR, which wasn’t a market when the Oculus was created but has since grown to $2B.

Q: What questions should founders always ask VCs?

Ask VCs two critical questions: how many partners need to approve the deal, and when can you expect a decision? It’s also good practice to inquire about their experience with deals similar to yours.

Q: [Audience Question] I’m a founder at a dating app company, what do you think could help me grab investor attention for my product?

Investors focus on the problem set when considering a potential investment. If they are interested in the dating space, it will be easier to convince them of the value proposition of your app. However, investors may not be open to a specific space, so it’s important to research their portfolio to gauge their interests.

It’s worth noting that it can be challenging for founders who are not white or male to secure funding (source). It’s essential to convey your revenue-generating potential to investors.

In your pitch, make sure to share your 3-year or 7-year target financials to demonstrate your strategic planning and dedication to success. If you don’t mention it, investors won’t assume you’re considering it.

III. Career & Life Advice

Q: If you could tell your younger self one piece of advice, what would you say?

If I could give one piece of advice to my younger self, it would be to focus on building genuine relationships and valuing people for more than just what they can do for me financially. While having check writers can be helpful, it’s important to also understand people’s backgrounds, values, knowledge, and skill sets. By building strong connections with others and understanding their unique strengths, I can create more meaningful opportunities for collaboration and success.

Q: [Audience Question] Should you found after college or after working in industry for some time?

Success stories of college founders are common, as they often have low overhead and can run lean in the early stages of the company. However, it’s critical to know your space, regardless of when you found. Don’t assume you’ll easily solve problems that others have failed to solve in the industry. Take time to understand their stories and the underlying reasons for why the problems exist in the first place. Your peak earning years are later in your career if you found earlier, so even if your startup fails, you’ll meet a lot of people and learn a lot.

Q: [Audience Question] How do you productively approach taking feedback?

Approach negative feedback with an open mind and evaluate it holistically, as it may point out areas for improvement. Founders should approach feedback with an open mind, evaluate it objectively, and consider how it aligns with their goals and vision for the company. If the feedback aligns with the vision, they can use it to improve their product. If it doesn’t align, they can respectfully decline the feedback and explain why it doesn’t work for their company. The key is to approach feedback with a growth mindset and use it as an opportunity to learn and improve.