web01.fireside.fm Sun, 19 Apr 2026 07:33:00 -0500 Fireside (https://fireside.fm) Starting & Sustaining - Episodes Tagged with “Saas” https://startingandsustaining.garrettdimon.com/tags/saas Tue, 14 Aug 2018 08:00:00 -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 Brennan Dunn, Co-founder of RightMessage https://startingandsustaining.garrettdimon.com/brennan-dunn 782df01d-b330-4279-b797-3a465b248d2e Tue, 14 Aug 2018 08:00:00 -0600 Garrett Dimon full Garrett Dimon Brennan is a co-founder of Right Message. In this episode, we talk about the path he's taken that led him to create Right Message and what he's learned about building and launching SaaS applications based on his experiences with his various products. 46:36 no 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 Planscope. However, as the content arm of Planscope grew, it became the primary breadwinner. Brennan eventually sold Planscope to focus on the content production with Double Your Freelancing. While optimizing the funnel and learning about the importance of personalization, he began to see the opportunity to create an application that could provide easy-to-use personalization for other businesses. After providing these personalization services in the form of consulting, Brennan recognized that the next step was to use his SaaS experience to create RightMessage. We also touch on the logistics of selling Planscope when it was financially intertwined with Double Your Freelancing. It required significant extra time to extricate the financials and clean up all of the books for the sale. Special Guest: Brennan Dunn. saas, right message, rightmessage, brennan dunn, planscope, double your freelancing 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 Planscope. However, as the content arm of Planscope grew, it became the primary breadwinner.

Brennan eventually sold Planscope to focus on the content production with Double Your Freelancing. While optimizing the funnel and learning about the importance of personalization, he began to see the opportunity to create an application that could provide easy-to-use personalization for other businesses. After providing these personalization services in the form of consulting, Brennan recognized that the next step was to use his SaaS experience to create RightMessage.

We also touch on the logistics of selling Planscope when it was financially intertwined with Double Your Freelancing. It required significant extra time to extricate the financials and clean up all of the books for the sale.

Special Guest: Brennan Dunn.

Sponsored By:

Links:

]]> 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 Planscope. However, as the content arm of Planscope grew, it became the primary breadwinner.

Brennan eventually sold Planscope to focus on the content production with Double Your Freelancing. While optimizing the funnel and learning about the importance of personalization, he began to see the opportunity to create an application that could provide easy-to-use personalization for other businesses. After providing these personalization services in the form of consulting, Brennan recognized that the next step was to use his SaaS experience to create RightMessage.

We also touch on the logistics of selling Planscope when it was financially intertwined with Double Your Freelancing. It required significant extra time to extricate the financials and clean up all of the books for the sale.

Special Guest: Brennan Dunn.

Sponsored By:

Links:

]]> Mathias Meyer, Co-founder and Former CEO of Travis CI https://startingandsustaining.garrettdimon.com/mathias-meyer b6a2412b-9044-4dfc-9926-72fd561a3ffa Tue, 31 Jul 2018 07:00:00 -0600 Garrett Dimon full Garrett Dimon Mathias is one of the original founders of Travis CI. In this episode, we talk about the difficulty of leaving the company he helped start, and the challenges of moving on. 49:28 no 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 tactics that have helped him work through it. We also talk about the operational side of growth. While we all want revenue to grow, sometimes, we fail to think about how that growth affects operations and requires significant attention to the operational side of the business. We also touch on how bootstrapping lends itself to slower and steady growth with a little less stress. We discuss how Travis CI's support of open source projects started out simply as support for the open source community but had the wonderful side effect of great marketing. However, in the case of Travis, scaling to support so many free projects early on wasn't without its own challenges. And we cover some of the challenges of being a german business and doing business internationally while also having a remote team working asynchronously across time zones with nine hours of difference. Special Guest: Mathias Meyer. travis ci, saas, b2b, continuous integration, mathias meyer 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 tactics that have helped him work through it.

We also talk about the operational side of growth. While we all want revenue to grow, sometimes, we fail to think about how that growth affects operations and requires significant attention to the operational side of the business. We also touch on how bootstrapping lends itself to slower and steady growth with a little less stress.

We discuss how Travis CI's support of open source projects started out simply as support for the open source community but had the wonderful side effect of great marketing. However, in the case of Travis, scaling to support so many free projects early on wasn't without its own challenges.

And we cover some of the challenges of being a german business and doing business internationally while also having a remote team working asynchronously across time zones with nine hours of difference.

