Startups For the Rest of Us

In episode 639, Rob Walling chats with Andrew Berkowitz, the co-founder and CEO of Suggestion Ox, about the secret sauce to building happy, high-performing teams and how we as founders need to unlearn some of the strict policies that have been in place for hundreds of years. Suggestion Ox is a feedback platform that helps HR teams build candid communication between leadership and employees. And before that, Andrew co-founded a sports management platform that was acquired in 2021. Episode Sponsor: Find your perfect developer or a team at Lemon.io/startups The competition for incredible engineers and developers has never been more fierce. Lemon.io helps you cut through the noise and find great talent through its network of engineers in Europe and Latin America. They take care of the vetting, interviewing, and testing of candidates to make sure that you are working with someone who can hit the ground running. When it comes to hiring, the time it takes to write your job description, list the position, review resumes, schedule interviews, and make an offer can take weeks, if not months. With Lemon.io, you can cut down on a lot of that time by tapping into their wide network of developers who can get started in as early as a week. And for subscribers of Startups For the Rest of Us, you can get 15% off your first 4 week contract with a developer by visiting lemon.io/startups Topics we cover: 2:10 - Why trust is the key ingredient when building high-performing teams 6:56 - Flexible vacation policies 9:17 - Flexible work hours 15:08 - The link between remote work and hiring and retaining great employees 18:14 - Using transparency to build trust with your team 19:43 - How transparent should you be with your team for temporary issues? 21:55 - Does this approach to trust and transparency work at scale? 25:57 - Getting better at giving constructive feedback as a manager 28:20 - Is it possible to hire the best people at scale? 32:08 - Andrew’s approach to dealing with bad apples or people who slack off 36:41 - Building a company culture where employees feel safe to give candid feedback Links from the Show: Andrew Berkowitz I Twitter Suggestion Ox

In episode 638, Rob Walling chats with Justin Vincent about how to generate startup ideas. They share 8 startup ideas in this episode along with Justin’s approach for coming up with thousands of startup ideas. Topics we cover: 1:58 - Coming up with SaaS ideas 3:51 - Transcription for team meetings 11:42 - Online time capsule 15:41 - Pest control using drones 20:29 - Prerecorded live interviews 25:06 - Special diet builder 26:30 - AI-casting director 29:53 - Cash burn alert for VC 31:47 - database modeling tool Links from the Show: Justin Vincent (@justinvincent) I Twitter Nugget.one Techzing Episode 526 I Launching, learning and teaching with Justin Vincent 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 episode 637, join Rob Walling for another solo adventure as he answers a handful of listener questions. Topics covered range from hiring your first salesperson and acquiring a web app to dealing with the fear of having your idea copied and why bootstrapping a two-sided marketplace is usually a bad idea. Episode Sponsor: Find your perfect developer or a team at Lemon.io/startups The competition for incredible engineers and developers has never been more fierce. Lemon.io helps you cut through the noise and find great talent through its network of engineers in Europe and Latin America. They take care of the vetting, interviewing, and testing of candidates to make sure that you are working with someone who can hit the ground running. When it comes to hiring, the time it takes to write your job description, list the position, review resumes, schedule interviews, and make an offer can take weeks, if not months. With Lemon.io, you can cut down on a lot of that time by tapping into their wide network of developers who can get started in as early as a week. And for subscribers of Startups For the Rest of Us, you can get 15% off your first 4 week contract with a developer by visiting lemon.io/startups Topics we cover: 1:14 - You either die a consumer startup hero, or you live long enough to see yourself become a B2B SaaS founder. 2:40 - Hiring your first salesperson 9:36 - Bootstrapping a talent marketplace 15:10 - Acquiring a web app 19:40 - Getting over your fear of being copied when doing idea validation interviews Links from the Show: Daniel Nguyen (@daniel_nguyenx)’s tweet The Mom Test 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 episode 636, Rob Walling chats with Claire Suellentrop about the new book she co-wrote with her co-founder, Georgiana Laudi. The book is called Forget the Funnel: A Customer-Led Approach to Driving Predictable Recurring Revenue. Gia and Claire have run a consulting firm for the past several years where they are working with startups and SaaS companies to help them learn more about their customers in order to drive more revenue. And this book is a distillation of their learnings. Topics we cover: 1:09 - Why did Claire name their new book, Forget the Funnel? 2:36 - A three-step approach for unlocking customer-led growth 3:09 - A framework for getting inside your customers’ heads 14:01 - How to learn from future customers 20:21 - Applying and operationalizing all your customer insights Links from the Show: Claire Suellentrop (@ClaireSuellen) I Twitter Georgiana Laudi (@ggiiaa) I Twitter Forget The Funnel: a Customer-Led Approach to Driving Predictable, Recurring Revenue The Jobs-to-be-Done Handbook: Practical techniques for improving your application of Jobs-to-be-Done Deploy Empathy: A practical guide to interviewing customers Obviously Awesome: How to Nail Product Positioning so Customers Get It, Buy It, Love It Episode 537 | On Launching, Funding, and Growth with Serial SaaS Founder Rand Fishkin Sparktoro MicroConf Growth 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 episode 635, Rob Walling catches up with Tony Chan, the co-founder of CloudForecast, an AWS cost monitoring tool. Tony shared his victories, challenges, and failures in TinySeed Tales Season 