Startups For the Rest of Us

In episode 536 of Startups For the Rest of Us, Rob does another solo adventure. As we all faced perhaps one of the worst years on record, Rob talks through some things that 2020 taught him personally, professionally, and at a higher level, philosophically. He also looks beyond 2020 and discusses opportunities for 2021 for software entrepreneurs. The topics we cover [01:53] Keeping perspective during difficult startup times [04:03] We can make it through scary and dangerous moments [07:04] There is always opportunity [09:53] Doing things in public creates opportunity [12:02] Growing niches/industries in 2021 [18:31] In search of problems Links from the show Episode 490 | How Founders Should Be Thinking About the Current Crisis Dynamite Jobs 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 have questions about starting or scaling a software business that you’d

In Episode 535, Rob is joined by co-host emeritus, Mike Taber to talk about what Mike has been up to over the past seven months with Bluetick, including an exciting reveal of a big project he's been working on. The topics we cover [05:41] BlueTick partnership or merger with a CRM for field sales reps [11:52] Delays in partnerships from pandemic and potential asymmetric upside [15:42] How far along the CRM software compared to BlueTick? [19:32] Considering freemium and an AppSumo deal [32:48] Another Google security audit Links from the show SonarCloud (mentioned at 17:43) Episode 484 | Marketing That’s Working Today, Moving from 5 to 10 Employees, SaaS Longevity, and More Listener Questions (mentioned at 22:28) AppSumo 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 have questions about starting or scaling a software business that you’d like for us to cover

In this episode, Rob talks with Josh Pigford in a first appearance since the sale of Baremetrics for $4m. They discuss his seven-year journey to build Baremetrics, the details of the sale, and Josh's post-sale, non-software aspirations. The topics we cover [02:42] Intros [04:26] Avoiding capital gains via qualified small business stock. [09:08] Josh's post-sale purchases and other dramatic life shifts [13:46] Changes at Baremetrics after sale [18:32] Weeks of cash to profitable in 8 months [23:20] Breaking through plateaus and product vs marketing for growth out of plateaus [30:13] What motivated Josh to start thinking about selling [32:58] Launching a new feature called Intros in 2020 [39:11] Laser tweets and post-sale aspirations Links from the show Episode 244 | Competition, Transparency and Funding with Baremetrics Founder Josh Pigford Baremetrics: Subscription Analytics & Insights for Stripe, Braintree, Recurly & more! I sold Baremetrics - Baremetrics

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 the link and sharing what you learned. Click here to share your number one takeaway from the episode. 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: iTunes | Spotify | Stitcher

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 show The Art of Selling Your Business Built to Sell: Creating a Business That Can Thrive Without You Built to Sell Radio The Automatic Customer: Creating a Subscription Business in Any Industry Finish Big: How Great Entrepreneurs Exit Their Companies on Top Before The Exit: Thought Experiments For Entrepreneurs 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 ha

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 growth Links from the show The Podcast Host Alitu Hostile Worlds Product/Founder Fit 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 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: iTunes | Spotify | Stitcher

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] Advice on starting a mastermind group in 2021 Links from the show The Mom Test The Personal MBA The Ultimate Sales Letter Traction The Entrepreneur’s Guide to Keeping Your Sh*t Together Start Small Stay Small The Art of Product 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 have questions about starting or scaling a software business that you’d like for

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 Black Airplane MicroConf Masterminds 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 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: iTunes | Spotify | Stitcher

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 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: iTunes | Spotify | Stitcher

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 Bootstrapping to $1 Million in Two Years as a Non-Technical Founder with Christy Laurence of Plann Cities and Ambition Tropical MBA podcast 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 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! Sub

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 Vincent 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 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: iTunes | Spotify | Stitcher

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 [15:10] The counteroffer from Rob's trusted friend [18:41] Business plan vs boots on the ground [20:49] Buying DotNetInvoice 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 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: iTunes 