Special Guest: Mathias Meyer.

Sponsored By:

Links:

]]> 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 tactics that have helped him work through it.

We also talk about the operational side of growth. While we all want revenue to grow, sometimes, we fail to think about how that growth affects operations and requires significant attention to the operational side of the business. We also touch on how bootstrapping lends itself to slower and steady growth with a little less stress.

We discuss how Travis CI's support of open source projects started out simply as support for the open source community but had the wonderful side effect of great marketing. However, in the case of Travis, scaling to support so many free projects early on wasn't without its own challenges.

And we cover some of the challenges of being a german business and doing business internationally while also having a remote team working asynchronously across time zones with nine hours of difference.

Special Guest: Mathias Meyer.

Sponsored By:

Links:

]]> Jaimee Newberry, Co-founder of Picture This Clothing https://startingandsustaining.garrettdimon.com/jaimee-newberry 528de475-f777-4f46-88a9-1d7a0777f355 Tue, 17 Jul 2018 08:00:00 -0600 Garrett Dimon full Garrett Dimon Jaimee Newberry is the founder of Picture This Clothing where you can print a coloring sheet and design a one-of-a-kind ready-to-wear creation that they send to you. In this epsode we talk about making hard decisions and creating space in your life for ideas to take hold and give you time to work on them. 41:52 no 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 demand and fulfilling the orders, and it's not all it's cracked up to be. Jaimee and I talk about the necessity of creating space in your life for opportunities to take hold. We explore what it's like running a fledgling business while experiencing viral growth as well as what happens after the viral growth subsides. We dive into what it's like getting viral traffic but not actually making any sales for the first week. We also talk about the importance of launching before you're ready, validating your idea, and making sure to see projects through and not leave them unfinished. Special Guest: Jaimee Newberry. 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 demand and fulfilling the orders, and it's not all it's cracked up to be.

Jaimee and I talk about the necessity of creating space in your life for opportunities to take hold. We explore what it's like running a fledgling business while experiencing viral growth as well as what happens after the viral growth subsides. We dive into what it's like getting viral traffic but not actually making any sales for the first week.

We also talk about the importance of launching before you're ready, validating your idea, and making sure to see projects through and not leave them unfinished.

Special Guest: Jaimee Newberry.

Sponsored By:

Links:

]]> 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 demand and fulfilling the orders, and it's not all it's cracked up to be.

Jaimee and I talk about the necessity of creating space in your life for opportunities to take hold. We explore what it's like running a fledgling business while experiencing viral growth as well as what happens after the viral growth subsides. We dive into what it's like getting viral traffic but not actually making any sales for the first week.

We also talk about the importance of launching before you're ready, validating your idea, and making sure to see projects through and not leave them unfinished.

Special Guest: Jaimee Newberry.

Sponsored By:

Links:

]]> Steve McLeod, Founder of Feature Upvote https://startingandsustaining.garrettdimon.com/steve-mcleod 192f04d9-8fba-4fc1-9ba1-06b539a7c74b Tue, 10 Jul 2018 06:00:00 -0600 Garrett Dimon full Garrett Dimon Steve McLeod is the founder of Feature Upvote, a SaaS tool to enable your customers to suggest and upvote improvements. In this episode, we talk about and compare his experiences running both a B2C app and B2B app and the value of having a part-time system administrator on retainer. 38:18 no After years running a company based on a consumer product, Steve made the decision to switch to a business-focused product in Feature Upvote, and he's never looked back. We explore the implications of legal changes having the ability to wipe out 55% of your customer base after the United States changed the laws around online gambling. We compare the differences between Steve's B2C and B2B experiences, the ability to make a healthy living working 6 hours a day but making you sure you're consistent and show up every day. We also discuss the value of enlisting the services of outside experts like a system administrator as soon as you can afford them. We also touch on the challenges of managing spam and fraud as a business grows and becomes increasingly visible and the importance of thinking up front about what kind of business you want and the type of customers you want to serve. Special Guest: Steve McLeod. saas, b2b, b2c, feature upvote After years running a company based on a consumer product, Steve made the decision to switch to a business-focused product in Feature Upvote, and he's never looked back. We explore the implications of legal changes having the ability to wipe out 55% of your customer base after the United States changed the laws around online gambling.

We compare the differences between Steve's B2C and B2B experiences, the ability to make a healthy living working 6 hours a day but making you sure you're consistent and show up every day. We also discuss the value of enlisting the services of outside experts like a system administrator as soon as you can afford them.

