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Greeks In Tech

Former NFL Player Raises Over $130k In Investment From 36 Of His Omega Psi Phi Fraternity Brothers for His Tech Startup, Win-Win

Black fraternity networks are and have always been very powerful in supporting the goals of individual members and Mike Tauiliili Brown and his tech start-up Win-Win are a perfect testament to this in 2019.

Brown has a powerful story. A 2-time All American linebacker at Duke University and a proud Spring 2007 initiate Omega Psi Phi Fraternity, Inc., Mike graduated early from Duke with a Public Policy degree in 2008 and then spent four years playing football professionally, his first stop being in Indianapolis where he was a linebacker for the Colts.

After leaving the league, he moved to Silicon Valley where he made the transition from “tackling to tech”, teaching himself to code multiple languages and developing a design skillset. He immersed himself in the tech industry, leading the mid-market growth team at Kiip, a $32M venture backed mobile advertising tech startup and then started his own start-up, Win-Win.

We at Watch The Yard come across a lot of stories of Black greek tech entrepreneurs but Mike’s story and start-up stood out to us more than most because of the fact that he was able to raise over $130,000 in investment from just 36 of his frat brothers alone. He not only was able to raise from prominent members of his fraternity but he also provided ways for his neophytes to invest as little as $200 via an equity crowdfunding campaign, something that could build their wealth in the future.

We talked with Brown, who recently relocated the company from Silicon Valley to Houston, about his startup, his career journey and the inspiring power of Black fraternity networks.

Check out our exclusive interview with Mike Tauiliili Brown below:

How would you explain Win-Win to someone who has never heard of it before?

Well, we have recognized that charitable giving methods are outdated and most people wish there was a better way to give back, so Win-Win combines giving with gaming to make donating to charity more engaging and fun!

We partner with professional athletes – today we have 150+ players across the NFL and NBA – and they host online game tournaments, like an NFL Pick Em or March Madness bracket challenge, on the Win-Win platform. When fans join the tournament they make a voluntary, fully tax-deductible donation to a charitable organization chosen by the host athlete. In the tournament, fans earn points when they make the correct predictions and instead of winning money, they’re competing to win epic fan experiences that money can’t buy – like having dinner with their favorite pro athlete after the game, court-side seats, and more! This unique model is what we called #GamifiedGiving

It’s a Win-Win because athletes raise money for a cause they care deeply about, fans get priceless access and experiences all while gaining tax benefits, charitable organizations gain new hard-to-reach millennial donors, and Win-Win makes money every time it happens! #WinWin?

Why do you think it is important to build a company focused on making the world better?

Let me be clear, we’re in this to create wealth and success just like most tech startups. That said, I don’t believe you have to compromise or choose between making an impact and making a profit. Technology is amazing and there are so many obvious benefits, however, there are a lot of adverse effects that come with many of these shiny new social networking or on-demand dog walking apps. With so many real problems in the world, I think it’s critically important for us forward-thinking entrepreneurs to be leveraging technology to build solutions that truly impact the world in a positive way… while making a significant amount of money!

I think the days of assuming that do-good companies aren’t capable of reaching major (monetary) success are long gone! In fact, I truly believe that these are the companies that actually have a greater chance of reaching success because consumers today, particularly millennials, have shown that “impact” is a priority when deciding who to spend money with. I think it’s a beautiful thing!

You’re an Omega. As you’ve matured in your career and become successful, looking back, how do you think joining a Black fraternity has contributed to where you are now?

The decision to pledge Omega Psi Phi Fraternity, Inc. at Duke University, the “Winning QZ” chapter, has contributed to my journey tremendously!

Ironically, I had no idea what a fraternity or sorority was when I got to Duke — had never even heard of it. I’m half Samoan, half Black and I was raised by my single mother – a foreigner from Samoa. So I was never exposed to black Greek life, or any Greek life for that matter. Nonetheless, joining Omega Psi Phi was one of the best decisions I’ve ever made, for a number of reasons!

Looking back, there are countless relationships that I’ve benefited from, and added value to, that came simply because of the common bond we share. Omega has played a big role in my career and getting to where I am today. For example, when I was starting Win-Win, the first several phone calls I made were to the bruhz! Through it all though, I’ve made sure that I’m giving to the bruhz more than I’m receiving and because many so Omegas have that mindset, it has resulted in a transformational experience. Friendship truly is essential to the soul! Roo

(Duke Chapel Step Off, 2008)

You are currently in the process of raising money and you have actually had a lot of support from your own fraternity brothers and individual D9 members as a whole. How do you think being a part of the Black greek community is an advantage for entrepreneurs?

Yes! We are currently raising capital from investors for my tech company, Win-Win. Since starting the company, we’ve successfully raised over $1.5 Million and our first investor check came from one of my beloved brothers in Omega: 2X Super Bowl champion Malcolm Jenkins from the Philadelphia Eagles. He pledged at The Ohio State University, Iota Psi chapter, and also crossed in Spring 2007 like me. We initially were connected due to the simple fact that we shared a common bond through Omega, and he would eventually become an investor, advisor, and one of our best athlete partners on the Win-Win platform. Since then, I’ve just been blown away by the level of support from my Fraternity brothers across the world — though it’s honestly not a huge surprise.

