In boxing, you get knocked out if you don’t do something counterintuitive (step with your rear foot first).

Smart, capable people become first time CEOs/managers and end up knocked out because they ONLY do intuitive things.

10 essential counter-intuitive CEO skills: 1. Eliminate sympathy and double down on empathy.

Your employees will have problems, but these can’t become your problems and they are not yours to solve.

You should, however, empathize with the challenge of performing at an elite level (which you need) while life happens.

Winter is coming.

Many VC backed startups funded in 2020/2021 are going to die in the next 12 months.

Most don’t realize it yet.

My companies survived 2001 and 2009 and I learned a few things.

How not to die: 1. You need a plan.

A path-to-profitably plan is based on:

1. No new sales beyond existing pace - then discounted by 25%

2. Existing margins

3. No less than 3 months cash in bank at lowest point.

4. Cash flow, not accrual accounting.

5. No new funding.

I've searched for a climate change "silver bullet" for more than a decade: A globally scalable, tech-enabled solution.

I've finally found it: A way to remove all the carbon from the sky for no net cost.

I'm starting a company to do it. Let me take you down the rabbit hole: Humans have a rich history of amending our soil with carbon.

Over 2,500 years ago, Amazonian tribes buried charcoal with food scraps. It transformed marginal soil into incredibly rich, fertile soil.

The carbon they buried (as charcoal) is still there today.

Today’s my 44th birthday. 🎉🎉🎉

My memo to my 24 year old self: Most “bad” things that happen to you are not as important as they feel at the time.

You can make more money, fall in love again, or start a new company.

You can’t recover time or health lost stressing about what went wrong.

This whole free $10,000 if you were totally cool with taking a bunch of debt and didn’t rush to pay it back…

Some hot takes for every like until I get tired of it: 1. This is a shot across the bow on the college educated vs non-college educated voting divide.

The Dems have lost the hearts of all non-college educated folks for a generation.

The days of raising money on a pitch deck are over.

Even the earliest angel investors want to see traction.

But how do you get traction with no money?

Here are five examples: Hardware Business:

Buy off-the-shelf hardware that approximates what you will build.

Sell it as a bundled product/service to the target audience at a markup. (Or at worst, a small loss)

I think a lot about asymmetric risk, and that extends to my health.

There are certain conditions like aneurysms that have no symptoms but then kill you suddenly.

So, as a healthy 43 year old, I went in for a full body MRI.

What I learned amazed me… I ended up here because I met one of Prenuvo’s team members on my Calendly calls earlier this year.

They kindly offered to comp my first session if I would write about it.

@prenuvo told me that 1 out of 20 of their patients has a life saving diagnosis.

I’ve struck 7 figure deals with public companies, raised $250 million, bought 15 companies and sold one.

In that process, I learned some valuable lessons.

Here are 5 fundamentals for getting a deal done.

+ 5 key legal areas to get right.

The real art of the deal: #1 - Move fast.

Time kills most deals. Excitement fades, life happens, jobs change, deal fatigue sets in.

Line up your counsel (legal, technical, accounting) ahead of time. Set strict deadlines.

At least 50% of startup stock options are now worthless.

Most employees don’t know it yet.

Here’s what you should know about stock options if you work at a startup: For stock options to be granted without tax consequences, they need to “strike” at current fair market value.

When a company does a big financing round, that value goes way up.

Company does a 409a valuation. Usually common stock values about 30% of new financing price.

Week 1. Lock down the site reliability engineering team with substantial retention bonuses. You don’t want your platform crashing while you reorganize.

Get control of all basic financial functions with your own person as interim CFO if possible. Week 2. Build a lean org chart from scratch. I would say you want 2,000 heads when done. Half will be new faces, so you are looking at 7,000 layoffs.

This will immediately flip the computer substantially cash flow positive, giving you time to build its new future.

A friend called me last week, torn up. She had to fire a co-founder.

Here’s what I told her…

Firing is the worst part of entrepreneurship.

But it is also the most essential.

