From The $100 Startup · Part I, Chapter 3

Follow Your Passion... Maybe

"Passion, though a bad regulator, is a powerful spring."
— Ralph Waldo Emerson

Gary Leff and the $250 vacation

Gary Leff is a CFO for two university research centers in northern Virginia. It's a good job. He has no plans to leave. The early-morning email traffic doesn't come from work, though — it comes from his part-time business.

Gary is a travel hacker. He earns hundreds of thousands of frequent-flyer miles every year through airline promotions and credit-card sign-up bonuses. Plenty of business travelers earn miles too, often without trying. But earning miles and turning them into actual vacations are two different problems. How many miles do you need? What if the airline says no seats are available on your dates? What about stopovers? Most people give up before they figure it out.

That's where Gary comes in. For $250 (covering up to two passengers on the same itinerary), he'll book the trip of your dreams. You tell him where you want to go, which airline your miles are with, and any constraints on your dates. He combs databases, calls airlines, and works every loophole. He specializes in First and Business Class — and some of his itineraries cover six airlines on a single award ticket. If he can't book the trip, you don't pay.

Last year the side business brought in $75,000. He's on track to clear six figures. Since he already has the CFO job and other ventures, he invests the money rather than spends it. "I honestly do this because it's fun," he told me.

Gary's business is a follow-your-passion business. He was passionate about travel. He found creative ways to book First Class around the world at Economy prices. He started helping friends do the same, then community members on travel forums, then strangers. Word got around. Eventually he had more requests than he could handle. The next logical step was to charge.

The instant-consulting business

Gary built his consulting business in a short period of time, with a basic website. There's no consulting school. There's no certification. You can be operational tomorrow if you follow two rules.

Once you have those two, the rest is a sketch. You need a single page that says: what you help clients do, what qualifies you to do it (which may have nothing to do with credentials), two stories of how others have been helped (do free work if you don't have paid clients yet), what it costs, and how to hire you immediately. That's the website.

Then you go find your first client. A deadline helps: I will have my first client on or before [short date]. Welcome to consulting.

Megan Hunt and the all-in approach

Most of the founders in the study became entrepreneurs by accident. Megan Hunt wasn't one of them. When I met her at the coworking space she owns in Omaha, it was 6pm and she was coming in to start her day — she's a night-owl who works with her infant in tow.

"I started when I was nineteen and a sophomore in college," she said. "I never intended to do anything but work for myself. I always knew that I didn't want a conventional job, so I never expected to resign myself to a fate other than the one I wanted as an artist. I worked a few 8-to-5 desk jobs, but I wasn't discouraged because I only saw them as the means to an end: gaining enough capital to start my own full-time venture."

Megan makes custom wedding dresses and bridal accessories full-time. She sells to women aged 24 to 30 from around the world (42% of her customers are international). After earning $40,000 her first year, she's scaling up with two employees and the coworking space.

She also has the obligatory disaster story — every founder in the book has one. Before Christmas 2010, she shipped 70 hours of high-end flower kits to two customers via USPS, and the packages disappeared. She refunded money she didn't have, wrote teary apology notes to brides who now had no flowers for their weddings, posted the whole story on her blog, and kept going.

"I spend every day learning from people who inspire and motivate me in the coworking space," she says, "and I interact every day with customers who are in the midst of their own love stories. I have a young daughter who I am able to bring to work. My earning potential is unlimited, and I am free to reinvest in my happiness with every dollar that comes in."

But is it really that easy?

It sounds simple: pick something you love and build a business around it. Gary and Megan and everyone else do this and the money rolls in.

The real answer is more complicated. Building a business around a passion can be a great fit for many people, but not everyone — and not every passion.

Three things tend to get glossed over in the rush to follow your passion.

1. Not every passion has a paying market

You can't just pursue any passion. There are plenty of things you might be passionate about that nobody will pay you for. Remember convergence — passion has to overlap with what other people will spend money on. I like pizza. I'll never be paid to eat it. I had to find something more interesting to the rest of the world.

Mignon Fogarty learned this the hard way. Before she was Grammar Girl — the wildly successful grammar podcast with a line of books and non-stop media — she ran a science podcast called Absolute Science. Here's how she tells it:

Before I launched the successful Grammar Girl podcast, I was the host of a science podcast called Absolute Science. I loved doing that show and I was passionate about it. I actually put more effort into promoting that show than I did for the Grammar Girl podcast, and although Absolute Science was well-received, after doing it for nearly a year it was clear that the show was never going to make enough money to make it worth the time required to produce it.

She didn't abandon podcasting — she traded science for grammar. The passion stayed. The audience changed.

Absolute Science	Grammar Girl
Passion... but not enough audience	Passion... and a substantial audience

2. You don't usually get paid for the hobby itself

You get paid for helping other people pursue the hobby — or for something one step over from the hobby. Travel writers don't get paid to travel; they get paid for the writing. Recipe developers don't get paid to cook for themselves; they get paid for the recipes.

Benny Lewis is the clearest example. He's from Ireland, speaks something like eight languages, and likes to say he gets paid to learn languages. The reality is more interesting.

I met Benny on a layover in Bangkok. He's possibly the most enthusiastic person I've ever met. Twenty-four years old, traveling for two years, an engineering grad with no aptitude for foreign languages who decided to learn Spanish in Seville. After six months of getting nowhere, he committed to speaking only Spanish for a full month, no exceptions. He didn't know how to conjugate verbs, so he used present tense and waved his arms behind him for "already happened." Within a few weeks, he was conversational.

The full immersion worked better than the previous six months combined. He moved to Berlin and learned German, then to Paris for French, then to Prague for Czech — a notoriously hard one. Seven fluent languages in two years.

