Startups For the Rest of Us

In Episode 570, Rob Walling answers listener questions about the ideal business for bootstrapping, how to create trust with potential customers, navigating depression as an entrepreneur as well as advice for introverted founders. The topics we cover [1:42] Problems that are more conducive to bootstrapping [8:51] Creating trust with potential customers [10:51] Battling depression or mental illness as an entrepreneur [13:45] Advice for introverted founders [18:95] Standard operating agreement for co-founders 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 569, Rob Walling chats with Anna Maste, a founder who's been a part of the MicroConf community for several years. They talk about how Anna bootstrapped a two-sided RV marketplace and eventually sold it for a healthy multiple. The topics we cover [1:16] An RV boondocker [2:53] Selling for a healthy multiple [5:21 ] Building a business with a a family member [7:02] Tech stack used [8:23] Launching and early customers [12:45] Experimenting with business models and pricing [14:01] Inflection in growth [18:21] Bootstrapping and fitting in [23:53] First purchase offer [28:05] Accepting the second strategic offer Links from the show Boondockers Welcome Anna Maste (@skulegirl) | 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 568, Rob Walling talks about MailChimp selling for $12 billion to Intuit, the largest exit for a bootstrap company, ever. Not that all founders aspire to grow to this scale, but it's truly an incredible day for bootstrapped founders to know that we have the potential to get to this level without raising institutional funding. The topics we cover [1:41] $800 million in ARR without outside funding [4:14] Acquisition multiple [7:42] Everyone sells, eventually [9:31] Respect for MailChimp [11:49] Disappointed with the UX [13:21] Equity vs higher salaries and bonuses [18:00] Long term outlook for existing Mailchimp customers [21:21] Never say you're never going to sell [21:42] Being an email service provider today is hard Links from the show Episode 519 | Profit Sharing, Stock Options, and Equity (A Rob Solo Adventure) Rob Walling (@robwalling) | Twitter If you have questions about starting or scaling a software business that you’d like for us to cover, please

In Episode 567, Rob Walling chats with Don Pottinger about joining a company as a developer, transitioning to CTO within 6 months, buying the company for $1, and then later on selling it for a life-changing sum of money. The topics we cover [1:13] Introductions [4:08] Learning to code independently vs learning on the job [06:38] Joining Kevy in 2014 [8:00] Transitioning to Director of Engineering and then to CTO [11:58] Difficulty of laying employees off [14:20] A new CEO and $0 MRR [16:08] Cap table difficulties [19:56] CEO departure and buying the company for $1 [26:30] Starting over and doing it solo [29:01] Running as a lifestyle business and selling the company [35:02] Launching a new startup Links from the show Kevy Langua Talk Don Pottinger (@donpottinger) | 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! Su

In Episode 566, Rob Walling chats with Hana Mohan about her journey as a SaaS founder. They compare and contrast bootstrapping and being venture-backed, hiring a chief of staff early on as a startup founder, and more. The topics we cover [2:17] Intro [3:36] Deciding not to bootstrap MagicBell [6:34] The team Composition at MagicBell [9:15] The marketing approaches that are working today. [10:47] Technology behind MagicBell [19:32] Bootstrapping vs raising funding [24:24] The importance of finding the right investors and hiring the right people [25:27] Hiring a Chief of Staff Links from the show Starting a new tech business as a transgender woman From Bootstrapped to Venture-Backed with Hana Mohan Hana Mohan (@unamashana) | 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 565, Rob Walling answers listener questions about focusing on one product vs multiple, sharing revenue metrics with early employees, and how to overcome the lack of motivation when starting new projects. The topics we cover [05:31] Focusing on one core product vs multiple separate products at the same time [14:59] Sharing revenue metrics with new employees [18:37] Struggling with motivation and consistency Links from the show Cargo cult 1 simple rule to figure out which advice you should follow Episode 559 | Bootstrapping a Two-Sided Marketplace with MicroAquire Rob Walling (@robwalling) | 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 564, Rob Walling chats with Sol Orwell about growing his website, examine.com to millions of views per month, changing revenue models, and the importance of doing customer interviews. The topics we cover [2:14] Intro [3:06] How Examine started [7:21] Examine's differentiated approach based on scientific research [9:33] 10,000 paying subscribers [10:59] Building trust through transparency [15:26] Interviewing customers [21:14] Getting hit by Google [26:52] Sol's stunt marketing pages Links from the show Our Mistakes | GiveWell Examine SJO.com Sol Orwell (@sol_orwell) | 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 563, Rob Walling answers listener questions about startup operating agreements for co-founders, common cloud hosting solutions, struggling as a young entrepreneur, and selling your startup when you have over $1M in annual recurring revenue. The topics we cover [1:40] Operating agreements for startup co-founders [5:50] How to do startup vesting when not working fulltime on a project [9:41] Common cloud hosting solutions for startups [11:04] Struggling as a young entrepreneur [18:20] Call to action for info product [20:54] Virtual assistance [23:05] Selling above $1M ARR Links from the show LegalZoom Rocket Laywer Upcounsel Start Small, Stay Small Upwork Best Jobs Virtual Staff Finder Rob Walling (@robwalling) | 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 | S

