#AMA female fashion tech startup founder wearing many hats with previous lives in consulting for DoD, Venture Captial, and Digital Marketing. I❤helping entrepreneurs.

Gemma Sole
Mar 13, 2018

I was born to curate and build. Anthropologist-turned-strategist, I live at the intersection of creativity, technology, and operations with Nineteenth Amendment. Graduated from the University of Rochester with two degrees and a Kauffman Foundation company then went to work as a consultant for one of the largest organizations in the world - the Department of Defense - to working with startups. After starting a vc-backed company in the caregiving space in Boston, I met my cofounder, designer Amanda Curtis, and went on to launch Nineteenth Amendment, an on-demand marketplace for fashion made in the USA. I want to see businesses + brands grow by bringing beautiful products to consumers who understand their value. Named one of Forbes’ top 30 under 30 in 2016 for retail and e-commerce, Apparel Magazine 30 Under 30, and one of 25 retail influencers by the National Retail Federation in 2017. #AMA about startups, digital marketing, retail, ecomm, tech product management, oysters :)


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Before you became a business owner, what was your favorite among the jobs you’ve had?
Mar 20, 3:26PM EDT0
What’s it like being a business owner and having to delegate tasks to employees? How do you start trusting people who are basically strangers you chose to hire?
Mar 20, 2:59PM EDT1
Do you only help American fashion entrepreneurs, or do you look internationally?
Mar 20, 3:50AM EDT0
You said you did a program called Startup Institute, could you elaborate on what that is and what you did there.
Mar 19, 6:11PM EDT0
How do you choose team members to work with? Is it important they share your vision?
Mar 19, 8:20AM EDT0
Do you feel that studying is useful for the entrepreneur, or is it more about getting in, backing yourself and having a go?
Mar 19, 8:16AM EDT0
Do you think business skills or creative talent is more helpful for entrepreneurs?
Mar 18, 2:30AM EDT0
If there is one thing you would advice enterpreneurs against, what would it be?
Mar 15, 8:01AM EDT0

Hmmmm one thing is hard! Here's a few:

- Don't take things personally.

- Be cautious when deciding to work with close friends or family.

- Make informed decisions fast. Time is not your friend.

Mar 19, 9:20AM EDT0
Do you enjoy being a business owner more, making the tough decisions or do you liked it better when working as part of a team?
Mar 14, 4:35PM EDT0

Good question - but not sure those are mutually exclusive. We always work as a team.

That said, I do like having the power to make decisions and choose the way forward but you can be a leader in a team setting as well.

Certainly decisions feel a lot bigger when you are the owner...

Mar 15, 8:19AM EDT0
What is a sure way for a new idea or project to get necessary funding? Do you have a checklist of items that must be present to impress investors and convince them that they should take a chance on you?
Mar 14, 11:17AM EDT0

Great question!

So...there are certainly topics or areas that become trendy for investors. For example, AI and blockchain are very "sexy" to investors at the moment. That said....a lot don't have a terribly deep understanding of either. So there is opportunity to ride that wave, but hopefully everyone around the table knows what they are talking about.

In terms of materials to have before having conversations with investors:

- A deck is a must

- A pitch (paragraph)

- A team 

- An MVP - minimum viable product or some proof this works/is a good idea

- A good lawyer and a term sheet

After that, it's a lot of sales!

Mar 15, 8:22AM EDT0
Your achievments are certainly impressive but what are some of the failures you had to go through to get where you are today? How did they change the way you do business?
Mar 14, 11:13AM EDT0

I graduated in 2009, so not being able to land a "job" then definitely felt like a failure after 4 years of college...the reality is A LOT of grads that year did not find employment. I had kind of seen the writing on the wall during interviews during winter 2008 so I decided to put wheels in motion to start a business in upstate NYC. It was an easy transition from graduation - didn't have to move, I got a grant from the Kauffman foundation which helped provide additional impetus, and I had something to work on. I love building things. So instead of boo-hooing at graduation (although there may have been some of that :) ) I was ready to move onto building something new.

It changed the way I operate because it was a big eye-opener in terms of understanding that you have to create your own opportunities.

Mar 15, 11:08AM EDT0
Which do you like better, the business side of the company or the creative one?
Mar 14, 10:07AM EDT0

Business is creative :)

I love both.

Although...I could probably leave accounting.... :P

Mar 14, 10:19AM EDT0
Why did you decide to go into fashion of all things?
Mar 14, 8:29AM EDT0

Hi Petar452 - this is a great question. Honestyly didn't imagine myself there but the opportunity I saw was too good to turn away from. I decided to pursue the business because I couldn't convince myself it wasn't an amazing idea and model. Luckily, other people think so too like our investors, over 500 designers who have worked with us, and industry experts like our partners at the CFDA, the National Retail Federation who named us Influencers of the year in 2017, Forbes30Under30, and Apparel Magazine. It feels like now is the time for a fashion industry reboot for sure.

