1. The best business is one where you’re getting paid for your thoughts

“. . . where someone has decided that your wisdom is so worthy that they're just going to give you hundreds of millions of dollars for it. These businesses require no capital. They're hugely cash flow accretive.”

Getting paid for your thoughts also has the added benefits of getting to meet super interesting people, gaining equity exposure through investments, and your learnings and experience compound over time.

Success in this arena is mostly brand/reputation building. An individual writing online or a consulting business just starting out isn’t a smash hit - proof of work has to accrue over time.

2. Look for opportunities where the incentives are in your favor

When asked about “the perfect investment”, Giffon notes that it is probably one where you really don’t even need to speak to anyone or do any rigorous business diligence, you simply need to understand the stakeholder incentives and why the deal fell in your lap.

“Do you really need to know that much about buying a business if the guy is getting divorced or there's some tax law change or some other exogenous catalysts that you can just tell. I mean this comes back to the people, then you sit down with them and it pains them to be selling the business. That's a great deal. I'm probably going to do that deal just from that fact alone.”

This seems to be a core investing thesis for Giffon, who laid out multiple investment scenarios in which the driver was, at it’s core, misaligned incentives (VC $$ in a slow-growth, overvalued company, undesirable assets in large acquisitions)

3. Understand your edge

Jeremy often asks investors, "what makes you great? what makes you better than everyone else?" and surprisingly receives very few concrete answers.

If you don’t know what your secret sauce is, what you bring that makes you better than the next guy, how can you properly compete?

4. Keep it Simple (but not simplistic)

When Giffon first started buying companies, he would build spreadsheets & ask esoteric questions that wouldn’t actually be a factor in whether or not the business succeeded.

He now prefers simple questions and napkin math. “How do you make money?” “Why do people buy from you and no your competitor?” “What does your business do?”

Really simple questions that most would be too insecure to ask will help you get to the core of the business. No more math than what fits on a napkin.

5. Spend more time thinking about how to spend your time

Most of us go through life putting up with the things we do. We do that because we don’t really know what it is we want, and we haven’t taken the time to seriously think about it.

Uncovering yourself; figuring out what gives you energy and what drains your energy can be a brutal process, but it might also be the highest leverage use of your time.

If you spend 6 months really trying to understand how you want to spend the rest of your life, that’s 6 months well spent.

6. Envy as a barometer for personal happiness

The ability to witness other's success and feel joy (or nothing) rather than envy, is a good indication that you're in a healthy space.

Undermining others accomplishments comes from a place of insecurity.