Climbing Mount Kilimanjaro, rafting on the Zambezi River, bungee jumping off the Victoria Falls Bridge, going on walking safaris outside Durban, scuba diving in Australia, winning a shark fishing tournament in Montauk in New York, backcountry snowboarding in Japan, living in a Buddhist temple, hiking the High Atlas Mountains in Morocco, and having Shamanic experiences in Machu Picchu, Peru are just a few of the experiences Dave Williams has had during his travels to more than 50 countries.
In between all his trips and adventures, he managed to co-found 360i, one of the first and largest search marketing companies in the ad tech industry, founded BLiNQ Media, which signed one of the first ad API partnership deals with Facebook, won a lifetime achievement award, appeared on Bloomberg TV, and co-founded NomadX, a community-oriented platform for digital nomads, with his wife Jen.
He’s also thrown and enjoyed parties all over the world and was part owner of Opera Nightclub in Atlanta, which was one of the “top 10” nightclubs in the United States. And I know for a fact that Dave and Jen are the life of any party—in no small part due to their endearing authenticity, contagious enthusiasm, sharp wit, and unique sense of humor.
To me, Dave, a current partner and former CEO of NomadX, is like a great book worth reading over and over again. I’ve interviewed him more times than any other person in my career. But no matter how many times I talk to him, I always take away something new, fascinating, and inspiring.
Dave, always generous with his time and advice, graciously answered my 70 questions, which opened another page in the book of his life for me that surprised, delighted, impressed, moved, inspired, and also enlightened me.
Our conversation ranged from digital nomads, the secret to a loving relationship, the “weirdest” food he’s ever tasted, the book every entrepreneur should read, tips for a successful business exit, how to throw fun parties, handling negative criticism, investment advice, and what he’s most looking forward to in the second “half-century” of his life. Let’s dive in!
1- Dave, I know you as a “charismatic” person. Is charisma innate or can it be learned? If it can be learned, how do you think we can develop it?
I think if you’re passionate about what you do, you bring the energy and charisma along with it. People like to work with those who have a love for their business and want to help others.
2- Which is more important? The entrepreneur or the idea?
It’s all about the entrepreneur, timing, and alignment. The idea is important, but without the right team and founder alignment, the idea won’t be realized.
3- “Find a job you enjoy doing, and you will never have to work a day in your life.” Your thoughts?
I think it’s most important to find your niche and build your career ideally around an entrepreneurial venture. A job is only where you get paid to work and can have limited fulfillment. As an entrepreneur, there’s no guarantee of success, but it allows you to create the business and job of your dreams.
4- The biggest difference between American and European investors?
America is the Mecca for entrepreneurship, investment, and innovation. In Europe, they’re held back by the culture, diversity of each country, employment laws, and mindset, but things are starting to change, especially over the past decade.
5- Digital nomads?
The modern hippy with a smartphone living and working throughout the world while traveling slowly to maximize their local experiences.
6- Digital nomadism. Who ISN’T it for?
For those that don’t like to travel, loneliness, or to be unsettled.
7- The biggest misconceptions about digital nomads?
That they are young stinky backpackers who are on a joy ride. They are mostly professionals, singles, dating, and even married between the ages of 25-55, and pretty evenly split male and female from around the world.
They are very responsible and make great guests as they are truly global citizens of the world with many interesting experiences.
They generally don’t drink in excess or do drugs, but prefer yoga, meditation, hiking, networking, and outdoor events.
Mostly, they are independent workers and others with their own companies that they run, but now post-pandemic, many more of them are remote workers for corporations.
8- Which path do you recommend early-stage startups take? Bootstrapping or funding? Why?
Bootstrapping is the best way to get started, scale, grow through reinvestment, and then exit on your own terms. Or if the idea is really big, then an Angel or VC investment should be considered. But this path will significantly limit your freedom and autonomy as the founder as then you’ll be accountable to a board and investors.
9- The best time to seek outside investment?
Once you’ve achieved market fit and have a scalable business model so the money isn’t wasted.
10- The money advice you’ve benefited from the most?
Invest in yourself and, as the founder, you’re the last one to get paid.
11- The one book every entrepreneur should read?
“How to Win Friends and Influence People” by Dale Carnegie is a classic must-read.
12- You recently sent out an anonymous 360Reach Personal Brand Survey to people who know you, saying that it’ll give you “valuable information about how I am perceived externally.” One of the questions was something like: “What’s Dave’s biggest weak point?” Not many people, myself included, have the courage or humility to ask such questions. Why made you do that?
