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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 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/

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To learn more about BTG: https://bambootalent.group/  
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