Office Hours: The 10 Questions We Hear Most From Founders

One of the things I enjoy most about working with founders is that the questions are rarely just about the thing they’re asking.

“Should I raise now?” is usually also about runway, growth, valuation, and whether the company is ready.

“Can I afford to hire someone?” is usually about priorities, cash, and what the company actually needs next.

“Do I need a board?” is often really a question about how to build the right kind of accountability around the company.

After enough founder conversations, you start to notice patterns.

The same questions come up again and again.

So I wanted to answer ten of them in one place.

These aren’t rules. Every company is different. But they’re the questions I find myself asking founders most often, and the way I think about them.

1. When should I start fundraising?

Earlier than you think.

Not necessarily earlier than you need the money, but earlier than the moment when you desperately need the money.

A fundraise takes time. There are investor conversations, diligence, meetings, negotiations, and plenty of things you can’t control.

The mistake I see is waiting until the runway is almost gone before starting.

Instead, work backward from your cash position.

How much runway do you have?

What milestones do you need to reach before the next raise?

How long will it realistically take to raise?

What happens if it takes longer than expected?

Fundraising is much easier when you’re raising from a position of planning rather than urgency.

2. How much runway should I have?

There’s no magic number that works for every company.

What matters is whether you understand your runway and what you’re going to accomplish with it.

Don’t just know your current cash balance.

Know your monthly burn.

Know what’s committed.

Know what’s discretionary.

Know how hiring changes your burn.

And know what happens under different scenarios.

I like founders to be able to answer a simple question:

“If nothing changes, when do we run out of cash?”

Then ask the more important question:

“What do we need to accomplish before then?”

Runway isn’t just a number.

It’s time to create evidence.

3. When should I hire?

When the company has a problem that actually requires another person to solve it.

That sounds obvious, but hiring can easily become a proxy for growth.

You feel busy, so you hire.

Revenue is growing, so you hire.

Everyone else has a bigger team, so you hire.

Instead, ask:

What problem will this person solve?

What work will they take off the founder’s plate?

What will they make possible that isn’t possible today?

And what happens if you wait three months?

Sometimes the answer is that you need the hire.

Sometimes the answer is that you need to fix the process first.

Headcount is one of the biggest recurring expenses in an early-stage company, so every hire should have a clear reason behind it.

4. What financials should I actually be looking at?

More than just revenue.

At a minimum, I want founders to understand:

• Cash balance
• Monthly burn
• Runway
• Revenue
• Gross margin
• Customer growth
• Customer retention
• Accounts receivable
• Major upcoming expenses

The exact metrics will depend on the business.

The important thing is that you can look at the numbers and understand what changed and why.

Financial visibility isn’t about building the world’s most complicated model.

It’s about being able to answer:

What is happening in my business right now?

And:

What is likely to happen if I don’t change anything?

You shouldn’t need a finance team to tell you whether the business is moving in the right direction.

5. How do I know what I should be tracking?

Start with the decisions you need to make.

If you’re trying to understand whether customers are sticking around, track retention.

If you’re trying to understand whether sales are becoming repeatable, track your pipeline, conversion, sales cycle, and source of customers.

If you’re trying to understand whether you can afford to hire, track burn and runway.

If you’re trying to understand whether the product is creating value, look at usage and customer behavior.

The goal isn’t to track everything.

It’s to track the things that help you make better decisions.

I’ve seen founders spend hours building dashboards full of numbers they never actually use.

A smaller set of useful metrics is usually much more valuable.

6. How often should I communicate with investors?

More consistently than you probably think.

Investor communication shouldn’t only happen when you’re raising money or when something goes wrong.

A good investor update gives people a clear view of the business:

What happened?

What went well?

What didn’t?

What are you focused on next?

Where do you need help?

You don’t need to make every update sound positive.

In fact, I think investors get more value from founders who are direct about what isn’t working.

Trust comes from having a clear picture of reality, not from making every month look perfect.

7. What should I be telling my board?

The same principle applies.

Your board doesn’t need a polished version of the company.

They need to understand what’s actually happening so they can help you make decisions.

Come prepared with the numbers, but spend time on the decisions.

Where are you stuck?

What changed?

What are you considering?

What are the tradeoffs?

What do you need from the board?

A board meeting shouldn’t just be a presentation of what happened last month.

It should help you think about what happens next.

8. How do I know if I’m ready to raise?

This is one of the hardest questions to answer because “ready” doesn’t mean the same thing for every company.

Instead of asking whether you feel ready, ask whether you have a compelling reason to raise.

What are you raising?

Why now?

What has the company proven?

What still needs to be proven?

What will the capital allow you to accomplish?

And why is this the right amount?

You don’t need to have everything figured out before raising.

But you should be able to explain what the money is going to change.

A fundraise should have a purpose beyond extending the runway.

9. What should I do when things aren’t going according to plan?

First, don’t hide from the numbers.

If revenue is below plan, say it.

If a customer segment isn’t working, understand why.

If a hire isn’t working out, deal with it.

If your original growth assumption was wrong, update the assumption.

The worst thing you can do is continue making decisions based on a plan that the business has already disproven.

Early-stage companies are constantly learning.

Your plan is a hypothesis.

The job isn’t to prove that you were right when you wrote it.

The job is to learn quickly enough to make the next decision better.

10. What should I be focused on right now?

This might be the question underneath all the others.

There is always more to do.

More customers to talk to.

More features to build.

More people to hire.

More investors to meet.

More partnerships to explore.

More metrics to track.

But early-stage companies rarely have a shortage of things they could do.

They have a shortage of time and resources to do all of them.

So I come back to three questions:

What matters most right now?

What is the biggest risk to the business?

What do we need to learn next?

The answers will change.

That’s the point.

A final thought

There is no universal playbook for building a company.

The right fundraising strategy depends on the stage of the business.

The right hire depends on the problem you’re trying to solve.

The right metrics depend on the business model.

The right board depends on what the company needs.

But I do think there’s one common thread:

You can’t make good decisions if you don’t have a clear view of what’s actually happening.

That’s why financial visibility, customer behavior, runway, and a small set of meaningful metrics matter so much.

Not because founders need more dashboards.

Because founders need better information.

And better information leads to better decisions.

That’s ultimately what Office Hours is about: the questions that come up when you’re actually running the company, not just talking about it.

We’ll keep adding to this list as those questions change.

If there’s something you’re trying to figure out right now, it may be the next one.