Bill D'Alessandro

What I learned from biggest wins and losses of my career

Published 5 months ago • 3 min read

Mid-January is a great time to be extremely transparent, right?

Every entrepreneur has wins and losses. Nobody’s having a perfect career, and they’ll all be the first people to tell you that. I’m no different. So today I want to share a few of my biggest wins and losses with you.

Social media can make it seem like everyone is on an incredible winning streak, but I want to pull back the curtain and show you some of my struggles — and what I learned along the way.

My biggest loss: Not going hard enough on the ecommerce aggregator model

So when I introduce myself to other people, I tell them I founded Elements Brands and pioneered the ecommerce aggregator model. The truth is I’ve always hated the word “aggregator”, but it’s the easiest way to explain what I did. We rolled up eight brands from 2013-2018.

My big miss was not raising a ton more money than I did to support this model.

I was early — like, five years early — to the ecommerce aggregator model. This was a time where you could buy brands for 3x EBITDA, and there were tons of them.

I should’ve raised $50 million and called in every favor I had. Don’t get me wrong, I’m happy with the way things have played out — but Elements could have been the size of Thrasio, which did the same thing and was valued between $5-10 billion in 2021.

Thrasio is in a tough spot now, which ironically makes me frustrated that we didn’t go even harder to compete with them. Thrasio raised a lot of money and bought everything in sight. They didn’t buy real brands — like dotcom consumable product brands — they just rolled up every brand who would sell and used a ton of debt to do it.

I felt like we had a better thesis — buy real brands that have strong products and staying power, and focus outside of Amazon — and I absolutely missed a massive opportunity to go harder.

The lesson: When you’re right, it’s not enough to be right. You have to go hard. I’m not saying to ever go all-in and pretend there’s no risks. I was very right, and I didn’t go as hard as I should have.

My biggest win: Personality profiling in hiring

Michael Girdley, my Acquisitions Anonymous podcast cohost, introduced me to personality profiling a few years back.

I’m not exaggerating when I say it changed my entire business. But if I am exaggerating, it potentially changed my life.

We used a company called Culture Index. They surveyed every employee at our company, and then spit out charts with patterns for our HR director. At an offsite, she brought the charts with names removed and had our executive team identify common patterns that occurred in all the charts.

We each took a few minutes and circled the patterns we saw with our pens. There was a trend that all the charts she showed us had two things in common. Then she revealed the names with a flourish - there were identical patterns in all the charts for everyone at our company that had either been fired for cause or put on a performance improvement plan.

My jaw hit the floor.

If we had been using personality profiling during our hiring process, we could have predicted these misses. Now, we incorporate it at the top of our hiring funnel - everyone who applies is personality profiled to ensure they are a fit not just for our company, but for the specific role they’re hiring for. Our hit rate has gone through the roof, and our culture is better than ever before. Using this on the front end has completely changed the company.

And lest you think I’m exaggerating when I say it changed my life too - you may know I have a fantastic COO Brian, who I’ve worked with for 7 years. I’ve been married to my wife Natalie for 5 years. Both of them are incredible people and wonderful compliments to me. After personality profiling both of them I learned - they both have the exact same Culture Index profile :)

What are your biggest wins and losses in your career? Reply and I’ll share the best ones in an upcoming newsletter.

If you liked this newsletter, I have 4 places where I share more like it:

  1. 👔 The 1-1 coaching that I do with CEOs (I currently have ONE slot open).
  2. 🐦 I tweet (a lot) - follow me @BillDA.
  3. 🎙️ My podcast, Acquisitions Anonymous, where we break down real businesses that are for sale.
  4. 📬 This weekly newsletter! Click here to subscribe and read past issues.

Until next time,
Bill D'Alessandro

Bill D'Alessandro

I've been an entrepreneur my whole life - now I coach others.

Join my newsletter and I'll send you non-public stories, tales from the ecommerce trenches, and even opportunities to invest in private deals with me.

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