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Rules for Life

Delayed Gratification is the Winner’s Way

I’m going to share a personal story with you that begins at the start of the pandemic. I was leading sales for an ad tech startup, but we were exploring potential suitors as we prepared to be acquired. It was a frustrating time because after three grueling years, I felt we had finally figured out the message, product positioning, and hired the best team. The company was also poised for a record revenue quarter. We ended up being bought by a larger company in our space, and I could not have been more disappointed. Usually an acquisition is celebrated because you’ve made it to the finish line and you’ve probably made a nice payout, too. Unfortunately, this wasn’t the case back in March 2020, with covid-19 destroying any negotiating leverage we had, and limiting our amount of partners, too. We ended up taking a deal that included an earn out, with no cash up front, and I was set to join the staff of the new company.

Being part of a large, financially stable company during a pandemic is certainly not a bad thing. However, this situation disgusted me for a variety of reasons. I was being demoted from a C-level position down to a regional leader role. The pre-negotiated salary increase I was due in May ’20 had been shut down with no rationale other than “we’re not going to be able to give you that”. The commission plan I had been on was changed overnight and went to complete dog shit; from 10% to 2% … fucking highway robbery. Throw in the fact that the new company loved to have meetings about meetings, and I was absolutely miserable. My first instinct was to quit immediately; find some other company that could use my services and bounce the hell out of the purgatory I found myself in. That wasn’t a realistic option for a couple reasons. I did not want to screw over my previous boss, who was the founder of a new company and would be financially tied to the earn out I was part of. On top of this, covid-19 left the advertising industry in very unchartered waters. It would be too risky to leave for a brand new company because all of my stability would be removed. I knew I was stuck there until the end of summer at the earliest.

Once July rolled around, it seemed like many companies started recruiting again. I was approached by headhunters several times. I took a few calls, more to see what was out there than anything else. To my disappointment, nothing out there “checked the boxes” for me, and I was stuck in arguably the worst job of my career, in front of a computer screen for anywhere between eight to twelve Zoom calls per day. Again, I could have just quit and continued to earn income from consulting, but logic got the better of me. That would have been an emotional decision, which are the worst kinds of choices to make when it comes to business and money.

So, I bided my time while placating the new overlords I reported to. It was soul-sucking work, no doubt about it… but the paychecks kept coming in, the benefits were stable, and deep down I knew I could handle it. Jocko Willink’s book “Extreme Ownership” taught me a valuable lesson about pain. Whenever you’re experiencing terrible pain or exhaustion, know that your body can handle 60% more. Even though this sucked, I had to push through until I found the best new opportunity for me. Fall came and went, and before I knew it we were celebrating the holidays. Still no new job. It was frustrating, annoying, and painful. I started to doubt myself as a C-Level executive. Negative thoughts would flood my mind:


“Maybe you’re not cut out for this?”
“You probably aren’t good enough”
“Most companies realize you aren’t as good as you think you are”
“You’ve overestimated yourself. Nobody is going to hire you for that job” …

Every time this happened, I pushed those thoughts away and reflected on the big wins I’d achieved in the past and what it took for me to accomplish these things. I also reminded myself of the poor economic conditions we as an industry were facing, and the uncertainty everyone was experiencing. “Just keep pushing and eventually you’ll find it” was my baseline mantra through January. It is dark and cold in the winter. These are conditions ripe for depression. I would not let it take me.

“Think about how sweet it will be once you end up in your next job.”
“Visualize how much money you’re going to make in 2021.”
“In six months you’re going to be sitting in a hot tub laughing about how worried you were.”
“This will pass…”

All these thoughts, plus a combination of lots of exercise (I took up boxing) and a healthy diet complete with vitamins D and zinc kept me grounded. Then, in mid-February, I got the call. An old colleague reached out to see if I would be interested in a Chief Sales Officer job at his company. Apparently, revenue numbers had been dismal for two years, and the CEO told him to go out and “find the new CRO”. I was his first phone call.


I went through the interview process and met the management team. Within a couple weeks, it was pretty obvious this was a perfect fit for both sides. They flew me down to their office in Florida and we talked about the strategy, vision, and comp package. We had a handshake deal. I headed to the airport with the energy and enthusiasm of a winner again. By mid-March, I had signed my employment agreement, resigned from the most boring job known to man, and was on my way to my next startup adventure. Absolutely none of this would have been possible if I gave in to my emotions and made rash decisions because I was upset.

We live in a world that rewards impulsive behavior. It is an “on-demand” society that gives us access to whatever we want, instantaneously. This culture spawns one of the most detrimental behaviors to success; a true lack of discipline. If we expect to get what we want as soon as we want it, how can we commit to the long term with goals, systems and processes in place? Our discipline goes out the window. Instant gratification is expected. The idea of “delayed gratification” gets lost. If you’re not familiar with that concept, it is defined as the following: the act of resisting an impulse to take an immediately available reward in the hope of obtaining a more-valued reward in the future. The ability to delay gratification is essential to self-regulation, or self-control.

Champions and winners understand this concept better than anyone. Adhering to these guidelines is what helps to build a successful frame. Olympians don’t achieve elite athlete status overnight; it takes years of game plan, preparation and sacrifice to achieve this level. The same goes for founders of big successful companies like Amazon, Google, and Tesla. These organizations are not built overnight. Long term game plans, with steps, objectives and milestones are what’s required to build towards that larger success. The only way you can achieve this is by being disciplined and delaying gratification.

It means seeing the big picture and knowing how you will get there, even when the path directly in front of you looks challenging or murky.


I would not be in the position I am today if it were not for delayed gratification and discipline. I did not give in to my emotions and take the easy way out. I stayed on course until the conditions were ideal for my next move. Remember this lesson the next time the voice in the back of your head tempts you to quit or go off course because things are not easy. Do not give in. Stay strong.

– Your Big Bro

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