Q&A With Jenny DaSilva of Start Small Think Big

Q&A With Jenny DaSilva of Start Small Think Big

Jenny DaSilva is the founder and Executive Director of Start Small Think Big (Start Small), a non-profit organization that helps low- and moderate-income individuals in New York City start, sustain and grow their small businesses by offering free legal services and financial management training. Recently, Debevoise Pro Bono Counsel Jennifer Cowan sat down with Jenny to discuss Jenny’s background, Start Small’s mission, and the challenges that low-income individuals, especially women, face when starting small businesses.

Q: Tell us about your background.

Well, as you know, I am a lawyer. I spent the first year of my career at Debevoise as a corporate lawyer. Then, my husband got a job at the International Criminal Tribunal for the Former Yugoslavia (ICTY) in The Hague in the Netherlands, and while living there, I worked for a microfinance organization. This was during the financial crisis, and as the economy imploded, I started thinking about microfinance as a way of helping lower income people in the United States build small businesses.

It occurred to me that most people focus on small business development from a finance angle and the idea that small businesses need money. I wasn’t aware of an organization focused on the other issues that businesses face—like legal and financial management support, i.e., the key infrastructure that a business needs to succeed. That’s the mission behind Start Small Think Big—to help people start businesses by giving them the technical assistance to grow their businesses in a safe and responsible way. We aim to help them protect what they own and really develop independent assets with which they can support themselves and their families.

Q: Did you have small business experience when you started Start Small?

Not at all, I had a background in non-profit programs! When I started Start Small, I anticipated it being a not-for-profit organization, but I quickly became acutely aware of the fact that I was running a business in addition to running a non-profit. And that was a very important realization for me, because it helped me appreciate how focused our clients need to be. The decisions that I need to make as executive director are the same ones that our clients are making. We ourselves are the same start-up lean, mean machine that our clients need to be, and I think our clients appreciate that about us. They see how closely we’re aligned with the work that they themselves are doing, and they see that we have the same challenges too. We have capital challenges; we need to constantly develop and hone our product. Sustainability is an issue; it’s so easy to be pulled into so many directions. We have to be laser-focused on what we want to do and cut out what doesn’t work. Everybody needs to be on the same page, and not distracted by the “what-ifs.” It’s a lot of troop rallying and constant vigilance.

Q: Tell us more about Start Small. How has your mission developed?

We are turning seven years old and we’ve grown dramatically in that short period of time. I started with all zeros—zero people, zero dollars, zero clients. We’re now nine full-time employees and one part-time employee. Our budget this year is just shy of $800,000. We currently work with about 1,000 entrepreneurs a year, providing legal and financial management services, and we’re developing a market access program as well, so that our clients will have the tools to grow a market—customers—for their products.

Since we started, our goal has been to help businesses operating at early stages to grow. Initially, we only provided legal services, and we realized very quickly that we can’t provide those services in a vacuum. Legal advice is irrelevant unless the financial management is strong.

This is something that women particularly need help with because there’s very little capital available for small business owners and women business owners attract a minuscule percentage of that capital—something like 5%. Because of that gap, the margin of error for low-income female entrepreneurs is essentially zero. They have no financial cushion to absorb mistakes. Our clients—75% of them women—come to us underfunded, and that’s where we come in: our role is to create a safe space for our clients to grow their businesses in the same way businesses with equity capital are able to grow. The financial management aspects of running a small business are critical. But money isn’t the only thing people need. We’ve recognized that managing money and having in place the legal infrastructure to protect what you build are the two main challenges for starting a small business in the United States. For many small businesses, the rules and regulations, licenses and taxes are expensive and complicated. People with limited money are going to be particularly impacted by that. Our clients are bootstrapping their businesses—surviving on sheer resourcefulness and ingenuity—and we aim to give them the support and resources to really do this all.

Q: You mentioned that 75% of your clients are women. Can you give us a picture of who your clients are?

We’ve been very purposeful in who we work with and who we want to help grow. We work with people who have clear ideas for their businesses and how they want them to grow, but who need the types of support we offer. About 95% of our clients are people of color and women, 40% of our clients are immigrants, and 30% are living below the poverty line when they start their businesses. It’s always hard to start a small business, but it’s particularly challenging from that financial level.

After their first year of operation, 95% of our businesses are still operating, which is about on par with industry average, but we think that represents a statistically better outcome because the industry average includes much bigger businesses. In the last two years, our businesses have employed almost 700 people and generated almost $9 million in revenue.

