Navigating Bootstrapper Funding and Investment Structures

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The chapter delves into negotiating bootstrapper funding, particularly focusing on simplifying investment structures like Simple Agreement for Future Equity (SAFE) and the Shared Earnings Agreement (SEAL) to reduce friction and increase adoption. It highlights the importance of standard terms in contracts, explains the process of converting safes into preferred equity, and emphasizes the need for compatibility and alignment between bootstrappers and investors to maintain optionality and flexibility for entrepreneurs.

A few months ago, I raised a low 6-figure investment for Podscan. Here's the conversation between me and my investor, @tylertringas, that happened just before I signed the contract.

You usually don't get to listen in for one of those. Today, you will.

Tyler and I discuss how the Calm Company Fund navigates the alignment challenge between founders and investors, what makes a business like Podscan investable, and the risks of funding a portfolio of niche bootstrapped businesses.

Tyler on X: https://x.com/tylertringas

00:00:00 Bootstrapper-Compatible Funding
00:06:23 Profit Sharing and Standardizing Investment Agreements
00:12:53 Investor-Founder Alignment & Site Projects
00:22:30 Side Project Management in Investments
00:28:18 Early Stage Financing Investment Considerations
00:40:50 Valuation and Investment Strategy Art
00:48:19 Entrepreneurial Collaboration and Forward Planning

This episode is sponsored by Acquire.com

The blog post: https://thebootstrappedfounder.com/negotiating-bootstrapper-funding-with-tyler-tringas/

The podcast episode: https://tbf.fm/episodes/328-negotiating-bootstrapper-funding-with-tyler-tringas

You'll find my weekly article on my blog: https://thebootstrappedfounder.com

Podcast: https://thebootstrappedfounder.com/podcast

Newsletter: https://thebootstrappedfounder.com/newsletter

My book Zero to Sold: https://zerotosold.com/

My book The Embedded Entrepreneur: https://embeddedentrepreneur.com/

My course Find Your Following: https://findyourfollowing.com

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