&l;em&g;&l;span&g;First on his hit list? Ending extreme hunger &a;ndash; and he may have a shot at it. &l;/span&g;&l;/em&g;
&l;em&g;&l;span&g;Meet Tony DiMatteo, CEO of Lottery.com. The first time I met Tony we were in a garden at the Vatican. I convinced him to come join me for an impact investing forum (not a tough sell) after&a;nbsp;his work trip in Norway. It was over&a;nbsp;bucatini all&s;Amatriciana&a;nbsp;and green tea that I got to know him well and found myself moved by his style of leadership and genuine drive to do good in the world.&l;/span&g;&l;/em&g;
&l;em&g;&l;span&g;Fast forward a few months later and he joined us onstage at the Forbes Impact Summit (as a partner and sponsor) where he &l;a href=&q;https://2018diamondball.com/&q; target=&q;_blank&q;&g;launched a partnership&l;/a&g; with Rihanna&a;rsquo;s nonprofit, the &l;a href=&q;https://www.forbes.com/sites/elanagross/2018/07/24/how-rihannas-clara-lionel-foundation-is-changing-the-emergency-response-model/#133d672010f1&q;&g;Clara Lionel Foundation&l;/a&g;. &l;/span&g;&l;/em&g;
&l;em&g;&l;span&g;&a;nbsp;&l;/span&g;&l;/em&g;&l;em&g;&l;span&g;This is our most recent conversation together. &l;/span&g;&l;/em&g;
&l;strong&g;&l;span&g;Brendan Doherty:&l;/span&g;&l;/strong&g;&l;span&g; Tony it&a;rsquo;s great to see you again and really for our conversation. I&a;rsquo;d love to start somewhere near the beginning. Could you tell me a story from your younger life that influences you and your work today?&a;nbsp;&a;nbsp; &l;/span&g;
&l;strong&g;&l;span&g;Tony DiMatteo:&l;/span&g;&l;/strong&g;&l;span&g; Like most entrepreneurs, I&a;rsquo;ve failed at a lot of things. Of course, what&a;rsquo;s kept me going is that I&a;rsquo;ve managed to have a few base hits along the way. Those dramatic ups and downs are what have prepared me for the success we&a;rsquo;re having at Lottery.com.&a;nbsp; &l;/span&g;
&l;span&g;I started out life with no intention of ever being an entrepreneur, in fact I didn&a;rsquo;t even know what that word meant until I was about to graduate high school. After a very bleak and sobering conversation with my history teacher about &a;ldquo;going out into the real world after graduation&a;rdquo; I realized that model was broken. I didn&a;rsquo;t want to have a nine to five day, week after week, maybe going on vacation if I could afford it, trying to live within my means while also saving for retirement, and hoping to never have a financial disaster along the way. Is the real reward in life retirement at 65 after spending my entire youth working? Why do I need to wait 50 years to enjoy life? About half of Americans will outlive their retirement savings, and either have to go back into the workforce, or become dependent on others. I didn&a;rsquo;t like those odds. I knew I would never have the life I wanted &l;em&g;just&l;/em&g; working for someone else, and I never wanted to be dependent on anyone. I&a;rsquo;m a true believer that everyone can and should be an entrepreneur at heart.&l;/span&g;
&l;strong&g;&l;span&g;Doherty:&l;/span&g;&l;/strong&g;&l;span&g; I often talk about&a;nbsp;Teddy Roosevelt&s;s quote, that the credit always goes to the one in the arena. And that&a;rsquo;s often the entrepreneur. So what happened after that chat with your high school teacher?&l;/span&g;
&l;strong&g;&l;span&g;DiMatteo:&l;/span&g;&l;/strong&g;&l;span&g; I decided that day that I was willing to take advantage of any and all opportunities that came my way and that I&a;rsquo;d always swing for the fences, no matter how many times I struck out. I thought that even if it took me 30 years of striking out as an entrepreneur, if I learned from every experience, treated people fairly, and kept developing my network, eventually I&a;rsquo;d hit a home run and I&a;rsquo;d never have to worry about running out of money before I died. That&a;rsquo;s been my life&s;s thesis, and that&a;rsquo;s what I&a;rsquo;ve been trying to prove for twenty years. It&a;rsquo;s been painful at times along the way, but always betting on myself has lead me to where I am now.&a;nbsp;&a;nbsp; &l;/span&g;
&l;span&g;I&a;rsquo;ve been an employee, and of course there is merit to that. I learned a lot, honed some valuable skills, and developed meaningful relationships. And I don&a;rsquo;t treat my team like employees. In my mind they are all entrepreneurs like me, capable of nearly anything, and it&a;rsquo;s my obligation to encourage them to swing for the fences too, even if it means they move on to something else. The world needs more entrepreneurs.&a;nbsp; &l;/span&g;
