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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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Featured Post

My Perfect DTC Finance Stack - The 5 Best Options for Banking, Credit Cards, and More

Hey everyone, This week I'm writing about something I'm obsessed with - choosing the very best financial tooling for your business. Entrepreneurs love to hack on this stuff - credit cards, banking, lines of credit, and more. After years of research and testing countless options, I've finally nailed down what I believe is the ultimate finance stack for DTC ecommerce businesses. And today, I'm sharing it with you. Before we dive in, let me be crystal clear: none of these are sponsored mentions...

3 days ago • 5 min read

Twice each week, I break down real businesses for sale on the Acquisitions Anonymous podcast. What better way to learn about business than by studying real businesses each week? My favorite part about the podcast is the meta-lessons we learn that are more broadly applicable than just the business we are analyzing. That's what today's newsletter is about. Recently, my co-host Heather Endressen and I broke down a $2M EBITDA ecommerce business — I'm featuring it here not just because I love this...

2 months ago • 3 min read

We all know the typical ecommerce distribution models - DTC, Amazon, and Retail. Today I want to highlight two other ways businesses can reach their customers that you might not be thinking about, to help inspire you to diversify your own business: Influencer Businesses Here’s a common issue for many ecom operators: Facebook has been consistently decreasing organic reach, making you pay to reach the people who want to buy from you. I would not be surprised if one day Gmail will make you pay...

3 months ago • 2 min read
photo of bag, sneakers, and sunglasses on beige surface

What’s the first thing you need to solve for when you’re looking to start or acquire an ecommerce business? Product. Without nailing down the right products at the right margins for the right customers, your business is dead on arrival. If you want to play on easy mode (and I like playing on easy mode) the most critical thing is to make sure your product is ecommerce compatible — something that has the right characteristics and margin to make selling DTC (direct to consumer) work. Kayaks may...

3 months ago • 4 min read

I’m writing this from my new baby’s bedside as my wife sleeps - our third child was born a few days ago! Everyone is healthy and doing great, and now we are a family of five. My son is 4 and my daughter is 2.5, so I’m a few years into my journey as “dad”. So today, I want to talk about - how do you run a business while also raising young children? I admit there’s not a one-size-fits-all answer, but this is a topic I think about all the time — and something that’s generally under-discussed...

3 months ago • 4 min read
stressed out call center employee with three phone calls

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...

3 months ago • 3 min read
a traffic light with a street sign hanging from it's side

Did you really think I was going to let 2024 start without doing an ecom prediction email? If you like this email, I did an hour-long episode of the EcommerceFuel podcast with Andrew Youderian where I expand on these predictions. Andrew also has five of his own in the episode that I didn’t include here. But if you’re not a podcast person, here’s a rundown of 4 predictions for how I see ecommerce and the economy going in 2024. 1. Entry-level ecommerce jobs disappear due to outsourcing I think...

4 months ago • 3 min read
person writing on white paper

Welcome to 2024! I hope you had an awesome holiday season. The week between Christmas and New Year’s is one of my favorite times of the year. I cancel all of my meetings, sit down with my wife, and plan for what we want to accomplish for the year ahead - both business and personal. If you haven’t done this yet, it’s not too late! I want to share exactly how I do it. The way I start planning is to close my eyes and imagine that it’s this time next year — New Year’s Eve 2024. I ask myself all...

4 months ago • 3 min read
yellow red blue and green lego blocks

Merry Christmas! 🎄 I hope you had an awesome time with your family the past few days! This week at Natural Dog Company, we cancel all our meetings and encourage everyone to spend the week reviewing the year behind and planning for the year ahead. One of the main things we’re focusing on in 2024 is how we can make things easier. I asked everyone to think about this question — "What would work feel like if it were easy to do what you were good at, and nothing else?" Let me introduce you to what...

4 months ago • 3 min read
assorted-color gift box under Christmas tree

Hey Reader, this week I thought it would be fun to share some of my favorite things, and the items I give as gifts. That’s right - it’s Bill’s Favorite Things! I have zero financial interest in any of these, I just think they’re awesome. If you hurry, you can still get them in time for Christmas (all links are to Amazon when possible, exercise that Prime membership, baby). Let’s get to the list! Personal Items and EDC Gerber EAB Lite Folding Knife: The best knife is the one you have on you...

4 months ago • 5 min read
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