From The $100 Startup · Part II, Chapter 9

Hustling: The Gentle Art of Self-Promotion

"Good things happen to those who hustle."
— Anaïs Nin

Elizabeth MacCrellish and the Squam approach

A 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 they arrive, many of them connect online to arrange car-shares and plan meetups. After settling into lakeside cottages, they learn from professionals and spend time with each other.

It started when Elizabeth MacCrellish was feeling isolated from other artists and wanted 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 planned for a few dozen. A hundred and thirty-five showed up — mostly from the West Coast, far from the small New England group she'd expected. That was the first Squam Art Workshops.

Squam now runs twice a year and sells out. Two-thirds of the attendees are "regular people" with day jobs who do arts and crafts as a hobby. The other third are working professionals. Elizabeth doesn't do traditional advertising of any kind. The whole growth pattern is word of mouth.

To register, attendees have to physically mail in their payment and information. That archaic system is one way Elizabeth keeps a close connection with her tribe. She carefully assigns people to specific cottages so newcomers are welcomed. She plays "whack-a-mole" preventing cliques from forming. Invitations to take Squam on the road have come from the UK, Australia, and a dozen cities in North America. She declines them all.

"I'm not a business person," she says. "I just do what feels right, and it keeps getting more interesting." She likens her model to the Amish at a farmer's market — molasses cookies and apple strudel sell themselves. Even high-ticket items are non-negotiable: take it or leave it.

Charlatan, martyr, hustler

The designer Joey Roth drew a poster that's stayed with me. Three figures stand side by side. A charlatan is all talk, with nothing to back it up. A martyr is all action, doing great work but unable or unwilling to talk about it. A hustler is the combination — work plus talk, fused.

Being willing to promote in an authentic, non-sleazy way is one of the strongest predictors of microbusiness success. As Elizabeth's story shows, sometimes the best hustling is creating a great offer and getting people to talk about it themselves. Other times you need more of the right kind of customers, and there's nothing wrong with putting yourself forward to get them.

One more way to look at it:

• Style without substance = flash. Nobody respects these people.
• Substance without style = unknown. Everyone who knows them respects them. Not many people know them.
• Style with substance = impact. The goal.

The 50-person personal list

When you're getting started, the highest-leverage move is usually the simplest: tell the people you already know. Make a list of at least fifty people and divide them into categories — former colleagues, college friends, acquaintances from a hobby or a previous city. As soon as the project is good to go (or even just in beta), send each one a personal note.

You're not sending mass messages or sharing anyone's private info. Each note is personal even if the content is roughly the same. You're not selling — you're inviting. The two action points should usually be (1) some way to stay in the loop (join the list, follow the page) and (2) some way to spread the word (forward to one friend, share if it resonates).

The personal-list approach outperforms cold outreach by a wide margin. Almost every successful launch I've seen has started here.

Strategic giving as a marketing plan

"My marketing plan could be called 'Strategic Giving.'" That's how Megan Hunt — the Omaha dressmaker we met in Chapter 2 — describes her approach.

"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."

John Morefield, an unemployed architect during the recession, set up shop in a Seattle farmer's market with a sign that read: "5-cent architecture advice." In exchange for a nickel, he gave real advice on any problem a homeowner or real estate agent brought to him. The five-cent service was effectively lead generation, but John genuinely offered professional advice without the expectation of more than a nickel. The story got picked up by CNN, NPR, and the BBC. He's a successful self-employed architect now. His peers are still trying to get hired at other firms.

Another version of strategic giving: deliberately not taking every opportunity to increase income. As my own business grew, I started getting requests for paid consulting sessions. I set up a page and tried it. When I talked with people who'd paid me, I felt physically ill — I couldn't focus on the advice while watching the clock on the meter. I realized the discomfort was in doing it for money, so I stopped charging. I still do some limited consulting — for free, with the right people, on my own terms. No quid pro quo. No keeping score. The right people show up later when you need them.

Like any kind of marketing, this practice can be abused. The friendly people with clipboards outside LAX who offer to help tourists with directions are not actually being helpful — they're using helpfulness as a tool to set up a donation pitch. Strategic giving is being genuinely useful without the thought of payback. The payback comes anyway.

