Matt Stinchcomb is scrappy. He learns by doing.

He used this approach in his efforts at music and screen printing, and eventually when helping to start Etsy, an online marketplace for crafts and vintage goods. As the former VP of Values & Impact and former CEO of Etsy Ireland, Matt has been in the mix since the company’s inception.

He is now leading a new project,, a non-profit educational offshoot, for which he is designing a unique curriculum. What he’s calling a “regenerator,” is dedicated to guiding entrepreneurs through a fellowship focused on wisdom and long-term strategy.

The program will be in an immersive 12-week semester complete with classroom learning, business mentorship, and funding for the enterprises selected.

He seems a good man for the job, having been instrumental in Etsy’s growth out of an apartment in 2004 to an IPO valuation of $1.8 billion this April.  Just as important, he has the energy, curiosity, and comforting presence of a great teacher and guide.

Matt and I talked at the new headquarters in Brooklyn’s Crown Heights.


THE JALEPEÑO: How did Etsy start?

MATT STINCHCOMB: I was living with Rob Kalin (Etsy founder). He was a self-taught carpenter, photographer, painter. I was in a band, touring the country and Europe.

I started making t-shirts for my band, printing them in the bathroom. Rob said I should start a business.

He went to our landlord and convinced him to give us money to buy a screen printing press and we went into business.

Rob was interested in tinkering. While I was making t-shirts, he moved on to his next interest: handmade wooden computers.

He sold three to a local shop. Then he decided to sell online.

THE J: Did he design websites?

MS: He basically fell into web design.

He didn’t have enough money to pay rent.

The landlord owned a restaurant. Rob saw a proposal on the landlord’s desk that was twice as much as he owed. So he said: “I’ll make your website for half that.”

It didn’t bother him he didn’t know how. He got an HTML book and made it.

He wanted flames on the site because it was for a Cajun restaurant. He didn’t know how to do this, so he posted on a bulletin board at NYU and met two programmers.

These three were the founders of Etsy.

Rob saw all these people making things, with no place to sell them. So he decided to make a site for everyone.

THE J: Out of necessity. Solving his problem.

MS: Right. It was something he needed, something everyone needed.

THE J: Etsy breaks down walls for creative people, allowing them to reach customers easily.

MS: It’s really that simple. And Rob wanted it to be more beautiful and less expensive than eBay. He said: “This is my work, I want to represent it well, I care about what I’m selling.”

THE J: Is there a filtering process for quality?

MS: Not for aesthetic quality, that’s very subjective. We do make sure things that aren’t compliant with our policies don’t get on our site.

There’s also the ability for anyone in the community to flag an item that doesn’t comply.

We’re not saying “Sorry, your sweater is shitty, it can’t be on our site.”

THE J: How is Etsy different from other e-Commerce sites?

MS: Etsy is like the indie shopping mall. You (the seller) benefit from people coming to your own site, but also from the millions of people coming to Etsy every day.

You’re in a much bigger pool. You have people looking for handmade things who may not have gone to your personal site.




THE J: What is Etsy’s philosophy?

MS: Our mission is to reimagine commerce in a way to build a lasting and fulfilling world.

To use business as a tool to build a world that’s more durable from an economic, social, and ecological point of view, but also more joyful, more fun, more connected.

Our goal is to empower a big number of small businesses to build a human-scale economy.

I want to empower people to be successful and build businesses that have positive impact on their lives and communities.

THE J: What have you observed about sellers on Etsy?

MS: Many see this as their enterprise. This is their art, they love it. They tend to be very passionate.

They dream of making it (their business) successful enough to have the flexibility to make their art and be able to spend more time with their families.

THE J: And this couldn’t exist if not for the accessibility of technology. There are so many opportunities to learn and develop businesses with larger reach.

MS: A lot of the reasons why Etsy has worked – it’s not because we’re brilliant. There was the convergence of all these things happening at the right time.

The internet allowed for a marketplace to form. Maybe in the past there wouldn’t have been a market for this cup (holds up his cup). But now you can find people who really want it.

THE J: The alternative might be a flea market.

MS: Yea. And people are feeling disconnected from objects in their lives. In school they cut out Home Ec and Wood Shop.

We long for the tactile.

People want to engage with things more deeply, to make things. You also have the knowledge dissemination through different channels. I didn’t know how to screen print, but I looked up videos online and learned.

