In this episode, Rob speaks with Adii Pienaar, a multi-time founder with multiple exits under his belt. They discuss life probability and the importance of measuring your entrepreneurial success by the things that matter the most to you and your life. The topics we cover [4:36] What motivated Adii to write the book [10:17] Life probability defined [12:45] Work-life balance is not the solution [29:21] Choosing to go back into the SaaS trenches If you enjoyed this episode, let us know by clicking ...
Jan 26, 2021•37 min•Transcript available on Metacast In this episode, Rob speaks with Adii Pienaar, a multi-time founder with multiple exits under his belt. They discuss life probability and the importance of measuring your entrepreneurial success by the things that matter the most to you and your life. The topics we cover [4:36] What motivated Adii to write the book [10:17] Life probability defined [12:45] Work-life balance is not the solution [29:21] Choosing to go back into the SaaS trenches If you enjoyed this episode, let us know by clicking ...
Jan 26, 2021•37 min•Transcript available on Metacast In this episode, Rob sits down with John Warrillow, author of multiple bestselling books and someone who has years of experience in building and selling companies. They discuss when to sell, how to create leverage, the importance of hiring an expert, and more. The topics we cover [7:30] The right time to sell a company [15:06] Gaining leverage when negotiating [20:59] Sell-side processes for founders [29:14] The 5/20 rule [31:41] Things to look out for from potential acquirers Links from the sho...
Jan 19, 2021•41 min•Transcript available on Metacast In this episode, Rob sits down with John Warrillow, author of multiple bestselling books and someone who has years of experience in building and selling companies. They discuss when to sell, how to create leverage, the importance of hiring an expert, and more. The topics we cover [7:30] The right time to sell a company [15:06] Gaining leverage when negotiating [20:59] Sell-side processes for founders [29:14] The 5/20 rule [31:41] Things to look out for from potential acquirers Links from the sho...
Jan 19, 2021•41 min•Transcript available on Metacast In Episode 531, Rob talks with Colin Gray, the founder of The Podcast Host and Alitu. Join us for this great conversation as we talk about Colin's early days of building a hobby project in podcast hosting, hiring a freelancer to start producing shows. and building a SaaS app on top of an audience. The topics we cover [7:05] Launching The Podcast Host [16:10] Growing and launching eight businesses at once [21:08] Making the switch to SaaS [30:49] Temptations of shutting down vs. accelerating grow...
Jan 12, 2021•40 min•Transcript available on Metacast In Episode 531, Rob talks with Colin Gray, the founder of The Podcast Host and Alitu. Join us for this great conversation as we talk about Colin's early days of building a hobby project in podcast hosting, hiring a freelancer to start producing shows. and building a SaaS app on top of an audience. The topics we cover [7:05] Launching The Podcast Host [16:10] Growing and launching eight businesses at once [21:08] Making the switch to SaaS [30:49] Temptations of shutting down vs. accelerating grow...
Jan 12, 2021•40 min•Transcript available on Metacast In this week's episode, Rob sits down with Derrick Reimer to answer listener questions. They discuss whether they have any regrets about selling Drip, protecting against web scraping, making the leap from side project to full-time, and making decisions as a development team. The topics we cover [2:10] How development teams think about decisions together [13:42] Do you ever regret selling Drip to Leadpages? [21:00] Preventing against web scraping [27:16] Jumping ship from a full-time job [37:20] ...
Jan 05, 2021•48 min•Transcript available on Metacast In this week's episode, Rob sits down with Derrick Reimer to answer listener questions. They discuss whether they have any regrets about selling Drip, protecting against web scraping, making the leap from side project to full-time, and making decisions as a development team. The topics we cover [2:10] How development teams think about decisions together [13:42] Do you ever regret selling Drip to Leadpages? [21:00] Preventing against web scraping [27:16] Jumping ship from a full-time job [37:20] ...
Jan 05, 2021•48 min•Transcript available on Metacast In this episode, Rob chats with John Howard, a MicroConf Connect member and founder of Slingshot. They unpack the business model of measurable swag giveaways and then dive deep into John's pricing strategy and explore alternatives as well as opportunities to move into a subscription-based model. The topics we cover [9:26] Starting a physical product business [24:53] Previous pricing models [30:48] Customer acquisition [39:41] Removing setup fee or raising prices Links from the show Slingshot Bla...
Dec 29, 2020•49 min•Transcript available on Metacast In this episode, Rob chats with John Howard, a MicroConf Connect member and founder of Slingshot. They unpack the business model of measurable swag giveaways and then dive deep into John's pricing strategy and explore alternatives as well as opportunities to move into a subscription-based model. The topics we cover [9:26] Starting a physical product business [24:53] Previous pricing models [30:48] Customer acquisition [39:41] Removing setup fee or raising prices Links from the show Slingshot Bla...
