Gary Stewart is the Managing Director of the Techstars New York City Accelerator powered by J.P. Morgan. Born in Jamaica, he grew up in the Bronx, where he attended the Bronx High School of Science before attending Yale College and Yale Law School. He is a VC-backed, exited serial entrepreneur; an early-stage investor that managed a $1.6 billion start-up portfolio; a professor who has taught entrepreneurship at Yale Law School and IE Business School in Madrid, and been invited to speak at Cambridge, Oxford, Stanford and INSEAD; and a former contributor to Forbes Magazine. As someone who has seen firsthand that talent is distributed evenly but opportunity is not, he is passionate about ensuring that underrepresented and overlooked founders get access to the social and financial capital that they need and deserve. As an investor, he is particularly interested in companies that aim to change the world with a specific focus on healthcare, health and beauty, edtech and financial inclusion.

01. What are you looking for in startups for the Techstars New York City powered by J.P. Morgan accelerator?

The last few years have challenged all of us, but working with other entrepreneurs gives me a lot of hope. As Steve Jobs once noted: “The people who are crazy enough to think they can change the world are the ones who do.” I love working with the “crazy ones” who aspire to make us all healthier, happier, smarter and wealthier. In this sense, I am particularly excited to work with founders in the healthcare, health and beauty, edtech and financial inclusion spaces. 

Beyond the particular industries, I look for ambitious founders with a clear understanding of and passion for the problem they are trying to solve, relevant domain expertise (i.e., “founder-market fit”), and a compelling thesis of why they are likely to be the category winners in a big, growing, multi-billion-dollar market. When I was a first-time entrepreneur, Marc Andreessen’s blog post entitled “The Only Thing That Matters” greatly influenced me. His thesis is simple: The number one start-up killer is lack of market (or relatedly, lack of enough money to buy the time to find your market), so the key for founders is to find “product/market fit” before they run out of cash. In this sense, any examples of early customer validation or “traction” can be particularly persuasive.

02. What are some of the biggest learnings from your career and entrepreneurial journey that you bring to being a Techstars Managing Director?

There are 3 major lessons I’d share.

First, your network is your net worth. Who you know still matters at least as much as what you know. This is a particular disadvantage for those of us who start life belonging to the “wrong” race, ethnicity, gender, sexual orientation, geography or socio-economic status, among other categories. Networking shouldn’t be seen as a dirty word, but rather as an effective and essential tool to opening up closed doors. Founders should use platforms like Techstars to expand their networks and to build lifelong relationships that often mean the difference between success and failure. If no one is willing to speak up on your behalf when competitive opportunities present themselves behind closed doors, the prize will more likely go to the person who had more effective and effusive sponsors. 

Secondly and relatedly, leverage allies who want to see you succeed and might have the resources and networks to make it happen. I am an immigrant. I am a gay man. And I grew up in the Bronx. But I went to Yale twice and I’ve since traveled the world having visited 64 countries and lived and worked at the highest levels in the UK and Spain. I’ve even become friendly with members of the British Royal Family. But I wouldn’t have achieved any of it without strong and supportive mentors, champions and allies, most of whom look nothing like me. When I was growing up, my Auntie Joy would constantly remind me: “Always remember that you’re as good as any, better than many, and inferior to none.” They say the best way to make God laugh is to tell him your plans; imagine if he saw your business plan. Success requires you to have the confidence to embrace new, often unexpected opportunities, including being willing to meet, give the benefit of the doubt to and accept the support of people that might not appear to have anything in common with you. 

Finally, being a founder is tough, probably one of the toughest things I’ve ever done. It is an iterative process in which repeated failure is often a precondition to success. In this volatile environment, your self-worth cannot be tied to whether you’ve raised a funding round or hit your lofty KPIs. What you do is not who you are. Have a good network of family and friends who will remind you of who you are and keep you grounded and stable, even as you jump headfirst into the entrepreneurial abyss. They will be your safety net, both mentally and sometimes financially. Make especially sure that your closest loved ones (e.g., partners and spouses) are fully bought in, as you don’t want them to become collateral damage to your entrepreneurial dreams.