&l;img class=&q;size-full wp-image-100&q; src=&q;http://blogs-images.forbes.com/bdoherty/files/2018/08/Tony-headshot.jpg?width=960&q; alt=&q;&q; data-height=&q;948&q; data-width=&q;948&q;&g; Tony DiMatteo, CEO, Lottery.com
&l;strong&g;&l;span&g;Doherty: &l;/span&g;&l;/strong&g;&l;span&g;Couldn&a;rsquo;t agree more. I&a;rsquo;m a fan of promoting up and out. Incredible talent always needs growth and challenge. Of course, I want them to have that in my company but sometimes it means backing someone as they pursue their next project. So for you, what drives you, why do you wake up every day to do what you do?&l;/span&g;
&l;strong&g;&l;span&g;DiMatteo:&l;/span&g;&l;/strong&g;&l;span&g; Every day I wake up knowing there is more to accomplish and more to become &a;ndash; I&a;rsquo;m intrinsically motivated. No matter what wins or losses I had yesterday, or how much I want to stay in bed, or just give up and fall flat on my face, today I commit to myself to being better and giving the day my best effort. I have a deep belief that everyone should try to live a life of perpetual advancement too. My co-founder Matt Clemenson and I are driven every day to help people and create a massive vehicle for that. Matt and I knew we had something special that would truly change the world, and he&a;rsquo;s brilliant and hungry to help everyone - that kind of devotion makes me wake up and push every single day.&l;/span&g;
&l;span&g;One of my favorite sayings is &a;ldquo;Don&a;rsquo;t believe the world owes you a living. The world owes you nothing; it was here first.&a;rdquo; So I only expect to get what I earn for myself. I actually believe that I owe the world my best work every day. It&a;rsquo;s my responsibility to give as much back to the world that I can.&a;nbsp; So when I have an opportunity to help someone, I take it as my responsibility to contribute in whatever way possible.&l;/span&g;
&l;strong&g;&l;span&g;Doherty: &l;/span&g;&l;/strong&g;&l;span&g;I watched your &l;a href=&q;https://www.youtube.com/watch?v=N9Tw0mMXJ00&a;amp;feature=youtu.be&q; target=&q;_blank&q;&g;Puerto Rico video&l;/a&g;, which was great. In it you speak about servant leadership. What does that mean to you? What&s;s hard about it?&l;/span&g;
&l;strong&g;&l;span&g;DiMatteo:&l;/span&g;&l;/strong&g;&l;span&g; Being a servant hearted leader to me means knowing that even as a leader you can&a;rsquo;t possibly know everything about your team, project, mission, or whatever it may be. I find the best way to lead is to listen to the people who are closest to the situation and understand what they need, and then give them the resources to succeed.&a;nbsp;&l;/span&g;
&l;img class=&q;size-full wp-image-102&q; src=&q;http://blogs-images.forbes.com/bdoherty/files/2018/08/Tony-PR.jpg?width=960&q; alt=&q;&q; data-height=&q;402&q; data-width=&q;948&q;&g; Kamil Rivera from Off Grid Relief bringing light and joy to a home in Puerto Rico before the Power to the Pepole concert.
&l;span&g;&a;nbsp;&l;/span&g;&l;strong&g;&l;span&g;Doherty:&l;/span&g;&l;/strong&g;&l;span&g; In my last Icons interview, I actually spoke about the Japanese management concept of &l;em&g;Genba&l;/em&g;, which essentially&l;/span&g; translates as &q;go to the source&q; or the root, which is a style of management you&a;rsquo;re describing. I like it. So take me back to Puerto Rico.
&l;strong&g;&l;span&g;DiMatteo: &l;/span&g;&l;/strong&g;&l;span&g;When we went to Puerto Rico we realized how much more work needed to be done after the hurricanes and that there were still thousands of people without power and basic necessities. We knew we could help raise awareness and funds for the island, but it would be absurd to think that as outsiders we would have the answers. &l;/span&g;&l;span&g;&a;nbsp;&l;/span&g;
&l;span&g;It&a;rsquo;s really not hard. In fact, I think it&a;rsquo;s much easier to be a leader that serves than a dictator or a boss. The two are actually diametrically opposed. A boss points at you and tells you exactly what you&a;rsquo;re going to do next, and a leader points to the mountain that needs climbing, sets the vision, and asks &a;ldquo;who&a;rsquo;s with me?&a;rdquo;&l;/span&g;
&l;img class=&q;size-full wp-image-101&q; src=&q;http://blogs-images.forbes.com/bdoherty/files/2018/08/Tony-stage.jpg?width=960&q; alt=&q;&q; data-height=&q;404&q; data-width=&q;948&q;&g; DiMatteo onstage at the Power to The People fundraising concert in Puerto Rico.
