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Lessons from 350 Angel Investments & New $26M Fund

Fundraising
June 5, 2025
Immad Akhund reveals startup insights and future of venture capital.
Topics discussed in the episode:
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How did Emad secure investment from top-tier VC firms like Sequoia?
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How can setting clear hiring criteria based on culture improve team quality?
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How did Mercury acquire its initial customers?
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How can founders leverage AI tools like ChatGPT in their workflow?
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How should founders approach raising funds during hype cycles, especially in AI?
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Why prefer serial founders with a chip on their shoulder?
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Should startups focus on competitors or customers when building products?
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How will AI impact engineering team sizes in startups?
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Why is it important to define company culture early?
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Should founders prioritize raising funds at the highest valuation?

How did Emad secure investment from top-tier VC firms like Sequoia?

Opening: Landing top VC investors can significantly impact a startup's trajectory. Emad shares his experience with securing Sequoia as an investor. Quote:

\"Sequoia does not take their position lightly. Like they did the most work... they did the most diligence with customers... they ask really good questions and I like that.\"

Takeaway:
  • Demonstrating strong business fundamentals attracts top investors.
  • Be prepared for in-depth diligence; thorough preparation is key.
  • Top VCs value founders who appreciate rigorous evaluation and feedback.

How can setting clear hiring criteria based on culture improve team quality?

Opening: Hiring is crucial for startup success. Emad discusses the importance of adhering to cultural values in hiring decisions. Quote:

\"We had these six attributes and we came up with interview questions against them and we've always encouraged them internally... we've built this really strong cohesive culture.\"

Takeaway:
  • Defining specific cultural attributes helps in making consistent hiring choices.
  • Tailoring interview questions to these attributes ensures alignment with company values.
  • A strong culture can scale effectively as the company grows.

How did Mercury acquire its initial customers?

Opening: Early customer acquisition is vital for startups. Emad explains how his investing activities helped Mercury gain its first users. Quote:

\"I have always done that, like even before I started Mercury, I was an active investor... from the first 30 kind of alpha customers of Mercury, I think 100% of them were companies I'd invested in.\"

Takeaway:
  • Leveraging personal networks can jumpstart customer acquisition.
  • Building relationships through investing or advising can benefit product adoption.
  • Founders should consider how their activities can synergize with their startup's growth.

How can founders leverage AI tools like ChatGPT in their workflow?

Opening: AI tools can enhance productivity for founders. Emad shares how he uses ChatGPT in his daily tasks. Quote:

\"I use ChatGPT for everything. I was just doing a presentation yesterday and I basically just talked to ChatGPT for like 30 minutes about the presentation... it just did it for me.\"

Takeaway:
  • AI tools can streamline tasks like content creation and brainstorming.
  • Founders can save time and focus on strategic activities by utilizing such tools.
  • Experimenting with AI can uncover new efficiencies in workflows.

How should founders approach raising funds during hype cycles, especially in AI?

Opening: With AI being overhyped, fundraising becomes challenging. Emad discusses his cautious approach to investing in AI startups during hype cycles. Quote:

\"Seed stage, it's so hard to do AI. I mean, I don't know what you're seeing, but it's like the fourth time I've heard the pitch of the same idea. The founders raising it like a 40 million valuation.\"

Takeaway:
  • Founders should be aware of market saturation and investor skepticism during hype cycles.
  • Differentiation and realistic valuations are crucial to attract investment.
  • Investors may be more selective, so founders need strong fundamentals beyond hype.

Why prefer serial founders with a chip on their shoulder?

Opening: When investing, choosing founders is crucial. Emad explains why he favors serial entrepreneurs who still have something to prove. Quote:

\"I just prefer serial founders; like I have such a bias towards them. A serial founder with a chip on the shoulder... They know how hard it's gonna be, but they're willing to do it again.\"

Takeaway:
  • Serial founders bring experience and resilience to startups.
  • Having a 'chip on the shoulder' indicates motivation and drive.
  • Investors may find these founders more likely to succeed due to their determination.

Should startups focus on competitors or customers when building products?

Opening: In competitive markets, founders may struggle with where to focus their attention. Emad shares his approach on prioritizing customers over competitors. Quote:

\"It's really dangerous to be very competitor focused. I don't let our team speak about competitors very much. I'm just like, hey, if you have something you want to do, tell me why the customer wants it.\"

Takeaway:
  • Emad emphasizes focusing on customer needs rather than competitor actions.
  • Discourages copying competitors; instead, innovate based on customer feedback.
  • Prioritizing customers leads to building better products and long-term success.

How will AI impact engineering team sizes in startups?

Opening: With AI increasing productivity, founders may wonder about future team sizes. Emad shares his perspective on engineering teams amid AI advancements. Quote:

\"To me, if my engineers get more productive, I'm gonna come up with more things to do. Like I have infinite ambitions, so I think that just unlocks more rather than means that you don't hire people.\"

Takeaway:
  • Emad expects to maintain or increase team size due to expanded ambitions enabled by AI.
  • AI productivity gains can lead to pursuing more projects, not necessarily reducing staff.
  • Founders should consider how AI can enhance, not just replace, their teams.

Why is it important to define company culture early?

Opening: Building a strong team starts with a clear company culture. Emad emphasizes the significance of establishing core cultural values from the outset. Quote:

\"First thing when there's like 3 or 4 people, write down what is your company culture. We wrote down like 6 attributes and these things have to be like things that have some trade-offs to them.\"

Takeaway:
  • Early definition of culture guides hiring decisions and maintains team cohesion.
  • Identifying cultural attributes with trade-offs helps in making consistent choices.
  • Embedding culture early ensures it scales as the company grows.

Should founders prioritize raising funds at the highest valuation?

Opening: Fundraising can be challenging, and founders often grapple with decisions around valuation. Emad shares his experience on taking high valuations during fundraising. Quote:

\"I think it is very hard as an entrepreneur not to chase the highest valuation. You know, we did our Series B at 120X which was not rational, this is 2021, but we did it, and I would do it again.\"

Takeaway:
  • Emad believes raising at high valuations is acceptable if you raise enough money to grow into it.
  • Founders should ensure they don't overspend after raising large amounts.
  • Taking higher valuations can be part of strategic growth, even if metrics don't fully justify it at the time.