3. It has been over eight months since we recorded the final episode. In this episode, we reflect and catch up on what’s been happening with Tony and CloudForecast. Episode Sponsor: Find your perfect developer or a team at Lemon.io/startups The competition for incredible engineers and developers has never been more fierce. Lemon.io helps you cut through the noise and find great talent through its network of engineers in Europe and Latin America. They take care of the vetting, interviewing, and testing of candidates to make sure that you are working with someone who can hit the ground running. When it comes to hiring, the time it takes to write your job description, list the position, review resumes, schedule interviews, and make an offer can take weeks, if not months. With Lemon.io, you can cut down on a lot of that time by tapping into their wide network of developers who can get started in as early as a week. And for subscribers of Startups For the Rest of Us, you can get 15% off your first 4 week contract with a developer by visiting lemon.io/startups Topics we cover: 3:03 - Losing one of CloudForecast’s engineers 5:35 - Tony’s approach to hiring engineers 8:31 - Did Tony end up hiring someone to help with content marketing? 17:32 - What is Tony struggling with right now? 21:07 - Managing your founder psychology 25:08 - Tony’s recent conundrum Links from the Show: Tony Chan (@toeknee123) I Twitter CloudForecast TinySeed Tales Season 3 MicroConf Local: Austin 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 episode 634, join Rob Walling for another solo adventure where he answers listener questions on topics ranging from naming your startup to initial aha moments and how to know if you have tapped out a specific niche. Episode Sponsor: Find your perfect developer or a team at Lemon.io/startups The competition for incredible engineers and developers has never been more fierce. Lemon.io helps you cut through the noise and find great talent through its network of engineers in Europe and Latin America. They take care of the vetting, interviewing, and testing of candidates to make sure that you are working with someone who can hit the ground running. When it comes to hiring, the time it takes to write your job description, list the position, review resumes, schedule interviews, and make an offer can take weeks, if not months. With Lemon.io, you can cut down on a lot of that time by tapping into their wide network of developers who can get started in as early as a week. And for subscribers of Startups For the Rest of Us, you can get 15% off your first 4 week contract with a developer by visiting lemon.io/startups Topics we cover: 2:38 - Naming your startup 6:02 - How to know if you tapped out a specific niche? 13:21 - Did you have an initial aha moment when you felt that this was the winning idea to start up? 22:25 - How would you value your time if you have a client that is gonna be competing in the same space? Links from the Show: MicroConf Europe 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 episode 633, Rob Walling chats with Matt Wensing, the founder of Summit. Matt is no stranger on the podcast. And we talk about Matt's decision to change Summit's brand positioning and the far-reaching impact on his business. Episode Sponsor: Find your perfect developer or a team at Lemon.io/startups The competition for incredible engineers and developers has never been more fierce. Lemon.io helps you cut through the noise and find great talent through its network of engineers in Europe and Latin America. They take care of the vetting, interviewing, and testing of candidates to make sure that you are working with someone who can hit the ground running. When it comes to hiring, the time it takes to write your job description, list the position, review resumes, schedule interviews, and make an offer can take weeks, if not months. With Lemon.io, you can cut down on a lot of that time by tapping into their wide network of developers who can get started in as early as a week. And for subscribers of Startups For the Rest of Us, you can get 15% off your first 4 week contract with a developer by visiting lemon.io/startups Topics we cover: 2:24 - Matt’s decision to change Summit’s positioning 15:22 - Redesigning Summit’s website 22:39 - The dangers of scaling up before you have product-market fit 24:43 - The response to Summit’s relaunch 29:33 - How Summit is evolving into a 2-sided marketplace Links from the Show: Matt Wensing (@MattWensing) I Twitter Summit MicroConf Remote 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 episode 632, join Rob Walling and Einar Vollset for Hot Take Tuesday, where they analyze and discuss some of the latest news. Some topics covered include the Figma exit, side project distractions, no-code apps, and more. Episode Sponsor: Find your perfect developer or a team at Lemon.io/startups The competition for incredible engineers and developers has never been more fierce. Lemon.io/ helps you cut through the noise and find great talent through its network of engineers in Europe and Latin America. They take care of the vetting, interviewing, and testing of candidates to make sure that you are working with someone who can hit the ground running. When it comes to hiring, the time it takes to write your job description, list the position, review resumes, schedule interviews, and make an offer can take weeks, if not months. With Lemon.io/, you can cut down on a lot of that time by tapping into their wide network of developers who can get started in as early as a week. And for subscribers of Startups For the Rest of Us, you can get 15% off your first 4 week contract with a developer by visiting lemon.io/startups Topics we cover: 2:35 - Adobe acquires Figma 8:20 - Growing one product to $20k MRR vs. launching a bunch of side projects 18:43 - Apple’s anti-ad tracking crackdown 25:58 - Building no-code apps 31:12 - Watching movies at 1.5x speed Links from the Show: Einar Vollset (@einarvollset) I Twitter MicroConf Remote Adobe snaps up Figma for $20 billion Pierre de Wulf’s tweet Apple’s ad business set to boom on the back of its own anti-tracking