Inside the Round

10 Episodes
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By: Bamboo X

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...

How to Build a $20M CPG Brand (Even During COVID) with Hailey Swartz | Inside the Round
07/31/2025

In this episode of Inside the Round, Helena Fogarty interviews Haley Swartz, co-founder of Actual Veggies, a company dedicated to creating healthier, restaurant-quality veggie burgers. They discuss the journey of starting the company during the COVID-19 pandemic, the challenges of fundraising, the importance of having a strong co-founder relationship, and the role of accelerators in their growth. Haley shares insights on navigating the food industry, building investor relationships, and maintaining a healthy work-life balance as a startup founder.

Takeaways
The idea for Actual Veggies was born out of a need for healthier veggie burgers.
Starting during...


How Steve Gilman Raised $3M After His First Startup Exit - Here's His Exact Playbook
#9
07/17/2025

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 decisions that led to millions in funding. 

In this episode of Inside the Round, Steve Gilman shares his entrepreneurial journey from founding Block Party to launching OneRange, an AI-powered talent development platform. He d...


How I Raised $16M to FIX the Youth Mental Health Crisis with Natalie Schneider
#8
07/01/2025

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-being as a founder. The conversation highlights the evolving landscape of startups and the critical need for resilience in the face of challenges.

Takeaways
VC funding is not the only option...


Raising a fund to back the next generation of consumers founders with VHS Ventures | Inside the Round
#7
06/24/2025

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 conversation, Sumeet discusses the challenges faced by emerging managers in venture capital, the tools available for fundraising, and the importance of maintaining mental and physical health in high-pressure environments. H...


Raising a $1.75M pre-seed while navigating pregnancy and motherhood with Amy Kiska of Recess | Inside the Round
#6
06/10/2025

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 the evolving landscape of venture capital and the lessons learned from their fundraising experience. 

The speaker shares insights on the importance of a well-prepared data room for investors, the significance of extensive market research, and the unique challenges fa...


How Rodeo CPG raised $2.5M with Zachary DeAngelo | Inside the Round
#5
06/05/2025

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 profitability in the retail landscape and the significance of community support in the entrepreneurial journey.

Takeaways:
Understanding financing mechanisms is crucial for founders.
Maximizing early valuation can jeopardize a startup's future.
Building relationships with...


Raising $1.4M to CHANGE how companies hire with Michelle Volberg | Inside the Round
05/27/2025

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 valuable guidance for aspiring founders navigating the complexities of entrepreneurship.

Takeaways: Most Slack channels are public and you can find them just by Googling.I take one day a week off, a...


How we raised $2.2M in funding to transform government hiring with AI | Inside the Round
#3
05/14/2025

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 of securing pilot programs to validate their business model.

The speakers discuss their experiences with fundraising, the importance of conviction in their startup journey, and the challenges they faced in navigating the investor landscape. They emphasize...


Navigating the Fundraising Landscape to Raise $1.2M with Toby Egbuna | Inside the Round
#2
04/28/2025

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 and the role of grants in their funding strategy, emphasizing the importance of building relationships and networks in the startup ecosystem. In this conversation, the speakers delve into the intricacies of fundraising for startups...


From Rejection to Resilience: A Startup Journey with David Dellapelle | Inside the Round EP 1
#1
04/08/2025

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 in investor relations and offers valuable insights for aspiring founders on how to create value and build meaningful connections.

Takeaways
Talking to customers is more valuable than talking to VCs.Rejection is part of the journey...