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.

059: The Leadership Consortium CEO Cara Shortsleeve

Guest Ryan Durkin is a serial entrepreneur, operator and product guy who’s interwoven himself into the fabric of Boston’s elite tech talent. Following his latest successful stint serving as head of product at Drizly (sold to Uber for 1.1B), Durkin is now busy building a sports agency for tech professionals in Boston -- The Operators. Durkin’s goal is to represent the top percent of tech talent, and offer them everything that agents provide to professional athletes -- from opening doors and closing deals to creative contracts and fan ownership. Durkin negotiates on their behalf much like a sports agent would, and helps The Operators and founders build strong companies. 

Durkin is no stranger to startups. He previously founded Wayfund, HeadstoneHub, and OneGoodMeal. Additionally, he was the cofounder of Dailybreak (acquired by Connelly Partners) and was a product manager at Wayfair (pre- and through IPO). 

We got a chance to catch up with Durkin before he hit the road on his motorcycle for a six-month journey around the country. Enjoy.

062: The Operators CEO Ryan Durkin

Guest Jordan Staab is the CEO of SmarterTravel, an industry leader in online travel with a travel media portfolio including Airfarewatchdog, BookingBuddy, Family Vacation Critic, Oyster, SmarterTravel, and WhatToPack. As the story goes with most entrepreneurial ventures, Staab’s journey in building SmarterTravel endured various pivots, twists and turns to get to where it is today. The company is flourishing but Staab will be the first to tell you that this was not always the case. 

With Staab at the helm, SmarterTravel empowers 7 million unique travelers each month through engaging content, innovative technology, and strategic partnerships to help them find the right trip at the right price. The company’s success was rewarded in September 2021 with a $9.5 million series B funding round co-led by Link Ventures and Second Alpha. 

Staab was previously the VP of Revenue at Cognius, and later became CRO when it spun out of Link Ventures’ incubator CogoLabs. When Jordan saw that Cognius was able to predict patterns in travel consumer behavior, Staab co-founded Hopjump. That company started out in 2018 as a digital marketing agency that focused on partnering with brands to develop user acquisition campaigns. Staab and his team went on to launch their first product in January 2020 and saw 60,000 members join in the first few months. Staab was on a joyride that seemingly had no end, then the COVID-19 global pandemic took the world by storm and brought so much momentum, potential, and belief to an immediate halt.

Staab, along with the entire population, had one option, and one option only, PIVOT. Hopjump paused their travel product and focused on content. Staab then learned through industry contacts that TripAdvisor was looking to sell a number of their travel properties, many of which he was familiar with. He saw this as an immense opportunity for Hopjump, and purchased all of the properties, one of which was SmarterTravel. Since that name closely aligned with Hopjump’s purpose and goals, the company adopted that name and in September of 2021, announced funding and Staab’s bump to CEO. 

A global pandemic was nowhere to be found in Staab’s playbook, but rest assured staying agile and nimble to whatever life throws at him, surely was. Find out how Staab not only stayed afloat, but flourished in one of the most challenging times the industry has ever seen in this week’s episode.

068: SmarterTravel CEO Jordan Staab

Guest Russell Follansbee leads Silicon Valley Bank’s (SVB) enterprise software team in New England, which counts roughly 60 percent of VC-backed startups in the Greater Boston region as clients. 

He and his team help enterprise software companies, typically post-series A funding, to more efficiently achieve scale. While his experience ranges across industries, Follansbee specializes in the cybersecurity industry, a technology cluster in Boston that is driving global innovation. 

Since joining SVB in 2009, Follansbee has worked with high-growth innovators at all life stages, from pre-seed startups to billion dollar juggernauts. This experience has afforded him deep insights into patterns of success and failure, making him a valuable resource to founders and C-level executives. 

Follansbee lives in Boston with his wife and two kids. In his free time, he serves on the Rising Leaders board of BUILD Greater Boston, an organization that calls on the tenets of entrepreneurship to help youth in underserved communities succeed in high school, college and beyond.

070: Silicon Valley Bank’s Russell Follansbee

Guest Dan Rossignol is an entrepreneur, investor and lifelong learner with a proven track record as a technology generalist who can drive revenue across business verticals. He currently serves as the Chief Growth Officer at Stonehenge Technology Labs, doing business as STOPWATCH, a Bentonville, Arkansas-based unified commerce software startup that provides real-time supply chain management for global CPG brands. 

Rossignol is also a scout investor for Bonfire Ventures, a seed stage venture capital firm that leads Seed rounds for business software solutions company founders. 

Prior to his current roles at STOPWATCH and Bonfire Ventures, Rossignol was in multiple leadership positions from co-founding Ad On Feet, an experiential guerilla marketing company, to serving as the Head of Partnerships at UserTesting ($USER), where he built and ran the company’s first channel sales and strategic partnership playbook across all of their strategic consulting and digital agency partnership networks.

