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Oh Sierra


6 Steps To Scale Your Small Business

We help creative leaders harness the potent power of community (online and IRL) with content strategy, education, and events.








Craft Your Unique Cocktail for Content That Connects.


There are so many buzzwords circling around that all hinge on the promise of a world where you can step away from the front lines of your business confidently, and everything will just work out. The business growth we hear about online is glamorous, and seemingly abundantly accessible.


Duh, we want that.

But, as self-employed entrepreneurs, there are MANY limiting beliefs that keep us from stepping things up, paired with a lack of understanding when it comes to the actual logistics of growing a business that we built out of nothing with our blood, sweat and tears. 

No one taught us how to do this thing, we just started doing it. 

So, now it’s on us to figure out how to keep it moving forward, building it into something bigger and better, year after year – and protecting the integrity of our brand, while we’re at it.

When we first started Oh Sierra, it was just us, The Appleyards, with a pair of crappy laptops, a too-tiny-to-work-from-home-comfortably apartment, and a handful of entrepreneurs that trusted us to show up for them + their communities every day through a myriad of creative offerings. 

We were convinced we would never need to hire – to the point that we would say it in almost every single client meeting when asked about our growth plans. 

“This is a family business, run by a passionate, connected couple with a perfectly complementary set of skills and experience to fulfill ALL of our clients needs, anytime, anywhere. No one would do it the same way we do.”

And yet – we planned to thrive on a global stage. 
And yet – we planned to be able to say YES to every dream client that came our way. 
AND YET – we planned to live a life of constant travel.

So, we said yes, a lot.
We took on clients in different timezones. 
We started booking 3 months out. 
We started networking and connecting with people online all over the world. 
We said yes, some more. 
We travelled. 

And then? We burnt out.

Fast forward to today, and we’re feeling better in our business than ever, in the middle of our own rebrand, with more time to actually look ahead at what’s next. We are effectively LEAPING towards our dreams, instead of feeling constantly crushed by work to the point of resenting the very thing that has the potential to give us everything we’ve ever wanted.

(If you read that and thought, “WELL, WHOOPDEEDOO,” while feeling extremely annoyed at us and weeping into your unending to-do list – we wrote this article FOR YOU). 

The problem is that as entrepreneurs, we look at outsourcing through a lens of fear. 

We see it as:

  • Surrendering our dreams to the hands of someone else. 
  • An act of admitting our own lack of capacity. 
  • Something that gives our clients a watered-down version of what we offer on our own. 

But what if we looked at it like this:

  • An act of love for and a means of preserving (and growing!) what we’ve created.
  • Something that makes our businesses (and our lives) more WHOLE. 
  • An opportunity for our clients to not only work with us, but ALSO work with hand-picked experts that we’ve chosen to bring on the team to give them a better experience, start to finish. 

The difference between Oh Sierra now, and Oh Sierra in its early days?

We started asking for help. 

We started figuring out what we needed to do – where to invest, who to hire – to make our lives EASIER. 

But here’s the thing – and what inspired us to write this post – even once we overcame the whole “we can handle anything ourselves” mindset, we still felt stuck. We didn’t even know HOW to begin growing our business through outsourcing. Once we actually admitted we needed help, our minds started racing with a whole new slew of questions.

What should we outsource first?
How do we choose the right person?
How will we explain this to our clients?
How can we protect our business from a legal perspective?

These questions are highly un-sexy and they are also HIGHLY UNANSWERED in the “SCALE YOUR BUSINESS!” chants coming from motivational accounts of the IG world. 

So, we want to share the first six steps we took (and the lessons we learned along the way!) while growing our (now-not-so-) small business:

1. Get Real About Your Needs.

Make a list of all the things you *no longer love* doing in your business, OR, things you’re doing regularly but don’t feel like you’re an expert at. Then, decide, based on that list, who you need to start looking for. When thinking about your needs, also consider things like working style, and whether you’re hiring for a contractor or an actual part-time/full-time employment position. 

2. Determine Your Systems. 

Before you start approaching your potential collaborators, think long and hard about how you envision the relationship actually happening. We’re talking touch points, timelines, expectations, feedback, the whole thing. This doesn’t mean you have to have everything figured out before you can even start opening up dialogue, though –– transparency goes a long way when it comes to building a team who will respect your leadership. 

3. Hire for Quality, Not Quantity.

If you’re feeling like it would be impossible to find someone who encapsulates everything you need in a person – stop looking for so much in a person. Rather than looking for someone who can do all the things you need at once, consider looking for multiple people who can each bring unique value to the table. Our team is composed of individuals who each do one or two things for Oh Sierra, and they do them well. Several, strong parts, make a VERY strong whole.

4. Talk Candidly About Compensation. 

This will vary depending on industry and your agreement, of course, but we highly recommend making these conversations collaborative and compassionate. Since we have assembled a team of contractors, we always connected with them first to find out their rates, and have built them into our own packages so there are never any surprises when it comes to billing. Figure out what makes most sense for you, but keep expectations clear and communication open.

5. Legitimize the Partnership.

Ohhh yess, we’re talking LEGAL DOCUMENTS! We have loved working directly with our lawyer to build contracts that are specific to the way we operate. Think about the things you want to protect – like your proposal documents, systems, passwords, client information – as well as safeguards for timelines, feedback, unfinished work, and the like. 

6. Scream It From The Rooftops.

Your team has expanded! THIS IS A BIG DEAL! Outsourcing is a sign that your business is successful enough to support the livelihood of other collaborators, and that’s pretty badass. Explore how you want to share this with your clients – does it warrant a direct email, or maybe just a social post? Either way, remember to share how SUPER EXCITED you are about it so that they will be, too. 

Here’s the thing about owning a business: it has the potential to give you everything you’ve ever wanted. You CAN be in control of your outcomes, responsibilities, day-to-day life. You CAN be truly free. And yes – you CAN step away from the front lines of your business confidently, and everything will just work out. 

Or, you can let it crush you. 

We refused to choose the latter.


The Appleyards

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About The Appleyards

We Are Passionate Community Cultivators, Partners in Life and Business, And Firm Believers That Work Should Feel Like Play.

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