Farmers’ markets have increased a thousand times in the last 10 years. People want to know where their products come from.

THE J: We’re attracted to the idea of knowing the origins of things, who created them and how.

MS: And there’s accountability with that. There was a time when you had a relationship with people who provided the goods in your life. You didn’t make them a shitty cup because then they weren’t gonna buy it from you again. For that same reason, they wouldn’t make you shitty boots. You wanted to support each other.

There was a trust. I think that’s our natural state – one of connection, relationship.

THE J: A draw to the strength of real connection.

MS: And there’s the frustration when you have some electronic disposable thing that breaks. Who do you call? Who made that? You can’t figure that out.

You’re so disconnected to what has gone into that. That separation is what’s causing problems.

We need to be having a deeper relationship with the things and people in our lives.




THE J: We’re adapting to hyper-connectivity technology. I think we’ll take the good parts and shed the others. Use it to enhance human connection, not distance ourselves from each other.

MS: Yes. Another reason I’m excited by technology, Jeremy Rifkin writes in The Empathetic Civilization about how, long ago, we had the bond of the family, bond of the tribe, bond of the town, bond of your state.

We need to get to the bond with the biosphere – the bond between all living things.

It’s going to be technology that connects us globally.

THE J: Any specific ideas?

MS: Technology where I can speak German into my phone and you’re hearing English. That’s powerful because it’s a threat to old brittle institutions that have stayed in power for a long time. All of the sudden you can have every young Israeli person talking to every young Palestinian: “We don’t have to fight about this anymore.”

THE J: Huge opportunities to improve education.

MS: Education is about to be severely disrupted. That’s positive and negative.

Negative in the sense that, OK, a four-year undergrad is not accessible to most of the world. At the same time you build relationships and this stuff is really important. That’s the beauty of it.

THE J: And tough to quantify.

MS: Right. Online, everyone has access to knowledge. That’s incredibly transformative. You make it free. But you also need to create opportunities for personal relationships.

In college, you’re not learning the most in your classes, you’re learning in conversations on the quad.

THE J: Building emotional and social intelligence, human qualities.

MS: Yeah. I’m working on an educational startup right now. I’m trying to find the right marriage of those two things (free online education and personal relationships.)

You have content available online that supplements in-person cohorts, then you supplement online with place-based interaction.

THE J: Can you talk more about that?

MS: We’ve started a new entity called, an education non-profit focused on regenerative entrepreneurship.

You’ve got degenerative business on one end. These industries are extractive.

Now we have people thinking of how to be less bad. For a lot of businesses, less bad is good enough. Less bad is not good enough.

There’s another group further down that says: “Let’s be sustainable.” Sustainable is better than degenerating further, for sure.

What I want to focus on is: How do we make it better?

THE J: How do we?

MS: Business is a very powerful tool for organizing communities, connecting people. It can be utilized for good or bad.

If you have enough wisdom and skill, you can use business to create far more value for communities and the planet than it takes from it.

It makes things better than they were. That’s how I think of regenerative entrepreneurship.

THE J: The idea that business is the best way to improve lives, if done with compassion and integrity. John Mackay discusses this in Conscious Capitalism. 

MS: Exactly. How do we rethink how business is practiced, to raise everybody up?

If you want to reimagine business, you need to reimagine business education – how we think about it, what we’re teaching, how we’re teaching it, to whom we’re teaching it.

A big part is reaching more women, more minorities, giving underrepresented populations access to training.

Also, how to bring wisdom to students, not just knowledge.

THE J: The curriculum?

MS: Wisdom comes with a lot of unconventional practices and studies, different from a traditional business education.

I want to put people in the woods, teach people how to listen, talk about death.

I want to talk about what it means to be your authentic self. I want to teach contemplative practice. As well as basic business skills.

Arne Naess talks about deep ecology, the idea that we’re part of the environment, part of this whole ecosystem that’s all connected, interdependent. Your success is tied to the success of that ecosystem.

Without ecology, you don’t have economy. Without nature, there’s no stuff, there’s no shipping of things.

THE J: A focus on long-term perspective and redefining success around that.

MS: If you’re out there to exploit your customer, you’re not successful. If we don’t address climate change and wealth inequality, we won’t have customers.

How do we use that view, understanding you’re part of the ecosystem and you’re an ecosystem yourself?

