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Ron Schneidermann: “Stay humble ”

Focus. Not just on the work, but on what drives you and your “why” — There are no highs without lows. When challenges arise, remember why you’re doing what you’re doing. Remember that if it was easy, everyone would do it. Focus on your passion — the driving force that got you to this point in the first place, […]


Focus. Not just on the work, but on what drives you and your “why” — There are no highs without lows. When challenges arise, remember why you’re doing what you’re doing. Remember that if it was easy, everyone would do it. Focus on your passion — the driving force that got you to this point in the first place, and see if you can apply the lessons you’ve learned from mastering your passion to your profession. It will always be a grind, and there will always be work to do, so prioritize and pick and choose where and how you apply your energy.


As a part of our series about entrepreneurs who transformed something they did for fun into a full-time career, I had the pleasure of interviewing Ron Schneidermann. Ron is an entrepreneur who is passionate about building great companies that help people have authentic, organic, real-world experiences. In 2005, Ron co-founded Liftopia, the global leader in ski lift ticket bookings, and most recently was Head of Growth at Yelp Reservations. Ron is committed to mentoring other entrepreneurs. He frequently advises members of the 500 Startups community, and speaks at industry and thought leadership events. Ron attended UCLA, where he earned his bachelor’s degree in Mass Communications, and lives in the East Bay, California, with his wife Jenny, their three children, and their dog Sally Toodle the Golden Doodle. Ron loves riding his mountain bike, but his all-time favorite trail is the Na Pali Coast Trail in Kauai.


Thank you so much for doing this with us! Can you tell us a bit about your “childhood backstory”?

My parents are immigrants. They came to this country with a promise of a scholarship at the University of Illinois, one suitcase, and $50. I like to think that the fearlessness that got them here is part of my DNA too. If nothing else it helps me keep things in perspective.

Some of my earliest memories are of my parents, my sister, and me piling into our baby blue station wagon and driving around the country visiting the National Parks. My dad was a geologist and his love of rocks ran deep. The backcountry was a classroom opportunity for him and we spent a ton of time together out on the trail.

Being outside in nature is something that I grew up loving, and today it’s still my favorite way to spend time with my family.

What was the catalyst from transforming your hobby or something you love into a business? Can you share the story of your “ah ha” moment with us?

When I was at UCLA in the late 90’s, I watched the tech boom take off in the Bay Area, and knew that I wanted to be a part of it. But just as I graduated, everything imploded. I ended up taking a job at a big management consulting firm. Even though I learned a ton, I was miserable, and ultimately ended up landing a job running Biz Dev at online travel company, HotWire.com. This was my first ah ha moment — realizing that not only is it possible to earn a living working on a product that I personally love to use and in a space that I’m super passionate about, but that I’m actually at my best when I’m able to do it.

My second “ah ha” moment was when I decided to go to business school to “learn entrepreneurship”. I took the GMAT and was just starting to write my application essays at the same time I co-founded Liftopia, my first startup. I figured if nothing else, Liftopia would be a cool experience to write about in my application. I never did make it to business school, but discovered something even more valuable — my second “ah ha” moment. I realized that the best way to learn something new is to just go out and do it hands-on. No matter the outcome, the experience and knowledge you gain is something you can carry with you throughout your career.

There are no shortage of good ideas out there, but people seem to struggle in taking a good idea and translating it into an actual business. How did you overcome this challenge?

Just because you have a good idea doesn’t mean it will translate to a good business. As entrepreneurs we need to make sure we are thinking about how to turn our ideas into a viable, sustainable business. That means thinking beyond just product/market fit (is this something that people are actually willing to pay for) and taking into consideration product/channel fit. Meaning, how are we going to get our product or service into the hands of paying customers, and can we do it in a way that not only are there enough paying customers, but is the spread between what we are making per customer and what we are paying to acquire each new customer enough to make it worthwhile.

What advice would you give someone who has a hobby or pastime that they absolutely love but is reluctant to do it for a living?

Assuming it’s a sound business idea and something you could make a living off of, then the only question is, “why not try?” Forget about fear of failure. That’s only your ego talking, and that voice only exists in your own head. No one who is worth building a relationship with, either personally or professionally, will fault you if things don’t work out. Plus, even if you do try and fail, you will have learned so much through the experience that the invaluable knowledge and learnings will help carry you throughout your next venture.

It’s said that the quickest way to take the fun out of doing something is to do it for a living. How do you keep from changing something you love into something you dread? How do you keep it fresh and enjoyable?

Stagnation is the enemy. Just as you challenge yourself when pursuing a passion (like finding bigger trails to explore), you’ve got to keep pushing yourself professionally. Keep up with new technologies, learn new disciplines, and keep evolving. The great thing about running your own business is that you are ultimately responsible for everything. There are no silos, which means you can go both broad and deep. If you want to learn about accounting, go do the accounting. If you want to learn about email marketing, go do the email marketing. The flip side of that coin is to recognize when it makes sense to shed tasks. If you’re getting bogged down in the weeds doing a repetitive task that can be handed off to someone else, make that move as soon as you can. You want to spend your time flying at the right altitude and focusing your efforts on the things that grow the business.

What is it that you enjoy most about running your own business? What are the downsides of running your own business? Can you share what you did to overcome these drawbacks?

