Startups For the Rest of Us

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 bu

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 No

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 b

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&nb

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 Saa

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

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

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 Ti

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 an

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 week

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

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 soft

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] H

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 questio

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

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 chal

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, pl