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Over the weekend, I boarded a ship in Miami with over 2,000 creatives, tech millionaires, celebrities and startup founders for a three-day, invite-only “conference / festival” called Summit at Sea.

In the company of Martha Stewart, John Legend, Harry Belafonte, Blake Mycoskie and the list goes on, I spent the weekend connecting with some of the leading social impact entrepreneurs in the world.

There were a lot of conversations and experiences that I took away from the weekend, but there was one in particular that I want to share today.

On our last night on board, I walked down to one of the bars on the ship by myself. (The great thing about this event was that you couldn’t go more than 30 seconds without someone saying hello and introducing themselves. For better or worse, you never felt alone.)

“I love your dress,” said a blonde-haired woman in her early forties, standing next to me at the bar.

I told her I bought it second-hand and we started chatting about thrift shopping before getting into other topics, ranging from Burning Man to the challenges that minority entrepreneurs face.

It wasn’t until 30 minutes into the conversation that she told me who she was:

A serial entrepreneur who has sold three companies for over 30 million dollars — each.

Upon realizing that I was having a one-on-one conversation with someone as successful as she was, I found myself starting to shrink.

Who was I to be taking up so much of her time?

What could I possibly say that would be interesting to her?

What was I doing here?

I mean, really, who invited me on this damn boat?

My doubts were creeping in, I was feeling like a fraud and I sensed that in any minute, she would excuse herself from the conversation.

“Do you ever get imposter syndrome?” I asked before I could stop myself.

“Oh my gosh, all of the time,” she said.

“Really? Does that feeling ever go away?”

“You know what, you fake it until you make it — and you never actually feel like you make it. I’ve sold three companies and have more money than I’ll ever need, but I still question the validity of my success.”

Instead of the conversation slipping away like I had imagined, we talked for another 30 minutes.

She opened up and told me what it was like to raise venture capital as a woman. We started talking about how we can collectively build each other up as female founders.

The conversation shifted to a place where I no longer felt inferior — I felt empowered. And it was because we were able to relate on a human level.

I realized over the weekend that this was the biggest takeaway.

As people on the “outside,” we can tend to build others up to be…

Larger than life.

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I imagined the founders of companies like Google, Warby Parker, Life is Good and TOM’s to have it all together.

Articulate public speakers. Impeccably dressed. Perfectly-trained socializers.

We see power, money and success and automatically put them on a pedestal that raises them above the rest.

And while, yes, their accomplishments are generally unparalleled, our weekend together humanized everyone around me.

(Except for maybe Martha Stewart.)

The founder of Zappos was humble (and hungover) on stage. The founder of Uber was soft spoken and unassuming. Even John Legend was modest and quiet.

Maybe they weren’t all experiencing imposter syndrome, but I don’t think anyone would deny the experience of feeling uncertainty and unworthiness.

It doesn’t matter how much success you’ve seen, how much money you have, or how great your life appears to be on the outside.

We’re all just a bunch of humans doing the best we can.

Having come off of the mental and emotional high of this weekend, I’m challenging myself to appreciate where I am right now while truly believing that what I’ve done is enough.

Regardless of whether you have started your company, are currently in business or are still waiting for the right time to start, I’d encourage you to join me in this.

You are worthy. You have done enough. And you are exactly where you need to be.

When you start to doubt yourself remember that so much of the success of others was based on one overarching fact:

They didn’t stop moving forward — even when they doubted themselves. Or felt like frauds.

They kept putting one foot in front of the other.

Whether it felt like the foot of an imposter or not.

 

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sustainable fashion advice

Every few months, I’ll get hit with a lack of marketing “mojo.”

Usually, marketing is my top priority. (It should be yours, too, if you’re running a business.) I know the marketing channels that are most effective for me and I’m typically very strict with my output.

But then, all of the sudden, I’ll wake up one morning and it’s like some sort of whimsy, lazy fairy flew into my life to take all of the motivation away.

Especially when the Factory45 program is in session, I’ll start investing more time in helping other people start their businesses and let my own business fall to the wayside. Which is all good and dandy until I’m hit with a major dose of business FOMO.

“Man, I really wish I had made that list.”

“Wow, she got that feature? I wish I had pitched that.”

“I should totally capitalize on that topic and write about it… maybe tomorrow…”

I find myself justifying my lack of motivation with thoughts like: everyone needs a break sometimes… or… I’ll do it after the holiday weekend… or (my favorite one)… it’s summer / holiday season / school vacation, no one is paying attention anyway.

While I’m all about dishing advice and sharing lessons learned, it should go without saying that my entrepreneurial journey is a work in progress just like anyone else’s.

