Imposter Syndrome & My Conversation with a Multi-Millionaire

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.


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.





If you’re interested in reading more about Summit at Sea, CNBC and Business Insider covered the event and wrote about it here and here.

10 Companies Prepare for Launch: A Factory45 Update

It’s strange to say, but when Factory45 started in June I couldn’t envision getting to early October. It seemed so far away, to be two-thirds of the way through the program, and I had no idea what to expect from the months leading up to it. The worst-case-scenario questions going through my mind were silenced just enough to not paralyze me into inaction, but they were there all the same:

“What if all 10 companies drop out before the program is done?”

“What if I realize it was a terrible idea?”

“What if this doesn’t work?”

With both Modules 1 and 2 now complete, I can (gratefully) say the past four months have exceeded all expectations. Four months in, all 10 companies are still pushing through and making measurable progress with their products.

Looking at some of the numbers: 8 out of 10 are currently in the pattern-and-sample-making phase, 7 out of 10 have finalized their fabric sourcing, and 9 out of 10 have or are close to having finished websites.

Isamplemaking-2n their own words (from the mid-program feedback survey I sent out):

“I have made more progress since I started F45, than I have in 2 years trying to do this on my own.”

“I’ve accomplished so much more than I would have on my own and feel very accountable to the program, which has caused me to pull the trigger on decisions that I would have otherwise dilly dallied on. The biggest benefit for me is the weekly structure; it keeps me super focused and organized. Although I do often feel overwhelmed working on all of the different aspects of my business simultaneously, F45 has made the process so much clearer and more manageable.”

“I remain so impressed. Your organization and presentation are that of someone who has been doing this for years. I have loved this and am a bit afraid of it ending.”

That’s not to say everything has been rainbows and butterflies or that I wouldn’t change anything. The group has collectively had to overcome a lot of “imposter syndrome,” fear, and self doubt. For many of them, it has taken time to trust themselves and to navigate their way through the high’s and low’s of the entrepreneurial rollercoaster.

There have been tears on 1-on-1 calls, “freak out moments” via email, and high-pressure moments of angst. Very little is happening on the timeline I had planned for, which has simply meant I’ve had to adapt and adjust my expectations of how things “should” be progressing.

samplemakingWhen I think back on the past four months, though, I am incredibly proud of what has been accomplished. It’s those moments that are celebrated together, whether it’s on a Wednesday night group call or when I get a text at 8:30 on a Friday night asking for a “quick chat,” that I hold in my memory with immense gratitude. To have a small part in creating 10 new businesses, that could effectively make real, marked change, is not something I’ve taken for granted.

As we enter into Module 3 next week, I’ll prepare my Factory45’ers for launch and for the next phase of their journey without me. To have an accelerated start, the support of peer mentorship and the tools and resources to keep forging ahead is something that I wish everyone could have when they’re first starting out.

The challenge in the next two months will be preparing everyone to leave the proverbial “nest” that has become as much a routine as it has a safe haven. The challenge will be in ensuring 10 new entrepreneurs that they have what it takes to finish what most people only dream of starting.

Photo credit: Jesse Syswerda and Angela Tsai