Hustling: The Gentle Art of Self-Promotion - TAKING IT TO THE STREETS - The $100 Startup: Reinvent the Way You Make a Living, Do What You Love, and Create a New Future - Chris Guillebeau

The $100 Startup: Reinvent the Way You Make a Living, Do What You Love, and Create a New Future - Chris Guillebeau (2012)


Chapter 9. Hustling: The Gentle Art of Self-Promotion


“Good things happen to those who hustle.”


One hundred and twenty miles from Boston in rural New Hampshire, hundreds of artists and art lovers gather twice a year for a communal experience. Before coming to the area, many of them connect online, arranging car-share services and planning meetups. After settling into lakeside cottages, they learn from professionals and spend time with one another, old friends and new friends alike.

It all started five years ago when Elizabeth MacCrellish was feeling isolated from other artists and wanted to create more of a sense of community in her rural area. “I invited my friends to join me for a weekend gathering centered on the arts,” she explained. She planned for a few dozen people, but 135 showed up—mostly from the West Coast, far from the small New England group she had expected.

Thus was born Squam Art Workshops, named after a lake in central New Hampshire. After that initial gathering, Elizabeth repeated the experience, first on an annual basis and then twice a year. The audience is one-third professional artists and two-thirds “regular people” with day jobs who enjoy arts and crafts as a hobby. Hundreds of people now come to each sold-out gathering.

As the workshops grew, Elizabeth pulled back to regroup. She did no traditional advertising of any kind, but more people kept signing up, strictly through word of mouth. In the third year of Squam, Elizabeth added an extra session in a new location … and ended up regretting it. She was tired and decided to spend the next year “dialing back and taking stock.” (She was initially reluctant about speaking to me for this book, but warmed up after I promised to write about the importance of community and relationships in her work.)

To register for Squam, attendees have to mail in their payment and information. This old-school system is one way that Elizabeth maintains a close connection with her tribe. She also carefully assigns people to specific cottages to ensure that newcomers are welcomed and plays Whack-A-Mole in delicately preventing cliques from forming. Invitations to take the Squam show on the road have arrived from the United Kingdom, Australia, and a dozen cities in North America; she always declines.

“I’m not a businessperson,” she says. “I just do what feels right, and it keeps getting more interesting.” Elizabeth isn’t against capitalism, but she wants to be sure that the growth of her business happens in a way that is comfortable for her. Midway through one of our phone calls, she likened her business model to the Amish, talking about a time when she visited a New England farmer’s market. Self-reliance is a core value in most Amish communities, and nearly everyone participates in commerce one way or another. But there is very little actual salesmanship; the molasses cookies and apple strudel sell themselves. Even for high-ticket items, prices are nonnegotiable—take it or leave it.

Elizabeth began the workshops as a personal project that grew into a sustainable business. “I never set out to build something more than a structured encounter with friends,” she says. Five years later, managing Squam—and making sure it grows in the right way—is Elizabeth’s full-time work. After the initial success, at least eight different workshops offering similar retreats sprang up elsewhere, many of which were founded by previous attendees who sought to replicate the event in their own way. It didn’t matter, though—the original Squam was the experience you just had to have for yourself.

What Is Hustling?

This chapter is all about hustling, or how to get the word out about a project. What does hustling mean? There are a few ways to look at it, but I like the approach in this poster by Joey Roth:

The distinction between the three icons represents the difference (and the likely success or lack of success) of a person or business hoping to promote something for sale. A charlatan is all talk, with nothing to back up their claims. A martyr is all action with plenty of good work to talk about, but remains unable or unwilling to do the talking. A hustler represents the ideal combination: work and talk fused together.

Being willing to promote in an authentic, non-sleazy manner is a core attribute of microbusiness success. As Elizabeth’s story illustrates, sometimes the best hustling lies in creating a great offer and getting people to talk about it. In other cases, you want to have as many of the right kind of customers as possible, so there’s nothing wrong with putting yourself forward.

In my work, the hustler image on the right is pretty much what I try to do every day as a writer and entrepreneur: lots of creating and lots of connecting. The connecting (i.e., the talk) isn’t always directly related to the work at hand—sometimes I’m supporting other people with their hustling—but on a good day, there’s plenty of creating and plenty of connecting.

Another way to look at it is

Style without substance = flash

(Also, no one respects these people.)

Substance without style = unknown

(Everyone who knows these people respects them, but not many people know them.)

Style with substance = impact

(This is the goal.)

