Mr. Long Money

You don’t need to be loud and obnoxious to make it in sales. I was home schooled + super shy, and I didn't come out of my shell until college. Fast-forward to now: • My teams close over $1.6B in sales per year • I've done 2,000+ interviews and made 200+ hires • I took a client from $1M gross at negative margins to $4.2M gross and $1M a year in profit • I was hired by @clientascension as a Sales & Negotiations Coach. And I was largely self-taught. Most days it was just me, some textbooks and a library. Being the shy kid meant I spent most of my time listening and observing. College brought me out of my shell, but I never stopped listening (12 years into sales, and it's still the skill I lean on most) It's also why I can usually find the main problem in a sales call within the first 10 minutes, without even reviewing the pitch. More than 90% of the time, that problem is in discovery. A deal gets lost in the presentation maybe 1% of the time. So the talking part is almost never the problem. The listening part is. In the first 5 minutes of a call, I'm listening for tonality and frame: • whether the prospect believes the seller • whether they see themselves as higher, lower or equal in status to the seller I still prefer to listen. PS Want me to listen in on one of your teams’ sales calls? I’ll find exactly what’s killing your close rate. Message me and we’ll find a time.

“we need to improve our objection handling” My sellers closing cold traffic above 40% only RARELY get objections. Whenever a seller of mine hits that level, the team wants to hear how they did it. So I play the recordings. 9/10 times, it’s a simple straightforward sale with no objections. TL;DR: If you’re having to improve your objection handling skills... NGMI.

My sales teams went from closing $50k a month → $6,000,000+ a month. Along the way, I learned that "I need to think it over" isn't an objection at all... (free video) It's actually a symptom. What happens when most reps get hit with this objection: > Your closer drops the price at the end of the call and hears the stall. > So he does exactly what he was trained to do > He asks “is it the price? Or the timing”… > Then “what would need to be true to move forward today?” Every single one of those questions only digs the hole deeper. The prospect feels the pressure, stops thinking WITH your closer and starts hunting for the exit. What most reps don’t understand, is that the deal was lost in discovery, when a concern nobody asked about got left on the table with a lit fuse… So, I'm giving away my video on how to actually handle this objection, once and for all. In the video, you'll see: 1. A role play of the average rep asking the same question 3 different ways 2. The difference between a prospect in an "escape state" and one in a "thinking state", and why it gets decided in the first 5 to 15 minutes of the call 3. The discovery question that pulls the unspoken objection out before the price drop 4. Why the objection YOU bring up early wins, and the one THEY bring up late loses 5. What to do if it still comes up 6. An end-of-call role play example Want me to send it over? Details are below: PS - The discovery role play has the line I call one of the most powerful in sales. Steal it for your next call.

Was chatting with a seller who went 0 for 16 on his last 16 sales calls (and this is a guy who hit 200-300% of quota as an SDR in enterprise software). Now he's selling his own offer, for his own agency. We pulled up one of his recorded calls, and the problem showed up within minutes: The prospect wanted to double revenue in the next 12 months. So he asked: "If nothing changes, do you think you'll hit that 2x mark?" Prospect: "Yeah, I think we can." That answer ended the sale right there. If they're going to hit the goal anyway, there's no gap. And if there's no gap, why are they even on the call? Ask anyone if they'll hit their fat loss goals, and they'll say yes. Why? Because humans are IRRATIONALLY optimistic about the future. So, I had him swap the prediction question for “reality testing”. What did their current marketing actually bring in over the last 3 months? Annualize that number with them, right there on the call. When it falls short of 2x, they’ll say it out loud. NOW there's a gap to sell into.

After helping my sales teams close $1,600,000,000+, this is the 6-step discovery process I’d teach any closer: 1. Get a goal number first. Don't let other discovery questions crowd it out. With no goal, your pitch has nothing to tie back to. 2. Ask what happens if they do nothing - what’s the true cost of not solving this? When they deflect, press it. This is something you can NOT go without. It will be extremely important and gives you the upper hand later on. 3. Keep digging after the first pain they hand you. At that point you've usually found about 10% of the pain you need. People give up their pain very very reluctantly and only to skilled interlocutors. 4. Don't accept a vague answer to any of it. Hand-waving in discovery almost always kills the deal, so ask again until the answer is specific. 5. Anchor your pitch to the goal number from step 1. When your ROI projection hits that number, say it OUT LOUD. 6. Tie it down before the call ends. Get them to confirm the plan gets them to their number. Then they're the one asking how to start. Bookmark this + send it to your team.

