I Never Took a Sales Course. Here's How I Learned to Sell Anyway.

Nobody hands you a sales playbook when you go out on your own. You figure it out the hard way - through rejection, awkward pitches, and the slow, humbling realization that everything you thought you knew about selling was wrong.

That's how it went for me. And looking back, I'm actually grateful for it.

Here's the story of how I unknowingly learned to sell by making every mistake in the book - and what I took away from each one.

Mistake #1: Making It All About Me

When I was two years into my role at Uber, I launched Uber Eats in Miami. It went well. Really well. So when the GM opportunity came up, I threw my hat in the ring. I was 26, I knew my resume was thin, but I told them not to disqualify me on that basis alone. Long story short - they did anyway, because I didn't have an MBA.

Frustrated but not done, I pivoted. I started approaching GMs of smaller markets - Raleigh, Charlotte, Nashville - essentially asking to run their cities. And I got rejected, again and again and again.

I was confused. Great track record. Recent promotion. Successful launch under my belt. What was the problem?

The problem was me. Or rather, my pitch - which was entirely about me. I want this. I deserve this. I've earned this.

Here's the thing: nobody cares about what you want. Not really. Your company cares about its goals. Its outcomes. Its problems. And when you lead with your own needs, you've already lost.

Once I figured that out, everything changed.

Lesson #1: Lead With Their Problem, Not Yours

I took a step back and looked at what Uber actually needed at that moment. In 2016, the company was in a race to launch Uber Eats markets all over the world - and I was one of very few people inside the company with actual launch experience. That was the card I had to play.

So I reframed my entire approach. Instead of I want to be a GM, it became you need to launch fast, I've done this before, let me help you.

I got a call. They told me to pack my bags and get on a plane to Amsterdam. They'd figure out the title later.

That's the difference between pitching your resume and solving someone's problem. One gets you politely ignored. The other gets you on a flight to Europe.

The First Real Client: Selling By Not Selling

A couple years later, I left Uber. I wasn't sure what I wanted to build yet, so I decided to just see what happened if I put my name out there as a consultant. I reached out to 12 companies. Eleven either ignored me or passed.

One said yes.

It was a Series A self-driving startup that wanted to build a food delivery marketplace - and their next round of funding basically depended on it going well. They had no one with that experience. I had done it. Perfectly aligned.

I put together a proposal - a full PowerPoint deck with a business plan, a growth model, a framework for how I'd think through the major decisions. I didn't give them all the answers, but I showed them exactly how I'd get there.

And I asked for $25K a month, part-time.

They said yes. Without negotiating.

I was floored. But here's why it worked: I wasn't selling them anything. I was showing them that I could solve a problem they already had, with stakes they were already feeling. Paying me $25K a month was a rounding error compared to what was on the line for their Series B.

It never felt like a sales pitch because it wasn't one. It was you have a problem, I can solve it, here's the proof.

The Value of Asking Good Questions

One thing I learned early - especially on the phone with a potential client - is that asking the right questions is itself a form of giving value.

When I was consulting in the freight space, I'd often ask something like: How do you plan to scale your marketplace without just throwing more headcount at the problem?

That question alone would stop people in their tracks. For decades, freight companies had grown by hiring more people. Nobody had really pushed them to think about what technology could replace. By asking the question, I was getting them to think differently - and at the same time, establishing that I had the expertise to think that way in the first place.

You don't need to have all the answers in a sales conversation. Sometimes the right question is worth more than a polished pitch deck.

Give, Give, Give - Then Ask

Here's the framework I've landed on after years of doing this: 90% of what I put out into the world is pure value. No pitch. No agenda. Just teaching, sharing, and being genuinely useful.

That's what content does, by the way. When I post on LinkedIn or put out an episode like this one, I'm essentially sending that Series A proposal to a thousand people at once. They're learning. They're evaluating whether I know what I'm talking about. And they're making their own decisions - all without me having to get on a call with each of them.

Could someone take my content, learn everything I share, and go execute it themselves? Sure. But here's the bet I'm making: most people won't. They'll still want the software, the system, the execution support. Because knowing what to do and actually doing it consistently are two very different things.

The 10% of the time when I do ask for something - an email, a call, a signup - I try to make sure the ask still has value baked in. A free LinkedIn strategy session. A lead magnet. A newsletter worth reading. If you're going to ask for someone's time or attention, make it worth their while.

The Takeaway

Here's the one thing I want you to walk away with:

Stop selling. Start solving.

Figure out the specific problem your buyer is sitting with right now. Show them you've seen it before and you know how to get through it. Give generously - through content, through questions, through your time - without keeping score.

The sale becomes almost incidental when you do it right.

If you want to put this into practice on LinkedIn - attracting clients by showing up as the credible expert you already are - come check out what we're building at mylance.co. We have a free version, and our customers are showing up authentically and filling their pipelines. It's the real deal.

Go check it out. And if this resonated, share it with a founder who needs to hear it.

Mylance

This article was written by Mylance, the LinkedIn content system built for founders and experts who want consistent, high-quality posts that attract clients. We help you lock in your positioning, clarify your ideal customer, and build a content strategy that actually resonates. Then our system gives you a content calendar, drafts posts in your authentic voice, and keeps you accountable - so you stay visible and attract the right clients while saving hours each week!If you’re ready to grow your presence and pipeline on LinkedIn, sign up at Mylance.co.