Dec 29, 2020•49 min•Transcript available on Metacast In today's episode, Rob and Mike Taber review and rank their past yearly predictions and then make big, bold projections for 2021 with bets ranging from extraterrestrial life, VR becoming mainstream, the end of commercial real estate, and more. The topics we cover [2:45] Reviewing our predictions for 2019 [7:42] Predictions for 2021 If you enjoyed this episode, let us know by clicking the link and sharing what you learned. Click here to share your number one takeaway from the episode. If you hav...
Dec 22, 2020•31 min•Transcript available on Metacast In today's episode, Rob and Mike Taber review and rank their past yearly predictions and then make big, bold projections for 2021 with bets ranging from extraterrestrial life, VR becoming mainstream, the end of commercial real estate, and more. The topics we cover [2:45] Reviewing our predictions for 2019 [7:42] Predictions for 2021 If you enjoyed this episode, let us know by clicking the link and sharing what you learned. Click here to share your number one takeaway from the episode. If you hav...
Dec 22, 2020•31 min•Transcript available on Metacast In today's episode, Rob is joined by Courtland Allen as they answer listener questions. They talk about equity splits, the best cities for bootstrappers, splitting brands, and where to look for business ideas. The topics we cover [2:03] Splitting brands between agency and SaaS [10:55] What percent equity split when co-founding an app [18:52] Where to look for ideas [31:02] Best city for bootstrappers Links from the show From $0 to $5M Without Writing Any Code with Tara Reed of Apps Without Code ...
Dec 15, 2020•42 min•Transcript available on Metacast In today's episode, Rob is joined by Courtland Allen as they answer listener questions. They talk about equity splits, the best cities for bootstrappers, splitting brands, and where to look for business ideas. The topics we cover [2:03] Splitting brands between agency and SaaS [10:55] What percent equity split when co-founding an app [18:52] Where to look for ideas [31:02] Best city for bootstrappers Links from the show From $0 to $5M Without Writing Any Code with Tara Reed of Apps Without Code ...
Dec 15, 2020•42 min•Transcript available on Metacast In episode 526 of Startups For the Rest of Us, Rob chats with a long-time friend, Justin Vincent about his startup successes and failures and the importance of taking small steps when starting as a founder. They also talk about Justin's latest project, Nugget, a startup bootcamp and academy. The topics we cover [4:04] Building Plugg.io [10:30] Enthusiasm half-life [16:03] Nugget Startup Academy [25:54] Founder context Links from the show Techzing Nugget Plugg.io Is it Keto? Michael Lynch J...
Dec 08, 2020•37 min•Transcript available on Metacast In episode 526 of Startups For the Rest of Us, Rob chats with a long-time friend, Justin Vincent about his startup successes and failures and the importance of taking small steps when starting as a founder. They also talk about Justin's latest project, Nugget, a startup bootcamp and academy. The topics we cover [4:04] Building Plugg.io [10:30] Enthusiasm half-life [16:03] Nugget Startup Academy [25:54] Founder context Links from the show Techzing Nugget Plugg.io Is it Keto? Michael Lynch Justin ...
Dec 08, 2020•37 min•Transcript available on Metacast This episode is a walk down memory lane as Rob shares the story of acquiring his first product 15 years ago. We hear how Rob navigated the purchase of the product, a potential partnership with a trusted friend, and pushing through when his back was against the wall. Hopefully, this episode will inspire you to take action and keep shipping. The topics we cover [5:03] Three levels to making money online [6:36] Discovering the original version of DotNetInvoice [11:34] The business proposition [15:1...
Dec 01, 2020•27 min•Transcript available on Metacast This episode is a walk down memory lane as Rob shares the story of acquiring his first product 15 years ago. We hear how Rob navigated the purchase of the product, a potential partnership with a trusted friend, and pushing through when his back was against the wall. Hopefully, this episode will inspire you to take action and keep shipping. The topics we cover [5:03] Three levels to making money online [6:36] Discovering the original version of DotNetInvoice [11:34] The business proposition [15:1...
Dec 01, 2020•27 min•Transcript available on Metacast In this episode, Rob chats with Michele and Mathias Hansen, the married co-founders of Geocodio. We talk about bootstrapping into a commoditized space and how they've grown their SaaS app from a side project to full-time over the past 6.5 years. The topics we cover [01:38] What is Geocodio? [10:29] Innovating in a commoditized market [16:07] How they defined their product roadmap [18:06] Launching a HIPAA compliant enterprise pricing tier Links from the show Show HN: Ridiculously cheap bulk geoc...
Nov 24, 2020•32 min•Transcript available on Metacast In this episode, Rob chats with Michele and Mathias Hansen, the married co-founders of Geocodio. We talk about bootstrapping into a commoditized space and how they've grown their SaaS app from a side project to full-time over the past 6.5 years. The topics we cover [01:38] What is Geocodio? [10:29] Innovating in a commoditized market [16:07] How they defined their product roadmap [18:06] Launching a HIPAA compliant enterprise pricing tier Links from the show Show HN: Ridiculously cheap bulk geoc...