I wanted to know how I’m perceived by my personal and professional network to make improvements and find insights into strengths and weaknesses I might not have identified on my own. It was a very valuable exercise as I look to reinvent myself and double down on my biggest strengths and identify perceived weaknesses to turn them into strengths. This survey was conducted by one of my close friends and mentees Claudia Miclaus.
13- The most interesting thing you learned about yourself from the survey?
I found it interesting that “truth-teller”, “giver”, and “philanthropist” came up in the results as I think I must just take these personality traits for granted. Now I know that people see this in me which I hadn’t considered before. The top survey results across my network, in descending order, were:
- Thrill Seeker
- Philanthropist, World Citizen
14- The biggest change you decided to make after reading the survey responses?
I’m thinking about how to turn perceived weaknesses into strengths as some of the weaknesses were due to my interest in moving very fast and always adjusting to find market fit, and sometimes being too nice and transparent. Also, I found it interesting that people saw my trusting, giving, and generosity as potential weaknesses as I see these as strengths.
15- In the survey, you asked what kitchen appliance and car you could be compared to and why. What kitchen appliance and car do you compare yourself to and why?
As a car, I like to think of myself as the Tesla Roadster as it’s innovative, fast, and ahead of the competition. I had the opportunity to drive one of the first Roadsters in the summer of 2009 and it blew my mind how fast, innovative, and quiet it was.
As a kitchen appliance, I like to think of myself as a blender as I like to mix things up but in the end it always turns out good and can be the start of a fun party!
16- You and your wife have been together for a very long time. What do you think is the secret to a healthy, loving relationship?
Find someone that complements your strengths and weaknesses. For example, my wife is very organized whereas I like to move fast and focus on the big picture so we work well together. She also grew up in an entrepreneurial family so she can understand and accept my crazy entrepreneurial adventures. It’s also important to find a partner who never gives up even when things get tough, plus who wants to share in passions and new adventures and experiences so as to always be growing together instead of apart.
17- Something you could only learn from your wife?
A passion for adventure, travel, and fierce independence.
18- One thing your wife thinks you’re not good at?
Laundry and packing as she loves packing and planning for adventures. I live with very few clothes as they are always clean.
19- I’d describe your wife as a “sweet person with a lively inner child.” How would you describe her?
My soulmate for life. Fiercely independent, global explorer, adventurer, life of the party, and extremely social who has friends for life all over the world.
20- What are you most proud of in your life?
I’m most proud of finding a connection to the natural world and living a truly global lifestyle. I’m also very humbled by being awarded the Alumni Entrepreneur of the Year at the Goizueta (Emory) graduate business school back in 2011. I’m also quite proud of global adventures I’ve done with my wife such as rafting the Zambezi, pilgrimages on the Camino de Santiago and to Machu Picchu, hiking the Tour du Mont Blanc, and climbing Kilimanjaro. My ultimate goal is to visit the moon and be alive when we discover other planetary life.
21- What do you like least about today’s digital world?
It’s too much in the cloud and doesn’t always feel real. Not enough in-person interactions and inspirations. Having said this, I’m very excited for this next evolution of the Internet with Web3, blockchain, digital assets, etc.
Our next generation web browser offering a view into everything Web3 and beyond. It’s an exciting time to be alive as it will continue to make the world a smaller and more connected place.
23- Three characteristics of a good business idea?
Alignment with the founders, niche opportunity where you can be #1, and good timing.
24- Your favorite productivity hack?
In-person retreats and meetings to build team alignment and connection to plan future quarters and, most importantly, to have fun!
25- A networking tip that works for everyone?
Always arrive early to events to more easily meet those who also arrive early, help the organizers, and act like the event is yours. Ideally take out the VIP connections afterwards for drinks or for an executive lunch meeting over the next couple weeks. The best networking is to create your own event, which I really enjoy doing as a way to give back.
26- How do you handle negative criticism and comments?
I try to use it to improve but not take it too seriously as there are too many keyboard warriors and some people are just a**holes. Nothing you can do to please everyone sometimes, unfortunately as hard as you might try.
It’s a goal of mine to become a much better surfer. I love the sport. Big boards, small waves! I think it’s such a cool sport and have a lot of respect for the big wave surfers (modern day gladiators) as I rode a jet ski at Nazare with Portuguese big wave surf legend Hugo Vau on a 60-foot wave.