Even writing about not having motivation makes me want to stop writing this post. The struggle is real.

The silver lining, though, is that I’m able to look at this phase as just another state of entrepreneurship — my guess is that even Richard Branson takes a hiatus on his private islands once in a while.

When you don’t have two-weeks designated vacation time or a job that ends at 5pm, it can be easy to forget that very few people push full-steam ahead 100 percent of the time.

And while this is certainly not my first time in entrepreneurial La-La land, it’s the first time I haven’t tried so hard to fight it. I’ve been conscious of not attaching negativity to it even if I would have felt immense guilt in the past.

In doing so, I’ve been able to look at this lack of motivation in a way that will make it easier to manage next time.

In case you ever find yourself in a similar boat, here’s what I’ve observed:

1.) Embrace it. I was traveling for two weeks and by the time I got back to Boston last week, I had caught some sort of illness and completely lost my voice. By Wednesday, my typical writing day, the last thing I wanted to do was write a blog post.

It’s kind of embarrassing how much I struggled with the idea of taking a week off from the blog. What if someone notices they didn’t get an email from me? What will I post on social media during that time slot? What if people unsubscribe?

Eventually, I was able to get rational about the fact that zero people will care if they don’t hear from me. That simple realization allowed me to embrace a free afternoon of laying on the couch with a box of tissues, a cup of tea and a steady line up of Netflix.

It was so much more productive when I chose to embrace the “lack of productivity” rather than waste energy on fighting it.

2.) Give your attention to your behind-the-scenes operations. Lacking the creativity for another Instagram post or quippy tweet? Use the other side of your brain and focus on the aspects that may be pivotal to your business but probably aren’t seen by your customers or audience.

For me, that means giving extra time and attention to my Factory45’ers: jumping on impromptu phone calls when they need it, fully engaging in our private Facebook group, problem solving during office hours, and giving them the best client experience possible.

It may not be direct marketing ammunition, but more important than the perfect Instagram photo is the user experience you’re giving your customers.

3.) This too shall pass. There is nothing constant about running a business. It’s always changing and evolving and depending on the season, your launch schedule, your production timeline and other factors, your marketing mojo will eventually come back to you.

Don’t let your current state convince you that it’s here to stay.

4.) Accept it. There is always going to be a colleague, another designer or a company you look up to, appearing to be multiple steps ahead of you. That’s life — running a business is no different.

The truth is, you’re not missing out. Your experience is unique to you and you’re exactly where you should be. There is always going to be another opportunity, there is enough time, and your journey should be dictated by you — not by an outside perception of someone else.

Do you and good things will happen. 

 

 


Sustainable Fashion Advice

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Whenever anyone asks me:

What’s your one piece of advice for new designers?

I always have the same answer. I’ve worked with hundreds of entrepreneurs over the years, and I warn all of them of the same mistakes that I made when I was first starting out in the fashion industry.

Let me take you back to the summer of 2012. I’m living out of a 1993 Chevy Conversion van on a three-month “sustainable fashion tour” of the Pacific Northwest.

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Six months prior, my co-founder and I had launched the highest-funded fashion project in Kickstarter history to fund the production of our first piece, the Versalette by {r}evolution apparel. We were on a mission to shake up the fashion industry, to prove that less is more, and to show everyone that conscious consumerism can change the world.

By working with a sew shop in the U.S., sourcing 100% recycled, U.S.-made fabric, and considering every tiny part of our supply chain, we had attracted the attention of 1,400 first customers, in addition to media outlets such as The New York Times.

But that’s not where we started.

My journey into fashion production began a year and a half earlier when my co-founder and I first came up with the idea to start a “sustainable clothing company.” We had no idea what that really meant, so we blindly began contacting any person we thought had the slightest chance of helping us.

We called organic cotton farmers in Texas, environmental studies professors in Missouri, eco-fashion models in Brooklyn, Merino wool suppliers in New Zealand and the list goes on…

Looking back at the emails I sent to suppliers, I know now that my inquiries surely got a swift click of the delete button. I didn’t know how to talk to industry veterans, I had no idea how to talk “the talk,” and it showed.

Eventually though, after a year and a half of trying, we found fabric and materials that fit our sustainability guidelines, a sew shop who would work with a fledgling startup, and that’s when we successfully funded our Kickstarter campaign.

If we thought sourcing was difficult, we couldn’t have imagined what the production process had in store for us.

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First hurdle, the organic cotton drawstrings we needed were on backorder and the sew shop couldn’t move forward until they had all materials in-house. We got bumped off their production calendar and couldn’t get back on until the drawstrings arrived.

