Dan O’Toole: AI, Arrive, Delivery, Drones, Entrepreneurship, Family, Passion, and Vision

Dan O'Toole is the founder and CEO of Arrive.ai.

Dan O’Toole is a visionary. 

I’ve known O’Toole, a serial entrepreneur who is now helming the massively-hyped startup Arrive.ai, for more than three years now. It’s rare that someone can win me over as quickly as he has. His energy is infectious, his vibe ever-present and upbeat. As a fellow Midwesterner, I know the type well. He is a man who has stuck to his values, his gut, and his intuitions- and has gotten paid handsomely for it. 

“I grew up in a small suburb of Indianapolis, and have been an entrepreneur since I was a kid. I got married a year out of school, and have four kids and two grandkids. I wouldn’t trade one failure for not knowing. Knowing is everything. I never want to second-guess something. I’d rather fail and know than not know at all. I was in sales from an early age, and in the third year I was making more than the president, and got a salary cut from up above. I started my own competing company, and then dominoed into one portfolio after another of businesses that I started. I got into the real estate business at the right time, had some great tenants, and built substantial net worth through my existing asset base.”

O’Toole, having a knack for being in the right place at the right time, believes he has found himself in a similar situation with Arrive.ai. Arrive, focusing on building the infrastructure for omnichannel autonomous delivery, is, by a wide margin, his biggest ambition yet. O’Toole, an avid gambler, knows a well-placed bet when he sees one. He soon shoved his chips to the center, and went all in.

“When I had the idea for Arrive.ai, I was focusing on how to solve a problem in consolidated facilities, and wanted to get out of the people business. It’s the biggest market opportunity in the world, and the biggest thing I’ve been part of. I sold my facilities business to one of our vendors to finance it. I put in $750,000 in the first six years, and did a lot of behind the scenes development to get it off the ground.”

O’Toole knows that this will not be an easy lift. What comforts him through this is that NOTHING in his life has EVER been an easy lift. O’Toole is a very simple man, when you boil him down. He loves to work, and has no plans on stopping to do so. Particularly when motivated by his ability to build things, create value, and provide for his family, he shows no signs of ever slowing down. 

“I want to support my family. My dad lost his job when I was 15, and I lied about my age to get a job at Hardee’s. I gave my parents my paycheck because I didn’t want to see my family go down. It was the right thing to do. I’ve always had a great work ethic and led by example. I’m bored when I don’t work. I don’t think I’ll ever stop. I love creating things that are big, meaningful, fun, and exciting. I would never want a job I didn’t enjoy. I believe we’re building the biggest company in the world at Arrive.ai.”

The first person that O’Toole credits for his outsized entrepreneurial success is his wife, who has been with him since before he had anything. Meeting just after graduating college at Ball State University, O’Toole knew immediately that she was going to be in his life for a very long time. More than anything else, O’Toole wanted someone who he knew that, no matter what happened, would stick with him. 

“We met at a social club in the neighborhood where we graduated college with my sister, and we hit it off. I didn’t get her number, but I gave her mine, and she called a few days later. I told my friends after that I met the girl I was going to marry. She’s the motivation for everything I’ve done. You want someone to provide and work hard for. Our deal was that she would raise the kids and I would make the money. We have the best four kids on Earth. We have a lot of love, and everyone stands on their own.”

O’Toole, also a father of four children whose ages range from their mid-30s to late teens, has crafted a family life and structure that most would find enviable. He talks with all of his kids every day, and has looped some into instrumental roles in either building out Arrive.ai or starting their own companies. It is love that powers O’Toole the most, far more than any entrepreneurial venture ever could. 

“It was sobering. It was a life-changing experience. There’s so much love that comes out of such a little person. You worry a lot because you care a lot. When we found out we were having a second, I was scared because I didn’t think I could love him as much as I loved my first. You quickly realize that’s false, and you worry about them all the time. I talk to my kids every day. I’m very proud of our family. They’re great. Family is everything. If you don’t have a family, you don’t know what you’re missing.”

In alignment with my personal belief that entrepreneurship is a born profession, O’Toole always knew that he would be one. Getting his start selling tickets before he hit double digits, he fell in love with the hustler’s mentality early on. He remarkably filed his first corporation at 12 years old, and found himself spiraling into countless industries before finally settling on building out Arrive, his biggest venture yet.