29- What do you think your gift is?
To be able to envision the future and understand how I can best play a role in it.
30- Your favorite quote?
“The best plan is no plan.”
31- A good travel tip?
Go to a place where you are most passionate about and make the focus of the trip to do something adventurous and out of your comfort zone. You should always be pushing your boundaries and get comfortable being uncomfortable. This will help you succeed as an entrepreneur and in life.
32- You’ve won many awards in your career. Which one do you remember most fondly? And why?
I won the Lifetime Achievement Award from the Technology Association of Georgia in 2011, as this was very unexpected and much appreciated. It really was the icing on the cake for me professionally.
33- You’ve organized and hosted so many events and parties. What makes an enjoyable and successful event?
The venue, music, atmosphere, and making sure it’s got lots of energy and a great mix of guests.
34- The “weirdest” food you’ve ever tried? Where did you try it?
I drank the blood and swallowed the liver and beating heart of a live cobra and then ate the meat in a soup and salad in Vietnam. I ordered the house specialty and this is what I got. The cobra was brought out live and then they proceeded to cut its head off and drain the blood into my wine glass. Then they pulled out the liver and beating heart, which I swallowed and chased with the Cobra blood. Little did I know it’s a common aphrodisiac. YOLO!
Dave Williams and his wife with a group of friends in Chamonix, France (Photo: Supplied)
35- You advise early-stage startups that want to grow. What kind of companies/entrepreneurs do you like to advise the most?
I like to work with young, impressionable entrepreneurs to help them push their boundaries and to be irreverent. I know how hard it is to start a company so it’s fun for me to help the next generation, but the business has to be a strong cultural and business fit for me.
36- A must-know for first-time digital nomads?
Try it for one month. Then go home and set the future plan to live the lifestyle. And, go to a location that has a strong community or somewhere that you’re passionate about. I might be a bit biased, but I’d suggest checking out Madeira Island first as it’s NomadX’s top digital nomad community globally.
37- A new skill you learned recently?
I’ve been playing a lot of golf in my downtime as I just recently recovered from knee surgery. I’ve been playing against the British, Scottish, and Irish retirees and having fun playing it competitively.
38- A new skill you’d like to develop?
My main goal is to become a strong surfer now that I’m recovered.
39- What would you like to incorporate into your daily routine?
Morning meditation before sunrise, yoga, boxing, paddle boarding, padel tennis, and more hiking. There’s not enough time in the day.
40- A habit you’d like to eliminate from your daily routine?
Zoom calls. Lol!
41- The best piece of leadership advice you’ve ever received?
Join and run an industry organization that you are most passionate about to give back to your industry.
42- You had a stint as a college professor. What was that experience like?
I enjoyed it, but it wasn’t for me as my wife and I liked spending too much time with the students at their social events, which wasn’t acceptable by the university. I loved the experience and built great connections, but it was too conservative for me.
43- The future of universities?
On- and offline global learning platforms with more hands-on, real-world, and global experiences.
44- The best way to get PR hits?
Be a friendly resource to journalists and offer them early insights into your business and industry. Always follow up quickly when they contact you, otherwise you’ll miss the opportunity.
Is the future of the world! Can’t wait to see what’s going to happen next as it’s still early days.
46- What are you most grateful for in life?
My family has had a big influence on me and always has been supportive of allowing me to pursue my dreams. I’m also grateful for all of my global experiences and connections along the way.
47- An interesting startup you’ve invested in over the last five years (not founded by you) that we should follow?
PrizePicks Daily Fantasy Sports. It’s a rocket ship! I was an Angel investor and advisor to the business from the very beginning. I think soon they will be a unicorn and they have an amazing team, culture, and CEO. They’ve won top national awards in the fantasy sports industry and have been awarded as a top place to work and as a fastest growing company. The growth is incredible. I’ve never seen a company grow so fast!
48- What do you wish more people knew about you?
I’m very humble and just a very normal person who works hard to achieve his dreams in life and business. I’m not money-oriented, but I do see it as a way to measure success in business. I love simplicity. The world is becoming too complex, so I need to work hard to keep things as simple as possible. Simplicity is the key to happiness.
49- The country at the top of your travel list?
Japan although I’ve already been there several times. I’d love to live there sometime in the future after Portugal.
50- The most valuable business lesson you’ve ever learned?
Follow your instincts and don’t second-guess yourself.
