Episode 244: Real Estate Tax Advantages, Short-Term Rentals, and Branding, With Ryan Bakke


Ryan Bakke is a CPA, real estate investor, and coach who is helping others build wealth via real estate and tax strategy!

Ryan starts by explaining the value a Tax Strategist brings and common mistakes on tax returns. He dives into the power of short-term rentals (STRs), their tax advantages, and how to underwrite STR investments. Ryan shares his philosophy and tips for building a client base and following that have led him to a thriving business! Throughout the show, Ryan hammers home the importance of being a go-giver and delegating tasks to best use your time!

If you enjoy today’s episode, please leave us a review and share with someone who may also find value in this content!

02:56 Housing Provider Tip: Be ready to recognize and act on a good deal!

04:58 Intro to our guest, Ryan Bakke!

05:29 Tax Preparer vs. Tax Strategist

09:14 Common Tax Returns Mistakes.

10:35 Tax Insights on Short-Term Rentals (STRs)!

17:27 Short-Term Rentals in Chicagoland.

19:21 Automating STRs!

24:58 Underwriting STRs!

31:06 Ryan’s approach to building a following!

46:29 Ryan’s next 5 years!

50:34 What is Ryan’s competitive advantage?

51:16 One piece of advice for new investors.

52:34 What do you do for fun?

53:18 Good book, podcast, or self development activity that you would recommend?

54:20 Local Network Recommendation?

54:55 How can the listeners learn more about you and provide value to you?


Connect with Mark and Tom: StraightUpChicagoInvestor.com

Email the Show: StraightUpChicagoInvestor@gmail.com

Guest Name: Ryan Bakke

Guest Company: 

Guest Link: https://linktr.ee/LearnLikeaCPA

Other Links for show notes:

The LearnLikeaCPA Show

$100M Offers (Book Recommendation)

The Game (Podcast Recommendation)

Muscle for Life Podcast

Show Sponsors: 


Build Your Team


Have a question, want to be a guest on the podcast, or looking for sponsorship opportunities?

Complete the form below and we will get right back with you.