The Smarter Startup

Startup Lessons Learned from 50 Days Skiing (During the COVID Winter)

I would work with startups all day before sneaking away for an hour or two on the slopes.

This ski season I decided to turn COVID into a once-in-a-lifetime opportunity. I packed up my family on January 4th and moved them to Northstar Mountain in Tahoe. I told anyone who would listen that I was going to get 50 days of skiing in this ski season. Little did I know how difficult it was going to be. Not physically, but mentally.

I would work with startups all day before sneaking away for an hour or two on the slopes. Halfway through the season, I started thinking of lessons I was learning that directly applied to startups. At first, I was doing it as a lark, but the more I got into it, the more it started to resonate with me.

Invest in your Team

My Lesson: On the first day out with my daughter I was really nervous, because even though she had been skiing for four years, she really wasn’t that good. If she decided she was done with skiing, we would all have been miserable. Instead of leaving it to chance, we brought in the professionals. We invested in her, putting her on the midweek and the weekend ski team. She got mentoring 4 days a week for 12 straight weeks. By the end of the season, my eight-year-old daughter was skiing the bowls of Kirkwood with me. An amazing return on investment.

Startup Lesson: Startups are often short-sighted and fail to invest in their people. It may be hard to measure the investment, but it is cheaper to train up your existing team and build a strong culture than it is to bring in new guns for hire when you are still figuring it out. Burkland works with a company called Experiential Insight that can help you make sure your training dollars have impact.

Stretch Goals Motivate

My Lesson: There is no way I would have made 50 days (actually 51) if I did not set it as my goal. There were days that I had no desire to suit up and hit the slopes, but I had to, or I would not reach my publicly stated goal. I probably would have gotten in 40 days. The stretch goal increased my performance by roughly 25%.

Startup Lesson: Salespeople often feel the same way. Without quotas, spiffs, and quarterly targets, there is little way to motivate salespeople. The same goes for engineers with roadmaps and Management with ARR. Figure out what your key metrics are and get your organization focused on them and rewarded for achieving milestones along the way. Make sure the road you’re traveling on is fun.

Learn from your advisors on the way up

My Lesson: Some of the best conversations and networking I have done in the past year have been on chairlift rides up the mountain.

Startup Lesson: It is so much easier to get advice on the way up. Savvy founders realize they can talk to almost anyone when they are just starting out. Successful people love to share their wisdom with startup founders. It makes them all warm inside like a well-earned mug of hot chocolate.

Share your progress with others along the way

My Lesson: As I hit milestones along the way, I shared my progress on Facebook. When I fell into a rough patch and had not skied for a few days, I would share a Facebook post and get violins and boo whoos in return. It helped me realize how lucky I was and to embrace and enjoy the moment.

Startup Lesson: Keep your existing and potential investors informed as the business progresses. VC’s will be more vested in you and your company if they see your progress along the journey. Remember VCs are investing in you as much as your business.

Be Humble

My Lesson: I thought 50 days skiing in one season was a big deal, and I kind of made a big deal about it. One day on the lift up I mentioned to the retiree next to me that today I had reach my goal of 50 days. His matter-of-fact response was “Keep it up, I have already skied my age this year and I’m 85. Hope to hit a century again this year.”

Startup Lesson: You may think your business is going gangbuster, but there is always someone doing better, a founder that has already had multiple successful exits, a VC with multiple unicorns. When meeting fellow founders or investors, be humble, and people will appreciate your accomplishments so much more.

A singular focus can be detrimental to long term wellbeing

My Lesson: I love to ski, but 50 days in one year is more than I need to be happy. I typically get out 15-20 days a year, and I will go “Hard” on those days. Living on the mountain turned my typical day into two hours, and as soon as I saw a lift line, I was out of there. During those three months, I also did not do my other favorite activities (tennis, hiking, biking etc.) This winter’s lifestyle was not well rounded, and it was not sustainable for me or my family.

Startup Lesson: I have seen too many companies focus on one or two big-name company prospects. They think “if I have those logos, the next funding round will be easy”. They jump through hoops, make feature changes, and dedicate unfathomable engineering resources to try and make these logos happy. This is often to the detriment of the core product.

They may even land a whale, but it was not easy, and it usually is not healthy for the company. A scalable business is not one or two customers. It is usually better to build a strong, diversified sales pipeline. Listen to your customers and figure out how to scale before the next raise.

Hope to see you on the slopes next season, or better yet, hope to talk with you on the lift ride up or on Zoom.

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