Startups For the Rest of Us

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:...

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 hirin...

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 b...

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 2...

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-...

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...

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...

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 de...

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 founde...

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 h...

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 in...

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 con...

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...

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 t...

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,...

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 launc...

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 acq...

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...

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 featu...

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...

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 c...

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 a...

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 Found...

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 digg...

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...