

Elevate with Tyler Chesser - The Real Estate Podcast for Investing, Mindset and Personal Development
Tyler Chesser
Mindset, mind expansion and personal development for high-performing real estate investors. Join Tyler Chesser, a successful real estate entrepreneur and personal growth thought leader, as he sits down for mind expanding conversations with influential authorities in real estate, as well as top experts in other industries and disciplines. In these discussions, Tyler distills the mindset, habits, routines and tactics from the experts which will support you in your own quest to Elevate to a life without limits.
Episodes
Mentioned books

Nov 3, 2020 • 1h 1min
E101 - The Art of Possibility with Gary Beasley
Gary Beasley is CEO of Roofstock, a leading real estate investment marketplace which he co-founded in 2015. Gary has spent most of his career building businesses in the real estate, hospitality and tech sectors. Gary was instrumental in acquiring and integrating more than $800 million of resort properties for KSL Resorts, and spent five years as CFO of online brokerage pioneer ZipRealty.
Gary also served as CEO of Joie de Vivre Hospitality, then the second largest boutique hotel management company in the country. Immediately before starting Roofstock, Gary led one of the largest single-family rental platforms in the U.S. through its IPO as co-CEO of Starwood Waypoint Residential Trust, now part of Invitation Homes.
In this episode, Tyler and Gary’s discussion focused on the mindsets and traits required to fulfill seemingly impossible dreams. They discussed Gary’s motivation to prove naysayers wrong, the moment he decided to forge his own path, celebrating failure, traits necessary for innovation, different types of leadership styles, active versus passive listening and intellectual curiosity.
They also discussed how Gary’s previous experiences were applied to his innovative real estate investing and technology business, the characteristics it takes to be a successful entrepreneur, how to deal with stress and more!
Connect with Gary:
Website: http://www.roofstock.com
The following books were mentioned in the show:
Unbroken, by Laura Hillenbrand
Entrepreneurial Leadership, by Joel Peterson
Guns, Germs and Steel, by Jared Diamond
Apply for coaching with Tyler! The world's top performers in any field have a coach to help them achieve drastically greater results and in less time. The most successful real estate investors are no different. To apply for a results coaching session with Tyler, visit coachwithtyler.com.
This episode of Elevate is brought to you by CF Capital LLC, a national real estate investment firm that focuses on acquiring and operating multifamily assets that provide stable cash flow, capital appreciation, and a margin of safety. CF Capital leverages its expertise in acquisitions and management to provide investors with superior risk-adjusted returns while placing a premium on preserving capital. Learn more at cfcapllc.com.

Oct 30, 2020 • 49min
E100 - Giving, Investing and Self-Awareness with Sterling White
With just under a decade of experience in the real estate industry, Sterling White currently manages over $10MM in capital, which is deployed across a $26MM real estate portfolio made up of multifamily apartments and single-family homes. Through the company he co-founded, Sonder Investment Group, he owns just under 500 units. Sterling has been contributing content to BiggerPockets since 2014, with over 200 posts on topics ranging from single-family investing and apartment investing to mindset and scaling a business online.
In this episode, Tyler and Sterling’s discussion focused on giving, investing and how self-awareness contributes to personal and professional growth. They talked about Sterling identifying and overcoming childhood and current-day limiting beliefs, the moment Sterling questioned his path in life, various ways Sterling invests in himself and giving without the expectation of receiving.
They also discussed the most important characteristics a salesperson should possess, selling outside of business, sterling’s direct-to-owner approach, building a real estate team, the multifamily deal failure that set him up for later success and more!
Connect with Sterling:
Website: https://www.sterlingwhiteofficial.com/
Instagram: https://www.instagram.com/sterlingwhiteofficial/
LinkedIn: https://www.linkedin.com/in/sterling-white-b8840763/
The following books were mentioned in the show:
The Four Agreements, by Don Miguel Ruiz
Shoe Dog, by Phil Knight
The Essence of Success, by Earl Nightingale
Sell or be Sold, by Grant Cardone
The Maverick Mindset, by Doug Hall
Apply for coaching with Tyler! The world's top performers in any field have a coach to help them achieve drastically greater results and in less time. The most successful real estate investors are no different. To apply for a results coaching session with Tyler, visit coachwithtyler.com.
This episode of Elevate is brought to you by CF Capital LLC, a national real estate investment firm that focuses on acquiring and operating multifamily assets that provide stable cash flow, capital appreciation, and a margin of safety. CF Capital leverages its expertise in acquisitions and management to provide investors with superior risk-adjusted returns while placing a premium on preserving capital. Learn more at cfcapllc.com.

