The concept of Drunk Entrepreneurs came about a couple of years ago. I was hitting the town with a friend, who just so happens to be an entrepreneur whose company has been growing very rapidly and gaining a lot of brand recognition.

We often talk shop and share strategies with each other in an effort to offer guidance where needed. However, this particular evening we had consumed a little bit more liquor than we probably should have. As a result our typically reserved conversation about high-level strategy, quickly transformed into a no-bullshit relay of our deepest thoughts relating to business.

It was eye-opening for me (or at least I thought so at the time while under the influence of my good friend Bourbon). Thus sparked a thought:

What would happen if I got drunk with more entrepreneurs? I could really learn a lot of things that might not typically be shared! Or at the very least, it would give me an excuse to drink with some cool people and claim it’s productive.

Now as someone who tends not to get over-excited about an idea without truly validating the idea first, I started casually bringing the concept up in conversations with various entrepreneurs and marketers. People liked the it and asked how they could sign up for notifications.

So I decided to buy a domain and start planning out the show! This was at least a year ago. Over the past year, however, I’ve run a few “test” episodes, if you will. All of these episodes went horribly wrong. I’ll go into more detail about that shortly.

I also spent some time reaching out to various entrepreneurs in my own network, but as much as they may be interested in the concept, it’s shockingly difficult to convince people to not only come to my house in Toronto, but on top of that they have to get really drunk with me. Oh and also I have no money so I can’t pay anyone.

The more I considered this, the more I put off the show. It made me anxious to have to depend solely on other people for a crazy idea I had after a night of excessive drinking. So what did I do? I drank. To drown away my sadness…

And then I had another idea!

What if instead of only inviting over entrepreneurs, I do some solo episodes? I can share my own insights about marketing and growth while drinking by myself!

Now I understand that drinking alone has it’s own problems, but that’s something that my future self can worry about. By the time my liver fails me, my hope is that Elon Musk has figured out how to save humanity from ourselves.

The point is, in order to successfully produce a web-series, I needed to be able to accomplish a few things at the very least:

  • I needed an opportunity to test quickly in order to learn what works and what doesn’t
  • I needed consistent content in order to build and maintain engagement
  • And that content had to be good- meaning it had to provide value while also being entertaining

I would like to disclaim at this point, that I usually don’t know what I’m doing the first time around. This is why I strongly believe in running “experiments” or “tests” while trying to find success in any project. The process is the same no matter what the industry.

You need to keep testing out possibilities in order to narrow down what is most effective.

Maybe you run a software company and are trying to get more traffic to your site. You run various acquisition tests until you figure out a strategy that works. When you find what works you double down on it.

Or maybe you’re trying to increase the conversion rate on your e-commerce site. You can run various experiments that target different metrics and that can possibly have an impact on your sales.

After enough iterations you typically gain one of two things:

  • You improve or fix the problem
  • You identify what doesn’t work

Identifying what doesn’t work is the first step to actually fixing the problem. It might take 1 shot, or it might take 10,000 shots, but at some point your going to consume enough shots that you will get drunk.

Why am I talking about experiments you ask? Well as I mentioned I tested out a few episodes before I decided on this new angle. Here’s what happened:

Failed Episode Number 1:

A friend of mine is the co-owner of a coffee roaster in Toronto called Hale Coffee. They have multiple cafes around the city and provide some of the best coffee I have ever tried (and I drink a LOT of coffee (because I drink a lot of alcohol and we all need balance)).

The point is, since he is a friend and lives in the city, I figured he would be a great first guest. Since this was the first episode we would be shooting, and there wasn’t an established format just yet, everything was really just up in the air.

A couple things I learned from this first episode:

  • The interview went on too long, which made it really difficult to edit down.
  • There is such a thing as too much alcohol, and my friend ended up passing out (making it a bit difficult to continue the interview).
  • The set up was over-complicated and too much emphasis was placed on production value rather than content.
  • There was very little structure to the interview and drinking process, which I believe is what lead to the above two points.

Needless to say, it probably would have been a better idea to actually have a specific set of questions to ask, and stick to just one camera to keep things a bit more simple.

Failed Episode Number 2:

I’m actually quite disappointed that this episode didn’t turn out well, because I think it had some potential to be great. Nathan Chan, the CEO of Foundr Magazine happened to be flying through Toronto. We made plans to get together and I coerced him into helping me with an episode of Drunk Entrepreneurs.

A few new problems arose from this particular interview:

  • Nathan was sick, so he didn’t want to drink too much. Unfortunately the show is called Drunk Entrepreneurs, not Sober Entrepreneurs.
  • I did format the questions better, but this time because Nathan had so much to say, I ended up drinking while he spoke. As a result, I got too drunk…

Overall, I learned that I should probably have a conversation off camera with the guests first, and during this time start drinking. This way, by the time the filming starts…we are both equally intoxicated.

I also really didn’t like the interview format very much. It was too formal and was lacking that organic element.

Next Steps And What’s to Come

You probably have a lot of questions and might be wondering what this means for Drunk Entrepreneurs?

I can assure you that it will still be a show in which I interview entrepreneurs and we drink together, but it won’t only be that. As an entrepreneur myself, simply drinking alone is technically fitting with the concept of Drunk Entrepreneurs…except it’s more like Drunk Entrepreneur (singular).

There will just be more of a balance between having guests, and being stuck with me.

But here is a sneak peak of some episodes which are scheduled for release:

  • How to Get Press Mentions With Manhattans: An episode in which I attempt to show you my process for getting high quality press mentions for major sites.
  • How to Handle Negative Feedback and Rejection (Special Guests): In this episode I go through some strategies on how to deal with rejection, and what you can do to help feel less trash. And yes, there will be some special guests featured on this episode!
  • How to Come Up With Content Ideas When You’re Blocked: I’ll walk you through a high-level strategy for identifying quality and SEO friendly content ideas so you never run out of awesome content for your audience.

If there is anything in particular you’d like to see, please leave a comment on this post, or on YouTube. Make suggestions, or simply heckle me. It’s your prerogative. But chances are if you heckle me I’ll probably just use it as leverage for the second episode on that list.

And if you have an entrepreneur in mind who you think would be a good fit (and will actually follow-through) you can nominate them here.

Finally, don’t forget to subscribe to the Drunk Entrepreneurs YouTube channel so you can get notified when new episodes go live!