Ambiguity is an Entrepreneur’s Worst Enemy

Photo cred: luv life

Photo cred: luv life

Whenever you see a successful business, someone once made a courageous decision.” – Peter Drucker

I despise ambiguity.

Every time it shows its stinking, snarling face, I have to use all my strength to face it head on and avoid curling up into a ball in the corner.  Luckily, since starting Feast I’ve been able to count a great deal on my cofounder which makes life a lot easier.

It’s easy to make decisions based on morality or when there’s a clear choice.  It’s when there isn’t a clear choice that the darkness creeps in and you stop dead in your tracks.

Ambiguity will paralyze you. You can’t make a logical decision about something that doesn’t have a clear right answer, right?

“Nothing is more difficult, and therefore more precious, than to be able to decide. ” –Napoleon Bonaparte

Not making a decision is infinitely worse than making the wrong decision.

The alternative to making no decision is just guessing.  It’s taking a shot in the dark. But if you’re like me, guessing isn’t something you’re really wired to do.  I like making decisions based on gut feelings or data, and that’s it.

The worst news is that ambiguity is inevitable for an entrepreneur.  You will run into crossroads with no signs.  I promise.

The ability to make decisions during these times of ambiguity is vital.  If you don’t, you die.  It’s probably the most important learning I’ve had in my career as an entrepreneur.

“Once you make a decision, the universe conspires to make it happen.” –Ralph Waldo Emerson

It’s Not About Fear

If you’re an entrepreneur, you’ve already overcome huge battles with fear.

You probably have no problem trying crazy new things and you might even embrace failure.  But ambiguity presents a different battle.  Your lack of movement isn’t a result of fear.  It’s a result of choice.

Sometimes you just have to make the choice to close your eyes and swing.

Don’t strike out looking.  You have to keep moving, whether right or the wrong, YOU HAVE TO KEEP MOVING.  

There’s no such thing as the wrong direction.

The only way to figure out the right answer is to act.  If you’re right, then great keep doing that.  If you’re wrong, now you know that and you can adapt.

“It doesn’t matter which side of the fence you get off on sometimes. What matters most is getting off. You cannot make progress without making decisions.” -Jim Rohn


It’s taken me a long time to be able to face ambiguity in my career.  It’s something I battle with every single day.

A few tips I’ve picked up for battling ambiguity:

1. Ask others.

Asking other people can help, sometimes.  They may be able to provide a perspective that you hadn’t thought.

Ask your cofounders.  Ask your team.  Ask your mentors.  Sometimes the answer can reveal itself by talking to random people with fresh perspectives.

2. Look to examples of success.

Can’t figure an answer out for yourself?  Look at what others have done before you.  There’s a reason they chose that route.  It might just work for you too.

3. Get into the habit of testing.

If you’re planning to test everything you do, then it becomes less of an issue which way you choose because you know you’ll find the answer out quickly.

Even if you think you’re making the right decision, always test.  Compare.  Challenge your assumptions.  You can only learn from your mistakes if you’re able to identify them as mistakes.

I think part of the reason we avoid making decisions is because we’re afraid that it will take a long time to learn whether we were right or wrong.  Which gets to the next point…

4. Realize that nothing is permanent.

At Feast, we’ve changed our product and business model at least 6 times in 6 months.  We’re learning at such a rapid pace that individual decisions at this point aren’t actually that important.  What’s important is that we’re making them, and learning.

5. Acknowledge your ambiguity.

The scariest thing about ambiguity is it doesn’t feel tangible.  It’s this dark abyss. It’s a vague status quo that consumes you, causing you to procrastinate without really knowing why.  You might blame it on not being motivated.  But it’s not motivation that’s your problem.  It’s the discomfort of indecision that we naturally try to avoid.

Acknowledge your ambiguity when it happens.  Call it out and then beat it.

When you have to make a choice and you don’t make it, that itself is a choice. – William James

What have you done to overcome ambiguity?  Please share your experience, because it’s something I think we all face regularly.

Why I Left NYC for SF, and Stayed There



I have lived in NY my whole live and lived in NYC for almost 2 years.  I’ve lived in SF for 3 months.

Zaarly moved me out to SF.  When my work with Zaarly completed a couple months ago, I had the choice to go back to NYC.  But I stayed.

Naturally, in San Francisco I get asked the question a lot.  “Which city do you like better?”

My answer usually goes something like “They both have their upsides and downsides, their charms and their shortcomings.”

I wanted to talk a little bit about the biggest differences specifically for entrepreneurs.

Of course “it depends” will always be an apt answer to some extent, but overall, if you’re a first time entrepreneur, there’s nowhere else you should be.  Go to San Francisco.  Here’s why…

Serendipity is king.

Entrepreneurship is very much about serendipity.  Founders meeting each other, an idea coming out of thin air to disrupt an industry, meeting someone that changes your perspectives…  out of serendipity comes creativity and action.

Serendipity, or luck, isn’t something you can fully control, but it is something you can impact.  You have to work hard to be lucky.  You have to put yourself in the position for serendipity to occur. You have to be in the right place. Take my story as an example.

I’m an entrepreneur at heart.

I had the first opport and became a cofounder and partner.  After that, I joined Zaarly.  Zaarly moved me out to San Francisco.  When I parted ways with Zaarly, I knew that my next big move would be to start my own company from the ground up.

I have a list of ideas for companies, and some of them didn’t even suck.  But nothing was really compelling me to take action.  Nothing was keeping me up at night.  Over 2 months went by and still nothing.  I’ve been consulting to be able to work with different amazing companies and help them solve their community challenges.

