Makings of a Rebel CEO

About Bill DAlessandro

Hi it’s Bill โ€” I’m your host and Founder/CEO at Elements Brands. I focus everyday on creating products that people love, and hacking the system to get them in front of as many people as possible. My love for entrepreneurship started when I was 6 years old and hawked my first cup of lemonade on the street corner. Since then, I’ve sold everything from t-shirts to a software company, and been an investment banker, tech nerd, stock boy, even a college professor. Read on below to find out how I got here…

Quick Overview

  • I decided a long time ago that I won’t spend my life driving a cubicle.
  • I have a pretty ambitious list of things to accomplish before I turn 30.
  • I live in Charlotte, NC, but work and play wherever there’s internet and a laptop.
  • I’m an Eagle Scout.
  • I once lost 37 pounds using modified techniques from The 4-Hour Body.
  • I’m originally from Charlotte, North Carolina and am a southerner at heart.
  • I love to camp, hike, ski, and eat pulled pork BBQ.

My Background

Bill on Wall Street

Yes, I actually took this incredibly cliche picture.

I’ve always had the entrepreneurial bug. In high school, I progressed from lemonade stands to running a computer repair business during the summers that paid me more pocket money than I ever could have made waiting tables. During college, I helped start and eventually sell a software company called Groupvine that made running and organizing college groups easy.

After graduation I did what all the other ambitious kids were doing and took a job in investment banking. I’ll spare you the gory details, but suffice it to say – I learned a ton but hated the 100 hour weeks. I left investment banking after almost 2 years to take over Corporate Development and M&A at My day job was to acquire other hosting companies and combine them into our operations. However, that’s not what I spent all my time on…

Elements Brands (My Company)

While working at, I read Tim Ferriss’s “Four Hour Work Week” and became fascinated with consumer products. I spent my nights and weekends creating my first product, and launched it in late 2010. Since I had a full-time job (and also because I’m obsessed with process design), I used a combination of custom-built software and outsourcing to obsessively automate the business’s ordering, billing, fulfillment, marketing, and accounting from day 1. The business ran and grew almost totally autonomously during the first year – it was more like the one hour work week. ๐Ÿ™‚

Bill at the Continental Divide

When you live in Colorado, this is a day trip.

As my first product continued taking off, I was able to quit my full-time job in Spring 2012 and focus full time on growing my business. I have since launched and acquired several other brands to leverage my processes and automation platform. Over time I hope to build a company that’s one part Proctor & Gamble, one part Berkshire Hathaway, and one part 4HWW. I am always looking at opportunities to acquire or work with niche consumer products brands that need e-commerce, process, or marketing help to grow. I’m also available for consulting to brands that want to scale their business to the next level or need help with automation to keep up with their growth.

Through it all, I’ve become an expert in all aspects of the consumer products value chain, from product design to e-commerce to fulfillment and more. Rebel CEO is my philosophy on life and business – just because someone tells you something is done a certain way, doesn’t mean it’s the only way. I’ll use this website to pull back the curtain on an obsessively automated e-commerce business, and hopefully we’ll all learn something from each other.

Other Highlights

Matchbox Labs – a 4HWW incubator for undergrads

I took the expertise I developed running Elements Brands and created Matchbox Labs, a consumer-products focused, “Four Hour Work Week”-style college course/incubator for undergrads. I teach students that you don’t need a computer science degree to start a company, and help them design branded, scalable, cash flow positive e-commerce businesses. The first class of companies launched from CU-Boulder in Summer 2012.

Table’s Ready – text paging for restaurants

Somehow during all this I also founded and programmed – it’s a web app that replaces annoying restaurant “buzzers” with text messages. When a party’s table is ready (get it?), they receive a text message letting them know it’s time to return to the host stand to be seated. The app also captures statistics the restaurant can use to accurately staff and predict wait times.

Contact Info

You can get in contact with me in a bunch of different ways over on my contact page.

Thanks for reading!
โ€” Bill