The application for TinySeed’s Fall 2021 SaaS accelerator batch of startups will open for two weeks starting on August 9th, 2021. Watch the video recording of the Fall 2021 Batch Info Session here: https://youtu.be/6dqTClonO2Y Interested in applying? Join us for an info session with the TinySeed team to talk about the application process, what to expect as a member of TinySeed, and some of the things we are looking for in companies we welcome into the fold. https://tinyseed.com #tinyseed We’ve written a few posts that might be helpful if you’re considering applying: — Our Fall 2021 application announcement: https://tinyseed.com/latest/tinyseeds-fall-2021-application-announcement — Preview our Fall 2021 application and requirements in this overview: https://tinyseed.com/latest/2021-application-preview — Curious about what it's like being a TinySeed founder? Part 1 - https://tinyseed.com/latest/whats-it-like-being-a-tinyseed-founder Part 2 - https://tinyseed.com/latest/part-2-tinyseed-founder

In Episode 562, join Rob Walling for another solo adventure to talk about enterprise sales, mental frameworks for founders, undoable decisions, and how to handle being approached about an acquisition. The topics we cover [2:33] Enterprise sales advice [5:48] Measure twice, cut once for SaaS [10:56] Holy Grail of SaaS: Expansion Revenue [13:12] Holy Grail of SaaS: Virality [14:25] Holy Grail of SaaS: Big space with slow-moving incumbents [15:46] Things to keep in mind when being approached about an acquisition Links from the show Josh Ledgard on Twitter Rob Walling (@robwalling) | 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 561, Rob Walling chats with Andy Cabasso, co-founder of Postaga, about launching on Product Hunt, having a done-for-you service in addition to a DIY self-service SaaS app, growing to a team of six people, having a free plan, and doing a ton of customer development in the early days. The topics we cover [01:35] Selling an agency with retainers to start Postaga [03:46] Explaining Postaga simply and succintly [06:32] Size and stage of Postaga [07:24] Using Postaga to market Postaga [10:22] Learning from early users [13:56] Launching on Product Hunt [18:09] Was it worth it to launch on Product Hunt? [20:30] Not charging at launch [22:22] Conjecturing on a Product Hunt flop [23:26] Postaga pricing plans [25:58] A big month of growth [32:13] A SaaS product with a service component Links from the show Postaga | Automated Post Promotion and Marketing Platform Andy Cabasso (@andycabasso) | Twitter If you have questions about starting or scaling a software

In Episode 560, Rob Walling is joined by Einar Vollset and Tracy Osborn to talk about deciding when it's time to hire someone, how to think about which role to hire next, changing location to force productivity, and more. The topics we cover [2:52] Deciding to hire a community manager [9:28] Location hacks for improved productivity [14:52] Delta airline pilot suing Delta for stealing app [20:35] Product → Business → Company [27:18] Facebook Users say "No" and Advertisers are Panicking [32:32] Tech-enabled modern banks Links from the show MicroConf Remote Community Manager Tracy Osborn's Tweet on Location Hacking Delta pilot sues the airline for allegedly stealing an app he designed | Engadget Rob Walling's Tweet on Product → Business → Company FacebookUsers Said No to Tracking. Now Advertisers are Panicking Square Business Banking | Checking, Savings, & Loans If you have questions about starting or scaling a software business that you’d like for us to cover,

In Episode 559, Rob Walling chats with Andrew Gazdecki, the founder of MicroAcquire, about bootstrapping a two-sided marketplace in a competitive industry. They talk about Andrew's previous successes, including growing Bizness Apps to $10 million in annual recurring revenue. They also unpack Andrew's current business, MicroAcquire, and talk about how it was started, its current success, and the future plans for the business. The topics we cover [6:03] Why did Andrew decide to sell Bizness [8:12] Background on MicroAcquire [10:52] Ideal revenue for MicroAcquire [13:29] Comparing MicroAcquire differs from similar broker websites [16:59] The future of MicroAcquire [20:50] Metrics since launching in January 2020 [23:08] Bootstrapping a two-sided marketplace [26:33] Raising $22 million post-money valuation [31:25] The hardest thing about bootstrapping a business Links from the show MicroAcquire Bizness Apps Andrew Gazdecki (@agazdecki) | Twitter If you have questions

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 questions

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 | Stitcher

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 & Review: 

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 & Review: iT

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