Biggest Wins and Losses from 15 Years in Business

Ever wondered about the highs and lows of being in the eCommerce game? In this episode, I’m joined by the one and only Bill D’Alessandro, arguably our most frequent co-host, for a candid conversation on our biggest wins and losses in the business world. Together, we dive into the significance of strategy, size, and timing when thinking of buying and the critical role of having a niche.

Listen in as we share our three biggest wins and our three biggest losses, including one of the biggest misses of Bill’s eCommerce career. He also shares what it’s like to sell seven brands at once (and the approach he took to manage the sales), how to use personality profiles to hack your hiring process, and why sometimes timing is everything.

You’ll learn:

• One of the biggest misses in Bill’s entire career. (7:30)
• What ultimately went wrong with Thrasio. (9:45)
• My biggest loss in this business. (11:15)
• The common paid ads trap Bill fell into with his business. (14:20)
• The pitfall of trying to do too much at once. (17:25)
• Bill’s most acute loss so far and how it changed his perspective. (21:00)
• One of Bill’s biggest wins. (30:35)
• Being consistent with growth as a win. (32:50)
• Buying a brand at exactly the right time. (34:50)
• One of the top three hacks Bill discovered to hire well. (41:30)

Subscribe: iTunes | Stitcher | Amazon

(With your host Andrew Youderian of eCommerceFuel.com and Bill D’Alessandro of NaturalDogCompany.com)

What Was Mentioned

• Bill D’Alessandro: Website | Twitter | Podcast
• NaturalDogCompany.com
• Quiet Light 
• DiSC
• Kolbe
• Culture Index
• The Defining Decade: Why Your Twenties Matter–And How to Make the Most of Them Now by Meg Jay
• One Click Upsell – Increase Sales 15%+ with Pre-and Post-purchase Upsells. (On average, Shopify users increase sales 15% immediately after installing the app!)