The First Big Mistake From 3 Entrepreneurs

Entrepreneurs look back on the blooper they thought would kill their company.

Sandy Chilewich
Founder and creative director, Chilewich

“Back in 2000, when I was just starting, I emailed a buyer at Bloomingdale’s, pitching my place mats. And I don’t know if placemats just wasn’t in my computer’s dictionary, but each time I typed that, it changed to placentas. I didn’t notice and sent it. So I wrote this buyer a lengthy email about how great my placentas were, and how many colors my placentas came in, and how durable my placentas are. I sounded like a madwoman. I never heard back from that buyer, but Bloomingdale’s is now one of our biggest customers.”

Jason Horvath
Cofounder, Uhuru Design

“After 10 years of growing slowly and deliberately, in 2013 we got a $500,000 investment in growth capital and did some marketing, and the following year we sold $10 million. Then we lost focus. We decided to launch an interior design department as well as a jewelry line — a total vanity project — and hired more than 50 additional employees. Sure, we had sold $10 million, but then we spent $10 million, and we entered the next year with very little cash. Growth flatlined — we lost $1.5 million in six months. We had to pull back, lay off some great employees and shut down projects. But now we know what we’re good at and how to manage growth.”

Nathan Bond
Cofounder and CEO, Rifle Paper Co.

“My wife, Anna, and I launched our stationery company in 2009, just in time for the holidays. We had no background in this space and had never worked with a printer. We thought we could send them a file and the product would arrive in perfect shape. But what came back was totally unusable. Even after multiple production attempts, our cards came back with ink smears all over them. We had to make it work, though, so we erased the errors by hand for hours — sitting in a room, in a cloud of eraser shavings! We learned a lot, including how naïve we were.”

Some Strategies for Influencing the Affluent

So you have a product or service that caters to the rich. The clients you want are ultra-wealthy, extremely busy and pretty much untouchable. While every business faces gatekeepers of some sort, those who sell to the affluent face impenetrable fortresses of staffers, handlers and security teams, who make it their job to keep people away from their bosses.

Reach beyond your grasp.
So what do you do if the person you wish to do business with is simply inaccessible? One option is to follow protocol and go through the lines of defenses, pitching your product or service to layers upon layers of decision makers. That could take years. The other option is to create a strategy for influencing the people you wish to work with: the uber-rich, ultra-wealthy, untouchable millionaires and billionaires.

Here are four simple strategies to influencing the affluent:

Open your Rolodex.
Michael Carucci, a Boston-based luxury real estate broker who only deals in multi-million dollar homes, says his secret to influencing the affluent is that he does much more than sell real estate, he opens his rolodex to clients long after the deal is done. Michael has helped his high net worth clients get children into elite schools, get their books and products on national television programs, and obtain impossible to come by red carpet tickets. He says even the affluent need access to hard to get people and things, and he’s created a reputation for delivering that.

Interview them.
It’s going to take a very long time for you to get past the myriad of gatekeepers if you reach out and try to sell something. Instead, try reaching out and asking your ultra-rich potential client if you can interview her for a blog, company newsletter, or other type of periodical. I’ve interviewed more than 300 high net worth business tycoons, athletes, and celebrities. I use tools like the premium membership on LinkedIn to contact them directly. At first contact, I don’t ask for business; I don’t try to sell; I simply ask for an appointment to interview them for an article. The interview is my access, and from there I build long term relationships which often result in business.

Influence their influence.
Shanna Dickerson of Blue Sky Luxury Concierge offers concierge services and event planning and promotion for elite clients around the country, including Richard Branson. How did she score the crème-de-la-crème of clients, Richard Branson? Easy, she was already doing business with someone who influences Branson, and she asked for an introduction. It’s a lot easier to get someone’s ear when you get introduced through someone they trust.

Hang where they hang.
So you may not be able to afford a house in a gated community or a private jet sharing membership, but there are other places the ultra-wealthy hang out. A good place to find them is at country clubs, sports clubs, high-end gyms, and charity events and galas. Furthermore, if you have two hours to kill, instead of booting up your computer at the local coffee shop, make yourself comfy in a corner nook near the bar at the swanky five star hotel, where your chances of running into a potential new affluent client increases by tenfold. It’s much easier to create conversations and get appointments when the people you are trying to influence consider you one of them.

Volunteer or join a board.
Some of the most valuable relationships I’ve made with high net worth friends all started with a passion for a charitable initiative. Find a charitable cause you are passionate about and dig in deeply through volunteering and/or board membership. Non-profits tend to attract people from all economic strata who are passionate about the cause. If you are targeting a particular affluent client, find out what causes he is passionate about and get involved.

How To Busting Some Myths of Entrepreneurship

The entrepreneurial world has always been about challenging the status quo and questioning conventional wisdom in search of new and better ways of doing things. That’s what gave rise, in one way or another, to every great American company. After all, if you’re just going to follow the pack and do what everyone else is doing, you may as well just go out and get a job working for someone else.

