Why I'm Closing My Business - 34 Lessons from 5 Years of Entrepreneurship

Bring Ambition Newsletter - March 11, 2021

Hi folks and welcome aboard new subscribers!

This is a special edition of the Bring Ambition Newsletter. In this installment, I share the story of my first business venture and why, after five years, I've decided to close up shop. As a bonus, I'm including a ton of lessons learned (and the stories behind them).

As always, I'm also including several other interesting resources / stories / exercises.

I hope you enjoy, and if you'd like to help this newsletter grow, please share with a friend!

1.) 34 Lessons from 5 Years of Entrepreneurship:

"Why I'm Closing My Business (and Everything I've Learned Along the Way)." Here it is, the big shaboozie. After five years, I am shutting down Ambition Menswear, my first business venture.

Hitting 'publish' on an article is usually nerve-wracking, but this time it was terrifying. This is a deeply personal and candid look at why I'm winding down the business, including what I did right, where I screwed up, and everything I've learned on this long and winding road.

It's not easy to talk “failure,” or what people might interpret as failure. So why do it? To quote the article:

I wanted to tell the story of a business most people will never hear about. To define and digest some of the many lessons learned. To express gratitude for my customers and vendors. To show that it's ok to talk about "failure" and everything it teaches. To motivate you to create your own real-world MBA and embark on your own entrepreneurial adventure. To encourage you to be more thoughtful and intentional about when to bow out and move on.

This is a long read, so grab your favorite drink and buckle down. (If you're short on time, skip to the end for a consolidated list of all 34 entrepreneurship lessons).

I'm looking forward to freeing up more time for this newsletter and my blog. I hope you're enjoying both as much as I enjoy writing them.

2.) Self-coaching prompt of the week:

Here's a valuable but challenging self-coaching prompt to try.

It's borrowed from Acceptance and Commitment Therapy (ACT) and used both therapeutically and in the Performance Psychology context to help identify one's values.

What exactly do we mean by ‘values?’

Values are internalized cognitive structures that guide choices by evoking a sense of right and wrong (e.g. morals), clarifying priorities (e.g. achievement), and creating a willingness to make meaning and see patterns (e.g. trust vs distrust). Put simply, values are desired qualities of behavior.

Why does it matter?

We all have values - whether we realize it or not - and they guide and influence everything we do. Without aligning our goals to our values, we don't "feel good" as we progress. We're more likely to lose steam, hit plateaus, and fail.

So the first step to creating intrinsically motivating, value-aligned goals is to consciously identify your values. This prompt should help:


Imagine you're sitting in a crowded banquet hall, many years from now. There's a glass of champagne in front of you. You're surrounded by friends and colleagues.

It's your retirement dinner. A few people will step up to the podium to make speeches. They'll discuss you — what kind of person you are, what rules and values you lived by. "So-and-so was always ____," "They never did ____," for example.

What would you like to hear them say? What 4-5 qualities would you want them to discuss?

[Having trouble? This page provides helpful examples of values and beliefs.]

3.) Podcast of the week:

"The Tim Ferriss Show #501 with Steven Pressfield." If you've been following my newsletter or blog, you'll know I'm a huge fan of both Tim Ferriss and Steven Pressfield. This discussion goes deep into topics like:

  • The Hero's Journey vs the Artist's Journey

  • Accumulating "little successes" to fuel productivity

  • Overcoming resistance and self-sabotage

  • Best-practices for writing both fiction and nonfiction

  • "Shadow careers," and much more.

Best quote of the podcast:

"Don't insult the Muse with small ambitions."

4.) Pictures of where we'll be living in ~40 years:

"NASA's Perseverance rover sends stunning images." This past February, after seven months of interplanetary travel, NASA's Perseverance rover landed on Mars. This article features some stunning, uncanny images of the planet's surface.

If you're confident in Elon Musk's prediction that humans will live on mars by the 2060s, now is a good time to scope out real estate.

5.) Gin-soaked raisins:

No, this is not my band name. It's a 105-year-old woman's secret to longevity, according to a NYT article. She claims the fascinatingly random concoction, in conjunction with prayer and healthy food, helped her not only live over a century, but also beat COVID-19.

Cue the nationwide raisin shortage.

I'd love feedback on this newsletter. What did you enjoy? What's the worst (or most boring) thing about it that needs to be fixed as soon as possible? Reply here, or you can reach me on Twitter or Instagram.

Have a great weekend!

Jon D'Alessandro

Blog | Instagram | Twitter | Contact

P.S. - Tell your friends about this newsletter!

Share The Bring Ambition Newsletter