“Things I wish I’d known sooner.” An incomplete list, mostly applied to business / career.

My target audience is my younger self. Some of all of it may not work for you. It barely works for me.

You will grow old and die waiting for permission. Forgiveness is easier to get if you master the sad puppy face.

A surprising number of problems can be solved by finding someone who’s solved them before and paying them for advice.

Yes, pay them. Advice is worth what you pay for it.

Work for free before you work for cheap.

Strive mightily to never work for free.

People die of exposure.

Charge more.

A business partnership is very much like a marriage. It requires similar levels of trust.

The thing that holds you back might be your superpower in another context.

There’s no such thing as an easy enterprise sale. I sell “keep more of your money” (about as simple a value proposition as it gets) and it’s still deeply nuanced.

Getting it wrong and apologizing sometimes is better than not having gotten it wrong at all.

You can’t punch down; only up.

People read less than you’d think.

Quick example: my second child is arriving in three months. I’ll be taking two months off for parental leave near the end of the year.

Most people don’t know the weight their words can carry. An offhand comment can devastate people for years.

Be kind.

Assume your secrets will all get out eventually. The people you gossip about will find out. Act accordingly.

Assume you’ll have a relationship with people that outlasts whatever jobs you both have at the time. Take the long view.

Most people’s version of success kinda sucks.

Integrity counts for a lot. If you compromise yours, make sure it’s worth it; you’ll never get it back.

Don’t reduce the price without reducing the scope.

Not every lead is a good lead. Not every customer should remain a customer.

Spend a week doing their job and you’ll never dismiss “mere” accountants/marketers/salespeople again.

Honestly, you shouldn’t have in the first place.

Engineering is a surprisingly small part of success / failure in business.

If you don’t have someone around with whom you vehemently disagree, fix that. It forces you to articulate why you believe as you do.

Amounts of money that would change your entire life are pocket change to large companies.

With so many things (talent, advice, etc) you'll pay fair market rate for what you get--whether you want to or not.

"Act as if." If you have no idea how to present a proposal to a sophisticated buyer, you'd better learn before you do it. This is where that "pay for advice" thing kicks in.

Your buyer is going to use certain phrases to describe their pain. Those phrases should find their way into your proposal to fix that pain.

It's counter-intuitive, but it's easier to get work by being more specific instead of less. "I'm an AWS architect" is okay. "I fix the horrifying AWS bill" triggers a "hey that's me!" response.

"...for insurance companies in Spokane" or whatnot would be even better. Oops.

An awful lot of problems VC backed companies face melt away if you're profitable.

You won't be the next Uber, but on balance would you really want to be?

You won't succeed without people doing you favors.

Most of those you can only pay forward. Make sure you do. If someone asks you for help, you help them.

Corollary: People often ask for advice when what they really want is validation. Confuse the two at your own peril.

Businesses cost a staggering amount of money to run.

Hiring is hard. Anyone who claims to have cracked the mystery is selling something. Best case scenario, it's a book; the worse answer is "they're abusing candidates, knowingly or not."

Almost nothing is a zero-sum game. For you to win, someone else doesn't have to lose.

Everyone has advantages and disadvantages. Some folks have more of one than the other. Work with what you've got. "Comparison is the thief of joy."

You offer to do a thing for $5,000. The most the client can offer is $500 right now.

It's easier to turn "I'll help you out for free for a time" into a $5K project later; you'll never 10x someone who's paying a 90% discounted rate. https://twitter.com/CyborgTribe/status/1275641480518881280?s=20

For an awful lot of us, the honest answer to 'why did you start your own company' is 'because I didn't have a second option.'

I have no idea what I'm going to be doing in 1, 5, 10 years from now.

But I know I'm going to need an audience to tell all about it.

You can get all kinds of good advice from well meaning people on the internet.

Legal and accounting advice, you want from a professional you pay.

If you ever find yourself saying "I could make twice as much if I quit this job and got hired somewhere else," realize that you're either a fool who's wrong, or a fool for staying put. Either way, nobody looks good expressing that sentiment.

An awful lot of people who've never run a business themselves sure do have a lot of ideas about how you should run yours. Be polite. You once sounded a lot like they do.

"Help me understand why" is a way better start to a sentence than "why don't you."

