Overeasy Ventures

Benjamin Siegel

Managing Partner

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Notable Investments


Questions & Answers

Origin Story: In a couple sentences, how would you describe your path to becoming an investor?

Experiencing different vantage points, from working at institutional investment firms to founding and starting companies, Overeasy came together to participate and help founders grow their companies.

Investment Approach: What are the key factors you consider when evaluating a founding team?

Track record (have you founded prior companies), Action Plan (do you have a immediate-, near-, medium-, and long-term plan for success), and relationships amongst the founders.

What's your style and approach when it comes to working with founders post-investment? What are the characteristics of founders you've worked well with?

We prefer a healthy relationship with our portfolio companies and lend a hand wherever it is best fit. Our investment committee is comprised of individuals ranging from 25 to 30 years old and come from a diverse range of backgrounds from founders and operators to investors.

If I'm coming to pitch to you or your firm, what's the one piece of advice you'd give me?

Honesty - we would rather hear you have many investors interested but $0 committed, than hearing you're almost fully subscribed only to learn you have raised 1/10 of your round.

As an angel investor, how many deals do you aim to do each year?


How would you describe your own personal mission and values, and how do they impact the way you invest?

Our core principles are focused on integrity, honesty, and work ethic. If the company who is pitching us check those three boxes, we believe the company will succeed. If the economic and pricing model works, then the company will be an enormous success.

What do you like best about investing in NYC, and what’s your outlook on the future of NYC tech?

New York City is, and always will be, the most vibrant and accessible city in the world. In a post covid-19 environment, people crave interpersonal connections and collaboration, and there is no place like New York City for that to be accomplished.