Oct 27, 2020 • 58min
E99 - Lifestyle Design Through Passive Income & Personal Development with Maurice Philogene
Maurice Philogene is a senior executive, real estate investor, restaurant owner, explorer of 96 Countries, public servant (federal agent and police officer) and aspiring philanthropist. His passion is serving clients in the consulting space and acquiring multi-family properties to generate passive income and build legacy. His shift towards lifestyle design has started - living how, where and in what way we want to live - all while helping people along the way.
In this episode, Tyler and Maurice’s discussion focused on lifestyle design by generating passive income and committing to personal growth. They discussed creating freedom through time and mobility, being a minimalist, Maurice being a prisoner of his own success and how personal growth has evolved him as a person. They also went in-depth on Maurice living a lonely, unique entrepreneurial journey.
Other topics included how a 30-day trip in Paris transformed Maurice, the three things that fulfill his life, setting unattainable goals, the benefits of traveling, what Maurice identifies as “real wealth” and much more!
The following books were mentioned in the show:
Four Hour Work Week, by Tim Ferriss
Man’s Search for Meaning, by Viktor E. Frankl
Vagabonding, by Ralph Potts
Connect with Maurice:
LinkedIn: https://www.linkedin.com/in/mauricephilogene/
Instagram: https://www.instagram.com/mauricephilogene/?hl=en
website: https://www.thequattroway.com/maurice-philogene
Apply for coaching with Tyler! The world's top performers in any field have a coach to help them achieve drastically greater results and in less time. The most successful real estate investors are no different. To apply for a results coaching session with Tyler, visit coachwithtyler.com.
This episode of Elevate is brought to you by CF Capital LLC, a national real estate investment firm that focuses on acquiring and operating multifamily assets that provide stable cash flow, capital appreciation, and a margin of safety. CF Capital leverages its expertise in acquisitions and management to provide investors with superior risk-adjusted returns while placing a premium on preserving capital. Learn more at cfcapllc.com.

Oct 23, 2020 • 57min
E98 - Attaining Peak Performance in Real Estate Investing with Zachary Beach
Zachary Beach is an Amazon Best-Selling Author of The New Rules of Real Estate Investing and co-host of the Smart Real Estate Coach Podcast. He is a Partner, COO, and Coach at Smart Real Estate Coach. In September 2020, they’ll be releasing a revised edition of Real Estate On Your Terms, which Zach will be co-authoring.
At the age of 25, Zach decided to leave the world of bartending and personal training and jump into the family business. Zach has now completed over 100 deals and growing. On top of that, he coaches students around the country on how to buy and sell property just like his family does.
In this episode, Tyler and Zach’s discussion focused on attaining peak performance necessary for real estate investing and self-fulfillment. They discussed Zach’s key tactics for peak performance, mindsets needed for Zach’s transition from bartending and personal training to real estate, the three questions you should always ask yourself and several tips on how to get into a flow state.
Investing-specific topics included several team-building tips for solopreneurs, the relevance of buying real estate on terms, Zach’s consulting company’s vision to make 1500 transactions with its associates and much more!
Connect with Zach:
Website: smartrealestatecoach.com
Book Website: newrulesforfree.com
Youtube: https://www.youtube.com/user/smartrealestatecoach
LinkedIn: https://www.linkedin.com/in/zacharyrbeach/
The following books were mentioned in the show:
You Were Born Rich, by Bob Proctor
The Rise of Superman, by Steve Kotler
The Road Less Stupid, Keith J. Cunningham
The Trillion Dollar Coach, by Eric Schmidt
Apply for coaching with Tyler! The world's top performers in any field have a coach to help them achieve drastically greater results and in less time. The most successful real estate investors are no different. To apply for a results coaching session with Tyler, visit coachwithtyler.com.
This episode of Elevate is brought to you by CF Capital LLC, a national real estate investment firm that focuses on acquiring and operating multifamily assets that provide stable cash flow, capital appreciation, and a margin of safety. CF Capital leverages its expertise in acquisitions and management to provide investors with superior risk-adjusted returns while placing a premium on preserving capital. Learn more at cfcapllc.com.