Having led business development, product marketing, and operation teams across the globe, Rossignol has a unique humanity-first approach to operating and investing. From startups to scale ups, he leverages several years of operating experiences to help underestimated teams build a better future for tomorrow, today.

074: Investor & Entrepreneur Dan Rossignol

Sara Mraish-Demeter is an artist, educator, mother of three, and founder/CEO of Art Resource Collaborative for Kids (ARCK), a nonprofit delivering creative programs with social justice themes in Boston Public Schools since 2012. Born in Jordan to Palestinian refugee parents, she came to the United States at age 15 and Boston was where she first experienced real support and opportunity. 

In Boston, Mraish-Demeter quickly learned that none of her schooling transferred from Jordan, so she had to go back to school and get her GED. It was through this incredibly low point in her life that put her in an environment to realize that the lack of arts in school prohibited kids from expressing herself. What first seemed like a nightmare, led to her calling.

She has now made it her life’s mission to promote cross-cultural inclusion and understanding among Boston’s children. She is passionate about using art as a vehicle to reimagine education and unlock each child’s full potential. With ARCK, she has forged many partnerships with schools, businesses, institutions, and artists to bring youth voices to the wider community through projects such as “I Am, We Are,” a collaborative public art mural, and “Walls that Speak,” a showcase of immigrant students’ stories. Internationally, during the summers of 2013-14, she led art workshops for Syrian refugee children in Jordan.
 
Mraish-Demeter was named a 2016 EXTRAOrdinary Woman of Boston by Mayor Walsh’s Office of Women’s Advancement and selected for the Power Launch inaugural Social Change Fellows cohort. She is an active member of the Beacon Hill Circle for Charity, which supports Boston children and women, and a former board member at the Center for Arabic Culture. She holds a B.A. in Psychology with a minor in French and completed the Nonprofit Management and Leadership program at Boston University.

In this episode, Mraish-Demeter dives into her story, inspiration for founding ARCK, the many lessons she’s learned across her wide range of experiences throughout her life, and so much more.

079: Sara Mraish-Demeter, CEO/Founder of ARCK

Guest Lily Lyman is a General Partner at Underscore VC, a leading Boston venture capital firm known for its Underscore Core Community of proven business builders helping each other succeed. She is also a Board Director for the New England Venture Capital Association, MIT Sandbox Funding Board, and is a leader of the Boston All Raise chapter.

Lyman has a background as a founder, investor, and operator. She came to Underscore VC from Facebook, where she worked in product strategy focused on the international growth of core products including Facebook, Instagram, WhatsApp, and Messenger.
 
Prior to Facebook, Lyman held a variety of strategy, operational, and entrepreneurial roles. Through it all, she has gained a truly global perspective, having lived and worked in more than 75 countries. 

At Underscore VC, Lyman leads investments on Future of Work, AI/ML, Insuretech, Commerce, and more. With experience that spans the globe, she spends her time identifying investment opportunities and guiding startups that will define new digital categories, reshape industries, and change the world. 

On this episode of Boston Speaks Up, we chat with Lyman about her lessons from the past, her bets today and her predictions for the future.

085: Underscore VC's Lily Lyman

Guest Chris Cardoza is the Founder & Director of Doza Visuals, a Boston-based media production company with experience filming and photographing across the globe. You may be familiar with Cardoza’s work locally via the artist documentaries he produces for ICA Boston. 

Cardoza’s entrepreneurial journey was preceded by a childhood culminating as a multi-sport athlete in high school. Sports were everything to him, until injuries crept into his life and ripped away his first passion. This is when he discovered a new calling in photography and video and he brought that same energy, determination and dedication to his new craft. Although playing sports came to a halt, in this episode we learned that his relationship with sports found a way to blossom in a creative way. 

For the past decade, Doza has been shooting stills and videos for some of the most recognizable brands and publications in the world. He’s worked with companies such as Reebok, ESPN, TB12 Sports, VICE and many more. When he’s not behind the lens pointing his camera at athletes such as Olympic Gold Medalist Aly Raisman or NFL Superstar JJ Watt, you can find Doza traveling to countries such as Rwanda and documenting how sports are affecting the world. 

Outside of his work, Cardoza spends his time watching documentaries, flying drones, trail running and spending time with his newborn twins. On this episode of Boston Speaks Up, we chat with Cardoza about juggling parenthood with running a startup, traveling in Rwanda with renowned Boston sports journalist Jackie MacMullan, what it’s like working with star athletes, and what it takes to start your own business.