crackdown Hana’s tweet Ruben’s tweet 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 631, join Rob Walling for a solo adventure as he answers listener questions on topics ranging from when to rewrite your codebase to founder salaries and balancing your founder vs. developer mindset. Episode Sponsor Find your perfect developer or a team at Lemon.io The competition for incredible engineers and developers has never been more fierce. Lemon.io helps you cut through the noise and find great talent through its network of engineers in Europe and Latin America. They take care of the vetting, interviewing, and testing of candidates to make sure that you are working with someone who can hit the ground running. When it comes to hiring, the time it takes to write your job description, list the position, review resumes, schedule interviews, and make an offer can take weeks, if not months. With Lemon.io, you can cut down on a lot of that time by tapping into their wide network of developers who can get started in as early as a week. And for subscribers of Startups For the Rest of Us, you can get 15% off your first 4 week contract with a developer by visiting lemon.io/startups Topics we cover: 2:32 - Is there any validity that rewriting our code and changing our tech stack will get us to a higher multiple at a future exit? 8:08 - Founder salaries 12:16 - Using the stair step approach to create a course 15:20 - Can you sell a Zapier-type connection between several products as an early MVP for your target market? 20:06 - Founder mindset vs. developer mindset Links from the Show: Episode 622 I Making Hard Product Decisions & Growth vs. Profitability with Derrick Reimer The Stair Step Approach to Bootstrapping 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 episode 630, Rob Walling chats with Jonathan Weinberg, who is the founder of Builder Prime, a CRM software for home improvement contractors. We chat about how he came up with the idea for Builder Prime, getting early traction, and finding product-market fit. Topics we cover: 2:46 - Getting Builder Prime to almost $1M ARR 3:32 - Deciding who to hire next 4:40 - How did Jonathan come up with the idea for Builder Prime? 8:29 - Jonathan's decision to quit his day job and work on Builder Prime before it made any money 10:55 - The unique steps that Jonathan took to get early traction 17:05 - When did Jonathan realize he had product-market fit? 24:04 - Jonathan’s hockey stick growth moment 28:31 - What’s next for Jonathan? Links from the Show: Jonathan Weinberg @Jonathan_codes) I Twitter Builder Prime TinySeed 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 the final episode of TinySeed Tales Season 3, Rob Walling checks in with Tony Chan of CloudForecast. They reflect on some of the most prominent challenges and milestones that the business has faced over the last year. Topics we cover: 1:31 - Tony reflects on attending his first MicroConf Growth in Minneapolis 3:30 - An update on how CloudForecast’s content marketing efforts are going 7:59 - Getting an article featured at the top of Reddit 11:16 - An update on how their new senior engineer is doing 16:18 - Why Tony prefers to hire full-time employees 18:26 - An update on CloudForecast’s sales pipeline 20:50 - Tony reflects on the challenges of figuring out where to invest time and capital 24:30 - The importance of getting low-level tasks off your plate 28:36 - What is Tony least looking forward to in the next year? 30:38 - What is Tony most looking forward to in the next year? Links from the Show: Tony Chan (@toeknee123) I Twitter CloudForecast Cost of living the cloud life: Fossil fuel consumption as a service 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 episode 628, join Rob Walling on a solo adventure where he dives into his newest framework. The 5 PM Pre-Validation Framework is a helpful way to evaluate different startup ideas through a set of criteria to gauge the size of the opportunity. Want to download the PDF version the the 5 PM Pre-Validation Framework? Join the Startups For The Rest Us Mailing List, and we'll send you the link in the first email. Look for the orange email opt-in widget on the page. Topics we cover: 3:37 - Why is it called The 5 P.M. Idea Validation Framework? 4:06 - Problem 6:23 - Purchaser 8:17 - Pricing Model 9:00 - Market 12:48 - Product-Founder Fit 13:21 - Pain to validate the product 13:59 - Evaluating two business ideas through Rob’s 5PM framework Links from the Show: SaaS Ideas to Build Right Now, Before Someone Else Does Jon Yongfook's Tweet MicroConf Connect 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 the penultimate episode of TinySeed Tales Season 3, Rob Walling checks in with Tony Chan of CloudForecast. Tony shares some recent big wins, including hiring a senior engineer. We also meet Tony’s cofounder, Francois Lagier, for the first time. Topics we cover: 1:49 - The story of how Tony and Francois first met 2:14 - Hiring a senior engineer at CloudForecast 8:51 - Tony shares two recent big wins at CloudForecast 14:31 - The paradox of choice that all startup founders face 16:30 - CloudForecast dives into some new content marketing and SEO initiatives 18:35 - What are Tony and Francois looking forward to in the next month? Links from the Show: Tony Chan (@toeknee123) I Twitter Francois Lagier (@francoislagier) I Twitter CloudForecast 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 episode 626, Rob Walling chats with Nick Swan, the founder of SEOTesting.com. SEOTesting helps SEO professionals and agencies automate the reporting of page updates and changes. Nick originally launched it as a free tool under a different name. In this episode, we cover when Nick decided to charge for it, renaming the tool, rewriting the codebase, and the journey to growing to $18,000 MRR. Topics we cover: 3:17 - Growing SEOTesting.com to $18,000 MRR 4:53 - What kinds of businesses use SEOTesting.com? 8:11 - The decision to build SEOTesting 12:33 - Launching SEOTesting as a free tool 15:39 - When Nick started to charge for SEOTesting? 