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    • Please join me in welcoming Jennifer DaSilva, Executive Director of Start Small Think Big, for a Cake Panel! A bit about Jennifer: Jennifer is an attorney whose professional background has been in community development. Jennifer began her career in the Bronx in the late 1990s as the Director of the East Side House Settlement Youth Leadership Program, working closely with South Bronx families and community groups, and building partnerships between East Side House and private funders, nonprofit and government institutions, and private businesses. After graduating from law school in 2001, Jennifer clerked on the District of Columbia District Court for the Honorable Gladys Kessler, and worked as a Litigation Associate at Debevoise & Plimpton in New York. Jennifer then worked for the Lawyers’ Committee for Civil Rights Under Law, where she helped to coordinate their 2008 west coast Election Protection effort by opening three national hotline call centers in California, building mobile legal field programs in Nevada and Washington, and recruiting and training 1500+ legal volunteers. Prior to founding Start Small Think Big in 2010, Jennifer worked at Angkor Microfinance Kampuchea, a licensed Cambodian Microfinance Institution in Phnom Penh, Cambodia, where she helped to design a new microinsurance product for the Cambodian market. She is the chair of the San Francisco Economic Development Alliance , a collaborative of 18 non-profit organizations in San Francisco that provide support services to small businesses. Jennifer holds a BA in Political Science from Yale University, and a JD from Cornell Law School.  

      A bit about Start Small Think Big: Start Small is a 501c3 organization founded in 2010. We are headquartered in New York City and have successfully expanded our model to San Francisco and Oakland. We serve 1,100+ entrepreneurs annually. 95 percent of our small businesses are minority- or women-owned (close to 80 percent are women). Most live in 2-person households making less than $30k a year. Without equal access to critical resources, the businesses that we support, and the entrepreneurs behind those efforts, must work doubly hard to build better futures for themselves and their communities. Entrepreneurship results in increased innovation and sustained economic growth for everyone, particularly those most marginalized. By investing in the underserved, we create jobs and value for our society. Our mission is to help under-resourced entrepreneurs create thriving businesses in underserved areas so owners can build wealth for themselves, their families and communities. We do this by activating and engaging a top-tier network of professional volunteers who provide high-quality legal, financial and marketing services, at no cost.

      Welcome Jennifer!

    • First things first, welcome Jennifer! So what inspired you to take the initial steps towards creating Start Small Think Big?

    • I was living in Cambodia in 2008. This was during the financial crisis, and as the economy back home imploded, I started thinking about microfinance as a way of helping people in the U.S. build small businesses. 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, financial management, and marketing 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 and sustainable way. We aim to help them protect what they own and really develop independent assets with which they can support themselves and their families.

    • Since we started, our goal has been to help businesses operating at early stages to grow. Initially, we only provided legal services. Building a sustainable business requires legal assistance, but legal counsel is prohibitively expensive and so the vast majority of low-income startups go without it. Unfortunately, the failure to secure proper legal counsel often hampers and sometimes even ruins nascent businesses that might otherwise thrive. Businesses lacking sound legal infrastructures are more vulnerable to business-related liabilities and less likely to profit from business relationships or to obtain loans, investment, or large contracts. Quickly, however, we realized that we can’t provide legal services in a vacuum. Legal advice is irrelevant unless the financial management is strong – and the business has a strong and diverse market for their product or services. So, we started providing financial management and marketing support for our businesses as well.

    • I love your mission statement: "We help under-resourced entrepreneurs build businesses in underserved areas so owners can increase their personal financial security and stimulate economic activity in their communities." What does the average entrepreneur or small business founder experience? And how does that underscore what services Start Small Think Big provides?

    • Entrepreneurs are definitely some of the gutsiest people you will ever meet. They are survivors! Every entrepreneur has stared disaster in the face, usually more than once. We don’t ever talk enough about that part of the story - but we should, because how you overcome those setbacks determines if and how you grow. The thing is, setbacks, while bruising, do not have to be catastrophic. But, that for many entrepreneurs, that’s exactly what they are. And the odds of mounting a comeback are even slimmer for people in underserved and under-resourced communities. There’s just no margin for error. That bump in the road is the end of the road. And that’s really why I started Start Small, almost 10 years ago. Because I just don’t believe that the routine and inevitable challenges of running a business should be disqualifiers, just because of how much money you have, or who you know.  Start Small really sets entrepreneurs up for success. We are doing this with more than 1100 entrepreneurs every year, coast to coast - in New York and California. By providing critically necessary legal, financial and marketing support, we ensure that all that sweat, hustle and ingenuity shows up directly on their bottom line.

    • Nade Coulibaly-Doucoure, who is an immigrant from the Ivory Coast, started working with us in the summer of 2018. She wanted to build and grow a business - Baly Cleaning Services, Inc. - that her children could run one day. After working for a nonprofit organization, she found that the cleaning that she did on the side could become a successful business that could be more profitable than her career and would allow her to be her own boss. Nade founded her company over three years ago and stresses the importance of taking care of her client's needs and making sure that her employees are taken care of too. She feels very strongly about providing customers with outstanding cleaning service in an environmentally responsible manner and to being completely trustworthy and professional.

      Over the past year we tapped volunteers from two financial services companies to set up systems to manage sales tax payments and to generate timely and accurate financial statements.  We matched her with pro bono attorneys from two law firms and a corporate legal department to work on contracts, employment law, and doing business online. We've also helped her with brand identity and online marketing,

      We were thrilled to find out recently that her annual income has grown by 150% and her profits have gone up by $30K, and she's hired five more employees.

