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.
How to Build a $12M CPG Brand (Even During COVID) with Hailey Swartz | Inside the Round
Helena Fogarty interviews Hailey Swartz, co-founder of Actual Veggies, about building a CPG brand during COVID, fundraising challenges, and the importance of co-founder relationships, offering insights into navigating the food industry.
17 Jul 2025
How Steve Gilman Raised $3M After His First Startup Exit - Here's His Exact Playbook
Entrepreneur Steve Gilman recounts his journey from Block Party to OneRange, highlighting fundraising challenges and the importance of resilience, in an interview with Helena Fogarty.
1 Jul 2025
How I Raised $16M to FIX the Youth Mental Health Crisis with Natalie Schneider
Helena Fogarty interviews Natalie Schneider, founder of Fort Health, who shares her experiences raising $16M to address the youth mental health crisis and overcoming challenges as a female founder.
24 Jun 2025
Raising a fund to back the next generation of consumers founders with VHS Ventures | Inside the Round
Helena Fogarty interviews Sumeet Shah, founder of VHS Ventures, about consumer investing, market shifts, and building a supportive ecosystem for founders, highlighting the importance of community and collaboration.
10 Jun 2025
Raising a $1.75M pre-seed while navigating pregnancy and motherhood with Amy Kiska of Recess | Inside the Round
Amy Kiska, co-founder of Recess, shares her experience of launching a startup while navigating pregnancy and motherhood, including fundraising strategies and building investor relationships in this interview.
5 Jun 2025
How Rodeo CPG raised $2.5M with Zachary DeAngelo | Inside the Round
Zachary DeAngelo, founder of Rodeo CPG, details the startup's $2.5M fundraising, highlighting investor relations, funding strategies, and profitability challenges in an interview, offering advice for first-time founders.
27 May 2025
Raising $1.4M to CHANGE how companies hire with Michelle Volberg | Inside the Round
Twill founder Michelle Volberg details her experience raising $1.4M to transform company hiring practices through referrals, highlighting the importance of community and work-life balance in this interview.
14 May 2025
How we raised $2.2M in funding to transform government hiring with AI | Inside the Round
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 the need for transparency, building strong partnerships, and maintaining a balance between work and personal life as they transition from students to founders in the GovTech space.
Takeaways:
Investors should respect local governments and their workers.
Local government hiring takes significantly longer than in the private sector.
AI can transform government operations and hiring processes.
Building a startup requires a strong co-founder relationship.
Fundraising is similar to a sales process, requiring qualification and pipeline management.
Securing a pilot program is crucial for validating business ideas.
Networking and warm introductions are key in fundraising.
Understanding the market and customer needs is essential for success.
Having a clear vision and mission attracts the right investors. The power dynamics in fundraising shift as interest grows.
It's crucial to approach fundraising as a partnership, not a pitch.
Building internal conviction is essential before seeking external funding.
Chapters:
00:00 Investor Considerations and Values
01:27 The Birth of Holly: Founders' Journey
03:00 Identifying the Problem: Government Hiring Challenges0
6:40 Building a Startup: From Idea to Execution
10:08 Navigating the Fundraising Landscape
12:54 Securing the Pilot: Long Beach Case Study
18:17 The Fundraising Process: Angels to VCs
23:08 Pivotal Moments in Fundraising
24:53 Shifting the Power Dynamics in Fundraising
30:50 Building Conviction and Overcoming Uncertainty
35:06 Navigating the Fundraising Process
40:10 Post-Funding Realities and Responsibilities
43:07 Maintaining Balance in the Founder Journey
Find Brendan here: https://www.linkedin.com/in/brendanhellweg/
Find Cherie here: https://www.linkedin.com/in/cheriechung/
Follow us:
LinkedIn (https://www.linkedin.com/company/bamboo-crowd/)
Spotify (https://open.spotify.com/show/5NVE9AhSS5LGb6iepeZW3o)
To learn more about BTG: https://bambootalent.group/ (https://bambootalent.group/)
28 Apr 2025
Navigating the Fundraising Landscape to Raise $1.2M with Toby Egbuna | Inside the Round
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, sharing personal experiences and insights on navigating the venture capital landscape. They discuss the importance of adapting pitches, learning from failures, and the mental fortitude required to persist in fundraising efforts. The dialogue also touches on the challenges faced by underrepresented founders and offers advice on how to approach fundraising strategically. The speakers emphasize the need for a shift in how resources are allocated to ensure equitable opportunities for all entrepreneurs.