We also touch on the challenges of managing spam and fraud as a business grows and becomes increasingly visible and the importance of thinking up front about what kind of business you want and the type of customers you want to serve.

Special Guest: Steve McLeod.

Sponsored By:

Links:

]]> After years running a company based on a consumer product, Steve made the decision to switch to a business-focused product in Feature Upvote, and he's never looked back. We explore the implications of legal changes having the ability to wipe out 55% of your customer base after the United States changed the laws around online gambling.

We compare the differences between Steve's B2C and B2B experiences, the ability to make a healthy living working 6 hours a day but making you sure you're consistent and show up every day. We also discuss the value of enlisting the services of outside experts like a system administrator as soon as you can afford them.

We also touch on the challenges of managing spam and fraud as a business grows and becomes increasingly visible and the importance of thinking up front about what kind of business you want and the type of customers you want to serve.

Special Guest: Steve McLeod.

Sponsored By:

Links:

]]> Ben Curtis, Co-founder of Honeybadger https://startingandsustaining.garrettdimon.com/ben-curtis d2163b1d-6794-4afb-b7bb-f0c4e74a9a54 Mon, 09 Oct 2017 07:00:00 -0600 Garrett Dimon full Garrett Dimon Ben Curtis is the co-founder of Honeybadger, a SaaS-based exception tracking application. Honeybadger is bootstrapped and profitable with three co-founders and is a great example of a team scratching their own itch. 37:18 no 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 resilient business. Special Guest: Ben Curtis. 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 resilient business.

Special Guest: Ben Curtis.

Sponsored By:

Links:

]]> 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 resilient business.

Special Guest: Ben Curtis.

Sponsored By:

Links:

]]> Scott Nixon - Co-founder of Happy Herbivore/Meal Mentor https://startingandsustaining.garrettdimon.com/scott-nixon 804793dc-414b-4d0f-b506-92a8320f1f13 Sat, 12 Aug 2017 23:00:00 -0600 Garrett Dimon full Garrett Dimon Scott Nixon is the co-founder of Meal Mentor, a subscription-based vegeterian meal planning service. Scott handles the technology side of the business and works to keep the operational side of things humming with software. 52:46 no 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 software businesses another chance. Sure they have high-churn, but there's also many more consumers out there than businesses. Special Guest: Scott Nixon. 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 software businesses another chance. Sure they have high-churn, but there's also many more consumers out there than businesses.

Special Guest: Scott Nixon.

Sponsored By:

Links:

]]> 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 software businesses another chance. Sure they have high-churn, but there's also many more consumers out there than businesses.

Special Guest: Scott Nixon.

Sponsored By:

Links:

]]> 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:

]]> Thomas Smale, Founder of FE International https://startingandsustaining.garrettdimon.com/thomas-smale cbec0411-cba7-4918-aa7d-aa0110bce044 Thu, 18 May 2017 23:00:00 -0600 Garrett Dimon full Garrett Dimon Thomas Smale is the founder of FE International, a professional web site broker. FE International helped me sell Sifter in 2016, and they were a fantastic partner. Having sold over 425 business, they definitely know what they're doing, and Thomas has an incredible amount of wisdom to share around buying and selling online businesses. 35:01 no 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 been able to pick up on quite a few trends. So Thomas takes some time to share what they've seen and what matters when it comes to buying or selling an online business. Special Guest: Thomas Smale. 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 been able to pick up on quite a few trends. So Thomas takes some time to share what they've seen and what matters when it comes to buying or selling an online business.

Special Guest: Thomas Smale.

Sponsored By:

Links:

]]> 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 been able to pick up on quite a few trends. So Thomas takes some time to share what they've seen and what matters when it comes to buying or selling an online business.

Special Guest: Thomas Smale.

Sponsored By:

Links:

]]> Nathan Barry, Founder of ConvertKit https://startingandsustaining.garrettdimon.com/nathan-barry 0f885e70-a533-43c1-9225-b10bd21f9180 Tue, 25 Apr 2017 09:00:00 -0600 Garrett Dimon full Garrett Dimon The journey Nathan has gone through with ConvertKit is amazing. From significantly missing his original goals, he continued to work and make adjustments to ConvertKit and his approach until he found the sweet spot. Since then, ConvertKit has grown incredibly fast, and Nathan's been openly sharing everything he's learned throughout the journey. 47:51 no 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 it work long before it was obvious things were going to take off. He talks about his sales process and how it simultaneously helped him better understand the needs of potential customers as well as build a relationship and find his first customers. Special Guest: Nathan Barry. 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 it work long before it was obvious things were going to take off. He talks about his sales process and how it simultaneously helped him better understand the needs of potential customers as well as build a relationship and find his first customers.

