Insights from a portfolio management software CEO who sees the venture market's "healthy shakeup" forcing overdue conversations about profitability and angel group sustainability

Today's episode explores three ideas that caught my attention:

1. The venture market reset is healthy - Alycia embraces the current volatility as necessary medicine. It challenges the trope that stability is always preferable - perhaps occasional chaos forces better investment discipline.
2. Angel group models are evolving - After 20+ years in existence, Alycia questions if the traditional angel group structure still works. I’ve had a lot of conversations recently about the model, and this one definitely got me thinking.
3. Data tracking is hard – Hearing Alycia’s commentary on how even professional fund managers often struggle to locate basic investment documentation was a shock, and reminds me that the venture industry is still, in many ways, in its adolescence.

I explore these ideas and more with Alycia Doxon, CEO of Seraf, a deal flow and portfolio management platform serving angel groups, VCs, and family offices. After raising $27 million as a tech company COO, she acquired Seraf in 2023 through her holding company Harriet Ventures. Alycia brings a unique dual perspective - combining operating experience with deep insight into private market mechanics - giving her a practical view of what's working and broken in early-stage investing.

During our conversation, Alycia shares:

• Data-driven insights on geographic investment trends that challenge the post-COVID narrative about distributed entrepreneurship and explain why physical proximity to innovation hubs still dramatically impacts returns.
• A primer on "safe stacking" where founders can potentially raise multiple rounds without ever converting to equity—highlighting a critical vulnerability in one of the startup ecosystem's most popular investment vehicles.
• Critical due diligence questions most LPs never ask including how fund managers handle administration, accounting, and the surprising number who manage these functions internally despite the operational strain.

Connect with Alycia 

LinkedIn

Stuff We Reference 

• Ron Weissman
• Christopher Mirabile & Ham Lord

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All opinions are personal and may not reflect the views of The Diligent Observer. Not investment advice.