From The $100 Startup · Part III, Chapter 13

Going Long

"Nothing will work unless you do."
— Maya Angelou

Tsilli Pines goes full-time, then doesn't

The cliché about entrepreneurs is that they're Type-A motorcycle riders, charging the castle. The reality is that most of the founders in the study are not risk-takers by temperament. They define risk and security differently from other people. They take careful, step-by-step paths.

Tsilli Pines is a designer who moved from California to my hometown of Portland. Over eight years she built a business making ketubot, custom-designed Jewish wedding contracts — priced at $495 each. For most of that time the business was a night-and-weekend project alongside her day job at a design studio. The day job paycheck made her feel safe to experiment. And the limited hours forced her to make every one count.

By the end of 2009, the business had grown steadily, and Tsilli felt prepared to leap. She gave notice and went full-time. She had jumped.

The view on the other side wasn't what she'd expected. The first week of freedom felt great. The second week she started wondering what to do all day. "I underestimated the value of having some work that was collaborative and not self-directed." Over the next few months, business earned less than expected. Orders were still coming in, but Tsilli felt drained of the creativity she'd thrived on while starting up.

"The all-or-nothing paradigm was too much pressure," she said. "I'm running a creative business, but it's a creativity killer for me to define my whole income on the need to continuously deploy my creativity." Six months after leaving, she approached the design firm with a proposal: how about coming back part-time? They said yes and were happy to have her.

She works three days a week at the studio as a contractor, not an employee — which gave her the unexpected but important sense of still earning all her income "on her own," roughly half from the studio and half from her business. "I'm still laying brick after brick. The different pieces interlock, and over time they may build to critical mass. But right now I'm in a good place."

It was right for her to leave. It was right to go back. Both decisions count.

Three answers to the long-term question

Sooner or later, every founder faces the same question: where am I going with this thing? Three founders in the study answered it three different ways.

Option 1: Stay small

Cherie Ve Ard has been working on her own since age twenty. Her father was an entrepreneur too — he started the family software business that she eventually took over. She's now thirty-eight, the company builds custom software for healthcare providers, and in 2007 she and her partner Chris Dunphy hit the road in an RV. They added a mobile-apps side business along the way.

Cherie has deliberately turned down expansion opportunities. "The smartest decision I made was to set a specific intention to not grow the business. Growing up as the daughter of an entrepreneur, I watched my father's creativity and inventor mindset get sapped as the business grew from just him to over fifty employees. The stress wore him down and diminished his quality of life."

When we last spoke, Cherie was on the island of St. John, where she and Chris had settled in for a few months ("maybe longer, or as long as we feel like it"). She earns at least $50,000 a year. "My feeling of being a successful business owner is based on the quality of life I lead, not the amount of money I earn. I own my business; the business doesn't own me."

Option 2: Go medium

In the SoDo district of Seattle, a factory hums with the sound of sewing machines. More than twenty employees stitch backpacks and laptop bags for Tom Bihn. I toured the factory with Tom and his business partner Darcy Gray. Tom isn't afraid of growth. He turned his back on the biggest growth opportunity available — distribution through big-name retailers, who'd repeatedly asked for partnerships.

We chose to be our own manufacturer and direct retailer initially because it's more interesting: we get to march to our own drummer. If the goal is simply to make money, well, that's just boring. We wanted to make a cool business with cool products, cool customers, and cool employees. To sell to mass-market retailers may or may not be lucrative, but it does little for brand identity. It can also tie your fortune to a company over which you have no control: if they go down, you may go too. Our future is tied to what we do, decisions we make, and that's wicked good fun.

Cash flow comes from many individual customers, so Tom never has to worry about a big retailer dropping inventory. He can charge a good price for the bags and support all his employees. When I asked Tom about his worst days in the business, he said something that has stuck with me ever since:

All the bad days have two things in common: you know the right thing to do, but you let somebody talk you out of doing it.

At least in this case, Tom never let himself get talked out of what was clearly the right thing for him.

Option 3: Split the difference

Jessica Reagan Salzman runs a bookkeeping shop in Attleboro, Massachusetts. I knew Jessica was a numbers person when she gave me an estimated income projection for the next year of exactly $110,899 — not "about a hundred or so."

She started the business after an unsettling experience at a CPA firm where she'd just been hired. As she settled in, the math kept not balancing. She finally figured it out — the firm itself was in trouble and wouldn't have enough to pay her when the first payroll cycle came around. She quit and went solo.

