#cookielife – how I convinced 200+ people to send me cookies and raised over $400,000 for charity

The ad-hoc #cookielife, something that spawned out of friendly banter over on Facebook, resulted in over 200 people sending me cookies via the mail and also spawned my charity food offs, which raised over $50,000 for charity in 2017, then over $100,000 in 2018, and then finally, over $200,000 from the last ever Cookie Off.

A collective total over $400,000.

A fair number of humans were exposed to my work through my love for cookies and thought it was some genius personal brand marketing.

Not. Even. Close.

You may be wondering – how did it all start?

By going for the ask.

The sweet tooth and losing weight

Growing up, I always had a sweet tooth. At the precocious age of nine, my mother taught me how to bake chocolate chip cookies. After that, access to chocolate chip cookies was always a few hours (and a well-stocked pantry) away.

Fast forward a few decades to 2009, when I started to whittle away all the fat I had accumulated on my body.

The thing is, losing weight sucks. You’re in a caloric deficit, and your body is yelling at you “why are you doing this to me??” And so to maintain my sanity, I found that limiting myself to a cookie a day made it much more bearable.

Furthermore, to resist having temptations around me, I never had any at home. Instead, I’d go to a local bakery or cafe or story, buy a single cookie, and then eat it on the way home.

Thus, a delicious treat was had, adherence to a negative caloric balance was affirmed, and my environment remained sans-treats, ensuring I didn’t inhale them and KO my weight loss.

Mind you, the bulk of my diet was veggies and lean protein.

Eventually, I settled on a local cafe as the best of the best. Gooey, fudgy, chocolate… they were everything one could ask for in a chocolate chip cookie.

I ate cookies while I lost weight. It helped me stay consistent in maintaining a calorific deficit.

Forget “pick your brain” … “I’m here to bribe you with the best cookie.”

Ask anyone who is in a position where they get unsolicited connections, and they will say that nothing is more eye-roll inducing then “hey I’d like to pick your brain.”

To be caustic: why? Why would I take out time in my day to meet with someone I don’t know to act as a free consultant?

Eventually, it becomes a matter of triage and prioritization. You get so much inflow that it becomes hard to balance maintaining existing relationships and meeting new humans.

So when I started building relationships here in Toronto, when I asked people out, I never ever ever said pick your brain (nor was I attempting to). Instead, I said I’d bribe them with the best chocolate chip cookie they’d ever had.

This accomplished multiple things:

  •   It set me apart. At a bare minimum, it was more interesting than “let’s coffee”
  • It exposed a facet of me: my interest in baking. I love cooking and baking, and food is an amazing way to connect with others
  • Everyone loves cookies!

“Pick your brain” is the easiest way to get someone to “no thanks.” I instead offered a chance to eat the best chocolate chip cookie ever.

Meetings and how trash-talk lead to the original cookie off

A fair number of readers know that you will likely find me at the cookie spot on Fridays.

Pro-tip: I set it up so that I’m meeting with someone every 30 minutes.

The goal is not that the person leaves after 30 minutes. Instead, I want them to stick around and meet the next person who rolls in. It’s the network-effect ramped up, and really builds community.

Over the past 6 years, I must have met over 400 entrepreneurs at this location.

If you’re frequently meeting with people, have a central go-to spot.

In Nov 2015 I met a lady named Kara Agostino. We met through mutual friends in the fitness industry at her husband’s restaurant (Libretto – best Napoli-style pizza in Toronto). We started debating on what the best cookie in Toronto was. Instead of it just being a war of words, I invited her to the cookie spot the next week.

At our coffee date, Kara and Lavanya (a friend who I wanted Kara to meet) sat down, each took a bite, and immediately conceded – truly the best cookie they had.

A week later, Kara had the audacity to post on my Facebook wall and say she had found better cookies.

Unimpressed by this bravado, her and I started to banter about the ridiculousness of her claims. Idiocy and madness on my wall!

