Entrepreneurship10 min read

Building Four Companies Simultaneously: Systems, Not Superhuman Effort

By Caleb BakOctober 8, 2020

Building Four Companies Simultaneously: Systems, Not Superhuman Effort

I run InfiniDataLabs, HireGecko, serve as COO of UMaxLife, and manage investments through Wisrem Trading. People assume I work 100-hour weeks. The reality? I work 50-60 hours, and the companies run better because of it.

The secret isn't superhuman effort—it's superhuman systems.

The Myth of the Hustling Founder

There's a harmful narrative in entrepreneurship: successful founders work 18-hour days, sleep at the office, and sacrifice everything for their companies. I did that for my first venture. It was miserable, and the company suffered because of it.

Exhausted founders make poor decisions. Burned-out leaders build burned-out teams. Companies that depend on the founder's constant presence don't have businesses—they have expensive hobbies.

"The goal isn't to build a company that needs you every hour of every day. The goal is to build a company that runs beautifully whether you're there or not."

The Four Companies

Let me give you context on what I'm actually running:

InfiniDataLabs - My flagship company. Custom AI and data solutions for enterprises. 45 employees, $12M annual revenue.

HireGecko - AI-powered recruitment platform. 18 employees, growing 200% YoY. Product-focused company with strong product-market fit.

UMaxLife - Mental health analytics platform where I serve as COO. 32 employees. I handle operations and growth strategy.

Wisrem Trading - Investment vehicle managing commodity and real estate portfolios. Data-driven investment decisions across multiple asset classes.

Four very different businesses. Different stages. Different challenges. Different teams.

And I'm not working 160 hours a week.

The System: Decision Frameworks

The key to running multiple companies is having clear frameworks for every recurring decision.

Framework 1: The Decision Matrix

I categorize every decision into four buckets:

Type A: Strategic & Irreversible

  • Examples: Major hires, strategic pivots, large investments
  • **My involvement:** I make these decisions personally
  • **Time allocation:** 20% of my time
  • Type B: Strategic & Reversible

  • Examples: Marketing campaigns, product features, partnerships
  • **My involvement:** Team proposes, I approve or adjust
  • **Time allocation:** 30% of my time
  • Type C: Tactical & Irreversible

  • Examples: Customer contracts, compliance decisions, financial commitments
  • **My involvement:** Clear guidelines, team decides, I review outcomes
  • **Time allocation:** 10% of my time (review only)
  • Type D: Tactical & Reversible

  • Examples: Daily operations, routine processes, standard interactions
  • **My involvement:** None. Team has full authority.
  • **Time allocation:** 0% of my time
  • 80%
    Percentage of decisions I DON'T make

    Most founders get this backwards. They spend 80% of their time on Type D decisions and rush through Type A decisions. That's how you build a company that requires you constantly but never scales.

    Framework 2: The Weekly Operating Rhythm

    Each company operates on a predictable rhythm:

    Monday Morning (1 hour each company):

  • Review key metrics from previous week
  • Identify any red flags
  • Set priorities for the week
  • Wednesday Afternoon (30 min each company):

  • Check in on weekly priorities
  • Unblock any stuck initiatives
  • Adjust if needed
  • Friday End-of-Day (30 min each company):

  • Review week's outcomes
  • Celebrate wins
  • Note learnings
  • Total time: 8 hours per week across four companies for regular operations.

    Everything else happens asynchronously or is delegated completely.

    The Team: Hiring for Autonomy

    You cannot run multiple companies with people who need constant direction. I hire for three things above all else:

    1. Initiative Over Experience

    I'd rather hire someone with 3 years of experience who sees problems and fixes them than someone with 10 years who waits to be told what to do.

    Red flag question: "What should I do about [obviously fixable problem]?"

    Green flag response: "I saw [problem]. I tried [solution A] and [solution B]. Solution B worked better. Here's what I learned."

    2. Communication Over Proximity

    Remote work isn't a perk at my companies—it's a requirement for how I want to operate. This forces everyone to communicate clearly in writing.

    What I need to know:

  • What are you working on?
  • What's blocking you?
  • What do you need from me?
  • What decisions are you making?
  • What I don't need:

  • Daily status updates
  • Asking permission for routine decisions
  • Explanations of how you're spending every hour
  • 3. Ownership Over Execution

    I don't hire executors. I hire owners.

    Executor mindset: "I did what you asked."

    Owner mindset: "Here's the outcome you wanted and three additional improvements I implemented."

    The best hire I ever made was someone who, three months in, proposed eliminating their own position by automating their work. We promoted them to build systems for the whole company.

    The Communication System

    Running multiple companies requires ruthless communication discipline.

    Rule 1: Asynchronous by Default

    99% of communication happens asynchronously. Slack messages, project updates, recorded videos, detailed documents.

    Synchronous meetings are rare and require justification.

    Rule 2: Written Communication is Primary

    If it's not written down, it doesn't exist. Every decision, every discussion, every plan gets documented.

    Benefits:

  • I can catch up on four companies in the morning by reading updates
  • New team members onboard faster with documentation
  • Decisions don't get lost or misremembered
  • I can review and respond on my schedule
  • Rule 3: Meeting Protocols

    When we do meet, meetings have strict protocols:

  • **Pre-read sent 24 hours in advance:** If you're asking for my time, I need context first
  • **Clear decision needed:** Every meeting must end with a decision or action
  • **30 minutes maximum:** If you need more, you haven't prepared enough
  • **Notes shared within 2 hours:** Decisions are documented immediately
  • The Metrics: What I Actually Track

    I can't watch everything, so I watch the right things.