You need to cultivate mind, body, and spirit to have the right framework to wield the tool of business to create more value.

THE J: Looking at the importance of quality, compassion, empathy. We’re all in the same boat.

MS: Right. Durability, relationships. Competitors aren’t really competitors.

That’s what I want to do, develop this curriculum with people thinking this way. And find the right way to employ that curriculum in the world.

We’re going to start by developing a fellowship program.

A regenerator.

THE J: How will it work?

MS: There will be local entrepreneurial fellowships for people who have ideas to regenerate a community where they’re based.

We’ll pair them with a mentor who has done something like what they’re doing.

We’ll put them through a three-month curriculum to hone their intuition, to bring more wisdom to their thinking.

We’ll support them for two years, put them in front of investors, do everything we can to make them successful.

If a local business opens and hires three people, that’s a win. We want to make a million of those little businesses. A big number of small things.

That’s what Etsy is – one business comprised of 1.5 million small businesses.

THE J: Where will you look?

MS: The business community, maybe also to the activist communities.

Occupy Wall Street? Awesome. You’re against the 1%. Why don’t we teach you to be entrepreneurs so you can harness that energy and passion to be really effective for your community?

We’re changing who is practicing business.


THE J: Would you have liked something like this when starting Etsy?

MS: Yes. I was in a band. I didn’t know anything about marketing.

Once we’ve honed the curriculum and regenerator model, we’re going to open-source it all.

We’re going to make online classes and teach any community how to start their own social enterprise and incubator program.

The J: Entrepreneur or not, anyone may benefit from these lessons.

MS: Our plan is to make the services available to the public for free. It’s gonna be fun.

Buckminster fuller said: “You don’t create change by fighting the existing reality, to create change you create a new system that renders the old system obsolete.”

Do we want to change companies? Or do we want to focus on the people who are going to be building the companies?

THE J: It seems entrepreneurial thinking isn’t being taught early enough, if at all.

MS: I think we need to be teaching it in 8th grade.

We’re still teaching people to work for a giant insurance company where you’ll have your career and you’ll rise up through the ranks.

THE J: What if we encouraged the smartest, most driven minds to think more creatively and entrepreneurially?

MS: Right. It’s a shift in mentality. Measuring success in ways that aren’t purely financial. Measuring success as impact, relationships, happiness, time spent with family.




THE J: Going public – what’s that like?

MS: I hope it doesn’t change things too much in terms of how we operate. We’re not going to optimize for quarterly returns.

We have a 100-year vision for the company, so we’ll do things that are more expensive if they’re better for the planet.

We’re saying don’t invest in us if you don’t like that.

That’s the biggest danger companies have, is always optimizing for short-term gain.

Going public is also like a tool. A fundraising tool.

It’s what you decide to do with that money and how you decide to run the company that matters. If your values are firmly in place, it’s good. There are a lot of great public companies.

The J: Did you reach out to executives about IPO strategy?

MS: Yeah. Ben Cohen of Ben & Jerry’s has become a friend. He said going public is the best but getting acquired is the worst. Going public is just a chance for your customers to own your stock.

I’ve heard from other people that an IPO is like a wedding, but you need to focus on the marriage.

THE J: Starting a business, shifting mentality can be tricky. There can be a tendency to recoil, because there’s a fear in uncertainty. What’s your personal strategy?

There’s a concept in Buddhism called Shoshin – Beginner’s Mind. I think my mind isn’t so filled with what will work and what won’t.

I’m open. I can do that. I’ll try. When you listen to others who say: “You can’t do that,” that’s where fear comes in.

I think it’s good to be naïve and be scrappy and figure it out.

THE J: And not to be discouraged by the things in your way. To work with them. It takes commitment to a vision to make it happen.

MS: I agree. Everyone’s worried about making the next big thing.

I feel like we can say: “No, let’s make the next 100 small things.” I think people are unwilling to do this because they think the impact won’t be big enough.

But, if three new people have a job, for the first time they have their own apartment, that’s big.

People want everything to be fast and big and immediate.

I want to do this right, and I want to do it deeply.

THE J: And that’s the mentality needed to develop something that’ll last.

MS: Yes. You can’t hold so tightly to things. You have to be able to admit when you’re wrong and not look at it as a failure because your idea failed. Move on.

When something goes wrong, look at all the circumstances of the situation, then build in safeguards to prevent them from happening in the future.