Pop Quiz, Monday with Joy Schoffler, Chief Strategy Officer at Upside Avenue

Art Legends
Art Legends in History
4 min readNov 3, 2018


Photo credit: Joy Schoffler

The Pop Quiz, Monday is a fun little exam that we love to give to savvy business owners. The examination is not a surprise after all since the interviewee already knew about the questions in advance. However, we can always pretend and have fun with the scenario of a young entrepreneur sitting in class nervously biting on their pencil. They are ready to take a pop quiz on a chapter that they were supposed to read the night before. Instead, they played Metroid all night on their SNES (Oops, this was me in high school). The real purpose of the pop quiz is that this is a fun way to introduce business tips from real-world experiences that you can not learn in a classroom. We want to thank our entrepreneur for being a good sport and volunteering their time to answer a few questions to help our community grow from their knowledge.

I want to introduce you to our guest today who will be taking our Pop Quiz Monday.

Can you please tell everyone your name?

Joy Schoffler

What is your job role?

Chief Strategy Officer

Tell us about your company?

Upside Avenue is a Public, non-traded multifamily income REIT, which co-invests alongside their family office, SMAs, and high net worth investors in cash-flowing multifamily, senior living and student housing properties with highly vetted sponsors throughout the U.S. We are part of a 16-year-old investment firm that has a long history of producing above market returns to investors in both up and down markets.

What do you love most about your job?

I love that I am helping all investors to gain access to investment products which have historically only been open to the top one percent of investors.

What motivates you to get up every day and go to work?

My biggest motivation is to help others build passive streams of income and achieve financial security. I believe the only way to have true freedom in life is to have economic freedom. I love helping people build that.

How do your co-workers inspire you?

I work with a team of caring and passionate people. Our company does more than list our values on our website, and we have quarterly training meeting to ensure that we are living by them and holding ourselves accountable to them. We also serve our community. We do gift card give-a-ways to the homeless during the holidays, have fantastic opportunities for training and celebrate all of our employees from maintenance personnel at properties to executives. It is inspiring to see how much people care.

How do you have fun at work (team building, pranks, etc..)?

We do potlucks, Halloween costume contests, scavenger hunts, have big parties where we celebrate the accomplishments of staff, and make lunch together in the break room. It is an enjoyable place to work! We also do pop up gift card give-a-ways at stores during the holiday season. It is very fun.

What are some of the challenges of your job?

While we have been around for the last 16 years, we have never had a way for all investors to work with us. We typically only allowed high net-worth and institutional investors to participate. My job has been to ensure our income REIT had the technology and the usability to handle the scale that comes from enabling all investors to invest for as little as $2,000 in a fully compliant manner. This has been a big challenge, but it is also very rewarding and has been a lot of fun.

What are some lessons learned from a past project that you can share with us?

One of the biggest lessons that I have learned is that it can be much less expensive with a better user experience to buy technology than to build it. I see so many technology companies starting from scratch, spending a good deal of time and money in the process–that did not need to be spent.

What advice would you give to someone who is starting in your industry?

Working in the investment industry is long gameplay. Always do right by your investors and make sure to be fully transparent. Your investors do not expect everything to be perfect all the time, but they do expect honesty and will be with you for many deals if you give them that.

Thank you for taking our pop quiz today. You get an A+ for effort. You can learn more about our interviewee and their business by visiting them on the web:


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