I knew serendipity would have to hit soon.  In SF, every single day you meet a new entrepreneur.  You can’t throw a rock in SOMA without hitting a startup office.  You can’t go to a coffee shop, restaurant, bar, concert or grocery store without overhearing a conversation about raising money, building a company and changing the world.

I’ve been living in a sublet apartment since I moved here.  It was a 3 month sublet, I was planning on financing my own apartment after with the options at  I chose it because of the people more than anything.  I was brand new to the city and wanted to live with people that I could potentially become friends with.  It worked, and they quickly became my best friends in San Francisco.

One day, a few of us were at the apartment just working and relaxing on the couch when I threw out a random idea.  I like to cook, but I never know what to cook and I’m overwhelmed by grocery stores, so this would be a solution to help people cook different things, eat healthy and learn more about what they’re eating.  It was a simple idea, and we started to talk through it.  It only took a few minutes to realize that this idea was the one I’ve been looking for.  Turned out it’s the one my roommate, Nadia was looking for.  Now we’re building it together.

Could that happen in NYC?  Or any other city in the world?  Yes, it definitely can.  But if you want to improve the odds of serendipity occurring in the startup world, there’s no better place than SF.  I found this apartment on Craigslist and knew very little about any of the roommates when I signed the lease.  But in SF, you can feel confident that whoever you end up living with, there’s a good chance that they’re going to be involved in the tech/startup world to some extent.

But it’s not all perfect in SF.

Taking things with a grain of sincerity salt.

There’s a lot of aggressive positivity in San Francisco, in contrast to the common skepticism that you find in NYC.  In SF, everyone is so supportive of each other, almost to a fault.  It’s a great positive vibe, but it can be somewhat insincere.

It also results in a lot of talk without a lot of follow through.  Everyone LOVES to talk about the projects they’re planning to work on, but finding people who are actually taking action and executing can be tough to come by.  When you want to support everyone, and help everyone else with their projects, you end up not following through on a lot of it.  You commit to more than you’re capable of actually doing.

Accessibility may be the biggest differentiator. SF is as welcoming as it gets.

On the upside of that overt positivity is the generosity with time that you’ll find in SF.  In NYC, everyone is always in a rush and can be very protective of their time.  Someone that I reached out to recently in NYC responded to my request for a 15 minute chat, saying that due to other obligations, they couldn’t chat with me for 3 months.  And they’re not exactly a “big deal”.

In SF, you can meet with pretty much anyone, whether they’re a big deal investor or a successful entrepreneur.  Everyone’s down to hang out and grab a beer.  They don’t require an agenda and a list of questions.  They just want to be helpful and keep doors open to contribute back to the community.

That accessibility and dedication to contributing to the greater startup community is my favorite aspect about the SF startup scene.  I’ve been here for 3 months, and I feel very much a part of the community.  Even more so than in NYC.

I came to the NYC startup community as a young professional and had to build a network from scratch.  It can be like pulling teeth in NYC.  People and companies just don’t make themselves accessible.

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The SF bubble makes it hard to understand real customers.

Another important distinction that you need to make if you’re debating which city to build your company in is the consumer market.  SF isn’t real.  It is very much a bubble of conversation.  Establishing a product market fit in SF isn’t necessarily replicable in other cities.  That can be true for any city, but the gap is definitely more prominent in SF.

In NYC, you’re surrounded by every industry possible and every kind of person.  If you’re looking to create a replicable model, there’s a reason they say “if you can make it in NYC, you can make it anywhere”.  The consumer market in NYC will be much more true to form.

Then there’s the talent and funding question.

As far as finding talent goes, I think it’s just as hard in both cities.  There’s more talent in SF, but there’s also much more demand for that talent.  If anything SF has a slight edge because of the serendipity factor.

As far as funding goes, SF still has an edge but NYC is getting much better.  When it comes down to it, if you’re raising money from amazing investors, you want to be able to utilize the resources that they can provide you beyond just the money.  That means you want to be close to your investors.

There are more investors in SF and they’re a lot more accessible.

Cost of Living

Forget flowers in your hair. If you’re going to San Francisco, be sure to have some extra change to spare. Thanks to skyrocketing home prices, and an increasingly competitive rental market, that’s the new message for anyone who is thinking about moving to the City by the Bay. Just how expensive has San Fran gotten?

Well, according to the Council for Community and Economic Research, the total cost of living in San Francisco is 62.6% higher than the U.S. average—and housing is nearly three times more expensive than in other U.S. cities. Below, we’ll take an in-depth look at all the data on living expenses in San Francisco to find out who exactly can afford to live there.

San Francisco’s crazy high cost of living starts with its crazy hot housing market. Simply put, affordable housing is hard to come by in SF. According to data from the National Association of Realtors, existing home sales prices increased nearly 36% in just two years, from $543,780 in 2012 to $737,600 in 2014.

That $737,600 represents the second highest average sales price in the U.S., behind nearby San Jose. There is one upside to surging home prices, however. Homeowners in San Francisco have earned huge savings through refinancing in recent years.

If you are looking to see how your budget would fare in a different city, considering the cost of living is important. It’s a good idea to see how that would impact your budget and future financial goals.

In the end my heart is very much in NYC and what’s happening in the startup community there is truly amazing.  There IS a stronger community forming every day and there is a concerted effort to open doors, increasing accessibility.

Some of my favorite startups in the world are leading the way in NYC and creating a stronger startup ecosystem as a whole.

We’re going to start off building our company in SF.  It’s a hyperlocal concept that’s actually a great fit for SF.  Also, both cofounders are here, and in just 3 months, I’ve built up a much stronger network of potential partners and investors than I have in NYC.

I know serendipity will bring me back to NYC eventually, and I can’t wait for the day when I will build my startup there and contribute back to the community.

Right now, SF is where I have to be.