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 geocoding Geocodio | Website Geocodio | Website Michele Hansen | Twitter Mathias Hansen | Twitter 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 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: iTunes | Spotify |

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 level of customer research should you do? [10:56] What advice would you give to someone entering a somewhat competitive market? [15:55] What questions would you be asking yourself if you had a slow-growing 12k MRR B2B SaaS? [18:22] How would you go about offloading tier-one customer support? [20:28] How do you feel about entrepreneurship being taught to children? [22:24] What are things you noticed that bootstrappers commonly overlooked that are preventing them from achieving their goals? [23

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 experiment work out? [8:92] Merging brands and moving into enterprise offers [19:91] Private podcasting [23:44] What's new and exciting at Castos Links from the show Episode 466 | Answering Listener Questions With Craig Hewitt Episode 493 | A Roundtable Discussion about COVID-19, Working From Home, Payroll Protection and More TinySeed Tales - Season 1 Castos Productions (formerly Podcast Motor) Rogue Startups The SaaS Podcast Award If you enjoyed this episode, let us know by clickin

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 past year and their success (and struggle) with moving upmarket. The topics we cover [01:01] Gather's recent cash crunch Cashflow is not our biggest concern anymore, which is a great relief. Since that time growth has been either sorta normal steady when you average it out or maybe a little slower the last month and a half. Small Business Association loan and PPP loan changed things for us,. One was the loans, the other was that Gather landed a bigger enterprise client who was willing to fund features and who w

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 anti-trust suit [19:23] Dropbox remote offices [27:29] SPACs and why it's so hard to go public in the US [39:35] A warning about Glassdoor Links from the show The 99 Investor Problem U.S. Accuses Google of Illegally Protecting Monopoly Dropbox will let all employees work from home permanently as it turns its offices into WeWork-like 'collaborative spaces' The TinySeed Investment Thesis A Warning About Glassdoor Tracy Osborn | Twitter Einar Vollset | Twitter If you enjoyed

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 [01:14] Status on large enterprise deals One closed, one did not. The first touch with them was almost a year. They had a software proprietary software that they built internally and have been actively seeking a new tool Custom data migration and storage and it was also a bunch of custom development Win-win they got what they wanted and we got some new cool features Big win, I would say, to get paid, to build a feature that you expect other customers to be able to use. Optimistic that maybe we can sort of

In this episode, Rob talks with the founder of SegMetrics, Keith Perhac. SegMetrics is a SaaS product that helps users get clarity on where their leads come from, how they act, and how much their marketing is worth. We dive into the difference between SegMetrics and other options for attributing sales and revenue to traffic channels. We also go through Keith's background and learn about why he shut down his million-dollar marketing agency to double down on his SaaS. The topics we cover [04:28] Where does SegMetrics fit within the analytics and attribute market? [09:35] Why build a SaaS when you are running a 7 figure agency [12:56] Dealing with a growth plateau [21:28] Shifting focus to work on SegMetrics full-time [28:05] Frugality as a bootstrapper (and how it can backfire) Links from the show SegMetrics | Twitter SegMetrics | Website Keith Perhac | Twitter If you enjoyed this episode, let us know by clicking the link and sharing what you learned. Click here to sh

Brian & Scottie Elliott are the husband & wife co-founders of Gather, an interior design project management app. Today's episode was recorded after the COVID-19 shelter in place orders went into effect. We talk with Brian and Scottie about how the pandemic has affected Gather as well as their life beyond the scope of their business. The topics we cover [01:10] How the pandemic has affected their lives beyond the scope of their business. Brian and Scottie live in Mexico Living in almost what feels like two worlds here. The ex-pat community is very tuned into what's happening in the US and sheltering in place [03:11] Current financial situation Our situation hasn't changed financially. I think that at the time we had hopes that we could raise some money or at least get alone. We're not even pursuing that at this point We're certainly used to bootstrapping and feeling that stress and coming up with interesting solutions to our cash problems. [05:57] High point or biggest wins since the last