Startups For the Rest of Us

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:

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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!

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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: