In Episode 562, join Rob Walling for another solo adventure to talk about enterprise sales, mental frameworks for founders, undoable decisions, and how to handle being approached about an acquisition. The topics we cover [2:33] Enterprise sales advice [5:48] Measure twice, cut once for SaaS [10:56] Holy Grail of SaaS: Expansion Revenue [13:12] Holy Grail of SaaS: Virality [14:25] Holy Grail of SaaS: Big space with slow-moving incumbents [15:46] Things to keep in mind when being approached about ...
Aug 10, 2021•19 min•Transcript available on Metacast In Episode 562, join Rob Walling for another solo adventure to talk about enterprise sales, mental frameworks for founders, undoable decisions, and how to handle being approached about an acquisition. The topics we cover [2:33] Enterprise sales advice [5:48] Measure twice, cut once for SaaS [10:56] Holy Grail of SaaS: Expansion Revenue [13:12] Holy Grail of SaaS: Virality [14:25] Holy Grail of SaaS: Big space with slow-moving incumbents [15:46] Things to keep in mind when being approached about ...
Aug 10, 2021•19 min•Transcript available on Metacast In Episode 561, Rob Walling chats with Andy Cabasso, co-founder of Postaga, about launching on Product Hunt, having a done-for-you service in addition to a DIY self-service SaaS app, growing to a team of six people, having a free plan, and doing a ton of customer development in the early days. The topics we cover [01:35] Selling an agency with retainers to start Postaga [03:46] Explaining Postaga simply and succintly [06:32] Size and stage of Postaga [07:24] Using Postaga to market Postaga [10:2...
Aug 03, 2021•37 min•Transcript available on Metacast In Episode 561, Rob Walling chats with Andy Cabasso, co-founder of Postaga, about launching on Product Hunt, having a done-for-you service in addition to a DIY self-service SaaS app, growing to a team of six people, having a free plan, and doing a ton of customer development in the early days. The topics we cover [01:35] Selling an agency with retainers to start Postaga [03:46] Explaining Postaga simply and succintly [06:32] Size and stage of Postaga [07:24] Using Postaga to market Postaga [10:2...
Aug 03, 2021•37 min•Transcript available on Metacast In Episode 560, Rob Walling is joined by Einar Vollset and Tracy Osborn to talk about deciding when it's time to hire someone, how to think about which role to hire next, changing location to force productivity, and more. The topics we cover [2:52] Deciding to hire a community manager [9:28] Location hacks for improved productivity [14:52] Delta airline pilot suing Delta for stealing app [20:35] Product → Business → Company [27:18] Facebook Users say "No" and Advertisers are Panicking [32:32] Te...
Jul 27, 2021•38 min•Transcript available on Metacast In Episode 560, Rob Walling is joined by Einar Vollset and Tracy Osborn to talk about deciding when it's time to hire someone, how to think about which role to hire next, changing location to force productivity, and more. The topics we cover [2:52] Deciding to hire a community manager [9:28] Location hacks for improved productivity [14:52] Delta airline pilot suing Delta for stealing app [20:35] Product → Business → Company [27:18] Facebook Users say "No" and Advertisers are Panicking [32:32] Te...
Jul 27, 2021•38 min•Transcript available on Metacast In Episode 559, Rob Walling chats with Andrew Gazdecki, the founder of MicroAcquire, about bootstrapping a two-sided marketplace in a competitive industry. They talk about Andrew's previous successes, including growing Bizness Apps to $10 million in annual recurring revenue. They also unpack Andrew's current business, MicroAcquire, and talk about how it was started, its current success, and the future plans for the business. The topics we cover [6:03] Why did Andrew decide to sell Bizness [8:12]...
Jul 20, 2021•34 min•Transcript available on Metacast In Episode 559, Rob Walling chats with Andrew Gazdecki, the founder of MicroAcquire, about bootstrapping a two-sided marketplace in a competitive industry. They talk about Andrew's previous successes, including growing Bizness Apps to $10 million in annual recurring revenue. They also unpack Andrew's current business, MicroAcquire, and talk about how it was started, its current success, and the future plans for the business. The topics we cover [6:03] Why did Andrew decide to sell Bizness [8:12]...
Jul 20, 2021•34 min•Transcript available on Metacast In Episode 558, Rob Walling chats with Einar Vollset about bootstrapping versus funding and the many options that exist in between. No longer is it a decision between a bootstrapped or venture path. With their unique perspectives, Rob and Einar talk about all of the funding options that exist. They also share some things to consider when deciding whether or not to take on funding and, if you do, how much you should plan on raising. The topics we cover [04:24] When funding makes sense for bootstr...
