Running Multiple Companies: Systems and Sanity
How to manage multiple ventures without burning out.
Running Multiple Companies: Systems and Sanity
People ask how I run multiple companies at once. The honest answer: I don't run them. I build systems and teams that run them.
At Blackbox Holdings, we have seven active companies: DuckDuckSign, Alignmint, Roladexter, Band Voyage, Docusuck, Formell, and BizGift. Each has its own team, roadmap, and customers.
Here's how it works without everything falling apart.
The Wrong Mental Model
Most people imagine running multiple companies as:
- Constant context switching
- 100-hour weeks
- Being the bottleneck for everything
- Superhuman productivity
This model doesn't work. It leads to burnout, mediocre execution, and eventually failure.
The Right Mental Model
Running multiple companies is actually:
- Building systems that don't need you
- Hiring people better than you at their jobs
- Making fewer decisions, not more
- Saying no to almost everything
The goal isn't to do more. It's to enable more to happen without you.
The Operating System
1. Dedicated Teams
Each company has its own team. Not shared resources bouncing between projects—dedicated people focused on one thing.
| Company | Team Structure |
|---|---|
| DuckDuckSign | Engineering lead + 2 devs, 1 designer |
| Alignmint | Engineering lead + 2 devs, 1 product |
| Roladexter | Engineering lead + 1 dev, 1 ML engineer |
| Band Voyage | Engineering lead + 1 dev, 1 music industry advisor |
Small teams, clear ownership, full autonomy.
2. Weekly Rhythms
Every company follows the same weekly rhythm:
Monday: Team syncs. What happened last week? What's planned this week? Any blockers?
Tuesday-Thursday: Execution. Minimal meetings, maximum building.
Friday: Demos and retrospectives. What shipped? What did we learn?
I join the Monday syncs for each company. That's my primary touchpoint—about 5 hours total across all companies.
3. Metrics Dashboards
Each company has a simple dashboard with 3-5 key metrics:
- DuckDuckSign: Documents signed, new users, conversion rate
- Alignmint: Waitlist signups, demo requests, NPS
- Roladexter: Active users, transcription minutes, retention
I check these daily. If something's off, I dig in. If metrics are healthy, I stay out of the way.
4. Decision Frameworks
Most decisions don't need me. Teams have frameworks for making their own calls:
Reversible decisions: Make them fast, don't ask permission. If it doesn't work, reverse it.
Irreversible decisions: Discuss with me first. These are rare—pricing changes, major pivots, key hires.
Customer decisions: Default to what's best for the customer. If in doubt, ask the customer.
This eliminates 90% of the decisions that would otherwise bottleneck on me.
5. Communication Protocols
Clear communication prevents chaos:
Async by default: Most communication happens in writing. Slack, Notion, email. This creates records and respects time zones.
Sync when necessary: Video calls for complex discussions, brainstorming, or relationship building. But only when async won't work.
Escalation paths: Everyone knows how to reach me urgently if needed. But "urgent" is defined narrowly—customer emergencies, security issues, team crises.
What I Actually Do
My time breaks down roughly like this:
| Activity | Hours/Week | Purpose |
|---|---|---|
| Company syncs | 5 | Stay informed, unblock teams |
| Strategy work | 10 | Long-term planning, new opportunities |
| Recruiting | 5 | Finding great people |
| External | 5 | Investors, partners, press |
| Buffer | 5 | Unexpected issues, deep thinking |
That's a 30-hour week focused on high-leverage activities. The other 50+ hours of "work" happen through the teams.
The Mindset Shifts
From Doer to Enabler
Early in my career, I did everything. Sales, product, engineering, support—whatever needed doing.
Now, my job is to enable others to do those things better than I could. This requires:
- Letting go of control
- Accepting that others will do things differently
- Celebrating team wins, not personal accomplishments
From Urgent to Important
When you're running one company, everything feels urgent. Customer complaint? Drop everything. Bug report? Fix it now. Sales call? Take it immediately.
With multiple companies, you can't respond to every urgent thing. You have to trust teams to handle urgency while you focus on importance:
- Hiring the right people
- Setting the right strategy
- Building the right culture
From Optimization to Satisficing
Perfectionism doesn't scale. You can't optimize every decision across seven companies.
Instead, I aim for "good enough" on most things and "excellent" on a few things. The few things: team, product quality, customer experience. Everything else can be satisficed.
Common Mistakes
Mistake 1: Shared Resources
"We'll have one engineering team serve all companies." This never works. Context switching kills productivity, and no one feels ownership.
Mistake 2: Founder as Bottleneck
"All decisions go through me." This creates a queue that slows everything down. Delegate decisions aggressively.
Mistake 3: Neglecting Culture
"We're too small for culture." Culture happens whether you're intentional or not. Better to shape it deliberately.
Mistake 4: Ignoring Burnout
"I can push through." You can't, not sustainably. Build systems that don't require heroics.
When It Doesn't Work
This model has limits:
Early stage: When a company is pre-product-market-fit, it often needs founder intensity. I was deeply involved in DuckDuckSign's early days before stepping back.
Crisis mode: When something's on fire, I dive in. But fires should be rare if systems are working.
Wrong team: If you don't have the right people, no system saves you. Hiring is the highest-leverage activity.
The Portfolio Advantage
Running multiple companies isn't just manageable—it has advantages:
Diversified risk: Not all bets need to win. Some will fail, and that's okay.
Shared learning: Insights from one company inform others. What works in Alignmint's SEO strategy might apply to DuckDuckSign.
Talent mobility: Great people can move between companies as interests and needs evolve.
Negotiating leverage: Shared infrastructure, vendor relationships, and brand create economies of scale.
Getting Started
If you're considering running multiple ventures:
-
Master one first: Don't start multiple companies until you've built systems that work for one.
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Hire ahead: Bring in people before you're overwhelmed, not after.
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Document everything: Systems only work if they're written down and followed.
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Start small: Add one company at a time. Prove the model before scaling it.
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Protect your time: Your calendar is your strategy. Guard it ruthlessly.
Running multiple companies isn't about working harder. It's about building systems that multiply your impact. The goal is leverage, not hours.