“They had a contest selling tickets when I was seven years old, and I sold so many, but I came in second because the winner’s dad helped him. They knew how hard I worked, and they made a second place award for me. I had a lawn care business, a promotion book, and formed my first corporation when I was 12 years old. I’ve always tried so many things. I’ve been in more businesses than I haven’t been in, and I’ve never quit. I knew I would find my niche, and I believe I finally found it with Arrive.ai.”

O’Toole story of how the idea for Arrive.ai was made manifest is one of my favorite stories I’ve ever heard in business. O’Toole was struck by a lightning bolt-esque spirit of inspiration on the way home from a business trip, and made the world shake trying to get Arrive’s first patent filed. He succeeded, and beat out Amazon and the United States Postal Service by days, securing his intellectual property.

“When one person has an idea, 10 people have it at the same time. I was coming home from a business trip in Chicago, and was looking out on the side of the highway. I started thinking about autonomous delivery, and I knew they needed somewhere to go. You can’t drop them off at home. It was then where I came up with the idea for a mailbox 2.0- a charging station, facial recognition, emergency services. As soon as I got home, I ran in the house, called my patent attorney, and told him to file a full utility patent. I knew I was in a race. We ended up beating Amazon by four days and the United States Postal Service by 14. Today, I have the first positioned patent portfolio in the autonomous delivery space, with 150 total. I view us as the gateway to every single delivery channel across the world.”

O’Toole, capitalizing on his idea, knew he had to get a team behind him to expedite his vision. He began making calls, and soon had a litany of A Players at his disposal. Focusing their early efforts on marketing, investor relations, and research and development, Arrive captivated a culture of excitement and vibrancy, one that he says is unlike anything he’s ever seen in half a century of entrepreneurship.

“I use a moneyball approach. I want to get the best player, not fill any specific spot. It’s one thing to bring on specific functional people, but there are other things that have to happen. We wanted to build perception for the product first to build market awareness. We wanted something to nurse along, and wanted to drive our runway through investment. You’re shepherding a lot of the things at the same time. We hired a lot of world-class individuals early and were able to get them to buy in. If you put a team like that together, there’s nothing you can’t do. We’re executing at the highest level of any company I’ve ever seen. I’ve never seen a culture like we have at Arrive. Everyone is so eager to give back.”

This leads to a question- in a world where the mailbox has never been disrupted, what does disruption look like? To do so, O’Toole uses a phrase that I’ve never heard before- highways in the sky. To accommodate autonomous delivery, drones, and local municipalities, there needs to be something completely greenfield built out. Arrive, O’Toole proclaims, will be the one-stop-shop for all of it. 

“Anytime there’s a paradigm shift, you need to show, not tell. To get the opportunity is very difficult. Most people don’t want to embrace anything new. It’s going to require putting highways in the sky. It’s a new infrastructure. We are the next generation of what mailboxes can be. We want to make the barrier to entry really low, which is why we also want to move to a subscription model. Through the user agreement, you’ll be allowing that infrastructure we want to help build to take place. We want to be the air and ground traffic control for everything- we want all drivers and shippers to be welcome. You need to have a unified platform, which is what we want to be.”

O’Toole ever-spiraling vision is powered by a very logical conclusion- the Arrive ecosystem, in his mind, can transform just about everything. The functions of the Arrive mailbox, incorporating everything from basic delivery services to electric vehicle charging stations to emergency alerts to payment processing, are as wide-ranging as his imagination. In short- very wide indeed.

“The things we’re delivering are better, faster, fresher, greener, and safer. When you want to order a pizza, for example, you’d go to the Arrive.ai app, and you’ll be able to connect to Domino’s through it. You don’t have to worry about anything- someone stealing it, poisoning it, whatever. It’s going to help processing payments, doing returns, charging cars, and so many other things. We’re going to co-share costs with our neighbors, partners, and residences, particularly since there’s a lack of chargers in America right now. We have facial recognition for pets and Amber Alerts. Eventually, all of your commerce and so much of day-to-day life is going to run through the Arrive ecosystem. The use cases are endless.”