Today, however, there’s a pervasive and nearly deafening mantra insisting that each and every one of you should quit your job and become an entrepreneur. The social collective says that every day you wait brings you closer to a life of poverty and regret.

But that’s simply not true. The idea that you can’t have a fulfilling career, be remarkably happy, and even get rich working for someone else is perhaps the most ludicrous, disingenuous, and irresponsible myth I’ve ever heard.

Don’t get me wrong: Entrepreneurship can be incredibly rewarding. Starting your own business may be the best decision you ever make—but it’s not for everyone. There’s a lot to consider before you take the plunge, starting with a few myths that are very much in need of exposure.

Myth 1: Entrepreneurship is the only way to get rich.
This is a complete fabrication. Granted, the richest people in America are mostly entrepreneurs or members of entrepreneurial families, and half of America’s millionaires are self-employed. But that doesn’t mean they were always self-employed. Many of them worked for companies before striking out on their own.

Then there’s the other half of America’s millionaires who are not self-employed. Hundreds of companies such as Microsoft, Intel, Google, Apple, and Facebook created hundreds of thousands of millionaires. The truth is, there’s no data or logic to support the premise that any given person has a better chance of making more money or getting rich by being self-employed. And the notion that it’s a simple either-or proposition is a fallacy. You can do both.

Myth 2: Follow your passion or a cause, not the money.
This is another myth born of oversimplification. Some people discover what they love to do, make a living at it, and find fulfillment. Others do what they’re good at and achieve financial success, and that frees them to pursue their passion. Still others pursue a passion or a cause with no market, go broke, and wind up having to do work they don’t enjoy to make ends meet.

While you’ll probably have a better chance of being happy and successful if you enjoy what you do for a living, there are lots of other factors that determine whether you can pull it off. Passion alone won’t pay the bills. Passion and money are both important. You shouldn’t choose one or the other.

Myth 3: Entrepreneurship is more fulfilling and will make you happier.
Just about everyone enjoys doing great work they can be proud of. And you can do that working for a big company, a small company, or your own company. Fulfillment has absolutely nothing to do with business ownership. If you want to manage, lead, or run a business, you’re better off learning the ropes in a good company before starting your own.

And the last time I checked, the question of what makes a person happy is pretty subjective. Most people are actually happier without the headaches, risks, burdens, hurdles, and uncertainty of having their own company. A lot of people worry too much about what the popular crowd says they should be doing. I think that’s what’s making everyone feel guilty and less happy … but it shouldn’t.

Myth 4: Entrepreneurs have more freedom, less stress, and no bosses.
If you run your own business, there’s a good chance you work 24/7 and wear all sorts of hats you’re not necessarily comfortable with. Work often becomes your life, and the financial burden can be enormous. There’s nothing wrong with that, but not everyone feels more freedom and control and less stress that way. Many have the opposite response.

Besides, everyone has bosses. Depending on the size and type of company, entrepreneurs may have to answer to a board of directors, customers, and investors, not to mention federal, state, and municipal regulators and bureaucrats. Trust me, they can all be pretty bossy.

Myth 5: Corporate America is evil.
Every corporation — even giants like Apple and Walmart — began as somebody’s startup or small business. That’s right, a ginormous corporate behemoth is really just a small business that did really well. So why is entrepreneurship cool, while corporate America is evil?

I remember one of the mantras of the Occupy Wall Street movement was, “Corporations are not people.” Oh, yes, they are. They are run and staffed entirely by people. Every action they take and decision they make is by and for people. Their investors and customers are all people or companies that are themselves made up entirely of people. There is no distinction. Period.

As for companies, organizations, and governments that behave badly, it’s their leadership that’s the problem—the people running the show. So if you want to blame someone, blame the people not “corporate America.”

Myth 6: Technology destroyed all the jobs.
Ever since the Industrial Revolution we’ve worried about machines taking our jobs and technology taking over our lives. While outsourcing, offshoring, and technology have without a doubt changed the job market — particularly with respect to manufacturing — the popular mantra that there are no jobs is simply untrue.

If technology is destroying jobs, how do we explain the most lucrative and fastest-growing industry on the planet, technology? If people can’t find a job, chances are they lack in-demand skills and education. If anything, I think our families and educational system have done a poor job of keeping up with the changing market.

There’s also little doubt that the two big post-millennial recessions had a major impact on a growing gap between productivity and employment and the decline of median household income in the U.S. But that time frame also coincides with the advent of Web 2.0 and the distressingly low labor participation rate among Millennials.

Contrary to popular belief, technology is not destroying jobs. That’s a convenient excuse for a sluggish economy and a government that’s anything but business-friendly. But the more we behave like drones in a digital hive, the poorer we become. And that’s entirely by individual choice.

Don’t buy into popular myths. What you do with your career is your own business. Do what’s right for you, when it’s right for you. Follow your own path. Everything will work out fine.

