⚡️ Today’s level up ⚡️

Today’s edition continues the breakdown of my complete journey from childhood, through my time in sales, to today as a one-person business operator with over a $5M net worth and the freedom to follow my ambitions on my terms. My goal is to illustrate how being highly purposeful throughout this journey has yielded financial independence, solid relationships, good health, and memorable experiences.Let’s go!Read time: <15 minutesIf you missed last week, read it here.

Recap of our journey together so far

As I mentioned in Part I and Part II, this series goes deep, so it’s not meant to be a quick read and take action, like my usual guides, playbooks, or breakdowns enable you to do. That’s by design.I invite you to set aside quiet time to get serious about your career and life. Are these two forces moving in harmony or is one fighting against the other? If you don’t take time to zoom out and ponder the bigger picture, it becomes too easy (and comfortable) to get swept up in the chaos.Chaos, which is really just a world designed by others, breeds mediocrity.I suspect you're seeking something more than just scraping by. I know this feeling intimately, as it drove me throughout my own journey. That's why I'm sharing my story in such detail—so you might discover an insight or spark of inspiration to catalyze meaningful change in your own life.I started this series in Part I documenting my childhood and the pursuits that led me to sales in early adulthood. It includes the good, bad, and ugly. I feel all humans are on a diverse spectrum of experiences, backgrounds, genes, and personalities. But what bonds us is our ability to think differently and innovate based on those ideas.Sharing my story is not always easy, but in the grand scheme, I know I’ve had it far easier than way more people on this planet. Hardships are opportunities to get better and connect us to others who share a similar “frequency.”Scars, not status, are what bond us together more tightly.In Part II, I deconstructed my journey through Level I: The LEARN Stage. The key insight was that my attraction to sales stemmed from possessing an entrepreneur's heart, even if I hadn't yet developed an entrepreneur's mind. This apparent mismatch, however, proved to be a significant advantage in the long run (as you'll discover in this edition, Part III, and in Part IV, the final installment of this series).Learning (about myself, the business world, the nature of sales, influencing others, and so much more) was best led through my heart, not my brain. That’s because it was the time of my life where I could genuinely discover what I liked and didn’t like. It was the period where I could make mistakes, take the biggest risks, and learn from the consequences of those mistakes and risks. Learning from inside my heart center was what provided the clarity to build the right muscles for my brain to take over and lead in Level II: The EARN Stage.Here’s a simple graphic that illustrates the driving Modes within each stage.

Of course, all Modes are in motion at all times, but there is one main driver while the others act as supporters depending on what stage you’re at. Let’s dive deep on Level II and use Brain Mode as the driver for earning life-changing leverage that opened up the pathway to Level III sooner than I could have ever anticipated.

Level II: The EARN Stage

Here I am apprenticing under CEO Tom Frost (on whiteboard) at DatumAfter a year at Datum, the regional IT outsourcing and consulting firm in Sarasota, I was ready to move back into the SaaS product space, but this time going up market into Enterprise.I felt ready. Several factors empowered this decision.For one, I learned how to construct the biggest deal of my career up to that moment - a $1.56M deal with a multi-unit restaurant group based in South Florida.Granted, I had a lot of help from the CEO, Tom, who I was shadowing to close the deal, but I sourced it and opened the door using a simple LinkedIn + Email + Phone sequence and in-person package drops with letters (ok, they weren’t as sexy or creative as what Dale Dupree teaches his Rebels with the Crumpled Letter move, but it worked), ran the ROI analysis, and structured the onboarding. It was the first time I was able to witness and construct a full TaaS (Technology-as-a-Service) deal.Second, I was able to apply the things I knew well (like upgrading the company’s website and creating more entertaining marketing) to enhance the company’s brand on a national scale. No, these were not in my immediate job description or scope, but I did them anyway because I enjoyed them, I was good at those skills, and they ultimately helped us chase more business. It was the entrepreneur’s heart beginning to merge with the entrepreneur’s brain.Third, I was able to accelerate my learnings of a space I knew nothing about (multi-unit restaurant technology and operations), and within eight months, start earning from it. That was a powerful discovery. A spark.However, it became clear I was going to need a bigger space to spread my wings.