Jul 13, 2021•43 min•Transcript available on Metacast In Episode 558, Rob Walling chats with Einar Vollset about bootstrapping versus funding and the many options that exist in between. No longer is it a decision between a bootstrapped or venture path. With their unique perspectives, Rob and Einar talk about all of the funding options that exist. They also share some things to consider when deciding whether or not to take on funding and, if you do, how much you should plan on raising. The topics we cover [04:24] When funding makes sense for bootstr...
Jul 13, 2021•43 min•Transcript available on Metacast In Episode 557, Rob Walling flies solo to talk about investing for founders, with an emphasis on retirement. Rob views investing as a long-term game, not treating the stock market like a slot machine by buying and selling stocks. As founders, we're busy with our work, our family, and our friends. We don't want to spend a ton of time fiddling with investments. In this episode, Rob outlines an 80/20 approach to getting the most out of investing as a founder. The topics we cover [02:13] How Rob mad...
Jul 06, 2021•26 min•Transcript available on Metacast In Episode 557, Rob Walling flies solo to talk about investing for founders, with an emphasis on retirement. Rob views investing as a long-term game, not treating the stock market like a slot machine by buying and selling stocks. As founders, we're busy with our work, our family, and our friends. We don't want to spend a ton of time fiddling with investments. In this episode, Rob outlines an 80/20 approach to getting the most out of investing as a founder. The topics we cover [02:13] How Rob mad...
Jul 06, 2021•26 min•Transcript available on Metacast In Episode 556, Rob Walling chats with Adam McCrea about growing from zero to $300,000 in ARR over the course of three years as a Heroku add-on. Adam is still a single founder with no employees and up until joining the TinySeed accelerator in their Spring 2021 batch, has fully bootstrapped Rails Autoscale. Now, he's working to grow the app, deal with platform risk, and launch pricing experiments. The topics we cover [03:30] Background before starting Rails Autoscale [07:04] Getting to 100 active...
Jun 29, 2021•29 min•Transcript available on Metacast In Episode 556, Rob Walling chats with Adam McCrea about growing from zero to $300,000 in ARR over the course of three years as a Heroku add-on. Adam is still a single founder with no employees and up until joining the TinySeed accelerator in their Spring 2021 batch, has fully bootstrapped Rails Autoscale. Now, he's working to grow the app, deal with platform risk, and launch pricing experiments. The topics we cover [03:30] Background before starting Rails Autoscale [07:04] Getting to 100 active...
Jun 29, 2021•29 min•Transcript available on Metacast In Episode 555, Rob Walling answers listener questions with Ruben Gamez. They discuss different models of bootstrapping success, hiring W2 versus hiring contractors, determining if a business is an ideal fit for bootstrapping and they revisit enterprise pricing. The topics we cover [01:24] Bootstrappers Rob & Ruben admire [12:25] Pros and cons to hiring contractors vs W2 employees [23:05] Determining if an idea is a good fit for bootstrapping [28:31] How to develop competitive pricing for la...
Jun 22, 2021•36 min•Transcript available on Metacast In Episode 555, Rob Walling answers listener questions with Ruben Gamez. They discuss different models of bootstrapping success, hiring W2 versus hiring contractors, determining if a business is an ideal fit for bootstrapping and they revisit enterprise pricing. The topics we cover [01:24] Bootstrappers Rob & Ruben admire [12:25] Pros and cons to hiring contractors vs W2 employees [23:05] Determining if an idea is a good fit for bootstrapping [28:31] How to develop competitive pricing for la...
Jun 22, 2021•36 min•Transcript available on Metacast In Episode 554, Rob Walling chats with Sherry Walling about grief as a part of entrepreneurship and how to get better at handling grief as an entrepreneur. They also discuss burnout and properly evaluating if it's the right time to sell a company. The topics we cover [02:18] Grief is part of entrepreneurship [05:12] Getting better at handling grief and loss [06:07] Grief and selling a company [09:01] The importance of symbols [12:04] Evaluating reasons to sell a company [16:37] The three compone...
Jun 15, 2021•27 min•Transcript available on Metacast In Episode 554, Rob Walling chats with Sherry Walling about grief as a part of entrepreneurship and how to get better at handling grief as an entrepreneur. They also discuss burnout and properly evaluating if it's the right time to sell a company. The topics we cover [02:18] Grief is part of entrepreneurship [05:12] Getting better at handling grief and loss [06:07] Grief and selling a company [09:01] The importance of symbols [12:04] Evaluating reasons to sell a company [16:37] The three compone...
Jun 15, 2021•27 min•Transcript available on Metacast In Episode 553, Rob Walling chats with Tracy Osborn about the latest bootstrapper news, including the recent Stack Overflow and Moz acquisitions, quitting instead of giving up remote work, and highlights from TinySeed 2020 Batch. The topics we cover [01:52] Intro [03:45] Stack Overflow acquisition [12:11] Moz acquisition [16:33] Quitting instead of giving up remote work [26:44] Highlights from TinySeed 2020 Links from the show Episode 545 | The Value of Learning 80/20 Design Fundamentals Episode...