Was chatting with an owner whose star closer collected $150k in cash one month, and $30k the next. This closer was a former baseball player. They'd been streaky in sports too, so the hot and cold months felt normal. The real cause was actually outside of work. Life at home was knocking the closer around emotionally. Where a bad week there turned into a bad week on calls. So the owner's cash collected essentially relied on how the closer's week was going at home. No bueno. What was missing was a baseline. Meaning, a steady normal the closer sets on purpose and comes back to every time life lands a punch. The way I kept mine was journaling. In my best sales job ever, closing 5 to 10 deals a day, I journaled up to 6 times a day, almost after every single sales call. I'd write down every negative story running through my head that I wanted gone. Then I'd write a positive, grateful reframe for everything that happened on that call. I call it “mental gardening” You garden your thinking every day and pluck the weeds before they spread to your calls. Because if your closer can't change their own mind, they're not going to be able to change a prospect's mind.

How to find what killed your sales call in ~10 minutes: 1. Start at the END and watch the close first. 2. Jump to the first 5 minutes and listen for tonality and frame: does the prospect believe the seller, and who holds the higher status in the prospect's head? 3. Run the question check. Is the seller asking the right questions, in the right order, at the right time? 4. Run the precision check. Is the seller letting the prospect get away with vague, hand-wavy answers? That's poor discovery discipline, and it almost always kills the deal. 5. Watch the presentation LAST. The pitch goes last because it's almost NEVER the problem. 90%+ of the time, the problem is in discovery. Bookmark this for your next sales call review.

At LendingClub, I ran 4 business units handling 1.4M customer interactions a month. By everyone else's standards I was doing great. I was spiritually dead inside. Before that, I'd built LendingClub's sales team from 5 sellers to 150 sellers. I did it twice, in two different geographies, two different labor pools. When COVID hit, the company went into downsizing and panic, and shut down the entire Sales team. I agreed to become Director for all of Customer Success instead. The job was huge. But it took me away from my first love: the combination of coaching + sales. That's where the dead-inside feeling came from. It also taught me the lesson I still carry: Leaders still need to pour their all into their team members, to mentor and coach them to brilliance. AI can't and won't replace that. So I went out on my own. Now I help small and medium businesses grow and scale their own sales teams, with a coaching, customer-service-centric approach. That company is Cadence. We've built an always-on sales coach that guides salespeople in the moment, when a deal can still be won, rather than after the fact. That typically means a 50-100% increase in conversion rate, on the same ad spend. It's enabled by AI, but it's not a cookie cutter AI solution. We actually listen to the calls ourselves. The mission is the one that started my career: Coaching salespeople to success, with tireless focus on what they actually need in order to learn, and thrive. So much more to come...

Experienced salespeople are the RISKIEST hires you can make. My top 5 hires ever had never held a sales job. (This includes the woman who closed $380k in a single day and the guy who closed over 80% for 14 months straight) Most owners hiring closers want the opposite. They think: "Get someone with 10 years in the game, and they'll hit the ground running." That's actually backwards. If I look at the top 5 salespeople I've ever hired, 3 of them came from about as far outside sales as you can get. One was headhunted out of customer service. Another did multimedia and owned 500 pairs of sneakers. The third had only played semi-pro sports before coming to me. None of the 5 had held a sales job before, and none of them even WANTED one. Selling was never their goal (the customer service hire went on to work undercover as a vice cop after her time in sales). Now flip that around and look at my top 10 WORST salespeople of the last 12 years... every one of them had been in the game for 10, 20, even 30 years. Some had sat in the same role for a full decade. They couldn't: 1. take feedback 2. keep their emotions under control 3. learn to change or grow from their peers who were “less experienced” than them Consequently their results and earnings were wildly inconsistent. That's what a long enough career in sales will do to a lot of people. They get jaded, and the mind locks into place like cement. If they had even a little success, they're convinced they can sell every product under the sun. So when you hire one, you essentially inherit a cup that's already full. Nothing new goes in, plus the bad habits they built over decades, spill over to the rest of your team. And you pay extra for an inflated sense of self-worth, with salary requirements that ballooned to match. TL;DR: The best salespeople are not salespeople. If you’re hiring reps: > I advise you look in the most unlikely places for talent instead. > Hire people with NO sales background > Screen them for EXCELLENT communication skills, and are fun to talk to > Train them to sell exactly the way you want them to sell. It's easier and it's cheaper and you will make loads of money this way.