How we leveled up the Cookie Off and ended up raising over $175,000…

Written by Sol Orwell

The last ever Cookie Off is done (check out the pics). The #cookielife is now finished.

When I first started planning the Cookie Off, I was in a bit of a bind – we had almost 40 competitors last year – so how was I going to top it?

What I did was slightly downgrade the Cookie Off (we had only 28 different cookies), but then add a “Sol’s Feast of Fantastic Foods with his Favorite Friends,” featuring 40 of my fav foods (from my favorite types of bread to my favorite burger to my favorite sandwiches, and, of course, my favorite desserts).

So during the afternoon we had the Cookie Off, then a few hours break (so that people could digest all the cookies), and then the feast for the evening at another venue.

Instead of trying to level up the Cookie Off, we pared it down a bit, and then added a complementary event.


The problems with most events.

As I looked through the feedback from the last Chocolate Chip Cookie Off, I started to investigate more about what drives someone to an event, and what most events fail to do well.

There were three major issues that most events have:

1. Overly scheduled.

Ostensibly whenever someone discusses the ‘value’ of an event, it’s about the “people I met there.”

However, most events treat the meeting-of-others as an afterthought.

You usually have a bunch of scheduled speakers – say, 10-10:50, 11-11:50, and so forth. Then you have a cocktail hour, and then some after-party (usually at an overly loud venue where you can barely hear anyone unless you shove your ear next to their mouth).

And with such little time, you can see people’s eyes darting around, thinking “so many people, such little time!” thus making it hard to have deep conversations.

If the best part is the people I meet… why the hell is it so hard to do that?

2. Meh curation.

Most events have a singular purpose – sell out. That usually involves them 1) having a headline speaker that gets people to buy because they are fans and 2) open up tickets to the public.

What happens is you get a hodgepodge of people attending with very disparate interests and effort.

The worst, to me, are people who have no desire to engage in a conversation. Ugh.

3. Meh venues and even more-meh food.

Most events are in boring venues – a convention center, a conference hall in a hotel, etc. It may be slick, but it’s pretty drab.

Furthermore, the food is usually a catered buffet. Catered food can be good, but it won’t be memorable; you’ll never eat anything that makes you go “woah.”

I took the time to get feedback from attendees to understand what their underlying problem(s) were.


My fixes to the three fundamental issues with most events

So if we’ve identified the three main problems to solve, how do we level up the overall experience?

1. Cookie Off + Networking, and that’s it.

The Cookie Off itself ran from 2-5pm. This was when you ate too many cookies, hung out with friends you hadn’t seen in a while, and revel in the absurdity of the event.

We then took a break from 5-7pm. Recharge. Take a nap. Digest the food. And get ready.

From 7pm until 1am, it was time to chat. To get into in-depth conversations with people. To learn from others, and help them at the same time. All at a different venue (changing venues can change the vibe)

Whatever issues you have, personal or professional, someone else will have gone through it, and most importantly, will be willing to help.

The Cookie Off was never about some famous speaker. It was about meeting the people there – that was the entire focus.

2. Curated.

At my last two charity food offs, I made everyone fill out intake forms, and then when you showed up, you were given a list of 3-6 different people you had to meet.

The crowd I hang out with… the people I respect… they are good at what they do, and they’re willing to share and help.

I personally invited everyone who attended. The Cookie Off isn’t for the public – it’s for the people I know and like.

And those kinds of people are the type who know their shit, don’t think they’re the shit, and are willing to help you with your shit.

We didn’t get together because it wasa gathering of eFamous people. This wasn’t for the kind of people who record nine instastories a day and are all the about the selfies.

There was no public sales page. Everyone who bought a ticket did so because I messaged them on FB or sent them a quick email.

People who know their shit. And more importantly, are friendly and happy to share.

3. Dope venues and my favorite foods.

The Cookie Off was held at Love Child Social, a co-working space that becomes a nightclub at night. It was a place that had one long space for all the cookies.

The feast afterwards was help at the BATA Shoe Museum. We took over the entire space and had two main floors (and an outside area). There were corners and nooks and crannies for people to bunch up in small groups and have private and intimate conversations.

Furthermore, there was a plethora of food, with different foods on different levels. This kept people flowing, giving them more opportunities to run into different people. Instead of a single caterer making different foods, we had 41 of my favorite food items served at the feast.

I attempted to solve the problems people had with other events.


Supporting multiple charities

We supported four charities. Two reasons:

  1. I have multiple interests, and that includes issues that need support. Just choosing one seemed off.
  2. These are local charities. They have small budgets. So if we give $100,000 one year and then pull out the next – that’s a big hole for them to fill. The smaller amount also ensures that us not doing these anymore (which, as you know, we are not) means things don’t break.

So the charities we donated the money to:


The Cookie Off was a big success

We did well. I would even go so far as to say I think we killed it. I tried to set the tone that this was more a house-party of dope people than any kind of formal or professional ‘networking event.’ The messages I got from attendees this year (versus last year) was far more positive and enthusiastic.

I’ve uploaded over 200 pics of the foods and fraternizing of the eclectic bunch of people that attended.

Futhermore, we ended up raising over $175,000!

My buddy Alberto Alvarez chipped in $20,000. And then my buddy Jayson Gaignard surprised me with another $20,000. I could go on and on about them, but I will be succinct: irrespective of the donations, they are both fucking amazing humans, and I consider myself fortunate to have met them and befriended them.

Lastly, we ended up donating over 200 pounds of cookies and enough food to feed over a hundred people to local shelters.

People loved the event. We raised over $175,000. We donated over 200 pounds of cookies and enough food to feed over a hundred people.


Two important lessons

There are many lessons to take from all of this, but I will give you two quick ones:

1. The idea of putting something out there and it panning out is only true if you actually “do.”

From the very first food off (which was just amongst friends), I’ve been hearing how others are gonna do the same.

From when we raised $1000 at our first official one… “I’m gonna do it.”

$8,000 from sausages… “I’m gonna do it.”

$30,000+ in NYC… “I’m gonna do it.”

$100,000+ last year… “I’m gonna do it.”

And now over $175,000 this year… “I’m gonna do it.”

We know via social media that people love having opinions on things they have no business having any opinions on. Similarly, people love saying they will do something when they have no intentions of doing something.

(And when you do it, do it right and solve the problem).

People love talking; if you actually put yourself out there and do something, others WILL join you.

2. Don’t hang out with the same kind of humans

The most common thing I heard was: “I met a lot of interesting people from different backgrounds, and they were all so friendly!”

I wrote this a few years ago:

People often ask me how I know so many people.

  1. Read something that is cool or interesting
  2. Contact them and say “oh hey I enjoyed this”
  3. Repeat #1-#2

You hear from the haters all the time, and rarely from people who like your work.

But the key here is that it introduces you to people outside of your bubble. Very frequently at events you have people from the same circles, over and over. Even in “entrepreneur events” it’s often the same people from the same damn circle.

Diversity isn’t some token phrase to give lip service to – it’s something systematic that enriches the information and data you are exposed to.


With all that said and done, I’ll likely cook up something else zany for me to occupy myself with. What that is I still have not figured out…

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