Entrepreneurs think “the start” is the hard part…getting from $0 to $1M.

It’s not.

The real graveyard is the $2M - $20M stretch known as “No Man’s Land.” That’s where margins shrink, sales stall, and founders burn out. And the answer isn’t to just “work harder.”

I know, because I tried to out-hustle my way through this phase with 80-hour weeks and missed family dinners, soccer games, and dance recitals.

Spoiler: it didn’t work.

What does work is a 5-step process we call “The 2 to 20 Playbook” that we now use across our $200M portfolio to scale companies without chewing up the founder in the process.

Here’s how it works:

Step 1: Double Your ACV

Just like an explorer stockpiles food before a long journey, you need to stockpile margin and cash so you have the necessary fuel to scale.

Here are three (3) ways to do it:

  • Raise Prices. Most founders undercharge. Even a 10–15% bump drops straight to the bottom line.

  • Add a “10X for 10%” Upsell. A premium option (done-for-you, concierge, skip-the-line). If just 10% of buyers say yes, you can double ACV instantly.

  • Run an Invisible Offer Survey. Email customers: “What’s one thing you wish we offered that we don’t?” Half the time they’ll ask for something you already sell. That’s free money.

Set a clear goal: Double your ACV within 12 months.

Step 2: Hire Your First True Functional Leader

At $2M, you’re still duct-taping marketing and fulfillment together yourself. This has to stop if you’re going to bridge the $2M to $20M gap.

Ask yourself: If my customers doubled tomorrow, what would break?

  • If fulfillment breaks → you have a supply constraint. Hire a Head of Fulfillment, Product, or Client Services.

  • If nothing breaks (and you’d celebrate) → you have a demand constraint. Hire a senior Marketing or Sales leader.

Here’s the filter: Your new hire:

  • MUST be more experienced than you at the job, and…

  • MUST bring a playbook for solving the constraint beyond just “Hire more people and spend more money.” Demand a 30/60/90 plan before you hire. If it’s vague or just about adding headcount, run.

This hire should pay for themselves within 90 days. If they can’t, they’re not a leader…they’re an arsonist.

Step 3: Upgrade from YouOS to a Real Operating System

Right now your business is running on YouOS (your brain + your hustle). That won’t scale.

Here’s a simple checklist for upgrading your OS:

  • Document the critical 20% of workflows. Not everything…just the 6 - 10 processes that are most likely to break.

  • Build a company scorecard that mirrors the customer journey. No vanity metrics. From first touch → sale → fulfillment → renewal…every step of the customer journey needs a KPI. (Also, every metric MUST have an OWNER.)

  • Install accountability rhythms. Quarterly execution planning + weekly scorecard check-in meetings keep your team aligned and accountable to doing what they said they would do.

Without these systems, everything still runs on you. With these systems, your business can finally run without you.

Step 4: Optimize Margins and Pay Yourself First

The ultimate sign of a healthy business isn’t sales, growth, or even customer satisfaction. The ultimate sign of a healthy business is the company’s ability to pay its best people well while still investing in growth.

TranslationL If you aren’t paying yourself, your model is broken. Period.

Here are your targets:

  • 30% operating margins

  • Fair salary + regular distributions for you and your stakeholders

Why?

  • It validates that the business model is scalable.

  • It ensures you can afford to hire the talent you need.

  • It ends the martyrdom trap (working for “someday” while starving your family today).

The day I gave myself a raise was the day I knew my business could scale, and that’s what gave me the confidence to make the investments needed to actually scale.

Step 5: Upgrade Leadership & Multiply the Winners

To get from $2M to $20M, you need leaders who’ve been there. So it’s at this point that you need to audit every leader on your team and ask:

“Has this person scaled from $2M to $20M before?”

  • If yes → double down and multiply what’s working.

  • If no → you have 3 options:

    • Coach them with a clear growth timeline.

    • Top them by hiring an exec over them.

    • Replace them if neither works.

It’s not harsh…it’s reality.

Loyalty doesn’t scale. Competence does.

Once you have the right leaders in place, you can expand channels, widen your product line, or raise capital with confidence.

The takeaway: What got you to $2M won’t get you to $20M. But if you follow this playbook in sequence: double ACV, hiring the right functional leader, upgrade your OS, optimize your margins, and uplevel your team…

…you’ll cross the chasm with more cash, more freedom, and a lot more fun.

⚡ Action Step: Pick one of these five steps and schedule 30 minutes this week to work on it. Whether it’s drafting an Invisible Offer Survey, mapping your 80/20 critical workflows, or sketching out your first scorecard, take the first small step now…before the chaos of next week drags you back in.

P.S. If you’re stuck in “No Man’s Land” and want help building your own “2 to 20 Playbook,” that’s what we do. Schedule a free “Scale Session” today.

Quick Hits

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