
Advertise on podcast: Startups For the Rest of Us
Rating
4.9from
This podcast has
329 episodes
Language
EnglishPublisher
Rob WallingExplicit
No
Date created
2010/04/09
Latest episode
2026/04/21
Average duration
41 min.
Release period
8 days
Description
The original podcast for bootstrapped and mostly bootstrapped startups, this show follow the stories of founders as they start, acquire, and grow SaaS companies. Hear when they fail, struggle, succeed, and take you with them through the tumultuous life of a SaaS founder. If you like Mixergy, This Week in Startups, or SaaStr, you’ll enjoy Startup for the Rest of Us.
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Episode 829 | AI is Bad at Product, Top 5 Startup Success Factors, and the Beastie Boys (A Rob Solo Adventure)
2026/04/21
Can AI really handle product decisions for your SaaS?
In this solo adventure, Rob Walling revisits the core four SaaS skills and breaks down what AI can and cannot do across Development, Sales, Marketing, and Product. He also reframes Bill Gross's top five startup success factors for bootstrappers, walks through a hilariously bad UX decision by a local parking app, and closes with a surprisingly insightful Beastie Boys anecdote about shipping creative work into the world.
Episode Sponsor:
This episode is brought to you by Mercury
Mercury is the banking solution I use across all of my businesses, from my personal single-member LLC to MicroConf and TinySeed.
Traditional banking is broken, slow wires, clunky interfaces, tools that feel like they were built in 2005.
Mercury is what banking should feel like in 2026. Everything just works.
Whether it's daily bill pay or wiring large sums to the dozens of companies we invest in each year, Mercury handles it. Simple when I need simple, robust when I need approvals and controls.
Over 300,000 entrepreneurs have made the switch. When founders ask me where to set up their account, I send them to mercury.com.
Free to get started, no in-person visits, no minimum balance.
Mercury is a fintech company, not an FDIC-insured bank. Banking services provided through Choice Financial Group and Column N.A., Members FDIC.
Topics we cover:
(5:48) – AI and the Core Four SaaS skills
(7:03) – Why AI falls short with sales and marketing
(8:45) – The editorial eye AI still lacks
(10:14) – Why AI is worst at product
(13:41) – Bill Gross's top five startup success factors
(19:48) – A parking app's terrible UX decisions
(24:24) – The Beastie Boys and lessons on shipping
Links from the show:
TinySeed | SaaS Institute
Ep. 817 | Bootstrapping in the Age of AI with Jason Cohen
Rob Walling YouTube
Rob Walling Newsletter
Bill Gross’s Ted Talk on Startup Success Factors
The Beastie Boys on Conan O’Brian’s Podcast
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
Episode 828 | Am I Building a SaaS?, Serving Both B2C and B2B, Pricing, and More Listener Questions (Rob Solo)
2026/04/14
Is your product actually a SaaS?
In this episode, Rob Walling tackles listener questions about what really qualifies as SaaS (and where he disagrees with ChatGPT), how to serve both solopreneurs and enterprise customers with a dual funnel strategy, layering a B2B offering on top of a B2C product, pricing a mission-driven app without gatekeeping access, and the impact of healthcare costs on startup runway.
Want to get your question answered? Drop it here.
Episode Sponsor:
Your payroll tool doesn't talk to your bank. Your bank doesn't talk to your bookkeeper. And you're the one stuck in the middle playing admin instead of building your company.
Every is the back office platform built for startups. Incorporation, banking, international and domestic payroll, bookkeeping, and tax prep, one login, one platform. You get a dedicated Slack channel with actual humans, up to $3 million in FDIC insurance, corporate cards, and automated accounting.
Setup takes under 30 minutes. Most founders are fully transitioned within a week.
Check them out at every.io.
And if you're at MicroConf in Portland, make sure to swing by and chat with the team.
Topics we cover:
(3:09) – What qualifies as a SaaS business?
