Episode 797 | TinySeed Tales s5e5: Should I Raise More Funding?

OutboundSync just hit $35k MRR—but the decisions are only getting harder.  In this episode of TinySeed Tales, Rob Walling and Harris Kenny dive into the messy middle of SaaS growth, where every opportunity comes with a trade-off. They explore the tension between raising funds you don't need, staying focused when good ideas keep coming, and building a business while raising a family. Topics we cover:  (2:28) – From $20k to $35k MRR in three months (2:53) – The bets that moved the needle (4:56) – Infinite runway, SOC 2 wins, and building trust (8:29) – Saying no to good ideas with limited bandwidth (10:00) – Decision-making, value-driven growth, and agency DNA (13:14) – Should Harris raise more funding or stay focused? (15:52) – Why boring “pipes” matter in an AI world (20:25) – Trade-offs, mindset, and building for scale (25:35) – Hiring a sales coach and focusing on what works (27:52) – Balancing startup stress with parenting Links from the Show:  SaaS Institute Coaching Call Bonus 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

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. Episode Sponsor: Is your engineering team stretched too thin? Gearheart provides growing companies with AI-powered engineering talent that ships 2 times faster.  CTOs and engineering managers trust them to deliver critical features end-to-end with minimal oversight, whether it's fixing scaling failures, broken integrations, or system instability.  With 13 years of experience building sophisticated B2B platforms, they plug in fast and deliver results. They've helped build platforms like SmartSuite, which has scaled to thousands of organizations including industry giants like Capital One. Book your free strategy session at gearheart.io and mention this podcast to get 20% off discovery or embedded engineers for your team. That's gearheart.io. 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:  MicroConf Events MicroConf Mastermind Matching 75+ SaaS Marketplaces  The SaaS Playbook 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

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:  Invest in TinySeed Fund 3 Coaching Call Bonus MicroConf Events 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

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. Episode Sponsor: AI is completely changing how people discover brands and content online, and Ahrefs has built a full-blown SaaS marketing platform to help you stay ahead. With over 15 years of real-world web data, and AI that actually understands marketing, Ahrefs helps you measure your brand presence, build authority, and monitor reputation across search, social, and AI platforms like ChatGPT, Google AIOs, Perplexity, and more. You can also dig into what’s driving your competitors’ visibility and spot market gaps before they do, helping you create content that ranks and drive new traffic to your business. There's no need to juggle a bunch of disconnected tools- get Ahref’s all-in-one platform to make your brand unmissable in a fast-moving world.  Try it free at ahrefs.com/awt. 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

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

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

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

How can you scale yourself as a founder? In this episode, Rob Walling is joined by Yaniv Bernstein (co-founder and CTO of Violet, 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:  SaaS Institute MicroConf | The community for SaaS founders MicroConf YouTube Channel People Engineering  The SaaS Playbook  Yaniv Bernstein | LinkedIn Yaniv Bernstein (@ybernsteindig) | X The Startup 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

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

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:  MicroConf Europe | Istanbul, Sep 28-30, 2025 TinySeed Tales Podcast MicroConf Connect TinySeed Fund SavvyCal Derrick Reimer | LinkedIn 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