Welcome to Season 3 of TinySeed Tales, where we follow the founders of one SaaS startup throughout a year as they share their struggles, victories, and failures. On the first episode of Season 3, Rob introduces us to Tony Chan, the cofounder of CloudForecast. CloudForecast is a daily AWS cost monitoring service for busy engineering teams. Tony is one of 33 startup founders from TinySeed’s Spring 2021 accelerator batch. Topics we cover: 2:41- What’s CloudForecast? 4:09- How large is t...
Sep 01, 2022•25 min•Transcript available on Metacast Welcome to Season 3 of TinySeed Tales, where we follow the founders of one SaaS startup throughout a year as they share their struggles, victories, and failures. On the first episode of Season 3, Rob introduces us to Tony Chan, the cofounder of CloudForecast. CloudForecast is a daily AWS cost monitoring service for busy engineering teams. Tony is one of 33 startup founders from TinySeed’s Spring 2021 accelerator batch. Topics we cover: 2:41- What’s CloudForecast? 4:09- How large is the CloudFore...
Sep 01, 2022•25 min•Transcript available on Metacast In episode 618, join Rob Walling as he chats with Sam Dogen, the founder of Financial Samurai, which is one of the longest-running and most popular personal finance blogs. Over the last 13 years, Sam has personally written over 2,500 essays along with a Wall Street Journal Bestselling book. We talk about achieving financial freedom, money mindsets, and relentless execution. Topics we cover: 3:12- The 4% Rule 4:40- Sam’s alternative approach to the 4% Rule 7:25- The FIRE Movemen...
Aug 30, 2022•33 min•Transcript available on Metacast In episode 618, join Rob Walling as he chats with Sam Dogen, the founder of Financial Samurai, which is one of the longest-running and most popular personal finance blogs. Over the last 13 years, Sam has personally written over 2,500 essays along with a Wall Street Journal Bestselling book. We talk about achieving financial freedom, money mindsets, and relentless execution. Topics we cover: 3:12- The 4% Rule 4:40- Sam’s alternative approach to the 4% Rule 7:25- The FIRE Movement 10:16- How to na...
Aug 30, 2022•33 min•Transcript available on Metacast In episode 617, Einar Vollset and Tracy Osborn join Rob Walling for a bootstrapper news roundup episode. They cover a wide range of topics from ProfitWell’s big 200 million exit, spreadsheet mentality, watching an acquirer ruin your company, and much more. Topics we cover: [3:06] What’s your take on ProfitWell’s acquisition? [5:52] Watching an acquirer ruin your company [14:03] The spreadsheet mentality [23:09] If you can’t buy it twice, don’t buy it [36:00] Balanci...
Aug 23, 2022•40 min•Transcript available on Metacast In episode 617, Einar Vollset and Tracy Osborn join Rob Walling for a bootstrapper news roundup episode. They cover a wide range of topics from ProfitWell’s big 200 million exit, spreadsheet mentality, watching an acquirer ruin your company, and much more. Topics we cover: [3:06] What’s your take on ProfitWell’s acquisition? [5:52] Watching an acquirer ruin your company [14:03] The spreadsheet mentality [23:09] If you can’t buy it twice, don’t buy it [36:00] Balancing realism with optimism as a ...
Aug 23, 2022•40 min•Transcript available on Metacast In episode 616 , Rob Walling chats with Liam Martin, the co-founder of Time Doctor and author of the new book, “Running Remote: Master the Lessons from the World’s Most Successful Remote Work Pioneers.” We dig into the fundamentals of asynchronous communication, how to do remote work better, and some surprises they saw during the pandemic. Episode Sponsor Hiring developers has been tough for years, but it is even tougher these days. Lemon.io is on a mission to make the process of hiring an exper...
Aug 16, 2022•34 min•Transcript available on Metacast In episode 616 , Rob Walling chats with Liam Martin, the co-founder of Time Doctor and author of the new book, “Running Remote: Master the Lessons from the World’s Most Successful Remote Work Pioneers.” We dig into the fundamentals of asynchronous communication, how to do remote work better, and some surprises they saw during the pandemic. Episode Sponsor Hiring developers has been tough for years, but it is even tougher these days. Lemon.io is on a mission to make the process of hiring an exper...
Aug 16, 2022•34 min•Transcript available on Metacast In episode 615, join Rob Walling for a solo adventure where he covers what makes a business bootstrappable (and things to avoid), cargo culting, and how large of a business you can build at different customer lifetime value levels. Episode Sponsor: Hiring developers has been tough for years, but it is even tougher these days. Lemon.io is on a mission to make the process of hiring an experienced developer or even an entire team easier. They only have experienced developers on their marketplace, a...
Aug 09, 2022•27 min•Transcript available on Metacast In episode 615, join Rob Walling for a solo adventure where he covers what makes a business bootstrappable (and things to avoid), cargo culting, and how large of a business you can build at different customer lifetime value levels. Episode Sponsor: Hiring developers has been tough for years, but it is even tougher these days. Lemon.io is on a mission to make the process of hiring an experienced developer or even an entire team easier. They only have experienced developers on their marketplace, a...