(5:15) – Why Netflix and Spotify are not SaaS
(8:11) – Where Rob disagrees with ChatGPT on SaaS
(12:21) – Serving solopreneurs and enterprise simultaneously
(15:13) – The power of the dual funnel strategy
(17:02) – Navigating the enterprise sales process
(22:20) – Layering B2B features onto a B2C product
(28:52) – Pricing a mission-driven job search app
(35:57) – Healthcare costs and startup runway in the US
Links from the show:
MicroConf Masterminds – Applications close April 17th
MicroConf’s Masterminds Guide
Newscatcher
HelpSpot
TinySeed
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
Listen to Episode 828
Episode 827 | The Founder's Guide to Selling Your SaaS for What It's Actually Worth
2026/04/07
What would it mean for you to leave 60 or 70% of your company's value on the table when you sell?
In this episode, Rob sits down with Einar Vollset, co-founder of TinySeed and founder of Discretion Capital, to talk about his new book, The Definitive Guide to M&A for B2B SaaS between $2 and $20 million ARR. They dig into why private equity now dominates the buyer landscape, why growth and churn are the top two valuation drivers, and how the myth that "startups are bought, not sold" could cost you millions.
Einar also explains the danger of running your business past its peak growth rate before selling, why ARR multiples matter more than profit, and how the right M&A advisor can add 30 to 300% to an initial offer.
Episode Sponsors:
This episode is brought to you by Mercury
Mercury is the banking solution I use across all of my businesses, from my personal single-member LLC to MicroConf and TinySeed.
Traditional banking is broken, slow wires, clunky interfaces, tools that feel like they were built in 2005.
Mercury is what banking should feel like in 2026. Everything just works.
Whether it's daily bill pay or wiring large sums to the dozens of companies we invest in each year, Mercury handles it. Simple when I need simple, robust when I need approvals and controls.
Over 300,000 entrepreneurs have made the switch. When founders ask me where to set up their account, I send them to mercury.com.
Free to get started, no in-person visits, no minimum balance.
Mercury is a fintech company, not an FDIC-insured bank. Banking services provided through Choice Financial Group and Column N.A., Members FDIC.
Everyone's talking about AI in marketing. But AI without strategy just means generating more bad marketing, faster.
The founders who win aren't the ones using the most tools, they're the ones with a real system behind their growth. Positioning, persuasion, conversion. That's what moves the needle.
That's what Conversion Factory does. They're a SaaS marketing and design agency that has worked with over 100 startups, including several TinySeed companies.
Book a call at https://conversionfactory.co/ and mention this podcast for $1,000 off your first month. And if you're at MicroConf US in Portland, grab Corey Haines in the hallway track to see how they can help you.
Topics we cover:
(3:34) – Why Einar wrote an M&A guide for SaaS founders
(5:26) – How founders leave value on the table when selling
(8:22) – How private equity moved down market
(11:24) – Choosing the right broker or banker
(12:55) – Platform acquisitions vs. tuck-ins explained
(19:24) – Why "startups are bought, not sold" is wrong
(25:48) – Growth and churn as top valuation drivers
(30:02) – Why ARR multiples matter more than profit
(34:34) – The danger of running past peak growth
Links from the show:
The Definitive Guide to M&A for B2B SaaS between $2–20M ARR
Discretion Capital
MicroConf US (Portland) - April 12-14, 2026
MicroConf Mastermind Matching
MicroConf Mastermind Playbook
TinySeed
Exit Strategy...
Episode 826 | How to Find, Hire, and Work with Owner-Level Thinkers
2026/03/31
How do you find someone who thinks like an owner, not just a task-doer?
In this episode, Rob digs into a batch of listener questions about task level, project level, and owner level thinkers. He covers how to identify them, what they cost, where to find them, and why building a team of exceptional people creates a virtuous cycle that lifts everyone up.
Topics we cover:
(4:13) – Defining task, project, and owner level thinkers
(7:32) – Are owner level thinkers born or built?
(10:16) – Compensation ranges for owner level thinkers
(11:53) – W2 vs. contractor for senior hires
(15:53) – Do you actually need owner level thinkers?
(17:36) – Where to find project and owner level thinkers
(20:16) – How long to integrate them into your company
(24:40) – How to identify them in job interviews
(29:38) – Why you won't always get hires right
Links from the show:
Rob Walling's Essays
Rob Walling’s Newsletter
Rob Walling YouTube
The SaaS Playbook
Remote First Recruiting
MicroConf
TinySeed
SaaS Institute
Discretion Capital
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
Episode 825 | Talking Tailwind CSS and Founder Fitness (with Adam Wathan)
2026/03/24
What happens when AI starts competing with your open source business?
