Looking Ahead To 2020

As 2019 comes to a close, this is a good time to consider what we see ahead for 2020 beyond economic and market issues.

Windward Wealth Strategies intentionally works to provide more than an investment strategy that is consistent with a client’s risk tolerance. We also help with tax issues, estate planning, charitable giving, protecting personal data and other areas that impact all of us. With that in mind, here are a few predictions and trends you can anticipate in the year(s) ahead, specifically related to all of us as consumers:

  • If you’re flying in the United States after October 20, 2020, you will need a Real ID compliant card. An updated DHS driver’s license should have a star in the upper right-hand corner, or you can use a valid passport or military ID for travel. The Department of Motor Vehicles provides information on what’s required to obtain a new Real ID license.
  • In addition to autonomous vehicles, facial recognition software and other uses of Artificial Intelligence, there are some other uses that aren’t necessarily beneficial. It’s worthwhile to know that AI is already being used for cyberattacks, including ransomware, identity theft and fraudulent financial transactions. Experts have shared that ultimately, the best way to combat malicious AI is with AI itself, which will adapt as cybersecurity evolves to avoid security “blind spots.” As consumers, we need to use common practices such as: using and continuously updating antivirus software; being on the lookout for suspicious emails from trusted sources, like companies you work with; using complex passwords and/or a secure software password protection program (like Keeper); and checking bank and other financial data regularly for any inconsistencies. Cyber experts anticipate that AI and speech technology will be used to exploit consumers with phone calls that will have the recipients believe they are talking with a person they know or a representative of a company they have a relationship with. Nationally, a bipartisan bill (TRACED Act) to protect consumers from robocalls passed the House and is expected to pass the Senate soon. Shortly after, the President will likely sign it into law. This will place more of the responsibility on wireless service companies to provide greater security protection for mobile phones.
  • Disinformation and fake news are spreading in the public and private sectors and being used as a weapon by nation states. In 2020, we will see more of the stark reality that deep learning algorithms can bring, using seemingly realistic images and videos. Be wary of this type of activity, especially through social media. As one example, many Facebook® and Instagram® users saw fake news involving celebrities who supposedly left their regular work and have started their own clothing or cosmetics companies. Those behind this disinformation hoped to steal user data when they logged on to a linked website.
  • One of the most significant issues in the future is what governments throughout the world will do to protect our privacy. Will privacy become a top-level priority, and what are the implications for enterprise data management? Advertisers on Google®, Facebook and Amazon® have been using data for some time to target customers. Google’s recent acquisition of Fitbit®, in particular, means the tech giant has access to years of fitness and related data for tens of millions of consumers. The questions is: what will they do with that data? That’s just a singular example of data mining that will surely continue to be exploited.


Protecting personal data and preparing for changes in technology requires knowledge of what tactics hackers use and vigilance in protecting one’s personal information. You may already be using some of the following tools or doing your best to avoid certain risks, but here are some recommendations:

  1. Don’t use public Wi-Fi or use it sparingly only for sites that don’t involve secure access.
  2. Immediately delete any emails from sites that you suspect may be represent phishing.
  3. For desktop computers and mobile devices, use auto-lock to keep your device safe from unauthorized use.
  4. Use two-factor identification whenever it’s available for banking and any other financial transactions.
  5. Access the site “haveibeenpwned.com to find out if any of your email addresses (assuming you have more than one) have been hacked.
  6. Change passwords regularly, make sure they aren’t all the same and consider using a password encryption program for desktops and mobile devices.
  7. Make sure your home wireless network is set up with a secure password.

If you have any questions regarding personal security or if you want to review any security or related issues in greater detail, please let any of us know. Have a happy and safe 2020!

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2019 Windward Investment Review

This is our annual review of the markets for the year and where we might be going.  It starts off with basic investment principals and gets more detailed about the economy, government spending and global markets at the end. Feel free to jump to the part that interests you the most. Enjoy!

This is our annual review of the markets for the year and where we might be going.  It starts off with basic investment principals and gets more detailed about the economy, government spending and global markets at the end. Feel free to jump to the part that interests you the most. Enjoy!

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Windward Wealth Strategies Holiday Parade

Windward Wealth Strategies is the proud lead sponsor of this year's Oshkosh Holiday Parade. Mark your calendar for November 16.

Windward Wealth Strategies is the proud lead sponsor of this year's Oshkosh Holiday Parade. Mark your calendar for November 16.

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Greg Pierce on the win for an Oshkosh arena


With this effort, we saw an opportunity to marry an investment opportunity, a passion in sports and a need for development in Oshkosh. 

About a year and a half ago, we became aware of where the City of Oshkosh was headed with the Buckstaff property. What people didn’t notice behind all those buildings is a beautiful view of Lake Winnebago. There was just really a lack of ideas about what to do. In terms of development, and really maximizing the potential of that property, there was nothing being thought about at the time. 

It started as a baseball project. I love baseball and minor league baseball, and wood bat league stuff can be a great business, but we are surrounded by it, so we went from that to basketball because we figured out that the NBA was requiring all NBA teams to have development league teams. The Bucks did not have one, and the move with almost every one of them was within 100 miles of home. 

I’m kind of a professional fan. I travel a lot for work. If I have time, rather than sit in a hotel room, I’ll go to a game. I’d been in stadiums throughout the country and kind of just an observer of what goes on. We saw this movement that’s happening, that you’re now getting with the Titletown District in Green Bay and the entertainment block the Bucks are creating in Milwaukee. You’re building these year-round facilities that can handle and help finance these projects, because without them, you can’t make a go of it 30 times a year. We figured out that we could do a mini version of the entertainment block with some bars, restaurants, retail, and then there’s definitely office space needs in this area of Oshkosh. We have interest from health care. We could possibly locate a clinic on-site. We may do condos or multifamily. 

If you look at the Sawdust District plan, about half of it is going to be things that we’ve proposed to do or move forward on. In that broader plan is a plan for a second, larger arena. If you look at youth sports tourism, there’s a lot going on in the state of Wisconsin that’s outdoor. There are not a lot of indoor court facilities, though, and when you get to ice, it’s even worse. We believe that second building, beyond being a bigger facility to handle a D-League team as the D-League grows and expands, is a youth sports opportunity. We can create opportunity for attracting people to the community all year round. 

We’ve been approached for conventions such as a political party hosting a state convention in our building. We’ve had a gymnastics regional tournament talk about hosting with us. We’ve had people talk to us about Christmas parties. We have three lounges where we can accommodate anywhere from 140 to over 200 people in a nice lounge that has a unique setting that oversees the arena. It’s been all over the map. Just from a concert standpoint, we have three different settings that we can really make a profitable deal at 1,000 or 1,500 people. 

That all fits the idea of an entertainment district. We need to generate traffic through there. What’s interesting is almost all of them are new ideas. (It’s not) like we’re displacing anybody from anywhere else. Many of them are new things. 

Look at how many people turn out for things like Waterfest in Oshkosh every Thursday in the summer and Country USA and all these things. The Timber Rattlers are a model franchise in Class A baseball in terms of what they draw for attendance. Look at the Packers being the story that they are. There are sports fans here. We feel pretty good about that. That’s what our message has been. The building is getting built because of a basketball team. We wouldn’t do it if it wasn’t for that, but look what else can happen from here and what else this can spur. It has been absolutely unbelievable. 

Source: Insight Magazine May 2017

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Contact Us

Windward Wealth Strategies Northeast Wisconsin Office 2370 State Road 44 STE A Oshkosh, WI 54904