Afford Anything

Category: Entrepreneurship

Written By Julia Kelly

How to Manage Two Successful Businesses (and Why One Wasn’t Enough)

In 2015, we ran a story about Julia Kelly, an entrepreneur who makes a six-figure income as a caricature artist.

Where is she now?

We decided to follow up her story. How sustainable is her business? How passive is her income?

Here’s Julia, with a follow-up in her own words. Take it away, Julia!

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The following is written by guest contributor Julia Kelly

When we left off, I was running JK Expressions and I was a couple of months away from finishing my degree. I was beyond excited to be done with my degree and focus on the business full time – I was pretty sure I would be living the dream!

I was in for a disappointment. About eight months after graduating and focusing on nothing but the business, it was hitting record revenues but I was dissatisfied, bored, unmotivated and thinking seriously about getting a “real” job.

I was confused. Everything looked great from the outside: I was my own boss, had a super flexible schedule, tons of time for hobbies, and good money.

What was the problem?

It probably would have worked for a lot of people — there’s tons of advantages to running a business like that:

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Written By Paula Pant

The eerie similarities between owning rental properties and running an online business

In June, I flew to Atlanta and toured a few of my rental units. This was the second visit I’ve made to these properties in four years.

During that visit, I met with my property manager and a few of my tenants, and I had lunch with my contractor. He and I met at a suburban Atlanta strip mall. 

We ordered a basket of spicy chicken wings and fries, then took out a water-logged spiral notebook and planned a $20,000 renovation.

Here’s what the early brainstormed edition of those plans looked like:

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By Paula Pant

#200: What I’ve Learned from Interviewing 500 Millionaires — with Jaime Masters of Eventual Millionaire

Nine years ago, I was flipping through an issue of Kiplinger Personal Finance magazine (as any normal 26-year-old does), when I came across an article about a woman who paid off $70,000 in debt in 16 months.

Her name was Jaime. She lived in Maine, with her then-husband and their young son. Her husband was a professional juggler who earned $30,000 per year; she brought home 3x his income.

They bought the trappings of the American Dream: the suburban house with a white picket fence, a brand-new Honda Civic, a Jeep CJ7 with 36” tires, several kayaks, and a premium cable subscription.

The result? They found themselves in massive debt, with a combination of vehicle loans, student loans, and a home equity line of credit.

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By Paula Pant

#180: The Million-Dollar, One-Person Business – with Elaine Pofeldt

Elaine Pofeldt, a writer for CNBC, Forbes, Fortune, Money Magazine and other business publications, decided to deep-dive into the world of solopreneur million-dollar companies.

What are the stories of entrepreneurs who gross $1 million or more in their businesses, despite having no employees? How did they begin? What do they do differently?

She interviewed hundreds of founders of non-employer seven-figure companies and wrote a book about her findings called The Million-Dollar, One-Person Business. Today, she joins us on the podcast to talk about what we can learn from this special class of entrepreneurs.

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Written By Paula Pant

“What I’ve Learned from Building an Eight-Figure Business” — an interview with Rand Fishkin

I’ve been following Rand Fishkin’s career for years. He has one of the best rags-to-not-quite-riches-yet stories I’ve heard.

Rand is a college dropout who spent his early 20s spiraling into a deep debt hole. His problems began when he tried to grow a marketing company but funded it in the worst way possible. He leased office space, rented booths at conferences, hired expensive contractors — and paid for everything with a personal credit card. Yikes.

His credit card debt ballooned to $150,000. He couldn’t make the minimum payments, so he defaulted. The late fees and penalty interest rates caused his debt to swell to more than $500,000.

Anyone else might have declared bankruptcy, but Rand stayed the course. He doubled down at work. He decided to specialize in a marketing niche, search engine optimization, which set him apart from the pack.

He brought new clients into his business. He developed internal tools to use for his clients, then started selling subscription-based access to this software.

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Written By Paula Pant

How to Live Louder than the Sound of ‘Should’

One month ago, I made a speech at the World Domination Summit in Portland about the importance of being yourself, even if this requires setting difficult boundaries or relinquishing your people-pleasing tendencies.

If you’re a creative entrepreneur, such as an artist, writer, musician, designer, craftsman, entrepreneur, or any other type of creator … this is advice you might not have heard before.

I argue that your best business move is to stop giving a sh*t about what other people think. Even your customers.

It’s a counterintuitive philosophy, one that runs contrary to the seemingly-benign “I want to help others” mindset that’s preached in the world of online entrepreneurship. I argue that your effect on others is outside of your control, so the best thing you can do is be yourself and let the chips fall where they may.

Bending over backwards to please others is inauthentic and, ultimately, ineffective. People will be served the most when they see a confident, strong person who is true to themself.

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By Paula Pant

#145: How I Paid Off $500,000 in Credit Card Debt, then Launched a Company with $35 Million in Annual Revenue — with Rand Fishkin, Founder of Moz

When Rand Fishkin was 25 years old, he carried $500,000 in credit card debt.

Less than a decade later, Rand was the Founder and CEO of a company that grossed $35 million in annual revenue.

In this podcast episode, Rand shares the story of hitting his financial rock-bottom and making the ultimate comeback.

The saga […]

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By Paula Pant

#138: How to Create an Authentic Life

There’s a famous quote that’s attributed to Henry Ford. The quote says, “If I had asked people what they wanted, they would have said faster horses.”

There’s no proof that Henry Ford actually said this. But whether or not that quote is historically accurate, the point remains. If Elon Musk had asked people what they […]

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By Paula Pant

#107: How Scott Harrison Brought Clean Water to 7.3 Million People

Scott Harrison spent 10 years as a New York City nightclub promoter, partying until sunrise every morning and ingesting almost every substance imaginable.

But when he was 28, he realized his life lacked meaning.

“My tombstone might say, ‘here’s the guy who got thousands of people drunk,’” Harrison said.

Feeling lost, he decided to volunteer […]

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