I wrote previously about when I first started selling podcast ads. I’d like to start with a little more color on how that happened: I started cohosting a show called Unprofessional. We were on a then-nascent, now nonexistent, podcast network called Mule Radio. For a few episodes, we just did the show and that was it.

After several weeks like that, Mule sent us an ad to read. That was cool: Now we’d get paid to do the show. Fun! They sent ads every week for several weeks. Then one week… there was no ad.

That was no fun. Now that I was getting paid to make episodes of the show, it was far less interesting to make an episode and NOT get paid.

So I asked Mule if they’d mind if I tried selling ads for the show. Of course they didn’t mind. Also, I had absolutely no sales experience of any kind.

But it turned out that I was good at selling ads for the podcast. Good enough that my pal Glenn asked me to sell ads for his podcast. And then Mule said, why don’t you just start selling ads for all of Mule? And then Marco asked me to sell Accidental Tech Podcast and Gruber had me start telling The Talk Show and friends of friends started reaching out… Three months after I sold my first podcast ad, I was repping 50 shows.

My first year of selling podcast ads, my gross ad sales revenue was $500,000.

Even so, when I was debating whether I wanted to go “full time” with podcast ad sales — I had been limited to nights and weekends with a separate day job in year one — I was nervous. I didn’t want to be a full-time salesperson.

I thought of a used car salesperson. Slimy, sneaky, say anything to get the deal done. That was sales to me. I didn’t want to be that guy.

But then I realized: I’m not that guy. So I won’t be that guy.

I was really freaking good at selling podcast ads. There were three primary reasons:

1. I was transparent and honest.

2. I was extremely disciplined about follow-up.

3. I was communicative.

And really, that’s it. That’s what made me good at it. It helped that podcast ads really work, and that I had great shows to sell against.

I realized that those skills — open conversations, strategically pairing advertisers with shows, executing at a high level with success — they really all speak directly to entrepreneurship. Working with customers, getting them to grow spends with you, building out successful strategies for success… That’s building a business. That’s growing a company.

So I reframed my mindset: I was an entrepreneur flexing my sales muscle. That’s different.

I should add that there’s nothing intrinsically wrong with sales, and some of my concerns about being a seller were a bit misplaced. That said, the negative connotations I associated with salespeople weren’t unique to me. The sleazy salesperson is a common trope, and many folks on the buy side approach people on the sales side warily because of it.

Your job as a seller is to convince people from the outset, with everything you do, that you’re not one of those sellers. That you’re a human.

And if you got this far and you’re thinking to yourself, that’s nice, but it maybe doesn’t apply to me so much, because I’m not IN sales, let’s correct that.

If you ever deal with customers or potential customers, in any way — you’re in sales. More on that soon.