"Building relationships" is a strategy, not a tactic

Scott Meyer was working as a Peace Studies professor in the Arctic Circle in Tromsø, Norway. His brother John was a consultant for Accenture in Minneapolis. Both eventually thought about returning home to South Dakota with a mission. The growing community of entrepreneurs there often used old-school phone books and struggled with email. Scott and John knew they could help.

They founded 9 Clouds, a consultancy designed to help local businesses reach more customers through improved communication. They give clients the fish — actual customer growth — while gently educating them along the way. "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."

9 Clouds did $45,000 in net income in their first six months, $180,000 the next year, and is on track to become a mid-six-figure business.

First say yes, then say "hell yeah"

Other business books will tell you about saying no — guard your time, only do what you're good at, turn down more requests than you accept. That's reasonable advice once a business is established. At the start, the opposite often works better.

What if you deliberately said yes to every reasonable request, unless you had a good reason not to? Whatever success I've had has almost always come from saying yes, not from saying no.

Derek Sivers (who founded a business he later sold for $22 million, then donated the money to a charitable trust) offers a sharper version once things get busy: the "hell yeah" test. When an opportunity shows up, don't just weigh the merits. Notice how it makes you feel. If you feel only so-so about it, turn it down. If the opportunity would be exciting and meaningful — so much so that thinking about it makes you say "hell yeah" — find a way to say yes.

The one-page promotion plan

The $10,000-versus-ten-hours experiment

"In the future, marketing will be like sex: only the losers pay for it." That line first showed up in a December 2010 Fast Company article. The future is mostly here. It's not quite "for losers" — but the role of paid advertising in microbusiness marketing has changed.

While drafting this chapter, I ran an unscientific experiment to measure paid ads against free hustling. Over the course of a month, I spent $10,000 on carefully-selected ads and sponsorships for my Travel Hacking Cartel service. I also spent ten hours hustling — guest posts, joint-venture outreach, touching base with journalist contacts.

	Paid ads	Hustling
Cost	$10,000 + 2 hours of setup	10 hours · $0
New customers	78	84
Estimated value	$7,020	$7,560
Per hour of effort	~$3,500 lost	~$756 gained

A clear winner — with disclaimers. I had relationships others might not have, and those relationships drove the per-hour value. On the other hand, hustling time is not unlimited. If I'd had $100,000 to spend instead of $10,000, the comparison might look different. The point isn't that paid advertising is always wrong. It's that hustling can take you much further than people assume, and the cost ratio is steep enough that it deserves to be the first move.

Key takeaways

• Split your business-development time roughly 50/50. Half on creating, half 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 built and how to get there.
• Say yes to almost every reasonable request when you're starting out. Once established, use the Hell Yeah test.
• Hustling beats paid ads, dollar for dollar, in most micro-business situations. Start there.
• Run a sustainable rhythm. Use the one-page promotion plan to keep the rhythm without burning out.

Where this fits in the book

"Hustling" sits in Part II of The $100 Startup, between Chapter 8 (Launch!) and Chapter 10 (Show Me the Money). Launches are the big events; hustling is the everyday rhythm between them. The free one-page promotion plan template is the dedicated landing page for the system in this chapter, with a printable PDF and a worked example.

Frequently asked questions

What does "hustling" mean in business?

The fusion of work and talk. A charlatan is all talk; a martyr is all action without talk; a hustler is both. The combination is one of the strongest predictors of microbusiness success.

How do I get the word out about my new business?

Start with everyone you already know. Make a list of fifty people, send each a personal note explaining what you're working on and two ways they can help. The personal-list approach outperforms cold outreach by a wide margin.

Does paid advertising work for small businesses?

Sometimes — but $10,000 of paid ads brought in 78 customers worth roughly $7,020 in my experiment. Ten hours of hustling brought in 84 customers worth $7,560. Hustle first, advertise later (if at all).

What is "strategic giving" as a marketing approach?

Doing genuinely useful things without an immediate ask. Megan Hunt ships orders like she's mailing a gift to her best friend. John Morefield ran a five-cent architecture booth and earned coverage from CNN, NPR, and the BBC. The payback comes anyway, often larger than you'd have asked for.

Where does this fit in The $100 Startup?

Chapter 9, in Part II. Between Chapter 8 (Launch!) and Chapter 10 (Show Me the Money). Launches are the events; hustling is the rhythm between them.