      Another example:

      Janie Deegan started Janie’s Life Changing Baked Goods after struggling with addiction and homelessness in her early 20s.  For Janie, Janie’s was an act of self care. At the time she was trying to reconstruct her life and stay sober.  She had large gaps on her resume and not a whole lot of work experience. She had no idea what sort of career she wanted. She never intended to be a small business owner, had no idea what being an entrepreneur meant. She likes to say that this path chose her.  

      She’s told us that when she first started working with us she felt like she was playing dress up as an entrepreneur.  Her business was very ad hoc and had no legal or financial structure, and this was getting in the way of her business's  growth.

      We helped her with financial management, marketing her bakery and finding new clients, building her brand, and taking some steps to minimize her liabilities and protect her business.

      Janie is a remarkable personal and professional success story, an example of someone who’s overcome great odds to build a successful small business.  The bakery grew and continues to thrive because of Janie's incredible drive and commitment to building a future for herself. Her business has doubled in size each year since 2016 .

    • What are some of the unique challenges and wins of running a bicoastal nonprofit organization and having presences in both Oakland and New York City?

    • Well, given the time difference between our NYC HQ and our Oakland office, the workday starts on New York time and ends on California time. That’s definitely in the challenge category. But, now that we are on both coasts, we are able to support over 1100 entrepreneurs every year. That is awesome. And, the more experience we have, in different locations, the more quickly we are able to learn what works, and what doesn’t – and the better we get at doing our job.

    • Our entrepreneurs are the inspiration for and driving force behind everything we do, pop up included. The minute we lose sight of that, we have failed critically in our mission. This event is so awesome because it puts our entrepreneurs front and center.

      And, expanding our clients’ customer base is very much a part of our mission and business model. For example, each year we work with corporate partners who host pop up markets with our clients to give their employees the chance to support small businesses and gain access to one-of-a-kind products.

    • One of the things that impressed me was your ability to multiple more than 7x the effectiveness of a donation, so that $1 dollar donated translates to $7.50 in services. What would you say are some of your secrets for success and efficiency?

    • We actively seek out feedback – and we move quickly to correct what isn’t working. We don’t get stuck doing things the wrong way because that’s how they’ve been done. Rather, we recognize and accept the role of failure in growth. We as individual people grow when we learn from our failures. We as an organization grow when we learn from our failures. I am very focused on building an organizational culture that isn’t afraid of failure – if we’re going to do it, and it’s going to happen, we want to acknowledge it, embrace it, do it quickly, learn from it, and move on. It’s not something to be ashamed about, or get upset about. The more we can learn from these experiences, the more quickly we can grow – and ultimately succeed.

    • If someone is starting out as an entrepreneur or small business founder, besides Start Small Think Big, what are some resources you'd recommend they check out?

    • We are extremely lucky to work with terrific community partners in both NYC and the Bay Area. In New York, we refer entrepreneurs to Neighborhood Trust Financial Partners for personal financial counseling services. In the Bay Area, we work closely with the San Francisco Economic Development Alliance (, a collaboration of 18 nonprofits in the small business space, all of whom work together to support entrepreneurship in different ways (by providing technical assistance support, incubator space, funding, etc.).

      It is also important to note that our organizational success depends upon an active and inspired group of legal, financial and marketing volunteers. This past year, we worked with over 1300 volunteers, who provided over $10 million in pro bono support to our clients!. We are very lucky to have such a skilled group of corporate and individual volunteers who work with us, and support our clients’ growth.

    • I love the entrepreneurs that we have the honor to support. Each one tells a different and inspiring story of an individual who is working so hard to find a way to do what they love. Every single one of them helps me to focus on why Start Small’s work is so critically important.

    • There is a direct correlation between supporting your local small business and community and economic development. On average, almost half of every purchase at your local small business is recirculated locally (in the form of payroll, goods/services purchased from area businesses, profits spent locally by the owner, or donations to area charities), compared to less than 14 percent of purchases at chain stores. Take the time and spend the money to support local businesses with your presence and your dollars. You really do vote with your wallet. When you shop locally, you are casting your vote for your community. Start shopping at

    • Congratulations on this new project! How exciting! Great mentors are everywhere, definitely not just in Silicon Valley. The local schools are full of possibilities - community colleges, colleges, graduate schools. There are professors and also student groups who would love a project
      like this. I'd also think about some of your local businesses/companies, all of whom have employees who might be interested in skills-based volunteer opportunities. You could also even post an ad in your local paper if you are looking for mentors with very specific skill sets. Business plan pitch competitions are a great way to drum up interest and support. You should definitely think through a screening process, especially because your mentors will be working with students - maybe a short questionnaire/interview that all applicants will need to complete?

    • Thanks so much for your question. Start Small works with 1300 volunteers each year, who provide about $10 million worth of pro bono legal, financial and/or marketing support to our entrepreneurs. We recruit our volunteers primarily from major law firms, banks, financial institutions and marketing companies (e.g., Simpson Thacher & Bartlett, Debevoise & Plimpton, Morgan Stanley, AIG, Goldman Sachs, Neuberger Berman). Our projects really vary - some are longer-term (e.g., building a website) and some are just a few hours (e.g., incorporating a new
      business). All of our projects are limited scope - i.e., the volunteers know ahead of time exactly what they are signing up for.