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Tom Sailors
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Career Info

Primary Industry:
Apparel & Fashion, Retail
Personal Career Headline:

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Career Snapshot:

Tom Sailors is a father of four and entrepreneur from Omaha, Nebraska. Together with his wife, Tracy, they have created, built and sold six e-commerce businesses in 15 years, with products ranging from baby hats to boot socks to mushrooms. Starting in November ’16, he helped run Mermaid Pillow Co, an e-commerce store that has exceeded $10 million in revenue and 100,000 customers in its first year of business. Despite being born and raised in Nebraska, he knows nothing about farm animals, but in recent months has been required to learn about goats and cows, after moving to an acreage outside Omaha, where his daughters have become passionate about 4-H and raising animals. While he loves creating and running businesses, Tom is most fulfilled when he’s with his family, and most proud of the life he’s created that blends the two.

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What do you do best?:

Problem solving. And the more pressure, the higher the stakes, the better. My best ideas and insights, I think, have come when we have a problem, it has a deadline, and there seems to be no good solutions. I tend to thrive in those situations.

What makes you the best version of yourself?:

When I feel fulfilled. And I feel most fulfilled in the moments spent with family, where I am able to be present without fighting the urge to think about something else, like work. It’s those moments with family when I see the best version of myself, and the person I want to be. Second to family is helping others, particularly in business, I like meeting and helping other entrepreneurs work on their products and businesses, when I can. That’s when I feel most fulfilled and am happiest.

What are your aspirations? (Personal and Business):

I just want to keep growing. Keep learning. Keep getting better. I read constantly, listen to podcasts, and try to hang around people that have a similar mindset. But more specifically, what I’ve been working on for over a year is just being more present and aware. Especially with my family. When I’m talking to a stranger or someone in business, it’s easy to give them my undivided attention. But at home, when it’s most important, it seems easier to drift away thinking about work while your kids are trying to tell you about their day at school. It stings even saying that, but it’s something I’ve been actively working on improving everyday, and what I suppose I’m aspiring to: to be in the moment, to be present, to be aware.

Biggest Success?:

Overall, the life we’ve created together with my wife and four kids: (9), (7), (3) and (3). And that involves building a specific type of business (ours is e-commerce) where we can, to an extent, set our own schedules and goals, and structure it in a way that compliments the schedules and goals of our family. But an even bigger success, I think, is including our kids in our businesses to the extend that they’re interested in learning about them. I think it’s influenced them and given them a better sense of what’s possible in life and business, and I hope given them confidence to someday go out and do their own thing, make their own way.

Most Challenging Moment?:

When we sold one of our businesses in 2009, a condition of the sale was that I stay with the company for six months following the sale. I knew it would be hard for me, but it was a low point for me personally. I hate to even say that, because others have faced real challenges, me included, but for me it was a daily mental and emotional challenge.  I went from doing my own thing, suddenly having a boss, tasks, schedule and meetings.  It was a good company, and I enjoyed the people, but I hated every second of it. But I learned so much about myself during that time, specifically, it revealed how much of my own self-worth and self-image was tied up in our business, and that wasn’t all that healthy.


In business, I’ve always liked Facebook’s “Move Fast and Break Things,” and I’ve taken this approach to most of our products and businesses. But it’s funny, that motto worked so much better when I was younger and had less responsibility, less demands on my time — because when your time becomes compressed, you need faster wins. I’m working 30% of what I worked 4 years ago before my twin boys were born. Yes, I can still move fast and break things, but when life gets more complex, I find that I personally have less time to experiment and break things, and sometimes I’ll need to end the experiment early, and choose a safer approach, since I have more responsibilities now than I once did.

Favorite People/Role Models?:

Countless people that have helped me in one way or another. Too hard for me to point out just a few of them, and most of the names you wouldn’t recognize; they’re people like me, usually in my space (e-commerce), and we usually have a similar approach to life. It’s those people I like to hang around and learn from.

Favorite Places/Destinations?:

Last month, we went to Colorado and camped. Well, the friends we went with actually did the camping… we just hung out at their campsite and later when to a hotel. But that experience was my favorite in recent memory — hanging out in the middle of nowhere, family, conversation, surrounded by nature, and maybe most importantly, no distractions — made for an experience I’ll cherish forever.

Favorite Products/Objects?:

Wireless headphones. I like to walk the dog after the kids go to bed and listen to podcasts. I’ve been doing this for a couple years and it’s one of my favorite parts of the day. Wireless headphones are good for that.

Current Passions?:

It changes week-to-week and is usually based on what I’m reading or listening to at the moment. Right now it’s intermittent fasting and mindfulness. But I have lot of things that I get really energized about for weeks or months, they run their course, and then I’m onto the next. But some things stick. I like it that way.

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