Aug 09, 2022•27 min•Transcript available on Metacast In episode 614, Rob Walling chats with fan favorite Derrick Reimer. They start out by talking about Derrick’s decision to take a sabbatical from The Art of Product podcast after co-hosting it with Ben Orenstein for more than 5 years. Then, they answer a handful of listener questions, including when to quit your day job to focus on your startup full-time, coping with anxiety as a second-time founder, and choosing a domain name. Episode Sponsor: Hiring developers has been tough for years, but...
Aug 02, 2022•43 min•Transcript available on Metacast In episode 614, Rob Walling chats with fan favorite Derrick Reimer. They start out by talking about Derrick’s decision to take a sabbatical from The Art of Product podcast after co-hosting it with Ben Orenstein for more than 5 years. Then, they answer a handful of listener questions, including when to quit your day job to focus on your startup full-time, coping with anxiety as a second-time founder, and choosing a domain name. Episode Sponsor: Hiring developers has been tough for years, but it i...
Aug 02, 2022•43 min•Transcript available on Metacast In episode 613, Rob Walling chats with Dr. Sherry Walling about the release of her new book, Touching Two Worlds: A guide for finding hope in the landscape of loss. They cover a lot in this episode, including the hustle of launching a book, the behind the scenes of how Sherry has hacked her own psychology to help promote the book, and grief in entrepreneurship. Episode Sponsor: Hiring developers has been tough for years, but it is even tougher these days. Lemon.io is on a mission to make the pro...
Jul 26, 2022•30 min•Transcript available on Metacast In episode 613, Rob Walling chats with Dr. Sherry Walling about the release of her new book, Touching Two Worlds: A guide for finding hope in the landscape of loss. They cover a lot in this episode, including the hustle of launching a book, the behind the scenes of how Sherry has hacked her own psychology to help promote the book, and grief in entrepreneurship. Episode Sponsor: Hiring developers has been tough for years, but it is even tougher these days. Lemon.io is on a mission to make the pro...
Jul 26, 2022•30 min•Transcript available on Metacast In episode 612, Rob Walling chats with longtime friend and repeat podcast guest Dave Rodenbaugh. Dave was even at the very first MicroConf back in 2011. In this episode, we have a candid conversation on our experiences balancing side projects with a day job, struggling with the decision in our own different ways of when to quit, and the surprising habits you have to unlearn once you are finally independent of the day job and consulting work. Topics we cover: [1:27] Dave’s thought process b...
Jul 19, 2022•38 min•Transcript available on Metacast In episode 612, Rob Walling chats with longtime friend and repeat podcast guest Dave Rodenbaugh. Dave was even at the very first MicroConf back in 2011. In this episode, we have a candid conversation on our experiences balancing side projects with a day job, struggling with the decision in our own different ways of when to quit, and the surprising habits you have to unlearn once you are finally independent of the day job and consulting work. Topics we cover: [1:27] Dave’s thought process behind ...
Jul 19, 2022•38 min•Transcript available on Metacast In episode 611, join Rob Walling as he chats with Patrick Campbell, the cofounder of ProfitWell, on how he and his co-founders bootstrapped ProfitWell to a $200 million exit. Profitwell was acquired by Paddle earlier this year. We dive into a bunch of topics you have not heard elsewhere, including details about the actual transaction, what was the stock vs. cash split, the revenue breakdown of consulting versus SaaS when they sold as well as talking through his thought process as they were decid...
Jul 12, 2022•48 min•Transcript available on Metacast In episode 611, join Rob Walling as he chats with Patrick Campbell, the cofounder of ProfitWell, on how he and his co-founders bootstrapped ProfitWell to a $200 million exit. Profitwell was acquired by Paddle earlier this year. We dive into a bunch of topics you have not heard elsewhere, including details about the actual transaction, what was the stock vs. cash split, the revenue breakdown of consulting versus SaaS when they sold as well as talking through his thought process as they were decid...
Jul 12, 2022•48 min•Transcript available on Metacast In episode 610, join Rob Walling for a solo adventure where he talks about the benefits of working a day job before launching your company, some bad habits he picked up in the early days, why the college dropout narrative is annoying, and what he would do if he was starting over today. Topics we cover: [1:08] The benefits of working a day job [6:20] Some bad habits Rob learned as a solopreneur in the early days [9:45] Why the college dropout narrative is bs [12:51] What would R...
Jul 05, 2022•29 min•Transcript available on Metacast In episode 610, join Rob Walling for a solo adventure where he talks about the benefits of working a day job before launching your company, some bad habits he picked up in the early days, why the college dropout narrative is annoying, and what he would do if he was starting over today. Topics we cover: [1:08] The benefits of working a day job [6:20] Some bad habits Rob learned as a solopreneur in the early days [9:45] Why the college dropout narrative is bs [12:51] What would Rob do if he was st...
