Ryan Bakke turns to discuss the power of smart business acquisitions and tax strategy to skyrocket returns and keep more money in your pocket!

Ryan starts by reminding us the tax benefits of short-term rentals and real estate professional status. He explains the process of buying businesses including defining a buy box, identifying opportunities, and improving operations upon acquisition. He dives deep on lessons learned from operating businesses and tips on how to improve efficiencies through off-shore staffing. The show closes with great insights on assessing return on equity and investment to ensure your capital is working as hard as possible.

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Guests: Ryan Bakke, Tax Strategy 365

Link: SUCI Ep 244 - Ryan Bakke

Link: Ryan's Instagram

Link: Influence (Book Recommendation)

Link: SUCI Investor Meetups Page

Guest Questions:

01:24 Housing Provider Tip - Understand the maintenance and life span of hot water heaters.

03:34 Intro to our guest, Ryan Bakke!

06:42 Leveraging short-term rentals for tax benefits.

11:26 Efficiently delegating to grow your business.

22:37 How to hire off-shore employees.

28:32 The process of buying a business.

32:03 Defining a "buy box" for a business.

39:07 Lessons learned from buying businesses.

46:08 Ryan's take on ROI and Chicago's future!

53:28 What is your competitive advantage?

53:37 One piece of advice for new investors.

53:46 What do you do for fun?

53:59 Good book, podcast, or self development activity that you would recommend?

54:17 Local Network Recommendation?

54:35 How can the listeners learn more about you and provide value to you?

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Production House: Flint Stone Media

Copyright of Straight Up Chicago Investor 2026.

Episode 444: Leveraging Tax Strategy to Boost ROI with Ryan Bakke

Straight Up Chicago Investor

Episode 444: Leveraging Tax Strategy to Boost ROI with Ryan Bakke