18:16 - Nick’s initial pricing strategy and rollout 27:06 - Reflecting on the initial launch 29:49 - Nick’s thought process for pivoting and changing the company name 34:45 - Reaching product-market fit 36:01 - Nick’s decision to bring on a co-founder a few years in 39:32 - Prioritizing marketing vs. development Links from the Show: Nick Swan (@NickSwan) I Twitter SEOTesting.com TinySeed 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 the fourth episode of TinySeed Tales Season 3, Rob Walling checks back in with Tony Chan of CloudForecast. Tony shares that they’ve doubled their MRR in the last couple of months, and it feels like he has unlocked a cheat code. Topics we cover: 2:02 - What’s changed since the last episode? 3:14 - Winning a huge enterprise deal that nearly doubled their MRR 5:21 - Deploying capital 12:31 - A key mindset shift that Tony had to make 13:33 - Tony’s experience at a recent TinySeed retreat 18:10 - Tony reflects on some low points 19:35 - What is he looking forward to? Links from the Show: Tony Chan (@toeknee123) I Twitter CloudForecast TinySeed Applications are now open 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 episode 624, join Rob Walling for a solo adventure as he answers some listener questions on topics ranging from customer interviews to transitioning from a free to a paid product and prioritizing marketing vs. development. Topics we cover: 2:11 - What episodes should I start with to get up to speed? 3:27 - When to transition from a free to a paid product 11:37 - Customer interviews as a service 15:03 - Making the jump from software to manufacturing 19:32 - Prioritizing marketing vs. development Links from the Show: Greatest Hits Spending Benchmarks for Private B2B SaaS Companies How Much Do SaaS Companies Spend on Marketing? MicroConf Locals MicroConf Youtube Channel MicroConf Connect 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 the third episode of season 3 of TinySeed Tales, Rob Walling checks in with Tony Chan of CloudForecast to see how he is faring since his co-founder is now on paternity leave. During this time, Tony shares a big win along with dealing with some hiring and growth setbacks. Topics we cover: 1:24 - How the business is doing while Francois is on paternity leave 2:36 - Tony’s perspective on being a solo founder for the past 6 weeks 5:04 - Managing your own founder psychology 7:49 - How Tony is dealing with an unexpected sales slump 16:16 - Did Tony end up hiring a full-time SDR? 21:04 - Dealing with setbacks 22:41 - What Tony is looking forward to in the next couple of months Links from the Show: Tony Chan (@toeknee123) I Twitter CloudForecast TinySeed Applications are now open Episode 613 | Hacking Your Founder Psychology Summit 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 episode 622, join Rob Walling and fan favorite Derrick Reimer, the founder of SavvyCal, as they discuss topics like balancing profitability versus growth and deciding which features to build and not. They chat about some specific features that Derek has decided to build, those he has not decided to build, and the thought process behind them. Topics we cover: 4:02 - Making product decisions 9:22 - Deciding on what features you are not going to build 19:12 - When to reply to debates on Twitter 27:42 - Twitter’s newsletter feature 31:40 - Derrick’s perspective on balancing profitability vs reinvesting in the business 43:10 - Is Rob scratching his maker itch by being an investor in companies through TinySeed, or is he missing building SaaS businesses? 46:29 - Should Rob join TikTok? Links from the Show: Derrick Reimer @derrickreimer I Twitter SavvyCal Applications for TinySeed’s Fall 2022 SaaS Accelerators Are Now Open MicroConf Youtube Channel High Signal 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 of TinySeed Tales, Rob chats with Tony Chan from CloudForecast about the progress his rapidly growing team has made over the previous few weeks. Tony is riding the roller coaster that is entrepreneurship and in this episode you get to follow along. Topics we cover: 1:47 - New full time engineering hire onboarding results 4:50 - Part time SDR hire onboarding results 7:31 - How hiring affects company culture 10:19 - Tony’s biggest wins in the last few weeks 14:30 - Growing the product to grow Expansion Revenue 15:45 - CloudForecast’s summer sales lull 19:40 - Keeping sane as a founder 22:00 - What Tony is worried about coming out of summer 24:00 - The next MRR target Links from the Show: Tony Chan (@toeknee123) I Twitter CloudForecast TinySeed Applications open September 12, 2022 TinySeed Tales S2E1 I Introducing Gather TinySeed Tales 1 I A Non-Technical Saas Founder 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 episode 620, join Rob Walling for a solo adventure as he answers some listener questions. These questions range from which SaaS business metrics to pay attention to and how to find good SaaS ideas to helping an employee transition from a task-level to a project-level thinker. Topics we cover: 1:44- What SaaS business metrics matter the most? 11:21- Do you have any general observations about building a SaaS for non-technical customers? 16:00- How do you find a good SaaS idea? 24:41- How can I assist an employee in transitioning from a task-level to a project-level thinker? Links from the Show: Episode 480 I Stairstepping Your Way To SaaS with Christopher Gimmer 2022 State of Independent SaaS Report The Stairstep Approach to Bootstrapping TMBA 100 - Rip, Pivot, and Jam MicroConf Connect MicroConf Europe Applications for TinySeed’s Fall 2022 SaaS Accelerators Will Open September 12th MicroConf Youtube Channel 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

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 CloudForecast team? 6:54- Why did Tony apply to TinySeed? 8:30- Why Tony turned down venture capital offers? 13:48- Tony reflects on the added complexity of taking funding 19:47- Tony’s biggest fear 22:34- What is Tony looking forward to? Links from the Show: Tony Chan (@toeknee123) I Twitter CloudForecast TinySeed Castos Gather TinySeed Tales S2E1 I Introducing Gather TinySeed Tales S1E1 I A Non-Technical Saas Founder 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.