In this episode, Rob Walling sits down with Adam Wathan, co-founder of Tailwind CSS, for a candid conversation about the dramatic revenue decline that forced Tailwind Labs to lay off most of their team. Adam shares the hard lessons learned from running a business based on one-time purchases, why he didn't see the slowdown coming, and how an honest podcast episode accidentally turned everything around.
Then they switch gears entirely to talk about founder fitness: how Adam lost 70 pounds, his 15-minute weighted vest workouts, and why tracking strength gains can be more motivating than watching the scale.
Episode Sponsor:
Hiring engineers right now is kinda broken. AI resumes, fake profiles, people who look senior on paper but can't ship anything real.
G2i cuts through all of that. They've pre-vetted over 8,000 engineers- not "we glanced at their GitHub" vetted, actually tested with live technical interviews. Contract or full-time- just tell them what you need and within days you're reviewing real candidates.
And you get a risk-free trial. If it's not a fit, they'll replace the dev in 24 hours.
G2i is trusted by companies like Meta, 1Password, 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
️ Want to attend their AI Miami in April? Use promo code use Rob50Off
Topics we cover:
(4:43) – Adam's history with Tailwind CSS
(5:17) – Revenue decline and the "boiling frog" problem
(8:30) – Making the hard decision to lay off the team
(11:39) – The viral podcast episode and unexpected sponsors
(13:07) – Should Tailwind have used recurring revenue?
(21:20) – Enterprise pricing and team licenses
(25:47) – What's next: Ui.sh and swimming downstream with AI
(27:40) – Founder fitness: 15-minute weighted vest circuits
(33:01) – Tracking strength gains as motivation
(39:13) – Did getting fit make Adam a better founder?
Links from the show:
MicroConf Europe ┃Reykjavik, Iceland · Sept 21–23, 2026
Tailwind CSS
Tailwind Labs
ui.sh
Adam's Morning Walk Podcast
My Body Tutor
Adam Wathan (@adamwathan)┃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
Episode 824 | Crowded Markets, Problem Aware, A Stolen Idea, and More Listener Questions (with Jordan Gal)
2026/03/17
What do you do when a collaborator takes your idea and builds a competing product?
In this episode, Rob Walling is joined by fan favorite Jordan Gal to answer listener questions on some of the trickiest challenges founders face. They cover financing decisions like using debt to bridge cash flow gaps, competing in markets flooded with vibe-coded apps, and what to do when a collaborator takes your idea and runs with it.
Want to get your question answered? Submit it here for a future episode.
Episode Sponsor:
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.
Topics we cover:
(3:50) – Jordan Gal on Rosie's multichannel launch
(8:01) – Investing cash in slow-moving healthcare markets
(10:32) – Using debt or credit against signed contracts
(16:48) – Competing in crowded markets with vibe-coded apps
(24:34) – Should you offer advisory shares to design partners?
(30:38) – Selling to problem-aware but not solution-aware audiences
(37:35) – When a collaborator steals your startup idea
Links from the show:
TinySeed SaaS Institute
Stripe Capital
The Play Bigger Book
The SaaS Playbook
Rob Walling's Books
Rob Walling's Newsletter
Rosie AI
Jordan Gal (@JordanGal) | 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
Episode 823 | Hot Take Tuesday: Is A.I. Killing B2B SaaS?, ChatGPT Ads, OpenClaw
2026/03/10
Is AI really killing B2B SaaS, or is it just subscription software by another name?
In this Hot Take Tuesday, Rob Walling, Einar Vollset, and Tracy Osborn dig into the market panic around SaaS stocks, whether AI models are actually getting better, ChatGPT's move into advertising (and Anthropic's spicy response), and the explosion of OpenClaw. They also tackle QSBS and when SaaS acquisitions shift from asset to stock purchases.
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:
(3:52) – M&A guide for B2B SaaS founders
(6:35) – QSBS and asset vs. stock purchase thresholds
(9:25) – Is AI killing B2B SaaS?
(16:27) – Are AI models noticeably better than a year ago?
