How to Navigate a Learning Curve with Sierra Cider

An interview with David Bailey, co-owner of Sierra Cider

This week, I’m featuring my interview with David Bailey, co-owner of Sierra Cider with his partner Dana Tiel – they’ve had a big learning curve to navigate, but they’re also quickly gaining essential entrepreneurial skills. Sierra Cider is a hard cider-making orchard just outside of Yosemite National Park in Mariposa, California. 

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David and I go way back – we went to high school together and we were involved in the same extracurricular activities, like choir and musical theater.

I’ve always viewed David as someone with an adventurous side – up for something fun and different…

A brief memory comes to mind: 

One late night, after a musical rehearsal, David was kind enough to give me a ride home in his white SUV. Just before he put the car in drive, he said, in his best Sir Ian Mckellon voice, “Now, Shadofax, show us the meaning of haste!” For the uninitiated, Shadowfax is Galdalf’s horse from the Lord of the Rings. 

So, it was never out of the question for me that David would embark on some epic quest, become a Jedi Knight, or build an Interocitor… 

…but, I didn’t expect him to become a farmer. So, when I found out he and Dana bought an orchard, I had to reach out and see how it was going. 

321 Liftoff | Small Business Interview | Sierra Cider | How to Navigate A Learning Curve


When David and Dana first visited the orchard in 2021, they instantly fell in love and could easily imagine a new future there. In fact, just a few months after that visit, the orchard was theirs. Then, they quickly found themselves on a new learning curve.

Okay, so you get the keys to the orchard, what was that like? 

“It was this feeling of ‘oh my gosh, we’re going to embark on this new adventure, it’s going to be so exciting – we’ve got all these big plans and everything.’ But, we hadn’t planned on moving up to the property until the living space we wanted to remodel was ready. We were not there yet and we got a call from one of the former owners.”

“He said ‘hey, when are you guys coming out here?’ and we’re like ‘well, you know, we haven’t started construction on remodeling the living quarters up there so we don’t really have a set day when we’re going to be coming yet’ and he says ‘okay, well, you own a farm now and harvest is not over – there’s already orchard cleanup to do before winter and we’re not going to do it for you because we don’t own this farm anymore – we’ll show you how to do it, but you guys need to get out here and do the work  that you signed up to do.’ And, we realized ‘oh god, this is not really going to be on our terms’ – we own a farm now and we’ve got to go take care of it.”

321 Liftoff | Small Business Interview | Sierra Cider | How to Navigate A Learning Curve

About a week after that phone call, they packed up all their stuff, drove out to the orchard, and then bounced around between Airbnbs for four months, before buying a camper and living in it for another three months. 

In life and business, sometimes you have to recognize that what you ideally want is temporarily out of reach – that’s your cue to move forward in increments, making decisions that get you a bit closer to that vision over time. 

What was the energy like on your official Day 1?

“That first day was so unbelievably exciting. The orchard was in full blown Autumn mode and the colors were absolutely brilliant. It was so incredibly exciting. And, then the work began. There were still some apples to harvest and there was a lot of orchard cleanup to do to get it ready for winter. So, that first day was really exciting and then we got right into the work.”


When you’re starting something new, it’s hard to know exactly what you’re getting into – it’s not a lack of planning or forethought, it’s just the nature of a learning curve. By nature, they’re steep and full of surprises. 

“This farm requires so much. There were moments where we said ‘oh, we’ve definitely bitten off more than we can chew.’ Just the thought of all that we had to learn from scratch – neither of us had any agricultural experience or cider-making experience. We drank cider, but that’s about it. We went from zero to commercial cider in such a short amount of time”

How do you navigate a learning curve like that? 

“The first year, I focused on learning how to make cider taste good – and fortunately our apples do most of the heavy lifting. It’s not just an apple orchard, it’s a cider orchard. About two thirds of the apples we grow are completely inedible cider-type apples – like wine grapes, you don’t eat wine grapes and you don’t eat cider apples. So, my focus was learning how to make sure that local customers and vendors were still getting a product that was up to the same quality as the previous owners. Once I had gotten a handle on that, this second year has been about learning farming and good orcharding practices.”

Building skill takes investment – its energy and consistency over time. But, when you’re trying to build so many skills at once, energy and time are limited. The net effect of which is spreading yourself too thin to make any real progress. 

Instead, as David and Dana did here, you need to strategically overinvest your energy in one skill at a time. You’ll build momentum and strength – and from that, you’ll gain confidence. 

Yes, everything else still has to get done, but you don’t need to goal yourself to be perfect at all of it. When the learning curve is this big, you’ve got to pick your targets.

321 Liftoff | Small Business Interview | Sierra Cider | How to Navigate A Learning Curve


The approach I described above is one way to get a foothold and regain a sense of control, but often there is still a lot outside of your control.

“Even with all of that work, we got hit by a frost this year, which is something I couldn’t control. We lost about two thirds of our crop – most of the apples in California are in really bad shape this year, actually. That was another really hard lesson I learned – that’s farming, sometimes you’re going to lose your crop.”

