Negotiating Bootstrapper Funding with Tyler Tringas — The Bootstrapped Founder 326


Dear founder,

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.

Check out Podscan.fm! It's my media monitoring service that tracks every mention of you and your brand across all podcasts. Discover where your name pops up in the podcast world.

(And if you're a builder, the Podscan API allows access to fully transcribed episodes for millions of podcasts!)


Thank you for checking out this week’s interview edition of The Bootstrapped Founder. Did you enjoy it? If so, please spread the word and ​share this issue on Twitter.

To make sure you keep getting your weekly dose of Bootstrapped Founder, please add arvid@thebootstrappedfounder.com to your address book or whitelist us.

Did someone forward you this issue of The Bootstrapped Founder? ​You can subscribe to it here!​

Want to change which emails you get from The Bootstrapped Founder or unsubscribe for good? No worries, just click this link: ​change email preferences​ or ​unsubscribe​​.

Our postal address: 113 Cherry St #92768, Seattle, WA 98104-2205

Opt-out of preference-based advertising

Arvid Kahl

Being your own boss isn't easy, but it's worth it. Learn how to build a legacy while being kind and authentic. I want to empower as many entrepreneurs as possible to help themselves (and those they choose to serve).

Read more from Arvid Kahl

Podcast, YouTube, Blog Dear founder, I’ve been talking a lot about Podscan and the positive developments—the improvements, the good things that have happened to the company and to me over the last year and a half since I started this journey. But building in public is about sharing the ups and the downs, the wild joy ride and roller coaster that is entrepreneurship. And it’s time to share the not-so-happy parts of this business. Recently, I announced that Podscan was profitable. And it...

Podcast, YouTube, Blog Dear founder, Jack Friks (@jackfriks) is the founder of PostBridge, a social media scheduling tool that grew from his own frustration with spending hours posting across platforms to a $18k/month business. We explore the evolution of social media toward authenticity, the challenges of building lean products as a solopreneur, and how to navigate the noise while maintaining a genuine human connection in an AI-driven world. THE BOOTSTRAPPED FOUNDER • EPISODE 396 396: Jack...

Podcast, YouTube, Blog Dear founder, If you're into PHP, Laravel, and how Taylor Otwell turned an open-source framework into a thriving multi-million dollar empire, check out this week's interview episode of my podcast! There’s something deeply unsettling about being dramatically more productive while feeling like you’re barely working. That’s the strange dichotomy I find myself in every day now with AI-assisted coding. My output has multiplied significantly over the last few months, yet I...