03. What is your favorite thing about the New York City startup scene?

Founders need access to capital and networks to succeed, and they need to be in an ecosystem that welcomes them, even if they don’t look like Leonardo DiCaprio in The Great Gatsby. In that sense, there are few cities in the world that can compete with NYC.

Firstly, there’s a lot of money for start-ups in NYC. VC-backed start-ups in the NYC metropolitan area raised more than $52 billion in 2021, more than 2x the $20.2 billion raised in 2020. 8.4% of all VC funding raised globally in 2021 went to NYC-based start-ups, making NYC the second-most prosperous region for venture funding globally. 

But VC funding is only one part of the story. Especially in the current economic climate, access to customers is arguably as important as access to VCs, and NYC has few peers in this regard. NYC’s $1.4 trillion GDP makes it the world’s second richest city, and it is expected to become number 1 by 2035, when its GDP is expected to reach $2.5 trillion. Home to the world’s largest central business district, NYC hosts a $458 billion financial services sector and a $140 billion education and healthcare sector, all verticals on which this program will focus.

Finally, NYC is one of the most diverse cities not just in the US (more than 50% of its residents are racial and ethnic minorities) but in the world (almost 38% of its population are immigrants with as many as 800 different languages or dialects spoken in the city, making it the most linguistically diverse city in the world). And as the city that never sleeps, America’s cultural capital is, by far, its most visited city with incomparable world-class theaters, restaurants, etc.

In short, NYC provides access to money, networks and culture in a way that is potentially both inclusive and abundant. Few start-up scenes in the world can compete with that winning combination.  

04. What does our partner J.P. Morgan bring to the accelerator?

Startups face challenges at every stage. However, financial challenges can abruptly end a startup’s vision for their product, team, or growth. J.P. Morgan has the expertise, financial solutions, and network to support the disruptors of today and leaders of tomorrow. This program represents Techstars and J.P. Morgan’s belief that diversity and inclusion are the catalysts of innovation and growth. In supporting early-stage startups, J.P. Morgan believes it can help build a future with stronger companies led by underrepresented, diverse founders.

For J.P. Morgan, it’s about changing the entire ecosystem because while talent is distributed equally, opportunity is not. Backing diverse founders leads to a reinvestment in their communities and expanding access for others. J.P. Morgan has made longstanding, large-scale investments in cities to support local initiatives, entrepreneurs, and the environment with over $30 billion committed to advancing racial equity in 2020 and $2.5 trillion towards green initiatives by 2030.

J.P. Morgan’s partnership with Techstars shows their commitment to supporting inclusive accelerators that create opportunities for diverse, early-stage founders. As a part of this partnership, J.P. Morgan will offer an integrated suite of services to founders in this accelerator that extend beyond the 13-week program. This includes, but is not limited to, access to banking, wealth management, and advisory solutions accessible through their local and commercial banking specialists.

05 - Why is growing diversity in entrepreneurship important to you?

I know what it’s like to be overlooked and underestimated, and I’ve written about it various times as part of my Forbes column. I don’t think it’s fair to be expected to work twice as hard for half as much, and I want to make sure that we erase that as an accepted status quo expectation for women, people of color and other overlooked communities. In a capitalist system, wealth is the currency of social change. Entrepreneurship is the key to creating intergenerational wealth for communities that have been systematically locked out of wealth creation. And though much of the focus has often been on race and gender in the US, for me, it’s much bigger than that. It is not sustainable that 99% of the world continues to have their problems ignored and their entrepreneurial aspirations suffocated simply because of who they are, who their parents are or where they live, particularly when we know that diverse organizations perform better. We can see the frustration of shattered dreams reflected in various movements, from the rise of populist leaders to the BLM and MeToo movements to the events of January 6th. Entrepreneurship allows us to offer solutions to the very real problems faced by underserved and left-behind communities while also generating the wealth that funds and feeds long-term social change.

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