Category: Entrepreneurship

Help Businesses Prepare for the Delivery Economy

Smarter people than I have observed that delivery and direct-to-consumer companies are going to thrive in the aftermath of this pandemic. It’s the platforms and at-scale logistics companies that are going to really own it: Walmart, Amazon, etc, as well as Instacart, Doordash, and Uber Eats. But what about all of the businesses (and business […]

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Trying to Bring About Corporate Change?

This post comes in response to a question sent to me by a friend: I’m about to take on leading my company’s new innovation incubator.We’ve been stuck in “status quo” land for a few too many years and nowwe’re dipping our toes into the waters of investing in new markets andmore efficient work strategies. My […]

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The Companionship That Outlasts Coworking

If companies could have veteran’s organizations, my last company’s would be a thriving one. Tonight I gathered together with some current employees and past employees (I’m now one of those salty old-timers) as we bowled, played games, drank, ate, and caught up. The magical thing is that it felt to me like we were all […]

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Give Your Customers Some of Their Freedom Back

Joy. Enthusiasm. Freedom. These aren’t what you expect to feel after a long day at work. You probably don’t expect them from most businesses. And you definitely don’t expect to feel them when you book an Uber ride home. But then, you haven’t been in MY card for an Uber ride. Tonight I took a […]

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De-Platform Yourself

A new phenomenon in the Internet age is that of “deplatforming” in which a person, organization, or movement gets booted off of an online platform. Sometimes de-platforming happens for good reasons (a bank refusing to serve a drug cartel). Sometimes it happens for bad reasons (YouTube’s algorithm arbitrarily bans your cat videos). That’s not what […]

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Begin Sternly, Proceed Softly: What Startups Can Learn from Machiavelli

Remember that high school English teacher who scared the hell out of you for the first few months, then became the coolest teacher ever for the next four years? You probably ended up liking her more than you liked the teacher who tried too hard to be liked, then became a tyrant when “niceness” failed. […]

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Maybe Companies Should Be Smaller

I was scrolling through Twitter when I came across this thought-provoking suggestion: Imagine if everyone went on a sort of “strike” all at once: don’t work with or for anyone you think is sleazy or unfair. Don’t do any job you think is pointless or immoral. Just actually listen to your personal judgment. Would everyone […]

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If You Want Companies to Innovate at Scale, Plan for Companies to Screw Up

The larger a community gets, the harder it is for that community to drive things together in the same direction. Scaling pretty much guarantees division and miscommunication (as well as a few sneaky evildoers hiding among good people). It’s hard enough for a family of 7. Yet many of us care about living in communities […]

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Tell a Company “Thank You”

If you’re a kind and grateful kind of person, you probably know how satisfying it feels to give someone a genuine and specific “thank you.” Most people don’t say it, so most people don’t hear it. So when most people do hear a “thank you”, it’s like a drink of cold water in the desert. […]

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What Startup Marketers Can Learn from Peter Thiel’s Zero To One Principle

To create outsized value, you must choose to do the things that create the most marginal value: value created minus effort paid. I think one of the most promising mental models is Peter Thiel’s idea of zero to one innovation, as expressed in Zero To One. He argues that most wealth is created by companies […]

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It Really Is Just About the Will To Work In the End

You know what the Internet needs? Another post about how hard work and execution is more important than ideas. But it’s true, and I feel a need to repeat this from my own experience. I work in a company that wants to grow fast, and faster. When we don’t grow like we should, the debate […]

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You Will Always See More Problems with Your Product Than Your Critics

After a few years in a small company, I’ve been through my fair share of user complaints, issues, bugs, service failures. When I first found out about problems with our product (I was young and naive) I would be a lot more freaked out. Over time, I’ve come to accept that problems (and fixing them) […]

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Build a Culture Open to Debate

Our company is not shy about debating. If there is an issue, it usually gets raised – and publicly. “I’m not sure about this subject line.” “We should rework the copy on this page of the website.” “This dashboard functionality doesn’t do what it promises.” These critiques come from every area of the company – […]

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Evolve Your Interviews To Protect Your Company

Interviews are sort of like antibiotics. Yes, they’re useful to bring great new people into your team. But it’s also important to use interviews to keep the bad eggs from spoiling your culture and productivity. And as with any antiobiotic-germ relationship, the germs are constantly developing resistance. You can’t just ask the same old interview questions anymore. Your candidates are reading […]

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A Brand Awareness Hack for Your Next Conference

How do you stand out as a vendor when you’re walking a conference floor full of companies trying to sell their stuff? Over my few years of startup marketing experience I’ve started to pick up the habit of seeing unconventional opportunities for brand exposure that don’t cost much – if anything. At one event, that […]