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 navigate the US health insurance system as an early retiree 12:10- Sam’s relentless execution when it comes to running Financial Samurai 17:40- How Sam learned about personal finance 18:47- How Sam negotiated a severance package despite quitting his investment banking job 22:47- Why he runs Financial Samurai as a true lifestyle business 26:07- Would Sam sell Financial Samurai for $20 million? 27:35- The premise of Sam’s new book 28:46- Sam’s mental model for allocating financial assets to generate passive income Links from the Show: Sam Dogen (@financialsamura) I Twitter Financial Samurai Buy This, Not That TropicalMBA MicroConf Europe Applications for TinySeed’s Fall 2022 SaaS Accelerators Will Open September 12th MicroConf Youtube Channel 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 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 founder Links from the Show: Tracy Osborn @tracymakes I Twitter Einar Vollset @einarvollset I Twitter Episode 611 | Bootstrapping ProfitWell to a $200M Exit (with Patrick Campbell) Watching an acquirer ruin your company Episode 605 | Building a SaaS with Little Dev Experience, Using No Code for Your MVP, Bootstrapping a Two-Sided Marketplace, and More Listener Questions The “Spreadsheet Mentality” sucks, and kills the efficacy of jobs If You Can’t Buy It Twice, Don’t Buy It 14 Critical Things Investors Look for In A SaaS Startup Applications for TinySeed’s Fall 2022 SaaS Accelerators Will Open September 12th MicroConf Youtube Channel MicroConf Europe 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 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 experienced developer or even an entire team easier. They only have experienced developers on their marketplace, and each one is hand-vetted. It is virtually risk-free as they’ll guarantee a replacement in 48 hours if something goes wrong. Find your perfect developer or a team with Lemon.io. You can also claim a special discount for our podcast fans. Visit lemon.io/startups to receive a 15% discount for the first 4 weeks of work with a developer. Topics we cover: [2:46] What Liam has learned running Time Doctor for the past 12 years [6:23] Can extroverts thrive long-term in a remote work environment? [11:14] Liam’s approach to metrics and KPIs for engineering teams [18:23] Why remote companies that move faster collaborate less [21:31] How far can you take async communication in a remote team [24:29] Combating isolation on remote teams Links from the Show: Liam Martin (@LiamRemote) I Twitter Running Remote Book Time Doctor Deep Work: Rules for Focused Success in a Distracted World MicroConf Youtube Channel 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 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, and each one is hand-vetted. It is virtually risk-free as they’ll guarantee a replacement in 48 hours if something goes wrong. Find your perfect developer or a team with Lemon.io. You can also claim a special discount for our podcast fans. Visit lemon.io/startups to receive a 15% discount for the first 4 weeks of work with a developer. Topics we cover: [1:51] What makes a business bootstrappable? [14:15] Cargo culting [20:05] How large of a business can you build at a specific annual contract value or lifetime value? Links from the Show: Bootstrapper’s Guide to Outside Funding Episode 613 I Hacking Your Founder Psychology Episode 602 I Explaining SaaS Metrics to a Child 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 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 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, and each one is hand-vetted. It is virtually risk-free as they’ll guarantee a replacement in 48 hours if something goes wrong. Find your perfect developer or a team with Lemon.io. You can also claim a special discount for our podcast fans. Visit lemon.io/startups to receive a 15% discount for the first 4 weeks of work with a developer. Topics we cover: [2:18] Derrick’s decision to take a break from The Art of The Product podcast [10:22] When should you go full-time on your startup? [17:20] Before looking for tech firms, should I know the best frontend and backend architecture for my SaaS MVP and then only shop for firms who specialize in that? [24:13] I'm starting a new SaaS business, and despite a previous successful experience, I can't stop feeling extremely anxious about it. Is this something you're familiar with? How did you deal with it? [30:34] When choosing a domain name for my startup, should you go with a meaningful and expressive name, but a less serious TLD.io or a somewhat fictional name combined with the best tld.com? Links from the Show: Derrick Reimer @derrickreimer I Twitter SavvyCal The Art of Product Bootstrapped Web Summit TinySeed Bullet Train MicroConf Connect The Entrepreneur’s Guide to Keeping Your Shit Together: How to Run Your Business Without Letting it Run You The Mom Test

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 process of hiring an experienced developer or even an entire team easier. They only have experienced developers on their marketplace, and each one is hand-vetted. It is virtually risk-free as they’ll guarantee a replacement in 48 hours if something goes wrong. Find your perfect developer or a team with Lemon.io. You can also claim a special discount for our podcast fans. Visit lemon.io/startups to receive a 15% discount for the first 4 weeks of work with a developer. Topics we cover: [4:04] What it is like to publish a book with a traditional publisher [5:30] The process of launching and promoting a book [9:24] A clever way to reframe cold outreach [15:52] Hacking your founder psychology [21:03] A short book summary Links from the Show: Sherry Walling (@SherryWalling) I Twitter Zen Founder Touching Two Worlds: A guide for finding hope in the landscape of loss Episode 585 I Moving Outside Your Comfort Zone with Dr. Sherry Walling 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 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 expanding Recapture [5:34] The decision to go full-time on Recapture [15:05] Dave’s process for unlearning bad employee / consultant habits [20:07] The danger of the arrival fallacy [24:20] What would you do if you sold the business? [26:03] Balancing a side project with your day job Links from the Show: Dave Rodenbaugh (@DaveRodenbaugh) I Twitter Recapture Rogue Startups 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 