Oct 20, 2020 • 1h 3min
E97 - Scaling the Mountain of Fulfillment with Bestselling Author and Performance Coach Jairek Robbins
Jairek Robbins is a bestselling author and performance coach. FastCompany calls him inspiring and says he’ll make your life less ordinary. Forbes says Jairek will teach you how to succeed. Deepak Chopra will advise you to go to Jairek to help create meaning and fulfillment in your life. Brian Tracy applauds Jairek’s ability to teach people how to develop meaning and purpose in life, and then to make a difference in the lives of others. Looking for ways to level up in life and business? Jairek is your guy.
In this episode, Tyler and Jairek’s discussion focused on how serving others can fill the three life buckets of “I am enough,” “I have enough,” and “I am loved enough.” Jairek illustrated the “two mountains” concept of consuming and being consumed, how consuming leads to a void, why certain behaviors are needed for fulfillment, the life event that inspired him, and how much of people’s time is actually spent in alignment with their top three values.
Other topics included looking into your own soul, the daily patterns that keep Jairek at his best and Jairek’s simple life philosophy. Be sure to check out the Youtube version of this inspiring, visual episode!
Watch here: https://www.youtube.com/watch?v=wwb6BpCch-I
Connect with Jairek:
Website: https://jairekrobbins.com/
Facebook: https://www.facebook.com/JairekRobbinsCompanies/
Twitter: https://twitter.com/jairekrobbins
Instagram: https://www.instagram.com/jairekrobbins/
The following book was mentioned in the show:
Second Mountain, by David Brooks
The Amazing Development of Men, Alison A. Armstrong
The Queen’s Code, by Alison A. Armstrong
Cool to be Kind
Apply for coaching with Tyler! The world's top performers in any field have a coach to help them achieve drastically greater results and in less time. The most successful real estate investors are no different. To apply for a results coaching session with Tyler, visit coachwithtyler.com.
This episode of Elevate is brought to you by CF Capital LLC, a national real estate investment firm that focuses on acquiring and operating multifamily assets that provide stable cash flow, capital appreciation, and a margin of safety. CF Capital leverages its expertise in acquisitions and management to provide investors with superior risk-adjusted returns while placing a premium on preserving capital. Learn more at cfcapllc.com.

Oct 16, 2020 • 1h 33min
E96 - Confident Decision-Making with Bestselling Author & Former Professional Poker Player Annie Duke
Annie Duke is an author, corporate speaker, and consultant in the decision-making space. Annie is the author of the newly released How to Decide: Simple Tools for Making Better Choices and Thinking in Bets, a national bestseller. As a former professional poker player, Annie won more than $4 million in tournament poker before retiring from the game in 2012. Prior to becoming a professional player, Annie was awarded a National Science Foundation Fellowship to study Cognitive Psychology at the University of Pennsylvania.
In this episode, Tyler and Annie’s discussion focused on confidently making smarter decisions to improve your life. They went in-depth on the acceptance of occasionally succumbing to cognitive bias, the importance of getting other people to discipline your decision-making, the concepts of resulting and hindsight bias, and the six step process to better decision-making.
Other topics included equanimity, understanding different versions of yourself, Annie’s process of writing her new book, Seth Godin’s advice to Annie, Daniel Kahneman’s inside and outside views, why your gut doesn’t constitute as a decision tool, a dozen decision-making books, Annie’s advice for reading long books and much more!
The following books were mentioned in the show:
How to Decide, by Annie Duke
Thinking in Bets, by Annie Duke
Behave, by Robert Sapolsky
The Success Equation, by Michael Mauboussin
Super Forecasting, by Phil Tetlock
The Biggest Bluff, by Maria Konnikova
Perfectly Confident, by Don A. Moore
Thinking Fast and Slow, by Daniel Kahneman
The Psychology of Money, by Morgan Housel
Super Thinking, by Gabriel Weinberg
Indistractable, by Nir Eyal
Connect with Annie:
Website: https://www.annieduke.com/
Facebook: https://www.facebook.com/AnnieDuke
Twitter: https://twitter.com/AnnieDuke
LinkedIn: https://www.linkedin.com/in/annie-duke/
Youtube: https://www.youtube.com/channel/UClDhEz5b55RH1ZfEZd7Y3hA
Apply for coaching with Tyler! The world's top performers in any field have a coach to help them achieve drastically greater results and in less time. The most successful real estate investors are no different. To apply for a results coaching session with Tyler, visit coachwithtyler.com.
This episode of Elevate is brought to you by CF Capital LLC, a national real estate investment firm that focuses on acquiring and operating multifamily assets that provide stable cash flow, capital appreciation, and a margin of safety. CF Capital leverages its expertise in acquisitions and management to provide investors with superior risk-adjusted returns while placing a premium on preserving capital. Learn more at cfcapllc.com.

