Steven Sashen

Steven Sashen is a serial entrepreneur who has never had a job, a former professional stand up comic and award-winning screenwriter, and a competitive sprinter — one of the fastest men over 60 in the country (maybe the 2nd fastest 60+ Jew in the world!). He and his wife, Lena Phoenix, co-founded the footwear company Xero Shoes, creating “a MOVEMENT movement” which has helped almost a million people Live Life Feet First with happy, healthy, strong feet in addictively comfortable footwear. Steven and Lena also appeared on Shark Tank, where they turned down a $400,000 offer from Kevin O’Leary.

Where did the idea for Xero Shoes come from?

Fifteen years ago, when I was 45, I got back into sprinting after a 30 year break… and I spent the next 2 years getting injured almost constantly.
A friend suggested I get out of my “normal” running shoes – with arch support, padding, an elevated heel, and pointy toe boxes – and see what I learned from running in bare feet.

Now I’m not suggesting anyone run barefoot, but it changed my life. I discovered that I had a form problem that I couldn’t feel in regular shoes. And, more, the feedback I got from having my feet feel thou ground allowed me to naturally and effortlessly change my gait… which made my injuries go away and made me faster (I’m a Masters All-American sprinter now – one of the fastest guys in my age group in the country).

I wanted that “natural movement” experience all the time, but going barefoot everywhere wasn’t a good option (not even in hippy-dippy Boulder, Colorado), so I made a pair of minimalist sandals based on a 10,000 year old design – a thin bit of rubber for a sole and some cord from Home Depot to lace them on.

Other runners asked for their own pairs and after I’d made 50 or so a local coach told me that if I had a website for my sandal-making hobby, he would put me in a book he was contracted to write.

So, I raced home and pitched this incredible opportunity to my wife – I’d been an Internet marketer since 1992 and had built hundreds of websites – and she told me “It’s a HORRIBLE idea. It won’t make any money. And it’s a distraction from the search engine optimization business we’re trying to start.”

I told her she was right and I wouldn’t build the site.

And then, after she went to bed, I built a website 😉

What does your typical day look like and how do you make it productive?

As is true for most outdoor-focused product company CEOs, I spend most of my day indoors in front of a computer.

I’m intimately involved with marketing, including making videos and crafting ads and exploring new avenues and platforms to advertise on, with product (I’m very “princess and the pea” so if something doesn’t feel good on my foot, we don’t sell it), and with the tech team where we look to improve and optimize everything behind the scenes of the website.

Frankly, though, I spend WAY too much time deleting irrelevant emails, and saying to people who pitch me new ways to advertise, “How quickly and cheaply can I find out if you have your idea won’t work?”

In short, much of my day is putting out fires that started overnight (despite nothing having changed since yesterday), and looking for ways to grow our business.

How do you bring ideas to life?

On the product side, I work with our highly experienced team of designers and developers. We get lots of feedback from customers about the types of products they want next from us, and we have ideas about expanding and filling holes in the line.

On the marketing side, similarly, I’ve brought together an amazing team of specialists – SEO, CRO, media buying, creatives, etc. – and work with them and our VP of digital marketing to test things as quickly as possible, focusing on getting the ROAS we want.

Often, though, when an idea is making my brain explode, I just do it myself – e.g. I’ll do a video rant, throw it up on Facebook and Youtube as fast as possible. If it works, we’ll then look for a more deliberate way of crafting and distributing that content.

What’s one trend that excites you?

During the Covid lockdown, many people stopped wearing shoes and their feet changed shape and became wider after not being crammed into pointy footwear. Plus, when they started going back to work, they didn’t want the discomfort of dress shoes.

One of the design elements of our footwear is a wider, foot-shaped toe box. That, along with our shoes’ light weight and flexibility makes them so comfortable we’ve had people say they accidentally went to bed not realizing they were still wearing their Xero Shoes.

What is one habit of yours that makes you more productive as an entrepreneur?

I have no idea if I’m more or less productive than anyone else, let alone more or less productive today than I was at any time in the past.

If anything, and this isn’t a habit per se, that I’ve been a marketer for so long helps me evaluate and quickly make decisions in that sphere, and weed out things that won’t be helpful.

What advice would you give your younger self?

Get a government job with a pension. Those people get things like vacations and weekends off.

Tell us something that’s true that almost nobody agrees with you on.

