Ever wonder what it’d be like to square off against the sharks? Tanya VanCourt from Goalsetter.co just did that and we’ll share the exciting story from start to finish on today’s show. Whether you’re a fan of Shark Tank, Goalsetter, FinTech, or just entrepreneurship in general, you’re going to love our blow-by-blow telling of Tanya’s Shark Tank adventure. She shares LOTS of strategic lessons for anyone hoping to be a business owner, networker, or strategist.

Plus, in our headlines segment, we’ll talk to Peter Polson (CEO of Tiller) about Apple’s new credit card offering, which was announced just last week. While it’s been getting a lot of hype from the media, is the card worth it? We’ll break down the features of the new card, perceived benefits from it, and how this offering stacks up against others.

Also, we’ll dive into one piece from Barrons that could throw a big wrench in a few retirement plans. Are you counting on your primary residence to finance your retirement? We’ll discuss why that may not be the best strategy for your golden years. The Barron’s piece calls it a trap, but do we agree?

Later on, we’ll throw out the Haven Life Line to Les, who owes extra tax this year due to his 1099 income. Les also receives a W2 from his employer. Could he request extra withholding from his employer to cover his self employment taxes? We’ll round out the show with a letter from Nathan, who’s hopping jobs. Both of his employers have a 457 plan, but his new job won’t have a company match. What should he do with his 457? Roll it over? Leave it alone? Roll it to a different plan?

As always, we’ll still save some time for Doug’s trivia…which today is exceptionally epic.

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<4:11> Headlines

• If You’re Counting on Your House to Finance Your Retirement, You May Be Walking Into a Trap (Barrons)
• A big thanks to Peter Polson for taking the time to talk to us about Apple’s new credit card. You can find more from Peter at his company’s site, TillerHQ.com.
  • You can read up on Apple’s new card over at Time: The ‘Apple Card’ Is Apple’s New Credit Card. Is It Right for You?

<22:00> Tanya VanCourt

You can find more from Tanya at her site: Goalsetter.co

Keep up to date with Goalsetter on Twitter: @GoalsetterCo

Want to check out Tanya’s original appearance on Stacking Benjamins? Click here!

<57:16> Doug’s Trivia

• Martin Luther King Jr. made his famous mountaintop speech on today’s date in what year?

<1:04:40> Haven Life Line

• Les will owe additional taxes beyond his W2 due to 1099 income. He expects his extra income to be about the same next year. Could he ask his employer to withhold extra income to cover his 1099 taxes?

<1:12:08> Letter

During out letter’s segment we’ll tear open a letter from Nathan, who’s wondering what he should do with his 457 plan. You can read his letter below:

I have a 457 plan through work. It’s approx 70/30 Traditional/Roth. I’m leaving soon for another job with a 457 but no match. Do I:
1) Leave it where it’s at?
2) Transfer to my new job’s plan even though there’s no match?
3) Transfer to my TSP even though my TSP is all Roth currently?
4) Transfer to a traditional IRA and convert into my current Roth? My wife will only work half this year and we’re having our 2nd kid. I believe I’ll be able to cover the necessary taxes.

We’re only 32 and are fairly aggressive with our retirement savings (roughly 25% of our income).

Join us Wednesday!