087: Chris Cardoza of Doza Visuals

Guest Alex Kantrowitz is the founder of Big Technology, a combo newsletter-podcast news operation analyzing the systems in the tech world that drive what we see in the headlines. He launched Big Technology on the back of his wildly successful book Always Day One, which gives a behind-the-scenes view into how Amazon, Facebook, Google, and Microsoft have “stayed on top” by operating in Day One: Instead of hunkering down and protecting core advantages, they reinvent constantly. 

Kantrowitz most recently served as senior technology reporter at Buzzfeed, and he regularly appears on CNBC to break down the news surrounding the tech giants. He penned the Tech Giant Update newsletter at BuzzFeed. In that role, he fell in love with the back and forth with readers, and found that the live replies with his audience were incredibly heartfelt and informative. It then comes as no surprise that he’s now made a newsletter his de facto journalism format. 

Prior to Buzzfeed, Kantrowitz spent time writing for Forbes and Ad Age. He reported on marketing technology at Ad Age, which gives him a really interesting perspective at the intersection of technology disruption with advertising and commerce. 

He studied at Cornell University where he wrote for the Cornell Daily Sun and co-hosted WVBR's Weekend Pulse. His radio background shines in his Big Technology podcast and furthermore when he appears as a guest on shows such as his appearance here on Boston Speaks Up. 

In this episode, we discuss with Kantrowitz his journey to starting Big Technology, his modern media business monetization model, recent news such as the spiral of Silicon Valley Bank, his time in Seattle working on Always Day One, the impact of AI, the future of Big Tech, and much more.

088: Alex Kantrowitz of Big Technology

Guest Kerty Levy is the Managing Director of Techstars Boston, the successful startup accelerator tied to a global network of Techstars programs. (Techstars Boston applications are open now and will close June 7, 2023. Don’t miss out!) 

Levy replaced Greg Raiz, who stepped down as managing director at the end of October 2022. She brings a global perspective to her role having grown up all over the world. Born in Japan, Levy spent time in the Philippines, Belgium, Switzerland and Sweden before settling in the United States.

Levy is also the managing director of recently launched Techstars Crypto Boston, a crypto-focused accelerator in Boston. This program, run in partnership with Algorand and the Algorand Foundation, is designed for startups globally that focus on innovative and fast-growing web3 development solutions that cut across Decentralized Finance (DeFi), Gaming, Creator Economy, and many more. Techstars Crypto Boston kicked off in January 2023 and just held DemoDay on April 6, 2023. 

Levy has been with Techstars since 2019. Before her move to Boston, she served as managing director of Techstars Iowa. Prior to that, the long-time business advisor and coach spent time at the Iowa AgriTech Accelerator where she was a trusted member of Iowa’s startup community and expert on the Des Moines entrepreneurial ecosystem.
Levy is a lifelong learner. After graduating from the Stevenson School, she went on to earn her Bachelor of Arts in International Relations from the University of California, Davis. She then earned her MBA from Harvard Business School.

In this episode, our host Zach Servideo discusses with Levy her career journey, what she loves about Boston, the startup sectors that most intrigue her, the future of crypto/blockchain, and much more.

089: Kerty Levy of Techstars Boston

George Deveney is the Chief Advancement Officer at Make-A-Wish Massachusetts and Rhode Island, headquartered in Boston, MA. Make-A-Wish is a non-profit organization on a mission to create life-changing wish experiences for children with critical illnesses. In 2023, Make-A-Wish Massachusetts and Rhode Island celebrate 40 years of providing life changing experiences to kids and families who deserve it the most.

Deveney has dedicated his life to helping others and he has no plans of taking his foot off the gas. Prior to joining Make-A-Wish, Deveney spent the majority of his career at City Year, an education-focused non-profit organization that unites young people from diverse backgrounds for a year of full-time service to keep students in school and on track to high school graduation. At City Year, Deveney led development of the organization and successfully launched regional teams in more than 10 cities including London, Denver and Orlando. 

As a Dorchester native, the return to the Greater Boston area to serve this community he once called home was inevitable. For Deveney, getting the opportunity to lead development for Make-A-Wish, one of the most well-recognized non-profit organizations in the nation, is his own dream come true. And as one could imagine, growing up in the area has left Deveney with strong family ties to Boston and surrounding neighborhoods. This has allowed Deveney to stay in tune with local culture, and more importantly makes this role that much more important to him.

In his role, Deveney is responsible for driving the organization’s growth in Massachusetts and Rhode Island. We unpack his specific efforts to do so in this episode as we also explore Deveney’s career journey, what he finds so special about Boston that brought him back, his passion for helping others through non-profit organizations, and much more.

