Startups For the Rest of Us

In Episode 558, Rob Walling chats with Einar Vollset about bootstrapping versus funding and the many options that exist in between. No longer is it a decision between a bootstrapped or venture path. With their unique perspectives, Rob and Einar talk about all of the funding options that exist. They also share some things to consider when deciding whether or not to take on funding and, if you do, how much you should plan on raising. The topics we cover [04:24] When funding makes sense for bootstrappers [11:54] Raising pre-revenue vs raising with revenue [15:29] Risks of raising as a platform (e.g. Shopify) business [20:40] Funding options available to bootstrappers [27:57] Convertible notes & SAFE's [29:16] How much should a bootstrapper raise? Links from the show Episode 496 | "The Press Covers Exceptions, Don't Compare Yourself to Slack or Zoom" Episode 411 | Bootstrapping vs. Funding: 19 Questions To Ask Einar Vollset (@einarvollset) | Twitter If you have quest

In Episode 557, Rob Walling flies solo to talk about investing for founders, with an emphasis on retirement. Rob views investing as a long-term game, not treating the stock market like a slot machine by buying and selling stocks. As founders, we're busy with our work, our family, and our friends. We don't want to spend a ton of time fiddling with investments. In this episode, Rob outlines an 80/20 approach to getting the most out of investing as a founder. The topics we cover [02:13] How Rob made most of his money [04:07] The rule of 72 [07:30] Investing on autopilot while building startups [07:46] Build an emergency fund [09:53] Max out retirement plans [12:08] Open a simple IRA or SEP IRA [13:00] Life insurance [14:35] Retirement account asset allocation [18:32] Taking your investments to the next step Links from the show Rule of 72 Haven Life Lazy Portfolio Money For the Rest of Us The Stacking Benjamins Podcast Afford Anything If you have questions a

In Episode 556, Rob Walling chats with Adam McCrea about growing from zero to $300,000 in ARR over the course of three years as a Heroku add-on. Adam is still a single founder with no employees and up until joining the TinySeed accelerator in their Spring 2021 batch, has fully bootstrapped Rails Autoscale. Now, he's working to grow the app, deal with platform risk, and launch pricing experiments. The topics we cover [03:30] Background before starting Rails Autoscale [07:04] Getting to 100 active users [09:30] Platform risk [14:59] Working on Rails Autoscale as a side project [20:54] Rails Autoscale vs. Heroku's Autoscaler [24:13] Free-trial to freemium experiment Links from the show Rails Autoscale Adam McCrea (@adamlogic) | 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 | Sti

In Episode 555, Rob Walling answers listener questions with Ruben Gamez. They discuss different models of bootstrapping success, hiring W2 versus hiring contractors, determining if a business is an ideal fit for bootstrapping and they revisit enterprise pricing. The topics we cover [01:24] Bootstrappers Rob & Ruben admire [12:25] Pros and cons to hiring contractors vs W2 employees [23:05] Determining if an idea is a good fit for bootstrapping [28:31] How to develop competitive pricing for large enterprise clients Links from the show Moraware CartHook Balsamiq Churn Buster SparkToro Bidsketch Episode 551 | Task-level vs. Project-level Thinkers, No Such Thing as an Autopilot Business, and More (A Rob Solo Adventure) Ruben Gamez (@earthlingworks) | 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 554, Rob Walling chats with Sherry Walling about grief as a part of entrepreneurship and how to get better at handling grief as an entrepreneur. They also discuss burnout and properly evaluating if it's the right time to sell a company. The topics we cover [02:18] Grief is part of entrepreneurship [05:12] Getting better at handling grief and loss [06:07] Grief and selling a company [09:01] The importance of symbols [12:04] Evaluating reasons to sell a company [16:37] The three components of burnout [20:21] Changing your work schedule for summer Links from the show The Entrepreneur’s Guide to Keeping Your Sh*t Together: How to Run Your Business Without Letting it Run You 18 Summers ZenFounder Sherry Walling Sherry Walling (@zenfounder) | 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 553, Rob Walling chats with Tracy Osborn about the latest bootstrapper news, including the recent Stack Overflow and Moz acquisitions, quitting instead of giving up remote work, and highlights from TinySeed 2020 Batch. The topics we cover [01:52] Intro [03:45] Stack Overflow acquisition [12:11] Moz acquisition [16:33] Quitting instead of giving up remote work [26:44] Highlights from TinySeed 2020 Links from the show Episode 545 | The Value of Learning 80/20 Design Fundamentals Episode 511 | Raising Prices & Re-writing Your Codebase Employees Are Quitting Instead of Giving Up Working From Home Stack Overflow Sold to Tech Giant Prosus for $1.8 Billion Tracy Osborn (@tracymakes) | 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 552, Rob Walling is joined by co-host emeritus, Mike Taber to chat about his decision-making around whether to launch a freemium plan, whether to do an AppSumo deal, how his potential partnerships merger is panning out. The topics we cover [04:93] Update on the CRM partnership opportunity, AppSumo, and Freemium [23:39] Yet another Google security audit update Links from the show Bluetick.io Episode 535 | A Bluetick Update with Mike Taber MicroConf Remote Episode 543 | All Things Startup with #Mike Taber Mike Taber (@singlefounder) | 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 551 of Startups For the Rest of Us, Rob does another solo adventure to talk about hiring owner-level thinkers, the fallacy of an autopilot passive income software business, and more. The topics we cover [1:25] Hiring task-level thinkers, project-level thinkers, and owner-level thinkers [07:43] The fallacy of an autopilot passive income software business [15:21] Our bootstrap community [20:45] Questions you should ask yourself when building/growing a company Links from the show FE International: Professional M&A Advisor Quiet Light Brokerage MicroAcquire - Startup acquisition marketplace. Free. Private. No middlemen. Empire Flippers - Website Brokers Billion Dollar Loser: The Epic Rise and Spectacular Fall of Adam Neumann and WeWork Invent and Wander: The Collected Writings of Jeff Bezos, With an Introduction by Walter Isaacson If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your ques

