Startups For the Rest of Us

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...

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  Micr...

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 l...

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 in...

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, plea...

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 cus...

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...

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...

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]...

In Episode 588, Rob Walling chats with Courtland Allen about a wide range of bootstrapper and indie hacker topics including the struggles with motivation/depression, bootstrapping today, fighting the urge to quit, and frameworks for getting your first dollar. The topics we cover [3:43] Hiring a podcast producer [6:21] Letting go in business [7:09] Invite-only experiment on Indie Hackers [16:03] Th...

In Episode 587, join Rob Walling as he answers listener emails including feedback and a critique about the podcast, the state of microentrepreneurship, and where to start with user growth. The topics we cover [2:22] The reason Rob continues to podcast [5:26] Renaming a company or podcast [8:40] Revisiting inflation [15:06] The state of microentrepreneurship [20:00] Where to start with user growth...

In Episode 586, Rob Walling chats with Michele Hansen about her new book where she talks about how to master customer interviews as a startup founder. The topics we cover [5:00] User experience research for startup founders [11:20] Customer Interviews for developers [12:30] Feature requests as customer research springboard [19:55] Practicing customer interviews [23:37] Comparing to Jobs to Be Done...

In Episode 585, Rob Walling chats with Sherry Walling about moving outside your comfort zone, the power of relationships, psychedelic-assisted therapy, as well as her new book about grief launching later this year. The topics we cover [3:22] Deciding against self-publishing [12:00 ] Building an audience vs. a network [14:26] Psychedelic-assisted therapy [24:00] The power and importance of relation...

In Episode 584, Join Rob Walling for a Happy New Year edition of the show where looks ahead to 2022 and evaluates what he wants to focus on. The things we choose not to do are just as important as the things we chose to do and Rob encourages you to think hard about what is and is not working for you today. The topics we cover [3:00] Founder's retreat [4:36] Estimating growth [9:23] Hiring a full-t...

In Episode 583, Rob Walling chats with Sam Parr about about building an email list, selling to Hubspot, podcast growth, and how to spot business opportunities. The topics we cover [3:53] Building Hustle to 8 figures in revenue [5:52] Growing an email list [11:01] Selling to a B2B SaaS [19:00] My First Million and growing podcasts [23:45] TikTok marketing [27:30] Spotting interesting opportunities...

In Episode 582, Rob Walling is joined by Einar Vollset to answer listener questions about enterprise sales, crowdfunding, replacing yourself, and things that every B2B SaaS founder should know. The topics we cover [1:26] Investing with Reg CF [6:20] Enterprise plans and pricing [13:31] Finding your replacement [19:29] Best way to give software demos [21:55] What fundamental things should startup f...

In Episode 581, Rob Walling discusses how to grow money sensibly while protecting the principle during inflationary times. He explores real estate, collectibles, crypto, stocks, bonds, and other strategies to consider as inflation and other economic changes occur. The topics we cover [2:00] Inflation is here [7:20] Pricing flexibility with SaaS [9:44] Rules when inflation goes up [13:53] Inflation...

In Episode 580, Rob Walling chats with Ross Hudgins, an SEO expert, about seven common things that SaaS founders either do well or frequently get wrong. The topics we cover [4:42] Put your blog in a subfolder, not a subdomain. [7:18] With keyword-focused content, make the URL exactly the main keyword. [10:10] Be thoughtful about feature page keywords [13:39] It’s really hard to rank for “best X so...

In this special episode of Startups For the Rest of Us, Rob Walling chats with Einar Vollset about not only the announcement of the TinySeed Syndicate but also the investment landscape for B2B SaaS today. Even if you don't think you'll raise funding, it's important to understand the dynamics of the investment and acquisition market as a bootstrapped founder. The topics we cover [1:40] Investment l...

In Episode 578, Rob Walling is joined again by co-host emeritus, Mike Taber for an update on his progress with Bluetick. Today we find out how Mike's merger that he has been working on for the past year has panned out. The topics we cover [3:55] Mike reflects on time and effort working on partnership [7:20] What to do when a deal stalls [9:00] Doubling down on Bluetick [14:50] Differentiating Blue...

In Episode 577, Rob Walling chats with Jim Kalbach about how to uncover the right problem to solve with the Jobs to Be Done (JTBD) framework. If you haven't been exposed to JTBD, this episode will be a great primer as we dive into practical examples for bootstrapped or mostly-bootstrapped founders. The topics we cover [3:00] Defining Jobs to Be Done (JTBD) [6:45] JTBD are stable over time [10:27]...

In Episode 576, Rob Walling chats about permissionless entrepreneurship, why you probably shouldn't be a media company if you're an early stage or bootstrapped SaaS, and the importance of exploring beyond what your customers ask for to find out what they actually need. The topics we cover [2:01] Permissionless entrepreneur [9:25] All startups should not become media companies [15:10] Find out what...

In Episode 575, Rob Walling is joined by Derrick Reimer for a quick update on SavvyCal and some recent hiring decisions he has made. They also answer listener questions about shipping code as a bootstrapper, pivoting, selling a business through a broker, and more The topics we cover [2:23] The latest with SavvyCal [12:02] Shipping code as a bootstrapper vs larger team [21:39] Considering a zoom-in...

TinySeed, MicroConf's venture fund and SaaS accelerator, is launching their Fall 2021 accelerator batch this week.

In Episode 574, Rob Walling chats with Andrew Fiebert, a founder who just couldn't get away from software. He's a software developer, turned podcaster, turned marketer, and now he's a software entrepreneur and on this episode, they discuss his success and struggles while building Lasso. The topics we cover [2:40] Introductions [4:15] WordPress plugin with an annual subscription [5:51] Starting a p...