090: George Deveney of Make-A-Wish

Devan Sood is the Co-Founder of Orca, a membership-based network of furnished month-to-month accommodations in dream destinations around the world. As working a 9-5 increasingly no longer requires a long commute to a 5’ x 5’ cubicle, Orca is designed for digital nomads who travel freely and work remotely around the globe. A digital nomad himself, Sood is currently traveling the world helping inspire others to ditch their 12-month lease and live in a myriad of their dream destinations, without breaking the bank.

Sood grew up in Los Angeles and jumped into his first venture at the ripe age of 14 when he started Unlimited Ltd. Clothing. Within less than 3 years, Unlimited Ltd. was being sold in multiple countries, endorsed by top celebrities, and working with charities across the globe.

I had a chance to meet Sood when he was at Babson College where he was racing to graduate early and build more startups. He graduated in less than 3 years and moved back to LA to launch a marketing consulting firm specializing in creative growth strategies to market to Millennials and Generation Z. That venture evolved into 96-LA, Sood’s growth agency focused on helping early-stage consumer-facing tech startups with product-led growth and acquisition experimentation. 

With 96-LA still growing, Sood is leveraging his consulting skills to fuel the growth of Orca, while he travels the world living the experiences he is pitching to fellow digital nomads. We talk about all of this, Sood’s advocating for “teen-preneurship” and much more.

091: Devan Sood of Orca

Dr. Jeff Sutherland is the Founder and Chairman of Scrum Inc. He is credited with being one of the creators of Scrum, which is celebrating its 30 year anniversary in 2023, and is a framework for enabling business agility at scale across an entire organization. 

Sutherland’s mission has always been to spread Scrum around the world to free people from what he calls “the incredible life-draining system they’re working under.” His teachings consistently expose the archaic systems that hinder productivity, and he’s at the forefront helping the world’s biggest organizations make the transition to Agile. 

To further his efforts, Sutherland is also a co-creator of The Agile Education Program powered by Scrum Inc., a training suite providing the curriculum and educational standards that give individuals and organizations a clear path to implementing Scrum in a way that drives immediate business results. 

A graduate of West Point, Sutherland served as a fighter pilot during the Vietnam War and later spent time conducting cancer research before immersing himself in the world of software development. With his expertise, Jeff has held the role of Chief Technology Officer at eleven different software companies, bringing a wealth of experience to each endeavor. 

In 1993, Jeff pioneered the concept of Scrum by launching the first Scrum team. While things have changed a lot since then (spoiler alert: those original month-long sprints were far too long), he has continued to play a pivotal role in expanding Scrum’s ability to drive Agile transformation at organizations across industries including government, finance, healthcare, higher education, and telecom. 

Recognizing the transformative power of Scrum, Sutherland co-authored the bestselling book Scrum: The Art of Doing Twice the Work in Half the Time, and later published A Scrum Book: The Spirit of the Game. Through his books and extensive knowledge sharing, he has become a respected figure in the Agile community. His passion for fostering energy, focus, clarity, and transparency in project planning and implementation has made scrum a highly sought-after approach for organizations seeking efficient and effective project management. 

We had a chance to sit down with Sutherland as he reflects on 30 years of Scrum, the new Scrum QuickStart offering and what the future holds for Scrum’s biggest possible impact on the world.

092: Dr. Jeff Sutherland, Scrum Co-creator

Guest Stephanie Roulic is the founder and CEO of Startup Boston where she’s become a driving force behind Boston's startup ecosystem. Through Startup Boston, Roulic is on a mission to bring networking opportunities that bridge connections between people from different industries and companies from all stages. She leads a team of dedicated volunteers who are all aligned in fulfilling Startup Boston’s vision to establish a more connected Boston business ecosystem. 

Since co-founding the martech company nDash in 2016, she recognized the need for meaningful connections in the local startup community. This led her to also launch Startup Boston Week in 2017, an annual event that brings together thousands of attendees and hundreds of speakers, including industry luminaries such as Brian Halligan and Jules Pieri. 

Throughout her journey, Roulic's leadership and passion have shone brightly. From being the first non-engineering hire and employee number 11 at Goldcast, she built out and managed customer success and support teams. She's played an instrumental role at MassChallenge and nDash as well, demonstrating her expertise in community-building and client support. Her accomplishments extend to education where she advises Suffolk University's Management & Entrepreneurship Career Community Advisory Group.

In 2022, her efforts with Startup Boston were recognized by the Boston Business Journal as she was named one of BBJ’s 2022 40 Under 40 Honorees; and prior to that was named to BBJ’s Power 50 for 2020. Her strategic prowess is evident in securing sponsorships, developing onboarding strategies, and creating year-round initiatives and events. With a commitment to diversity, her leadership has resulted in Startup Boston Week drawing a majority representation of women and people of color among speakers.

