Starting & Sustaining

https://images.fireside.fm/podcasts/images/6/606af8cb-26ad-432e-ac89-a5866ab5af76/cover.jpg

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.

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Website
https://startsustain.fireside.fm/
Description
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.
Language
🇬🇧 English
last modified
2019-05-28 03:54
last episode published
2018-08-14 14:00
publication frequency
26.15 days
Contributors
Garrett Dimon author  
Garrett Dimon owner  
Explicit
false
Number of Episodes
24
Rss-Feeds
Detail page
Categories
Technology Business Management & Marketing Software How-To

Recommendations


Episodes

Date Thumb Title & Description Contributors
14.08.2018 https://images.fireside.fm/podcasts/images/6/606af8cb-26ad-432e-ac89-a5866ab5af76/cover.jpg

Brennan Dunn, Co-founder of RightMessage

Brennan and I explore the trajectory of businesses and learning that led him to create RightMessage. Since founding his first SaaS application, Planscope, in 2011. Brennan began producing courses to help freelancers grow their business as a way to grow...
Garrett Dimon author
31.07.2018 https://images.fireside.fm/podcasts/images/6/606af8cb-26ad-432e-ac89-a5866ab5af76/cover.jpg

Mathias Meyer, Co-founder and Former CEO of Travis CI

After helping found Travis CI and grow into the CEO role over six years, Mathias recently left Travis and starting helping other companies with their growth challenges. We talked about the difficulty of leaving and moving on after six years and the tac...
Garrett Dimon author
17.07.2018 https://images.fireside.fm/podcasts/images/6/606af8cb-26ad-432e-ac89-a5866ab5af76/cover.jpg

Jaimee Newberry, Co-founder of Picture This Clothing

Picture This Clothing went viral immediately. From the outside, it looked like every entrepreneur's dream. But the reality of holding together a business that just went viral is completely different. Add in the logistics of printng custom shirts on dem...
Garrett Dimon author
10.07.2018 https://images.fireside.fm/podcasts/images/6/606af8cb-26ad-432e-ac89-a5866ab5af76/cover.jpg

Steve McLeod, Founder of Feature Upvote

Garrett Dimon author
9.10.2017

Ben Curtis, Co-founder of Honeybadger

Ben and I discuss the origins of Honeybadger, what it's like bootstrapping, and the sleepless nights brought on by running an infrastructure product. We also talk about Ben's experiences automating the company and growing it into a more mature and resi...
Garrett Dimon author
13.08.2017

Scott Nixon - Co-founder of Happy Herbivore/Meal Mentor

Scott and I discuss the hybrid nature of running a business where software merely facilitates a primarily offline interaction. How do you measure engagement? How do you know if the customer succeeds? He makes a great case for giving consumer-oriented s...
Garrett Dimon author
16.06.2017

Matt Goldman, CEO of Churn Buster

Matt and I talk about running a SaaS business after acquiring it, the mistakes they made early after taking over Churn Buster, and the common ways that SaaS businesses get dunning wrong and how they can do better. We also dive into what it's like to ac...
Garrett Dimon author
9.06.2017

Rachel Andrew, Cofounder of Perch

Rachel and I talk about what it's like supporting self-hosted software, juggling a busy travel schedule to make time for work. She's been working on Perch with her husband Drew for eight years, and they're still going strong. Special Guest: Rachel Andr...
Garrett Dimon author
2.06.2017

Tracy Osborn, Founder of Wedding Lovely

Tracy and I talk about her experience building and running Wedding Lovely, raising some funding for it, losing a co-founder, and even going through a heart-breaking acquisition process with Etsy. Through it all, she's kept going and even published book...
Garrett Dimon author
25.05.2017

Josh Williams, Founder of Gowalla

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 ...
Garrett Dimon author
19.05.2017

Thomas Smale, Founder of FE International

Recently I sat down this Thomas Smale of FE International. Thomas and FE International helped me sell Sifter and made the whole process seem easy. After selling so many online businesses, FE International has the process down to a science, and they've ...
Garrett Dimon author
25.04.2017

Nathan Barry, Founder of ConvertKit

Nathan and I talk about the early days of ConvertKit, reaching a point where he had to make a decision to invest more significantly in it or walk away. He invested a significant portion of his income from other projects and really doubled down to make ...
Garrett Dimon author
30.03.2017

Courtland Allen, Founder of Indie Hackers

Courtland's story is great because he's been on a bit of the roller coaster, and now he's starting fresh with Indie Hackers. He's interviewing other founders of businesses of all sizes and helping to shed light on what's possible for small independent ...
Garrett Dimon author
26.02.2017

Ruben Gamez, Founder of Bidsketch

Ruben's story with Bidsketch is a great example of how a simple small business can grow into something healthy sustainable on a reasonable timeline. He started out simply with very little in the way of expectations, and bootstrapped the business to pro...
Garrett Dimon author
3.02.2017

Allan Branch, Cofounder of Less Accounting

During a time when seemingly everyone is trying to build a product and move away from consulting, Allan is doing just the opposite and moving from SaaS and recurring revenue back to good old-fashioned consulting. We talk a little about the process of s...
Garrett Dimon author
28.01.2017

Drew Wilson, Founder of Plasso

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...
Garrett Dimon author
15.01.2017

Josh Pigford, Founder of Baremetrics

Josh and I discussed bootstrapping, accepting outside money, the drawbacks of hiring too fast and having to ask his team to take a pay cut. We also talk about how metrics simply aren't important in the early days and how nothing beats spending time to ...
Garrett Dimon author
6.01.2017

Natalie Nagele, CEO of Wildbit

Natalie and I talk about bootstrapping, learning that marketing is a necessary part of growing a software company, and the transitions that led Wildbit to be a family-focused company. We touched on the benefits and challenges of running a multi-product...
Garrett Dimon author
29.12.2016

JD Graffam, Serial Acquirer of SaaS Apps

JD and I talk about buying and selling SaaS applications and share some details from the process of selling and transferring Sifter. JD shares what it's like juggling multiple businesses and how he makes it work, and he dives into the attributes and in...
Garrett Dimon author
28.12.2016

Tyler Rooney, Cofounder and CPO of Format

Format had seven people on the payroll before Tyler even got paid. We talk about bootstrapping in Canada, the amazing story of how they acquired the Format.com domain name, and what it's like transitioning from a survival mentality to a growth mentali...
Garrett Dimon author
26.12.2016

Peldi, Founder of Balsamiq

Peldi and I talk about moving from California to Italy to lower his cost of living to start a company, juggling different delivery formats for software (and the associated payments challenges), giving amazing support, and bending over backwards to help...
Garrett Dimon author
24.12.2016

Pat Allan, Creator of Thinking Sphinx and Flying Sphinx

Pat Allan turned his open source side project into a profitable Heroku Add-on. We talk about the advantages and disadvantages of building on another company's platforms, doing support for both open source users and paying customers, and some of the tri...
Garrett Dimon author
22.12.2016

Anthony Eden, Founder of DNSimple

Anthony built DNSimple on the side and didn't come on board full-time until after there were two other full-time employees. We discussed some of the advantages and disadvantages of running a complex infrastructure product, marketing a complicated busin...
Garrett Dimon author
21.12.2016

Mike Perham, Creator of Sidekiq and Inspeqtor

Mike Perham has successfully built a wildly profitable one-man business built on his open source efforts. We discuss what it's like balancing the seemingly opposing forces of open source and a for-profit business, managing support for the open source v...
Garrett Dimon author