Jun 08, 2021•37 min•Transcript available on Metacast In Episode 553, Rob Walling chats with Tracy Osborn about the latest bootstrapper news, including the recent Stack Overflow and Moz acquisitions, quitting instead of giving up remote work, and highlights from TinySeed 2020 Batch. The topics we cover [01:52] Intro [03:45] Stack Overflow acquisition [12:11] Moz acquisition [16:33] Quitting instead of giving up remote work [26:44] Highlights from TinySeed 2020 Links from the show Episode 545 | The Value of Learning 80/20 Design Fundamentals Episode...
Jun 08, 2021•37 min•Transcript available on Metacast In Episode 552, Rob Walling is joined by co-host emeritus, Mike Taber to chat about his decision-making around whether to launch a freemium plan, whether to do an AppSumo deal, how his potential partnerships merger is panning out. The topics we cover [04:93] Update on the CRM partnership opportunity, AppSumo, and Freemium [23:39] Yet another Google security audit update Links from the show Bluetick.io Episode 535 | A Bluetick Update with Mike Taber MicroConf Remote Episode 543 | All Things Start...
Jun 01, 2021•36 min•Transcript available on Metacast In Episode 552, Rob Walling is joined by co-host emeritus, Mike Taber to chat about his decision-making around whether to launch a freemium plan, whether to do an AppSumo deal, how his potential partnerships merger is panning out. The topics we cover [04:93] Update on the CRM partnership opportunity, AppSumo, and Freemium [23:39] Yet another Google security audit update Links from the show Bluetick.io Episode 535 | A Bluetick Update with Mike Taber MicroConf Remote Episode 543 | All Things Start...
Jun 01, 2021•36 min•Transcript available on Metacast In episode 551 of Startups For the Rest of Us, Rob does another solo adventure to talk about hiring owner-level thinkers, the fallacy of an autopilot passive income software business, and more. The topics we cover [1:25] Hiring task-level thinkers, project-level thinkers, and owner-level thinkers [07:43] The fallacy of an autopilot passive income software business [15:21] Our bootstrap community [20:45] Questions you should ask yourself when building/growing a company Links from the show FE Inte...
May 25, 2021•28 min•Transcript available on Metacast In episode 551 of Startups For the Rest of Us, Rob does another solo adventure to talk about hiring owner-level thinkers, the fallacy of an autopilot passive income software business, and more. The topics we cover [1:25] Hiring task-level thinkers, project-level thinkers, and owner-level thinkers [07:43] The fallacy of an autopilot passive income software business [15:21] Our bootstrap community [20:45] Questions you should ask yourself when building/growing a company Links from the show FE Inte...
May 25, 2021•28 min•Transcript available on Metacast In Episode 550, Rob Walling chats with Tony Chan, co-founder of CloudForecast, about his incredible story of perseverance after getting rejected multiple times only to finally find product-market fit and reach six figures in annual recurring revenue. The topics we cover [04:11] CloudForecast's current revenue and customer base [08:43] Origin story for the idea of CloudForecast [16:53] Dealing with (many) rejections [28:01] Parting ways with a co-founder [30:07] The journey to Product-Market Fit ...
May 18, 2021•44 min•Transcript available on Metacast In Episode 550, Rob Walling chats with Tony Chan, co-founder of CloudForecast, about his incredible story of perseverance after getting rejected multiple times only to finally find product-market fit and reach six figures in annual recurring revenue. The topics we cover [04:11] CloudForecast's current revenue and customer base [08:43] Origin story for the idea of CloudForecast [16:53] Dealing with (many) rejections [28:01] Parting ways with a co-founder [30:07] The journey to Product-Market Fit ...
May 18, 2021•44 min•Transcript available on Metacast In Episode 439, Rob Walling is joined by Jordan Gal to answer listener questions about starting an e-commerce SaaS and the laws and regulations, and compliance requirements required. They talk about managing enterprise perceptions of risk towards bootstrap startups. They also answer questions about bootstrapping and enterprise SaaS as well as hiring a growth role and whether you should hire full-time or outsource to a contractor or an agency. The topics we cover [01:11] Regulatory requirements f...
May 11, 2021•41 min•Transcript available on Metacast In Episode 439, Rob Walling is joined by Jordan Gal to answer listener questions about starting an e-commerce SaaS and the laws and regulations, and compliance requirements required. They talk about managing enterprise perceptions of risk towards bootstrap startups. They also answer questions about bootstrapping and enterprise SaaS as well as hiring a growth role and whether you should hire full-time or outsource to a contractor or an agency. The topics we cover [01:11] Regulatory requirements f...
May 11, 2021•41 min•Transcript available on Metacast May 06, 2021•7 min•Transcript available on Metacast May 06, 2021•7 min•Transcript available on Metacast 
