The Short Stack 🥞 Vol #27

First emailed to newsletter subscribers on June 24, 2017

Good Morning All ✌️

Hey guys — Anthony here!

I haven’t written the newsletter intro in some time, and I’m excited to take over this week with some new perspective. Speaking of, the theme of this week’s Short Stack is just that: perspective.

Leaving NYC always lets me see things from a different light. I’ve left New York twice these past two weeks, and I’m here to share two unique experiences. The first is about LA. The second is about prison.

Last night, an entrepreneur friend of mine whom I’m staying with in LA turned to me and said: “you’re addicted.” Sitting at his kitchen table, I was on my computer catching up on emails and finishing other EOD tasks. Caught off guard, I looked around to realize I was the only person not prepping dinner or enjoying wine. While they were cooking and conversing, I was working. Why? Was anything going to change at Jakt over the next few hours? Probably not. If it did, was my immediate reaction going to be important? Not likely. So I decided to break old habits, shut my computer and enjoy the company of friends — friends I haven’t seen, and might not see again, in over a year.

NYC can be a challenging place to shut down, and it’s far more likely you’ll find busy professionals cooking dinner and relaxing in LA. But we must all learn to “turn off,” get present and appreciate the moment. So this weekend, take the time to slow down and gain a new perspective — wherever you are.

Last night’s dinner has me feeling energized and productive today, even though the previous week I went to prison. Yes, prison. Read on to learn about my time volunteering at Rikers Island, and check out my latest video, too.


Making Movies 🎬

Episode 027, by our CEO Anthony Tumbiolo.

Inside the episode:

  • Adjusting to shorter meetings and calls to be more efficient with time
  • Iterating on our development process with Anthony Guidarelli
  • Anthony and Mike talk breakdowns and getting back into “flow” state
  • That “not working” feeling even when you’re always working

Thoughts 💭

☝️ Here are the things we’ve been thinking about this week.

Starting on 3rd Base: Last Week I Went To Prison

Last week I went to prison. Yes, you read that correctly. I spent the day at Rikers Island Correctional Center with Defy Ventures for their Deep Dive event, which empowers underdog, aspiring entrepreneurs in jail. The experience was eye-opening, to say the least. Many of you have asked about it, so I figured writing a blurb in the newsletter would be a good place to share my thoughts.

A couple of months ago my friend Sam Hysell told me about Defy Ventures. After reading their mission, I had to be involved. I’ve been an entrepreneur my entire life, and I’ve grown to love helping other entrepreneurs. As most of you know, a significant portion of our business at Jakt directly involves working with startups. So when I learned of the opportunity to help inmates eager to improve their lives through entrepreneurship after being released, I was in.

I went in thinking I’d be the teacher, but in retrospect, they showed me more than I could ever show them. The word that keeps coming to mind when thinking about my experience and what I learned is perspective. I’ve worked hard to get Jakt to where it is today, and like many entrepreneurs, put in 80+ hour work weeks consistently for the first several years. I started my company with just $500, and I’ve had real struggles along the way; divorced partners, lost customers, and the sleepless nights and stress that come with the ups and downs of running a business.

I’ve always operated under the assumption that if you were born in the US, anything could be achieved through hard work. While I still believe hard work is the answer to getting most anything you want in life, going to prison reminded me that I started my entrepreneurial journey on 3rd base. My journey started from the advantageous position of being from a white, middle-class US family. My childhood was good. I lived in a safe neighborhood, had access to great schools and never really worried about from where my next meal was coming. Volunteering at Rikers reminded me just how much I have to be grateful for, and how lucky I am.

The men I met in jail didn’t grow up the same way. I can’t claim to know any of their stories intimately, but from the moments I did spend connecting with inmates, I gathered that most their childhood situations were far different than mine. When we aren’t all on the same playing field, society loses. Some people get lucky, like me, and they’re born into a healthy situation. I didn’t do anything to deserve that — I got lucky. Others, simply do not. We don’t need to look further than basic demographic information, starting with ethnicity. Did you know that black Americans are 5x more likely to be incarcerated than whites? Yes, I started on 3rd base.

Here are some words that come to mind when thinking about the men I met at Rikers — kind, enthusiastic, positive, passionate about bringing joy to others, thirsty for knowledge, and eager for improvement at all cost. Do these sound like people that aren’t interested in contributing to the community?

As a society, we have the opportunity to make a difference, even if at times the problem may feel too large. I think what Defy Ventures is doing is great and I plan to stay involved. To learn more about Defy Venture’s work and meet some grads who turned street hustle into legal startups, click here.

Further reading — Last month, I went to prison. Next month, I’ll return.

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