March 22, 2025 | Read online
"A good plan violently executed now is better than a perfect plan executed next week." General George S. Patton
I wear my Make it Happen shirt every…single….day.
It’s a mentality I’ve had for a long time.
It’s about not waiting for permission or for someone else to tell you what to do, or as Nike would say - Just Do It.
It could also be rephrased as “Figure it Out.”
I personally think we’ve lost the “figure it out” mentality.
I remember a friend telling me a story a while ago about how she gave a bunch of young employees a project to complete, left them in a Board room for a few hours and came back to see them all sitting there in silence waiting for her to come back.
She assumed they were done with the project but when she asked about their progress they told her they got to a certain point in the process and couldn’t figure out the next steps so they stopped and were waiting for her to come back.
Let’s ignore the fact that they waited over 45 minutes for her to come back instead of just getting up to go get her.
When they told her what they couldn't figure out, she literally opened up Google, typed in their question, found the answer and applied it within 2 minutes to address the issue.
This seems to be a growing issue that really concerns me. People can’t seem to figure it out on their own these days.
Everyone is waiting for someone else to tell them what to do with their jobs, careers, lives and more.
We all need to adopt the “figure it out” mentality if we have a chance at staying relevant moving forward.
With that, I thought I’d use this week’s newsletter to share a story of how I applied this mentality to the event I’m hosting on the 28th and share some learning lessons along the way.
SALES FROM THE STREETS:
Ready, Fire, Aim
About 5 months ago I saw Bill Burr post on Instagram that he was bringing Glengarry Glenn Ross back to Broadway.
My favorite comedian bringing the most iconic Sales plays/movies back to Broadway? Are you kidding me?
I bought 18 tickets immediately without knowing what I was going to do with them.
This was right around the time I was going back into the studio to rerecord all my content to get ready for the launch of my new Membership site.
My original thought was to use the tickets to promote my new Elite Membership package and bring everyone who signed up to the show after the launch but I really didn’t put much thought into it because I was busy redoing ALL my content, trying to close out the year strong and plan for the new one.
After the launch of the new site a few weeks ago I realized I only had about a month to figure out an event that could leverage the GGGR tickets I bought for March 28th. Not to mention that we had planned a trip to Puerto Rico during my daughter’s school vacation that was a week before the show.
Needless to say, I had to move pretty quick.
I got a few Elite members to sign up after the launch but not as many as I wanted so I decided to pivot to a new strategy and invite my friends and colleagues who I know would appreciate going to a show like this.
TIP: Agility is one of the most important skills we all need to improve if we want to stay relevant moving forward.
I didn’t think that going to the theater was enough of a draw so I had to think of what else I could do to make this an event everyone would get value from and want to attend.
I’ve thrown my fair share of events/parties and I know what it would take to get me to travel to NYC on a Friday night so I knew this wasn’t going to be cheap or easy if I wanted to do it right.
For those of you who remember, when I launched my membership, I also launched a monthly “Free Training Friday.”
The tickets for GGGR were for Friday night and I needed a topic for the Next Free Training Friday so I started putting the pieces together.
“I don’t have problems, I have puzzles” - Quincy Jones
The next phone call was to some of the sponsors I work with, specifically Linkedin.
I’m on their Sales [I]nsider team and have been working with them for a while on helping promote different features of Sales Nav as they roll them out.
I’ve also presented at their office in the Empire State Building at an event that Morgan Ingram recently hosted, which was great because he was one of the people I invited to my event.
My Head of Partnerships/Agent, Aneesh, led the way in getting LinkedIn to agree to give us usage of their office at the Empire State Building for the live stream event, along with lunch and a few sponsor dollars.
With the main venue locked in and the tickets to GGGR, I thought I had enough to start calling around to friends and colleagues to see if they’d be available and open to coming to the event.
I put together a short list of people who I knew aligned with my “Why” to elevate the people and profession of sales, were practitioners and not just “influencers,” and would be fun to hang out with.
My pitch was not very detailed. It included two questions:
- Are you available on the 28th?
- If I paid your expenses would you be open to coming to a banger event that I’m putting together in NYC that includes a live event at Linkedin’s office and tickets to go see Glengarry Glenn Ross on Broadway?
I told each person I called that I was working on the details but needed to know sooner than later if they could attend.
With very few exceptions, almost everyone I called said yes, some even canceling some pre-booked plans to make it happen.
Now that I knew the majority of people attending, I had to figure out the content, flow of the day and ultimately how to pay for it all.
Since Linkedin was hosting the Free Training Friday and their platform is something all of us use to build our own brands and sell our own products and services, it only made sense to make the content about Linkedin.
But, I didn’t want this to be your typical “Linkedin Tips” webinar. I wanted to show people how other practitioners and experts actually use the platform to do what they do.
With a quick call to Morgan Ingram to flush out a few ideas we came up with running sales “plays” on how to do specific actions using LinkedIn like 1) getting a meeting with a tier 1 prospect, 2) tracking and engaging with prospects and 3) sharing content and building your brand.
With the “plays” locked in, the branding for the event fell into place - The Sales Play - playing off the Linkedin “plays” we're going to run and the sales “play” we were going to see later that evening.
The url www.thesalesplay.io was still available so I grabbed it.
Now the challenge was what to do with the time between Free Training Friday (1:00-2:00pm ET) and the Show (8:00pm).
With such a high caliber group of people attending the event with so much knowledge to share I didn’t want to waste their insights or leave too much downtime so I decided to add another hour to Free Training Friday for a live streamed Roundtable Discussion.
