In episode 604, Rob Walling talks with Derrick Reimer and gets the latest update on SavvyCal, how he makes product decisions, and they also share the best things they’ve bought for $100 and $1000 that have added much more value to their lives than the price point. Topics we cover: [4:50] Apple’s influence on startup founders [8:52] SavvyCal’s new Squadcast integration [12:51] Some upcoming features in the works for SavvyCal [14:05] Experimenting with a freemium feature—meeting ...
May 24, 2022•42 min•Transcript available on Metacast In episode 604, Rob Walling talks with Derrick Reimer and gets the latest update on SavvyCal, how he makes product decisions, and they also share the best things they’ve bought for $100 and $1000 that have added much more value to their lives than the price point. Topics we cover: [4:50] Apple’s influence on startup founders [8:52] SavvyCal’s new Squadcast integration [12:51] Some upcoming features in the works for SavvyCal [14:05] Experimenting with a freemium feature—meeting polls [17:07] Derr...
May 24, 2022•42 min•Transcript available on Metacast In episode 603, Rob Walling chats with David Darmanin, one of the founders of Hotjar. Hotjar was bootstrapped to $40 million ARR with a fully distributed team of 170 employees. David and his cofounders sold the company for a 9-figure exit in 2021. From their incredible launch story and their unique DTC approach to sales and marketing in a B2B SaaS business to David’s mental models and the thought process behind selling the business, there is no shortage of key insights in this episode. Topics we...
May 17, 2022•44 min•Transcript available on Metacast In episode 603, Rob Walling chats with David Darmanin, one of the founders of Hotjar. Hotjar was bootstrapped to $40 million ARR with a fully distributed team of 170 employees. David and his cofounders sold the company for a 9-figure exit in 2021. From their incredible launch story and their unique DTC approach to sales and marketing in a B2B SaaS business to David’s mental models and the thought process behind selling the business, there is no shortage of key insights in this episode. Topics we...
May 17, 2022•44 min•Transcript available on Metacast In episode 602, Rob Walling explains SaaS metrics to his kid. This is a great episode to listen to if you are unfamiliar or not well-versed in SaaS because we dig into from first principles, starting with dollars, revenue, and the purpose of businesses, all the way to SaaS metrics like MRR, ACV, and LTV. And, even if you are well-versed in SaaS metrics, you’ll likely learn a few things from this conversation. Episode Sponsor: Microsoft for Startups Founder Hub Microsoft for Startups is on a miss...
May 10, 2022•29 min•Transcript available on Metacast In episode 602, Rob Walling explains SaaS metrics to his kid. This is a great episode to listen to if you are unfamiliar or not well-versed in SaaS because we dig into from first principles, starting with dollars, revenue, and the purpose of businesses, all the way to SaaS metrics like MRR, ACV, and LTV. And, even if you are well-versed in SaaS metrics, you’ll likely learn a few things from this conversation. Episode Sponsor: Microsoft for Startups Founder Hub Microsoft for Startups is on a miss...
May 10, 2022•29 min•Transcript available on Metacast In episode 601, Rob Walling chats with Nick Fogle of ChurnKey. Nick previously cofounded Wavve which was acquired in early 2021. In this conversation, they chat about how the idea for Churnkey came from his other business, decision to sell Wavve, and some of the key differences between bootstrapping a B2C vs a B2B SaaS. Topics we cover: [2:11] Tips for reducing churn [3:26] Asking for feedback at the point of cancellation via feedback surveys [8:09] When he knew it was the righ...
May 03, 2022•39 min•Transcript available on Metacast In episode 601, Rob Walling chats with Nick Fogle of ChurnKey. Nick previously cofounded Wavve which was acquired in early 2021. In this conversation, they chat about how the idea for Churnkey came from his other business, decision to sell Wavve, and some of the key differences between bootstrapping a B2C vs a B2B SaaS. Topics we cover: [2:11] Tips for reducing churn [3:26] Asking for feedback at the point of cancellation via feedback surveys [8:09] When he knew it was the right time to double d...
May 03, 2022•39 min•Transcript available on Metacast In episode 600, join Rob Walling for a solo adventure as he dives into topics ranging from when to hire your first manager to a mental framework for deciding which things to work on vs. what to delegate to your team. He also shares his thought process behind when things take multiple iterations and how to know whether or not you are on the right track. Episode Sponsor: Microsoft for Startups Founder Hub Microsoft for Startups is on a mission to help all founders innovate and grow...
Apr 26, 2022•30 min•Transcript available on Metacast In episode 600, join Rob Walling for a solo adventure as he dives into topics ranging from when to hire your first manager to a mental framework for deciding which things to work on vs. what to delegate to your team. He also shares his thought process behind when things take multiple iterations and how to know whether or not you are on the right track. Episode Sponsor: Microsoft for Startups Founder Hub Microsoft for Startups is on a mission to help all founders innovate and grow no matter their...