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Want To Learn About Entrepreneurship? Shop with Solopreneurs

Solopreneur, noun. A person who sets up and runs a business on their own. … ‘With the exception of solopreneurs, small businesses are run by more than just the boss.’ – Oxford English Dictionary This morning I visited a windshield specialist (let’s call him Mike) operating out of a quirkily appointed but professional nook in a parking […]

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How To Create Even When You’re Busy

Think you’re too busy to learn? That problem has already been solved. If you don’t know about the glories of audiobooks and podcasts by now, you’ve missed out on years of learning you could have done while walking the dog or making food for the family. But how about creativity? You don’t have to look far […]

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Experience Vendors: Pop-Up Street Micro-Business Ideas

One day on Atlanta’s Beltline walking path I encountered a young chap typing away on a typewriter, offering free poems (or else very cheap ones) to passersby. On other days, I’ve seen folks selling popsicles and even coconuts. All of this has made me wonder whether I could open a micro-business like these, too. With […]

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Demystify a Job Before You Hire For It

Mystification is the root of all kinds of evil when it comes to hiring. Say you’re building a marketing team from scratch. Say you also need to hire people who can do event marketing, partner marketing, email marketing, digital marketing, content marketing, AND public relations – all key functions. Who you hire for these positions could determine the […]

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Can Jacks of All Trades Become Great?

As part of my Charity:Water campaign, I’m writing blog posts for people who contribute $25 or more to bring clean water to 23 people. You have a word/topic/question you want me to riff on? I’ll (probably) write it. One donor asked me to write about whether jacks of all trades could become really great.  Interested in supporting […]

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Ownership vs. Fiefdoms

Ownership can save any project or company. Fiefdoms will kill both. But the difference is often fine and hard to distinguish. Ownership is the ownership of responsibility for a given task or set of tasks.Just like a house will keep better with a homeowner to tend it, so will any project. Bob might “own” the email-based customer support efforts […]

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The Call to Entrepreneurship and Our Excuses

Think starting up your dream business is a daunting task? Imagine going straight from being on vacation to starting up a complex refugee rescue mission under the nose of the Nazis – with no prior experience and no preparation. That was 29 year-old stock broker Nicholas Winton’s entrepreneurial story. From 1938 to 1939, Winton successfully […]

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The 10 Startup Rites of Passage

“The best start-ups might be considered slightly less extreme kinds of cults.” – Peter Thiel  Every year, hundreds of thousands of people in the United States join small, unvetted mysterious organizations that require extreme lifestyles and promise untold riches. Are there new cults sweeping the nation? Are people joining boy bands? Nope. They’re joining high-growth startups. When you really think […]

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Team? Family? Squad? Finding the Best Analogy for Coworkership

How should you think about your relationships with your coworkers? Everyone has their favorite metaphor. Some people think of employees as “family.” This has the advantage of creating (if done right) an. But it also isn’t fully honest. Unlike in families, dismissal/firing is a part of the life of a workplace. Some people have responded […]

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Coming Home to the Office

“At dawn, when you have trouble getting out of bed, tell yourself: ‘I have to go to work — as a human being. What do I have to complain of, if I’m going to do what I was born for — the things I was brought into the world to do? Or is this what I was […]

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Create (and Keep) a Volunteer Culture

Some of my favorite memories of working at my company include the chores that “weren’t my job”: moving boxes, ordering lunch, restocking the fridge, doing A/Vs setup, doing customer support, even sitting at the front desk. We now have some wonderful people who take care of things like these – but we went through a long […]

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Great Branding Starts With Great Hiring

So, you want a brand and a company that everyone will love? It’s counterintuitive, but you shouldn’t start by working on your brand or working on your company. You should start by working on your hiring and your team. In the final analysis, “brands” and “companies” are not things that exist. They’re ideas. And the idea […]

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A Defense of Absurd Silicon Valley Startup S***

Scooters at the office? Lightsaber battles? Champagne and fries? Starting work at 10 AM? We’ve had it all at my company. These are the strange trappings of the Silicon Valley startup culture that’s arisen in the last decade. They have their problems. They can be excessive. They can distract from the real work at hand. They can be a waste of money. […]

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Work Like You’re Already Fired

What if you only had two weeks left to work at your company? What if you knew you were leaving, or if you knew you were going to be fired? But what if you still really wanted to make an impact? Assuming you’re a value creator, you’d do a few things differently. 1. You would […]

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Startup Scaling Is the Most Addictive Game

The rules change constantly. Sometimes there are no rules. Sometimes there are so many rules you have to go rogue. There are dozens and hundreds of characters with unique personalities and motivations. You don’t know which ones are friends. What works at one level doesn’t work at another. You constantly have to re-learn the game. If you […]

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