"The most fun I've had on a podcast - I'm still smiling days later. Thanks so much for having me on!"
- Elizabeth R.
"I say no to just about every podcast offer I get, but I'll say yes to come back on this for a second time with you, Jack."
- Andy B.
"This was so much fun and we seamlessly went from funny stories to actual business topics - it was perfect!"
- Shay P.
About the Show
This isn’t your typical business podcast.
It’s a business-and-comedy crossover where we talk entrepreneurship, make jokes, and actually enjoy the conversation. We start with where you came from, dig into the early (often messy) days, and unpack how your personality shows up in your business today.
Are you scrappy or sophisticated? Completely improvised or strategically engineered?
Along the way, we pull random questions, laugh at corporate nonsense, and share some expertise. No fluff, no canned answers, just fun, genuine conversation.
Because people listen more when you’re having fun.
And people do business with people they actually like.
About the Host
Jack Tompkins is a data nerd. Absolutely.
But he also genuinely enjoys talking with people - the very rare extroverted data nerd.
Jack has been running Pineapple Consulting Firm since 2020. He's served hundreds of clients, and has done tons of speaking events, podcasts, conferences, etc. - all of them about adding value to the listeners' business through data.
In Scrappy but Successful, though, Jack makes the conversation incredibly fun and let's the guest's personality shine through.
If you're lucky enough to be a guest on the show, show up with a smile, sit back, and enjoy the fun journey through your early life and early business days so the viewers can get to know like and trust you before they even meet you!
Listen wherever you get your podcasts
Our Latest Episodes
Interested in being a guest?
Reach out to Support@PineappleCF.com and see if it makes sense to have you on!