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 deciding whether to sell. Topics we cover: [3:53] Using their consulting business to fund and grow Profitwell in the early days [8:23] The split between cash and stock in Profitwell’s acquisition [9:49] The percentage of Profitwell’s revenue from consulting vs. SaaS [13:39] The conversations that Patrick and his cofounders had from the get-go about their end goals and how much to reinvest in the business [15:02] The ownership split between all of the cofounders [17:08] How he made sure his employees were taken care of in the acquisition [19:05] Did Patrick ever consider taking funding? [26:14] How long it took to sell the business from the first contact with Paddle [31:55] Why should SaaS founders take money off the table once they hit certain milestones? [36:01] Patrick’s feelings about competing with Stripe [42:15] Why Patrick moved to Puerto Rico Links from the Show: Patrick Campbell (@Patticus) I Twitter Profitwell Paddle 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 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 starting over today [19:22] The benefits of starting a business today vs. 10 years ago Links from the Show: Episode 551 I Task-level vs. Project-level Thinkers, No such Thing as an Autopilot Business, and More The Stair Step Approach to bootstrapping Quiet Light 68 B2B SaaS marketplaces with opportunities for indie hackers 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 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 improvements when it feels like you don't have time to do anything but fix bugs and answer support tickets? [13:01] Do you have any advice around how to build a complex mobile app MVP in a capital efficient manner? [20:30] Should internal company, marketing and transactional emails be on the same domain? [22:27] How do you plan for a large project? Links from the Show: Episode 551 I Task-level vs. Project-level Thinkers, No such Thing as an Autopilot Business, and More MicroConf Connect Episode 505 I 42 Side Projects and the #NoCode Movement Github Issues Episode 311 I What’s It’s Like Selling a $128k Side Project 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 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 including Adrian’s decision to start blogging and launch a Kickstarter campaign in the early days to learning how to hire employees and making the decision to sell the business in 2021. 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 Hub is a platform that provides founders with free resources to help solve startup challenges, including access to Azure credits, development tools like Github, mentorship resources, Microsoft collaboration and productivity software like Teams and Outlook and more. The program is open to all and takes 5 minutes to sign up, with no funding required. Learn more aka.ms/startupsfortherestofus Topics we cover: [2:41] The story of how Adrian first discovered MicroConf [6:29] Why Adrian didn’t want to go down the traditional path after getting his PhD in computer science [10:01] When he knew having a traditional day job as an employee wasn’t for him [11:24] How he used the stair-step approach to launch PyImageSearch [13:54] What Adrian did when he started to see early traction [16:45] Did having a PhD in computer science have a big impact in the early days of launching his business? [18:05] Adrian’s approach to learning how to market [20:31] How he balanced working a day job and his side business in the early days [23:39] Adrian’s launch plan for selling his first ebook in 2014 [28:48] The epiphanies that Adrian had in the early days to keep plugging away [33:33] How he went from making $38,000 in 2014 to $600,000 in 2016 as a company of one [36:28] The mindset shifts he had to make when he started hiring employees [39:10] Adrian’s decision to sell the business [45:03] His reflections after selling the business in 2021 Links from the Show: Adrian Rosebrock @InfoProdMastery I Twitter PyImageSearch Info Product Mastery The Stair Step Approach to Bootstrapping Ryan Delk: Lifting The Veil: The Data Behind Successful Product Launches I Youtube Quiet Light If you have questions about starting or scaling a software business that...

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? Links from the Show: Asia Orangio (@AsiaOrangio) I Twitter DemandMaven In Demand Productize & Scale SaaS Metrics MicroConf Youtube Channel 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 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 [12:39] Spotify vs. Apple [16:31] Staying up to speed as CEO once you have a team doing the day-to-day tasks [28:32] Implementing OKRs at Castos [33:07] Castos’ Mission Links from the Show: Craig Hewitt (@TheCraigHewitt) I Twitter Castos MicroConf Local Seeking Scale Rogue Startups Bootstrapped Web Tempo I Castos 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 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 service to validate a SaaS idea before building it? [20:47] Can you use the stairstep method to bootstrap a two-sided marketplace business? [31:34] Is no-code something you see mainly for building an MVP, or is it something that you could sustainably build an actual SaaS startup on without running into scaling issues? What are the downside risks to no-code tools other than platform risk? [37:08] Do you think no-code tools will ever get to the point where you can build a full SaaS business? Links from the Show: Ruben Gamez (@earthlingworks) I Twitter SignWell RocketGems Castos Bubble Airtable Dynamite Jobs Clarity.fm MicroConf Masterminds The SaaS Founder Guide to No-Code 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 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] Derrick’s mental framework for deciding what features to build next [23:58] Switching from an employee to a founder mindset [25:56] Would you rather fight one duck-sized horse or a thousand duck-sized horses? [27:25] The best purchase Derrick has made for under $100 in the last 6 months [33:14] The best purchase Derrick has made for under $1000 in the last 6 months Links from the Show: Derrick Reimer (@DerrickReimer) I Twitter SavvyCal Squadcast 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 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 cover: [5:07] How David initially financed building Hotjar [8:11] The biggest difference between Hotjar and its competitors [12:03] The unique approach that David took when launching