Suddenly, in came Renee. I had no clue who she even was – she was Kara’s friend, and not someone I knew.

Renee immediately upped the stakes and said she could make better cookies than both of those cookies.

I was now concerned – the madness was contagious, and the insanity was breeding like rabbits.

We continued to banter until I said OK, listen: The only way we can properly say which is the best is if we do a blind taste test.

They both agreed.

Then I said listen – Renee, you invited yourself to my wall, so I’m inviting myself to your house, you shall host blind taste test.

Renee, being a good sport, agreed to it.

We then started inviting people, and roughly a month later, the inaugural Chocolate Chip Cookie Off happened:

All because of the ask.

By embracing the absurd and going for the ask (focusing on do-ing and not just talk-ing) is why the inaugural Cookie Off happened.

#cookielife: cookies in the mail

After I posted the picture on my wall, other people started saying they could make better cookies.

OK I said, prove it. Send me your cookies.

The first person to step up was Laura. She lives in London, Ontario, which is a 2.5 hour drive away from Toronto. A friend of mine was visiting Toronto from London, so she drove to Laura’s house (who she did not know!) on my behalf to pick up the cookies and then delivered them to me… at, of course, my cookie spot.

Once I posted a picture of that, the floodgates opened.

What’s hilarious is the entire sequence would mainly consist of me saying “oh hey, how come you haven’t sent me cookies?” The typical response would go something like “true; what’s your address?”

Even more absurd: people would start convincing their friends and significant others “you make delicious cookies, you should send them to Sol.”

When I went rally racing last year, my buddy Jim Umlauf showed up with cookies. Why? Because his wife had harangued him about it, saying he had promised me some!

As with most things in life – once you have a bit of momentum, it just starts going faster and faster on its own.

I’ve talked to a few friends about it, and I think there’s a multitude of reasons on why it clicked:

  1. It was ludicrous. Being part of something ridiculous and different was fun.
  2. It was ad-hoc. There was no central webpage. No Instagram. It was just something that was happening in a very very tiny corner of the web.
  3. It was an expression of gratitude. A fair number of people sent me cookies as a way of saying thanks for all my advice and pontificating on Facebook and SJO.
  4. There was no commercial purpose. I don’t sell cookies. I have no professional connection to cookies. This wasn’t something I did to make me money.
  5. It brought people together. I think people wish to be part of something bigger than themselves, and in a small way, this delivered.

I have a stack of 100+ notes/cards that people sent along with the cookies they sent. I am incredibly appreciative of all the kinds words contained within, and I find those words to be sweeter than the cookies that accompanied them.

An interesting quirk was because I lived in Canada (and shipping to Canadia is not cheap), whenever I mentioned I was traveling somewhere, people would ask for my hotel’s name so they could send me cookies. NYC. Seattle. Denver. DC. San Francisco. LA. Chicago. I’ve had cookies waiting for me every time I dropped by the US.

And it wasn’t always cookies. In Boulder I got a chocolate chip cookie pie. I got a fair number of pies. When I went to the UK, someone made a spotted dick, but replaced the raisins (which are repugnant) with chocolate chips (woooo). I got a ton of chocolate, including a package from Vietnam that had chocolates that the NYT had said were delicious:

My middle-school gym and math teacher (dude is jacked and brilliant) sent me his favorite peanut butter (which combined with some pineapple jam I got from Hawaii made for some of the best PB&J sandwiches I’ve ever had)!

I cannot even begin to start talking about how many times I’ve been tagged in random cookie-related posts on Facebook…

Most importantly, there was never any master plan with this. It was something I just ran with. And people loved being a part of it. It was special because it just… happened.

Even the tag was just something I started using ironically and took a life of its own when people adopted it.

The #cookielife started because I asked for cookies, but it happened because it was fun, atypical, and an extension of my own personality.

Charity Food Offs

The beautiful thing about something that is ad-hoc is you can do whatever you want with it.

I’ve written about the Chocolate Chip Cookie Off 2017, the Sausage Showdown, and then the NYC Chocolate Chip Cookie Off. Collectively, they raised over $50,000.

