To Success

263 | Handling Chaos & Fundraising Tips with Brennan Woodruff from

  1. ✅ Choosing Your Path: Brennan Woodruff reflects on his transition from a demanding role at SoftBank to co-founding, realizing he had the power to choose his own journey, including embracing the beautiful chaos of entrepreneurship.
  2. ✅ Handling Chaos: Woodruff discusses the various layers of chaos in entrepreneurship, including internal self-doubt, learning with a first-time founder team, and external demands from customers, emphasizing that embracing this beautiful chaos is part of the entrepreneurial journey.
  3. ✅ Importance of Networks: Woodruff highlights the significance of networks in his entrepreneurial journey and how networks, serendipity, and the right timing led him to co-founding, offering advice for startup founders on approaching fundraising and investor relationships.

Episode Summary:

In episode 263, Brennan Woodruff, co-founder of, shares his journey from a high-performing role at SoftBank to the world of entrepreneurship, emphasizing the power of choice. He recalls a pivotal moment when he realized he was choosing the chaos of his work environment and the underappreciation he faced. This awakening prompted him to make the beautiful choice of pursuing his own path by co-founding, an AI marketing assistant.

Woodruff discusses the layers of chaos encountered in entrepreneurship, including internal self-doubt, the learning curve of a first-time founder team, and the external demands of customers. He highlights the appeal of this beautiful chaos, which keeps the journey exciting.

Woodruff also underscores the importance of networks in entrepreneurship and offers valuable advice for startup founders. He encourages founders to view fundraising as a two-way partnership and suggests that simple agreements for future equity (Safes) can be a beneficial approach for raising capital. He also advises founders to tap into their existing networks for early-stage financing and to seek other ways to finance their startups before considering institutional venture capital.

This episode offers actionable insights for founders, emphasizing the need for practical advice and guidance in the challenging world of startups.


00:00 Intro

00:11 Brennan's Journey to

01:44 The New Chaos: Transitioning to Entrepreneurship

03:25 Brennan's Career Path and Comfort in Chaos

04:14 The Birth of GoCharlie: A Serendipitous Opportunity

05:00 First Steps into Entrepreneurship and the Weight of Responsibility

05:32 Capital Understanding and Fundraising Advice for Startups

07:18 Understanding SAFE: A Simple Agreement for Future Equity

09:20 Connecting with

#Entrepreneurship #Choice #BeautifulChaos #StartupInsights #Fundraising #Networks #Safes #FirstTimeFounders

Entrepreneurship, choice, beautiful chaos, startup insights, fundraising, networks, Safes, first-time founders, Brennan Woodruff,, self-doubt, learning curve, external demands, power of choice, venture capital.

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