VCs Off the Record with Gayle Jennings-O'Byrne

In this VCs Off the Record episode, host Gayle Jennings-O'Byrne sit down with Sydney Paige Thomas , Founder & General Partner at Symphonic Capital , to get real about what separates startups that secure funding from those that don’t. 💡 Sydney breaks down why a great idea isn’t enough , how execution sets winners apart , and why not every founder is meant to be CEO . She also shares her in...

In this episode of VCs Off the Record , Jonathan Hakakian , Managing Director at Soundboard Venture Fund , joins Gayle Jennings-O'Byrne for a real talk on what makes founders truly investable . Spoiler: It’s not just a great pitch— it’s how you listen, adapt, and execute. Key Takeaways for Founders: ✅ Investors need a conversation , not a monologue—don’t talk endlessly. ✅ Saying you have no...

In this VCs Off the Record episode, host Gayle Jennings-O'Byrne sits down with Sergio Marrero , Managing Director of Blue Ridge Labs at Robin Hood Foundation, to discuss venture-building with purpose. Sergio Marrero shares his unconventional path from engineering and DJing to venture capital. He breaks down what founders need to move from zero to MVP, why impact-driven startups thrive, and how...

In this VCs Off the Record episode, host Gayle Jennings-O'Byrne sits down with Jackson Feder , an investor at MetaProp , to explore the intersection of real estate, technology, and venture capital. Jackson shares his unique path from launching a startup in high school to becoming a VC, the lessons he learned along the way, and how he evaluates early-stage investments. He dives into the future...

In this VCs Off the Record episode, host Gayle Jennings-O'Byrne chats with Romeo Ortiz , founder of ProductStory Media , and Chi Achebe , a venture capitalist at Achebe Capital . Romeo shares how his background in filmmaking led him to brand storytelling, helping founders craft compelling narratives that connect with investors. He opens up about a $40K mistake that reshaped his approach to con...

In this VCs Off the Record episode, host Gayle Jennings-O'Byrne dives into the intersection of biotech, planetary health, and venture capital with Sabriya Stukes , an investor in early-stage biotech companies. Sabriya unpacks what it means to invest in human and planetary health , breaking down the deep connections between climate, healthcare, and innovation . She shares her unconventional jou...

In this VCs Off the Record episode, host Gayle Jennings-O'Byrne chats with Justin Huebner , author of Inclusive Investing , and Megan Gray , founder & CEO of Moment AI , about the future of venture capital, AI innovation, and what it takes to build a successful, venture-backed business. Justin shares his journey from intern to published author, breaking down the power of inclusive investing an...

In this VCs Off the Record episode, host ⁠⁠ ⁠Gayle Jennings-O'Byrne⁠⁠⁠ chats with Mirit Lugassi , an investor at Laconia Capital , about funding early-stage startups and what it takes to build a venture-backed business. Mirit shares her journey from operator to investor, breaking down the difference between market gaps vs. market demand, how VCs evaluate startups, and the key strategies founders n...

In this VCs Off the Record episode, host ⁠⁠ Gayle Jennings-O'Byrne⁠⁠ chats with ⁠⁠ Desiree Almodovar⁠⁠ , a venture capitalist at Alley Corp VC, and advocate for underrepresented founders. Desiree shares her inspiring journey from leading advertising campaigns to investing in diverse, innovative startups through venture capital. Discover how her unique career path shaped her approach to mentorship,...

In this episode of VCs Off the Record, host ⁠ Gayle Jennings-O'Byrne⁠ chats with ⁠ Victoria Kennedy ⁠, founder of Patternist and former product leader turned venture capitalist. Victoria shares her inspiring journey from scaling startups to launching a groundbreaking venture designed to align financial returns with social impact. Discover how her background in product strategy shaped her approach...

In this episode of VCs Off the Record , host Gayle Jennings-O'Byrne chats with Dawn Kelly , CEO and founder of The Nourish Spot. Dawn shares her inspiring journey from corporate marketing to creating a thriving wellness brand rooted in Southeast Queens. Discover how a personal health journey and a pivotal idea sparked The Nourish Spot along with Dawn's commitment to generational wealth, and the po...

As the year winds down, hosts Gayle Jennings-O’Byrne, CEO of Wocstar Capital, and Victoria Bert, Chief Content Officer at Wocstar Media, share actionable insights to help founders, entrepreneurs, and dreamers prepare for a powerful 2025. In this mini year-end episode, they dive into the art of reflections and road mapping to set meaningful goals for the new year. Hear Gayle's top strategies for bu...

