Startups For the Rest of Us

Is perfectionism quietly sabotaging your career or startup dreams? In this episode, Rob Walling talks with his brother, Russ Walling, about the mindset and habits that shape long-term success from overcoming perfectionism to building resilience and learning to make tough calls without all the answers. They discuss how growing up with a shared emphasis on hard work, sports, and achievement created both strengths and struggles and how lessons learned in construction, poker, and entrepreneurship still apply to building great companies today. 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:  (04:10) – How early lessons in hard work and sports shaped mindset (07:46) – Learning to be comfortable being uncomfortable (12:03) – The dark side of perfectionism (16:51) – Overcoming fear of failure and learning to take risks (19:04) – What poker taught Russ about risk and decision-making (21:52) – The Armageddon Beer story  (28:53) – Why both brothers chose entrepreneurship (31:08) – Redefining leadership: collaboration over fear (35:24) – The three traits that drive lasting success (43:45) – Why hard work is still the ultimate differentiator Links from the Show:  Discretion Capital M&A Advisory for SaaS Founders doing $2-25M The SaaS Playbook by Rob Walling 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: iTunes | Spotify

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

Have you ever pushed so hard on an idea that you missed the signal to change direction? In this solo episode, Rob Walling covers a wide range of topics and dives into three areas every founder should master: how to develop an editorial eye (or “taste”), the difference between persistence and obstinance, and why focus, not diversification remains the hardest, most valuable entrepreneurial skill. 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:  (1:55) – How to develop an “editorial eye” (and why it matters for founders) (7:03) – When to get out of the way and let true experts lead (8:07) – Why your product must start with a real problem (not just an idea) (9:11) – Paul Graham’s The Right Kind of Stubborn: persistence vs. obstinance (12:03) – Are you attached to your goal or just your first idea? (13:44) – How great founders adapt to new data without losing momentum (14:44) – Sam Parr on why “constant switching will kill you” (16:30) – Focus as a founder’s hardest and most valuable skill (16:49) – Why “Triple, Triple, Double, Double” isn’t dead (despite VC takes) (18:34) – The problem with clickbait startup advice Links from the Show:  MicroConf Europe 2026 – Join us in Reykjavík, Iceland (Sept 21–23) - Promo Code: ROB50 The Mom Test by Rob Fitzpatrick Paul Graham: “The Right Kind of Stubborn” Sam Parr (@thesamparr) | X  Harry Stebbings (@HarryStebbings) | X Rob Walling YouTube Channel The SaaS Playbook 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: iTune...

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:

What’s it take for a bootstrapped SaaS to beat a competitor with $10M in venture funding? In this episode, Rob Walling talks with Laura Roeder, founder of Paperbell, about how her lean, fully-bootstrapped team outlasted and outperformed a VC-funded rival. They discuss what the venture-backed company got wrong, how Paperbell focused on the right customers, and why efficiency still beats funding. Topics we cover:  (3:52) – Competing against a $10M-funded startup (8:45) – Why “self-serve SaaS on hard mode” was worth it (14:36) – How over-investing in engineering killed their competitor (19:04) – The real problem with under-investing in marketing (21:19) – Why some SaaS markets can’t scale upmarket (24:13) – Why some markets are perfect for bootstrappers (28:42) – How big funding rounds create false signals (30:24) – The behind-the-scenes of a potential acquisition deal (33:26) – How Paperbell became the market leader Links from the Show:  MicroConf Mastermind Matching The SaaS Playbook by Rob Walling Paperbell Laura Roeder (@lkr) | 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