    InfiniDataLabs Metrics

  • Monthly Recurring Revenue (MRR)
  • Customer satisfaction scores
  • Project delivery on-time percentage
  • Employee utilization rate
  • HireGecko Metrics

  • Monthly Active Users (MAU)
  • Placements per month
  • Customer retention rate
  • Net Revenue Retention (NRR)
  • UMaxLife Metrics

  • Platform uptime
  • User engagement metrics
  • Customer acquisition cost (CAC)
  • Customer health scores
  • Wisrem Trading Metrics

  • Portfolio returns vs. benchmarks
  • Risk-adjusted performance
  • Cash flow from properties
  • Commodity position P&L
  • Each company has a dashboard I review every Monday. If metrics are green, I don't dig deeper. If metrics are yellow or red, I investigate.

    One dashboard per company, five metrics max. If you need more metrics to feel comfortable, you don't trust your team enough.

    Time Allocation: The Reality

    Here's how my typical week breaks down:

    InfiniDataLabs (20 hours):

  • Strategic client meetings
  • New business development
  • Team leadership and coaching
  • Technology roadmap planning
  • HireGecko (12 hours):

  • Product strategy
  • Key partnership discussions
  • Fundraising activities
  • Weekly leadership check-ins
  • UMaxLife (8 hours):

  • Operations review
  • Growth strategy
  • Cross-functional alignment
  • Key hiring decisions
  • Wisrem Trading (8 hours):

  • Portfolio review and rebalancing
  • New opportunity evaluation
  • Property management oversight
  • Market analysis
  • Administrative/Shared (4 hours):

  • Email and Slack
  • Cross-company learnings
  • Personal development
  • Total: 52 hours per week

    Notice what's NOT on that list:

  • Micromanaging daily operations
  • Sitting in routine meetings
  • Reviewing every decision
  • Being available 24/7
  • What Enables This to Work

    1. Strong Leadership Teams

    Each company has a capable leader running day-to-day operations:

  • InfiniDataLabs: VP of Engineering and VP of Client Success
  • HireGecko: Head of Product and Head of Sales
  • UMaxLife: CEO
  • Wisrem: Investment Manager and Property Manager
  • I'm the founder, but I'm not the daily operator.

    2. Clear Company Strategy

    Each company has a documented 3-year strategy that everyone understands. Daily decisions align with that strategy without needing my input.

    When someone asks "Should we do X?" the answer comes from "Does X move us toward our 3-year goals?" Not from me.

    3. Shared Operating Principles

    All my companies operate on the same principles:

  • Asynchronous communication first
  • Documentation over meetings
  • Ownership over execution
  • Metrics-driven decisions
  • Customer obsession
  • This means I can apply learnings across companies and don't need to context-switch completely.

    4. Deliberately Different Domains

    My companies are in different industries deliberately. This forces me to hire experts and trust them. I can't micromanage an industry I don't know intimately.

    This is a feature, not a bug.

    The Mistakes I Made (So You Don't Have To)

    Mistake 1: Trying to Do Everything

    When I started my second company while running my first, I tried to maintain the same level of involvement in both. I burned out in three months and both companies suffered.

    The fix: Hired strong operators for the first company, stepped back, and focused on the second until it was stable.

    Mistake 2: Inconsistent Systems

    Each company had different tools, different processes, different communication styles. Context switching was exhausting.

    The fix: Standardized core systems across all companies. Same project management tools, same communication platform, same meeting structures.

    Mistake 3: Not Documenting Enough

    I thought I could keep it all in my head. I couldn't. Decisions got lost, people got confused, and I became a bottleneck.

    The fix: Everything gets written down. If it's not documented, it doesn't exist.

    Mistake 4: Hiring for Skills Over Fit

    I hired experienced people who needed constant direction over less experienced people with initiative and autonomy.

    The fix: Now I hire for autonomy first, skills second. Skills can be taught. Initiative can't.

    When This Approach DOESN'T Work

    This isn't for everyone. Running multiple companies this way requires:

    1. Capital to hire great people: You can't do this bootstrapped in the early stages

    2. High trust tolerance: If micromanaging makes you comfortable, this will be painful

    3. Comfort with imperfection: Things won't be done exactly how you'd do them. That's okay.

    4. Strong industry networks: You need to hire people better than you in specialized areas

    5. Clear personal boundaries: Without discipline, four companies will consume your life

    The Biggest Benefit: Better Companies

    Here's the surprising outcome: My companies perform better because I run multiple companies.

    Why?

  • I'm forced to build scalable systems from day one
  • I hire better leaders because I can't be the daily leader
  • I make better strategic decisions because I'm not in the weeds
  • I spot patterns across industries that insiders miss
  • I maintain perspective instead of getting tunnel vision
  • The companies are stronger because they don't depend on me for everything.

    Your Action Plan

    If you're thinking about running multiple ventures:

    Start with one: Get your first company to a point where it runs without you for a week. Then a month. Then a quarter.

    Build systems first: Don't start a second company until your first has clear systems, strong leaders, and documented processes.

    Hire for autonomy: Every new hire should increase the company's ability to operate without you, not decrease it.

    Document everything: If it's not written down, it doesn't scale.

    Start small with the second: Don't try to run two mature companies. Run one mature company and one startup.

    The goal isn't to work less. It's to multiply your impact without multiplying your hours.


    *The best companies are those that run beautifully whether the founder is there or not. Build systems, not dependencies.*

    Tags

    EntrepreneurshipSystems ThinkingStartup ManagementDelegationLeadership
    CB

    About Caleb Bak

    Serial entrepreneur, founder & CEO of InfiniDataLabs and HireGecko, COO of UMaxLife, and managing partner at Wisrem LLC. Building intelligent solutions that transform businesses across AI, recruitment, healthcare, and investment markets.

    Learn more about Caleb →

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