(17:27) – ChatGPT vs. Claude: real-world experiences
(26:17) – ChatGPT ads and Anthropic's Super Bowl response
(29:34) – The opportunity for SaaS founders in new ad networks
(32:29) – OpenClaw: hype or substance?
Links from the show:
MicroConf US April 12-14, 2026 · Portland, Oregon
Discretion Capital’s M&A Guide
TinySeed SaaS Institute
AI is Killing B2B SaaS by Namanyay Goel
OpenClaw is What Apple Intelligence Should Have Been by Jake Quist
Rob Walling @robwalling | X
Einar Vollset @einarvollset | X
Tracy Osborn (tracymakes) | Blue Sky
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...
Episode 822 | No-code vs. A.I. Coding, SaaS Margins in the A.I. Age, and More Listener Questions (with Derrick Reimer)
2026/03/03
Should you build your SaaS with no-code tools, or is AI coding the better path forward?
In this episode, Rob is joined by fan favorite Derrick Reimer to tackle listener questions on no-code vs. AI vibe coding, when to take small funding early vs. pure bootstrapping, whether SaaS margins will compress as AI makes building cheaper, and how to get truly useful feedback from your customers.
Want to get your question answered? Submit it here for a future episode.
Episode Sponsor:
Hiring engineers right now is kinda broken. AI resumes, fake profiles, people who look senior on paper but can't ship anything real.
G2i cuts through all of that. They've pre-vetted over 8,000 engineers- not "we glanced at their GitHub" vetted, actually tested with live technical interviews. Contract or full-time- just tell them what you need and within days you're reviewing real candidates.
And you get a risk-free trial. If it's not a fit, they'll replace the dev in 24 hours.
G2i is trusted by companies like Meta, 1Password, 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
️ Want to attend their AI Miami in April? Use promo code Rob50Off
Topics we cover:
(2:18) – No-code vs. AI vibe coding for SaaS
(7:55) – What Rob would do as a non-developer today
(11:10) – Will you have to rewrite AI or no-code apps later?
(17:08) – Taking small funding early vs. bootstrapping
(21:29) – De-risking before taking funding
(27:42) – Will AI compress SaaS margins?
(31:32) – Why brand and positioning still win
(37:38) – Expanding your value chain with AI
(39:47) – Getting actionable feedback from customers
Links from the show:
MicroConf Europe 2026 – Join us in Reykjavík, Iceland (Sept 21–23)
Discretion Capital - M&A Advisory for B2B SaaS with $2-25m ARR
SavvyCal
SavvyCal Appointments
TinySeed
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
Episode 821 | How to Do Founder-Led Marketing (with Jay Clouse)
2026/02/24
Is founder-led marketing right for your SaaS, or just a distraction?
In this episode, Rob Walling sits down with Jay Clouse, founder of Creator Science, to explore founder-led marketing. They dig into how Jay overcame his own limiting beliefs about creativity, why most SaaS founders probably shouldn't pursue content creation, and how to evaluate whether building an audience makes sense for your specific business.
This is part one of a two-part conversation. Head to the Creator Science podcast to hear Jay interview Rob about SaaS, being a creator, and how he prioritizes his time.
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.
Need to ship faster without expanding your team?
Gearheart is an AI-powered product studio that helps startups build B2B SaaS apps and AI agents, fast. Their team ships at twice the speed of traditional dev shops and understands how to work within startup constraints.
Whether you need a fractional CTO or experienced engineers to accelerate development, Gearheart plugs directly into your workflow and delivers. They’ve built 70+ products, including SmartSuite, which raised $38M and is used by companies like Capital One.
As a listener, you get the first 20 hours of development free when you mention the podcast.
gearheart.io
Topics we cover:
(3:17) – What is Creator Science and who it serves
(6:49) – “I’m not creative”: Jay’s mindset shift + advice for founders
(11:38) – Examples of ultra-niche creator businesses
(13:54) – Why founders should create content for customers (not other founders)
(19:02) – Discovery vs. relationship channels: where attention actually comes from
(20:10) – Who Should Pursue Founder-Led Marketing?