Jul 05, 2022•29 min•Transcript available on Metacast In episode 609, join Rob Walling for a solo adventure as he answers a handful of listener questions ranging from when it makes sense to have multiple LLCs and hiring task-level vs. project-level thinkers to planning for large projects. He also shares his thought process behind ways you can build a complex mobile app prototype in a capital efficient manner. Topics we cover: [1:56] Is it worth it to create multiple LLCs? [6:10] Do you have any tips for how to find the time to work on f...
Jun 28, 2022•26 min•Transcript available on Metacast In episode 609, join Rob Walling for a solo adventure as he answers a handful of listener questions ranging from when it makes sense to have multiple LLCs and hiring task-level vs. project-level thinkers to planning for large projects. He also shares his thought process behind ways you can build a complex mobile app prototype in a capital efficient manner. Topics we cover: [1:56] Is it worth it to create multiple LLCs? [6:10] Do you have any tips for how to find the time to work on future improv...
Jun 28, 2022•26 min•Transcript available on Metacast In episode 608, Rob Walling chats with Adrian Rosebrock, who bootstrapped and successfully exited his seven-figure info product company, PyImageSearch, in 2021. PyImageSearch provided digital courses around visual image detection and image classification in Python. Adrian wasn’t always an entrepreneur. He graduated with a PhD in computer science, got a day job, realized early on that he hated it, and just stair-stepped his way up to running a successful business. In this episode, we cover a lot ...
Jun 21, 2022•51 min•Transcript available on Metacast In episode 608, Rob Walling chats with Adrian Rosebrock, who bootstrapped and successfully exited his seven-figure info product company, PyImageSearch, in 2021. PyImageSearch provided digital courses around visual image detection and image classification in Python. Adrian wasn’t always an entrepreneur. He graduated with a PhD in computer science, got a day job, realized early on that he hated it, and just stair-stepped his way up to running a successful business. In this episode, we cover a lot ...
Jun 21, 2022•51 min•Transcript available on Metacast In episode 607, Rob Walling chats with Asia Orangio, and they answer listener questions about customer onboarding videos, overcoming revenue plateaus, stealth launches, and founder-driven sales. Topics we cover: [1:12] Where’s the best place to put customer onboarding videos? [5:37] How to scale a content business [15:36] What to do if revenue has plateaued? [21:41] When to do a stealth launch [26:30] Is it possible for a SaaS product to sell to the enterprise...
Jun 14, 2022•35 min•Transcript available on Metacast In episode 607, Rob Walling chats with Asia Orangio, and they answer listener questions about customer onboarding videos, overcoming revenue plateaus, stealth launches, and founder-driven sales. Topics we cover: [1:12] Where’s the best place to put customer onboarding videos? [5:37] How to scale a content business [15:36] What to do if revenue has plateaued? [21:41] When to do a stealth launch [26:30] Is it possible for a SaaS product to sell to the enterprise without a dedicated sales team? Lin...
Jun 14, 2022•35 min•Transcript available on Metacast In episode 606, Rob Walling chats with Craig Hewitt, the founder of Castos. They talk about company building, staying up to speed when you are no longer doing the day-to-day tasks as well as their thoughts on a recent string of acquisitions happening in the podcast ecosystem. Topics we cover: [1:24] 2 MicroConf Local events happening in Chicago and Denver [3:50] The pros and cons of Spotify acquiring a couple of podcast analytics platforms [7:51] The specific challenges with p...
Jun 07, 2022•35 min•Transcript available on Metacast In episode 606, Rob Walling chats with Craig Hewitt, the founder of Castos. They talk about company building, staying up to speed when you are no longer doing the day-to-day tasks as well as their thoughts on a recent string of acquisitions happening in the podcast ecosystem. Topics we cover: [1:24] 2 MicroConf Local events happening in Chicago and Denver [3:50] The pros and cons of Spotify acquiring a couple of podcast analytics platforms [7:51] The specific challenges with podcast analytics [1...
Jun 07, 2022•35 min•Transcript available on Metacast In episode 605, Rob Walling is joined by Ruben Gamez, and they dig into a handful of listener questions. Topics range from building a SaaS with little development experience and using no-code tools to build your MVP to stair-stepping bootstrapping a two-sided marketplace. Topics we cover: [0:55] Selling to the enterprise [4:31] What level of development expertise would you say the founders of a B2B SaaS should have in order to create a successful product? [13:26] Should you lau...
May 31, 2022•42 min•Transcript available on Metacast In episode 605, Rob Walling is joined by Ruben Gamez, and they dig into a handful of listener questions. Topics range from building a SaaS with little development experience and using no-code tools to build your MVP to stair-stepping bootstrapping a two-sided marketplace. Topics we cover: [0:55] Selling to the enterprise [4:31] What level of development expertise would you say the founders of a B2B SaaS should have in order to create a successful product? [13:26] Should you launch a productized ...
May 31, 2022•42 min•Transcript available on Metacast 
