Kai Bond

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

I am a 3x founder, so I approach VC through that lens.  It shaped who I am and how I invest.  I never thought I would be in venture, but I was given the unique opportunity to be the General Manager of 2 different accelerator programs.  I absolutely love the excitement of early stage companies and when given the chance to share my knowledge, coach, mentor, and advise founders - it is incredibly rewarding and fulfilling.  My first job in venture was at Catalyst Fund - deploying capital to underrepresented founders.  When I was able to combine mentorship with capital, it was immediately  clear that I wanted to dedicate the next chapter of my career to investing.  I was incredibly fortunate to co-invest with Courtside Ventures on several deals over the years and was lucky to join the partnership in 2019.
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Investment Approach: What are the key factors you consider when evaluating a founding team?

Perseverance - there will be a ton of adversity, challenges, and unexpected issues along the way.   Passion - borderline unhealthy obsession with their product or business.  Coachability - they treat themselves like their product...striving to be better Team Dynamic - being co-founders is like being married.  I started a company with my partner 3x.  We trusted one another and always fought for the right outcome...I look for the same, you have to be able to lose the ego and make sure that everything is about the core of the business.  It doesn't matter where the right answer comes from, but that should make it to the top.
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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?

It varies dramatically.  First, I stay out the way.  Whatever that founder is best at, let them do it and stay out of the way.  Whatever they hate, throw it my way.  Given I have been an operator for years, I will assist with legal, operations, sales, hiring, product, or pretty much any area of the business.  But it is a two way conversation with the founding team on how to best use my skill and expertise that can advance the company mission.  But mainly, being a founder is lonely.  It’s hard.  It’s confusing.  It’s taxing.  Sometimes, you just have to listen and be there.  It’s the late night phone calls or weekend texts during the hard times that are inevitably the most helpful things for most CEOs.  No one likes to admit it, but it is not easy to lead a team and try to live a normal life.  You need to be one of the folks on speed dial for any issue.
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If I'm coming to pitch to you or your firm, what's the one piece of advice you'd give me?

Come as you are.  We are looking to learn from you - you are the expert and we are here for the ride.  The most important element is educating us.
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How would you describe your own personal mission and values, and how do they impact the way you invest?

Starting a company is the truest expression of oneself.  I want to see your heart and soul in this mission you are on.
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What do you like best about investing in NYC, and what’s your outlook on the future of NYC tech?

New York is about the people that are here.  Every walk of life - race, ethnicity, gender, and culture.  Every industry - finance, advertising, tech, film, art, gaming, and media.  It is the most unique amalgamation of raw talent and progressive perspective on the planet.   New Yorkers are tough - we are resilient.  The founders who stay here and follow their dreams in the coming years will absolutely be the category defining companies of our time.