Cladwell: Personal Styling Service


Personal styling service and app that teaches you how to live with a capsule wardrobe. The app generates daily outfits for you based on your clothes and the weather.


Cladwell was Differential’s first client and investment. At the time, it focused on helping men dress better.

Erin joined Cladwell in 2014 as the head of marketing as they were about to launch their first product for women, and needed to start charging for their products.

In 2016, I helped Cladwell run a few design sprints which led to a decision around building a mobile app. Cladwell was accepted into the 500 startups program (batch 17) and I joined as a fractional CTO.

Erin was granted co-founder status during this company repositioning, and I continued to help and advise as I could. The company ended up raising around $3.5M in total.

Cladwell was vying for the VC billion dollar path and with its last lead investor Science Inc, decided to go through a round of pivots in order to look for the big opportunity. These included going FREE, trying to add a social component to the product, as well as selling clothes. None of the options made a large difference in the business’s numbers, and the bank account and funding options were giving the company very little time.

In August of 2019, Erin and I were fortunate enough to be able to pool enough resources to acquire the majority of the assets of Cladwell from the investors in an effort to keep the business alive and to give it another shot.

In February 2020, we raised a small round of funding from (v4) and have been rebuilding the offering and business since then.

Erin is the CEO, I lead the operations and finances, and we have a few employees and a team of contractors.

Investment Thesis

A Universal Daily Habit

Every person gets dressed, every day. The majority of people don’t enjoy that time. At P&G, I learned to look for businesses that had a frequent touch point to your brand. Cladwell has that opportunity with your closet.

Capsule Wardrobe / Minimalism

I believe that we waste too much stuff and our world (and minds) can sustain the same pace we have been running at for decades.

A Capsule Wardobe can bring calm to people from their closet. It removes clutter (and decision making) so that each person is more free to decide for themselves what’s important.

Consumer Subscription

I enjoy businesses and brands that can solve a problem directly for their customers.

We are selling a service on a recurring basis ($5 a month). Recurring revenue businesses start slower but compound in value faster and provide a steady stream of revenue.


Consumer Software Services
Personal Styling


October 2014 - Current

How did it work out?

Since acquiring in August 2019, we have stabilize and grown revenue modestly, while rebuilding the technology for stable growth moving forward.

What did you learn

Acquiring a business is hard.

It’s an understandably very emotional process for the sellers and an  anxiety filled risk taking venture for the buyers. In times of high stress and many stakeholders, people don’t always bring their best selves to the table.

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