Apr 26, 2022•30 min•Transcript available on Metacast In episode 599, Rob Walling chats with Dominic “Dom” and Tracy Phillips of CodeSubmit. CodeSubmit provides a library of real-world, take-home tasks in more than 60 coding languages. Some of their customers are Audi, Netflix, Carbon Health, 3M, and Apple. Dom and Tracy were also a part of the spring 2020 batch of TinySeed. During that year, they managed to 25x their MRR. In this episode, we’re digging into how they did that, what led to their bootstrapped hockey stick growth moment, what it is li...
Apr 19, 2022•34 min•Transcript available on Metacast In episode 599, Rob Walling chats with Dominic “Dom” and Tracy Phillips of CodeSubmit. CodeSubmit provides a library of real-world, take-home tasks in more than 60 coding languages. Some of their customers are Audi, Netflix, Carbon Health, 3M, and Apple. Dom and Tracy were also a part of the spring 2020 batch of TinySeed. During that year, they managed to 25x their MRR. In this episode, we’re digging into how they did that, what led to their bootstrapped hockey stick growth moment, what it is li...
Apr 19, 2022•34 min•Transcript available on Metacast In episode 598, join Rob Walling as he answers listener emails. Topics range from diversity in the startup ecosystem and when’s the right time to write your company’s mission, philosophy, and values to how to find good business ideas and the different approaches for developing features for a new app. Episode Sponsor: Microsoft for Startups Founder Hub Microsoft for Startups is on a mission to help all founders innovate and grow no matter their background, location, or progress. Microsoft for Sta...
Apr 12, 2022•27 min•Transcript available on Metacast In episode 598, join Rob Walling as he answers listener emails. Topics range from diversity in the startup ecosystem and when’s the right time to write your company’s mission, philosophy, and values to how to find good business ideas and the different approaches for developing features for a new app. Episode Sponsor: Microsoft for Startups Founder Hub Microsoft for Startups is on a mission to help all founders innovate and grow no matter their background, location, or progress. Microsoft for Sta...
Apr 12, 2022•27 min•Transcript available on Metacast In episode 597, Rob Walling chats with Ashley Baxter, the founder of With Jack. With Jack gives peace of mind and protection for UK freelancers through insurance, professional indemnity, public liability, contracts, legal expenses, etc. We dig into the lessons Ashley learned from a failed insurance business she inherited from her father, how she used her freelance photography to fund With Jack in the early days, along with sharing many of the successes and failures she has had on her entrepreneu...
Apr 05, 2022•37 min•Transcript available on Metacast In episode 597, Rob Walling chats with Ashley Baxter, the founder of With Jack. With Jack gives peace of mind and protection for UK freelancers through insurance, professional indemnity, public liability, contracts, legal expenses, etc. We dig into the lessons Ashley learned from a failed insurance business she inherited from her father, how she used her freelance photography to fund With Jack in the early days, along with sharing many of the successes and failures she has had on her entrepreneu...
Apr 05, 2022•37 min•Transcript available on Metacast In episode 596, Rob Walling is joined by Einar Vollset and Tracy Osborn for a bootstrapper news roundup episode. They cover a wide range of topics from Google’s decision to bring employees back into the office (and the potential implications for bootstrapped companies), founder salary data trends, email management strategies, and much more. Episode Sponsor: Microsoft for Startups Founder Hub Microsoft for Startups is on a mission to help all founders innovate and grow no matter t...
Mar 29, 2022•40 min•Transcript available on Metacast In episode 596, Rob Walling is joined by Einar Vollset and Tracy Osborn for a bootstrapper news roundup episode. They cover a wide range of topics from Google’s decision to bring employees back into the office (and the potential implications for bootstrapped companies), founder salary data trends, email management strategies, and much more. Episode Sponsor: Microsoft for Startups Founder Hub Microsoft for Startups is on a mission to help all founders innovate and grow no matter their background,...
Mar 29, 2022•40 min•Transcript available on Metacast In episode 595, Rob Walling catches up with Brian and Scottie Elliott, the husband and wife co-founders of Gather, an interior design project management SaaS. This husband and wife duo shared their victories, challenges, and failures, including a cash crunch, moving upmarket, and managing to double revenue over their nine episodes of TinySeed Tales Season 2. It’s been over a year since they were last on the podcast and wanted to see how the company is doing. It turns out Gather is on track to 10...
Mar 22, 2022•26 min•Transcript available on Metacast In episode 595, Rob Walling catches up with Brian and Scottie Elliott, the husband and wife co-founders of Gather, an interior design project management SaaS. This husband and wife duo shared their victories, challenges, and failures, including a cash crunch, moving upmarket, and managing to double revenue over their nine episodes of TinySeed Tales Season 2. It’s been over a year since they were last on the podcast and wanted to see how the company is doing. It turns out Gather is on track to 10...
