The Questions You Can't Ask When You're Running a $15M Business


In 2019, my company hit $15M in revenue. Inc. 5000. 742% growth rate. Press coverage. The whole nine yards.

From the outside, I was crushing it.

Inside, I was drowning in questions I couldn't ask anyone:

Should I take institutional capital or stay bootstrapped?

Is my leadership team capable of scaling to $50M?

What decisions am I making today that are killing my exit valuation?

My team had opinions but no experience at this scale. My advisors had frameworks but no scars. My successful friends had built $5M businesses—not $15M+ companies facing completely different strategic decisions.

I was profoundly alone in the questions that mattered most.

If you're running a fast-growing business, you probably know this feeling. And here's what I learned: that isolation isn't just uncomfortable—it's expensive.

The Questions No One Could Answer

Here's what kept me up at night as we scaled woom USA:

Questions about capital:

Should we raise institutional capital or stay bootstrapped? My team had strong opinions. My advisors had theories. But none of them were risking their life savings. None of them had built a business past $15M and faced this exact inflection point.

If we take capital, what do we give up? What do we gain? I needed someone who'd actually been through it—not someone who'd read about it.

Questions about my leadership team:

Is this the right team to scale us from $15M to $50M? To $100M? I couldn't ask them—they were the team. But I was losing sleep wondering if loyalty was clouding my judgment about capability.

How do I have the "you've grown this far, but..." conversation with executives who've been with me from the beginning? No HR manual prepares you for that.

Questions about my financial model:

Is our economic model actually built for scale—or just optimized for survival? Our margins looked good, but I didn't know if we were leaving millions on the table because we'd never transformed the fundamentals.

What financial levers could 10x our growth without 10x-ing our team? I was stuck thinking linearly: more revenue = more people. But I knew there had to be a better way.

Questions about exits and enterprise value:

How do I prepare for an exit I'm not sure I even want? My friends hadn't built businesses they could sell. My accountant knew tax strategy, not transition strategy.

What decisions am I making TODAY that are killing my valuation—and I don't even know it? I'd heard horror stories of owners leaving 30-40% of value on the table because they didn't set up their business for an exit years in advance.

Questions about my own role:

How do I get OUT of the business so I can work ON the business? I was still the bottleneck on too many decisions. I knew I needed to scale myself, but I didn't know how.

Why No One Could Help

Here's what made this so isolating:

My team had opinions but no experience at this scale. They'd never built past $15M. They'd never raised institutional capital. They'd never exited. They were incredible at execution, but they couldn't answer strategic questions they'd never faced.

My board and advisors had frameworks and theories, but they weren't owner-operators. They didn't have their entire net worth and identity tied to the decisions. The risk wasn't personal for them.

My "successful" friends had built great businesses—to $3M, $5M, maybe $8M. But $15M to $50M is a completely different game. Different capital structure. Different leadership requirements. Different exit considerations. They meant well, but they didn't have the context.

Every major decision felt like a coin flip because I had no one to gut-check it with who'd actually been here.

The Real Cost of Isolation

This wasn't just lonely—it was expensive.

In real dollars:

  • Slower decisions meant missed opportunities. Markets moved while I deliberated.
  • Wrong decisions cost us 6-12 months of momentum (and seven figures in some cases).
  • I left money on the table because I didn't know which levers to pull.

In opportunity cost:

  • How much faster could we have scaled with the right roadmap?
  • How much more enterprise value could we have built with the right financial model?
  • How many mistakes could I have avoided if someone had said, "I tried that—here's what actually happened"?

In personal cost:

  • Analysis paralysis on decisions that required confidence.
  • Second-guessing myself constantly because I had no peer validation.
  • The weight of carrying it all alone while everyone assumed I had it figured out.
  • Stress that bled into every other area of my life—my marriage, my parenting, my health.

And while I was navigating these impossible business questions, my personal life was imploding. Divorce. Co-parenting stress. Health deteriorating. The isolation compounded across every area of my life.

But the business isolation was the core issue. Because when you're making multi-million dollar decisions with no one to pressure-test them against, everything else feels heavier.

What Changed Everything

In 2021, I joined Birthing of Giants—a cohort of 15 CEOs running $7M-$50M businesses who were in the exact same territory.

Not people who'd "been there" 10 years ago and forgotten what it feels like.

Not people who were still at $3M looking up at me.

Not advisors with frameworks but no scars.

People who were RIGHT HERE, RIGHT NOW.

And for the first time, I could say:

"I don't know if I should take this capital"

And hear back: "Here's what happened when I did it—and what I wish I'd known."

Not theory. Not a case study. Real experience from someone with skin in the game.

I could say: "I think I need to replace my Director of Operations, but he's been with me from the beginning"

And hear: "I just went through this. Here's how I handled it. Here's what I'd do differently. Here's the conversation framework I used."

I could say: "My financial model feels like it's holding us back, but I can't see how to transform it"

And hear: "Let me show you the model we implemented last year. It changed everything."

What My Cohort Actually Gave Me

1. Relevant context I couldn't get anywhere else:

These weren't generic "best practices." These were:

  • "Here's what worked at $15M that stopped working at $25M"
  • "Here's the capital structure mistake I made that cost me $5M in my exit"
  • "Here's the financial model shift that freed up 20 hours a week of my time"
  • "Here's the leadership framework that helped me scale from 30 to 100 employees without losing culture"

2. Faster, better decisions:

Instead of taking 3 months to make a decision, I could pressure-test it with my cohort in 3 hours.

Instead of learning through expensive trial-and-error, I could learn from their expensive trial-and-error.

3. Accountability that actually moved the needle:

When you tell 15 CEOs you're going to do something, you do it. Not because they're policing you—but because they're invested in your success. They call you out when you're making excuses (because they know all the excuses—they've used them).

4. A board of advisors who actually get it:

My cohort became my informal board. When I faced the decision to merge woom USA with the European operations, I had 15 CEOs helping me think through the deal structure, integration challenges, leadership transition, and personal implications.

5. The confidence to make big moves:

The isolation wasn't just lonely—it made me tentative. Every major decision felt risky because I had no validation.

My cohort gave me the confidence to make bold capital decisions, have difficult leadership conversations, transform our financial model, navigate a complex merger, and step into a bigger CEO role than I thought I was ready for.

Not because they told me what to do—but because they helped me see clearly what I already knew.

Why I'm Building This in Austin/San Antonio

Because I know this isolation intimately—and I know what changes when you find your people.

I'm now a Regional Cohort Leader for Birthing of Giants, building what I needed in 2019: a selective community of 12-15 business owners in Austin/San Antonio running $5M-$100M companies who become each other's trusted circle.

Not a networking group. Not a monthly lunch. Not a social club.

A 2-year structured program with quarterly full-day sessions, expert speakers, a proven curriculum used by 1,100+ successful entrepreneurs, and built-in accountability.

A cohort that becomes your informal board of advisors.

The Questions You're Carrying

Here's what I want you to think about:

What questions are you carrying that you can't ask anyone?

What decisions are you making alone that shouldn't be made alone?

What's the cost of figuring it out by yourself for another year?

The best leaders don't have all the answers. They have the right people to pressure-test their thinking with.

You don't have to carry it alone.

If you're running a $5M-$100M business and this resonates, I'd love to connect. Not a sales pitch—just a conversation about what's possible when you find your people at your exact stage.

—Mathias

P.S. What questions are YOU carrying that you can't ask anyone?


Mathias Ihlenfeld

My Mission: To inspire others to become the best version of themselves—through business and personal reflections, tools, and practices I actually use. This is for founders, leaders, and anyone creating a life with clarity, balance, and meaning.

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