Starting a podcast is easy. Sustaining one long enough to learn something meaningful is not.
To close out 2025, Aaron Marchbanks and Justin Edwards took a step back to reflect on the first year of SaaS That App: Building B2B Web Applications.
Instead of chasing trends or predictions, they revisited the moments that quietly reshaped how they think about building software, leading teams, and growing companies.
What emerged was a collection of insights that feel less like best clips and more like a playbook for founders, engineers, and operators navigating modern SaaS. From imposter syndrome in the C-suite to why culture outperforms perks every time, these ten moments captured the reality behind building real products with real people.
Imposter Syndrome Doesn’t Disappear at the Top
The first standout moment came from the show’s very first guest, TK Herman, who openly admitted that even as a CEO, he once felt afraid to ask questions in meetings at his own company. Not because he lacked intelligence, but because of the story he told himself about what leaders are supposed to know.
That moment resonated because it reframed imposter syndrome as a leadership constraint, not a personal weakness. When leaders stop asking questions, teams lose clarity. When curiosity disappears, alignment follows. The lesson was simple and disarming: the most confident leaders are often the most curious ones.
Cheap Tooling Isn’t the Same as Business Readiness
Joe Kowalski’s clip tackled one of the most common misconceptions in modern SaaS: that affordable tooling makes running a company easier.
Yes, it’s never been cheaper to launch a product. Today’s founders can spin up a full stack for a few hundred dollars a month. But as Joe pointed out, access to tools doesn’t magically grant skills in sales, finance, hiring, or leadership.
Great engineers don’t automatically become great operators. Tooling lowers barriers to entry, not the complexity of building something that lasts.
Momentum Is Built, Not Found
Tom Hunt offered one of the most elegant metaphors of the season: business as a flywheel.
In the early days, every turn feels heavy. Progress is slow and invisible. But each deliberate action compounds, and over time, momentum builds. The key isn’t speed, it’s identifying which parts of the cycle you can control and improving them consistently.
This perspective strips growth of its mythology. Success isn’t about viral moments or sudden breakthroughs. It’s about understanding systems and showing up long enough to let them work.
Selling a Business Is a One-Way Door
Rob Walling appeared twice in the episode, and both moments landed with uncommon clarity
First, he framed selling a business as a one-way door. Once you exit, there’s no undo button. That reality demands conviction, not just financial logic. If you love the work, don’t sell. If you sell, be prepared to let go completely.
Later, Rob offered a necessary level-set: SaaS is emotionally difficult, but perspective matters. Building software is mentally draining, not physically punishing. Gratitude and humility aren’t optional; they’re survival tools.
When Not to Rewrite
Several moments focused on technical judgment, particularly from Nolan Alimonti. One recurring theme was restraint. Frameworks provide defaults for a reason, and deviating from them should require strong justification. Staying within recommended tooling often reduces long-term maintenance costs and team friction.
Even more important was the distinction between technical debt and product uncertainty. Rewrites don’t solve unclear product direction. They only succeed when requirements are stable, and outcomes are well understood. Otherwise, teams simply migrate the same problems into a new codebase.
Diagnose Before You Prescribe
Ben Curtis reinforced a philosophy that runs throughout SaaS That App: good partnerships start with listening.
Before recommending solutions, teams need to understand motivations, constraints, and goals. Sometimes the right answer isn’t building at all. Trust is earned by helping clients succeed, not by maximizing billable work.
Brian Stinar echoed this idea from another angle, emphasizing that motivation matters more than resources. Teams build credibility by recommending what’s right, not what’s convenient.
Culture Is the Real Competitive Moat
The episode closed with Steve Powell, whose perspective on culture cut through years of startup clichés.
Culture is more than just ping-pong tables, snack walls, or office perks. It’s shared values, mutual respect, and enjoying who you work with. Steve describes culture as a moat, one that attracts smart people and keeps them engaged long after novelty fades.
Across ten moments, that idea tied everything together. Tools evolve. Frameworks change. Markets shift. But people remain the constant.
Final Thoughts
The first year of SaaS That App wasn’t about finding shortcuts. It was about asking better questions, building healthier systems, and learning in public. These moments established a philosophy: build deliberately, lead with humility, and remember that software is ultimately a people business.
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