Special Guest: Nathan Barry.

Sponsored By:

Links:

]]> 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 it work long before it was obvious things were going to take off. He talks about his sales process and how it simultaneously helped him better understand the needs of potential customers as well as build a relationship and find his first customers.

Special Guest: Nathan Barry.

Sponsored By:

Links:

]]> Courtland Allen, Founder of Indie Hackers https://startingandsustaining.garrettdimon.com/courtland-allen 3c1ba33d-7602-466b-a97d-27557087550d Thu, 30 Mar 2017 10:00:00 -0600 Garrett Dimon full Garrett Dimon Courtland is earlier on in the cycle of building a business, but he's on the right track. He's gained a ton of insight from past experiences, and now he's building Indie Hackers and talking to a plethora of other small businesses about what has and hasn't worked for them. 32:22 no 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 software-based businesses. At the same time, the stories are also grounded in realistic stories of slow growth and hard work instead of just focusing on those businesses that hit the jackpot. Courtland's past experience combined with his discussions with other founders has given him some great perspective and insight on what works and doesn't work for small software businesses. Special Guest: Courtland Allen. 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 software-based businesses. At the same time, the stories are also grounded in realistic stories of slow growth and hard work instead of just focusing on those businesses that hit the jackpot. Courtland's past experience combined with his discussions with other founders has given him some great perspective and insight on what works and doesn't work for small software businesses.

Special Guest: Courtland Allen.

Sponsored By:

Links:

]]> 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 software-based businesses. At the same time, the stories are also grounded in realistic stories of slow growth and hard work instead of just focusing on those businesses that hit the jackpot. Courtland's past experience combined with his discussions with other founders has given him some great perspective and insight on what works and doesn't work for small software businesses.

Special Guest: Courtland Allen.

Sponsored By:

Links:

]]> Ruben Gamez, Founder of Bidsketch https://startingandsustaining.garrettdimon.com/ruben-gamez 14d6afe8-bc9d-494a-b9e0-c5cae8e9036e Sun, 26 Feb 2017 15:00:00 -0700 Garrett Dimon full Garrett Dimon Ruben set out to help a friend find some software for proposals and, when he couldn't find anything, just built it himself in 2009. Eight short years later, and he's built a 5-person remote team working on it. 41:57 no 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 profitability it on the side of a full-time job and now manages a remote team of four additional people. We talk about the challenges of growing and managing a remote team as an introvert, the process of recovering after he accidentally deleted all of the customer billing data, and much more. Special Guest: Ruben Gamez. 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 profitability it on the side of a full-time job and now manages a remote team of four additional people. We talk about the challenges of growing and managing a remote team as an introvert, the process of recovering after he accidentally deleted all of the customer billing data, and much more.

Special Guest: Ruben Gamez.

Sponsored By:

Links:

]]> 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 profitability it on the side of a full-time job and now manages a remote team of four additional people. We talk about the challenges of growing and managing a remote team as an introvert, the process of recovering after he accidentally deleted all of the customer billing data, and much more.

Special Guest: Ruben Gamez.

Sponsored By:

Links:

]]> Allan Branch, Cofounder of Less Accounting https://startingandsustaining.garrettdimon.com/allan-branch 4aa6dd34-7119-4998-b0f2-3633bc050ad7 Thu, 02 Feb 2017 20:00:00 -0700 Garrett Dimon full Garrett Dimon Allan is the cofounder of LessEverying, makers of LessAccounting. They recently sold LessAccounting and are moving back into traditional consulting and having a blast with it. 33:31 no 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 selling LessAccounting, the ups downs of trying to grow a SaaS application, and some ways to take a step back and make sure that you're working on things you're passionate about. Special Guest: Allan Branch. 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 selling LessAccounting, the ups downs of trying to grow a SaaS application, and some ways to take a step back and make sure that you're working on things you're passionate about.

Special Guest: Allan Branch.

Sponsored By:

Links:

]]> 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 selling LessAccounting, the ups downs of trying to grow a SaaS application, and some ways to take a step back and make sure that you're working on things you're passionate about.

Special Guest: Allan Branch.