Roulic's journey began with a Bachelor's degree in Communication and Media Studies from the University of Massachusetts Amherst. Her dedication to her craft and community led her to embrace roles at Geek Girl, where she served as Program Coordinator as a dedicated volunteer. From nDash's inception to the birth of Startup Boston, Stephanie Roulic's profound impact on Boston's startup ecosystem is truly commendable.

093: Stephanie Roulic, Startup Boston founder/CEO

Guest Gabriela Serret-Campos is the Global Head of People Strategy and Talent at Chronosphere, a cloud company that raised $200 million on a $1+ billion valuation in 2021. She is a seasoned professional with a rich background in shaping organizational strategies and fostering talent to drive success. 

As the modern workplace changes, Serret-Campos is an expert navigator of the evolving shifts and new challenges in recruiting and culture building. She possesses invaluable insights into how venture-backed companies can quickly scale a team with an emphasis on employee retention.

Prior to Chronosphere, Serret-Campos served as the SVP of People Operations at Drizly, where she played a pivotal role leading up to the company’s acquisition by Uber for $1.1 billion in 2021. Adjacent to her roles, she founded Lead by Design, an advisory consultancy specializing in leadership development, strategic planning, and DEI initiatives. Serret-Campos is a founding member of the POPS Advisory Board, championing a people-first approach and promoting the idea that employees deserve care and investment. She’s also a member of the Underscore VC Core Community. 

Her earlier experience included running boutique leadership development firm Intelligent.ly, which was focused on partnering with hyper growth tech companies to help them align their people to purpose to drive productivity. She did similar work at Infusionsoft and EDMC-OHE, highlighting her consistent dedication to fostering leadership development. She designed innovative programs and initiatives that helped emerging leaders thrive and succeed. 

We were honored to sit down with Serret-Campos at Startup Boston Week to discuss all of her experiences and how they have shaped her ability to navigate the future of work.

094: Gabriela Serret-Campos of Chronosphere

Stanley Rameau is the Founder and CEO of Renavest, a financial education community for investors and individuals to connect, share and build wealth. He is poised to make an even greater impact with the imminent release of the Renavest app on both the App Store and Google Play Store this fall (Join the waitlist). 

When Rameau isn’t guiding individuals from all walks of life along their journey to wealth building, he can be found building and growing his Boston-based fashion brand, Paul Rameau.

Rameau's journey is defined by a mosaic of diverse work experiences that have molded him into the inspiring figure he is today. His early career involved roles in design and marketing within the fashion industry, where he fine-tuned his creative talents. Later, he ventured into entrepreneurship, growing multiple successful startups. Rameau's career path showcases his versatility and a relentless drive to make a meaningful impact.

In 2019, Rameau launched Paul Rameau in honor of his father’s passing to myeloma. The fashion brand is making waves in the Greater Boston Area, as covered in this article from The Boston Globe. Rameau's unique creativity is deeply rooted in his commitment to unlocking his own untapped potential, a commitment that reverberates throughout his remarkable career. His wellspring of creativity flows from a profound commitment to unlocking his untapped potential. In all his endeavors, he strives to encourage others to embrace risks and embark on their personal journey of doing the same. 

We were grateful to sit down with Rameau at Startup Boston Week to discuss his passion to help individuals take calculated risks and transform their lives.

095: Stanley Rameau of Renavest

Senofer Mendoza is the Founder and General Partner at Mendoza Ventures, a woman-owned and the first Latinx-founded VC fund on the east coast. In the ever-evolving landscape of venture capital, Mendoza stands as an innovation economy trailblazer and an advocate for diversity and inclusion.

Mendoza has a creative background having previously worked as an interior designer for Parker Torres Design. During her stint at the design house, Mendoza was able to work on some exciting projects, most notable would be her design work for Boston’s beloved Fairmont Copley Plaza. Although Mendoza took pride in her creative abilities, she quickly realized to reach her full potential she needed to take fuel from her passion of bringing equity to women in VC and underrepresented founders around the world. 

Through Mendoza Ventures, she and her team focus on investments in fintech, AI, and cybersecurity, with diversity playing an important role in their investment decisions – about 90% of their portfolio consists of startups led by immigrants, people of color, and women. Since its founding seven years ago, Mendoza Ventures has raised two funds and had two successful exits. Bank of America Corp. is an anchor investor for the new $100 million fund managed by Mendoza Ventures, announced in January 2023. 

Mendoza's outstanding contributions have been alluring attention from the Boston community, and beyond. In 2022, Axios Magazine recognized her as one of the five most influential people in Boston. Shortly after, the LA Times honored her firm as a DEI visionary as one of California’s most prominent game-changers and thought leaders in the business world today. Currently, she sits on the NACIE, the National Advisory Committee for Innovation and Entrepreneurship.

