Words Of Wisdom With Tyler Smith — SkySlope and MyOutDesk Embrace The Future

Daniel Ramsey
7 min readNov 24, 2021
TYLER SMITH, CEO/FOUNDER OF SKYSLOPE, INC

I hopped on a Zoom call with the infamous Tyler Smith. If you’re in the real estate business at all then you are likely familiar with at least his company; SkySlope. Tyler founded SkySlope in 2011 and since then they’ve grown to become the industry leader in digital transaction management software.

Once upon a time, Tyler earned a spot on Realtor Magazine’s coveted “Top 30 Under 30” list, when he was a hotshot realtor himself. His experience in the real estate game lead him to want a better way to do business, hence his creation of SkySlope. It started off as merely a platform for taking brokerages paperless and has evolved over the past 10 years into much more.

Tyler and I have known each other for years, which should come as no surprise being that we’re both fairly successful entrepreneurs in Sacramento, California.

This “Zoom bro hangout” ended up being a value-packed conversation that covered numerous topics. From the current state of our economy to the future of real estate business and technology, it’s hard to pick just one discussion topic from the whole session.

So that’s why I didn’t! Instead, I’ll highlight a few of the more interesting matters they discussed. This is value-packed.

DON’T STOP SWIMMING

Did you know that if a shark stops moving then it stops receiving oxygen, and ultimately dies? They have to keep moving to stay alive and keep that title of an apex predator. The same can be said about an entrepreneur trying to find lasting success. Evolve or die, as they say. Tyler and I know this, and that’s why over the years our businesses have only grown more successful with each stage of their evolution.

SkySlope started as a platform with the tagline, “No paper!” because that was the simple foundation of what Tyler set out to achieve. Brokerages were using the same archaic method of document storage; endless rows of filing cabinets. Important paperwork would get lost, misplaced, or be full of errors, thus setting themselves up for failure in future audits. So Tyler gave them SkySlope; a means of moving all of that paper to the cloud.

As the platform grew in its acceptance across the industry, so too grew the features they offered. Tyler recognized that they needed to do more, or risk getting left in the dust by whoever did.

A COUPLE OF SHARKS

They added 24/7 technical support, something not a single other company offered. Because real estate isn’t confined to a 9–5 schedule, neither should the tools realtors rely on. Furthermore, Tyler didn’t want brokers to have to juggle different applications, log-ins, accounts, etc. So they added more features, like DigiSign, as an effort to make SkySlope a one-stop shop for progressive realtors. And it continues to do so, as they’ve expanded into the world of forms as well.

This is all to say, never stop moving.

Amazon started its success as a website to buy books. But why stop there? They didn’t, and now it’s the one place consumers can go to get just about anything they can imagine.

I maintain a shark mindset myself, with MyOutDesk. Why stop at virtual assistants for simple busy work and administrative tasks? So I didn’t; and I focused on hiring professionals with a wider array of skills and experience, not typically seen in remote-only workers. From marketing expertise to inside sales, from graphic design to customer support—MyOutDesk expanded to meet the demands of its customers, just as SkySlope did.

IT’S REAL-TOR, NOT REAL-TER

The future of the real estate industry is uncertain. That’s easy to say because even the “present” of the real estate industry is uncertain! With the housing market doing peculiar things these days, the services and technologies that support realtors need to be more flexible and reliable than ever.

More buyers and sellers are looking to technology to help them close their deals, be that trusted websites offering new services or the latest convenient app with everything in one place.

Unfortunately, the broker’s value has gone down with the rise of technology. No one wants to drive around looking for “for sale” signs, or tag along with a realtor to open houses when they can get the same experience at home on their laptop. Consumers want convenience, and realtors need to adopt software that allows them to add their own value in addition to digital convenience if they want to stay alive.

“Goodbye realtor, hello influencer.” — Tyler Smith

AGE OF THE INFLUENCER

Tyler plans to triple down next year(2022) on experimentation and focusing on individual realtors. In the past SkySlope has focused more on being the ultimate tool for a broker, encouraging them to sign up and provide the software to their agents.

Now the plan is to focus on those realtors themselves a bit more.

Tyler believes in just five years there will be drastically fewer brokerages operating, and more individual realtors utilizing tech to support their efforts. So this also means being more influential. The era of social media influencers has been upon us for some time. And while some industries may have fallen off a bit in their reliance on “influencers”, some industries seem tailor-fit for them. Who better to help you buy a house than that realtor on Instagram who has connections all over town? That guy/gal who can get you a deal on inspection costs, negotiate lower closing costs, and provide you with access to software that makes it all faster and easier.

I know this too, as it’s apparent by how many realtors employ our own virtual assistants to help them manage these unprecedented times.

WORDS OF WISDOM

I asked Tyler for his own thoughts on how to protect your business from these uncertain times we face. Hot topics like inflation and increasing rates of turnover have a lot of business owners concerned about being future-proof, and rightfully so. Here are the three things Tyler mentioned:

3 KEYS TO BEING FUTURE-PROOF

  1. Culture — A skilled professional can work anywhere. People are getting pickier about where they choose to invest their time and effort, and they aren’t settling anymore. So this runs deeper than just offering a bit more money; you have to pull your employees in and make them feel like an important part of your company culture. SkySlope used to do weekly all-hands meetings, where everyone would stop what they were doing and listen to announcements, make their own shout-outs, and converse. With remote work increasing you can still maintain your culture like this, via Zoom events or invites to the office for special occasions.
  2. Vision — A companies direction will often shift over time. Their goals and directives will evolve and expand. And so one thing that should never change is their overall vision. A business owner should know what their company vision is from day one, and never lose sight of it. And your employees should always be aware of that vision and feel like their role contributes directly to it. If they believe in your vision, they’ll believe in you. And good workers stick around for what they believe in.
  3. Great leaders — Not “good”, but great. Resentment, lack of respect or faith, are things employees can and will experience if they don’t have a great leader. This doesn’t mean employing some hard-ass to micromanage them into the ground for the sake of quarterly numbers. It means having leaders who can relate the vision to their employees, make them feel connected to it via mutual goals. So great leaders instill inspiration by practicing what they preach and thus motivate hard workers. A great leader can also be flexible when appropriate, but firm when necessary.

YOU WORK FOR THEM

All three of these points can be felt by our employees at MyOutDesk, which is yet another reason I hold so much respect for Tyler. We both share similar values, convictions, and beliefs. We both understand the value of people, and that at the end of the day the people don’t work for us, we work for the people. Our job is to provide a healthy, motivated, and positive workplace for our employees so that they want to work for us, and want to kick ass doing it.

In turn, we generate a better product that can keep up with the times and keep our customers around too. Literally, everyone wins—when you approach the way you do business with these things in mind.

WHERE WE COME IN

There are a lot more nuggets of wisdom and advice than we have room to discuss here. And if you’re not already a MyOutDesk virtual assistant user, why not?

Click this link to request a one-on-one consultation with an expert of ours.

We like to listen to your story and understand whatever roadblock or speed bump you’re facing. Then we propose a plan to help, take it or leave it. With these wild times ahead of us, affecting every industry differently, you have nothing to lose and everything to gain.

So don’t be shy; ask for help.

--

--

Daniel Ramsey

Daniel Ramsey is an entrepreneur, founder, and CEO of MyOutDesk, a company that provides virtual staffing solutions to businesses in various industries.