A late-stage company might take your $100K and still barely talk to you. Before you write the check, find out how much information comes with it.

"Am I going to lose my money?" leaves half the investment conversation out. For the risk in this deal, how much return should my $100K demand?

A customer who orders is a start. I want to see them keep the product, pay for it, and order again before I call that company proven.

A friend makes $500K in a good month trading stocks. He puts $10M at risk to do it. Other months, he's happy to get his money back. Ask about the capital behind the return.

Raise your hand and say, "I have $100K." The deals will find you. Finding something to invest in is the easy part. Deciding how much risk your money should buy is the work.

Professional management. Cleaner financial controls. Better customers. The logistics business in this case study sold for $28M at an 8X return. No new product. They changed what the company was worth. Full case study: youtu.be/McswUMA20U8

You got a deal on your management team's salary. Now they're a flight risk. Free pizza and beanbags won't keep them when somebody offers real compensation. Pay them so they can't afford to leave. Full video: youtu.be/McswUMA20U8

No cops around. Can you still slow down? A company needs that same discipline. Internal audits. Financial controls. The ability to police itself when nobody's watching. That's worth money to the next buyer. Full video: youtu.be/McswUMA20U8

Everybody wants somebody else's money. Can your management close the quarter on time? Big checks require accurate financial reports. Easy to say. Incredibly hard to do. Full regrading playbook: youtu.be/McswUMA20U8

You know there are no cops on this road. Do you still limit your speed? Same question for a private company. Can it control itself when nobody is there to catch it?

Want a technical moat? A better pitch won't put one in the business. Acquire something that gives you a competitive advantage. Buy the advantage. Then tell the story.

I was on a private jet with a guy who told the pilot to circle the airport so he could finish a chapter of his book. That cost $11,000. That's how people in the deep economy spend money. It's not how they make it.

Over the last few years, I've said no to deal after deal. I was looking for something that fit my buy box. You don't change the box because you're tired of saying no.

The guys who started the company may be the wrong guys to run it. The next buyer wants management with a track record. People the market already knows and respects. That's the first move in regrading a company. Full video: youtu.be/McswUMA20U8

Forget the pitch. Look back two years. Did the company do what it said it would do? The breadcrumbs are everywhere. Your $100K deserves more than another promise about the future. Full traction test: youtu.be/McswUMA20U8

My 1971 240Z is worth $150K. A regular dealership tells me to go away. Bring a Trailer has buyers who understand it. Same car. Different market. Your asset needs a buyer who knows what they're looking at. Full video: youtu.be/McswUMA20U8

I'm not buying Microsoft. I'm buying companies that need the management, reporting, and controls Microsoft already has. That's the opportunity.

Ask for the old board packets. What did management say it would do next quarter and next year? Start with that version of the story.

An ungraded Michael Jordan card starts an argument about price. Get it graded and suddenly buyers can agree on what they're looking at. Same card. Different market.

No forklifts. No ovens. No welding equipment. Just a laptop, a coffee machine, and a phone. What are they building? Better deals.