I also think what we do at Nineteenth Amendment is very business process and software focused...so it doesn't totally feel like fashion - although we do securely straddle the fashion and technology sides.

Last edited @ Mar 14, 10:44AM EDT.
Mar 14, 10:42AM EDT0
How do you help other enterpreneurs with their start-ups? Is there a process? How do they get in touch with you? Do you charge a fee?
Mar 14, 5:31AM EDT0

Hi Anastasija - great question.

At Nineteenth Amendment, I help fashion entrepreneurs every day create, launch, and grow on-demand fashion businesses with #stilletostrapping. To join to for designers, it's just $19.99 a month and they get a digital tech pack builder, access to no minimum manufacturers in the US, discounted services like photography, and free PR and Marketing on behalf of their brand with the option to sell on the platform. It's a pretty kick-a** deal IMHO. You can learn more here.

Outside of Nineteenth Amendment. I just joined the board at my alma mater's entrepreneurshiper, the Mark Ain Center for Entrepreneurship at the University of Rochester, so a lot of what I am doing at the moment is through that including, judging business plans and competitions, volunteering time with student entrepreneurs, coordinating programing, etc.

I also generally will speak with entrepreneurs who ask for help - usually something pretty specific! I don't charge a fee to chat :)

Linkedin is a good place to start to get in touch :) 

Mar 14, 10:40AM EDT0
Did you have a difficult transition from the DoD to start up your own business?
Mar 14, 3:39AM EDT0

Great question! By the time I left consulting I felt I had grown as much as I could there so I was ready. When I moved up to Boston, I actually did a program called Startup Institute (previously called Boston Startup School) to help individuals get into startups. I spent 6 weeks meeting the Boston startup community, updating some skills, networking, etc and that's also where I met my cofounder, Amanda.

It wasn't difficult per se but it was a bit scary. When I first started working with Amanda on Nineteenth Amendment I was looking for a fulltime job as well. Doing both kept me sane, and once I got a job in Venture Capital, I was able to support myself and save $$ which is crucial to do before you jump in!

Mar 14, 10:29AM EDT0
If someone is setting up a startup and wants to market their product, would you advice them to do it themselves to minimize the cost or hire a professional?
Mar 14, 3:38AM EDT0

It kind of depends what you are trying to do and the resources you have.

However, generally I think you will be able to do it yourself most cost effectively and the way you want. There are a lot of ways for people to sell products or services or their startup online - it just requires a lot of time and dedication.

If you do decide to work with someone as a vendor, make sure you get lots of recommendtions from them of past clients and give them all a call. The best case is finding someone who has done before what you want done...but there are a lot of horrible vendors and smoke and mirrors so watch out!

Mar 14, 10:22AM EDT0
What are the major challenges one could face when starting a company?
Mar 14, 3:06AM EDT0

Fundraising is always a timesuck and a challenge.

Hiring and vetting vendors is probably just under that.

And probably one not often talked about is the emotional and personal side. It's a bit of a roller coaster ride emotionally. And if you don't have a supportive partner or family it can be a very lonely place. I think you learn how to deal with those emotions over time as you grow as en entrepreneur but no one really warns you about it...consider this a warning :)

Last edited @ Mar 14, 10:25AM EDT.
Mar 14, 10:24AM EDT0
Do you have physical presence? Stores etc. Would you consider it?
Mar 13, 12:27PM EDT0

Hi Faith! We do a lot of pop up's and store partnerships but we do not have a permanent physical presense at the moment. The overhead isn't totally worth it for us quite yet...

We do do a lot to leverage our retailer partnerships however and have done pop ups in Macy's Herald Square (see below), Lord and Taylor in NYC, independent boutiques in NYC, our own pop ups in Boston and NYC, and shoppable runways all over the country usually run by our designers. If you're interested in getting involved or having one near you definitely shoot us an emai!

Below is an image of our Nineteenth Amendment People pop up at Lord and Taylor!

Mar 13, 5:29PM EDT0
What is the best selling brand and/or item at the moment on the site?
Mar 13, 8:25AM EDT0

That's a great question AnaS! We launch a new collection in pre-sale every week so at any given time it is usually the pre-sale or tied to an event. We just launched a Chicago-made brand called ENA Apparel. They do ethical #sweatshopfree athliesure you can actually sweat in. Super cool and flattering - they are a big seller this week and everything is under $100. Check them out here!

Mar 13, 5:25PM EDT0

What is your next big aim, what are you racing towards?

Mar 13, 12:24AM EDT1

Hi Anna! Great question! Our next big aim at the moment is fundraising. We are currently raising our Seed round. It is definitely a race and considering female founders raise only about 3-4% of venture funding....the odds are staked against us...but we are one of the few female founded companies who have done it before so I am certain will close :)

Mar 13, 5:23PM EDT0
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