Mendoza's remarkable journey, from an advocate for diversity to the founder of the groundbreaking Mendoza Ventures, exemplifies her unwavering commitment to driving positive change in the VC landscape. As an influential figure and pioneer, she continues to pave the way for underrepresented voices in entrepreneurship. 

We were fortunate to sit down with Senofer at Startup Boston Week to discuss her career journey and her vision for a more equitable future for the startup community.

096: Senofer Mendoza of Mendoza Ventures

Guest Alice Pomponio is the Managing Director at BrightEdge, the venture capital and impact investment arm of the American Cancer Society, where her work is making waves in the fight against cancer. With a passion for economic and health equity, she has built a strong track record of bringing groundbreaking ideas to life, developing cutting-edge technologies, shaping markets, and creating value within these ecosystems. 

Pomponio's journey through the biopharma industry has tracked alongside many of the industry’s defining moments, earning her the playful title of the ‘Forrest Gump’ of biotech. Through the many ups and downs of the economic cycle, Pomponio has persevered as many professionals would, but for her this is much more than a career path. For Pomponio, this mission is deeply personal. Having lost her mother to cancer and witnessed her family's 14 battles against seven different types of cancer, she is committed to the fight against this deadly disease, all while making health equity a central focus of her work.

In her current role as Managing Director at BrightEdge, Pomponio spearheads efforts to fuel the fight against cancer through impact venture capital and patient-centric innovation. BrightEdge was founded by the American Cancer Society in 2019, and is a beacon of hope for the fight against cancer. Pomponio's work at BrightEdge is a testament to the idea that philanthropy can ‘supercharge’ donations. By investing in healthcare startups that blend financial growth with cancer-fighting innovations, Pomponio and her team ensure that every dollar donated has the potential to multiply through the investment process. This not only accelerates the development of life-saving technologies but also supports startups that might otherwise struggle to secure seed funding.

On top of her work at BrightEdge, Pomponio is also Vice President of Innovation and Impact Investing at the American Cancer Society, and also serves as faculty at the Massachusetts Institute of Technology, further contributing to the advancement of healthcare and innovation. Pomponio's commitment to her mission is further exemplified by her roles as Board Observer at healthcare-focused companies such as Naveris and Vincere Health. 

It was an honor to sit down with Pomponio and discuss her inspiring journey and groundbreaking work at BrightEdge, and most importantly, her unwavering dedication to the fight against cancer and health equity.

097: Alice Pomponio of American Cancer Society’s BrightEdge

Barbara Fortier is the CEO of the Girl Scouts of Eastern  Massachusetts (GSEMA) where she has over 25 years of experience in the nonprofit sector.  Before assuming this role, she served as Chief Operations Officer at GSEMA for an impressive 17 years. 

Fortier's influence extends beyond her impressive tenure at GSEMA. She is a specialist in  volunteer management, fundraising, and female empowerment, making her a sought-after  expert in her field. As the CEO of the largest girl-serving organization in Massachusetts and the  10th largest Girl Scout council in the nation, Fortier's mission is to create girls of courage,  confidence, and character who contribute positively to the world. 

Her impact isn't limited to her professional role; it resonates within the Greater Boston  community. Fortier is deeply passionate about spreading leadership opportunities to women of  all ages and backgrounds. Her commitment to female empowerment shines through every facet  of her career and personal life. 

Fortier recently penned an op-ed in the Boston Business Journal about how Girl Scouts  addresses the youth mental health crisis. We explore this topic and much more in this latest  ‘Boston Speaks Up’ episode.

098: Barbara Fortier of Girl Scouts of Eastern Massachusetts

Guest Kristen Craft is the new Vice President & Business Partner Manager at Fidelity for Startups, one of the largest brokerage firms in the United States, headquartered here in Boston. She’s a major catalyst supporting Fidelity in its efforts to help fill the startup banking void in Boston. 

Craft is working closely with the team at Shoobx, a Cambridge-based fintech Fidelity acquired in January 2023. Shoobx helps companies with equity and board management, storing and sharing important business information, and bringing together startup leaders, lawyers, and investors in a single collaborative hub. 

Similar to her previous roles, Craft’s role at Fidelity entails her helping startups navigate the financial moments that matter most: fundraising, cap table management, access to investors; alongside all of the other financial expertise and services that Fidelity has long been known for. 

Craft is a proven entrepreneur with more than 15 years of experience in enterprise software and digital marketing. With a passion for entrepreneurship, she’s become well known around the Boston startup community for her passionate support of founders and VCs. 

In her role evangelizing the Boston-area startup community, Craft also recently supported the production of a 2024 AI report from Value Creation Labs – Boston Startups Put AI and Data to Work in Vertical Industries and Enterprises. 