It’s hard; so much is weighted against them. These are people working uphill. When you look at the statistics, the odds of starting a successful small business are small, and our clients are incredibly dedicated and passionate. They are going to work to get it done.

For our clients, there’s always a story and a history to their businesses and that helps them persevere against the odds. One client had a lung transplant and while she was in the hospital, she felt ugly. She couldn’t get her hair done, couldn’t get her nails done, so she’s started a business that gives manicures/pedicures to homebound and hospitalized people. So many clients have stories like that. Another client’s mother died of cancer. She had been given two years to live, but she ended up living for eight years. When she was ill, she began doing yoga and meditation, and her son (our client) attributes her longevity to that change in lifestyle, so he created his business: a mobile yoga and meditation service that he brings to people who wouldn’t otherwise have the opportunities to get out of their house and go to a studio.

Q: Does Start Small have any particular challenges?

We can’t be everything to everyone. We know that our clients face difficult issues outside of their businesses, and yet we know we need to remain focused on the things we can really help with. For example, if clients come to us with really, truly pressing housing or domestic violence problems, then we’re not really the people they need currently. These are some of the hardest issues that we deal with, and the hardest conversations we have with clients. Sometimes putting a business on pause is what needs to happen. We try to connect them with services to address their immediate problems and encourage them to come back to us when their lives have stabilized.

Q. Where do you see Start Small going next?

Small businesses have a million needs, not just legal needs. Coming from my perspective as a lawyer, we started with essentially a pro bono legal program. When we started the financial program, it was a shock to realize that it’s harder to galvanize a pro bono movement in industries other than law, and that’s become a whole other mission. For me, the legal community is the gold standard for how people in every industry should be doing pro bono work. And I’m hoping to mobilize volunteer efforts in other industries to provide pro bono work in the same way and up to the same standards as the legal community to help our clients grow their businesses.


Jennifer Cowan is a counsel in Debevoise’s New York office, and manages the firm’s pro bono program.

Comments? Suggestions? We’d love to hear from you. Send us an email at women@debevoise.com.



Q&A With Jenny DaSilva of Start Small Think Big

Q&A With Jenny DaSilva of Start Small Think Big

Q&A With Jenny DaSilva of Start Small Think Big

Jenny DaSilva is the founder and Executive Director of Start Small Think Big (Start Small), a non-profit organization that helps low- and moderate-income individuals in New York City start, sustain and grow their small businesses by offering free legal services and financial management training. Recently, Debevoise Pro Bono Counsel Jennifer Cowan sat down with Jenny to discuss Jenny’s background, Start Small’s mission, and the challenges that low-income individuals, especially women, face when starting small businesses.

Q: Tell us about your background.

Well, as you know, I am a lawyer. I spent the first year of my career at Debevoise as a corporate lawyer. Then, my husband got a job at the International Criminal Tribunal for the Former Yugoslavia (ICTY) in The Hague in the Netherlands, and while living there, I worked for a microfinance organization. This was during the financial crisis, and as the economy imploded, I started thinking about microfinance as a way of helping lower income people in the United States build small businesses.

It occurred to me that most people focus on small business development from a finance angle and the idea that small businesses need money. I wasn’t aware of an organization focused on the other issues that businesses face—like legal and financial management support, i.e., the key infrastructure that a business needs to succeed. That’s the mission behind Start Small Think Big—to help people start businesses by giving them the technical assistance to grow their businesses in a safe and responsible way. We aim to help them protect what they own and really develop independent assets with which they can support themselves and their families.

Q: Did you have small business experience when you started Start Small?

Not at all, I had a background in non-profit programs! When I started Start Small, I anticipated it being a not-for-profit organization, but I quickly became acutely aware of the fact that I was running a business in addition to running a non-profit. And that was a very important realization for me, because it helped me appreciate how focused our clients need to be. The decisions that I need to make as executive director are the same ones that our clients are making. We ourselves are the same start-up lean, mean machine that our clients need to be, and I think our clients appreciate that about us. They see how closely we’re aligned with the work that they themselves are doing, and they see that we have the same challenges too. We have capital challenges; we need to constantly develop and hone our product. Sustainability is an issue; it’s so easy to be pulled into so many directions. We have to be laser-focused on what we want to do and cut out what doesn’t work. Everybody needs to be on the same page, and not distracted by the “what-ifs.” It’s a lot of troop rallying and constant vigilance.