Oct 13, 2020 • 57min
E95 - Realizing Dreams Through Intentional Personal Development with Jerome Myers
Jerome Myers aka “J” is the founder and Chief Inspiration Officer of Dreamcatchers and The Myers Development Group. Through these entities he lives out his childhood dreams of helping people manifest the things they imagine and create social proof that dreams should be real. Since leaving corporate America after building a $20M division, J has become one of the most sought after thought leaders in the multifamily development space. J is also currently the host of the DreamCatchers Podcast.
In this episode, Tyler and Jerome’s wide-ranging discussion focused on consciously pursuing personal development to achieve your dreams. They went in-depth on Jerome’s experience of dropping out of corporate America after having to lay off numerous people, setting up your life today for what’s to come, and believing in love while questioning whether certain beliefs and practices serve or hinder personal growth.
They also discussed gaining consciousness through pattern recognition and searching for more than the “three F’s”, cultivating your identity, focusing on multiple streams of income rather than a job, how a car crash inspired Jerome to become greater and much more!
Connect with Jerome:
Website: https://www.jeromemyers.co/
LinkedIn: www.linkedin/in/jeromemyers
The following books were mentioned in the show:
The Four Agreements, by Don Miguel Rodriguez
The Celestine Prophecy, by James Redfield
You’re Dreams Should Be Real, by Jerome Myers
Apply for coaching with Tyler! The world's top performers in any field have a coach to help them achieve drastically greater results and in less time. The most successful real estate investors are no different. To apply for a results coaching session with Tyler, visit coachwithtyler.com.
This episode of Elevate is brought to you by CF Capital LLC, a national real estate investment firm that focuses on acquiring and operating multifamily assets that provide stable cash flow, capital appreciation, and a margin of safety. CF Capital leverages its expertise in acquisitions and management to provide investors with superior risk-adjusted returns while placing a premium on preserving capital. Learn more at cfcapllc.com.

Oct 9, 2020 • 58min
E94 - Designing Your Life Through Assisted Living Investing with Gene Guarino
Gene Guarino is the founder of the Residential Assisted Living Academy. The RAL Academy is the premier source for education in owning, operating and investing in Residential Assisted Living and senior housing. Gene has trained thousands of people from across the country how to turn single family homes into cash flow machines. RAL Academy’s motto is Do Good and Do Well. Gene has written four books and hosted three radio shows and has spoken in five countries and over 50 cities in the last year alone.
In this episode, Tyler and Gene’s discussion focused on using residential assisted investing as a vehicle to design the life you want. They discussed the importance of understanding why you chose real estate investing, creating generational wealth, Gene’s advice for cherishing the present, training your mind to see silver linings, the best investment Gene has ever made and how to get involved in residential assisted living.
Other topics included the current state of interest rates, opening yourself up to opportunities, benefitting from masterminds, spirituality and beliefs, looking for the good in things and more!
Connect with Gene:
Free ebook: www.ral101.com
Website: http://www.residentialassistedlivingacademy.com
Instagram: https://www.instagram.com/ralacademy/
The following books were mentioned in a show:
Unlimited Selling Power, by Donald Moine
Stay Interesting, by Jonathan Goldsmith
Act Now, by Kevin Harrington
Apply for coaching with Tyler! The world's top performers in any field have a coach to help them achieve drastically greater results and in less time. The most successful real estate investors are no different. To apply for a results coaching session with Tyler, visit coachwithtyler.com.
This episode of Elevate is brought to you by CF Capital LLC, a national real estate investment firm that focuses on acquiring and operating multifamily assets that provide stable cash flow, capital appreciation, and a margin of safety. CF Capital leverages its expertise in acquisitions and management to provide investors with superior risk-adjusted returns while placing a premium on preserving capital. Learn more at cfcapllc.com.