Hotjar [12:44] Lessons learned from a failed product launch prior to Hotjar [15:01] How they built their initial launch list to 60,000 subscribers [19:32] How to know how much to spend on paid ads [24:53] Why David said it was easy to work 60-80 hour workweeks for the first 6-9 months of Hotjar [27:22] The two key ingredients needed if you want to sell a low-priced SaaS product [30:31] How they tripled their growth from $1M - $3M in the first year [33:26] How their initial launch strategy gave them a major competitive advantage when they started doing content marketing later on [34:03] What led him to sell Hotjar [40:39] How long the exit process took Links from the Show: David Darmanin @DavidDarmanin I Twitter Hotjar Episode 569 I The Life-Changing Decision of When to Sell your Company How a 7-hour workweek led to Anna Maste’s 7-figure sale I They Got Acquired Conversion Rate Experts Delivering Happiness Selling The Invisible The Dip Built to Sell The Great CEO Within Let My People Go Surfing Just Cause If you have questions about starting or scaling a software business that you’d like for us to cover, please

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 mission to help all founders innovate and grow no matter their background, location, or progress. Microsoft for Startups Founders Hub is a platform that provides founders with free resources to help solve startup challenges, including access to Azure credits, development tools like Github, mentorship resources, Microsoft collaboration and productivity software like Teams and Outlook and more. The program is open to all and takes 5 minutes to sign up, with no funding required. Learn more aka.ms/startupsfortherestofus Topics we cover: [1:55] MicroConf Local London tickets are on sale [3:17] Starting with the basics: money, dollars, and businesses [7:01] Revenue [7:12] Expenses [10:51] SaaS [13:29] Recurring revenue [13:58] Average revenue per account (ARPA) [14:56] Monthly recurring revenue (MRR) [15:08] Average revenue per customer [17:08] Annual contract value (ACV) [18:18] Churn [19:30] Differences between Revenue Churn and Customer Churn [21:18] Lifetime value [22:10] Average customer lifetime value [25:49] Customer Acquisition Cost (CAC) 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 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 down on ChurnKey [9:06] A piece of advice for bootstrappers looking for SaaS business ideas [14:44] The process Nick and his cofounder used to sell Wavve for a life-changing exit. [22:13] The potential pitfalls of off-market deals [26:56] His initial reaction after selling Wavve [29:04] The key differences between selling B2B and B2C [30:36] Why Nick made the difference to hire a head of sales for ChurnKey [32:14] The mindset shifts he had to unlock around shifting from low touch to high touch sales [33:43] Why he decided to join the current batch of TinySeed Links from the Show: Nick Fogle (@nickfogle) I Twitter Churnkey Wavve TinySeed 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 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 background, location, or progress. Microsoft for Startups Founders Hub is a platform that provides founders with free resources to help solve startup challenges, including access to Azure credits, development tools like Github, mentorship resources, Microsoft collaboration and productivity software like Teams and Outlook and more. The program is open to all and takes 5 minutes to sign up, with no funding required. Learn more aka.ms/startupsfortherestofus Topics we cover: [1:04] A mental framework for deciding what things you should focus on as a SaaS founder vs. what to delegate [7:28] The importance of resting and taking proper breaks as a SaaS founder [14:28] When to hire your first manager [14:50] The two main components of management: supervising and leading [18:45] The importance of continuous iterations [26:21] Why you need to manage your own psychology as a founder [28:11] Hitting a big podcast milestone: 600 episodes Links from the Show: Strawberry Fields I Beatles Yesterday I Beatles Episode 200: Customer Acquisition Plans for Bootstrappers 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 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 like working on a company with your spouse, and much more. Topics we cover: [2:20] How Dom and Tracy came up with the idea for CodeSubmit [6:59] The approach they used to build their product MVP on nights and weekends [11:16] Running a startup with your spouse [13:42] The catalyst that led to their hockey stick growth moment [17:06] When they knew they had product market fit [21:46] The number of different marketing channels they tried before they decided to double down on content marketing and SEO [26:19] The biggest mistakes that hiring managers and recruiters make when vetting new developers via take-home challenges [29:40] Thoughts on building a lifestyle business Links from the Show: CodeSubmit Dominic Phillips @domrdy I Twitter Tracy Phillips @tracy_s9z I Twitter ScrapingBee 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 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 Startups Founders Hub is a platform that provides founders with free resources to help solve startup challenges, including access to Azure credits, development tools like Github, mentorship resources, Microsoft collaboration and productivity software like Teams and Outlook and more. The program is open to all and takes 5 minutes to sign up, with no funding required. Learn more aka.ms/startupsfortherestofus Topics we cover: [1:21] MicroConf Remote 4.0 [1:59] Improving diversity in the startup ecosystem [8:11] Is bootstrapping the great equalizer in business? [8:51] The right time to work on company values, mission statements, and philosophy [14:02] Developing features for a new app [15:18] How to figure out your minimum lovable product [21:18] How to find business ideas Links from the Show: State of Independent SaaS The Updated Survival Guide for Bootstrapping SaaS I MicroConf On Air Episode 589 I Finding a SaaS idea through 70 cold calls My First Million Tropical MBA 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 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 entrepreneurial journey. Topics we cover: [1:49] Tickets for MicroConf Remote 4.0 are now on sale [2:55] Putting a tech twist on a regulated industry [3:27] Improving the onboarding experience [5:24] How Ashley came up with the name for her