Startups

Pop quiz: How much can you learn about someone by peeking at the recent social media ads they’ve been targeted with?

You tell me. Here are some screenshots of what I’ve seen lately on Instagram:

Career Handbook

The first time I quit my job to pursue self-employment, I was confident, focused, and ambitious. If you have a laptop, some Gary Vee in your earbuds, and a dream… that’s all you need, right?

Wrong. I bled out my life savings — about $30,000 USD — in about a year. As I crawled back to 9-to-5 life, my confidence bloody and bruised, I vowed to never put myself in a career-crippling scenario again.

Work became stable and boring once more in the years that followed. …

Entrepreneurs

About six years ago, a book called Rocket Fuel burst onto the scene and transformed the way aspiring CEOs think about business partnerships. Authors Gino Wickman and Mark C. Winters’ had produced *the* handbook for how the working dynamic between visionaries and integrators can make or break a company. Starting out in business no longer meant you had to figure it out all by yourself, and as it turns out, most successful empires flourish by having a Jobs/Wozniak or Sandberg/Zuckerberg-ian duo at the top of the food chain.

Salesman John Paul Dejoria and stylist Paul Mitchell probably already had this…

I attribute the majority of my professional success to studying music. Even though I ended up not pursuing the arts professionally, learning an instrument taught me rigor, failure, and the power of deliberate practice. It’s a sentiment echoed by many who intensely pursued a sport or extracurricular activity that required mastery and dedication.

As a French horn player, I started fairly late, at 11 years old. To be successful on an orchestral string instrument, you usually need to start way earlier, which is why violins exist in quarter-size, half-size, and ¾-size models. …

The Business Of Writing

Trixie Mattel, a contestant on season 7 of RuPaul’s Drag Race, has become one of the franchise’s most successful alums. Her coffee table book (Co-authored by comedy partner Katya Zamolodchikova) became a New York Times bestseller, the duo’s bonkers YouTube series led to a Netflix deal, and her wildly overpainted face — a commentary on the unrealistic facial proportions and beauty standards of barbie dolls — has birthed its own makeup line.

When discussing the show as a visibility platform, Trixie notes that

“The real race begins after the show has aired.”

She was referring to how well contestants leverage…

Apps

A few weeks ago, I did a TV interview to break down Clubhouse, the hot new live audio app whose invite-only distribution strategy is eerily reminiscent of the cool kids’ table in a school cafeteria.

While sitting in the virtual green room with the producer, I was surprised to hear him say no one at the station had even heard of the app yet. Over here in my entrepreneur bubble — where you have to take a drink every time someone says “zone of genius”, “niche”, or “six figures” — I never stop hearing about it.

The hype is undeniable…

The Business Of Writing

Having your book become a New York Times bestseller is an astonishing feat, an achievement that usually cements your career and future as a successful writer. At the moment, however, author James Clear appears to be on a different level: His debut book, Atomic Habits, has sat on the advice and how-to list for 65 weeks as of this writing, demonstrating remarkable relevance with people worldwide who want to get better and improve their lives.

Bestseller lists can sometimes be curated or suspicious. …

Career Handbook

People hate a lot on Lululemon (And rightfully so at times), but I’m grateful for my time there. In 2010, I was 22 and having a substantial meltdown at music school; entry-level retail turned out to be a saving grace. Success was achievable — fold yoga pants and clock in and out on time — and steady paychecks were a welcome respite from the starving artist lifestyle.

What I thought would be a temp job for a few months ended up being my first stint in management; I stayed for about four years. …