(24:17) – Picking platforms based on where your customers already are
(31:43) – Founder-involved vs. founder-led marketing
Links from the Show:
MicroConf Europe┃Reykjavik, Iceland · Sept 21-23
Creator Science
Creator Science Podcast (Part two of this conversation)
Jay Clouse┃LinkedIn
Episode 820 | When to Quit Your Day Job, A.I. Feasibility Risk, and More Listener Questions (Rob Solo)
2026/02/17
When do you finally quit your day job and go all-in on your startup?
In this solo episode, Rob Walling answers listener questions about when it’s worth taking funding to speed up your path to full-time, how to think about equity when a co-founder joins late, and whether A.I. is shifting startup risk from market risk to feasibility risk. He also breaks down how to treat a low-priced, high-churn plan as “cheapium,” when to kill it, and how to test freemium without making a decision you can’t undo.
Want to get your question answered? Drop it here.
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:
(2:48) – When is it time to quit your day job, and should you raise funding to do it faster?
(4:35) – The “emotional runway” problem (and why bootstrappers burn out)
(10:06) – Equity splits: when to talk about it, and what actually matters
(13:57) – Late co-founder vs. business partner: how traction changes the %
(18:34) – Is A.I. increasing feasibility risk (aka tech risk) for startups?
(25:01) – Should a cheap, high-churn plan be treated like a marketing channel?
(26:19) – “Cheapium” pricing: when to keep it, kill it, or test freemium
Links from the Show:
Apply to TinySeed - Applications are until Feb 17th, 2026
The SaaS Playbook by Rob Walling
MicroConf - Community for SaaS Founders
Slicing Pie by Mike Moyer
Die With Zero by Bill Perkins
Dharmesh Shah
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
Episode 819 | QSBS, Exit Multiples, How to Learn Marketing, and More Listener Questions (Rob Solo)
2026/02/10
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:
Episode 818 | What Does It Take to Be Successful? with Russ Walling
2026/02/03
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
Episode 817 | Bootstrapping in the Age of AI with Jason Cohen
2026/01/27
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:
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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:
(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
Episode 816 | Developing an Editorial Eye, The Right Kind of Stubborn, and The Power of Focus (A Rob Solo Adventure)
2026/01/20
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...
Episode 815 | Unexpected Skills Your Day Job Can Teach You About Entrepreneurship (Rob Solo)
2026/01/13
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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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:
Podcast reviews
Read Startups For the Rest of Us podcast reviews
Murphycj 2026/01/30
My favorite tech / startup podcast
Been listening for a couple years. It’s really great. Rob is unassuming, low ego, and a good interviewer. I like the mix of solo episodes and interest...
Lucy SV, NP 2024/10/01
I’m not a saas entrepreneur, but the content is relatable
So yeah, I’m not a saas entrepreneur, but I find that the content is relatable, insightful, down to earth, and does NOT sound super scripted. 10/1/24 ...
Eugeniawoo 2024/08/20
A MUST for SaaS entrepreneurs
As my team and I are growing in the SaaS space, I find this podcast a MUST for both aspiring and seasoned SaaS entrepreneurs. Rob consistently deliver...
staticnull 2024/05/28
Dedication
They put an episode out every week!
geol9 2024/04/15
Too much self-promotion
I loved this show for years but it has become way too promotional of Robs investments. I have to skip 2:30 on each episode now. And the microconf yout...
yuritomi 2023/11/30
Honest, tactical, real stories and advice for bootstrappers
This is my go-to podcast for inspiration from other bootstrapped entrepreneurs! I so appreciate Rob’s candidness about his personal journey and the ta...
pedro.assumpcao 2023/05/18
The best startup podcast by far
Thanks Rob for all the invaluable information you provide around startup, SaaS, and bootstrapping businesses. Your podcast became my top source of inf...
Rick-detamoov 2023/01/11
Learnings from the novice to the advanced
Even as a serial bootstrapper, I find key learnings in each episode I can apply to my current venture. So glad I found this podcast and appreciate the...
Stretch Edu 2023/01/04
🐐
Rob is the GOAT! The convos on this pod are gold. Thanks for sharing them.
marty6162 2022/10/16
Inspiring stories and actionable advice
I found the podcast 2 years ago when I was just starting my first SaaS(jBoard) and loved the podcast. One of the few podcasts that have inspiring stor...
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