What sort of mindset do you need to hold in order to be successful with that experience? 

“Well, for a very long time, I was really hard on myself. There’s always something going wrong or breaking – and this is just life on a farm. It took me a very long time to come to terms with that. Many farmers around here, they helped me understand that farming is maintenance and repairs – that’s just what it is. There are things you know you have to do and plan for, but more than half of it is problem solving, fixing stuff that breaks, troubleshooting – things that you can’t expect to happen.”

“At a certain point, I just started waking up and thinking ‘something’s going to go wrong today and I’m going to have to figure it out.’ As an example, last year we juiced 6 times, and we had catastrophic malfunctions 4 out of 6 times, which stopped us dead in our tracks. Those first 3 times were so unbelievably heartbreaking that, eventually, I got a little numb to it, I started expecting it, and I would go into the day with it: I’m just going to have to not flip out, not shut down, and figure out how to fix it.”

Unexpected challenges happen all the time – that’s life. Instead of hoping for everything to go right, you need to be mentally prepared for things to go wrong. 

It’s not a defeatist attitude, but a pragmatic one. This way, you know where to aim your energy when surprises happen: you can attack the problem, rather than sulk about it. 

How do you feel after you’ve solved a problem? 

“One of the things that I’ve realized too is that the satisfaction of fixing a problem grossly outweighs the friction of the problem itself. Sure, it’s terrible to realize the thing isn’t working but the satisfaction I felt when I fixed it and got it working and seeing, ‘wow it’s actually working better than the last one’ – that feeling was so much better than the anger and frustration that I felt in the first place.”

Sometimes a learning curve is trial by fire – the greatest insights come after making mistakes or having things go wrong.

The greatest teacher, failure is’ might be my favorite Yoda line of all time. If you don’t learn something from failure then you’re focusing on all the wrong things. You have to see failure as a teacher. There are times though, like last year, the motor on our apple mill just completely  burned out – there was no trouble shooting that, we tried to fix it, and then busted it open, and all of the electrical capacitors had melted. We had to order a new one from the supplier, who had to order it from the manufacturer in Austria, who had to order it from the manufacturer of the motor in Italy, so that took almost a month. Sometimes problems are big, but again we learn from them.”

Take a moment to catch your breath and feel whatever you’re feeling. Acknowledge it. Then, ask yourself: do I still want to move forward? Yes. Then, your options are to solve the problem, find a creative workaround, or change your approach. 

321 Liftoff | Small Business Interview | Sierra Cider | How to Navigate A Learning Curve


With so much to do just to keep a business running, it’s easy to lose track of how much energy you’re expending and how little energy you’re taking in. You run the risk of draining your battery faster than it can be recharged. 

In other words, burnout is always just around the corner on a learning curve – unless you find ways to make your ascent sustainable. 

What are you doing to care for yourself? 

“Sometimes Dana and I have to check in with each other. Like, ‘do you want to talk about this right now or later?’ All of October is Halloween here and we love it and we love talking about it. But, if it’s something like, ‘the Roxbury Russets are going to be ripe at the same time as  the Kingston Blacks and that’s a lot of harvesting that needs to be done with all of the other things’ – talking about all that stuff can stress us out. It’s easy to go there because it’s our life. We’re spouses and we’re business partners.” 

321 Liftoff | Small Business Interview | Sierra Cider | How to Navigate A Learning Curve

What experiments have you run to make that easier? 

“One thing that helped was setting schedules for ourselves and rules, in a strange way. For example, last year when we started doing orchard tours and tastings, we would just make it so anybody could schedule something any time – and then we realized we were working 7 days a week. So, we decided that Sunday is our day off. Sure, there are certain times of the year when we can’t, but mostly we hold ourselves to having a good time on Sunday and do something that we really enjoy.”

“The other thing was my delivery schedule. Before, if somebody called me and said ‘we need cider,’ I would jump in the car, and bring them cider. It’s a good problem to have – fortunately for us, demand for our cider has skyrocketed, all of our vendors are buying more, stores are giving us more shelf space, they’re selling out quicker. So, for a long time I was just getting where I could, and I had to stop and say: ‘okay Monday is delivery day.’ Once I started doing that, so many other things fell into place, because now I’m not guessing when I have to  go into town because Monday is the day.”

Boundaries can be misleading. On the surface, they might seem like a constraint, but they actually unlock so much freedom. 

Remember, the business you’re building is the summation of your choices. 

Through that lens, you give yourself permission to rethink any and all of it – to run experiments today that might shape a different tomorrow. 


Sierra Cider is open for business. 

I want to thank David and Dana for sharing their story. 


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Starting and growing a business is not a straight line.

It can feel messy – it zigs and zags, it starts and stops. It can feel frustrating even for the most seasoned business owners. And, that’s ok.

It’s also an exciting challenge. It’s going to stretch you. You’re going to learn a lot – not just about business, but about yourself.

And, that’s why it’s worth it.

321 Liftoff | Small Business Interview | Sierra Cider | How to Navigate A Learning Curve

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