But, when I met O’Toole for the first time, Arrive.ai went by a different name- DroneDek. The name, while initially popular, needed a change as O’Toole’s vision expanded. This was primarily to serve two purposes. First, Arrive wanted to be more than just a mailbox- they wanted to be a platform. Second, with the AI boom in full swing, the Arrive team viewed it as too big of an opportunity to pass up. 

“When we had the idea, drone delivery was in its infancy, and we quickly realized we wanted to be less tethered to drones and become more aspirational. We wanted to showcase the paradigm we’re at. As we look to go public on the NASDAQ this year, we wanted something to better show the value of what we built. Big Data was, and is, half of the revenue streams we forecasted. We didn’t anticipate how receptive the market was going to be. We can foresee Arrive.ai being the biggest data point in the world. Our total addressable market is 160 million addresses. There’s not a bigger data set out there than what we have. When we figured out the world cared as much as we did, we made the decision to pivot.”

All of this leads to a question I’ve been begging to ask O’Toole for years- why? Why is he still so driven? Why does he still work so hard? Why does he put himself through something as wild as what he’s trying to accomplish with Arrive.ai? The answer? He believes he still has things to do. He believes that, if Arrive.ai is successful, the world will be forever changed- and for the better. 

“I haven’t done what I’ve set out to do yet. I don’t know what that means, but I know that I’m not done. I’ve seen people work their asses off, save all their money, live very conservative, retire, and die. I’m a huge risk taker- I gamble, I collect cars, and I have a lot of fun. I fuel that by working hard and having great outcomes. I want to do something meaningful in my life and give something to my kids. I didn’t have that when I was young. I’ve tried to share all of those things with my kids. They’re so grounded, so you’ll never know- I’m really proud of how humble they are. We’re having a lot of fun, but there’s a lot of work to be done. You can only sit around, watch TV, and travel so much. To be engaged at the helm of something gives me a lot of satisfaction. We’re changing the world.”

The biggest box left to check to make sure this happens for the Arrive.ai team is their biggest gambit yet- going public on the NASDAQ. Having run several immensely-successful crowdfunding campaigns that have raised over $11 million, O’Toole knows that the access to the premier capital markets around the world will be the jetfuel needed to propel his biggest hope- paying back those who invested in him. 

“We’re going to be on the NASDAQ in Q4. We’re working with the SEC, and we’re close to transacting several deals. Everything happens the way it should. We’re not going to have a partner- we’re going to list ourselves. We need access to the capital and public markets because our plan is very aspirational- you can’t do it small. I have a duty to every shareholder who puts any amount of money in this company. Our first investor came in at a $58 million valuation, and now we’re valued at $360 million. The promise of investing is liquidity, and we want to monetize it by getting access to the markets. I want everyone to have the choice to stay or go, but I want to build something massive.”

My final question, the one I ask each of my guests, is one I’m particularly curious to get O’Toole’s take on- in a world in which he has created so much value, what does he value the most? He doesn’t hesitate on the answer. O’Toole is two things- a builder, and a team builder. He likes to build things, and he likes to build things with people. It is what has defined his life, and what he wants his legacy to be defined by.

“I value what we’re building and the people that are building it with me. If you’re the smartest guy in the room, that’s no fun. The real, true, collaborative vision of what we’re building here and to have people be invested is what it’s about. I call us a ‘We the People’ story. We beat Amazon. We’re the small guy that’s got the biggest opportunity in front of us. I’m so proud that God gave me this idea. The name Arrive is mentioned thousands of times all over the world. We have 5,000 investors, and have been mentioned in every major publication all over the world. People I haven’t talked to in 40 years call me all the time and ask to invest. It’s so gratifying when people put their risk in me. I can’t tell you how touching that is, and that’s why I work so hard every day to prove them right.”

Steve Jobs once said that the crazy ones are those who end up changing the world. Many times in my relationship with Dan O’Toole, I’ve thought that he was crazy. However, I also believe that O’Toole may be right. He may be on the cusp of something great. He may be the person who completely upends a space that has never been disrupted. He may be crazy. But he also might be right. This is something that we should consider far more often than we do.

Because, if we have learned anything, we doubt the crazy ones at our own peril.

Own the Day,

Sam