But what should we discuss?
When it comes to attracting and engaging an audience, it’s always better to focus on what they want instead of what you think is important.
TIP: throw away the first 3 slides of your presentation deck (company background, awards and client list) and instead start with a slide of what you know about them with clarifying questions and then ask what they want to get out of the presentation and focus on that. (i.e. Sell to the 20%)
This is where I pulled from an idea that I came up with when Stefanie Boyer from the Sales School at Bryant University asked me to speak at their National Sales Conference last year.
As part of my presentation, I gave the students 10 minutes to research me using ChatGPT and come up with a thoughtful and insightful question for me. Whoever asked the best question got $100.
The point I was trying to make to all of them was to not waste an opportunity when you meet with someone by asking generic questions that can easily be answered with AI these days.
NOTE: “Tell me about your business,” “what are your priorities?” or “what keeps you up at night?” are some of the most insulting questions and statements you can make to a prospect or client. You should come in with a perspective or hypothesis on what their challenges and priorities are based on 10 minutes of research using AI tools.
Their questions were fantastic and everyone learned way more than if I had presented something or did a general Q&A.
I’m going to use the same concept for this Roundtable to get questions from the audience and whoever asks the best question will win $500.
Once you register for the event, you’ll get a confirmation email that asks you to submit your question.
As an added twist, you can use AI to come up with the question or you can come up with one yourself. After the question is answered and discussed by the group we’re all going to have to guess on whether or not you used AI to generate the question to see if we’re right.
TIP: Research the 18 attendees of the event to come up with a question that plays to all our strengths and interests or research one of us and ask a very specific question.
With the Free Training Friday and Roundtable set I still had about 5 hours to kill before showtime so what do you do on a Friday afternoon in NYC?
Happy Hour!
I used ChatGPT to describe the event, including the vibe I was trying to create and asked it to come up with some venues that were between the Empire State Building and the Theater.
After looking through a few options I found a private room at SPIN around the corner, that was perfect. I connected with the event coordinator and explained the event I was putting together.
When she asked for my budget, I told her I didn’t have one but wanted to do this right. I told her to walk me through the options and give me a quote for what it SHOULD be and we would take it from there.
TIP: This is why I never ask someone “what’s your budget?” because 9 out of 10 times sales reps end up selling to the budget number, not the actual need. Instead, I ask “has this been budgeted?” to see how far along they are in the process but then focus on what they need instead of the budget they have.
After getting the quote I did a little give/get negotiating and offered to help promote the venue to over 500k followers which got the price down to a point that I thought was fair for them and worked for me.
Happy Hours are always fun but how can we make them valuable?
That’s when I decided to keep the live stream going after the Free Training Friday and use the Happy Hour as an opportunity to interview each of the attendees one on one.
I’m going to ask each of the practitioners/influencers 4 questions on a live stream broadcast:
- What’s your favorite close?
- What’s your favorite story?
- What’s your biggest career mistake and what did you learn from it?
- A personalized question for each of them that I come up with
After they answer those, we’ll take questions from whoever else joins us on the live stream (Linkedin, YouTube, IG).
With the majority of the day planned I needed to figure out how to end it. I didn’t want to just go to the GGGR show and walk out afterwards and have that be it.
There needed to be a debrief and discussion about what we all just experienced.
I had decided to have my production crew (Mainstage Media) document the entire day so it only made sense to find a venue to get together after the event where they could record all our feedback.
I had previously booked a single room at the W Hotel in Times Square that is right next to the theater. When I was looking around for places to go after the show I saw they had a killer suit that would be perfect to bring everyone right after the show.
I used my Marriott Platinum Elite status to negotiate a discounted rate for the room and booked it for 2 nights so we could control the environment for the filming.
NOTE: everyone who registers for the event will get exclusive access to the recorded discussion after the show.
This event had now come together and was looking good but also… expensive…
I’m a believer that if you do the right things for the right reasons with the right people, things will work themselves out, including financing.
With Aneesh leading the charge and getting creative with some of our existing sponsors, we got them to agree to throw in some money to cover different portions of the event.
For instance we came up with the idea to have Otter record Free Training Friday, the Roundtable and the Happy Hour Q&A using its AI call recording function.
After the event we’re going to add all the recorded transcripts to a group so anyone who registers can use Otter’s AI chat function to ask ANY question about any aspect of the event they want.
Insightly CRM, stepped up to sponsor the Happy Hour where I’ll be asking the attendees specific questions, including one about what their wish list would be for a CRM. I know what my wish list is and that the Insightly CRM can address almost all of the items on the list.
The sponsor dollars don’t cover the entire event but they make it manageable for me to cover the rest which is all I needed since this wasn’t exactly something I had budgeted for at the beginning of the year.
With all the pieces in place we needed to come up with a landing page, registration process, promotional strategy and more in very short order.
With my COO Meghan as my rock helping to coordinate everything, David, my producer helping develop the resources and plan the story arc, and my Head of Partnerships/Agent, Aneesh, coordinating the vendors and workflows we were able to pull this all together in less than 3 weeks.
As I sit here today, Friday the 21st at 7:00am watching the sun rise in Costa Rica, the only thing I have to do now is get people to show up, which is where you come in.
If you want to learn specific Linkedin “plays” from experts, ask questions and gain insights from some of the best practitioners and people I know and have a blast along the way, then you’re going to want to sign up to reserve your spot today.
If nothing else, you’ll see how all this ends up coming together and how the “figure it out” mentality works, or, in other words, how to Make it Happen!
Let’s GO!!!
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