When you’re first getting started with a project, how do you go from martyr to hustler? It’s simple. First things first: Take the time to make something worth talking about—don’t be a charlatan. But then start with everyone you know and ask for their help. Make a list of at least fifty people and divide them into categories (colleagues from a former job, college friends, acquaintances, etc.). As soon as the project is good to go, at least in beta form, touch base by sending them a quick note. Here’s a sample message:

Hi [name],

I wanted to quickly let you know about a new project I’m working on.

It’s called [name of business or project], and the goal is to [main benefit]. We hope to [big goal, improvement, or idea].

Don’t worry, I haven’t added you to any lists and I won’t be spamming you, but if you like the idea and would like to help out, here’s what you can do:

[Action Point 1]

[Action Point 2]

Thanks again for your time.

Note that you’re not sending mass messages or sharing anyone’s private info with the world; each message is personal, although the content is largely the same. You’re also not “selling” anyone on the project; you’re just letting people know what you’re up to and inviting them to participate further if they’d like to. The action points can vary, but they should probably relate to joining a contact list (this way you have their permission to touch base with them further) and letting other people know about the project.

The next step is to incorporate hustling into your ongoing regular work.

If You Build It, They Might Come …

It might happen by magic, but you’ll probably have to tell them about it. Even with Elizabeth MacCrellish’s low-key Amish selling model, she still began her summer workshops by recruiting friends and supporters. This is where hustling comes in. If half the work is building the house and the other half is selling it, here’s how a few other people sold it:

We spent no money on advertising for the first five months we were open. Instead, we decided to allocate more than half of our opening costs to have a thirty-by-fifty-foot mural of a bright and colorful tree painted on the side of the stand-alone brick building we’re in. That speaks way louder than any ad we could ever place. —Karen Starr, Hazel Tree Interiors

When I launched my membership program, I decided to start with some beta testers. I invited a hundred of my top prospects to try it out for the first two months before I opened membership … but I didn’t send them an email invite. Instead, I sent a hostage letter in a brown paper bag—folded and taped. People really got a kick out of it, and it worked! The letter led to a sales page with a personal video invite from me. —Alyson Stanfield, Art Biz Coach

We initially imagined a community of thousands for our triathlon and Ironman distance training programs. In reality, fewer members meant deeper roots and a much more powerful experience for everyone. Unlike most programs, which try to keep pushing the price higher, we reward our members by decreasing the price the longer they remain in the program. This is because we recognize that the more experience they have, the more they can help other members … and the more active they are in recruiting new members to join as well. —Patrick McCrann, Endurance Nation

First Things First: What Do You Have to Say?

I was sitting in a large conference room with my friend Jonathan Fields (also mentioned in Chapter 7). Jonathan is an ex-lawyer turned serial entrepreneur and author. Several presenters were having a group discussion on building a tribe of followers, and someone in the room asked a question about writing a book: “What’s the first step?”

One of the speakers gave a list of four or five ideas, and then at the end he said, “Oh, when you plan to write a book, you should also think about what you have to say.”

Jonathan and I looked at each other with the same thought: “Uh, isn’t that the first step?”

Getting the message out about your business is like writing a book: Before you do anything else, think about what you have to say. What’s the message? Why is it important now, and why will people want to know about it?

The Strategic Giving Marketing Plan

Freely give, freely receive: It works. The more you focus your business on providing a valuable service and helping people, the more your business will grow. A number of the subjects of our case studies discussed how giving (often described in different ways but with the same meaning) has been a core value of their business. One of the best descriptions came from Megan Hunt, the Omaha dressmaker we met in Chapters 1 and 3:

My marketing plan could be called strategic giving. When I launch a new line of dresses each year, I contact two or three influential bloggers and create a custom dress for them, which always brings in tons of new customers when they write about it. But most importantly, I turn my attention toward my clients. Often, I upgrade someone’s shipping to overnight for free, or double someone’s order, or include a copy of my favorite book with a handwritten note. I like to package my products for shipping like a gift to my best friend. This strategy has been a huge contributor to fast growth and popularity in my industry.

John Morefield, an unemployed architect during a time when jobs were scarce, set up shop in a Seattle farmer’s market with a sign that read “5-Cent Architecture Advice.” In exchange for a nickel, he would give advice on any problem that homeowners, real estate agents, or anyone else brought to him. The 5-cent advice was effectively a lead-generation program that might lead to additional business, but John legitimately and genuinely offered professional advice without the expectation of more than a nickel.

As news spread of the 5-cent architect, John got free advertising from CNN, NPR, the BBC, and numerous other media outlets. Because of the attention—and new clients who came in through the farmer’s market—John is now a successful self-employed architect, a key distinction from his peers who are still trying to get hired at firms.

