A cyclist (not the author – not yet anyway) tackles the Italian Alps

CREDIT: Getty Images

I’ve been writing about business and entrepreneurs for over two decades and have had the great pleasure of watching, up close, how startup founders think, tackle challenges, and overcome obstacles. It’s a damn good thing, too, because I am about to embark on my own “launch,” a challenge that is so audacious, so daunting, with odds stacked so high against success that it looks a lot like starting a business.

I recently accepted an invitation to an all-expense-paid, three-day cycling trip in the Italian Alps with Gary Erickson, founder of Clif Bar, his wife Kit Crawford and members of the Clif Bar team. The trip, in June 2017, is to celebrate the company’s 25th anniversary. Mileage will average 120km a day (cycling distances and elevations are always expressed in kilometers – see Velominati Rule #24). The climbs – which will include the Passo di Gavia, one of the most epic climbs in Italy – will be steep and endless.

Erickson has been doing bike trips in the Italian Alps for most of his life. Although I’ve cycle toured all over the world since I was 10, I have never cycled up an Alp, Italian or otherwise. To say I’m scared sh*tless is an Alp-sized understatement.

Why did I say yes to this invitation when it’s obvious to anyone who has read this far that I am probably destined for failure? Because as I approach deepest, darkest middle age, I need to try something that at first, second, and third glance seems impossible. It may soon prove to be. But until that day, I’m giving it my best shot.

This is where the founders come in. They achieve the impossible all the time. And many of the strategies these top founders use to succeed have become surprisingly relevant and inspiring to me as I train for Mission Highly Improbable.


My favorite bit of advice on the subject of attempting things large and hard is from Barbara Corcoran: “The only way to start anything worthwhile is to stop talking about it.” I probably don’t have enough time to train as well as I should, I’m probably too old, I’m probably too fat, I’m probably not in possession of knees that will survive this feat. Corcoran says to stop analyzing, jump in, and figure it out as you go along. “Get out there and try 100 things and get over the fact that 98 of them won’t work,” she says. Done.


The consensus of most of the founders I’ve spoken with during my career is that if they’d known when they started how hard it was going to be to build a business from the ground up, they probably wouldn’t have done it. That’s why I am not researching too much about what awaits me in those mountains. I’ve studied the Gavia climb, just so I know where my fitness needs to be, which is helping me and my coach (more on her shortly) devise the proper training plan, but that’s about it. The best trips I’ve ever done on my bike happened when I had no idea what was up ahead. It forced me to be 100% present in the moment – because there was no alternative. If you think too much about that enormous challenge just around the bend, it overwhelms you and makes you want to quit. This applies to both cycling and business – and pretty much all of life.


“Great CEOs all share one trait: a willingness to be vulnerable. They’re self aware about knowing what they’re good at what they’re not good at,” says Jason Hanold, CEO of HR firm Hanold Associates, which is #3585 on the 2016 Inc. 5000.

Every founder I’ve ever interviewed agrees wholeheartedly with this sentiment. I do, too. So here it is: I am (relatively) good at following a training plan. I am very bad at creating a training plan. So I swallowed every bit of “I can do this myself” pride and, hired Kristin Phillips, co-owner of The Art of Cycling, a cycling coaching company. Phillips is a former mountain bike and road racer and has forgotten more about training than I’ll ever know. I need to be ready to climb long, sustained grades, so she’s created a training plan for me designed to build my functional threshold power – or FTP – which is the maximum amount of power (in watts) that I can sustain for a hour. We’re not focusing on speed – just power. She’s got me training mostly indoors on a trainer – which at first I thought was weird. My first inclination would be to just ride tons of outdoor miles as hard as I can. That is probably the worst way to train, Kristin says. Specifically designed and regimented workouts on an indoor trainer – where you can control and track all the variables — are the fastest, most efficient way to build my power. Thankfully, I recently purchased a smart trainer (a Wahoo Kickr), and the workout plans she’s designed are built to run on the virtual reality cycling app Zwift (which integrates with the Kickr. Zwift controls the resistance on the smart trainer so it feels like you’re actually riding up and down the hills that you see in the virtual reality world. For a screenshot, check out my Instagram feed [krisfreeze]. Membership is $10 a month. I’m currently riding out the free trial period.) At first, I was skeptical that this plan could get me ready for such an epic ride. But after two weeks, my sore (and increasingly solid) quads are telling a very different story. Swallowing my pride and asking for help was the smartest thing I could have done.


The entrepreneurial landscape is littered with the corpses of companies that expanded too quickly, tried to do too many things at once, or wanted to be all things to all customers. This is doubly true for athletes who start their training at “11.” If I came off the couch and started pushing myself as hard as possible to improve speed, power, and distance all at once, I would get hurt. I know this because that’s exactly how I trained for a big cycling event last year and I got hurt. This year, I’m doing highly focused training in small, graduated increments without exhausting or hurting myself. It feels strange pacing myself like this – I’m an “everything all the time” sort of person. But the amount of sleep I suddenly need, the amount of water I suddenly need to drink every day (think: twice what I normally drink), and the pleasant ache that has been hanging around for the last two weeks lets me know that my body is being worked hard. That nothing hurts – as in “I think I snapped something” – is a testament to this moderate approach. Wish I’d known about this 30 years ago. Yes, I’m an idiot.


“Don’t negotiate with yourself,” Tony Robbins told me in an interview last year. This is a man who plunges himself into a frigid pool of water every morning just to remind his brain who is in charge. Unlike Robbins, I negotiate with myself. Myself and I do deals every day- I’ll double up on my workout Tuesday so I can sleep in on Monday. I’ll move the weight training to Wednesday so I can meet a friend for coffee. When faced with the choice of a dry Nolet martini with a twist or tall glass of seltzer water and a lime — well, anyone who knows me knows that’s not even a negotiation. I do not trust myself to stop negotiating with myself. That’s another reason I hired Kristin. She’s watching. She’s following me on Strava, a social online platform for athletes to log their activities and support each other (My membership is $59 a year, but there is a free, less-featurey option). She knows when I’ve been bad or good or, more likely, lazy. But in the end, if I negotiate myself into missing workouts, I’m the one who will be suffering like hell in three months. I am making friends with consistency, working the plan and learning to shut down my inner haggler. It’s hard, but as any founder (or cyclist) will tell you, nothing worth having is easy.

Follow my training and my trip to the Alps on Instagram (krisfreeze) or Twitter (@Kris_Frieswick). I’m using the hashtag #MissionImprobable. My next installment of my Mission Improbable series is in two weeks.