To be clear, running your own business isn’t glamorous, and it isn’t for everyone. It sounds cliche, but it’s a roller coaster — the highs are really high, the lows are super low, and you need to develop thick skin quickly since everyone will have an opinion about why what you’re doing might not work. You’ll find that you can never fully be present with friends and family. I know I’m not alone when I say that there’s always a part of my brain that doesn’t turn off. When my daughter was born, I took 2 days off work. When my son was born, it was a luxury to take 5 days off. This lifestyle doesn’t just take a toll on you but also on your loved ones. But the flip side is that you are in control of your own fate. You get to be the one steering your ship, not somebody else. It’s intoxicating, and if you can stomach it, the opportunities for growth, both personal and professional, are incredible. And at the end of the day, no matter how many challenges are thrown your way, focus on the opportunity for growth, because no matter what, no one can take that away from you, and that is what helps make it all worth it.

Can you share what was the most striking difference between your actual job and how you thought the job would be?

Living in the minutia! Again, entrepreneurship isn’t as glamorous as one might think, and to be a good leader you need to be willing to roll up your sleeves and get your hands dirty. My day-to-day runs the gamut from analyzing spreadsheets, to talking with investors, doing front-line customer support, negotiating with vendors, and writing copy. I’m even the one who is usually restocking the company fridge with beers and bubbly water! I’m the catch-all backstop, and while there’s nothing glamorous about it, it’s worth it.

Has there ever been a moment when you thought to yourself “I can’t take it anymore, I’m going to get a “real” job? If so how did you overcome it?

The ‘grass is greener’ mentality is very real. I’ve spent time on both sides of the fence — both running my own company and working for others. At the end of the day, neither side is really greener — each is just a different shade of green. My buddy taught me how to apply a simple rubric to figure out when it’s time to move on — every few months I ask myself whether I’m learning new skills, whether I’m having fun in my day to day, and whether I feel like I’m compensated appropriately. As long as I can check at least two of the three boxes at any given time, I’m good. If for some reason one on none of these expectations are being met, then the opportunity cost of staying is too high and I know it’s time to move on.

Who has inspired or continues to inspire you to be a great leader? Why?

My family and kids don’t just inspire me to be a great leader, but have taught me how to be a more complete person. Every day they teach me different lessons that I take and apply to my work. My kids have given me a gift — they’ve taught me the ultimate lesson in humility — a key value at AllTrails. When I get home in the evening, my kids don’t care if I was quoted in an article. They don’t care if I’m the CMO at a company or who I got to meet that day. To them, I’m ‘Dad.’ They need me to be present, patient, and compassionate, to teach by setting a good example. These are all virtues that they’ve pushed me to cultivate, and I feel like I’m a better leader because of them.

How have you used your success to make the world a better place?

At AllTrails, one of our guiding principles is that the outdoors are for everybody, and everyone should have access to nature. As a father of three young kids, I want to make sure that the wild places that I love and that shaped who I am will still be there for them and their future children. We’re fortunate that AllTrails is in a position where we’re profitable and growing. With this stability we feel a responsibility to give back. We are proud members of 1% of the Planet, and we are working with some amazing non-profit partners who focus on increasing access for all people to the outdoors as a means of building healthy, happy, and sustainable communities.

What are your “5 Things I Wish Someone Told Me Before I Started” and why? (Please share a story or example for each.)

  1. It doesn’t happen overnight — This job isn’t glamorous, which is why it’s so important that you first and foremost are passionate about the profession. I didn’t take a salary and ate canned soup every day for 2 years while trying to get Liftopia off the ground. Two years! Success doesn’t happen overnight, it usually isn’t glamorous, but the hard work pays off.
  2. Stay humble — I’ve mentioned this, but I can’t say it enough. Be proud of your accomplishments, be confident, but maintain humility. A confident person will roll up his/her sleeves and do whatever it takes to get the job done. But an arrogant person will look down on others, expecting the work to be done without lifting a finger. Don’t be the arrogant person.
  3. Give Back — It’s so important to pay it forward. Whether it’s to your employees, a cause, the community or other young entrepreneurs, I fully recognize that I would not be in the position I am today without the guidance of others. Especially in today’s world, as consumers are having an increasingly difficult time building trust, brands have a unique opportunity to rise to the occasion and give back to important causes. Not only does this build brand loyalty, but it truly creates a stronger community and is quite simply the right thing to do.
  4. Not all of your learnings or great ideas are going to happen in front of the computer — In fact, most won’t. Go outside, hit the trail, or do whatever it is that helps you think creatively, differently, understand new perspectives, and return to work refreshed. A lot of my ideas come to me when I’m mountain biking. Identify the ways you work and think best, and fit that into your schedule so you can be as effective as possible.
  5. Focus. Not just on the work, but on what drives you and your “why” — There are no highs without lows. When challenges arise, remember why you’re doing what you’re doing. Remember that if it was easy, everyone would do it. Focus on your passion — the driving force that got you to this point in the first place, and see if you can apply the lessons you’ve learned from mastering your passion to your profession. It will always be a grind, and there will always be work to do, so prioritize and pick and choose where and how you apply your energy.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

“It is amazing how much can be accomplished if no one cares who gets the credit.” — John Wooden.

Thank you for these fantastic insights. We greatly appreciate the time you spent on this.

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