Another way to practice strategic giving is to deliberately not take advantage of every opportunity to increase income. As my own business grew and I received more public attention, I began to receive a lot of requests for consulting sessions. I never really saw myself as a consultant, but I figured, Why not? If this is what people want, maybe I can do it. I created a page on my website, received plenty of interest, and conducted a few sessions as a test. Long story short, the whole thing felt false and inauthentic to me. I had helped lots of people with specific problems before, but not on a pay-per-time basis. When I talked with people who had paid for access to me, I felt physically ill. I realized my discomfort was in doing it for money, so I stopped.

I still do some limited consulting whenever I can, but now I do it for free. With the right people and on my own terms, I enjoy it—especially without the pressure of knowing they are paying me to deliver. I’m not always able to offer helpful advice, but I know that when I can be helpful, that person will likely be there for me at some point in the future. It’s not about keeping score or trading favors on a quid pro quo basis; it’s about genuinely caring and trying to improve someone else’s life whenever you can.*

Like any kind of marketing, this practice can be manipulated or abused. Tourists landing at the international terminal at LAX are met outside by friendly people with official-looking clipboards who offer to help with directions to the city. “Hey, where are you headed today?” they ask. “Can I be of assistance?” After they provide directions or answer questions from unsuspecting tourists, there’s a pitch: “I’m working today on behalf of a great organization. Can you help us out with a donation?” The implied message is, I just helped you … now it’s your turn.

This isn’t the kind of strategic giving that serves your interests well in the long term. The intention of the airport solicitors isn’t to be helpful; they are merely using helpfulness as a tool to gain the trust of unsuspecting tourists. Strategic giving is about being genuinely, truly helpful without the thought of a potential payback.

Building Relationships Is a Strategy, Not a Tactic

Getting to know people, helping them, and asking for help yourself can take you far. This is not a non-profit endeavor; it often pays off in real money (with interest!) over time. But it is a long-term strategy, not a short-term tactic to copy for quick success.

Originally from South Dakota, Scott Meyer was working as a professor of peace studies in the Arctic Circle in Tromsø, Norway. (It was a long way from home, but the winters were familiar, he explains.) Meanwhile, his brother John was a consultant for Accenture in Minneapolis. Scott and John’s migration away from their roots was normal—back in South Dakota, there was a clear divide between “people who stayed” and “people who got out.”

After a few years away, both Scott and John began to think of returning home with a mission. South Dakota wasn’t a bad place, and there was a growing community of entrepreneurs there, many of whom had a problem. Small businesses in the region tended to be run by people with fewer technical skills than those in Minneapolis or Chicago, the region’s main hubs. “Around here,” Scott told me, “people tend to use an old-school phone book to contact someone, and many business owners struggle with using email effectively. We knew we could help them grow their business.”

Scott and John founded 9 Clouds, a consultancy designed to help local businesses reach more customers through improved communication while gently educating them along the way. They give clients the fish by helping them reach new customers. Their clients are smart but worry about wasting time with new technology. 9 Clouds shows them the benefits of learning new tools that have been proved to be useful.

The firm works hard to drum up business, but it focuses first on drumming up value. “Every chance we get, we talk and share information with others and support them in their work,” Scott says. “It may not be a sale or partnership, but building those relationships today always comes back around for new opportunities tomorrow.” The community is noticing: 9 Clouds won second place in the South Dakota Governor’s Giant Vision contest, and John was recognized by BusinessWeek as an up-and-coming leader. 9 Clouds did $45,000 in net income during the first six months of operation, $180,000 the next year, and is now on track to becoming a mid-six-figure business.

First Say Yes, Then Say “Hell Yeah”

Other business books will tell you about saying no: how you should guard your time, “only do what you’re good at,” and turn down far more requests than you accept. As a business grows over time and options for growth become more selective, that may indeed be useful advice.

But what if you took the opposite approach, especially at first? What if you deliberately said yes to every request unless you had a good reason not to? The next time someone asks for something, try saying yes and see what it leads to. Whatever success I’ve had in my own work thus far has always come from saying yes, not from saying no.

Derek Sivers, who founded a business he later sold for $22 million (he then donated the money to a charitable trust), offers an alternative strategy: As things get busy, evaluate your options according to the “hell yeah” test. When you’re presented with an opportunity, don’t just think about its merits or how busy you are. Instead, think about how it makes you feel. If you feel only so-so about it, turn it down and move on. But if the opportunity would be exciting and meaningful—so much so that you can say “hell yeah” when you think about it—find a way to say yes.

Give Something Away and Watch People Jump

Are the crickets chirping in your business? There’s nothing like a contest or giveaway to get people engaged. I regularly receive 1,000 comments or more on a single Facebook post giving away a $15 book. I used to wonder, “What is the last person thinking? ‘Nine hundred ninety-nine people have entered, but maybe I’ll be the lucky one’?” Over time I realized that it wasn’t so much about winning as it was about social participation. If all your friends are putting their names down, why wouldn’t you do the same thing?

