Confessions, Connections, and Capital: Inside Strive's First Huddle

For our first Strive "Huddle" session, Strivers turned up to get answers on the spot about raising investment for a myriad of ventures at different stages.
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Strivers were seeking fundraising advice for: an adventure app, a one-woman theatre show, a boutique hotel, a services company eyeing an exit, a design studio, and a founder rebuilding after a hurricane.

Ilana Golan led the session, drawing on years as an engineer and exec, a run of IPOs and acquisitions, and stakes in over a hundred startups.

What kept coming up

  • Raise for a reason, not because everyone else is. Noah shared a noticeable trend from entrepreneurs he meets, which is that sometimes founders raise for status rather than need.
  • AI is changing the fundraising landscape. With so much potential to use vibecoding (the practice of building software mostly through natural-language prompts to an AI coding tool, rather than writing code by hand line-by-line) more and more founders are turning to bootstrapping rather than VC money. 
  • Your network is your net worth. Two Strivers left with live introductions, made right there in the room.
  • Hype matters. The single way to gain investor attention is to make them feel they will be missing out on something if they don’t jump in. Ensure your gaining eyes on your venture in the right rooms, such as speaking at conferences on podcasts.

Book recommendation: Ilana recommended Confessions of a Unicorn Founder for anyone still chewing on the bootstrap-versus-raise question.

What made the Huddle great?

1. Strivers sharing openly where they are on their personal journey and learning from where others are on theirs

2. Gaining peer support from epic Strivers

3. Walking away with bespoke advice from an expert from The Strive Collective 

What would you like the next Strive Huddle to be on? 

Whether it's how to raise champion racehorses, climb Everest, or scale your company, there's bound to be a Striver who can give you advice!

Pillar:
Growth

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