Building with LLMs, Finding Founders & Future Planning: Expert Answers from 37signals

In a special listener Q&A episode of the REWORK podcast, 37signals co-founders Jason Fried and David Heinemeier Hansson tackle pressing questions about AI tools, startup partnerships, product development, and business longevity. Here are their key insights.

Developing Solo with AI: Risks & Realities

When iOS developer Ryan Chitwood asked about one-person teams using LLM tools like GitHub Copilot:

David Heinemeier Hansson noted:

🧠 "I've seen teammates dramatically increase output using LLMs, but serious limitations remain:

Enterprise-grade software requires code-review rigor
Security vulnerabilities frequently occur (citing the 'tea' app breach)
Best suited for non-sensitive applications like games without user data"

Jason Fried added:

⚠️ "Where developers hit the wall:

Troubleshooting abilities become critical when LLMs malfunction
Maintaining personal operational awareness is non-negotiable
Stress levels spike when solutions lie beyond your competence zone"

Conclusion: LLMs enable rapid prototyping but mandate realistic assessment of security needs and troubleshooting capabilities.

The Co-founder Dilemma: Necessity or Choice?

Responding to Anton's question about Y-Combinator's co-founder recommendations:

Why venture capitalists prefer teams:

"Risk distribution. Solo founder exits permanently disable company operations, which worries investors."

Effective partner identification strategies:

"Found organic partnerships through school/work interactions first. Digital encounters still represent the minority successful cases."

The founders disagree with obligatory partnerships:

🛑 Jason: "A bad partnership causes more damage than working solo. Complementary skill sets matter more than cloned abilities."

🧪 David: "Rushed co-founding resembles shotgun weddings. The most fertile recruiting grounds remain colleges and professional communities."

The Founder Succession Question

When asked about preparing 37signals for future leadership:

🚪 David: "We'd likely sell rather than install surrogate leadership. Founder advisory roles create untenable power ambiguity."

💼 Jason: "Some companies simply shouldn't outlive founders. We're fundamentally intertwined with Basecamp's DNA after 22 years."

They noted structural obstacles make transitions unrealistic:

Current ownership requires continued founder distribution authority
Post-sale separation is cleaner than attempting gradual handoffs
Business models dictate succession feasibility regardless of good intentions

Product Creation: Talent vs. Exposure

Addressing Brent's query about product ideation processes:

Jason explained their imperfect approach:

"In 22 years, only Basecamp became the foundational anchor product
New concepts arise from internally identified needs ('getting snagged')
Avoid speculative validation - real usage reveals flaws"

David emphasized experiential learning:

"Breakthrough ideas emerge through wrestling with system failures – not vacuums"
"Professional exposure beats forced brainstorming sessions"
"We developed sharper problem-detection through running multi-product operations"

Critical Distinction:

✨ "Talent matters less than developing 'hook awareness' – noticing industry stagnation points. For example, launching Hey emerged from recognizing email's neglected problems after 16 years of Gmail dominance."

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