Takeaways
The biggest mistake in fundraising is not having a process.
Winning the NPR grant was a pivotal moment for Chezie.
Toby believes Chezie did not need venture capital to succeed.
Community support is vital for founders to combat loneliness.
Building relationships with other founders is essential.
The journey of being a founder is unique and challenging.
Finding your stride takes time and experience.
Pivotal moments can redefine your fundraising strategy.
Pitching on vision can be more effective than traction.
Fundraising is a marathon without a clear finish line.
Feedback from investors can be misleading; focus on the no.
Preparation is key before approaching investors.
Consider if you genuinely need venture capital before raising.
Warm introductions can create barriers for underrepresented founders.
AI is reducing barriers for aspiring entrepreneurs.
Chapters
00:00 The Fundraising Process: Key Mistakes to Avoid
02:51 Co-Founder Dynamics: Sibling Relationships in Business
06:03 Taking the Leap: Going Full-Time as a Founder
08:47 Understanding VC Funding: Is It Necessary?
12:01 Navigating Grants: A Path to Funding
15:03 Building a Supportive Community as a Founder
18:10 The Unique Journey of Being a Founder
19:08 Learning the Ropes of Fundraising
22:41 Navigating the Fundraising Landscape
23:01 The Journey of Raising Capital
24:11 Learning Through Experience
25:30 Pivotal Moments in Fundraising
29:12 Challenges in Closing the Round
30:14 The Marathon of Fundraising
32:23 Investor Conversations and Feedback
34:06 Advice for Aspiring Founders
35:54 Changing the Game for Underrepresented Founders
37:48 Post-Fundraising Reflections
39:23 Maintaining Mental and Physical Health
41:50 Empowering Future Entrepreneurs
Find Toby here: https://www.linkedin.com/in/toby-egbuna/ (https://www.linkedin.com/in/toby-egbuna/)
Find Helena here: https://www.linkedin.com/in/helenafogarty/ (https://www.linkedin.com/in/helenafogarty/)
Follow us:LinkedIn (https://www.linkedin.com/company/bamboo-crowd/): https://www.linkedin.com/company/bamboo-crowd/ (https://www.linkedin.com/company/bamboo-crowd/)
Spotify (https://open.spotify.com/show/5NVE9AhSS5LGb6iepeZW3o): <a href="https://open.spotify.com/show/5NVE9AhSS5LGb6iepeZW3o"...
8 Apr 2025
From Rejection to Resilience: A Startup Journey with David Dellapelle | Inside the Round EP 1
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; embrace it.
Building relationships with investors is crucial for success.
Focus on solving real problems for customers.
Resilience is developed through adversity.
The fundraising process requires learning from failures.
It's important to maintain a balance between personal and professional life.
Providing value should be the primary goal for founders.
The startup journey is akin to a video game; you level up with each challenge.
Transparency and authenticity can strengthen investor relationships.
Chapters
00:00 The Journey Begins: Overcoming Initial Challenges
02:52 Identifying the Core Problem in Cybersecurity
05:59 The Founding Story: From Idea to Execution
08:56 Navigating the VC Landscape: Lessons Learned
11:57 The Importance of Customer Feedback
14:57 Resilience in the Face of Rejection
17:47 Building Relationships with Investors
20:48 The Fundraising Process: Strategies and Insights
23:49 Post-Funding: Responsibilities and Growth
27:09 Maintaining Balance: Personal vs. Professional Life
30:10 Advice for Aspiring Founders: Focus on Value Creation
Find David here: https://www.linkedin.com/in/daviddellapelle/ (https://www.linkedin.com/in/daviddellapelle/)
Find Helena here: https://www.linkedin.com/in/helenafogarty/ (https://www.linkedin.com/in/helenafogarty/)
Follow us: (https://www.linkedin.com/company/bamboo-crowd/)
LinkedIn (https://www.linkedin.com/company/bamboo-crowd/)
Spotify (https://open.spotify.com/show/5NVE9AhSS5LGb6iepeZW3o)
Learn more about BTG: https://bambootalent.group/ (https://bambootalent.group/)
Who has been a guest on Inside the Round
Names identified in recent episode analyses. Showing up to five guests.
Hailey Swartz
Steve Gilman
Natalie Schneider
Sumeet Shah
Amy Kiska
Podcast Authority Score: 12 / 100
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