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
Bootstrapped Founder Logo

Podcast, YouTube, Blog Dear founder, This week taught me an unexpected lesson about entrepreneurship. After the Christmas and New Years festivities — that annual tradition of sharing joy, memories, and apparently germs — I found myself running a fever of nearly 40°C (104°F). For someone who rarely gets sick, this hit particularly hard. 🎧 Listen to this on my podcast. As I lay in bed, barely able to function, I realized just how crucial it had been to build my businesses the way I did. Both my...

Bootstrapped Founder Logo

Podcast, YouTube, Blog Dear founder, When Peter Jackson was brainstorming the Lord of the Rings movie universe, two amazing Tolkien-savvy illustrators sat in on the meetings: John Howe and Alan Lee. Jackson would explain a scene, what was where, and they would sketch as he talked. When he was done explaining, the two artist would hand over their quick sketches, allowing the director to see what he had just envisioned. Until now, you needed extraordinarily gifted experts with years of...

Bootstrapped Founder Logo

Podcast, YouTube, Blog Dear founder, Johannes Jäschke is a pioneer in the intersection of technology and mental health. From a college seminar to the forefront of digital well-being, Johannes developed Hypnu, a hypnosis app that gained significant traction during the pandemic. His innovative approach offered an alternative to traditional methods, addressing insomnia and anxiety without side effects. After successfully exiting Hypnu, Johannes continues to inspire with his journey through the...