business, With Jack [8:24] How she used the money from her freelance photography business to fund the early development costs for With Jack [10:16] Lessons learned from taking over her father’s insurance business at 18 [15:20] The danger of depending on only one channel to run your business [17:49] Ashley’s three pivotal business moments [21:27] The concept of a vitamin vs. painkiller business [27:10] The challenges of hiring an executive or admin assistant in a highly regulated industry [28:42] How Ashley responded when a competitor stole her website design [31:17] Why you shouldn’t be intimidated if a competitor gets funding Links from the Show: Ashley Baxter @iamashley I Twitter With Jack I Company Website Ashley Baxter I Ashley’s website 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 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, location, or progress. Microsoft for Startups Founders Hub is a platform that provides founders with free resources to help solve startup challenges, including access to Azure credits, development tools like Github, mentorship resources, Microsoft collaboration and productivity software like Teams and Outlook and more. The program is open to all and takes 5 minutes to sign up, with no funding required. Learn more aka.ms/startupsfortherestofus Topics we cover: [0:59] The State of Independent SaaS Report & Livestream [5:38] Google is ending work from home options for most Bay Area employees [12:11] How much do startup founders pay themselves? [14:51] The impact on having cofounders and salaries [19:41] Why you are probably using email wrong [26:21] Rob’s system for filtering emails [30:45] Twitter is making it harder to choose the reverse chronological feed [37:37] Practical strategies for working with and getting money to your existing developers in Ukraine and Russia Links from the Show: Google mandates workers back to Silicon Valley, other offices from April 4 I Reuters What do startup founders pay themselves? I Sifted Twitter makes it harder to choose the old reverse-chronological feed I The Verge 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 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 10x their MRR. In this episode, we reflect on what they learned in the last year, how their thought process has evolved around deploying capital to grow the business, and what they are most excited about in 2022. Topics we cover: [3:33] How Gather is on track to 10x MRR [4:26] Shifting from solo designers and small design firms to catering to large firms [5:51] Moving upmarket [8:28] Why they shut down Gather consulting services [10:38] How they knew when they had product-market fit [12:57] How they bounced back after their developer accidentally crashed their entire app [20:11] Their thought process for deploying capital to grow the business [23:02] What they are most excited about in 2022 Links from the Show: Gather | Website Brian Elliott (@brianleeelliott) | Twitter Thanks for listening to another episode of TinySeed Tales. If you haven’t already, be sure to check out all of Season 2 of TinySeed Tales with Brian and Scottie and Season 1 of TinySeed Tales, where we follow the SaaS journey with Craig Hewitt of Castos. 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 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 Hub is a platform that provides founders with free resources to help solve startup challenges, including access to Azure credits, development tools like Github, mentorship resources, Microsoft collaboration and productivity software like Teams and Outlook and more. The program is open to all and takes 5 minutes to sign up, with no funding required. Learn more aka.ms/startupsfortherestofus Dynamite Jobs was born after seeing a need within their community, The Dynamite Circle, a community for location independent entrepreneurs. It’s a need that would be hard for most people to bootstrap because it is a two-sided marketplace, but Dan and Ian had an advantage with their existing business and audience, and were able to capitalize on it. In fact, after humble beginnings, the business has grown 10x in the last year. In this episode, we chat about how they are bootstrapping and growing a two-sided marketplace, along with a wide range of other topics. Topics we cover: [2:37] Why Dan and Ian both settled in Austin, Texas and the unexpected benefits that has had for their businesses [3:22] Why their digital nomad journey in the early days was born out of necessity [4:35] The events that led to the first DCBKK event in 2012 and the impact it had on their business [6:16] Embracing the chops index instead of the old school digital marketer “guru” model [8:21] The ideas that led Dan and Ian to start Dynamite Jobs in 2017 [14:46] The first key metric for Dynamite Jobs back in the early days [17:12] How deciding to hire a CTO was the catalyst that scaled Dynamite Jobs exponentially in late summer 2020 [20:34] The critical mistake they made that cost them months of development time [22:51] The concept of CEO bombing vs. diving deeper into the core features that matter [24:53] The 1000 day principle [28:14] Where Dynamite Jobs is in relation to the 1000 day principle [29:00] How they 10x’ed the revenue for Dynamite Jobs in 2021 [30:26] The value of hiring senior people who are better than you [35:59] Actionable tips for recruiting and hiring great people [38:44] The lowest cost, highest leverage hiring advantage for founders [41:21] The rip, pivot and jam framework [43:14] Why some of their “best ideas” turned out to be the biggest failures Links from the Show: Tropical MBA Dynamite Jobs Dan Andrews (@tropicalmba) | Twitter

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: iTunes | Spotify | Stitcher

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 Links from the show How to Deal with Rude Customers Cody Duval (@codee) | Twitter 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 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 Links from the show Keeping Cody Duvall (@codee) | Twitter 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 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 competitive market as a solo-founder [32:24] When to buy vs build internal tools Links from the show The Mom Test - a book by Rob Fitzpatrick Audience Podcast Bench Accounting | Online Bookkeeping and Tax Filing Services for Your Small Business Craig Hewitt (@thecraighewitt) | Twitter 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