Inside the Round

Inside the Round

What happens in the room where the deal gets done? Join fundraising expert Helena Fogarty as she pulls back the curtain on startup funding. Each episode features a founder who just closed their round, sharing the raw, unfiltered truth about what it really takes to get investors to wire the money. No sanitized success stories. No vague platitudes. Just real founders revealing their exact process, pivotal moments, uncomfortable conversations, and strategic decisions that led to millions in funding. Whether you're preparing to raise capital or simply fascinated by the inner workings of startup finance, "Inside the Round" delivers the fundraising insights you won't hear anywhere else.

Episodes

How Steve Gilman Raised $3M After His First Startup Exit - Here's His Exact Playbook

July 16, 2025 • 75 mins
Inside the Round is a podcast hosted by fundraising expert Helena Fogarty that pulls back the curtain on startup funding by featuring founders who have recently closed their funding rounds.

Each episode delivers raw, unfiltered insights into what it actually takes to get investors to commit capital, moving beyond sanitized success stories to reveal the exact processes, pivotal moments, uncomfortable conversations, and strategic deci...
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How I Raised $16M to FIX the Youth Mental Health Crisis with Natalie Schneider

July 1, 2025 • 64 mins
In this episode of Inside the Round, Helena Fogarty speaks with Natalie Schneider, founder of Fort Health, about her journey in the startup world, particularly in the mental health sector. They discuss the challenges of fundraising, the importance of understanding VC funding, and the unique hurdles faced by female founders. Natalie shares insights on building a strong team, preparing for fundraising, and maintaining personal well-b...
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Raising a fund to back the next generation of consumers founders with VHS Ventures | Inside the Round

June 24, 2025 • 54 mins
In this episode of Inside the Round, Helena Fogarty speaks with Sumeet Shah, founder of VHS Ventures, about his journey in consumer investing, the impact of market shifts, and the importance of building a supportive ecosystem for founders. They discuss the challenges of fundraising, the role of LPs, and the philosophy behind VHS Ventures, which aims to create a collaborative community for stakeholders in the consumer space. 

In this...
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Raising a $1.75M pre-seed while navigating pregnancy and motherhood with Amy Kiska of Recess | Inside the Round

June 10, 2025 • 40 mins
In this conversation, Amy Kiska, co-founder of Recess, shares her journey of building a startup while navigating the challenges of pregnancy and motherhood. She discusses the importance of identifying market needs, the dynamics of co-founding, and the intricacies of fundraising. Amy emphasizes the significance of building a targeted investor database and leveraging warm introductions to secure funding. The conversation highlights t...
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How Rodeo CPG raised $2.5M with Zachary DeAngelo | Inside the Round

June 5, 2025 • 39 mins
In this conversation, Zachary DeAngelo shares his journey as a founder of Rodeo CPG, discussing the complexities of startup financing, the evolution of funding strategies, and the importance of building strong relationships with investors. He emphasizes the need for emotional intelligence in navigating investor relations and offers valuable advice for first-time founders. The discussion also touches on the challenges of maintaining...
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Raising $1.4M to CHANGE how companies hire with Michelle Volberg | Inside the Round

May 27, 2025 • 34 mins
In this episode of Inside the Round, Michelle Volberg, founder of Twill, shares her journey of building a startup focused on revolutionizing the hiring process through referrals. She discusses the challenges of fundraising, the importance of community, and the lessons learned along the way. Michelle emphasizes the significance of maintaining a work-life balance and the role of investors in a startup's success. Her insights provide ...
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How we raised $2.2M in funding to transform government hiring with AI | Inside the Round

May 14, 2025 • 47 mins
In this episode of Inside the Round, Helena Fogarty speaks with Cherie Chung and Brendan Hellweg, co-founders of Holly, a startup focused on modernizing government hiring through AI. They discuss their journey from identifying a significant problem in local government hiring to successfully raising $2.2 million in funding. The conversation covers their values in selecting investors, the challenges of fundraising, and the importance...
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Navigating the Fundraising Landscape to Raise $1.2M with Toby Egbuna | Inside the Round

April 28, 2025 • 43 mins
In this conversation, Toby Egbuna, co-founder of Chezie, shares insights into the fundraising process, the importance of having a structured approach, and the unique challenges faced by founders. He discusses the origin of Chezie, the dynamics of working with a sibling as a co-founder, and the significance of community support in the entrepreneurial journey. Toby also reflects on the necessity of venture capital for his business an...
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From Rejection to Resilience: A Startup Journey with David Dellapelle | Inside the Round EP 1

April 8, 2025 • 37 mins
In this conversation, David Dellapelle, co-founder of Dune Security, shares his journey of building a cybersecurity startup focused on addressing human error, which accounts for a significant percentage of security breaches. He discusses the challenges faced in fundraising, the importance of customer feedback, and the resilience required to navigate the startup landscape. David emphasizes the need for transparency and authenticity ...
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