&l;strong&g;&l;span&g;Doherty: &l;/span&g;&l;/strong&g;&l;span&g;I&a;rsquo;ve got my crampons, I&a;rsquo;m in! So how would you describe the mission of Lottery.com then?&l;/span&g;
&l;strong&g;&l;span&g;DiMatteo:&l;/span&g;&l;/strong&g;&l;span&g; I think what we do and what we are, are two very different answers. What we do is let people play their local and national lotteries from their phone, helping advance one of the last remaining paper-based industries go digital. We are now expanding into global impact raffles and sweepstakes with a goal to directly raise billions of dollars for good causes. For instance, with the new tax reforms in the US, The Council on Foundations has estimated that &l;u&g;&l;a href=&q;https://www.cof.org/news/council-foundations-statement-passage-tax-cuts-and-jobs-act&q; target=&q;_blank&q;&g;$16 billion to $24 billion&l;/a&g;&l;/u&g; will be drained from charitable giving in the US every year. If people no longer have the tax deduction as an extra &a;ldquo;carrot&a;rdquo; to donate to charity, we have to give people a reason to give, which is what we do with our impact games. People can now donate to a cause and have a chance to win a large jackpot, or a VIP experience like meeting their favorite celebrity, or meeting their favorite athlete.&a;nbsp;&a;nbsp; &l;/span&g;
&l;strong&g;&l;span&g;Doherty:&l;/span&g;&l;/strong&g;&l;span&g; Given that, how would you describe your company?&l;/span&g;&l;span&g;&a;nbsp;&l;/span&g;
&l;strong&g;&l;span&g;DiMatteo:&l;/span&g;&l;/strong&g;&l;span&g; What we are is a social good company that does things that others think are impossible. From start to finish we created the entire fundraising concert in Puerto Rico in three weeks with a killer line-up and streamed it on the homepage of Reddit. We had never put on a concert before, we just thought it needed doing and we could do it. Right now we are working with some very large international charities to raise billions of dollars to end extreme hunger in the world.&l;em&g; If we are successful in that, for the first time in human history there will be no hungry people on the planet.&l;/em&g; They&a;rsquo;ll always be more work to be done but that is an achievable goal that really is within reach. I would bet that most people think it&a;rsquo;s impossible for a company like ours to even partner with these charities, let alone to tackle a goal like ending extreme hunger, but we always find a way to get impossible things done.&a;nbsp;&a;nbsp;&a;nbsp; &l;/span&g;
&l;strong&g;&l;span&g;Doherty: &l;/span&g;&l;/strong&g;&l;span&g;When I first learned about Lottery.com, I was moved by how you&s;re flipping not just the business model, but also its ability to impact our world positively. You mentioned some of it but tell me more about that? What are some myths about what you do?&l;/span&g;
&l;strong&g;&l;span&g;DiMatteo:&l;/span&g;&l;/strong&g;&l;span&g; There are a lot of myths out there about the lottery. The truth is that about 70% of all tickets in the US are bought by people with incomes greater than $75k, which is our target audience and really all lotteries benefit good causes.&l;/span&g;
&l;span&g;At the state level lottery proceeds usually go to fund education in the state that the ticket is sold.&a;nbsp;&a;nbsp; For instance, the Georgia Lottery has a program called HOPE, which has distributed more than $8 billion in college scholarships to more than 1.8 million students. With raffles and sweepstake games, we can now directly choose a beneficiary charity and create incredibly engaging content and games for their donor base. This raises more funds for them than they would with a traditional fundraising drive.&a;nbsp;&l;/span&g;
&l;img class=&q;size-full wp-image-106&q; src=&q;http://blogs-images.forbes.com/bdoherty/files/2018/08/Lottery-AKON.jpg?width=960&q; alt=&q;&q; data-height=&q;643&q; data-width=&q;948&q;&g; Akon, Ryan Scott, DiMatteo discussing the future of fundraising and the Akoin at Gabbcon 2018.
