How to Scale Your Business WithOUT Ads with Dr. Connor Robertson

Host Liam Leonard brings Dr. Connor Robertson, retired chiropractic doctor and now owner of tech business, in today’s conversation on the Prosperity Perspective Podcast. Connor’s expertise in how to optimize the cash you could be spending instead of using it to pay taxes is staggering.

Take a serious look with them at the benefit of eliminating all tax liability, where Connor finds the highest returns from his investments, and why you may need to stop going to school if it’s not supporting your long-term goals as an entrepreneur. They will also spend time breaking down why you should look at IULs, making the wiser choice to invest cash from your insurance and replenish those funds.

3 Key Takeaways:

  • Why starting with taxes for your investments will set you up for long term income.

  • The 3 crucial steps of research Connor makes before deciding where to invest his money.

  • Why Connor’s first go-to strategy is depreciation.

Show Notes:

[0:26] Connor introduces himself

  • His first experience going to a chiropractor after a spine injury

  • Going to Chiropractic school


[1:54] Going from Chiropractic to tech

  • His parents’ influence

  • LinkedIn

  • Hiring people to do what he can’t and then learning how they do it

[4:11] Watching someone else and learning from him

  • Raising the price 7 times over 10 months

[5:30] Once he’s become an accredited investor, where Connor puts his money

  • Taxes as #1

  • Deploying the bonds saved from taxes

  • Hitting pause on his unsuccessful investments

  • Cash-value life insurance policies

[9:00] “Storing the cash:” looking for return in the long or short term?

  • Transitioning from an S-Corp to a C-Corp

  • What does the liquidity look like?

  • If I borrow it and I put it back, does it still grow? - Dr. Connor Robertson

[10:33] Evolving from tax to insurance, to his new IUL approach

  • Looking at Airbnb as means to borrow from his insurance

  • “I think the long-term strategy, to be honest with you, is to leverage the shareholder loans.”-Connor Robertson

  • “My first strategy is depreciation. Buy the real estate to get the depreciation, whatever’s left goes into the insurance policy...I actually do it the opposite way.”-Connor Robertson

[13:35] What Connor would have done differently earlier on

  • Go to school

  • Don’t take bad debt (like student loans)

  • “Now the strategy is: look at how much income we’re going to make each year on the personal side through the business, and figure out: ‘what do I need to buy to make that income equal zero?’”-Connor Robertson

  • Real estate, executive bonus plans/insurance, or lending money

  • DON’T pay yourself W2 income

[17:00] The sort of returns Connor is looking for from his investments

  • Why if there is a depreciation factor, he’s willing to take zero percent on it

  • Finding a healthy cash flow cap

  • “At the end of the day, where else are you going to get a 40% return right now? Because that’s what you get by saving tax...That’s a pretty good return this year.”-Connor Robertson

[20:29] It's all about income shift: most of the time the issue is spending, not making

[21:20] When Connor decided that he knew enough from school to go do research on his own

  • The “silent killer” of sitting on a lot of student loan debt

  • “The time to stop is when you’re willing to jump...When you’re just willing to not have to go to school.”-Connor Robertson

  • Don’t waste your time trying to please other people

[23:20] The most exciting thing Connor is doing today

  • Crypto currency and 105 USD sell opportunity with bitcoin

About Dr. Connor Robertson:

Connor Robertson began his business journey in a place you wouldn’t expect: by going to the chiropractor after years of spinal pain that originated from an accident. Connor decided that the relief he felt was worth spreading, obtaining his doctorate as a chiropractor, funded by his family.

But Connor soon realized that his interests didn’t lie in chiropractic, deciding to turn a total 180 degrees and invest in a tech company, which is now a fully grown, multi-service business. Connor also used research along with trial and error to become nothing short of an expert on how to handle tax rules the right way. Now, Connor is also host of his own podcast where he shares his knowledge with clients and friends alike from his booming tech experience.

Connect with Dr. Connor Robertson:


Google his name for all of his social platforms

Connect with The Prosperity Perspective Podcast:




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