Boston Speaks Up

Guest TJ Douglas is the founder and CEO of The Urban Grape, a wine store in Boston’s South End neighborhood known for its proprietary Progressive Scale - a system of sorting wine by its body, instead of by varietal or region. Douglas has led The Urban Grape to becoming one of the most successful independently-owned wine stores in the country as a result.

Douglas’ list of accomplishments is nothing short of astonishing. The Urban Grape has won multiple accolades as Boston’s Best Wine store from both Boston Magazine and The Improper Bostonian, as well as a Small Business of the Year Award from the Greater Boston Chamber of Commerce in 2020. In 2018, Vinepair named The Urban Grape the top retail store in the North East, and Beverage Dynamics named the store a Top 100 Wine Retail Store in America in both 2019 and 2020. The store has also been nationally profiled in Food & Wine magazine, The New York Times, NPR, and Wine Enthusiast. He’s also a seven-time returning Sommelier for the Nantucket Wine Festival.

Douglas also spends time teaching classes on drinking progressively at local places such as the Boston Center for Adult Education, Boston University, the Boston Wine Expo and for companies like Converse, Google, and Wellington. He’s also the co-author of The Urban Grape’s best selling wine education book Drink Progressively, and the resident wine expert on the New England lifestyle show, “Home, Life, and Design.”

He co-founded and runs The Urban Grape with his wife Hadley Douglas. Together, they are also the co-founders of The Urban Grape Wine Studies Award for Students of Color, in partnership with Boston University. They are dedicated to increasing diversity in the wine industry through this program and provide mentorship to other people of color in the hospitality industry. The Douglas’ live in Boston with their two sons.

Enjoy this bonus episode of Boston Speaks Up host Zach Servideo appearing on the Fuel Your Fire podcast from Endicott College's Angle Center for Entrepreneurship where Zach is a visiting Entrepreneur-in-Residence. In this episode, Zach speaks on the future of tech and innovation, tells his story of packing up and moving out west to LA and "Silicon Beach", and shares the heartwarming legacy he wants to leave behind for his daughter.

Guest Cara Shortsleeve is the CEO at The Leadership Consortium (TLC), a leadership development platform designed to accelerate high potential and diverse leaders.

Shortsleeve joined TLC in 2018 to launch and scale the business which has since forged relationships with Google, IBM, HubSpot, P&G, WPP and dozens more. Under Shortleeve’s leadership, TLC has enabled more than 2,000 executives to lead stronger teams and bring broader strategic mindsets to their business.

Prior to joining TLC, Shortsleeve spent more than a decade in various leadership roles at Google and YouTube. Most recently, she served as a Global Director for GTM and commercialization at YouTube, focusing on product and commercial strategy. She was initially hired in 2007 to help launch and scale Google’s east coast, mid-market sales presence, after which she led the North American mid market sales teams for both Financial Services and Healthcare.

Before Google, Shortsleeve managed the US running apparel business at New Balance, served as a Sales Director for Hind/Saucony, and spent three years with Morgan Stanley's Investment Banking Division.

Guest David Chang is an entrepreneur and angel investor who has held product, marketing and operating roles at six startups and invested in 60 companies. He was most recently the CEO at student loan startup Gradifi, which was acquired by E*TRADE in December 2019. Previously, he was Entrepreneur-in-Residence at Harvard Business School and Director of the Babson Summer Venture Program.

Chang has a successful track record in hands-on roles at both direct-to-consumer and enterprise companies, six of which were acquired or IPO’d. He previously led the PayPal Boston office and co-founded the Start Tank innovation space and the Where Angel Fund. Before WHERE’s acquisition by PayPal in April 2011, he held the role of VP of Product.

Earlier in his career, on the consumer side, Chang was Director of New Products at TripAdvisor. Additionally, he was VP of Marketing and Co-founder of SnapMyLife. On the enterprise side, he was Director of Product Marketing at m-Qube, a pioneer in the mobile content space. He also served as Senior Product Manager at edocs and was a VP of Technology at Goldman Sachs.

As a leader in the entrepreneurship community, Chang holds several advisor/board memberships. He is on the board at MITX, an advisor at Harvard Ventures, Nanigans, CO Everywhere, OpenFrame, and Linkwell Health. He has made 60 angel investments in startups such as Crashlytics, clypd, Amino, Logz, Cuseum, CarePort Health, Dashfire, Mogul, Uncharted Play, as well as through the Where Angel Fund and TBD Angels.

We’re grateful to share our interview with Chang as he’s one of the most sought out speakers on the topics of startups, fundraising, and the Boston tech ecosystem, and he actively mentors countless students and founders.

Guest Carly Chase is an Entrepreneur in Residence at the Martin Trust Center for MIT Entrepreneurship. Her work is wide in scope and includes serving as the Founding Managing Director of the MIT NYC Startup Studio (part of the MIT delta v accelerator), running the StartMIT entrepreneurship bootcamp, overseeing the Trust Center’s Membership Program for Organizations and New Frontiers of Entrepreneurship Symposium, coaching students, in addition to serving as a Lecturer in Entrepreneurship at MIT’s Sloan School of Management.

Chase has enjoyed an exciting and wide-ranging entrepreneurial journey. After beginning her career at Goldman Sachs, she joined the New York City Economic Development Corporation under Mayor Michael Bloomberg where she launched and ran a number of programmatic initiatives aimed at making NYC a friendlier city for entrepreneurs to start and grow their companies.

At the end of the Bloomberg administration, Chase left to launch and run Boulder based startup PivotDesk’s NYC office until the company was acquired at the end of 2016. Since then, she has worked within a number of startups in various product development, marketing, and business development capacities.