&l;strong&g;&l;span&g;Brendan: &l;/span&g;&l;/strong&g;&l;span&g;Switching gears because what&a;rsquo;s a hip conversation without using &a;ldquo;blockchain&a;rdquo; at least once &a;hellip; what does our future world look like at the intersection of blockchain, philanthropy, and impact? &l;/span&g;
&l;strong&g;&l;span&g;DiMatteo:&l;/span&g;&l;/strong&g;&l;span&g; When I talk about the future of fundraising I think of it in two meanings. The first is that I truly believe that gamifying charitable giving, as we are doing with our sweeps and raffles, is the future of impacting fundraising. It&a;rsquo;s just a better way to engage your donor base and expand it, and give them an amazing experience as well.&a;nbsp;&a;nbsp;&a;nbsp; &l;/span&g;
&l;span&g;The second meaning is raising funds through tokenized securities on the blockchain. We are going through our own STO (Security Token Offering) right now tied to our global impact raffles.&a;nbsp; For maybe the first time ever, any accredited investor can invest into an impact startup, project, or fund, and have liquidity in twelve months, whereas historically you&a;rsquo;d be looking at a five to seven year period before you&a;rsquo;d expect any ROI. This type of liquidity is a complete game changer in my opinion and will unlock billions of dollar of impact investment from investors all over the US.&l;/span&g;
&l;strong&g;&l;span&g;Doherty: &l;/span&g;&l;/strong&g;&l;span&g;That kind of liquidity could be huge. I&a;rsquo;m curious, at a time when &q;disruptor&q; is the king of buzzwords, I&a;rsquo;ve heard you say Lottery.com is not one. Tell me why?&a;nbsp; &l;/span&g;
&l;strong&g;&l;span&g;DiMatteo:&l;/span&g;&l;/strong&g;&l;span&g; We always say that we are not here to disrupt the lottery industry, we&a;rsquo;re just here to help advance it, and the same is true of impact. This isn&a;rsquo;t a zero-sum game, you don&a;rsquo;t have to lose for me to win. It&a;rsquo;s possible for everyone to win together, and that&a;rsquo;s what we always try to do and it&a;rsquo;s the lens that we see the world through. Whenever we tackle a new project we think about all of the potential stakeholders and think about how they can benefit from what we are doing. Then we seek to align our interest to theirs so that everyone in the ecosystem benefits from what we are doing.&a;nbsp;&l;/span&g;&l;span&g;&a;nbsp;&l;/span&g;
&l;strong&g;&l;span&g;Doherty: &l;/span&g;&l;/strong&g;&l;span&g;How has your life been different than you imagined?&l;/span&g;
&l;strong&g;&l;span&g;DiMatteo:&l;/span&g;&l;/strong&g;&l;span&g; I think for the first time my life is exactly as I always imagined. It took a really &l;em&g;really&l;/em&g; long time to get here, but I&a;rsquo;m lucky enough to be doing amazing things, with amazing people, while helping as many people as possible. &l;/span&g;
&l;img class=&q;size-full wp-image-103&q; src=&q;http://blogs-images.forbes.com/bdoherty/files/2018/08/Tony-Enzo.jpg?width=960&q; alt=&q;&q; data-height=&q;711&q; data-width=&q;948&q;&g; Tony and Enzo DiMatteo.
&l;span&g; &l;strong&g;Doherty: &l;/strong&g;How would you like to be remembered?&l;/span&g;
&l;strong&g;&l;span&g;DiMatteo:&l;/span&g;&l;/strong&g;&l;span&g; I try not to think too much about things like that and just do my best each day. I&a;rsquo;d hope that if I&a;rsquo;m remembered at all, I&a;rsquo;m thought of as someone that lead an advancing life and that I gave more than I took from the world. &l;/span&g;
&l;strong&g;&l;span&g;Doherty: &l;/span&g;&l;/strong&g;&l;span&g;So who do you consider an Icon of Impact?&l;/span&g;
&l;strong&g;&l;span&g;DiMatteo:&l;/span&g;&l;/strong&g;&l;span&g; Actually, someone I met through the Forbes Impact event was Petra Nemcova, who I think is doing really incredible things and is definitely an Icon of Impact. She survived the 2004 Tsunami in Thailand by holding on to a palm tree for eight hours before she was rescued. She then started a charity which is now All Hands and Hearts - Smart Response which has helped over one million people and built over 170 schools. They provide rapid emergency response when a natural disaster happens to help rebuild, and more importantly they commit to staying in affected area for years to help people not just recover but thrive. She&a;rsquo;s also one of the nicest people you&a;rsquo;ll ever meet.&l;/span&g;&l;span&g;&a;nbsp;&l;/span&g;
&l;strong&g;&l;span&g;Doherty:&l;/span&g;&l;/strong&g;&l;span&g; She is pretty spectacular and was a compelling presence on Forbes Impact stage, I&a;rsquo;ll be sure to tag her in this interview! Thanks again, Tony.&l;/span&g;
Cramer: How compounding can help you double your money in 7 years 6:32 PM ET Fri, 22 Sept 2017 | 11:41 
