Startups For the Rest of Us

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

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 epi

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? 

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 a

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

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/startupsforthere

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

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 f

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

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 ecosyst

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

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 Re

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

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 i

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 &

In Episode 589, Rob Walling chats with Jason Buckingham about how he found a startup idea from making more than 70 cold calls. It's a great story about staying focused, putting in the time and doing the hard work. The topics we cover [7:14] Finding a problem via cold calls [13:07] Identifying a problem and deciding what to do next [22:32] Getting spouses on board with entrepreneur journey [25:06] Working day jobs while building the product [30:09] Getting into Tiny Seed right before COVID-19 Links from the show Episode 45: Onboarding Your Spouse | Zen Founder Senior Place - Senior Placement and Referral Agency Software 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