In Episode 550, Rob Walling chats with Tony Chan, co-founder of CloudForecast, about his incredible story of perseverance after getting rejected multiple times only to finally find product-market fit and reach six figures in annual recurring revenue. The topics we cover [04:11] CloudForecast's current revenue and customer base [08:43] Origin story for the idea of CloudForecast [16:53] Dealing with (many) rejections [28:01] Parting ways with a co-founder [30:07] The journey to Product-Market Fit [35:23] Marketing channels that are working for CloudForecast Links from the show CloudForecast Episode 464 | Highs, Lows, and Building Your First Sales Process with Steli Efti Episode 507 | Making Cold Email Work in B2B SaaS Episode 463 | Troubleshooting Enterprise Sales (A Founder Hotseat with David Heller) The Only Sales Guide You'll Ever Need by Anthony Iannarino Tony Chan (@toeknee123) | Twitter If you have questions about starting or scaling a software business that you’d like for us to cover,

In Episode 439, Rob Walling is joined by Jordan Gal to answer listener questions about starting an e-commerce SaaS and the laws and regulations, and compliance requirements required. They talk about managing enterprise perceptions of risk towards bootstrap startups. They also answer questions about bootstrapping and enterprise SaaS as well as hiring a growth role and whether you should hire full-time or outsource to a contractor or an agency. The topics we cover [01:11] Regulatory requirements for starting an e-commerce platform (Solman Ahmed) [06:18] Managing enterprise perception of risk when selling as a bootstrapper (Noah Stall) [16:26] Are some markets not feasible with a bootstrapped approach? (Declan Sweeney) [22:42] Finding someone who is experienced growing SaaS companies (Russ) [30:10] Hiring full-time versus outsourcing (Filip Kis) Links from the show Crossing the Chasm DemandMaven || Growth Marketing Consultancy for SaaS & Startups MicroConf Connect — MicroConf

In Episode 548, Rob Walling chats with Zack Naylor about Aurelius and the harrowing tale of launching multiple times and having to rewrite and re-platform the codebase before finally finding success. They also discuss how to interpret feedback from your customers and the importance of listening to your instinct as a founder. The topics we cover [03:24] Background on how Aurelius helps UX researchers [07:56] The struggles of building and launching multiple alpha versions [15:14] Bootstrapping during a pandemic [22:20] Taking risks as an entrepreneur [26:28] Building a third version of the product that lead to unprecedented growth [30:48] Using your gut as a founder Links from the show Aurelius Things You Should Never Do, Part I Episode 541 | Faster Horses & Product Myths, Life-changing Money, Dual Funnels, and More Zack Naylor (@zacknaylor) | Twitter If you have questions about starting or scaling a software business that you’d like for us to cover, please 

In Episode 547, Rob Walling chats with Craig Hewitt about private podcasting, Apple's announcement around their subscription podcast offering as well as the accelerating growth of Castos. The topics we cover [1:22] Focusing on private podcasting at Castos [15:50] Mobile app for private podcasting [20:21] Apple's big announcement [28:08] Castos MRR growth Links from the show TinySeed Tales - Season 1 Seeking Scale Trustshoring Craig Hewitt (@thecraighewitt) | Twitter If you enjoyed this episode, let us know by clicking the link and sharing what you learned. Click here to share your number one takeaway from the episode. 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 546, Rob Walling flies solo for a Q&A episode. With a backlog of great listener questions, Rob discusses qualified small business stock (QSBS), hiring entrepreneurially-minded employees, indie hacking while working at a large company, and more. The topics we cover [01:51] Should I switch to a C Corp to take advantage of QSBS in five years? [05:40] How to attract entrepreneurial employees [14:19] Indie-hacking while working at a large Fortune 20 company [19:12] Finding a niche using the Disruptive Innovation Links from the show Episode 442 | Corporate Structures and How the Choice You Make Now Can Impact You Years Down the Line Episode 519 | Profit Sharing, Stock Options, and Equity (A Rob Solo Adventure) The Stair Step Approach to Bootstrapping | Rob Walling - Serial Entrepreneur Qualified Small Business Stock (QSBS) If you enjoyed this episode, let us know by clicking the link and sharing what you learned. Click here to share your number one takeaway from