New York Times article highlighting a big investment in RevelI gave Datum a full year (which felt more like ten - if anyone knows the restaurant space, it’s exhausting, even on the tech side, err, I mean, especially on the tech side). I knew it was the right time to make a pivot for me. I was still leading with my heart at this stage, but I was getting smarter on how I would reap the rewards.

Tip: Always leave with grace and the door open to do more business with your old employerEnter Revel.I now had the confidence, the point of view, and ability to pursue complex deals in the enterprise restaurant space, and Revel was the right vessel for me to do it in.Luckily, Datum exposed me to the best-of-breed tech players in the enterprise restaurant space - Olo, HotSchedules, and Revel. That gave me a short list to strategically approach all the companies that felt like the best environment and product for me. Honestly, Olo was at the top of my list, so I reached out directly to their CEO first (who replied within two minutes to my LinkedIn DM).

My LinkedIn direct message exchange with the Founder and CEO of Olo in early 2015Sadly, by the time it got to Marty Hahnfeld, their CRO at the time, he had already filled the position and wanted to keep the team lean. I think things worked out pretty well for them, so I can’t get too upset. (I’m friends with Juan George, who was a part of their golden growth years, and I still remain a bullish investor today.)That’s when I connected directly with Revel.

The DM that opened the door with Revel’s Corporate RecruiterAfter earning the role via a series of virtual interviews, I insisted on flying to their HQ in San Francisco to meet in-person to get a feel for the vibe and culture while also walking them through the ROI analysis and justification on my higher counter offer (which I got).I joined a lean Enterprise team of two (me and my manager, Jake). We were tasked with selling the future to massive brands.Revel had made a name for itself in the independent and small restaurant group space and aspired to go upmarket into true Enterprise, like so many SaaS companies in 2015 (and today). That was both a challenge and an opportunity. On one hand, it was challenging because with no proven (true) enterprise capabilities out of the box, it was tough convincing CTOs, CIOs, and COOs to risk their reputations on an upstart. On the other hand, that meant focusing on real innovators and those that understood where the future was headed was an exciting proposition.I leaned heavily into the latter camp.But first, I was immediately thrown into the lion’s den. The first account they gave me was a “trouble account.” It was Revel’s largest enterprise customer at the time, a pizza chain out of Dallas, Texas. The CEO sold it, passed it on to Bobby the CRO, who then passed it down to my manager, who then passed it on to me. Gee, thanks!They had been oversold and received under delivery on the services they thought they deserved. I had to play reputation repair builder. Luckily, my experience with a trouble client wasn’t foreign to me, as I had experience with one at Datum, particularly with unhappy franchisees, of which this pizza chain had many.Instead of trying to figure out how to sell them more, I first committed to getting to the root of the issues. After having a handful of conversations from upset leaders, it was clear they felt a.) nobody was caring for them and b.) they didn’t know how to fully use the product, which stemmed from a lack of training, which subsequently resulted in constant issues at the restaurant level.I agreed to the client that I was going to get our best trainer to come with me to Dallas to do a custom two-day training summit where all of the local franchise owners could come and get hands-on training. We were going to break down their top company-wide issues and work through them one-on-one for several hours over the two days until we had them fixed and everybody had their questions answered.To convince the company to allow me to do this (remember, they were still on a lean startup budget, as the PE funds hadn’t hit the bank account yet), I created another ROI analysis for Bobby to showcase what the travel and time expense could yield if I could parlay the training into sign-ups for a packaged deal on new systems and units.The training was eagerly welcomed. Corporate was happy that someone was actually coming to them in-person and listening to their gripes, and the franchise owners finally felt empowered to leverage the full capabilities of their powerful setups. I was able to turn the trip into a profitable oneI was now thinking like a real entrepreneur to solve problems and create profits.I went on to have a great few years at Revel. Multiple President’s Club trips, awards, and a perennial top five company-wide producer. The thing that started to really materialize for me was the power of skill stacking. I was bringing in my passion for iPad technology with the consumer marketing behavior strategies I learned at ReachLocal with the TaaS packaging I learned at Datum.My Brain Mode was in full activation.