Oct 6, 2020 • 1h 8min
E93 - Raising Capital Through Digital Marketing and Continual Improvement with Adam Gower Ph.D.
Adam Gower Ph.D. is an authority in content marketing and online communications for the real estate industry. He has more than 30 years and $1.5 billion of transactional experience in commercial real estate finance and investment. Today he builds best of class digital marketing platforms for private clients so they can raise more capital online and provides online courses for those who want to do it themselves.
In this episode, Tyler and Adam’s discussion focused on Kaizan, a Japanese term for continual development, and digital marketing in real estate. They discussed the implications that the Jobs Act of 2012 had on capital raising, overcoming the imposter syndrome, the power of putting your story online, the challenge sponsors face raising money online and opportunities for passive investors.
They also discussed Adam’s journey to Japan, aiming for progress but not perfection, investing in your own knowledge, Adam’s improvement with search engine optimization, how Adam stays hyper-focused on the task at hand and much more!
The following books were mentioned in the show:
The Secret Life of Real Estate and Banking, by Phillip Anderson
Connect with Adam:
Website: gowercrowd.com
Twitter: https://twitter.com/GowerCrowd
Facebook: https://www.facebook.com/GowerCrowd/
LinkedIn: https://www.linkedin.com/in/gowercrowd/
Apply for coaching with Tyler! The world's top performers in any field have a coach to help them achieve drastically greater results and in less time. The most successful real estate investors are no different. To apply for a results coaching session with Tyler, visit coachwithtyler.com.
This episode of Elevate is brought to you by CF Capital LLC, a national real estate investment firm that focuses on acquiring and operating multifamily assets that provide stable cash flow, capital appreciation, and a margin of safety. CF Capital leverages its expertise in acquisitions and management to provide investors with superior risk-adjusted returns while placing a premium on preserving capital. Learn more at cfcapllc.com.

Oct 2, 2020 • 1h 2min
E92 - Leveraging the Power of Crowdfunding with Jillian Sidoti
Jillian Sidoti is an attorney, speaker, entrepreneur, mama, and former college professor. Forever focused on finding the best and least challenging path for entrepreneurs to find funding for their deals, Jillian has written equity and debt offerings for all kinds of industries, including real estate, biotech, film, software, alcoholic beverage, cannabis, and green tech. Jillian’s client list includes Grant Cardone, Than Merrill of AE’s Flip this House, Tarek El Moussa of Flip or Flop, David Gross and more.
Jillian is the author of the Crowdfunding Myth. As a public speaker, she often offers fun and relatable content that leaves the audience with a deeper understanding of raising capital. Jillian is the founding partner of Crowdfunding Lawyers, LLP.
In this episode, Tyler and Jillian’s discussion focused on leveraging crowdfunding to build wealth for yourself and others. They discussed how Jillian developed a poverty mindset in the music industry, the biggest issues sponsors should be aware of in the current legal environment, Jillian’s advice for her clients beyond the operation of their team, tips for passive investors prior to executing a private placement memorandum, Regulation A and more!
Other topics included investing in yourself through volunteering, the idea of everything being “figure-outable,” accountability partners, dealing with her kid’s having COVID, and transcendental meditation. This is a highly informative episode for entrepreneurs looking to build their business!
Connect with Jillian:
Free ebook: https://bit.ly/JillianSidotiBook
Website: crowdfundinglawyers.com
Twitter: twitter.com/jilliansidoti
Facebook: https://www.facebook.com/groups/3046697892083948/
The following books were mentioned in the show:
The Bible
The Power of Now, by Eckhart Tolle
The Count of Monte Cristo, by Alexandre Dumas
Apply for coaching with Tyler! The world's top performers in any field have a coach to help them achieve drastically greater results and in less time. The most successful real estate investors are no different. To apply for a results coaching session with Tyler, visit coachwithtyler.com.
This episode of Elevate is brought to you by CF Capital LLC, a national real estate investment firm that focuses on acquiring and operating multifamily assets that provide stable cash flow, capital appreciation, and a margin of safety. CF Capital leverages its expertise in acquisitions and management to provide investors with superior risk-adjusted returns while placing a premium on preserving capital. Learn more at cfcapllc.com.