51- How would you describe your bungee jumping experience?
52- The next adventure you’re looking forward to?
Snowboarding in Chamonix, France, this winter and heli boarding for my wife’s birthday in Courmayeur, Italy.
53- The soft skills that have helped you the most in your personal and professional life?
Empathy, being nice, giving, and caring as a mentor for the next generation.
54- Pitching to journalists. How can founders get it right?
Offer them value first. And know how your business relates to them and can help them.
55- If you could relive one week, day, hour, or minute of your life, which would it be?
Where I’ve made my biggest mistakes or lost my temper. I’d go back and take the high road, take more time, and just let go of it although it’s hard as my strong passion and drive can get in the way.
56- The best country for digital nomads?
Portugal is #1 in the world and continues to get better every year.
57- The top three things you consider when making investment decisions?
Founder fit, timing, and valuation, but at the end of the day, it’s all about the entrepreneur.
58- How important is the role of a business/personal coach in the life of an entrepreneur?
It can be very helpful, especially if you’re a remote worker. It’s interesting as a couple decades ago, life coaches weren’t a thing, but I think now they are very valuable, especially if you are experiencing hardships or going through difficult periods in life and business. I’ve worked with life coach Nyah Pham and experienced great results. But at the end of the day, it all comes down to you as they can’t do the work for you.
59- How do you stay inspired and eager for more despite all your professional successes?
I find inspiration by disconnecting and going on global adventures in nature, especially on long distance hikes, as it gives me time to decompress and think more clearly and creatively. When at work, I get inspiration by connecting with my teammates in person, advising young entrepreneurs, and going to global conferences to share ideas with my industry peers.
60- Coca-Cola or Pepsi?
Coca-Cola. I’m from Atlanta, which is where it was founded. Plus, it just tastes better, and I love the brand.
SpaceX is my favorite.
62- You’ve had several successful business exits. What’s your top tip for a successful exit?
Timing and building a strong relationship with the acquirer and using a strong investment and legal firm to help with the process. And, it’s very important to have your legal, technology, and accounting records in excellent shape for due diligence as if the records and code aren’t good, you will lose the deal or get a reduced valuation.
63- Top qualities to look for in a business partner?
Strong entrepreneurship drive, personal connection, complementary skills, and business ethics. A business partnership is more challenging than marriage so it’s important to find the right partner as most business partnerships fail.
64- Your next startup, if you ever launch one?
I don’t plan to launch any more startups as I feel that I’m past this stage in my career of founding and running companies over the past 25 years. It’s very hard work. Now, I’m most happy to advise future generations of entrepreneurs from the outside versus being on the inside.
Super important for digital nomads, remote workers, and the industry’s growth and development.
66- As far as I know, 360i is a brand you’re still in love with, and you wrote a heartfelt message after it was announced that the name would no longer exist. When you look back, what was the best thing about 360i? What did the name mean to you then and what does it mean now?
360i became the #1 search engine marketing, performance marketing, and digital agency in the U.S. It was the first big business I started in 1998 and so I have a deep connection and love for the brand and the dot-com startup journey. We were one of the first agencies to buy ads on Google and won their Marketing Machine Award as their #1 U.S. Partner in 2007. The agency now has over 1,000 employees and manages over $2 billion in advertising. The brand was recently merged with Dentsu Creative global holding company.
67- The best thing you learned in the first “half-century” of your life (as you call it yourself)?
Move fast and work with people who share your passions. Nothing can substitute hard work and hyperfocus. Take time away from work to rejuvenate and see if the business can run without you as that’s when you’ve created the most value when the business isn’t reliant on you.
68- What are you most looking forward to in the second “half-century” of your life?
Travel, adventures, advisory work, and meeting new people from all over the world.
The #1 brand for digital nomad communities in amazing remote locations throughout the world. Super fast wifi, cowork, community management, and lots of events everyday. At the moment, we are on Madeira Islands, Cape Verde Islands, Costa Caparica, Lisbon, and soon launching in Pipa, Brazil, on November 1, 2022. Those interested can join our nomad community by visiting our website.
70- Dave Williams?
Thrill-seeking digital entrepreneur with a strong vision for the future and still with a lot to give back to the world.
Any parting thoughts, Dave?
Don’t try to be perfect. Move fast. Focus on a niche that you can own. Have fun and focus on winning!
Author bio: Elham P.Mohammadi is a journalist and the founder of ElhamX Media.