Finding Interesting Problems with Interesting People
Why the who matters as much as the what in building companies.
Finding Interesting Problems with Interesting People
Early in my career, I optimized for the idea. What's the biggest market? What's the best opportunity? What will make the most money?
Now I optimize for something different: interesting problems with interesting people.
The shift changed everything about how I build companies.
The Old Model
The conventional startup wisdom goes:
- Find a big market
- Identify a problem
- Build a solution
- Assemble a team
- Scale
The idea comes first. People are resources you add to execute the idea.
This model works sometimes. But it has failure modes:
- You end up working on things you don't care about
- You hire for skills, not fit
- When things get hard (they always do), motivation evaporates
- Success feels hollow if you don't enjoy the journey
The New Model
My approach now:
- Find people I want to work with
- Together, find problems we're excited to solve
- Build solutions we're proud of
- Let scale be a byproduct, not a goal
The people come first. The problem emerges from collective curiosity and capability.
What Makes a Problem "Interesting"
Not every problem is worth solving. Interesting problems have characteristics:
Genuine Frustration
The best problems come from real frustration. Not "I think users might want this" but "I've experienced this pain and it's unacceptable."
DuckDuckSign came from frustration with paying $25/month for e-signatures. Alignmint came from watching nonprofits struggle with terrible software. Band Voyage came from seeing Nashville musicians drown in business tasks.
Genuine frustration sustains you when building gets hard.
Intellectual Challenge
Some problems are interesting because they're hard. Not just "lots of work" hard—genuinely difficult to solve well.
Roladexter involves hard AI problems. How do you extract meaning from conversations? How do you build relationship graphs from unstructured data? These are intellectually engaging challenges.
If the problem doesn't make you think, you'll get bored.
Clear Impact
Interesting problems have clear impact when solved. You can see how the world gets better.
Helping nonprofits manage their finances better means more resources for their missions. Helping artists manage their careers means more music in the world. The impact is tangible.
Abstract problems ("optimize engagement metrics") don't sustain motivation the same way.
What Makes People "Interesting"
Not everyone is a fit for the way we work. Interesting people share certain traits:
Curiosity
Interesting people are genuinely curious. They ask questions. They want to understand how things work. They read widely and think deeply.
Curiosity drives learning, and learning drives improvement. Incurious people plateau.
Opinions, Loosely Held
Interesting people have strong opinions but update them when presented with evidence. They're not wishy-washy, but they're not dogmatic either.
This balance is rare. Most people either have no opinions or won't change them.
Complementary Skills
The best teams have complementary skills. If everyone's a developer, who talks to customers? If everyone's a visionary, who executes?
I look for people who are great at things I'm bad at. This creates teams that cover more ground.
Low Drama
Some people create drama wherever they go. Interesting people don't. They focus on the work, handle conflict maturely, and don't need constant attention.
Life's too short for drama. Building companies is hard enough without manufactured conflict.
Shared Values, Different Perspectives
Values alignment matters. If we disagree on fundamentals—integrity, quality, how to treat people—we can't work together.
But within shared values, different perspectives are gold. Diverse viewpoints catch blind spots and generate better ideas.
How We Find Each Other
Work Together First
The best way to know if you work well together is to work together. Before committing to a company, do a project. See how collaboration feels.
Many Blackbox Holdings collaborations started as small projects that grew into companies.
Be in the Arena
Interesting people are doing things. They're building, creating, shipping. You find them by being in the arena yourself.
Write publicly. Build in public. Attend events. Contribute to communities. The people you want to meet are doing the same.
Say Yes to Coffee
When someone interesting reaches out, say yes. A 30-minute coffee can lead to a decade-long collaboration.
I've met co-founders, investors, and lifelong friends through random coffee meetings. The ROI on being accessible is enormous.
Trust Referrals
Interesting people know other interesting people. When someone you respect makes an introduction, take it seriously.
My network has grown primarily through referrals. Each great person introduces you to more great people.
The Compound Effect
Working with interesting people on interesting problems compounds:
Better ideas: Diverse, curious people generate better ideas than homogeneous teams.
Faster learning: You learn from people who know things you don't.
Stronger resilience: When you genuinely enjoy your collaborators, hard times are more bearable.
Expanding network: Interesting people introduce you to more interesting people.
Career satisfaction: Even if a project fails, you enjoyed the journey.
The Blackbox Holdings Culture
This philosophy shapes how we operate at Blackbox Holdings:
- We don't hire for roles; we hire people and find roles
- We prioritize culture fit alongside skills
- We work on problems that genuinely excite us
- We'd rather build something meaningful slowly than something meaningless quickly
Not every company should operate this way. If you're optimizing purely for growth, different approaches might work better.
But for us, this is the game worth playing.
An Invitation
If you're working on interesting problems, I'd like to hear about them. If you're an interesting person looking for collaborators, let's talk.
The best opportunities come from unexpected connections. Maybe this is one of them.
The what matters. But the who matters more. Find people you want to spend years with, then figure out what to build together. The rest follows.