Sep 1, 2026 · 34m · we-live-to-build
Nobody Wakes Up Excited to Use Software - So He Built This Instead
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
Host Sean Weisbrot interviews Heights Platform founder Brian McCanulty to discuss how digital creators and software companies can overcome psychological barriers, engineer daily habits, price knowledge products effectively, and leverage proactive AI agents to build resilient, outcome-focused businesses.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Sean holds 43.8% of the talking time here. How this is scored →
Sean as informed peer 4.8 Guest teaching 3.6 Guest disagreement 1.4 Sean pushing back 2.0
speaking balance: gold is Sean, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 18:14 Brian dismantles the recurring revenue myth
Brian directly rejects common startup wisdom, arguing that rushing into recurring revenue creates unmanageable churn that destroys creator lifetime value.
Hardest push from Sean ▶ 27:31 Sean challenges Brian's roadmap paceSean refuses Brian's casual release timeline, directly calling out that things are moving too fast in AI to delay releases by months.
Biggest teaching moment ▶ 19:00 Brian breaks down value-based pricing over cheap productsBrian educates Sean on unit economics, explaining why low-priced tiers are merely lead generation tools and why creators should sell high-ticket bundles instead.
Sean holds their own ▶ 28:25 Sean details his AI-driven codebase synchronizationSean demonstrates technical mastery by explaining how he leverages Cursor and Anthropic APIs across local GitHub repos to automatically keep marketing sites aligned with code updates.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Sean as informed peer | Guest teaching | Guest disagreement | Sean pushing back | Why |
|---|---|---|---|---|---|---|
| The Psychological Hurdle to Monetizing Knowledge | 4 | 3 | 1 | 1 | Sean frames the psychological bottleneck creators face when monetizing knowledge and references HubSpot pioneering inbound customer education. Brian agrees and elaborates on how educating customers on sales and marketing drives SaaS retention. | |
| Overcoming Founder Pitfalls and Instilling Habits | 6 | 1 | 0 | 1 | Sean shares an extended anecdote regarding his mentorship of a laid-off Meta employee and his experience with a former COO turned CEO, querying how Brian enforces accountability for long-term behavioral changes. | |
| Structuring Fixed-Date Challenges for Habit Formation | 5 | 4 | 1 | 2 | Brian explains the tactical power of fixed-date online challenges to drive habit formation. Sean relates this to incentivizing his own users with free months, which Brian validates while advising tighter feedback loops. | |
| Balancing New and Experienced Creators with Passive Value | 5 | 4 | 2 | 2 | Sean contrasts Heights with Beehiiv's programmatic audience monetization and cross-pollination. Brian clarifies Heights' white-label philosophy, emphasizing independent brand ownership over shared marketplaces. | |
| Building High-Engagement Creator Communities and Workshops | 6 | 2 | 1 | 2 | Brian admits he under-allocates time to his own creator community, prompting Sean to share a blueprint from an acquaintance grossing $250k a month through paid community events and roundtables. | |
| Rethinking Recurring Revenue and Value-Based Pricing | 4 | 7 | 3 | 1 | Brian reframes conventional subscription thinking, explaining that rushing into recurring revenue increases churn and reduces LTV. He urges creators to charge higher one-time rates and stop treating entry-level pricing as flagship products. | |
| The Evolution to 'Service as a Software' | 5 | 5 | 3 | 4 | Brian introduces the shift toward 'service as a software' delivering outcomes directly rather than button-clicking interfaces. Sean pushes back against the claim that nobody enjoys using software by citing his own daily obsession with AI coding tools. | |
| Heights AI 3 and Proactive AI Growth Agents | 5 | 3 | 2 | 5 | Brian previews Heights AI 3 proactive growth agents. Sean questions Brian on his release timeline, challenging the speed of his roadmap compared to the rapid pace of current AI developments. | |
| Shipping Velocity and Customer AI Education | 6 | 4 | 2 | 3 | Brian notes marketing and customer education lag behind software development. Sean shares his setup where Claude tracks GitHub repos to automate marketing copy updates in sync with app changes, which Brian cautions may oversimplify complex features. | |
| Scaling Support and Frustration Detection with AI | 6 | 4 | 1 | 1 | Sean describes his integrated architecture tying PostHog, Supabase, and Anthropic APIs together for live support escalation. Brian validates the approach and outlines Heights' sentiment detection for frustrated users. | |
| Brian McCanulty on Entrepreneurial Persistence and Conviction | 1 | 3 | 0 | 0 | Sean asks for the primary takeaway from Brian's entrepreneurial journey. Brian offers a closing monologue highlighting perseverance, personal sustainability, and self-belief before Sean concludes the episode. |
Statements from this episode (12)
Heights Platform has served more than 10,000 creators building online businesses
“We've now done that for more than 10,000 creators which I'm very proud of.”
Creator SaaS requires users to adopt a new identity to use it
“I think I think I picked a, in some ways a challenging business because it's a software as a service where the customer has to like truly make a decision to become somebody in order to be using your product.”
Time-bound challenges are ideal for activating knowledge business customers
“One of the best ways to do that, I think for people involved in some kind of knowledge business is with the online challenges. Online challenge, I would define as like some kind of A fixed calendar date online course experience that like people are going throu…”
Heights Platform customers are split evenly between novice and experienced creators
“I think it's like 50, 50 for us. So like half of the people have like maybe never sold online before. And half of the people have some kind of experience, either like as a full-time creator or doing something on the side.”
Sticky software products must provide passive value merely by existing
“In every, every product you have to think about what are the things where you can be providing some kind of value for the product to just exist for the person and which will like make it more sticky for the user.”
Creators should start with one-time pricing before moving to recurring subscriptions
“And for most creators, then what I think is better is to start with a one-time price, get really everything like dialed in and optimized and then decide like, okay, is this right to move into a subscription model in the future?”
Sub-$100 creator products are entry-level lead magnets, not flagship offers
“If like, if you see somebody out there with like a 99 dollar or less product, that product is not like, if they're successful in their business, that product is not their flagship product. That is like an entry level offer to capture leads and to the price of …”
Creators should add value to charge more, not compete on price
“And so I think most creators should aim not to compete on price and be the cheapest product, but instead, how can you deliver more value to charge more for your product? Because getting customers is hard, no matter what. And so I would rather take the approach…”
AI shifts the business model from SaaS to 'Service as a Software'
“If you heard the idea that people are talking about, it's not software as a service anymore. It's service as a software because of all these shifts with shifts with AI. You have to think of, okay, not how can we use AI to slightly reduce our costs or do someth…”
Product engineering now ships features faster than marketing teams can prepare
“The roles and responsibilities have flipped. It used to always be that like the marketing team is pushing the product, like, Hey, you guys gotta get this finished. We're trying to promote it. And now it's like the opposite. Now it's like, Hey guys, sorry, the …”
McCanulty: AI builders are one to two years ahead of average users
“A lot of like builders and probably people like listening or watching a show like this, like we're like a year or two ahead of the average user, even if they're an entrepreneur, most cases, because there there's just such a quick advancement in how these thing…”