Craft is also a previous guest of Boston Speaks Up, and folks can learn more about her previous career journey in the episode from 2022. Her past experience includes leadership roles at Animalz, Tettra, Ovia Health Wistia, and Transparent Language, as well as launching her own start-up, Brown Box Storage. 

In her return to the Boston Speaks Up show, she is eager to share best practices on go-to-market strategy, fundraising, and other vital aspects of the startup journey. Drawing from her decades of experience as a startup operator and angel investor, she's gathered a great deal of wisdom and is enthusiastic about making the startup journey smoother for others.

099: Kristen Craft of Fidelity for Startups

Guest Nick Cicero is an analyst, entrepreneur and growth expert operating at the intersection of digital media and advertising. He made a name for himself in the 2010s when he founded Delmondo, a social video analytics company. 

Founded in 2014, Cicero quickly established Delmondo alongside established media measurement companies by introducing numerous industry firsts, including the first enterprise analytics solutions for Snapchat, Instagram Stories, and Facebook Live used by clients such as ABC News, the NFL, WWE, Fox, UEFA, Paramount and more. He and Delmondo also co-produced the first Snapchat Branded Long-Form Ad Series with Marriott Rewards. 

Raising only a single angel investment round, Cicero steered Delmondo into a profitable startup that garnered millions in revenue, hundreds of loyal customers; and set new industry standards culminating in its acquisition by Conviva in 2018.

During his time building Delmondo, Cicero was also a cofounder of TVREV, an analyst business reporting on the convergence of TV and digital media. He partnered on TVREV with a who’s who list of media executives that all participated in Conviva’s angel investment round –  Gary Vaynerchuk (VaynerMedia), Jesse Redniss (former WarnerMedia, current founder at Qonsent) and David Beck (current Brightcove COO) – who collectively operated as BRaVe Ventures. 

Cicero stayed on at Conviva for several years to lead Conviva’s social intelligence business in a VP of Strategy role. At Conviva, Cicero focused on extending their portfolio of measurement products that enable video publishers, sports teams, leagues, and streaming TV providers to get a 360-degree understanding of the viewer journey and grow viewership, engagement, and revenue. 

He departed Conviva in 2022 to pursue consulting opportunities and explore new entrepreneurial endeavors. He joined the ranks of consulting firm Value Creation Labs (VCL) in 2023, establishing himself in a GTM Lead role for VCL and its partners such as Vevo, Precise TV, PadSquad and T-Mobile. 

Cicero is a regular speaker at industry trade shows, and is an expert commenter on industry trends such as his analysis of the $5 billion Netflix-WWE deal featured in The Drum. He also has a passion for mentoring the next generation of media entrepreneurs. He’s an adjunct faculty member at his alma mater, the S.I. Newhouse School of Public Communications at Syracuse University, where he recently announced the formation of the inaugural Emerging Leaders Alumni Board of which he plays a lead role. 

We explore Cicero’s impact on the media innovation community, what he’s up to at VCL, and much more in this latest  ‘Boston Speaks Up’ episode.

100: Nick Cicero, Media Entrepreneur & Analyst

Guest Kyle Wallack is an artist-entrepreneur and the founder of Refined Graffiti, and you can learn more about his work at his digital gallery The KW Gallery. After graduating from Endicott College in Beverly, MA, he lived in New York City for several years where his career took off before recently relocating to the Tampa Bay, Florida area. Wallack, inspired by the likes of Banksy and Basquiat among others, has now done work for global phenoms Missy Elliot and Cardi B. His work has inspired millions across the world.

Before becoming the esteemed American contemporary artist we know today, Wallack’s journey was struck with hardship. In 2018, and at just 23 years old, Wallack was diagnosed with cancer of the parotid gland, which required intensive surgery to remove the cancer from his face. After a successful surgery leaving him with more than 600 stitches, Wallack was walking to his apartment when he stumbled across an easel. Wallack of course picked it up, brought it back to his apartment, and the rest was history.

Due to the nature of his surgery, Wallack was informed by his doctors that the blue light produced by phones and TVs were extremely harmful to his health. With no access to electronics for more than a year, and a newfound easel and paint, Wallack’s journey as an artist began. Once Wallack picked up his newly found paintbrush and graffiti can, he never put them down. Painting became Wallack’s outlet, and as a wide-eyed, young, 23 year-old trying to figure it all out, painting allowed him to produce positively during this time of adversity. 

Before Wallack had his surgery, he had never dabbled in art in an international way. Afterwards, everywhere he looked inspired him to create. Fast forward to the present day, Wallack has now dedicated his full-time career to being an artist. Through years of repetition, hard work, and grinding, Wallack is now represented by Quidley & Co, a well-respected, full-service gallery that has been representing artists for 30+ years.

