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Why are Founders often so lonely? It's a combination of things.

First, unlike most other jobs, Founders often don't have a lot of relatable peers in their close-knit group. Most people can sit at lunch and complain about their jobs and get a bunch of nods.

Us Founders often explain what we're going through and get the "thousand-yard stare" from someone wondering how to get out of the conversation.

What do Founders do in this case?

The first thing they do is to find other Founders to meet up with.

The one amazing thing about Founders, by the way, is that they immediately tend to connect with and appreciate other Founders.

It's amazing.

Every Founder understands what it means to be staring into the abyss daily, and how those feelings are...

One of the sayings I hear from talented managers in product development is, “good enough never is.” It’s inspirational, always calling the team to try harder and do better. It works to undermine excuses for poor or shoddy work. And, most importantly, it helps team members develop the courage to stand up for these values in stressful situations. Especially in teams that are managing by objectives (or OKRs), the pressure to deliver is intense. Under such pressure, the temptation to cut corners, to quit prematurely, or to hand off shoddy work to another department is overwhelming. It requires courage to stand up and say: “this work is simply not good enough. Sure, we could get away with it, but that’s not how we work.” Good m...

Every year, we’ll hear people declare that SEO is dead. Well known entrepreneur Gary Vaynerchuk has declared that its been dying for quite some time. It might be changing, but it’s not dying. Not even close.

Wouldn’t we all love to go back to the late 1990s and early 2000s – a time when simply stuffing keywords into a website’s meta tags, footers and CSS files was enough to guarantee high rankings in the search engines? Not to mention getting paid big money for these simple hacks.

As search engine algorithms have become more sophisticated, most of these tricks have died out. You’ve probably already heard the tagline “SEO is dead”, but for some reason the mindset still persists that figuring out the latest on-page tweaks is the key to natura...

At one time, only the corporate elite could afford to collect and crunch millions of data points to optimize their businesses. But with the advent of big data as a service, companies of all sizes now have the chance to take part in the big data revolution.

Although the need for data isn’t new, the amount of information and the type of intelligence it can provide looks starkly different than it did even a few years ago. In fact, the same amount of data influx that was achieved over the past 50 years is now achieved every two days.

If you’re serious about data, you need a way to store, manage, and analyze millions of numbers that will point your business in the right direction. As your company expands, your data stockpile will also grow expon...

Last week I got a call from Patrick an ex-student I hadn’t heard from for 8 years. He was now the CEO of a company and wanted to talk about what he admitted was a “first world” problem. Over breakfast he got me up to date on his life since school (two non-CEO roles in startups), but he wanted to talk about his third startup – the one he and two co-founders had started.

“We’re at 70 people, and we’ll do $40 million in revenue this year and should get to cash flow breakeven this quarter.” It sounded like he was living the dream. I was trying to figure out why we were meeting. But then he told me all about the tough decisions, pivots and firing his best friend he had to do to get to where he was. He had been through heck and back.

“I made it t...

1. You will never take a “real” vacation again.

I am 7 years in and I have come to accept that it is not possible for me to take a “movie vacation” — ya know on a beachfront bungalow with no internet connection, remote from the working world…. And let’s be real — to an entrepreneur that simply doesn’t actually sound fun or relaxing at all. My ideal lifestyle is to be semi-connected on vacation. I’m a phone call/text message away and I will choose when to respond to emails. That may be the extent of my ability to fully “vacation”…and I’m honestly ok with that. Just as I sleep better when my kids are under my roof, I also sleep better when I’m accessible to my business.

2. You will decrease your friendship pool.

Where do most people find the...

I started angel investing almost by accident, which sounds strange to say. Who “accidentally” invests tens of thousands of dollars into highly speculative ventures? Well, I did.

A friend introduced me to Clayton Christopher who was raising money for his new liquor company Deep Eddy. Their first product, a sweet tea vodka, was amazing and he was an experienced entrepreneur, so I went in.

Investing was an exciting, interesting process. Then the company took off, and I got to tell everyone I know that I invested in that new vodka that everyone in Austin was drinking. Winning is the ultimate intoxicant, and from there, I was hooked.

I started investing in companies left and right. I became a huge cheerleader for angel investing. I w...

More often than not, what we avoid saying to investors is as valuable as what we do say.

With our best intentions, we often shoot ourselves in the foot making lofty assumptions or declarations that investors hear all the time and just start shaking their heads.

Let's avoid that.

These are conservative forecasts

The moment we open ourselves up to saying our estimates are "conservative" we risk the conversation pointing to whether our assumptions are actually "conservative", "aggressive" or just "wild-ass guesses."

All estimates are guesses.

Let's avoid giving them a label at all, and instead say "These estimates are based on our best assumptions across our entire business." Investors would rather know the assumptions are based on what we ...

The cap table is a ledger of who owns stock in our company. If you and I are the only owners of the company, there are exactly two entries in the cap table.

Easy peasy.

But as the company grows, and we start handing stock out to more people, the accuracy of the cap table starts to become really important

It's easy now...when does it get complicated?

The moment we start handing stock out to more people than ourselves.

At that point, we start to run into keeping records of not only who we've allocated stock to, but who we may be taking it back from (former employees who may not have exercised their stock options for example).

The constant changes within the cap table start to become a bit more complex, and having an accurate ledger become...

There’s a popular misconception amongst first-time entrepreneurs that sharing an idea without signing a non-disclosure agreement (NDA) will lead to some version of The Social Network, where Mark Zuckerberg, played by Jesse Eisenberg, steals the Facebook idea and becomes a billionaire.

The mythology sounds horrifying, but the reality is much different.

In short – investors don’t sign NDAs. They won’t sign your NDA. Asking them to will make you look like you don’t know what you’re doing, and there are a few reasons for that.

No One Wants Your Idea

You may have the world’s most amazing idea. It may be a complete pile of rubbish. Either way, it’s not about ideas.

Investors want entrepreneurs, not ideas. Anyone can come up with a great idea, but...