Hi! Welcome to another issue of Force Multipliers, your weekly briefing from Regina Gerbeaux, where Silicon Valley's behind-the-scenes operators get battle-tested frameworks for their toughest challenges, from putting out chaotic fires to managing strong personalities.

Let me tell you about the time Matt Mochary asked me to raise a fund.

I was his Chief of Staff, and Matt trusted me with literally everything. So when he said "OK, go raise a fund," he expected me to just... do it. Like everything else I'd handled for him.

But I said no.

Not because I couldn't figure it out (I probably could have). Not because I was too busy (though I was).

But because raising a fund poorly would tank our reputation and hurt LP returns. This wasn't a "figure it out as you go" situation. This was a "we need someone who actually knows what they're doing" situation.

So we brought in Alex Duff, an incredible specialist who lived and breathed venture capital. And you know what? Best decision we ever made.

That experience taught me something crucial about the generalist vs. specialist decision that I use to this day.

I got a great question from a Force Multipliers reader last week that made me realize we need to talk about this:

This question hits differently when you're drowning in work at 11pm on a Thursday, wondering if you'll ever see the bottom of your task list again. Trust me, I've been there.

But here's what most operators get wrong: they think the answer is about headcount. It's not. It's about knowing the difference between an infrastructure problem and a capacity problem.

The Real Question Isn't "Generalist or Specialist?"

The real question is: Have you actually maxed out your infrastructure first?

Because throwing bodies at problems is what lazy operators do. Smart operators automate first, hire second.

Here's the truth: You should only be thinking about hiring when you've genuinely automated everything possible, cleaned up your workflows, and you're STILL drowning. When it's no longer an infrastructure problem but a genuine "we don't have enough hours in the day" problem.

Once you hit that point, here's how to think about it:

You hire generalists when:

• You're building out your team and need someone who can do a little of everything

• The work requires someone scrappy who can take things from 0 to 1

• You need someone who thrives in autonomous, vague environments

• The mistakes won't be catastrophic (no one's going to jail if they mess up)

You hire specialists when:

• The domain has enough work to keep one person busy full-time

• The stakes for incorrect actions are high

• You need deep expertise more than broad capability

• Getting it wrong could damage your reputation or bottom line

The Operator’s Playbook on Making Generalist Hires

The Uncomfortable Truth About Timing

Most operators wait too long to hire their first generalist. They're drowning in work, becoming the bottleneck, and still convincing themselves they can handle it.

Here's my rule: If you feel suppressed in your role and you've already automated everything possible, it's time.

Not "maybe time." Not "I'll think about it next quarter." Time.

Because here's what happens when you wait too long: You become the bottleneck. Your company's growth stalls because everything has to go through you. And ironically, you become less valuable to the organization because you're too busy doing instead of thinking strategically.

Your Next Action

Take 30 minutes this week and honestly assess where you are:

1. List out everything on your plate that could potentially be delegated

2. Run it through the 5-question reality check above

3. Calculate the actual ROI of bringing someone on

4. Make the call: infrastructure problem or capacity problem?

If it's truly a capacity problem and the math works out, start writing that JD. If not, go back to automating.

The bottom line

Hiring your first generalist isn't about admitting defeat or building a bureaucracy. It's about recognizing when you've genuinely maxed out your leverage and need another pair of hands to multiply your force.

And sometimes, that's exactly what your company needs to get to the next level.

Until next time,

P.S. Still not sure if you should hire a generalist or specialist? Hit reply and tell me your specific situation. I read every email and would love to help you think through it.

Was this newsletter forwarded to you? Are you here for the first time? If so, remember to subscribe below…