Never charge by the hour. Fixed fee only, and you get that fee based upon the value you provide, *NOT* the cost of providing it.

I repeat, never charge by the hour. Unless you're an attorney there's going to be a hard cap as to how much you can realistically charge an hour. That's generally less than FAANG will pay a senior engineer. Go work there; it's easier.

"I'm going to go independent!" Expect to spend 70% of your time on client development, 30% on doing what you actually set out to do. Unless you enjoy 100 hour weeks, DO NOT CHARGE BY THE HOUR.

Find an expensive problem you know how to fix, and sell that.

If you find yourself talking to someone who talks about *HOW* you do what you do instead of *WHAT* you do, they are not your buyer.

To wit, my clients don't care if I solve AWS bills with machine learning, Excel, or an abacus. They care about the outcome.

Engineers are generally terrible customers. They frequently mistake their time for free, so the build vs. buy conversation takes an unnatural turn.

Even if you win the debate, their signing authority caps out around $50.

There are two paths to take; mine (cost optimization) is the lesser of the two. There's a theoretical max of "100% of the AWS bill" that I can save.

Speeding GTM, or the right feature at the right time can return 10x that. THAT gets the board's attention in way I don't.

Things that work for one business don't work for another.

I don't partner with any vendor in the cloud space; that means I can be objective in a way few can.

"I partner with no vendors" in the security space makes me sound like a dangerous anarchist with an ego problem.

Don't treat every deal like it's the last one you'll ever see.

"Can you help us with our Azure bill?" The loss of focus means the correct answer here is "No, sorry."

If "no, sorry" is too difficult to say, the same sentiment can be expressed with a hilariously high price.

Be careful with hilariously high prices that nobody will ever pay.

There's at least one aspect of my media business that exists because that hilariously high price wasn't high enough, so now I'm stuck with it.

No, I'm not mentioning which.

Clearly delineate everything that's sponsored. The FTC requires it, for one.

For the record, I've never sold a sponsored tweet. This Twitter account is mine personally. Y'all are stuck with me.

"It's lonely at the top" is a truism not because so few people make it there, but because running a business with staff is a rarefied situation that looks awesome from the outside until you actually have to DO it.

It's isolating. Find people you can talk to about it.

One of the hardest parts of business is managing your own psychology. One of the best parts of partnering with @mike_julian last year is that I've got someone I can vent to about everything that's currently on fire.

And there're always things on fire. Welcome to business.

Diversity and inclusion are hard.

Most things worth pursuing are.

One of the biggest changes @mike_julian and I had to adjust to once we hired staff was communication.

Our common shorthand is to pick apart the problems with the other's work; ignore the good parts, let's focus on the things to fix.

This presents as "Hello, I'm a huge asshole."

As of this week the Duckbill Group is ten employees (if you include the two of us).

I manage none of them. My role is to be public and self promotional; that's incompatible with my view of what management needs to be.

An awful lot of decisions feel momentous at the time but don't actually matter in the grand scheme of things.

Make a choice and roll with it. Most can be fixed if you get it wrong anyway.

Everyone is a storyteller. A lot of them need to learn to be more effective at it.

Same story with sales.

"Running a business is risky compared to being an employee."

Is it really? I used to think that way.

Today no client of ours is more than 20% of revenue. How many people have to sign off on firing an employee?

Non-hourly T&M is a good step in the right direction--but it still suffers from the problem of paying for time instead of value. There is an upper bound. https://twitter.com/tqbf/status/1275656625907523586?s=20

The ultimate goal is more profit, not more revenue. You have a cost; you want to make money on top of that cost.

"What's my cost?" Peg it to an FTE salary at $unicorn of your choice. You want to make more than that; you are a business, after all.

If you can solve a problem that's causing $100k worth of pain in eight hours, do you charge a day rate ($300*8=$2400)?

You can absolutely charge $10k for that and no one would bat an eye. No one is going to pay you $10k/day for that, but they'll gladly pay $10k for the problem to go away.

I'm not saying that my path is right for everyone; there are days I've wished mightily that I could "fit in" at a company.

I can't. If you can, good for you! Do it!

I just got mighty tired of getting fired all the time.

I set out to find an expensive problem I knew how to solve. Kinda hard to do that if you can’t demonstrate how expensive it is. :-) https://twitter.com/mike_hasarms/status/1275659906453028869?s=20