Startups For the Rest of Us

Latest Episodes:

Episode 796 | Marketing Isn't Easy?, How to Grow Your Company, and Be Careful Who You Listen To (A Rob Solo Adventure) Sep 16, 2025

Show notes

What if your SaaS isn’t growing because of the product, not the marketing?

In this solo adventure episode, Rob Walling unpacks why SaaS marketing feels harder than ever and why most advice out there will waste your time. He shares how he’d approach things if growth has stalled, the questions he’d ask first, and why real progress comes from proven fundamentals.

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Topics we cover:

(2:20) – Why marketing is harder than ever, and what’s changed
(3:40) – The Dunning-Kruger Effect
(11:30) – Marketing is not just convincing someone to buy what you've built.
(16:30) – Validating vs. throwing dice at a wall
(20:03) – Is there a ‘one right way’ to grow a business?
(25:00) – Be careful who you listen to

Links from the Show:

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 795 | TinySeed Tales s5e4: The $20K Milestone Sep 11, 2025

Show notes

Harris hit $20k MRR. It’s real. What’s next?

In this episode of TinySeed Tales, Rob Walling celebrates with Harris Kenny after OutboundSync crosses $20k MRR ahead of schedule. They talk about why hitting a milestone can feel both exciting and overwhelming, the arrival fallacy, and how simple, consistent execution may be all it takes to reach $30k. Harris shares the bets that moved the needle, including Salesforce, SOC 2, and what hidden demand taught him about building integrations before anyone asked.

Topics we cover:

(1:32) – Crossing $20k MRR and aiming for $30k
(6:29) – The Salesforce bet
(8:17) – Runway, burn, and pricing upmarket
(10:34) – Raise capital or keep bootstrapping
(15:03) – SOC 2 as a sales unlock
(20:11) – Marketplace credibility and AppExchange
(22:05) – Hidden demand for Salesforce
(26:11) – The push to $30k and parity

Links from the Show:

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 794 | From Struggling Side Project to Life-Changing SaaS Exit Sep 09, 2025

Show notes

B2C, low price point, one-time payments… not the typical recipe for a life-changing exit.

In this episode, Rob Walling talks with longtime listener Zamir Khan, founder of VidHug (now Memento). Zamir’s story broke a lot of SaaS “rules”: B2C, low price point, one-time payments, and years of slow growth. He shares how he nearly gave up, the pandemic surge that changed everything, and the emotional ride that led to a life-changing exit.

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Topics we cover:

(3:47) — From podcast listener to SaaS founder
(7:59) — The role of luck, timing, and the pandemic in growth
(18:37) — A birthday gift becomes a product
(23:54) — Charging early and surviving slow growth
(30:47) — From $1k a month to 80k daily users
(39:58) — Support load, stress, and the edge of burnout
(48:58) — Deciding to sell (and why timing mattered)
(52:57) — Life after the exit: slowing down and finding balance

Links from the Show:

TinySeed – Applications close tonight!
MicroConf Connect – The community for SaaS founders
The SaaS Playbook
Memento (formerly VidHug)
Zamir Khan (@zam1rkhan) | X
Zamir Khan | 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

Episode 793 | TinySeed Tales s5e3: Building Momentum Sep 04, 2025

Show notes

What happens when momentum hits and your biggest challenge becomes keeping up?

In this episode of TinySeed Tales, Rob Walling catches up with Harris Kenny, founder of OutboundSync. Revenue is growing, the team is moving fast, and enterprise leads are coming in. But with success comes complexity: support load, pricing strategy, and product demands are all increasing. Harris is hiring again, learning to say no, and figuring out how to keep the momentum without losing focus.

Topics we cover:

(1:40) – Closing his biggest deal ever and what it unlocked
(4:26) – Learning how to do enterprise sales
(6:20) – How SOC 2 made the product stronger
(12:18) – New hires are paying off
(18:23) – Building the Salesforce integration
(22:13) – Getting pull from the market, not pushing
(24:10) – Taking customers from unicorns

Links from the Show:

TinySeed SaaS Accelerator - Applications close on September 9th
Coaching Call Bonus
Invest in TinySeed
YNAB (You Need A Budget)
Dynamite Jobs
OutboundSync
Harris Kenny | 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

Episode 792 | Hot Take Tuesday: GPT-5 Struggles, the A.I. Bubble, and the Windsurf Debacle Sep 02, 2025

Show notes

Is GPT-5 a real risk for SaaS founders, or just the beginning of a new chapter?

In this Hot Take Tuesday, Rob Walling, Einar Vollset, and Tracy Osborn dig into GPT-5’s mixed reviews, signs of stress in the A.I. bubble, and how Windsurf’s $2.4B exit left early employees with nothing. They also unpack why returning a VC fund is such a rare (and big) deal.

Episode Sponsor

This episode is brought to you by Gearheart.io, which specializes in helping early-stage founders validate ideas, prototype SaaS products, and build AI-powered MVPs with real user testing, so your code won’t crumble when your first customers show up.

Founded by entrepreneurs who’ve launched and exited their own startups, Gearheart has helped launch over 70 B2B SaaS products, including SmartSuite (which raised $38 million). They get where you’re at.

Book your free strategy session at gearheart.io and mention Startups for the Rest of Us to get 20% off discovery, validation, or prototyping services.

