web01.fireside.fm Sun, 19 Apr 2026 07:16:33 -0500 Fireside (https://fireside.fm) Starting & Sustaining - Episodes Tagged with “Bootstrapping” https://startingandsustaining.garrettdimon.com/tags/bootstrapping Thu, 25 May 2017 09:00:00 -0600 Starting & Sustaining originally began as a book and spreadsheet (https://get.startingandustaining.com) created to help people start software businesses. That evolved into candid discussions with people involved in software businesses in one way or another. Focused primarily on the trials and tribulations of launching and running a software business, Starting & Sustaining attempts to break down the hurdles to help you build and launch your own software business with less pain and fewer mistakes. en-us episodic Candid discussions with folks involved in and around the SaaS industry. Garrett Dimon Starting & Sustaining originally began as a book and spreadsheet (https://get.startingandustaining.com) created to help people start software businesses. That evolved into candid discussions with people involved in software businesses in one way or another. Focused primarily on the trials and tribulations of launching and running a software business, Starting & Sustaining attempts to break down the hurdles to help you build and launch your own software business with less pain and fewer mistakes. no Garrett Dimon email@garrettdimon.com Josh Williams, Founder of Gowalla https://startingandsustaining.garrettdimon.com/josh-williams c08bc2be-7a86-4339-a21d-deabef27ca9a Thu, 25 May 2017 09:00:00 -0600 Garrett Dimon full Garrett Dimon Josh Williams has done a little bit of everything as far as building software businesses go. He started out bootstrapping some applications which eventually led to raising money and building Gowalla. 54:44 no Josh and I discuss what it's like going from a bootstrapped small team to a team of 30 in a funded startup. We touch on what it's like going from being a lifelong business owner to being an employee of a large corporation experiencing huge growth. And we talk about some of the differences between building a small profitable business and hitching your wagon to venture capital. Simply put, Josh brings some great perspective and deep insight to building and running software businesses. Special Guest: Josh Williams. Josh and I discuss what it's like going from a bootstrapped small team to a team of 30 in a funded startup. We touch on what it's like going from being a lifelong business owner to being an employee of a large corporation experiencing huge growth. And we talk about some of the differences between building a small profitable business and hitching your wagon to venture capital. Simply put, Josh brings some great perspective and deep insight to building and running software businesses.

Special Guest: Josh Williams.

Sponsored By:

Links:

]]> Josh and I discuss what it's like going from a bootstrapped small team to a team of 30 in a funded startup. We touch on what it's like going from being a lifelong business owner to being an employee of a large corporation experiencing huge growth. And we talk about some of the differences between building a small profitable business and hitching your wagon to venture capital. Simply put, Josh brings some great perspective and deep insight to building and running software businesses.

Special Guest: Josh Williams.

Sponsored By:

Links:

]]> Drew Wilson, Founder of Plasso https://startingandsustaining.garrettdimon.com/drew-wilson dd7fe4e1-e14f-40d6-9222-921d96d9993f Sat, 28 Jan 2017 08:45:00 -0700 Garrett Dimon full Garrett Dimon Drew Wilson is a maker at heart. He's created many products with varying degrees of success, but they've all ultimately led him to where he is now, working on Plasso. 39:10 no Drew and I discussed his various projects that led him to create Plasso as well as how successful businesses developed out of years of experimentation and cross-pollination. We also talked about some of the differences with bootstrapping versus raising an angel round through Drew’s experience on both sides. Special Guest: Drew Wilson. Drew and I discussed his various projects that led him to create Plasso as well as how successful businesses developed out of years of experimentation and cross-pollination. We also talked about some of the differences with bootstrapping versus raising an angel round through Drew’s experience on both sides.

Special Guest: Drew Wilson.

Sponsored By:

Links:

]]> Drew and I discussed his various projects that led him to create Plasso as well as how successful businesses developed out of years of experimentation and cross-pollination. We also talked about some of the differences with bootstrapping versus raising an angel round through Drew’s experience on both sides.

Special Guest: Drew Wilson.

Sponsored By:

Links:

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