The difference between a contest and a giveaway is fairly simple: A contest involves some kind of competition or judging, whereas a giveaway is a straight-up free offer provided to winners through random entries. There are pros and cons to each: A contest usually requires more work for both the aspiring winners and the business hosting the contest, but it can generate more interest. A giveaway is quick and easy and can generate a large quantity of entries, but since there’s usually nothing to do other than put your name down, the typical giveaway doesn’t create much real engagement. For the best results, experiment over time with both methods.

The $10,000, Ten-Hour Marketing and Sex Experiment

“In the future, marketing will be like sex: Only the losers pay for it.”

This widely circulated statement first appeared in a December 2010 article in Fast Company magazine. Guess what? The future is here. It may not be completely for losers, but the role of paid advertising in marketing has long since changed. The vast majority of case-study subjects I talked with built their customer base without any paid advertising at all; they did so largely through word of mouth.

The One-Page Promotion Plan

Goal: To actively and effectively recruit new prospects to your business without getting overwhelmed.


Maintain a regular social media presence without getting sidetracked or overwhelmed. Post one to three helpful items, respond to questions, and touch base with anyone who needs help.

Monitor one or two key metrics (no more!). Read more about this in Chapter 13.


Ask for help or joint promotions from colleagues and make sure you are being helpful to them as well.

Maintain regular communication with prospects and customers.


Connect with existing customers to make sure they are happy. (Ask: “Is there anything else I can do for you?”)

Prepare for an upcoming event, contest, or product launch (see Chapter 8).


Perform your own business audit (see Chapter 12) to find missing opportunities that can be turned into active projects.

Ensure that you are regularly working toward building something significant, not just reacting to things as they appear.

While thinking about the quote and drafting this chapter, I decided to conduct an unscientific experiment to measure paid ads versus free hustling. Over the course of a month, I spent $10,000 on carefully selected ads and sponsorship for my Travel Hacking Cartel service. I also spent ten hours hustling, writing guest posts, recruiting a joint venture with another service, touching base with journalist contacts, and so on. Here are the results:

Ad Cost: $10,000
(+2 hours of setup)


Hustling Cost: 10 Hours
Zero Dollars

Number of New Customers: 78

Number of New Customers: 84

Estimated Value of New Customers: $7020

Estimated Value of New Customers: $7560

Approximate hour-per-hustle value: $756

Do we have a clear winner? I think so, but with a couple of disclaimers. First, one could say that I had access to relationships that others don’t have and those relationships were what determined the high hour-per-hustle value. This may be partly true. However, the whole point of hustling is to put your relationships to good use, whatever they are. Not everyone may be able to earn $756 per hustling hour. However, some situations could have produced an even higher hustling value.

It is also true that hustling time is not unlimited. If I had $100,000 to spend instead of $10,000, the situation might indeed be different. Combining hustling with paid advertising (again, carefully selected) could be a viable option for some. The point is that hustling can take you far. When you’re thinking about how to get the word out and build your business, think about hustling first and paid advertising later (if at all).

One objection to the hustling and relationship-building strategies described in this chapter is that they take time. Well, of course they do—they’re a big part of your work. But if you’re worried about spending all day on a social networking site, you can avoid doing that by sticking to a series of quick check-ins. I maintain a text file of information and links to share, and a couple of times a day I go online and post something. At the same time, I scan all the messages that have come through for me and respond to as many as possible. Although I sometimes spend more time out of habit or interest, the whole process doesn’t have to take any longer than ten to fifteen minutes a day.

The point is to do what makes sense to you. Get up in the morning and get to work. Make something worth talking about and then talk about it. Who do you know? How can they help? And of course, the answer lies in being incredibly helpful yourself.


If you’re not sure where to spend your business development time, spend 50 percent on creating and 50 percent on connecting. The most powerful channel for getting the word out usually starts with people you already know.

If you build it, they might come … but you’ll probably need to let them know what you’ve built and how to get there.

When you’re first getting started, say yes to every reasonable request. Become more selective (consider the “hell yeah” test) as you become more established.

Use the One-Page Promotion Plan to maintain a regular schedule of connecting with people as you also spend time building other parts of your business.

*I use this example to illustrate that having a good opportunity doesn’t mean you should pursue it. I’m not opposed to consulting in general. It just wasn’t a good fit for me.

I thought 1,000 entries for a basic giveaway was pretty good until Jaden Hair from Steamy Kitchen told me she receives as many as 50,000 entries for her giveaways, all for a prize as simple as a set of cookbooks.