Q: Tell us more about Start Small. How has your mission developed?

We are turning seven years old and we’ve grown dramatically in that short period of time. I started with all zeros—zero people, zero dollars, zero clients. We’re now nine full-time employees and one part-time employee. Our budget this year is just shy of $800,000. We currently work with about 1,000 entrepreneurs a year, providing legal and financial management services, and we’re developing a market access program as well, so that our clients will have the tools to grow a market—customers—for their products.

Since we started, our goal has been to help businesses operating at early stages to grow. Initially, we only provided legal services, and we realized very quickly that we can’t provide those services in a vacuum. Legal advice is irrelevant unless the financial management is strong.

This is something that women particularly need help with because there’s very little capital available for small business owners and women business owners attract a minuscule percentage of that capital—something like 5%. Because of that gap, the margin of error for low-income female entrepreneurs is essentially zero. They have no financial cushion to absorb mistakes. Our clients—75% of them women—come to us underfunded, and that’s where we come in: our role is to create a safe space for our clients to grow their businesses in the same way businesses with equity capital are able to grow. The financial management aspects of running a small business are critical. But money isn’t the only thing people need. We’ve recognized that managing money and having in place the legal infrastructure to protect what you build are the two main challenges for starting a small business in the United States. For many small businesses, the rules and regulations, licenses and taxes are expensive and complicated. People with limited money are going to be particularly impacted by that. Our clients are bootstrapping their businesses—surviving on sheer resourcefulness and ingenuity—and we aim to give them the support and resources to really do this all.

Q: You mentioned that 75% of your clients are women. Can you give us a picture of who your clients are?

We’ve been very purposeful in who we work with and who we want to help grow. We work with people who have clear ideas for their businesses and how they want them to grow, but who need the types of support we offer. About 95% of our clients are people of color and women, 40% of our clients are immigrants, and 30% are living below the poverty line when they start their businesses. It’s always hard to start a small business, but it’s particularly challenging from that financial level.

After their first year of operation, 95% of our businesses are still operating, which is about on par with industry average, but we think that represents a statistically better outcome because the industry average includes much bigger businesses. In the last two years, our businesses have employed almost 700 people and generated almost $9 million in revenue.

It’s hard; so much is weighted against them. These are people working uphill. When you look at the statistics, the odds of starting a successful small business are small, and our clients are incredibly dedicated and passionate. They are going to work to get it done.

For our clients, there’s always a story and a history to their businesses and that helps them persevere against the odds. One client had a lung transplant and while she was in the hospital, she felt ugly. She couldn’t get her hair done, couldn’t get her nails done, so she’s started a business that gives manicures/pedicures to homebound and hospitalized people. So many clients have stories like that. Another client’s mother died of cancer. She had been given two years to live, but she ended up living for eight years. When she was ill, she began doing yoga and meditation, and her son (our client) attributes her longevity to that change in lifestyle, so he created his business: a mobile yoga and meditation service that he brings to people who wouldn’t otherwise have the opportunities to get out of their house and go to a studio.

Q: Does Start Small have any particular challenges?

We can’t be everything to everyone. We know that our clients face difficult issues outside of their businesses, and yet we know we need to remain focused on the things we can really help with. For example, if clients come to us with really, truly pressing housing or domestic violence problems, then we’re not really the people they need currently. These are some of the hardest issues that we deal with, and the hardest conversations we have with clients. Sometimes putting a business on pause is what needs to happen. We try to connect them with services to address their immediate problems and encourage them to come back to us when their lives have stabilized.

Q. Where do you see Start Small going next?

Small businesses have a million needs, not just legal needs. Coming from my perspective as a lawyer, we started with essentially a pro bono legal program. When we started the financial program, it was a shock to realize that it’s harder to galvanize a pro bono movement in industries other than law, and that’s become a whole other mission. For me, the legal community is the gold standard for how people in every industry should be doing pro bono work. And I’m hoping to mobilize volunteer efforts in other industries to provide pro bono work in the same way and up to the same standards as the legal community to help our clients grow their businesses.


Jennifer Cowan is a counsel in Debevoise’s New York office, and manages the firm’s pro bono program.

Comments? Suggestions? We’d love to hear from you. Send us an email at women@debevoise.com.