Serving 160k Customers Custom Fit Fashion with Jess Fleischer, Son of a Tailor (episode 456)

Jess Fleischer is the Co-Founder & CEO of Son of a Tailor, a clothing technology company making custom-fitted casual clothing for men. Founded in 2014 they’ve served over 160,000 customers so far.

Jess Fleischer Son of a Tailor on eCommerce MasterPlan Podcast

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Dive in:

[03:35] eCommerce transformed fashion supply chains, sparking change.
[07:51] Small brands need to address sustainability issues.
[11:02] P2P businesses increasing.
[15:34] Challenges of customer onboarding process in business.
[18:21] Video ads on Facebook showing website checkout process.
[22:44] Entrepreneurs should start with non-online options.
[26:30] Keep it simple, no need for calculations.
[27:28] Fashion sustainability: streamline supply chain, increase profits, inspire others, improve customer experience, and use social proof.

Jess and His eCommerce Journey

Jess entered the world of eCommerce through two main avenues. First, he gained experience working for eBay, and second, through his background in manufacturing.

He says his main motivation for starting his own business was the belief that eCommerce and manufacturing could be combined in a more innovative and efficient manner. This ultimately led him to establish his business.

About Son of a Tailor

Son of a Tailor began with a focus on creating perfectly fitting t-shirts. This was due to his own frustration with ill-fitting clothing. He also noticed inefficiencies in the fashion industry’s supply chain, which relied on long and complex processes.

He believed there was a need for a more sustainable and efficient approach. Son of a Tailor’s innovation lies in combining technology and manufacturing to provide custom-fitted clothing to customers. While they’re often described as a “clothing technology company,” Jess considers them primarily a supply chain builder.

Inspiring Change in the Fashion Industry

Son of a Tailor wants to encourage the fashion industry to be more sustainable and better at managing how they make clothes. Jess knows that because there are many small brands and a few big ones in the fashion world, just one brand like theirs can’t make a big change alone.

Their goal is to serve as a source of inspiration for other brands. Jess suggests that brands that want to be more sustainable should start by finding their niche and excelling within it. Instead of trying to do everything at once, they should do one thing really well and tell others about it to inspire them.

User-Friendly Experience and Social Proof

Jess admits it can be hard to get the customer to purchase the first, so it’s important to make their ordering experience fast and straightforward. Son of a Tailor’s success hinges on creating a user-friendly experience for customers navigating the custom ordering process. 

Additionally, positive media coverage and social proof, such as endorsements from reputable magazines, significantly enhance credibility and trust in the brand.

Stay Committed to Your Core Values

A key takeaway from Jess is the importance of staying true to core values and goals, even when facing challenges.

In the case of Son of a Tailor, they never switched their focus. Jess believes it’s important to keep working on your mission until you succeed, especially if you’re making things better for customers and the environment.

eCommerce Book Top Tip

eCommerce Traffic Top Tip

  • Jess doesn’t have a specific magic traffic source to recommend at the moment, noting that traffic sources tend to come and go in effectiveness.

Tool Top Tip

Carbon Top Tip

  • Only make what you can sell or don’t buy too much inventory.

Interview Links

Related episodes

  • Championing Sustainability Through Seasonless Fashion with Lyndie Benson, Bleusalt (episode 434)
  • The Fashion Business Model of the Future? This is Unfolded with Cally Russell (episode 381)
  • Growing a sustainable fashion business to 7-figures with Encircled’s Kristi Soomer (episode 337)

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