Topics we cover:

(3:12) – TinySeed returns Fund One
(9:40) – GPT-5: Upgrade or letdown?
(19:19) – Are we in an AI bubble?
(24:09) – The Windsurf debacle: $2.4B exit, $0 for early employees
(31:06) – The bigger problem: Are startups forgetting to share the upside?
(40:05) – Lifestyle vs. Ambitious Bootstrapping

Links from the Show:

TinySeed Fall 2025 Applications Live Q&A - Join us Wednesday September 3rd
TinySeed SaaS Accelerator - Applications are Open!
Invest in TinySeed
MicroConf
SaaS Institute
Discretion Capital
Einar Vollset | LinkedIn
Einar Vollset (@einarvollset) | X
Tracy Osborn
Tracy Osborn | LinkedIn
Tracy Osborn (@tracymakes) | 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 791 | TinySeed Tales s5e2: Growing Pains Aug 28, 2025

Show notes

In this episode of TinySeed Tales, Rob Walling reconnects with Harris Kenny, founder of OutboundSync, to explore the rapid evolution of his SaaS business just months after transitioning from agency work.

Harris shares how niching down to outbound-focused agencies unlocked sales momentum. He talks about hiring, his Salesforce breakthrough, SOC 2 prep, and why finally spending his TinySeed funding changed everything.

Topics we cover:

(2:27) – Launching a lower-priced version and building expansion revenue
(6:40) – How lead-gen shops are outpacing legacy rev ops
(12:01) – Hiring full-time: Dev speed, onboarding load, and customer success firepower
(18:15) – A surprise Salesforce breakthrough and what it means for product strategy
(24:42) – SOC 2 prep, pricing confidence, and finally spending the TinySeed check

Links from the Show:

Join the TinySeed Mailing List
Apply for TinySeed - Applications reopen September 1, 2025
OutboundSync
Harris Kenny | LinkedIn
Coaching Call Bonus
Dynamite Jobs
Vanta

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 790 | From Scrappy to Scalable: Evolving Your Role as a Founder Aug 26, 2025

Show notes

How can you scale yourself as a founder?

In this episode, Rob Walling is joined by Yaniv Bernstein (co-founder and CTO of Vera, former COO, VP of Engineering, and Google leader) to unpack how a founder’s role must change as the company grows. From writing the code yourself to leading managers of managers, they dig into the tough transitions every founder faces, and what happens if you don’t adapt.

Topics we cover:

(3:27) – How the founder/CEO role changes as your SaaS scales
(8:44) – The turning point where systems and processes matter
(14:49 – When to hand off marketing, sales, or product as a founder
(19:44) – Why setting context is your #1 job as a founder-CEO
(28:19) – Why hiring right (and firing fast) makes or breaks scaling

Links from the Show:

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 789 | TinySeed Tales s5e1: From Agency to SaaS Aug 21, 2025

Show notes

Welcome to Season 5 of TinySeed Tales, the documentary-style series where we follow one SaaS founder’s journey over 12 months to hear about the wins, the missteps, and everything in between.

In this season premiere, Rob Walling introduces Harris Kenny of OutboundSync. After running a successful agency, Harris makes the leap to go all-in on SaaS. It’s a high-stakes transition that many agency owners are never able to make.

Topics we cover:

(2:25) – From agency owner to TinySeed-backed SaaS
(6:38) – Walking away from consistent agency revenue to go all-in on SaaS
(13:51) – Going all-in vs. splitting focus
(16:13) – Why most agencies fail at SaaS
(28:15) – What’s working, what’s not, and what’s next

Links from the Show:

Join the TinySeed Mailing List - Applications reopen in September 2025
Apply for TinySeed
Coaching Call Bonus
MicroConf Connect
OutboundSync
The SaaS Playbook
Harris Kenny | 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

Episode 788 | Do I Need a Co-founder? And More Listener Questions (with Derrick Reimer) Aug 19, 2025

Show notes

What are the real risks of AI-generated code and “vibe coding”?

In this episode, Rob Walling is joined once again by fan-favorite Derrick Reimer to answer a fresh batch of listener questions. They dig into solo vs. co-founder trade-offs, managing scope creep, and how integrations can shape early traction.

Want to get your questions answered? Drop them here.

Topics we cover:

(2:33) – Do you need a co-founder to succeed in SaaS?
(5:18) – The Risks of AI-Generated Code and “Vibe Coding”
(13:50) – How to manage scope creep as a solo founder
(23:32) – Finding and retaining great contractors
(39:43) – How to build a startup culture with a bias for action

Links from the Show:

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 787 | "We Shut Down a $1.5M Product, and Raised $10M Instead" Aug 12, 2025

Show notes

How do you know it’s time to move on from a product that’s growing?

In this episode, Rob Walling chats with Braden Dennis, co-founder of Fiscal.ai (formerly FinChat), about a rare founder journey: bootstrapping, catching lightning in a bottle, and choosing to go big with venture capital. They dive into the emotional and strategic weight of shutting down a $1.5M ARR product, what shifts when you scale past 40 people, and why Braden prioritized long-term vision over short-term revenue.

Topics we cover:

(2:30) – From FinChat to Fiscal.ai: rebranding and repositioning
(6:50) – Why they raised a $10M Series A
(13:09) – From bootstrapped to venture-backed: what changes?
(19:56) – Becoming a real CEO at 25 employees
(26:44) – Why they shut down a $1.5M product
(30:30) – Lessons from having four co-founders
(33:13) – The benefits of joining TinySeed

Links from the Show:

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