In Episode 545, Rob Walling chats with Tracy Osborn about the importance of learning design fundamentals for startup founders. They also discuss her new book and the pros/cons of self-publishing vs working with a publisher. The topics we cover [00:52] Intros [02:00] Deciding to self publish vs going with a publisher [11:11] Design fundamentals for a startup founder [16:23] Training your design eye [18:57] The #1 thing to do to become a better designer [20:01] Prototypes: the process of sketching ideas Links from the show Hello Web Design No Starch Press The 90-Minute Guide to Building Marketing Funnels That Convert (Data Beats Opinion) Hello Web App Sounds True Tracy's Savy Call breakdown Balsamiq Sketch UX Pin Tailwinds Tracy Osborn (@tracymakes) | Twitter If you enjoyed this episode, let us know by clicking the link and sharing what you learned. Click here to share your number one takeaway from the episode. If you have questions about

In this episode, Rob Walling is joined by Josh Pigford to answer listener questions, covering topics like annual pay increases, B2B SaaS price increases, white-label vs branded product, and hiring startup-minded people. The topics we cover [03:04] Building Maybe, and Rob busts Josh's chops about starting a business so soon [10:02] Question #1: Annual Raises - Anonymous [18:24] Question #2: Explaining a Price Increase - Steve McLeod Bootstrap FM [23:11] Question #3: Free or Discounted Plans in Exchange for Branding - Adam Wohlberg [29:28] Question #4: Finding startup people to hire - Anonymous Links from the show maybe Transparent Salaries | Buffer Radford | Compensation Surveys Episode 537 | On Launching, Funding, and Growth with Serial SaaS Founder Rand Fishkin Parachute List We Work Remotely Authentic Jobs Dynamite Jobs Josh Pigford (@Shpigford) | Twitter If you enjoyed this episode, let us know by clicking the link and sharing what you learned. C

In Episode 543 of Startups For the Rest of Us, Rob is joined again by co-host emeritus, Mike Taber as he gives an update on all things startups and they analyze top tactics for superhero success. If you enjoyed this episode, let us know by clicking the link and sharing what you learned. Click here to share your number one takeaway from the episode. 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 542, Rob Walling chats with Zach Moreno, the Co-Founder and CEO of Squadcast about how they grew their revenue and surpassed $3 million in ARR as a mostly bootstrapped startup. They also discuss the role and importance of having a co-founder, as well as the impact that having a "knowledge investor" had on their success. The topics we cover [04:18] Squadcast growth while entering into a crowded space [16:54] The importance of having a co-founder [22:43] The shelter in place inflection point and building out video functionality [34:08] Choosing a knowledge investor Links from the show Squadcast Zencastr SavvyCal Why we believe something: The quality of audio matters Rockwell Felder - Twitter Zachariah Moreno (@zach__moreno) | Twitter If you enjoyed this episode, let us know by clicking the link and sharing what you learned. Click here to share your number one takeaway from the episode. If you have questions about starting or scaling a software busin

In episode 541, Rob Walling flies solo to discuss things like product myths and the misinterpreted Henry Ford quote, selling a company, defining life-changing money, and dual funnels. The topics we cover [02:48] Product myths and the misinterpreted Henry Ford quote [07:21] Post-exit thoughts [15:32] Life-changing money [22:30] The power of dual-funnels Links from the show Becoming Steve Jobs: The Evolution of a Reckless Upstart into a Visionary Leader Rob Walling - Mailing List Episode 510 | The Story of Startups.com If you enjoyed this episode, let us know by clicking the link and sharing what you learned. Click here to share your number one takeaway from the episode. 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, Rob talks with Tracy Osborn and Einar Vollset, about the recent news that's come out in the bootstrapper community. They talk about the Indie.vc shutdown, the new features coming out on Twitter, LinkedIn’s new gig marketplace, and more. The topics we cover [03:18] Twitter Spaces [10:05] The Network Effect and Twitter Verification [14:32] The Indie.vc shutdown [24:20] Shopify removing the option to work directly with Stripe [32:34] The new ‘Super Follow’ feature in Twitter [35:43] Comparing Google Cloud and AWS onboarding [40:04] The new LinkedIn Gig Marketplace Links from the show TinySeed Tinyseed Thesis Remail Voxer Shopify says remove Stripe billing or get booted from their app store Substack Indie.vc Google Cloud vs AWS onboarding If you enjoyed this episode, let us know by clicking the link and sharing what you learned. Click here to share your number one takeaway from the episode. If you have questions about st