Some Tips from 6 Top Entrepreneurs

Becoming a successful entrepreneur is no easy feat. Sacrifice, hard work and an unwavering determination for achieving greatness are required. So is surviving your mistakes — because they will happen.

At CreativeLive, I’ve always strived to learn from my own mistakes and to gain powerful insights from those who have successfully gone down the path before me. That’s why I reached out to six top entrepreneurs, writers and CEOs I’ve admired for years.

I asked each of them to share with me, in a selfie-style video clip, their single most impactful piece of advice for fellow entrepreneurs. Those interviewees included:

– Chase Jarvis, the prolific photographer and CEO at CreativeLive, who’s on a mission to revolutionize the way the world learns
– Jon Acuff, the best-selling author of five books designed to teach how to find and create meaningful work
– Sophia Amoruso, the founder of NastyGal and the best-selling author of GIRLBOSS, who launched one of the fastest-growing retail brands in recent history
– Lewis Howes, the best-selling author, lifestyle entrepreneur and podcast host, who’s interviewed more than 200 influential entrepreneurs on how to achieve greatness
– Nir Eyal, the best-selling author, entrepreneur and speaker, who’s pioneering the psychology behind creating habit-forming products
– Guy Kawasaki, the entrepreneur, investor and former chief evangelist at Apple, who’s helped dozens of well-known startups launch with a bang

Some Business Tips Every Entrepreneur Should Know

The biggest problem founders and small business owners have is that they’re experts in their field and novices in what it really takes to effectively run a business. That’s what usually trips them up, sooner or later.

Don’t let that happen to you. Admit that you don’t know what you don’t know about business, starting with these 15 tips guaranteed to help keep you and your company out of hot water. Some are straightforward, others are counterintuitive, but they’re all true. And some day they’ll save your butt.

Always make sure there is and will be enough cash in the bank.
Period. The most common business-failure mode, hands down, is running out of cash. If you know you’ve got a cash flow or liquidity problem coming up, fix it now.

You can’t fire bad employees fast enough.
You just can’t. Just make sure you know they’re the problem, not you (see next tip).

The problem is probably you.
When I was a young manager, my company sent us all to a week of quality training where the most important concept we learned was that 90 percent of all problems are management problems. When things aren’t going well, the first place to look for answers is in the mirror.

Take care of your stars.
This goes for every company, big and small. The cost of losing a star employee is enormous, yet business leaders rarely take the time to ensure their top performers are properly motivated, challenged, and compensated.

Your people are not your kids, your personal assistants, or your shrink.
If you use and abuse them that way, you will come to regret it. Capiche?

Learn to say “yes” and “no” a lot.
The two most important words business owners and founders have at their disposal are “yes” and “no.” Learn to say them a lot. And that means being decisive. The most important reason to focus – to be clear on what your company does – is to be clear on all the things it doesn’t do.

Listen to your customers.
It boggles my mind how little most entrepreneurs value their customers when, not only are their feedback and input among the most critical information they will ever learn, but their repeat business is the easiest business to get.

Learn two words: meritocracy and nepotism.
The first is how you run an organization – by recognizing, rewarding, and compensating based solely on ability and achievement. The second is how you don’t run an organization – by playing favorites and being biased.

Know when and when not to be transparent.
Transparency is as detrimental at some times as it is beneficial at others. There are times to share openly and times to zip it. You need to know when and with whom to do one versus the other. It comes with experience.

Trust your gut.
This phrase is often repeated but rarely understood. It means that your own instincts are an extremely valuable decision-making tool. Too often we end up saying in retrospect and with regret, “Damn, I knew that was a bad idea.” But the key is to know how to access your instincts. Just sit, be quiet, and listen to yourself.

Protect and defend your intellectual property.
Most of you don’t know the difference between a copyright, trademark, trade secret, and patent. That’s not acceptable. If you don’t protect and defend your IP, you will lose your only competitive advantage.

Learn to read and write effective agreements.
You know the expression “good fences make good neighbors?” It’s the same in business. The more effective your agreements are, the better your business relationships will be.

Run your business like a business.
Far too many entrepreneurs run their business like an extension of their personal finances. Bad idea. Very bad idea. Construct the right business entity and keep it separate from your personal life.

Know your finances inside and out.
If you don’t know your revenues, expenses, capital requirements, profits (gross and net), debt, cash flow, and effective tax rate – among other things – you’re asking for trouble. Big trouble.

You don’t know what you don’t know.
Humility is a powerful trait for leaders, and that goes for new business owners, veteran CEOs of Fortune 500 companies, and everyone in between. More times than not, you will come to regret thinking you knew all the answers.

Behind every failed company are dysfunctional, delusional, or incompetent business leaders. The irony is, none of them had the slightest idea that was true at the time. Even sadder, most of them still don’t. Don’t end up like one of them.