Now that we’re raising our second investment round from investors, I decided to provide the opportunity for any and ALL of my Fraternity brothers to invest in the company. We’re doing this through an Equity Crowdfunding Campaign, which gives ANYBODY the opportunity to invest as little as $500. By investing, my fraternity brother, and any others who invest, will own Win-Win equity shares and when we reach our goal of being acquired by a larger company, or going public (IPO), they will receive a return on their investment. Since launching the campaign we’ve had a large number of my fraternity become investors, many of which are first time investors! To date, we have over 30 Omegas who’ve collectively invested $130,000+ into Win-Win. Omegas from my chapter’s charter line, Spring 1974, all the way up to my own Neos have invested in Win-Win and I couldn’t be more excited about that — I set owt a hop every time an Omega becomes a Win-Win investor!

I’ve also been very appreciative of how members of various D9 organizations have also invested in the company and offered their support. This really speaks to the common bond we ALL share and to see that come to life is a real treat. Our campaign is about to end very soon so I’d encourage everyone seeing this to go go invest in Win-Win right now and get equity in the company! The website to learn more and invest is

In what ways can members of Black fraternities and sororities financially empower themselves and the community by investing?

I’ll be honest, I didn’t know very much about investing and the power of owning equity before I moved to Silicon Valley. However, I’ve learned a lot and I can’t stress enough how critical it is for us to know what’s going on and how generational wealth is created and sustained. Honestly, working 40 hours a week for someone else isn’t going to create wealth — not for you anyway, but most definitely for the owner of the company and their investors. Let me be clear, there is nothing wrong with working 40 hours a week and using your talents to add value to a great company — in fact, we’re hiring so hit me up! However, you must be educated about investing and understand the importance of equity ownership. That’s why I was so excited about the JOBS Act that Obama pushed through — it now enables anybody to invest in private companies and tech startups.

I would directly challenge every single member of a Black Greek letter organization to check out, a leading equity crowdfunding platform, and begin looking into and investing in tech companies. You’ll see a whole list of innovative companies on there currently accepting new investors. You can invest as little as $50 in some companies, and as you diversify your portfolio by investing in multiple things you give yourself a much bigger chance of getting a great return on your investments. If people take me up on this challenge, they can use my company’s campaign as the first step towards becoming an investor! We’ve picked up great momentum but there’s a limited window of opportunity left at this point.

When you finished playing in the NFL you taught yourself to code. What made you do this?

Anything that I commit my time to I plan to be the damn best! When I decided to go from “tackling to tech”, it was no different. Mind you, I didn’t know what Silicon Valley, or a tech startup, was until 2013. I ended up in a program for aspiring tech entrepreneurs called Draper University in Silicon Valley and I noticed that coding was an important skill set in the startup world. So, as part of my commitment to be the best, I figured I needed to acquire these skills. After finishing #1 in the Draper University program, I spent the next 9 months teaching myself to code several programming languages. That decision has proven to be a great one! However, I don’t want people to think that you MUST know how to code to create or work at a tech company. It’s one of the biggest misconceptions our communities have about tech. That said, knowing at least the basics of how to code is a very valuable skill to have, even if you’re not building apps or websites! The best part is that there are so many free tools and software that you can start with.

As someone who has had an NFL career, a tech career and created a startup, what are some skills you think undergrads or recent grads should pick up in order to make themselves more successful?

Well, as I just mentioned coding is a great skill to acquire in today’s technology-driven world. But beyond that, I think the single most valuable skill to have is a “soft” (intangible) skill: building genuine relationships. From a high level, this should be applied to your life in general. However, I strongly believe that your ability to forge authentic relationships with a wide variety of people has a direct correlation on your success. I love meeting dope people who are chasing their dreams and reaching success in their respective lanes. Building a relationship with these types of people have proven valuable time and time again. Let’s not forget though, a big part of building real, authentic relationships is first being a person of high character. Further, you should be looking to add value in these relationships as opposed to only looking to get something from people. Give more than you get, and you’ll end up getting way more that you could’ve imagined. One motto I’ve lived by since I was in middle school is “you’re the average of the five people you spend the most time with”. Look at your circle and assess if they’re on the path that has a similar destination that you desire. If not, change up that circle, or push them to level up… even if that’s your linebrothers/sisters!

How can people reading this support you and your mission?

Well, there are a number of ways. Number one, at the moment, would be going to check out our equity crowdfunding campaign ( and investing. Number two would be creating an account on the Win-Win platform ( and joining our upcoming NFL campaigns. We’ve got some big ones launching soon! Number three would be reaching out to our team ( and sending their resume because we’re hiring in a few different functions including marketing, business development/sales, and engineering. We’re always looking for talented people, especially minorities, to add to our growing team.

Lastly, if anybody has connections to pro athletes and celebrities who they think would be interested in using the Win-Win platform to raise money for charitable causes we are always open to having a conversation so reach out!

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