In short: An interview with Robert Nikic on the questions he asks founders, the red flags he watches for and the traits that predict whether a company will last.
Founders often ask Robert to look at their business. We asked him what he's actually looking for. The conversation has been edited for length.
When a founder asks for your advice, what's the first thing you look at?
Cash. Always cash.
Not revenue. Not growth. Not the story. How much money is in the bank, how much goes out every month and how long until it runs out. Everything else depends on that number. A founder who doesn't know it off the top of their head has a problem bigger than whatever they came to ask me about.
And after cash?
Customers. Who's actually paying, how much, how often and why. I want to know the top ten customers by name and what each one is worth. I want to know who left last year and why.
A lot of founders can tell me about their product for an hour. Far fewer can tell me why their best customer chose them over the alternative. The second answer tells me much more.
What questions do you ask the founder directly?
A handful, and I always ask them the same way.
What would kill this company in the next twelve months. Who's the one person you'd be in real trouble without. What have you been avoiding. What's the decision you know you need to make and haven't. If you had to cut 20% of costs tomorrow, where would it come from.
How they answer matters as much as what they answer. A founder who can answer quickly has been thinking about it. A founder who gets defensive is usually avoiding something.
What are the red flags?
They blame everyone else. The market, the customers, the team, the economy. Every company faces those. The founders who make it look for what they can control.
They don't know their numbers. Not every number. But margin, cash, customer count, churn. If those are fuzzy, everything else is too.
They've stopped talking to customers. It happens as companies grow. It's always dangerous.
Everything goes through them. A founder who can't name one decision their team makes without them has built a company that can't grow past them.
They're in love with the idea, not the business. Ideas are cheap. Businesses are ideas that make money. If the founder can't tell me how the idea makes money, we have work to do.
They need it to work too much. This one's subtle. A founder who's put everything on the line, savings, house, relationships, sometimes makes desperate decisions. I want them to be committed, not cornered.
And the green flags?
They're honest about what's broken. If you walk me straight to the worst part of the business, I trust everything else you tell me.
They move fast after bad news. Every company gets bad news. The question is how long it takes them to act on it.
Customers love them, and can say why. Not "they're nice." Something specific the company does better than anyone.
They hire people better than themselves. Insecure founders hire people who won't challenge them. Strong founders hire people who will.
They've failed before and can talk about it. I'm not looking for perfect track records. I'm looking for people who learned something from the last thing that went wrong.
How do you tell the difference between a founder who's struggling and one who's failing?
Struggling founders know exactly what's wrong and are working on it. Failing founders either don't know or won't say.
I've sat with founders whose businesses were in terrible shape, months of cash left, a big customer gone, a product that wasn't working, and I wasn't worried, because they could walk me through the problem, the options and what they were going to try first. And I've sat with founders whose numbers looked fine on the surface, and I was very worried, because every question got a vague answer.
The numbers tell you where a company is. The founder tells you where it's going.
What do you look at in the team?
Whether anyone besides the founder can explain the business. I'll often ask two or three people on the team the same questions I asked the founder. What's the biggest risk. Who's the best customer. What's not working.
If the answers match, the company has a shared picture of reality. If they're completely different, the founder has a communication problem that's going to get worse as the company grows.
I also watch how people talk about the founder when the founder isn't in the room. Respect is easy to see. So is fear.
Do you care about the idea at all?
Of course. But less than founders think.
I've watched brilliant ideas fail because the founder couldn't execute, and very ordinary ideas turn into great companies because the founder was relentless about customers and cash. Execution beats ideas almost every time.
What's the most common mistake you see?
Growing before the business works.
Founders get one good month, then hire, spend and expand as if every month will be like that. Then the next month is average, and suddenly they've got costs they can't cover. Make the business work on a small scale first. Then grow it.
How do you deliver hard advice?
Straight. Kindly, but straight.
A founder who asks for my advice deserves the truth, not a pep talk. If the business has a problem, I'll say so. If the plan won't work, I'll say why. I'd rather they hear it from me in a conversation than from the market in a crisis.
But I always come with a path. Here's the problem. Here's what I'd do. Here's what to watch.
Is there a founder you won't advise?
One who wants me to tell them they're right. I'm not useful to them. Anyone can find someone to agree with them.
And anyone who's misleading customers. I won't help a business that only works because people don't understand what they're buying.
What do the founders who succeed have in common?
Three things, mostly.
They know their numbers. They talk to customers constantly. And they keep going after things go wrong, without pretending they didn't.
None of that is about talent or luck. All of it can be learned.
What do you want founders to take from this?
That the questions I ask aren't secret. Ask them of yourself. Know your cash. Know your customers. Name what you're avoiding. Do that every month, and you won't need me nearly as much.
Related reading
- The five principles Robert Nikic builds by
- The seven things that break in a company's second year
- Robert Nikic's biography
Robert Nikic is an entrepreneur, TEDx speaker and Advisory Council Chair at Reseated Councils (United Nations SDG 8 & 9). He writes about what he has seen build and break companies, and about the rules that decide whether small businesses get a fair shot. Read his writing on Medium, the Open Doors newsletter on LinkedIn and daily posts on X.
