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Years ago, I was having ice cream with my wife on a hot summer night and I overheard a group of 16-year-olds talking about how one of them went to work with his dad. I remember him saying:

“I went to his office and it was so boring. Everything was bright lights and pale colors. If I had to be in an office all day I’d make it just like my bedroom and enjoy hanging out there.”

I distinctly remember looking at my wife and saying, “That kid has it figured out. I spend 14 hours a day in a room I don’t want to be in with a job that I love.” I vowed one day to change that.

That was ten years ago. It apparently took a really long time for me to act on this one, but I finally did, and I have to say – the kid knew what was up.

Love Your Workplace

In ...

Question: What is the No. 1 thing I should avoid when making my first-ever pitch and why?

The answers below are provided by members of FounderSociety, an invitation-only organization comprised of ambitious startup founders and business owners.

Not Communicating Your Value Proposition

Don’t lose focus of the overall goal of communicating your value proposition. If the prospect fails to see it, you’ll never get them sold no matter how hard you tried or how much effort went into your sales deck.

— Steven Newlon
SYN3RGY Creative Group

Winging It

The best pitches look like they’re off-the-cuff, but they’re not. Smooth delivery and confidence comes from a lot of practice. I’ve heard so many people say, “I speak best when it’s not rehearsed” or “I...

The past few years have seen an explosion of podcasts — it seems like everyone wants to get in on the audio. And startup founders (many of whom have probably been listening to podcasts since they started in the early aughts) are no exception! But how do you know what to listen to in this vast sea of startup podcasts?

Don’t worry — we have you covered. Here are the top 20 best startup podcasts as we head into 2020. Grab your noise cancelling earphones — and get listening.

1. Startup Therapy

Hosted by Startups.com founders and serial entrepreneurs Wil Schroter and Ryan Rutan, Startup Therapy is an inside perspective on issues startup founders really care about. From what to expect in your first year after launching to how to deal with the e...

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 managers work hard ...

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 wrote about h...

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 ...