In this episode, we explore Wallack’s impact that transcends the graffiti and traditional fine art communities, how he perseveres through all the hardships life throws at him, what he’s creating now, and what he wants his legacy to be.

101: Kyle Wallack, Refined Graffiti

Guest Josh Trautwein represents the soul of Boston, a city that looks out for its own with unconditional love and unwavering support. Trautwein was working as a health educator at the MGH Charlestown Healthcare Center when he kept hearing from his families that it was difficult to shop for healthy food. At that time, the only grocery store in the neighborhood was set to be shut down for a year-long renovation. It was this experience and some in-depth research that inspired Trautwein to cofound Fresh Truck, rethinking the traditional grocery store model, making it mobile and providing fresh food access to the people that need it the most. Discover more Boston Speaks Up at Boston Business Journal's BostInno: https://www.americaninno.com/boston/boston-speaks-up/

018: Fresh Truck Founder Josh Trautwein

Fabric Media founder and CEO Jason Damata is difficult to describe in words. He’s a poet and a philosopher. He’s a cunning marketer and chief executive. He’s a business consultant and media analyst. He’s made Advertising Age’s prestigious '40 Under 40' list. He spent time touring the country for CSPAN educating the public about media. Damata’s unique characteristics and impressive accomplishments goes on and on. Above all else, Damata is a family man in the most altruistic sense imaginable. He’s a modern day Godfather to an ever-growing list of collaborators and partners working with Fabric Media, the business accelerator and marketing consortium he founded more than 10 years ago comprised of creative individuals rallied around innovative companies, artists and social good causes. Discover more Boston Speaks Up at Boston Business Journal's BostInno: www.americaninno.com/boston/boston-speaks-up/

021: Fabric Media CEO Jason Damata

Guest Sean Cantwell is a founding team member and Managing Partner with Boston-based Volition Capital, a technology-oriented growth equity and venture capital firm that raised $600 million in separate funds for new investments in 2019. While Volition invests in companies across America, Cantwell has distinguished himself as a growth equity professional dedicated to Boston’s startup community where he focuses on software, technology-enabled services and Internet investments. Cantwell and Volition have invested growth capital in a wide range of Boston-based companies including GRAX, TraceLink, JazzHR, and VisualIQ, among others. Prior to joining Volition Capital, Cantwell was an investor at Fidelity Ventures and worked at Summit Partners where he focused on technology growth equity investments. He began his career at Arthur Andersen. Discover more Boston Speaks Up at Boston Business Journal's BostInno: www.americaninno.com/boston/boston-speaks-up/

037: Volition Capital Managing Partner Sean Cantwell

Guest Rahkeem Morris is the cofounder and CEO of SYRG, a service for employers to hire former workers for shifts and projects on-demand. Morris’ long-term vision for SYRG is to empower a flexible, liquid, universal workforce of hourly workers where any person can work for any place at any time. Morris took an unusual journey into entrepreneurship and has unique gig economy experience having dropped out of high school at 14 years old to help support his family, working 13 jobs over nine years. He then journeyed into academia and tech. He graduated magna cum laude from Cornell University, worked at GE and Google, and then went on to earn his MBA from Harvard Business School. Morris cofounded SYRG to help people like his mom, a single parent with a shifting nursing schedule, to more easily secure relevant short-term gigs. Discover more Boston Speaks Up at Boston Business Journal's BostInno: www.americaninno.com/boston/boston-speaks-up/

038: SYRG CEO Rahkeem Morris

Guest AK Ikwuakor, also known as “Coach AK”, is an entrepreneur, educator, consultant, strategist, storyteller, and former Top 10 world-ranked athlete from the University of Oregon (hurdles; 400 meter). He’s founded several companies including Empower2Play, a sports diplomacy project working with the US Government; as well as ELETE Styles, a made to measure clothing provider for athletes and working professionals. He’s traveled to more than 30 countries working with students, athletes, coaches, governmental agencies, celebrities, victims of terrorism, and CEOs. Originally from Colorado, Ikwuakor has made Boston his home for the past decade. Much of his work aims to foster cross-cultural relations and maximize economic development in under-resourced communities through the power of sports and education. Discover more Boston Speaks Up at Boston Business Journal's BostInno: www.americaninno.com/boston/boston-speaks-up/

046: Entrepreneur-Coach AK Ikwuakor

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.

055: Former Boston Celtics Attorney & 3Point Foundation Founder Neil Jacobs

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.

056: Author & Former Hollywood Assistant Kiel Servideo

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.

058: Serial Entrepreneur & Angel Investor David Chang

Leaders, entrepreneurs, creators, innovators and artists from all over the globe join Boston Speaks Up to share their stories of inspiration. Recommend a guest: team@valuecreationlabs.co. Learn more and sign up for the newsletter: www.valuecreationlabs.co.

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