Building Two Companies Instead Of A 9-5

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Hey Fearless Friend!

Today on Stay Fearless or Die Trying😀 

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Let’s be honest: running two companies at once is a little unhinged. It’s also thrilling, clarifying, and—if you build the right system—surprisingly sustainable. But make no mistake: this isn’t a productivity hack; it’s a lifestyle choice with real costs. Here’s what’s actually crazy about it—and what founders should know before jumping in.

This is the wildest chapter of my career yet. As I sit at a coffee shop and write this newsletter while taking a break from an excel sheet of numbers for Chief Swag Officer, I can tell you I have absolutely no idea what I’m doing at any given time.

The difference between you and me is that I don’t feel scared of not knowing, because at some point I will know. Everything I do in my business life is based solely on the expectation I have that I will be successful.

You’re not waiting on the “right” moment, you’re waiting on a series of events to unfold to get you one step closer. This whole mentality that you’re waiting on your moment isn’t necessarily true: it’s something you see on social media, but it takes every successful person almost 10 years to become the “overnight success” you’re seeing.

What founders should know before choosing the “two-company” life:

1) Make it legal, clean, and boring (on purpose)

• Separate entities, bank accounts, cap tables, and accounting.

• Clear IP assignment and employment agreements so there’s no “who owns what” drama.

• If you have investors, disclose your split and put it in writing.

2) Design your calendar like an operating system

• Company-by-day works: Mon/Wed = Company A, Tue/Thu = Company B, Fri = CEO day (finances, hiring, strategy, thinking).

• No-interruption blocks (90–120 minutes) for deep work.

• Escalation lane: one emergency channel per company with strict rules on what counts as “urgent.”

3) Give each company one non-negotiable metric

• A single North Star per company (e.g., weekly revenue, active users, gross margin).

• Review every Friday: what moved, why, and the one lever for next week.

4) Install real owners (or don’t do it)

• Each company needs a day-to-day lead (GM/Head of Ops) with budget authority.

• You operate as Owner/Coach, not Player/Everywhere.

5) Set “kill switches” before you need them

Define in advance when you’ll pause one company to save both:

• Cash runway < 3 months

• Retention or margin below a pre-set floor

• Founder health red-zone (sleep < 6h avg, chronic exhaustion, missed family commitments)

6) Share systems, not sloppiness

• Reuse playbooks (hiring scorecards, onboarding, content calendars).

• Standardize tools (bookkeeping, payroll, CRM) but keep separate instances and clean data boundaries.

7) Price your time like a CFO

• Track your founder hourly value (FHV). If a task is below it, delegate or automate.

• Weekly “stop-doing” list. Ruthless is kind.

8) Guard your energy, not just your time

• Sleep is a revenue strategy. So is a workout. So is a weekly full offline block.

• Context switching is costly—design for monotasking.

9) Communication: fewer lanes, faster loops

• Two companies = two Slack workspaces, two email domains, two status updates.

• Investors get a short, rhythmic update (bullets, one metric, one risk, one ask).

Would you run two companies at once, or am I crazy!?

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Stay fearless or die trying,

Alexa

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