Mar 22, 2022•26 min•Transcript available on Metacast In Episode 594, Rob Walling chats with Dan Andrews and Ian Schoen, the founders of Dynamite Jobs and the TropicalMBA podcast. We talk about how they started over. They started a new business, Dynamite Jobs, a couple of years after selling their physical products company back in 2015. Episode Sponsor: Microsoft for Startups Founder Hub Microsoft for Startups is on a mission to help all founders innovate and grow no matter their background, location, or progress. Microsoft&nbs...
Mar 15, 2022•46 min•Transcript available on Metacast In Episode 594, Rob Walling chats with Dan Andrews and Ian Schoen, the founders of Dynamite Jobs and the TropicalMBA podcast. We talk about how they started over. They started a new business, Dynamite Jobs, a couple of years after selling their physical products company back in 2015. Episode Sponsor: Microsoft for Startups Founder Hub Microsoft for Startups is on a mission to help all founders innovate and grow no matter their background, location, or progress. Microsoft for Startups Founders Hu...
Mar 15, 2022•46 min•Transcript available on Metacast In Episode 593, join Rob Walling for a Solo Adventure as he chats about accidentally deleting all of his old tweets, retaining talent, the ideal market for a SaaS business, and more. The topics we cover [3:10] Deleting old tweets [8:43] Retaining talent [12:39] Ideal market for a SaaS business If you have questions about starting or scaling a software business that you'd like for us to cover, please submit your question for an upcoming episode. We'd love to hear from you! Subscribe &...
Mar 08, 2022•25 min•Transcript available on Metacast In Episode 593, join Rob Walling for a Solo Adventure as he chats about accidentally deleting all of his old tweets, retaining talent, the ideal market for a SaaS business, and more. The topics we cover [3:10] Deleting old tweets [8:43] Retaining talent [12:39] Ideal market for a SaaS business If you have questions about starting or scaling a software business that you'd like for us to cover, please submit your question for an upcoming episode. We'd love to hear from you! Subscribe & Review:...
Mar 08, 2022•25 min•Transcript available on Metacast In Episode 592, Rob Walling is joined again by Cody Duval for a technical conversation about the dos and don'ts for amazing customer support. The topics we cover [2:00] Customer success vs customer support [5:10] Response time [8:59] Post-support surveys [10:58] When to hire first customer support person [13:02] Chat widgets [17:09] Doing customer support early on as a founder [18:01] Training customer support to ask a question [19:00] Dealing with abusive customers [21:10] Customer support tool...
Mar 01, 2022•30 min•Transcript available on Metacast In Episode 592, Rob Walling is joined again by Cody Duval for a technical conversation about the dos and don'ts for amazing customer support. The topics we cover [2:00] Customer success vs customer support [5:10] Response time [8:59] Post-support surveys [10:58] When to hire first customer support person [13:02] Chat widgets [17:09] Doing customer support early on as a founder [18:01] Training customer support to ask a question [19:00] Dealing with abusive customers [21:10] Customer support tool...
Mar 01, 2022•30 min•Transcript available on Metacast In Episode 591, Rob Walling chats with Cody Duvall about his story of acquiring and growing Keeping in a really crowded space of help desk and customer support tools. The topics we cover [4:34] Launching into a crowded market [8:00] Keeping's sales process [10:01] Background on acquiring Keeping [14:53] Outsourcing a team to rewrite the codebase [20:03] Migrating customers [24;01] Challenges with building in a established category [26:09] Hitting product-market fit [28:30] Applying for TinySeed ...
Feb 22, 2022•35 min•Transcript available on Metacast In Episode 591, Rob Walling chats with Cody Duvall about his story of acquiring and growing Keeping in a really crowded space of help desk and customer support tools. The topics we cover [4:34] Launching into a crowded market [8:00] Keeping's sales process [10:01] Background on acquiring Keeping [14:53] Outsourcing a team to rewrite the codebase [20:03] Migrating customers [24;01] Challenges with building in a established category [26:09] Hitting product-market fit [28:30] Applying for TinySeed ...
Feb 22, 2022•35 min•Transcript available on Metacast In Episode 590, Rob Walling chats with Craig Hewitt about building versus buying internal tools, how to compete in a competitive space, accounting software, a founder who has a zombie company where investors want their money back, and more. The topics we cover [5:03] Finding a co-founder as a non-technical founder [11:20] Balancing priorities between day job and a SaaS idea [17:35] Zombie company where investors want their money back [26:00] Accounting software for startups [28:10] Building in a...
Feb 15, 2022•37 min•Transcript available on Metacast In Episode 590, Rob Walling chats with Craig Hewitt about building versus buying internal tools, how to compete in a competitive space, accounting software, a founder who has a zombie company where investors want their money back, and more. The topics we cover [5:03] Finding a co-founder as a non-technical founder [11:20] Balancing priorities between day job and a SaaS idea [17:35] Zombie company where investors want their money back [26:00] Accounting software for startups [28:10] Building in a...
Feb 15, 2022•37 min•Transcript available on Metacast 