By the time we began production, we were running four months late.

The backordered drawstrings, production delays and an additional shipping fiasco were rookie mistakes we had to live with and learn from.

But the next mistake we made was the biggest one of all — and it’s the only thing from this story that you really need to remember:

We weren’t at the sew shop when production started.

Sure, we signed off on samples and patterns, but the worst decision we made was not being with our production team when Versalettes started coming off the line.

We weren’t there to offer additional quality control, answer questions in person, build relationships with our sewers and get them invested in our project.

And it came back to bite us.

Our first shipment of Versalettes arrived and a third of them had crooked pockets, misplaced button holes, lost drawstrings or unfinished seams. We got a second shipment and it had the same problem. The sew shop was sending us batches of 40 units at a time and instead of being thrilled to open them, I was terrified.

At the time, it would have been easy to blame the sewers for being “unskilled,” but that simply wasn’t the truth.

Being completely new to the industry, we didn’t know how crucially important it was to a build relationships with our sew shop and be there at the beginning of production.

We had no one to blame but ourselves.

When you’re first starting out, trying to do design and marketing and media outreach and customer service and blogging and everything else yourself, it can be easy to take production for granted and assume someone else is handling it.

The thing is, no one is ever going to care about your product as much as you do.

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After we received our second batch of Versalettes, I flew to North Carolina to visit our sew shop and work out the “kinks.” I spoke to each sewer individually, shared the article about us from The New York Times, and showed them photos of our models wearing the Versalette.

Spending a few days with our team, I finally understood that relationship building in the manufacturing industry is no different than in any other industry.

Shortly after I flew back to the west coast, our third shipment arrived.

Not a mistake in the bunch.

 

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This originally appeared as a guest post on Startup FASHION here.


A few years ago, I went to Bali and wrote two versions of a book.

I know, how obnoxiously “Eat, Pray, Love” of me.

My former co-founder and I had decided to close our doors at {r}evolution apparel (after completely burning out our relationship) and it was an impulse purchase I made with my portion of our leftover funds.

I left Boulder, CO, moved in with my parents in Boston, and a month later hopped a flight halfway around the world.

After the success of our Kickstarter campaign, people were constantly saying, “You guys need to write a book.”

“Write about your journey,” they said.

“Write about the success of your Kickstarter.”

“Write about the changes needed in the fashion industry.” The suggestions were endless.

So, with the mixed emotions of heartbreak and relief that happen when you walk away from a business that seems to have such a bright future, I went to Bali to write the book that everyone said we should write.

I booked a private room for $500/month on Airbnb and found myself two miles from the nearest town surrounded by rice paddies and oxen.

For 30 days I followed the same rigid schedule. Wake up with the sun, follow the dirt road into town for yoga, eat lunch at a local cafe, walk 30 minutes home, stop for a fresh coconut, sit out on my front porch — write 2,000 words.

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I reasoned that if I could average 2,000 words a day, then I would have 60,000 words by the time I left. And you only need 60,000 words for a full-length book.

The process was both grueling and therapeutic as I sifted through three years of memories.

Why we decided to start a clothing company.

How we got interested in sustainability.

An account of our first fight.

What we learned from botching our first prototype.

What it’s like to spend two months driving a conversion van around the country.

By day 15, I was ready to delete the whole file. Just burn it. Not a trace of evidence.

Instead, I opened a new document and started over.

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By the time I flew back to the States, I had written two 30,000 word drafts with no intention of either seeing the light of day.

Three years later, they’re still sitting on my old, mostly-broken laptop — without a backup file.

Now I’m not going to tie this all back into the importance of creating a routine to reach goals. Or a lesson on how goals change. Or how everything happens for a reason. I’m not a personal development coach.

But I do have something to say about the “journey.”

I’m as guilty as the next person when it comes to expectations and outcomes. Most of us start businesses with the intention of making a living off of it.

Yes, passion and joy can be the driving motivators in getting started, but the desired outcome is to be able to support yourself off of that passion and joy.

The danger — the thing to look out for — is when you realize you’re only focused on the outcome.

Because that’s when you miss the journey.

About a year into starting {r}evolution apparel, I remember writing a post for our first blog – it was a letter to myself, and I’ll never forget the last sentence:

“You’re not going to be a 25-year-old bartender trying to start a clothing company forever.”

That sentence has been embedded in my brain for the past five years and as time passes, I find myself adjusting the words to fit my current age and situation.

You’re not going to be here, right now, doing this… forever.

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It may seem painfully obvious, but I think it’s something that a lot of us entrepreneurs tend to forget.