Hitting the red carpet at Revelry, our big annual event with customers and employees. Not exactly sure why I was looking so smug?At the end of 2017, opportunities started coming to me. I was often solicited from recruiters, but rejected most of them. However, I did keep a mental list of two columns:1. A handful of select marquee companies2. Transformative industriesOne recruiter caught my attention, as they represented a company in the second column I was tracking - conversational AI.Out of curiosity, I took the call. After liking what I heard, I agreed to talking with their in-house recruiter. The more people I talked to and the higher I climbed, the more excited I got. However, I was happy in my role at Revel. I had increased my earnings by 65% since Datum and was given a fair amount of freedom to do my thing.This is where I wanted to put Brain Mode to the test and use a framework, not just my heart, to make an important, strategic decision.Despite having no specialized knowledge of conversational AI or experience in customer care, the main area where the company was focused on improving operations with their solution, I won over their executive team with my philosophy, not my direct experience.

Moving to LivePerson was like stepping into the major leagues for me, but not in terms of company size or the company name, but more so on the type of logos I’d have access to pursuing - the Fortune 500. That was a bet I was willing to make, especially after running it through my decision framework.I’ve written extensively about my fears and successes at LivePerson, and how that parlayed into life-changing confidence, earnings, and leverage in the four years and three months that I spent there, so I won’t go too deep into the specifics of the deal wins here.However, I do want to give you more of an insider’s view on what this change felt like, big decisions I had to make, and the transitions I started to think about as the next Level started to come into clearer focus sooner than I had anticipated.

Me talking with a strategic prospect at one of our white glove events in Silicon ValleyIn 2018, my first full year at LivePerson, I grossed just over $200K in earnings. The following three years, I averaged $1.1M annually to rake in over $3.8M in my tenure there. That’s a big leap and can play tricks on you mentally. Here’s how being in Brain Mode kept me grounded and making smarter decisions.

Writing.Yes, it sounds simplistic. In a way it is, while also being a profoundly powerful tool. One, it’s educational for you as an individual. Secondly, it’s educational for your audience - whether that is for your prospects or a small tribe you’re looking to build on the side.Every time I wrote something (in a journal, an email, a memo for a colleague or client, a narrative business case, a post on LinkedIn), I both learned something and I taught something. Learning and teaching using the same exercise is the definition of high leverage.Whether it was trying to get a promotion, persuade a prospect, build an audience on social media, or simply remind myself of where I came from and what I really care about, writing was always at the center of my personal operating system. And it was the gateway to where I am today and how that introduced me to you.Level III: The EVOLVE Stage is where we’ll pick up next week.

An early gift and shaping what’s to come

I get invited to dozens of events and even more speaking engagements each year. I say no to all of them…except this one: Sales Success Summit.Back in 2021, when I was ramping down at LivePerson and my Level II journey, I was invited to speak for the first time at SSS. Since we were still smack dab in the middle of Covid and I have an immunocompromised family member, I chose to speak virtually.It was the first time I crystalized 7 STEPS TO 7 FIGURES before it became an ebook and the foundation of my current one-person business.It’s time to launch the next phase of this journey and incorporate everything I’ve been working on and learning from doing 1:1 coaching with hundreds of enterprise and strategic sellers like you over the past three years. I will be sharing it all, packaged up in what I call Purposeful Performance.You’ve been getting a glimpse of what that looks like throughout this series, but in Austin on October 7th, I’ll be unpacking it all in specific detail. This is your ticket, literally, to engage with me live in-person and go deep on developing a more purposeful operating system so you can sustain a high performance lifestyle (the only time to do so in 2024).Let’s shave off five, ten, or even fifteen years from your corporate career using sales. Purposeful Performance is a path.There are still some tickets available, and if you sign up using my speaker link, you get $300off your ticket price. I will also offer a complimentary 60-minute coaching session to subscribers who purchase a ticket.All you have to do is use my link, purchase a ticket between now and next week, share a screenshot with me, and in next week’s edition I will supply you with a Calendly link to book a 1:1 virtual coaching session with me.Will I see you there?

That’s a wrap!

Here’s how I can help you right now (big changes coming- get these while you can):

1 | Unlock the 7 Figure Seller OSLearn how to use design and systems thinking to become a 7 figure seller. There are 3 options to allow you to customize your learning journey.2 | Download The 7 Figure Open LetterGet the creative strategic selling strategy that landed a $5.9M deal with a top 4 major global airline. Bonus inside!3 | Book a 1:1 coaching session right nowYou can book a 60-minute coaching session with me (although the Pro above option provides access to 1:1 coaching with me at a 70% discount).