Startups For the Rest of Us

How does a founder actually learn the skill of product? In this episode, Rob Walling talks with Ruben Gamez of SignWell and Bidsketch to answer listener questions that turned into a much deeper conversation than expected. They cover why friction works well for one of Ruben's products and kills conversions on the other, how to think about trial length and onboarding when users need more time, and what it actually takes to develop product instincts as a bootstrapped founder. Want to get your question answered? Drop it here. Topics we cover: (4:00) – Friction in trial funnels: Bidsketch vs. SignWell (8:26) – When to test friction vs. trust your gut (10:44) – Testing with low volume (16:56) – Trial length for project management SaaS (18:47) – How do you learn product? (21:39) – How Ruben developed product sense on the job (23:21) – The two core product skills bootstrappers actually need (29:42) – Product management vs. UX (31:46) – Why product sense doesn't transfer between products (34:07) – How fast you can build product sense Links from the show: SaaS Institute Cancun Retreat – Dec 5-7, 2026, exclusively for 7 & 8 figure SaaS founders | Waitlist: tracy@tinyseed.com Sponsorship inquiries: sponsors@tinyseed.com TinySeed SaaS Institute Shreyas Doshi Product Sense Course Shreyas Doshi on YouTube Ep 15 - Strategy Session | The Offsite Podcast The Panel Podcast SignWell Bidsketch Ruben Gamez (@earthlingworks) | X 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

Could your business structure quietly cost you millions when you sell? In this solo episode, Rob Walling answers listener questions about when QSBS might justify a C Corp (vs. staying an S Corp or LLC), why SaaS exits are often discussed in ARR multiples rather than EBITDA, and how the profitability/growth tradeoff impacts valuation. He also shares thoughts on GMV-based pricing and where developers can learn practical, non-fluffy marketing skills. Episode Sponsors: This episode is brought to you by Mercury Mercury is the banking solution I use across my businesses, from my personal single-member LLC to MicroConf and TinySeed. Traditional banking forces you to duct-tape tools together and work around slow, clunky processes. Mercury gives me a clean dashboard that shows exactly where each business stands at a glance. The interface is simple enough for daily banking and paying invoices, but powerful enough to handle multi-step approval workflows for large transfers. There's a reason more than 300,000 entrepreneurs have made the switch. It's free to get started with no in-person visits and no minimum balance. Apply online in minutes at mercury.com. Mercury is a fintech company, not an FDIC-insured bank. Banking services provided through Choice Financial Group and Column N.A., Members FDIC. If you’ve got a strong vision but no technical partner, you need more than a “vibe-coded” MVP, you need a real foundation. That’s where Designli comes in. Their two-week SolutionLab Prototyping Sprint pairs you with a product owner, designer, and developer to turn your idea into a beautiful, clickable prototype you’ll be proud to show investors or early users. Right now, Startups for the Rest of Us listeners get $3,800 off their sprint. Get started at designli.co/fortherestofus Topics we cover: (3:30) – How the QSBS tax benefit can save you millions (7:40) – C Corp vs. S Corp: which structure makes sense for founders (9:39) – Why ARR multiples matter more than EBITDA in SaaS (13:13) – Profitability as a drain on growth (17:48) – Should co-founders join the same mastermind? (19:16) – How to leverage GMV-based pricing in SaaS (22:48) – The best way for developers to learn real marketing skills (31:28) – Why every founder should master sales and marketing early Links from the Show: TinySeed Applications Live Q&A - February 11th, 10:00 AM EST Apply to TinySeed - Applications are until Feb 17th, 2026 The SaaS Playbook by Rob Walling MicroConf - Community for SaaS Founders Conversion Factory TinySeed Mentors Rob Walling on X (@robwalling) 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:

