how i lost a $25k deal this month

$25k at my fingertips and I lost it. Oof.

Here’s how it happened:

One of the biggest real estate developers in the world, Ryan Serhant wrote a book titled Sell it like Serhant back in 2018.

After selling millions of copies, he and his team turned the book into a digital course.

Both the book and course show real estate brokers the exact system Ryan used to build one of the most successful real estate portfolios we’ve ever seen.

(For context, he has a $250M NYC penthouse listing right now. He’s at the very top of the game)

Because the book and course struck a huge cord with consumers, the team decided it was time to package “Sell it like Serhant” as a B2B sales training program for local brokerages all over the US.

One problem: they don’t have an outbound sales function.

Even though Ryan’s personal brand (2M+ followers) generates tons of leads, they still needed an outbound SDR org to amp things up.

And three weeks ago, I found myself in the running to build the whole thing from scratch.

How?

From a single Linkedin post with less than 30 “likes” (your friendly reminder to hit the damn publish button - you don’t need a big audience, just the right one)

After publishing the post I began exchanging messages with the VP of Sales at Serhant about SDRs, future of sales, hiring practices, etc.

This led to a phone call with no expectations and no angles, purely networking and brainstorming.

For 30-45 minutes of conversation, I simply listened and asked questions - it was clear he had a lot on his mind and needed someone to help him make sense of his thoughts. Not sure about you, but I can relate to this big time.

After learning about where he was versus where he wanted to be, offering a helping hand was a frictionless next step.

Why?

Because I knew for a 100% certainty I could add a ton of value to him and his team quickly.

It’s easy to ask for the sale when you know you can knock it out of the park.

I suggested the VP let me build out the SDR org over 3 months - everything from cold call/email frameworks and discovery best practices to CRM setup and leaderboard reporting - even hiring/training their first couple of SDRs and building out the playbook.

The price tag for this service was $25k and personally, he was sold immediately.

After running it up the food chain, it was time to speak with his President. Not Ryan Serhant, but the guy who reports to Ryan.

The President of Serhant Ventures put 15 minutes on my calendar and when the day came, he was 5 minutes late. Now I have 10 minutes to convince a former NBC executive to cough up $25k to someone he has no familiarity with.

So, what do I do with my 10 minutes? With such limited time, do I go for the hard sell or do I follow my tried-an-true strategy of asking great questions?

I went with option #2 - discovery always feels like the better way for me to sell.

Turns out, that was the wrong strategy.

Ultimately, we had a great conversation - in fact he pushed his next meeting and stayed on an extra 10 minutes - which was a great sign from both a personal connection and business standpoint.

But, I lost the deal for two reasons:

1. My offer was more expensive than my competitor and I was unwilling to budge. More on this below.

2. My competition had a longstanding relationship with the President. Always tough to beat out, even if you’re the more valuable resource.

Here’s the response I received from my original contact about the decision:

“Hey Cooper - actually just spoke with (will remain nameless) last night.

He decided he wanted to move forward with the other consultant because we have an existing relationship and she will bill us hourly.

At the end of the day, it was his decision and I pushed quite hard to bring you in.

I see a scenario where we may be looking to explore some of your training/onboarding at some point, but for now we are going to move forward with her.”

Thanks for all of your hard work on this and really sorry this is how it worked out… I truly thought it was a no-brainer to use you… but the relationship with her and inexpensive component really mattered to (nameless).”

Of course it’s a bit painful to lose a deal, especially with a company that has such a strong brand name - would’ve been great for social proof/authority. But here’s why it works…

Why It Works (for my growth)

I walked away with a few strong connections, a gauntlet of real-time sales training, and this great reminder:

Even when the person who will be directly impacted the most by your product/service wants to hire you, they are not necessarily the decision maker.

The two loss reasons I listed above are my own rationalization on why I lost the deal, but here’s why I really lost:

I didn’t focus enough on driving value (aka pitching) during my final conversation.

Bottom line is - he thought I was too expensive, which isn’t the case. Their average deal size is $30k and my proposal was $25k. If what I build for them closes even one deal, my project pays for itself.

My offer wasn’t too expensive, he just didn’t hear enough about the outcomes my project would produce in for his business.

Yes, I found myself in this position not because I had an immaculate sales pitch, but because I spent 45 minutes asking the VP thoughtful and informed questions.

But to drive this deal home I needed to shift from “discovery sales” to “here’s why you need me to do this project.”

Lessons learned:

1. Content Creation is the best form of outbound - you’re getting your voice in front of prospects and positioning yourself as the expert. This is the way. Start attracting, stop chasing.

2. Every sale is very different - even though most principles and frameworks apply everywhere, you have to continuously fine tune when to pull certain levers. For example, the company I work for has a 18 month sales cycle. You don’t turn on the “pitch” for several months because it takes that long to learn enough to deliver an informed pitch. With this Serhant opportunity, I should’ve gone for the hard sell earlier. It was a much shorter sales cycle with a small buying committee (2-3 people).

3. Push yourself out of your comfort zone - I mentioned earlier that discovery feels like the most natural way for me to sell. Asking informed questions that indicate the type of solution you provide is a bullet proof and sustainable way to find success in enterprise sales with 10-12 person buying committees. Not so much in a compressed sales cycle - delivering an immaculate “why me” sales pitch would’ve done the trick here.

4. Don’t budge on price - unless the opportunity at-hand will change your life forever, don’t budge. Yes, I lost the deal. I also set expectations in the event they want to work together in the future. And I made a strong connection with a few executives that know I won’t devalue my work. Which is something they respect and relate to.

And that’s how I recently lost a $25k deal.

The experience, takeaways and lessons learned were extremely valuable.

If I would’ve done anything differently, I would’ve had a few slides ready that visualized the value (in dollars) I could’ve created for their business.

Take your licks as they come and execute accordingly in the future.

That’s all for today, Happy 4th!

Next weeks issue: How to make content your outbound strategy

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