Gemma Sole

If you can’t express it in words, it can’t scale or get done by someone else.”


Gemma Sole was born to curate and collect. As an anthropologist-turned-strategist, Gemma lives at the intersection of creativity, technology, and operations with Nineteenth Amendment. Having graduated from the University of Rochester with two degrees and a Kauffman Foundation company under her belt, she went to work as a consultant for one of the largest organizations in the world – the Department of Defense – with Booz Allen Hamilton to working with startups. After starting a vc-backed company in the caregiving space in Boston, she met her cofounder, designer Amanda Curtis, and went on to launch Nineteenth Amendment, an on-demand marketplace and manufacturing service for fashion made in the USA. With a background in consulting, venture capital, and product development, she is used to playing many parts. And figuring out how they fit together. Gemma wants to see brands grow by bringing beautiful products to consumers who understand their value. Gemma was named one of Forbes’ top 30 under 30 in 2016 for retail and e-commerce and one of 25 influencers by the National Retail Federation in 2017.

Where did the idea for Nineteenth Amendment come from?

Back in 2012, I had just left the consulting world and was learning about lean startups and MVPs (minimum viable products). I met my cofounder, Amanda Curtis, who was a designer at the time and we started to think about how you could apply the concept of MVPs to fashion. So how could often cash-strapped designers launch a brand or product with the least amount of cash required and Nineteenth Amendment was born!

What does your typical day look like and how do you make it productive?

Coffee. On the typical day I am traveling usually so it’s easy to be productive when you are up at 7 am to catch your bus. When not traveling, I like to get a quick workout in and then start going down my list. We do digital standups on slack and then I have a very time locked day of calls and deliverables. I know how long most things should take these days so if I’m going over my allotted time, it means I am distracted or need a break.

After lists and check ins, I am usually speaking with new designers on Skype to do brand consultations. Around noon I will review analytics across various channels to check on different tests. Then I try and reserve the afternoon for creation of things, whether it’s marketing content, sales decks, or strategy docs. Usually there is a meal and glass of wine in there somewhere then back the computer for late night product tweaks or last minute to-dos of the day.

How do you bring ideas to life?

Writing them down. I am a big believe in documentation and communication. If you can’t express it in words, it can’t scale or get done by someone else.

What’s one trend that excites you?

On-demand. It’s permeated everything but I am especially excited about on-demand fashion and how it can allow us to reduce waste in an industry that generates the second largest amount after the oil industry.

What is one habit of yours that makes you more productive as an entrepreneur?

I like documentation of things and digital organization. I had an early consulting gig in information management and I have unusual tendencies to document and store everything in easily retrievable ways. A person who does documentation well can be 10x more efficient over time and is usually a better colleague and manager.

What advice would you give your younger self?

Follow your gut more. Take that chance now before it gets harder and while you are covered by someone else’s health insurance!

Tell us something that’s true that almost nobody agrees with you on.

[Great question.] Glitter is amazing, not annoying.

As an entrepreneur, what is the one thing you do over and over and recommend everyone else do?

Make lists! Document things (see above). Work out regularly.

What is one strategy that has helped you grow your business?

Early adopt everything. My cofounder and I have jumped on new platforms pretty early….we used an early direct video messaging app (since closed) that allowed us to DM videos via twitter pre-snapchat/instagram. We used it to do targeted outreach B2B. It was great and helped open doors to some new business for us. We were early on Periscope as well, also defunct. The lesson is not every platform lasts but no matter what you usually always learn something helpful to your business. All this video practice has helped us lose any camera fear and we now product one LIVE piece of content a week with zero production budget. It’s empowering.

I also was fairly early on Quora and invested heavily up front in answering questions where I felt I could add value that also related to our business. I am now one of the most read in Fashion/Retail and it has generated a lot of leads for us.

What is one failure you had as an entrepreneur, and how did you overcome it?

Not vetting vendors and employees enough. We have gone off of recommendation data points before but after a bad experience, I have started to get almost stalker level of vetting. Lousy vendors beware!

What is one business idea that you’re willing to give away to our readers?

A glass-door for digital vendors and SaaS service providers. DM me if you want to work on it!

What is the best $100 you recently spent? What and why?

$100 dollars on dollar oysters to share for Nineteenth Amendment’s monthly 19th Day. On the 19th day of every month, we celebrate! As a team, Nineteenth Amendment does dollar oyster happy hour rather than beer happy hour. It’s delicious and the most efficient way to get protein.

What is one piece of software or a web service that helps you be productive? How do you use it?

I’m loving the kind of new Google Docs intelligence “Explore” feature. It basically will automatically read your spreadsheet and spit out observations about the data. It’s great if you want to do quick reporting with almost zero effort. Plus it automatically create graphs which – when working with creatives – is crucial.

What is the one book that you recommend our community should read and why?

For amazing pleasure reading – “The Rules of Civility” by Amor Towles
For classic business reading -” Ogilvy on Advertising “by David Ogilvy – there are some gold nuggets of business wisdom in there.

What is your favorite quote?

No matter where you go, there you are” – from the AWESOME 80s movie The Adventures of Buckaroo Banzai Across the 8th Dimension.

Key Learnings:

  • Listen to your gut.
  • Vet your vendors excessively (#trolling)
  • Document everything to make your life easier. Your future self will thank you.
  • Try/test new technologies early on if you are a founder – it can only help!
  • Eat oysters.


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