Nobody taught this in business school, so I wrote a manual.

How/why to fire with love: If you are even considering firing, you have already made the decision.

You just haven’t accepted it yet.

You keep coming up with excuses: Maybe a different role or a performance improvement plan will help.

Truth is, the employee is playing on the wrong team.

As an entrepreneur, I have had amazing Board Members and terrible ones.

Then I became one. But there was no manual, so I made a lot of expensive mistakes.

After 1,000+ board meetings, I decided to write one.

Here’s Good Director/Bad Director: Good Director knows they only have two jobs:

1. Hire and compensate the right CEO.
2. Approve the budget and strategic plan.

Bad Director thinks their main job is to provide good ideas. They think the board’s job is to micro-manage the CEO.

Have you ever made a bad decision that cost you $100 million?

I have.

It gives me a chip on my shoulder that drives me today.

I’m a bit nervous to share the story on Twitter, but here goes: My first entrepreneurial success came in my early 20’s from Better World Books.

We bootstrapped from $40 (yes, forty dollars) in startup costs to tens of millions of revenue.

We were the first “pure play” online used bookseller. First textbooks, then all books.

From our finance lead (for our digital businesses), who is in Ukraine, as is her team:
 
“Thank you, we really appreciate the support. The team is safe and keeps working.
 
As to how you can help – two things remain intact: Pressure your officials – state representatives, senators, whomever you can reach, in US and overseas – we need detrimental sanctions, particularly banning swift; we need anti-missile weapons, and we need no-fly zone over Ukraine declared by NATO

Most startup pitches I see suck.

The products are good.

What is missing is the story.

If you are raising money, the story has to come first.

Here is the framework I have used to build compelling stories that have raised over $200 million for my own startups: 1. Why now?

Something in the world just changed and that’s what created opportunity.

Otherwise, there would be lots of people doing it already.

e.g. “AI is now cheap enough that we can embed it into a stapler. Meet the world’s first smart stapler.”

We are taught we should save for a down payment when we are young.

I believe you should rent and save that down payment money to buy a business.

Here’s why: It takes a lot of work to save $100k or $200k from working a day job.

This is the minimum down payment in most expensive metro areas.

If you take that and buy a house, you are locked in to an expensive life.

You have fixed mortgage payments and you probably can’t relocate.

Some Twitter anons seem to think building a business that cash flows > $250k is like winning the lottery right after you are struck by lightning.

Would love anyone to reply with an anon biz they know that earns in excess of this. I will start (we don’t own these): Humane snake traps sold on the Internet.

Roughly three years ago I quit.

I quit working for a company I co-founded and grew to 1 million customers.

I was 40, unemployed with two kids.

Since, I bought 13 companies, started 2, had more fun (and grew faster) than ever in my career.

A short defense of quitting: We are taught from a young age that “winners never quit and quitters never win.”

I think this is terrible advice.

Winners constantly evaluate where to allocate their time, money and attention.

When necessary, they make a hard decision to make a change.

The paradox of entrepreneurship is that it only takes one: One investor to be the difference between running out of money and living to fight another day.

Here it is! 2021 shareholder letter for Enduring Ventures Inc.

We are a long term holding company dedicated to building abundance for our employees and shareholders through ownership in diversified, cash-flowing businesses.

Full letter in the 🧵

Here's our progress to date: 2/ Most key of all was strict price discipline and creative deal structuring

/ We have a very differentiated model in the "business buying" business.

/ Private equity's weird incentives are problems for their investors and for those who sell to them.

SBA loans are the cheat code to American capitalism.

They allow anyone to transform overnight from an employee to an owner.

I am not just saying this. I used SBA to buy $2 million of cash flow for $300,000 down as Enduring Ventures’ second major deal.

Here’s how it worked: First, an overview of SBA:

You can borrow up to $5 million for a business or $10 million if it is real estate heavy.

You can go even larger with some banks (I know one) that will lend “peri passu”.

That said, if you are not an experienced business manager and not wealthy…