Starting a business is one of the most challenging endeavours a person can take on — it’s a complete mind game, a lonely road, and can be uncomfortably risky. Are you going to enjoy every single moment of it? No.

But if you aren’t stopping every so often to appreciate what you’ve built, what you’ve created and what you’re going through — that 99% of the world never will — then what’s it all for?

When I look back at the month of my life spent writing a book, I can easily see it as time and money wasted.

Did I have big plans to pitch to publishers? Yes.

Did I have more realistic plans to self publish and sell it on Amazon? For sure.

Instead, I showed myself that I was capable of committing to a routine, to seeing a project through and being okay with a different outcome.

Entrepreneurs have to be courageous, committed and adaptable. But more than anything, they need to be able to see a vision for the future —

with an even greater appreciation for the present.


Sustainable Fashion Advice

A while back, I wrote a post about entrepreneurship and the real downfall of failure.

I argued that it isn’t the act of failing itself that’s the most terrifying, it’s the external connections we make to it.

If we fail, we’ll lose our dignity.

If we fail, we’ll lose our life savings.

If we fail, we’ll lose our home.

While these are extreme examples, I know our thinking can often go to “worst-case-scenario.”

I remember a conversation was brought up by one of the entrepreneurs in this year’s Factory45 program. She wrote:

I’m looking for advice: Having just finished my master’s degree, it may come as a surprise to some family and friends who don’t know about my project yet that I’m going the entrepreneurship route. Anyone have tips on how to introduce a significant career change to family, friends, and/or even an employer (I plan to keep my full-time job for a while)?

This got me thinking about the “pre-failure phase.”

Before the fear of failure is even an option, first there is the fear of getting started.

It’s the fear of taking the plunge. Of not knowing what’s going to happen. Of worrying what your family and friends are going to think.

The greatest inhibitor to becoming an entrepreneur or pursuing a great idea or moving forward with your true life’s work is — never getting started in the first place.

When we make it public and declare our idea to the world, we simultaneously have to face the feeling of being seen.

Being seen means you open yourself to critics, you open yourself to the doubters, and you open yourself to vulnerability in a way you probably haven’t before.

Throw in the visibility of the modern-day Internet to the mix and the stakes get a whole lot higher.

I’m no stranger to critics. While the supporters in my life far outweigh the cynics, it doesn’t make the occasional negativity sting any less.

I’ve been called an asshole, a “self-aggrandizing bitch,” a piece of shit and other equally flattering names (I don’t read the comments section of The Huffington Post anymore).

I’ve had outsiders call Factory45 just another “expensive online course” (I won’t even dignify that with a rebuttal).

And year after year, I’ve faced family and friends at Christmas parties, dinner parties and happy hours, wondering when I’m going to get a “real job.”

Over the past five years as an entrepreneur, I’ve had practice dealing with the “gremlins” (yep, you cross me, I dub you a gremlin).

While an off-putting email or comment can still throw off my day at times, I can tell you it does get easier.

If you’re one of those people, who is tinkering with a great idea, a new business or an alternative career path, remember this:

The critics, the doubters, the cynics only have power if you give them the power.

As hard as it may be, you can consciously accept that there will always be some degree of negativity coming at you, but you can also consciously choose how you react to it.

Power is energy. And you get to decide where to put that energy. It can either be your demise or… your strength.

Like I said, I loved some of the other responses from this year’s Factory45 crew, so I want to close by sharing a few pieces of their advice in opening yourself up to getting started:

  • Stay close to those who support your dreams and let you blab on and on, even though they don’t understand what you’re talking about.
  • Speak from a place of vulnerability. Don’t predict the reaction you’re going to get, because it will come out in your tone.
  • At the end of the day, our opinion is the only one that matters. It really is. At the end of the day, you are responsible for your life.
  • I feel that when I do get the occasional negative reaction, it’s usually from people that have never tried to make their own dreams a reality.
  • Walk into the conversation with the knowledge that approval is not the goal – information is. You want those around you to be part of the vision, to be in inquiry with you… and I would recommend making it a two-way and engaging conversation.
  • “The only way to do great work is to love what you do. If you haven’t found it yet, keep looking, don’t settle. As with all matters of the heart, you’ll know when you find it.” – Steve Jobs

If you’ve been a Factory45 reader for a while you know I’m a big fan of Dr. Brene Brown, who is a researcher on vulnerability and shame.

You may know her from her two viral TED talks. She did another talk that’s not as well known called, “Why Your Critics Aren’t the Ones Who Count.” It’s a must watch — even if you’re the most confident guy/gal on the planet.

 

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