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:

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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: 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:

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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: iTunes | Spotify

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

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?

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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

After funding 210+ B2B SaaS companies, what patterns have emerged?

In this episode, Rob Walling shares the 2025 State of TinySeed, from its first fund in 2018 to a global portfolio of over 210 B2B SaaS companies. He reflects on TinySeed’s growth, what the data reveals about today’s founders, funding trends, and the rise of AI-first startups.

Topics we cover: 

• (1:46) – How TinySeed began and the doubts it faced 
• (3:51) – Growing to 210+ portfolio companies and $60M raised
• (11:15) – The rise of AI-first startups and “vibe-coded” apps
• (13:09) – Record application numbers and founder trends in 2025
• (19:58) – Why vertical SaaS is outperforming horizontal SaaS
• (21:59) – The importance of founder community and shared experience
• (25:06) – How TinySeed and MicroConf create long-term founder connections

Links from the Show: 

• Apply to TinySeed
• Invest in TinySeed
• TinySeed MentorsAccelerator Program Details — TinySeed
• TinySeed Portfolio
• The SaaS Playbook by Rob Walling
• MicroConf - Community for Bootstrapped SaaS 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

How do you step back from daily decisions without losing control of your SaaS?

In this episode, Rob Walling answers listener questions about when to delegate key founder skills, whether great founders can succeed with any idea, and the limits of no-code or “vibe-coded” apps. 

To help answer one question, he calls up Ruben Gamez to get his insights on what “good” freemium retention really looks like and why the shape of your retention curve matters more than the number itself.

Want to get your question answered? Drop it here.

Episode Sponsor:

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 Topics we cover: 

• (2:51) – What’s a “good” freemium retention rate?
• (4:59) – How freemium retention differs for mobile vs. SaaS apps
• (9:51) – When to start delegating the Core Four SaaS skills
• (12:53) – How to hand off sales, marketing, product, and dev the right way
• (23:28) – Can great founders succeed with any product idea?
• (29:34) – Should founders avoid building on no-code or third-party platforms?

Links from the Show: 

• MicroConf Connect 
• TinySeed SaaS Institute
• The SaaS Playbook
• SaaS Launchpad
• SignWell
• Ruben Gamez | LinkedIn

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 much design polish is really enough?

In this episode, Rob Walling is joined by fan favorite Derrick Reimer for a new round of listener questions. They dig into the best AI coding stacks right now, how to ship fast without losing polish, whether AI is changing the kind of risk founders face, and when to start taking security seriously.

Episode Sponsor:

Are you a non-technical founder with solid revenue and real traction, but your technology is holding you back? You should check out today's sponsor, Designli.

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And for listeners of the pod, Designli is offering their Impact Week completely free. That’s a one-week, no-obligation audit where their team dives into your code, your design system, and your product roadmap to show you exactly what’s working, what’s broken, and what needs to happen next.

If it’s a fit, you can move on to SolutionLab, a three-week sprint where Designli takes over your codebase and architects a real roadmap for growth, led by a full-time, cross-functional team.

If your tech is the bottleneck to your next stage of growth, check them out at https://designli.co/fortherestofus.

 Topics we cover: 

• (2:03) – What’s the best A.I. coding stack for developers right now?
• (11:14) – How can solo founders ship fast without sacrificing polish?
• (21:55) – Is A.I. shifting startup risk from market fit to feasibility?
• (31:44) – When should SaaS founders start worrying about security?
• (44:30) – SavvyCal’s latest product expansion

Links from the Show: 

• Call for Speakers – Apply to speak at MicroConf US in Portland
• Claude Code
• Windsurf
• Cursor
• GitHub Copilot
• VS Code
• Visual Studio
• SavvyCal Appointments
• Derrick Reimer | LinkedIn
• Derrick Reimer (@derrickreimer) | 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

What are the can't-miss AI tools for SaaS founders?

In this episode, Rob Walling sits down with Craig Hewitt, founder of Castos, to dive deep into Craig’s “100 Days of AI” YouTube series. They discuss the lessons learned from exploring the latest AI tools for founders, why ChatGPT might not be the best option for SaaS entrepreneurs, and which AI platforms are actually moving the needle. 

Rob and Craig also chat about the realities of AI agents, the challenges of building a second product after hitting a growth plateau, and Craig’s approach to evaluating new opportunities as he looks to expand beyond podcast hosting.

Episode Sponsor:

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No more cobbling together tools. Ahrefs brings it all into one powerful SaaS marketing platform, backed by 15+ years of real-world web data and marketing-savvy AI.

Try it free at ahrefs.com/awt.

Topics we cover: 

• (03:28) – 100 Days of AI YouTube series, biggest surprises and key takeaways
• (08:20) – Claude Code, ChatGPT, and Manus: Which AI tools work best for founders
• (13:00) – Practical AI workflows in content production and automation
• (18:35) – AI agent cuts customer support in half
• (21:27) – Burnout and breakthroughs from publishing 100 videos in 100 days
• (25:43) – Craig’s new AI projects and what’s next
• (30:14) – Three new product ideas under evaluation
• (33:09) – The pros, cons, and emotions behind launching a second product

Links from the Show: 

• MicroConf US 2026- April 12-14, 2026 · Portland US
• TinySeed’s SaaS Institute
• Claude Code (by Anthropic) 
• Manus 
• Creator Hooks
• Cursor
• HelpScout
• DocsBot
• LinkBerry.ai – Craig’s new tool for LinkedIn content creation
• Castos
• Craig Hewitt | YouTube
• Craig Hewitt | LinkedIn
• Craig Hewitt (@TheCraigHewitt) | 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

Is it time to sell, autopilot, or double down on your plateaued SaaS business?

In this episode, Rob Walling tackles listener questions and shares practical frameworks for what to do when your product hits a plateau, explains why “autopilot” often leads to decline, and outlines when founders should seriously consider SOC 2 compliance. Rob also talks about balancing a startup with a newborn, the real value of open source and IP, and the risks and rewards of building MVPs in exchange for equity.

Want to get your question answered? Drop it here.

Episode Sponsor:

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Topics we cover: 

• (2:34) – What to do with a plateaued $500k B2C app
• (4:28) – Founder motivation, business longevity, and the myth of autopilot
• (13:15) – Should you offer MVP development in exchange for equity?
• (14:04) – Equity risks, upside, and how to protect yourself
• (18:00) – When SOC2 compliance actually matters for founders
• (21:08) – Balancing a new baby, a job, and SaaS ambitions
• (24:38) – Can open source IP help bootstrappers stand out?
• (25:25) – Why differentiation and marketing matter more than patents or code

Links from the Show: 

• Discretion Capital – M&A Advisory for B2B SaaS with $2-25m ARR
• MicroConf Connect
• TinySeed SaaS Institute

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