The business was profitable as a side project but didn't make enough to support a family. Then her husband Michael called to say he'd just been laid off, effective immediately. With their second child three weeks old, Jessica took the business full-time. Michael became the primary caregiver at home. The business grew — and then started growing too fast.

"We had made major progress in growing revenues, but we had also experienced soaring costs, and our bottom line clearly reflected the necessity for a major change." She assumed that as a business improves, you hire people. Right? Wrong. Hiring people creates much higher costs and fixed obligations. She switched back to a sole proprietorship and returned to a one-woman shop. On purpose.

Don't be a firefighter: work on the business

As your project grows, it's easy to spend all your time responding to things and almost no time creating anything. The fix is to deliberately set aside time to work on the business rather than in it.

Every morning, set aside 45 minutes without email or internet. Devote it strictly to activities that improve the business — nothing that merely maintains it.

Monitor 1–2 key metrics

Two rules. First: pick 1–2 metrics and stay aware of them at any time — usually sales, cash flow, or incoming leads. Second: leave everything else for a biweekly or monthly deeper review.

Common daily-attention metrics:

• Sales per day
• Visitors or leads per day
• Average order price
• Sales conversion rate
• Net promoter score

Some businesses go more specific. Brandy Agerbeck (the graphic facilitator from Chapter 7) needs a certain number of bookings each year. She tracks them on a set of index cards. When the cards fill up, she knows she's good for a while and can focus on other things.

A caution: be wary of delegating all financial knowledge to someone else. Personalities vary, but having "no idea" about money stuff is usually a bad sign.

Built to sell: a different model

John Warrillow built and sold four companies before "retiring" to write, speak, and invest. His model is specifically for owners who want to sell their business one day. It's a different model from most of what's in this book.

	Built to Sell	$100 Startup
Required capital	Variable, often high	Variable, usually low
Employees	Required	Optional
Focus on systemization	High	Variable
Freedom payoff	Big payday	No big payday
Secondary benefit	Build and move on	Do what you love

Neither model is better. They serve different goals. If you want the option to sell one day, John's most important point is that you have to plan for it. The business has to produce something at the intersection of teachable and valuable. A CPA's expertise is valuable but not easily teachable — she can't bring someone in and hand the practice over. Busing tables is teachable but not valuable (lots of people can do it). A subscription research service or a focus-group consultancy is both. That intersection is where a sellable business lives.

Key takeaways

• There's more than one road to freedom. Tsilli's part-time + business split, Cherie's stay-small commitment, Tom's go-medium factory, and Jessica's back-to-solo decision are all valid. Pick what fits the freedom you actually want.
• Work on your business, not just in it. 45 minutes every morning, before email, on activities that improve rather than maintain. Initiate, don't respond.
• Monitor 1–2 key metrics daily. Leave everything else for a monthly deeper review. Avoid delegating all financial knowledge.
• Built to Sell is a different model. Higher capital, employees required, focus on systemization, big payday at the end. Neither this model nor the $100 Startup model is universally better — they serve different goals.

Where this fits in the book

"Going Long" sits in Part III between Chapter 12 (How to Franchise Yourself) and Chapter 14 (But What If I Fail?). The chapter answers the most personal question of the whole book — what kind of business do you actually want to build, and for how long?

Frequently asked questions

Should I stay small or scale up?

Whichever fits the kind of freedom you want. Cherie Ve Ard stays small in St. John; Tom Bihn went medium with twenty employees and his own Seattle factory; Jessica Reagan Salzman went big, then went back to one-woman after costs ran away. Each was right for the person who chose it.

How should I monitor my business?

Pick 1–2 daily metrics (sales, cash flow, or leads). Review everything else biweekly or monthly. Brandy Agerbeck tracks bookings on index cards. When the cards fill up, she's good for a while.

What does it mean to "work on" your business?

45 minutes every morning before email, on activities that improve rather than maintain — business development, offer development, fixing long-standing problems, pricing review, initiating customer communication. The rule: initiate, don't respond.

What is a "built to sell" business?

A business designed for an eventual sale. The key requirement is something at the intersection of teachable and valuable — both. A subscription research service is both; a CPA practice and a table-busing job each miss one side. Not the same model as most $100 Startup businesses, but the comparison is useful.

Where does this fit in The $100 Startup?

Chapter 13, in Part III. Between franchising yourself (Chapter 12) and the closing fear chapter (Chapter 14). The chapter covers the long-term shape of the business and the practical disciplines that make a long-term business work.