Nov 24, 2020•32 min•Transcript available on Metacast In episode 523, Rob hosts a rapid-fire lightning round of listener questions ranging from whether to focus on one or multiple businesses, finding the right amount of customer research, breaking through slow growth, and teaching entrepreneurship to kids. The topics we cover [4:38] If you were starting a business today and you were earlier on in your career, would you try multiple business ideas at once or go all-in on one? [8:11] If building your first tiny product, like a WordPress plugin, what ...
Nov 17, 2020•30 min•Transcript available on Metacast In episode 523, Rob hosts a rapid-fire lightning round of listener questions ranging from whether to focus on one or multiple businesses, finding the right amount of customer research, breaking through slow growth, and teaching entrepreneurship to kids. The topics we cover [4:38] If you were starting a business today and you were earlier on in your career, would you try multiple business ideas at once or go all-in on one? [8:11] If building your first tiny product, like a WordPress plugin, what ...
Nov 17, 2020•30 min•Transcript available on Metacast Rob welcomes back to the show a frequent guest, Craig Hewitt for a " Where Are They Now? " syle episode. Craig is the founder of Castos and has appeared many times on Startups For the Rest of Us. In this episode, they reconnect and talk about the latest with Castos, from hiring a growth marketer, merging brands, private podcasting, and so much more. The topics we cover [3:54] Reflections on hiring a growth marketer 1 year later [6:92] How did the free trial without asking for a credit card exper...
Nov 10, 2020•45 min•Transcript available on Metacast Rob welcomes back to the show a frequent guest, Craig Hewitt for a " Where Are They Now? " syle episode. Craig is the founder of Castos and has appeared many times on Startups For the Rest of Us. In this episode, they reconnect and talk about the latest with Castos, from hiring a growth marketer, merging brands, private podcasting, and so much more. The topics we cover [3:54] Reflections on hiring a growth marketer 1 year later [6:92] How did the free trial without asking for a credit card exper...
Nov 10, 2020•45 min•Transcript available on Metacast Brian & Scottie Elliott are the husband & wife co-founders of Gather , an interior design project management app. Join Rob as he chats with Brian & Scottie for the final episode of Season 2 of TinySeed Tales. In the last year, Gather managed to double their revenue and overcome most of the challenges they faced along the way. It's been about a month since we last spoke and during that time, their recent cash crunch has started to resolve itself. In this episode, we reflect on the pas...
Nov 05, 2020•20 min•Transcript available on Metacast Brian & Scottie Elliott are the husband & wife co-founders of Gather , an interior design project management app. Join Rob as he chats with Brian & Scottie for the final episode of Season 2 of TinySeed Tales. In the last year, Gather managed to double their revenue and overcome most of the challenges they faced along the way. It's been about a month since we last spoke and during that time, their recent cash crunch has started to resolve itself. In this episode, we reflect on the pas...
Nov 05, 2020•20 min•Transcript available on Metacast Episode 521 is a roundtable episode where Rob brings on a couple of guests to talk through topics today that relate to bootstrapped and mostly bootstrapped startup founders. Today, we have Tracy Osborn and Einar Vollset joining us, as we talk through a potential impending recession, the Google anti-trust suit, Dropbox moving to permanent work from home, as well as a handful of other topics. The topics we cover [04:03] What do the revenue trends look like in 6-7 months from now? [13:36] Google an...
Nov 03, 2020•47 min•Transcript available on Metacast Episode 521 is a roundtable episode where Rob brings on a couple of guests to talk through topics today that relate to bootstrapped and mostly bootstrapped startup founders. Today, we have Tracy Osborn and Einar Vollset joining us, as we talk through a potential impending recession, the Google anti-trust suit, Dropbox moving to permanent work from home, as well as a handful of other topics. The topics we cover [04:03] What do the revenue trends look like in 6-7 months from now? [13:36] Google an...
Nov 03, 2020•47 min•Transcript available on Metacast Brian & Scottie Elliott are the husband & wife co-founders of Gather , an interior design project management app. Last time we spoke, they were bouncing back from the initial shock of the COVID-19 crisis with the potential to sign two large enterprise deals that could help them out with an ongoing cash crunch. In this episode, Rob talks with them about customer-funded development, always following up when doing outbound sales, and restarting a productized service. The topics we cover [01...
Oct 29, 2020•25 min•Transcript available on Metacast Brian & Scottie Elliott are the husband & wife co-founders of Gather , an interior design project management app. Last time we spoke, they were bouncing back from the initial shock of the COVID-19 crisis with the potential to sign two large enterprise deals that could help them out with an ongoing cash crunch. In this episode, Rob talks with them about customer-funded development, always following up when doing outbound sales, and restarting a productized service. The topics we cover [01...
Oct 29, 2020•25 min•Transcript available on Metacast 