On this episode of VCs Off the Record , host Gayle Jennings-O’Byrne sits down with Josh Tanenbaum , a visionary whose career bridges entrepreneurship and finance. From founding LOCAL VIBES to managing partnerships at Rebalance Capital , Josh shares how his journey shaped his approach to impact investing. Tune in to hear candid advice on balancing financial returns with social impact, avoiding comm...

In this episode of "VCs Off the Record", Gayle sits down with Benny Lorenzo, Managing Partner of Aspira Capital Management and a pioneering force in venture capital since 1996. From his roots in the Dominican Republic to earning degrees from Cornell and Harvard Business School, Benny shares his remarkable journey and insights on securing funding in today's competitive landscape. With over four dec...

In this episode of "VCs Off the Record", Gayle sits down with Megan Ruan, General Partner at Gold House Ventures , an early-stage VC dedicated to supporting multicultural Asian Pacific-founded startups. Gold House is renowned for its in-house accelerator, whose 115+ alumni have collectively raised $2 billion since 2020. Today, Megan dives into the big question: how did they manage to raise so much...

In this episode, Gayle Jennings-O’Byrne goes off the record with Kenneth A Goodwin Jr. , Managing Partner of Jeanensis Ventures. Known for his deep expertise in blockchain, fintech, and digital transformation, Kenneth shares his approach to cash flow management, building partnerships, and the importance of trust and reputation when seeking venture capital. He offers practical advice for founders o...

In this episode, we break down why investing in BIPOC, LGBTQ+, and other underrepresented founders isn’t just the right thing to do—it’s smart business. We discuss the real, often overlooked, financial opportunities tied to investing in these communities, the statistics behind the funding gap, and why businesses led by diverse teams have the potential to outperform in the market. Businesses led by...

In episode three of  ⁠ VCs Off the Record ⁠ , Gayle Jennings-O'Byrne dives into what makes a great idea—and what makes it profitable. She explains that innovation isn’t just about novelty but building a “better machine.” Joined by designer and product developer ⁠Marc Littlejohn ⁠ of ⁠Littlejohn New York⁠ , Gayle and Marc discuss the nuances of entrepreneurship, from crafting a compelling elevator...

In this episode of  VCs Off the Record , Gayle Jennings-O'Byrne opens up about the realities of rejection—what it's like to tell founders "no," why she approaches it differently, and how it has impacted Wocstar. Jesse Middleton, General Partner at Flybridge Capital Partners, known for his expertise in building platforms and communities, goes off the record to share insights into pitching to ventur...

Season three of  VCs Off the Record with Gayle Jennings-O’Byrne kicks off with a conversation between Gayle and Erica Duignan Minnihan , Founder and General Partner at Reign Ventures . Gayle shares the story behind the start of Wocstar with CCO and Creative Director Victoria Bert , revealing the motivations that led her to create a female-forward venture capital fund. Erica and Gayle go off the re...

On this week’s episode, we sit down with Oliver Libby , co-founding Managing Partner of H/L Ventures and CityRock Venture Partners . The H/L family of companies represents a new kind of venture firm, dedicated to building high-growth businesses that add value to society, with a strong preference for diverse founding teams.  In addition to H/L Ventures, Mr. Libby is also Chair & Co-Founder...

We are back for Season 3 and we are SO excited! We are kicking it off with an amazing entrepreneur, Courtne Smith, founder and CEO of NewNew , a social decision-making app that lets you vote to control the outcome of other people’s lives.  Prior to NewNew, Courtne spent over a decade on Grammy-award winning artist Drake's management team where she handled his business endeavors and special pr...

For far too long, implicit bias and systemic racism have created huge gaps in the VC and startup world —favoring white, male founders, while ignoring the brilliant minds of so many others in our diverse world. The data is out there but yet we still aren't seeing capital deployed to the underrepresented.  As a former tech founder himself and a relentless advocate for underrepresented founders,...

We all know you need money to make money but you also need to "bank" money to use it especially as our world becomes more reliant on technology and touch-free. However, many lower-income, immigrants, and even young people do not have access to traditional financial services like banks. This week’s guest, Capway founder Sheena Allen, hopes to change this for the “underbanked” by restoring trust in...

One of the biggest myths in impact and gender lens investing is the lack of data showing the power of investing in diverse and inclusive ventures or those with a gender lens. Investors tend to think “impact” or “gender specific” means soft and small and pass on these opportunities. Although this mindset is slowly changing, many still need data and facts to change their mind. Well, the data is out...