"Benny, your skill is amazing," I said over mango juice. "Why don't you get more serious about teaching this method to more people?"

He'd been thinking about it. He hit on the name Fluent In 3 Months and went to work outlining everything he knew. The course is now available in eight languages, all taught by Benny. To market it, he makes YouTube videos giving apartment tours in five languages, stands on street corners in costume offering free hugs, and wears goggles on his hat so people will ask why. ("Easy way to get to know them and try to learn their language.")

Benny doesn't get paid to learn languages. He gets paid to help other people learn languages. Without the helpfulness, he'd just be the sober Irishman who speaks a lot of languages, and there would be no business model.

3. You may not want to combine your hobby with your work

If your hobby is your stress relief — the part of your week that makes the rest tolerable — you might not want to take full-time responsibility for it. Plenty of people in the study deliberately kept their passion and their work separate. Benjamin Franklin, an old-school entrepreneur, put it this way: "If passion drives you, let reason hold the reins."

The reality-check checklist

Before turning a passion into a business, run through these questions honestly.

The equation behind the businesses that work

When I asked the group of unexpected entrepreneurs about the follow-your-passion model, almost nobody endorsed it absolutely. Almost nobody dismissed it either. The nuanced version kept showing up: passion plus good business sense creates a business.

The cleaner equation:

(Passion + Skill) → (Problem + Marketplace) = Opportunity

Here's how it breaks down across the people in this chapter:

	Passion	Skill	Problem they solve
Gary	International travel	Booking high-value award tickets	Lack of industry transparency; perceived difficulty
Benny	Language learning	Language learning + a proven teaching system	People want to learn languages but have failed through traditional methods
Megan	Handmade dresses and wedding accessories	Custom handicraft + relationship-building over a long arc	Brides want something special and handcrafted
Mignon	Clear writing and the English language	Communicates grammar "rules" in a fun way	The perception that studying grammar is difficult or boring

Passion is one part of the equation. If Gary's award-ticket skill disappeared, his passion for travel wouldn't matter. No matter how passionate Megan is about her dresses, if no marketplace existed eager to buy them, she wouldn't be in business.

Four ways to monetize

Each of the four founders cashed in differently:

• Gary — set fee per service ($250 per itinerary)
• Benny — direct digital product at a fixed price ($29 for the language guide)
• Megan — direct physical product, variable pricing (custom dresses and accessories)
• Mignon — free service, underwritten by advertising and sponsorship

Each model has tradeoffs. Gary makes $250 at a time but has to earn the fee with real work. Benny sells for less per unit but the process is automated. Megan's income is diversified but labor-intensive. Mignon has reliable sponsor income but less control over her audience experience. None is universally better — each fits the underlying business.

The wider lesson

In Venice, California, Gabriella Redding built a million-dollar hula-hoop business after losing weight through hula. Before that she was a tattoo artist, and before that a restaurant owner. "I'm an artist," she told Forbes. "Artists are serial entrepreneurs because we have to figure out ways to sell our work. It's either that or you become a starving artist, and I'm not a starving artist."

Compared to working for money you don't enjoy earning, it's much easier to do what you love and get paid for it. You just have to find the right passion, the right audience, and the right business model. None of those three is optional.

Key takeaways

• Passion alone isn't enough. Passion plus skill plus problem plus marketplace equals opportunity. Drop any term and the equation collapses.
• You get paid for helping people pursue the hobby, not for the hobby itself. Benny doesn't get paid to learn languages — he gets paid to help other people learn them.
• You can launch a consulting business in one day. Be specific. Don't underprice. Build a single-page website and find your first client.
• Some passions are better as hobbies. If the hobby is what makes the rest of your week tolerable, monetizing it can break the part that makes it valuable.

Where this fits in the book

"Follow Your Passion... Maybe" complicates the conventional advice introduced in Chapter 1 and reinforced by Chapter 2 (Give Them the Fish). Passion is one input — necessary but not sufficient. The chapter closes Part I by establishing the discipline of testing a passion against the four-element equation before building anything around it.

The mechanics of how to package a passion into a real product show up later — in Chapter 6 (the one-page business plan), Chapter 7 (an offer you can't refuse), and Chapter 8 (launch).

Frequently asked questions

Should I follow my passion to start a business?

Maybe. Passion alone doesn't make a business — passion plus a skill that solves a problem for a willing market does. Almost nobody in the study said "always follow your passion." Almost nobody dismissed the idea either. Passion is fuel; convergence is the engine. You need both.

Can I really start a consulting business in one day?

Yes, if you follow two rules. Pick something specific — not "business consultant" or "life coach." Get concrete about exactly what you can do for someone. And don't underprice. Nobody trusts a $15-an-hour consultant. Charge at least $100 an hour and let the price signal the value.

What if my passion isn't something people will pay for?

Then it's a hobby, not a business — and that's fine. Most successful follow-your-passion businesses don't get paid for the passion itself; they get paid for helping other people pursue it. Benny Lewis doesn't get paid to learn languages. He gets paid to help other people learn languages.

When is it a bad idea to turn a passion into a business?

When the passion is your stress relief and you'd lose that if it became work. When you only enjoy doing the activity casually, not for 20 hours a week. When you don't want to teach others or deal with administrative work. If your hobby keeps you sane on weekends, monetizing it can break the part that makes it valuable.

Where does this fit in The $100 Startup?

Chapter 3, in Part I (Unexpected Entrepreneurs). It complicates the conventional "follow your passion" advice by adding a reality check: passion plus skill plus problem plus marketplace equals opportunity.