What I’ve never written was how it happened…

Kara and her husband helped host food offs at their house in 2016 – we had a Pie Palooza and a Monster Mac n’ Cheese Off (which, ahem, I won).

About 3-4 months before 2017 rolled in, people started to ask me if a second Chocolate Chip Cookie Off happen. And if so, could they attend?

I’ve talked about leverage, and sensing an opportunity to do something I had never done before, I decided to make it an event.

At the same time, I had no desire to get into the event space, so I decided to make it about a charity

The How I got 27 profesional chefs/bakers to make cookies explains how I did it, but it was a whirlwind. I am super lucky that I have a partner who knows about food and events, and she helped connect me with a friend of hers who had an event space. My friends all rallied and became my volunteer team. I was able to convince those 27 pros to compete, and the cookie off upgraded from “yay we’re just having fun at a friends’ place” to “woah, we’re at a professional space with professionals competing and we’re selling tickets to raise money for charity!”

Everything after that came as a consequence of trying to take it to new heights.

Can we do something savory and have people fly in? Sausage Showdown.

Can we host it in another city? NYC Cookie Off.

Can we make it a networking event that has people fly to Toronto? Toronto Cookie Off (70 people flew in, over $100,000 raised).

People wanted to be a part of it, so I gave it to them: Food Offs. But to make it true to who I am, I made it about charity, connecting people, and delicious foods.

Ending the #cookielife and focusing on charity food offs

Around the middle of 2017 is when the #cookielife peaked, I was getting 2-3 batches of cookies a week.

Great for my insatiable sweet tooth, but bad for my waistline.

I also realized that it had reached its peak… it was no longer as thrilling as before.

There were suggestions that I start building a brand around it, but that was never the point. It was always about something fun, and I had no desire to make it into a grand story.

Some people thought this was an exercise in personal branding, but they could not have been more wrong.

It was but a facet of me, not all of me.

I even got these RIP cookies:

Furthermore, with the charity food offs becoming big, it made more sense to focus on them.

Just to give you a sense of perspective, the amount of money raised:

  • Chocolate Chip Cookie Off 2017: $2000 (actually roughly $1000… I topped it off to hit $2500)
  • Sausage Showdown: $8000
  • NYC Cookie Off: $30000+
  • Toronto Chocolate Chip Cookie Off 2018: $100,000+
  • Toronto Cookie Off 2019: $200,000+

The NYC Cookie Off funded two girls born into the untouchable caste in India from K-12. Two girls who would not have gotten an education are now getting one because of the event.

That’s important stuff; that’s a responsibility I now have.

Right around the peak of #cookielife was when I knew it was time to wind it down, especially as the charity food offs started to explode

Introducing the Sol Cookie

Every birthday my woman makes me six desserts. I don’t even know how we settled on six… I assume five seemed too little, and seven just seemed ostentatious.

In 2017 she threw a curve ball. For the sixth dessert she convinced Milton, purveyor of my favorite chocolate chip, to make a giant cast iron version:

To say it was buttery chocolatey goodness would be an understatement for the beast it was.

I spent the subsequent 12 months haranguing Milton to not only sell the giant cookie to the public but to call it the SOL cookie.

I’ve always wanted a food item on a menu named after me, and what would be more me than an enormous ridiculous 6000+ calorie chocolate chip cookie?

Roughly three weeks ago, my relentlessness paid off, and the man agreed to put it on sale. It debuted a few weeks ago:

For those that watched the brilliance that is Seinfeld, one of my fav moments was when George Costanza decides to leave all conversations “on a high note”

And so with the arrival of a giant cookie named after me, I knew it was time to retire the #cookielife.

I still love chocolate chip cookies. And I’d never reject cookies if anyone sent them to me. But the days of me going for the ask is over.

From cookies in the mail to charity food offs to having a giant delicious cookie named after me, the #cookielife begat much zaniness.



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