The Pickle Podcast - A While Running Podcast
Sep 27, 2026 · 46 min · 9 segments
Renowned Keynote Speaker and life long runner Jack Wilson comes to discover Sioux Falls and shares a life of running and business adventures. From riding the short bus to driving the big bus, Jack…
And, you know, it was the first time I actually, I think I was getting paid $65,000.
Which was a tremendous amount of
sure.
And you had to make it through the intern program, and then you would be assigned your own territory.
So the next 10 years, I was in and out of sales jobs, kind of honing that craft.
So I got paired with a guy that the closest analogy would be Rodney Dangerfield from Caddyshack.
And afterwards, sitting there having a beer, And he said, you know, what do you do? I told him I was a sales guy, you know, number one sales guy in the software company.
And he said, man, he said, I am starting an online chat company and I literally just paid a recruiter $30,000 to find my VP of sales.
He said, I would love for you to come to my office next week and let me show you what I've got going on.
And he showed me this massive office where there were five people working on saw horses with doors across them.
And, you know, it was the first time I actually, I think I was getting paid $65,000.
Which was a tremendous amount of
sure.
And you had to make it through the intern program, and then you would be assigned your own territory.
So the next 10 years, I was in and out of sales jobs, kind of honing that craft.
So I got paired with a guy that the closest analogy would be Rodney Dangerfield from Caddyshack.
And afterwards, sitting there having a beer, And he said, you know, what do you do? I told him I was a sales guy, you know, number one sales guy in the software company.
And he said, man, he said, I am starting an online chat company and I literally just paid a recruiter $30,000 to find my VP of sales.
He said, I would love for you to come to my office next week and let me show you what I've got going on.
And he showed me this massive office where there were five people working on saw horses with doors across them.
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