How would a 2x unicorn founder build his next startup with AI? In this episode, Rob Walling sits down with Jason Cohen, founder of SmartBear and WP Engine, to talk about building billion-dollar businesses, the future of AI for founders, and what makes small companies thrive even when the odds are stacked against them. They dig into the early days of WP Engine, how Jason develops his frameworks, why execution beats ideas, and Jason’s framework for identifying “hidden multipliers” small, systematic changes that make an outsized impact. Episode Sponsor: Hiring engineers shouldn’t feel like sorting through AI-polished resumes. G2i cuts through all of that. They’ve pre-vetted over 8,000 engineers, all with 5+ years of real experience, and they run live, human-led technical interviews to verify actual skills. No time wasters. No guesswork. Just solid developers who can deliver. G2i is trusted by companies like Meta, Microsoft, and countless bootstrapped founders who need to move fast without making expensive mistakes. Get a 7-day free trial and $1,500 off when you mention Startups for the Rest of Us at https://www.g2i.co/rob Topics we cover: (03:45) – The core idea behind Hidden Multipliers (09:24) – Writing as a way of thinking (12:34) – Why sharing your frameworks matters (14:14) – The origin of “Designing the Ideal Bootstrap Business” (18:10) – The hidden weak links in every startup (21:25) – De-risking and niching down effectively (24:56) – Why narrowing your focus expands your reach (26:24) – Building WP Engine in a commodity market (29:37) – Out-executing funded competitors (31:52) – Finding product–market resonance through pricing (32:40) – How brand actually develops (37:54) – Building in the age of AI: pitfalls and opportunities (41:52) – The three categories of AI startups today (46:02) – Why 10x improvement is the new baseline for differentiation (49:19) – The real moat in the age of AI Links from the Show: MicroConf US 2026 – Portland, April 14–16, 2026 Promo Code: Rob50 for $50 off The SaaS Playbook PREORDER Hidden Multipliers by Jason Cohen Designing the Ideal Bootstrapped Business with Jason Cohen A Smart Bear Blog Jason Cohen (@asmartbear) | X 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

Can your 9-to-5 job secretly prepare you to be a founder? In this solo episode, Rob Walling shares 11 unexpected lessons from his own day jobs, from courier to electrician to engineering manager, and how each role quietly taught him skills that shaped his success as a SaaS founder. He dives into the value of curiosity, self-education, and learning to lead before you ever start a company. Episode Sponsor: If you’ve got a strong vision but no technical partner, you need more than a “vibe-coded” MVP, you need a real foundation. That’s where Designli comes in. Their two-week SolutionLab Prototyping Sprint pairs you with a product owner, designer, and developer to turn your idea into a beautiful, clickable prototype you’ll be proud to show investors or early users. Right now, Startups for the Rest of Us listeners get $3,800 off their sprint. Get started at designli.co/fortherestofus Topics we cover: (2:03) – Why every day job can teach entrepreneurial skills (4:44) – Lesson #1: Figuring things out when instructions are unclear (7:27) – Lesson #2: Learning to respect other people’s time (9:05) – Lesson #3: How early self-education compounds over time (11:33) – Lesson #4: Embracing hard, unglamorous work (14:09) – Lesson #5: Why experience always beats credentials (16:42) – Lesson #6: Letting the buck stop with you (17:44) – Lesson #7: Knowing when to cut corners (and when not to) (20:11) – Lesson #8: Finding the right people to work with (21:33) – Lesson #9: Managing and motivating people as a learned skill (23:53) – Lesson #10: Turning hiring and firing into Founder superpowers (26:11) – Lesson #11: The value of exposure to well-run systems Links from the Show: MicroConf Mastermind Matching – Apply before January 16th The SaaS Playbook by Rob Walling Good to Great by Jim Collins Seven Habits of Highly Effective People by Stephen R. Covey Think and Grow Rich by Napoleon Hill MicroConf Rob Walling @robwalling) | X 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:

How will AI, SEO, and market shifts change SaaS next year? In this solo episode, Rob Walling revisits his predictions for 2025, what he got right, what he totally missed and shares nine new predictions for 2026. He reflects on trends shaping bootstrapped SaaS, from the rise of AI-first startups to the challenges facing horizontal SaaS founders. Interested in Sponsoring this Podcast? If your product or service helps SaaS founders, bootstrappers, or indie entrepreneurs, you can reach thousands of listeners each week through Startups for the Rest of Us. Email us at sponsors@startupsfortherestofus.com Topics we cover: (1:09) – Lessons from common SaaS plateaus and the Core Four framework (4:39) – Rating his 2025 predictions: what came true (and what didn’t) (12:46) – Prediction #1: Horizontal SaaS will face major headwinds (15:56) – Prediction #2: Overreliance on SEO will hurt SaaS founders (16:26) – Prediction #3: Top brands will dominate as AI narrows discovery (21:04) – Prediction #4: The AI VC bubble won’t burst in 2026 (21:47) – Prediction #5: Open source AI models will double in usage (22:28) – Prediction #6: A major no code platform will struggle or shut down (23:33) – Prediction #7: M&A for small SaaS startups will accelerate (24:31) – Prediction #8: Bitcoin will hit a new all-time high (25:31) – Prediction #9: Stripe will not go public (again) (26:26) – Reflections on MicroConf and TinySeed milestones Links from the Show: MicroConf US – Portland, April 2026 Rob Walling YouTube Channel Apply to TinySeed TinySeed Portfolio The SaaS Playbook by Rob Walling 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