You're staring at the decision: hire your first person or stay solo. Everyone says you need a team to scale. But what if they're wrong?
Jason Cohen ran SmartBear Software solo at seven figures and turned down acquisitions because staying solo was his competitive advantage. This episode isn't about choosing the "right" path—it's about understanding you're choosing between two different games. Solo gives you freedom, speed, and full control. Teams give you leverage, collaboration, and the ability to build beyond yourself. Both can win. But you can't play both games at once.
The moment you add even one person, everything transforms. Code requires coordination. Marketing needs alignment. Decisions require consensus. Solo founders move without these constraints. That speed is a weapon until it hits a ceiling. The question isn't whether teams are better than solo—it's which constraint you're choosing to optimize for.
Solo doesn't mean isolated. The deadliest trap is operating without external perspective. You need a personal board of directors—critics and mentors who've navigated harder challenges. Not networking groups where everyone complains about how hard it is. You need people further ahead who spot your blind spots before they wreck you. These relationships are often pay-to-play because people genuinely ahead aren't hanging out in free communities.
The hardest shift is moving from building to selling. Builders love adding features. Sales means tolerating rejection. The temptation is outsourcing what you hate. Don't. Delegating work you don't understand guarantees failure. If you can't evaluate quality in your weakest area, you're betting blind on expensive mistakes. You can't tell if the approach is wrong or if the product doesn't resonate. Master it first, then delegate later when you can spot the difference between good work and bullshit.
Solo founders fail when they mistake craft mastery for business mastery. Being exceptional at your core skill isn't enough. Running a business means handling everything—accounting, legal, operations, marketing, sales, product. Systems thinking means organizing work into repeatable processes. Without structure, you drift between whatever feels urgent. That creates reactive work where nothing compounds.
Automation comes before hiring. Tools available today replace what required full teams three years ago. AI handles customer service and content. No-code builds products. Exhaust these options before adding payroll. People are expensive and complicated. Software is cheap and predictable.
Solo founders also get stuck in build mode. One more feature. Better messaging. This perfectionism is fear disguised as quality control. Shipping means facing judgment. The balance is launching at minimum credibility—interesting enough for engagement and feedback. Not polished, but coherent. Speed matters more than polish once you cross that threshold.
Three failure modes hit predictably. First is isolation. Without teammates, there's no one to celebrate wins or process losses with. Second is scattered focus. Every idea pulls attention. You start ten projects and finish none. Partners keep you tracking toward shared vision. Solo founders need brutal prioritization to achieve similar results. Third is staying solo too long. Revenue plateaus. You've automated everything and you're still the bottleneck. That's the signal—either accept the ceiling and optimize for lifestyle, or build the team that creates new capacity.
Staying solo is legitimate. It can generate seven-figure revenue with zero employees. It requires systems thinking, comfort with sales, mastering multiple functions, and discipline without external accountability. The advantage is keeping all control and moving without coordination overhead. The ceiling is your personal capacity.
You're not behind for staying solo. You're not winning for building a team. You're choosing which game to play. If you want lifestyle and freedom, solo works. If you want to build something beyond yourself, you need people. Just know which constraint you're optimizing for before you make the choice. And don't hire until you've mastered what you're delegating.
Watch the Full Episode on The Solo Founder Path below:
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