Additionally, Chase is the co-founder of Crabwalk, an education and coaching company that builds career agility and is based on one simple principle: you don’t have to walk in a straight line to move forward in your career.

We’re delighted to spend time exploring the non-linear path Chase has enjoyed in her career.

Guest Kiel Servideo is a former Hollywood assistant who’s always found comfort with a pen and a notebook. He moved out to Los Angeles a year after graduating from Boston University where he hustled various temp agency jobs before landing full-time gigs with Hollywood titans such as Jerry Bruckheimer and Shawn Levy. While living in LA, Servideo wrote his first novel -- The Preposterous Dreams of Tucker Adams -- a fiction documenting a modern tale of the pursuit of Manifest Destiny.

In the Fall of 2019, Servideo and his wife left their life in Los Angeles and each accepted jobs abroad teaching English to grade schoolers in Seville, Spain. Half way through the school year, a global pandemic changed everything. Servideo spent much of 2020 in lockdown with his wife, utilizing Airbnb to see more of Spain while remaining in isolation.

Servideo is now living in a 300 year old farm house in Umbria, Italy, and he and his wife are working for DTC nail services startup Olive & June.

As Servideo continues to life hack the pandemic, he’s discovering authors, reading, writing and reflecting on the divisive politics in America from Europe. We’re grateful to begin 2021 catching up with Servideo for all to hear.

Guest Neil Jacobs is the president and founder of the 3Point Foundation, a non-profit organization that offers free educational, sports and dance programming to under-served youth in Boston. Working closely with the Boston Celtics, Boston Public Schools, UMass Boston and additional partners, Jacobs and 3Point are on a mission to improve the lives of Boston’s youth through positive reinforcement in the classroom and through group athletics.

Prior to 3Point Foundation, Jacobs served as outside team counsel for the Boston Celtics for 30 years, making it no surprise that 3Point is a community partner of the Boston Celtics Shamrock Foundation. In fact, Celtics owner Wyc Grousbeck is one of the first people Jacobs pitched the idea of 3Point Foundation to.

Toward the end of our podcast discussion, Jacobs shares a remarkable first-hand account of when the Toronto Blue Jays sued the Boston Celtics over the rights of Danny Ainge, including some incredible insight into the mind of Celtics legendary coach and general manager Red Auerbach (see the 59:00 minute mark).

A retired partner of the WilmerHale law firm, Jacobs has spent decades involved in numerous education and basketball programs for youth.

Now serving more than 250 students, 3Point runs after-school programs in Boston K-8 schools and operates summer programming at two locations.

Jacobs is responsible for the overall management and strategic direction of 3Point, and he’s helped 3Point pivot to a virtual education model during the pandemic.

Guest Chris Vail is a Senior Account Executive for Political and Advocacy Partnerships at Snapchat. A former Amazon ad sales leader, Vail made the move to Snapchat to help onboard legislative, issue, and non-profit advertisers onto the Snapchat platform. His team recently launched an augmented reality lens for the Mark Kelly campaign in Arizona, which was the first Senate campaign to lean in on this new, experiential way of engaging voters. Snapchat has also made news waves recently for signing up more than 750,000 young voters via its Snapchat app (and now it’s crossed 1 million registered voters).

Prior to Snapchat, Vail headed up sales for Downstream, a fast-growing Amazon product marketing startup. He began his media career as a planner and buyer for a large D.C. political shop. In 2014, he migrated from politics to ecommerce, moved from D.C. to Seattle and landed at Amazon to help build out its (at the time) small digital ads team. He spearheaded the expansion of Amazon’s ad business into New York, Toronto and Boston, where he eventually moved with his family.

Guest Ari Fine Glantz is the Director of Development & Strategic Initiatives at the New England Venture Capital Association (NEVCA), the regional trade association for the venture capital industry, with mission to foster a collaborative, inclusive, and prosperous innovation ecosystem. At NEVCA, Glantz leads the organization’s revenue generating activities, manages legislative strategy, and supports president Jody Rose on new program development. He has served as a coach and judge for a variety of accelerators and pitch competitions around Boston, and is an infrequent contributor to TechCrunch, BostInno, and TEDx.

Glantz recently launched a lighthearted fundraiser -- Fund.Razor -- to decide the stylistic fate of his year-plus-long beard. All funds raised will support Hack.Diversity, a division of the NEVCA tackling the underrepresentation of high-skilled minority talent in Boston's innovation ecosystem.

Glantz leans on an atypical journey that led him to the NEVCA: entrepreneurship, to international athletics, to social work; San Francisco, to Paris, to Australia, before returning to his roots in New England. He is a graduate of Vassar College and a native Cantabrigian (person from Cambridge).

Guest Veronica Armstrong is the cofounder and CEO of Isle de Nature, a Boston-based home fragrance startup that recently placed runner-up at Roxbury Pitch Night, a virtual pitch night hosted by Venture Café New England’s Roxbury Innovation Center. Isle de Nature offers a line of home fragrance products starting with candles made from beeswax and soy. Armstrong is driven by the belief that "unspoiled nature is a luxury" as climate change threatens the islands she draws inspiration from. Isle de Nature's signature fragrance, Pagua Bay, is inspired by the bay leaves indigenous to Dominica.

Armstrong has deep expertise in e-commerce customer acquisition and product growth. As employee #4 and the former Head of Customer Happiness and General Manager at Lovepop, Armstrong helped the brand grow from unknown to Sharktank to dominating the specialty card market. She spends her free time mentoring female entrepreneurs and was named one of the top 20 female VPs and Directors in Boston tech by Rev in 2018.

Discover more Boston Speaks Up at Boston Business Journal's BostInno: www.americaninno.com/boston/boston-speaks-up/