The path of a wealthy real estate investor is never a straight line. Often we’ll <a href="https://www.biggerpockets.com/blog/reach-goals-intentional-life" rel="noopener noreferrer" target="_blank">set up goals</a> we deem worth chasing, then somewhere along the way, we’ll pivot to a more refined goal. Without knowing where we want to go, we can’t get the proper footing to start the journey. This is exactly what snowboarder, skater, real estate investor, and lender, <a href="https://www.chrisnaugle.com/" rel="noopener noreferrer" target="_blank">Chris Naugle</a>, talks about with us today.Chris grew up in chilly Buffalo, New York and knew he wasn’t the employment type of guy. So, after quitting his first job, he decided to start a clothing company in his basement. Then, with some of the profits from his clothing venture, paired with a loan from his mom’s <a href="https://www.biggerpockets.com/blog/glossary/heloc" rel="noopener noreferrer" target="_blank">equity line</a>, he opened up a skateboard shop. Everything was going well, until the dot com crash, prompting him to become an advisor on Wall Street.As an advisor, Chris found that more and more of his wealthy clients were investing in real estate. This prompted him to take the leap and start flipping, buying <a href="https://www.biggerpockets.com/blog/overlooked-commercial-investments-real-estate" rel="noopener noreferrer" target="_blank">commercial real estate</a>, and investing in rentals. But, Chris wasn’t borrowing the right way, leading him to have to get rid of his 37 unit portfolio or <a href="https://www.biggerpockets.com/blog/7-tips-overcome-bankruptcybuild-lasting-wealth" rel="noopener noreferrer" target="_blank">go bankrupt</a>.After losing years' worth of work and a massive amount of equity, Chris started to draw up systems and procedures that could work as a safety net for his investments. Now with a smaller portfolio of around 23 units, he works mostly as the bank that lends other investors their money. All of this was made possible when Chris stopped and thought about what his “perfect day” was and what he needed to do to make it a reality.In This Episode We Cover:Using flipping as an entry point to get into real estate investingBuying commercial buildings like strip mallsKeeping your <a href="https://www.biggerpockets.com/blog/glossary/debt-to-income-ratio-dti" rel="noopener noreferrer" target="_blank">debt-to-income (DTI)</a> low so you can keep borrowingConventional financing vs. <a href="https://www.biggerpockets.com/blog/real-estate-commercial-loan-approval-simple-steps" rel="noopener noreferrer" target="_blank">commercial financing</a> for real estate investingThe “rules of engagement” when it comes to investingTrading money for money instead of time for moneyKnowing what your “perfect day” isAnd SO much more!Links from the Show<a href="https://www.biggerpockets.com/forums" rel="noopener noreferrer" target="_blank">BiggerPockets Forums</a><a href="https://www.youtube.com/biggerpockets" rel="noopener noreferrer" target="_blank">BiggerPockets Youtube Channel</a><a href="https://www.biggerpockets.com/membership-types" rel="noopener noreferrer" target="_blank">BiggerPockets Membership</a><a href="https://www.hgtv.com/shows/risky-builders" rel="noopener noreferrer" target="_blank">HGTV's Risky Builders</a><a href="https://www.eharmony.com/" rel="noopener noreferrer" target="_blank">Eharmony</a><a href="https://www.biggerpockets.com/blog/biggerpockets-podcast-477-ryron-gracie" rel="noopener noreferrer" target="_blank">BiggerPockets Podcast 477: Discomfort &amp; Uncertainty Lead To Victory with BJJ Black Belt Ryron Gracie</a><a href="https://www.biggerpockets.com/blog/biggerpockets-podcast-471-tim-grover" rel="noopener noreferrer" target="_blank">BiggerPockets Podcast 471: What Michael Jordan and Kobe Taught Tim Grover about “Winning”</a>Check the full show notes here: https://www.biggerpockets.com/show478

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478: From Pro Snowboarder to Full-Time Flipper & Investor w/ Chris Naugle

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