Sponsored By:

Links:

]]> Natalie Nagele, CEO of Wildbit https://startingandsustaining.garrettdimon.com/natalie-nagele c43f53a0-aa32-4b82-81bd-1d50f2dc61cb Fri, 06 Jan 2017 07:00:00 -0700 Garrett Dimon full Garrett Dimon Natalie is the CEO of Wildbit, makers of Postmark, Beanstalk, and DeployBot, and it's where I work full-time these days. 37:38 no 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 company, the inspiration for the various products, and the difficulties of hanging in there as a business gets older and the responsibilities grow and change. Special Guest: Natalie Nagele. 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 company, the inspiration for the various products, and the difficulties of hanging in there as a business gets older and the responsibilities grow and change.

Special Guest: Natalie Nagele.

Sponsored By:

Links:

]]> 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 company, the inspiration for the various products, and the difficulties of hanging in there as a business gets older and the responsibilities grow and change.

Special Guest: Natalie Nagele.

Sponsored By:

Links:

]]> JD Graffam, Serial Acquirer of SaaS Apps https://startingandsustaining.garrettdimon.com/jd-graffam afb5a3e9-7320-4537-aac9-9a6c0689ec66 Thu, 29 Dec 2016 06:00:00 -0700 Garrett Dimon full Garrett Dimon JD Graffam runs multiple agencies and SaaS applications, including Sifter, which he acquired from me in Spring of 2016. 50:02 no 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 insights he uses to decide whether a SaaS application is a good opportunity or not and how he does business a bit differently. This is an episode that's near and dear because I feel like it shares some of the less-often seen aspects of transactions like selling businesses. I really hope you enjoy it. Special Guest: JD Graffam. 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 insights he uses to decide whether a SaaS application is a good opportunity or not and how he does business a bit differently. This is an episode that's near and dear because I feel like it shares some of the less-often seen aspects of transactions like selling businesses. I really hope you enjoy it.

Special Guest: JD Graffam.

Sponsored By:

Links:

]]> 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 insights he uses to decide whether a SaaS application is a good opportunity or not and how he does business a bit differently. This is an episode that's near and dear because I feel like it shares some of the less-often seen aspects of transactions like selling businesses. I really hope you enjoy it.

Special Guest: JD Graffam.

Sponsored By:

Links:

]]> Tyler Rooney, Cofounder and CPO of Format https://startingandsustaining.garrettdimon.com/tyler-rooney 2791db28-40e9-4531-9c05-c3f4ce9ede40 Wed, 28 Dec 2016 06:00:00 -0700 Garrett Dimon full Garrett Dimon Tyler Rooney is the Cofounder of Format.com, a portfolio hosting service based in Canada. 48:08 no 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 mentality as a business grows. Special Guest: Tyler Rooney. 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 mentality as a business grows.

Special Guest: Tyler Rooney.

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]]> 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 mentality as a business grows.

Special Guest: Tyler Rooney.

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]]> Peldi, Founder of Balsamiq https://startingandsustaining.garrettdimon.com/peldi-balsamiq c5766e7e-d53e-4d76-a9e9-7fc153bf4380 Mon, 26 Dec 2016 06:00:00 -0700 Garrett Dimon full Garrett Dimon Peldi originally set out to create a wireframing plugin for Jira but ultimately ended up creating a tiny empire of wireframing tools via plugins, downloadable software, and more recently SaaS. 36:07 no 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 customers. While he originally didn't want to grow the business beyond himself, Balsamiq is now a team of 23 people based all around the world. Special Guest: Giacomo “Peldi” Guilizzoni. 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 customers. While he originally didn't want to grow the business beyond himself, Balsamiq is now a team of 23 people based all around the world.

Special Guest: Giacomo “Peldi” Guilizzoni.

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]]> 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 customers. While he originally didn't want to grow the business beyond himself, Balsamiq is now a team of 23 people based all around the world.

Special Guest: Giacomo “Peldi” Guilizzoni.

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]]> Anthony Eden, Founder of DNSimple https://startingandsustaining.garrettdimon.com/anthony-eden c6763c02-e2cc-4e54-a07b-a0ee85f21204 Thu, 22 Dec 2016 06:00:00 -0700 Garrett Dimon full Garrett Dimon Anthony Eden talks about building and running DNSimple, dealing with fraud, and how exhausting it can be running an infrastructure product at times. 33:35 no 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 business with comics, and fighting domain fraud through it all. Special Guest: Anthony Eden. 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 business with comics, and fighting domain fraud through it all.

Special Guest: Anthony Eden.

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]]> 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 business with comics, and fighting domain fraud through it all.

Special Guest: Anthony Eden.

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]]>