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.

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 SaaS actually protected from AI disruption, or are acquirers walking away without even looking?

In this episode, Rob Walling talks with Einar Vollset of Discretion Capital for a front-lines SaaS M&A market report, covering how the acquisition climate has shifted since 2021, why some PE firms now require at least one AI moat before they'll even look at a deal, and a breakdown of all five moats: hardware-software coupling, two-sided network effects, communication graph embeds, proprietary data with closed feedback loops, and operational switching costs. 

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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Are you using AI in your marketing because it's actually good, or just because it's fast?

In this episode, Rob Walling sits down with Taylor Hendricksen, a performance marketer who has managed tens of millions of dollars in ad spend across Meta and Google, to talk about where AI is genuinely useful and where it produces flat, mediocre output that makes you look like everyone else. They also dig into unconventional distribution channels, offer design, and why some of the best SaaS niches are the least exciting ones. 

Your AI-generated code got you to V1. Now it's holding you back.

Vibe coding is incredible for speed. But the codebase it leaves behind? Hidden security gaps, duct-tape architecture, features that break every time you ship. At a certain point you need professional engineering discipline, not more prompting.

That’s where Designli's Engineering Intensive comes in. In two weeks, senior engineers audit your code, stress-test your infrastructure, surface vulnerabilities, and deliver a prioritized roadmap to get scale-ready. Total clarity on your product's health, with a money-back guarantee.

Schedule your Engineering Intensive at designli.co/fortherestofus.

Podcast listeners can also redeem a free Designli Impact Week.

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 AI actually making your build-measure-learn cycle faster, or just making your work more average? 

In this episode, Rob Walling talks with Eric Ries, author of The Lean Startup, to revisit what's held up in Lean Startup thinking 15 years on, why AI speeds up building but can't replace human learning, and what drove Eric to write his new book, Incorruptible. Eric also shares the story of how the Long-Term Stock Exchange nearly died before it ever launched, and why Costco is the rare example of a company that figured out how to stay incorruptible. 

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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What do Nobel Prize winners and successful bootstrappers have in common? 

In this solo episode, Rob Walling shares the story of how a TinySeed company went from near-zero revenue to $10,000-$20,000 a month almost overnight, breaks down Claude Shannon's research on the habits that separated Nobel laureates from forgotten scientists, and explores why deep expertise looks like magic from the outside.

You're about to close a massive deal, and then your customer's legal team asks what happens if you get hacked. 

That's the nightmare YSecurity solves. They're 40 security engineers who've worked at Apple, Uber, Microsoft, Robinhood, Brex, and more. You don't hire them, you rent them by the hour, no massive salary, no expensive consultants. Just real experts helping you get SOC 2, ISO, and more.

Set a monthly cap, know exactly what you're spending, and close the deal. 

Head to ysecurity.io/startups to book your free strategy call. Your first 8 hours are completely free.

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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How do you leave a $400K salary to go all in on your business?

In this solo episode, Rob Walling cranks through a backlog of listener questions on reducing risk with your startup to go full-time, when to register as a business, how to price a SaaS with seat ambiguity, when to pivot, and how to keep building when you have four kids under eight. 

Want to get your question answered? Drop it here.

Your AI-generated code got you to V1. Now it's holding you back.

Vibe coding is incredible for speed. But the codebase it leaves behind? Hidden security gaps, duct-tape architecture, features that break every time you ship. At a certain point you need professional engineering discipline, not more prompting.

That’s where Designli's Engineering Intensive comes in. In two weeks, senior engineers audit your code, stress-test your infrastructure, surface vulnerabilities, and deliver a prioritized roadmap to get scale-ready. Total clarity on your product's health, with a money-back guarantee.

Schedule your Engineering Intensive at designli.co/fortherestofus.

Podcast listeners can also redeem a free Designli Impact Week.

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

Should your first customer pay you, or get your product for free? 

In this episode, Rob Walling answers listener questions on charging customer zero, what metrics to track for a seasonal transaction fee-based SaaS, what it really means to sell into a low-awareness market, and when freelancers help vs. hurt your bootstrapped business. He also calls in Producer Ron to break down exactly how he thinks about writing copy for a podcast ads.

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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What were the highlights and takeaways from MicroConf? 

In this episode, Rob Walling and Derrick Reimer recap MicroConf US 2026 in Portland, Oregon. They break down the best talks from the event, including Jason Cohen on breaking through growth plateaus, Amanda Natividad on Zero-Click Marketing and broken attribution, Rob's framework for six ways to implement AI in SaaS, and Craig Hewitt's all-in take on AI adoption. Plus, they cover excursions, the hallway track, and why the MicroConf community keeps pulling founders up.

You're about to close a massive deal, and then your customer's legal team asks what happens if you get hacked. 

That's the nightmare YSecurity solves. They're 40 security engineers who've worked at Apple, Uber, Microsoft, Robinhood, Brex, and more. You don't hire them, you rent them by the hour, no massive salary, no expensive consultants. Just real experts helping you get SOC 2, ISO, and more.

Set a monthly cap, know exactly what you're spending, and close the deal. 

Head to ysecurity.io/startups to book your free strategy call. Your first 8 hours are completely free.

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 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.

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.

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.

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