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.

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.

• (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

• 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!

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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.

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.

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Check them out at every.io.

And if you're at MicroConf in Portland, make sure to swing by and chat with the team.

• (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

• 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

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.

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.

• (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

• 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...

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.

• (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

• 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

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.

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

• (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?

• 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

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.

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.

• (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

• 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

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.

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

• (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?

• 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...

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.

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

• (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

• 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