“Normal” footwear CAUSES the problems that Big Shoe claims they help and cure. You do not need arch support, or padding for genuine comfort or having a healthy, strong, body… starting with your foundation, your feet.\

As an entrepreneur, what is the one thing you do over and over and recommend everyone else do?

Watch TV every night.

When I was much younger, I’d work practically 24/7/365.

It wasn’t a good idea then and definitely isn’t now.

Frankly, the only thing that keeps me from doing it is that, almost every night, my wife (and co-founder and Xero Shoes’ President) and I cuddle up on the couch with our dog, watch a movie or our latest binge-able show, and turn off our “work brains.”

It’s what keeps us sane.

Oh, and get a dog. Walking the dog every day is when I can think without interruption, and coming home after a difficult day and having a dog that is SOOOO happy to see you… it takes 2 tail wags until the day is practically forgotten.

What is one strategy that has helped you grow your business?

We have dozens, if not more… but the one that has grown our business the most is simple and can be best summed up by a line of Lena’s:

There are more than enough shoe companies in the world. We don’t need another… unless your shoes change people’s lives.

The number one strategy that has allowed Xero Shoes to keep growing, year after year, at rates that “experts” say cannot happen, is providing a quality product that improves people’s lives.

Having a genuinely valuable product is why the majority of our customers own multiple pairs of our shoes (some families own over 50), why they say they’ll never wear another brand, and why word of mouth is the number one driver of our sales.

What is one failure you had as an entrepreneur, and how did you overcome it?

“Failure” is not a word that I use to frame experiences. Every action we take is based on making what seems like the best decision at the time, given everything we know and believe. Sometimes those decisions don’t produce a desired result. Oh, well.

As a marketing-focused entrepreneur, and one who has been an Internet marketer for over 30 years, “failed” experiments are necessary. As a product-focused entrepreneur, I know that Version 1 of any product will have some number of issues and some really good products will simply not sell well.

These are all just par for the course. The way I handle them is a 2 step process:
1) Whine and mope for some amount of time – 1 minute to 1 day, depending on the issue.
2) Come up with a creative solution, if one seems possible, or just move on to what’s next.

What is one business idea that you’re willing to give away to our readers?

Vitamin-infused high-quality chocolate

What is the best $100 you recently spent? What and why?

I bought a Misen Santoku-style kitchen knife.

I’m a cook, and good tools make all the difference. Every time I use this knife, I love how it feels and how well it works. I enjoy it so much that I’ll spend extra time using it to prep vegetables, instead of using the much-faster mandoline (that I also love).

What is one piece of software or a web service that helps you be productive?

Boomerang for Gmail. The feature I use the most lets me set reminders to follow up on an email I’ve sent if I haven’t gotten a reply in some amount of time.

What is the one book that you recommend our community should read and why?

Stumbling On Happiness by Daniel Gilbert (you can also watch his TED talk). In short, many people pursue entrepreneurship because they imagine an end result that, when they achieve it, will make them happy.

Gilbert’s book points out that humans are HORRIBLE at predicting whether some imagined future will, in fact, make us happy (and also bad at guessing how present unhappiness will feel in the future). The only thing we’re worse at than predicting the future is remembering how bad we are it! And, we think we’re special – if we found a million people who achieved the goal we think will make us happy, and discover that those people are not living the dream life we imagine… we still think, “Yeah, but if *I* get there, *I’ll* be happy. I don’t care if lottery winners are no happier after 2 years than they were before winning… if *I* win…”

The more you take in this lesson, the less you’ll be blinded by the “I’ll be happy when…” thoughts, which could keep you from making decisions based on this inaccurate idea which, often, lead to the kinds of behaviors that kill many businesses (e.g. overextending financially, ignoring negative feedback, not seeing changes in markets, etc.).

Now, that said, anyone who says “Money can’t buy happiness” hasn’t driven my car. It’s not an expensive or fancy car (it’s a Subaru BRZ with a supercharger I added), but I LOVE how it looks and how it drives. I’m so grateful to have that enjoyment at least twice a day.

What is your favorite quote?

“As my father used to say, ‘Even a picnic is no picnic’.” – Larry David (from his stand-up in the 80s)

Key Learnings:

• Living your business 24/7 is no way to live (but that doesn’t mean “work-life balance” is a real thing)
• Making money is simple: find a way to improve people’s lives, even just a bit, and let them pay you to enjoy your offering
• Your expectations about the future can blind you to the best actions to take today