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JENNA KUTCHER

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My Top 3 Business Takeaways from My Puerto Rico Mastermind

After spending January in Maui with my fam, Drew and I had a baby-less getaway to Puerto Rico to accomplish two very important things. I love a good multitask, and this one was the epitome of killing two birds with one stone because we got to be a couple on a child-free vacation celebrating Drew’s birthday, AND I got to be a part of a mastermind that stretched and pushed me in ways I needed to kick off 2020.

It was the best of both worlds, Drew and I doing what we loved all day and then reconvening at night to rehash all our amazing experiences. And while I shared how much of a gift this trip was for us as a couple, I wanted to also take some time and reflect on the ways it encouraged and challenged me in terms of business.

As a side note: at a separate mastermind last year with Tony Robbins, Tony kept on bringing up this idea of “preparing for winter.” He’d acknowledge how many of us in the group were too young to have experienced the 2007 crash and how it devastated so many small business owners (and humans in general). He kept urging us to start getting systems in place now and learn how to deal with major slow-downs, market downturns, and clients and customers no longer able to buy. It was almost like this massive, eerie theme: prepare for winter, prepare for winter. And not to get all Game of Thrones-y on you but … he was right.

We are in a winter season, friends. With Covid-19’s arrival and the postponement of many events and closure of many companies’ doors, businesses of all kinds are already taking a hit, online, brick and mortar, product-based, service-based. Even though no one knew it was coming and we couldn’t have prepared for this if we tried, there are still ways to survive this season and protect your business. I created a free, 10-page Small Business Survival Guide for this reason, to help all types of businesses take steps to walk through this time with more tenacity and grace.

And for now, I’m sharing with you my top 3 business takeaways that I had at my Puerto Rico mastermind earlier this year to take with you as you navigate your own winter.

01. How to approach this decade.

At the mastermind, there was a lot of talk and exercises around defining success and what that looks like for each of us, and how to unapologetically go after that this decade. Spoiler alert: everyone’s version of success is so incredibly different — especially right now. For me, you probably already know that my measure of success has way less to do with money and accolades, and more to do with time, freedom, and impact. That looks so different from a lot of other entrepreneurs, even many of whom I sat at the same table with at the mastermind.

But as we talked through it, it became so wildly clear that only chasing and prioritizing your own version is what’s important, even if it’s simply making it through the next 6 months. If you hear everyone in your industry talking about reaching 6 figures but you couldn’t care less about a dollar amount, then don’t make that your mission. If you’d rather focus on working three days a week and making enough to save for a comfortable retirement, make that your measure of success.

It can be easy to get swayed by what we see everyone else doing and going for, but this year and this decade, let your values and heart lead you. That is a better way to tally your success than the constant comparison and competition with others, whose measure of success isn’t even in the same ballpark as yours. And by the way, if your goals are based on other people’s goals, you’re never going to feel good or “accomplished” when you reach them, at least not in the way that you would if you actually went after what’s really on your heart and soul.

There may be some mindset shifts needed to reach YOUR next level and to help you stay in alignment for the best decisions to reach your success. We talked a whole lot about how to embrace those shifts, to listen to your intuition and not your insecurities, and to push past outside voices in order to get really clear on where your gut is leading you. After the trip, I’m laser focused on tuning into this part of my brain, and I invite you to join me to do the same. Listening to your gut in this season is crucial, actually.

02. Differentiating the content you put out.

If you want your name everywhere, how are you giving your audience exclusive content but also introducing yourself to new audiences? This was a big theme that came up again and again in Puerto Rico, and I think it’s because we’re always dreaming up new ways to scale and grows our businesses to that next level. Plus, with so many working from home right now, there are more people than ever on social media. While they may not be buying as much right now, their presence is important to utilize as you grow your audience in a shaky time.

But at the same time, we don’t want to leave anyone in our current audience behind, and we want to nurture our people who have been rallying behind us the longest. When considering collaborations and partnerships, and how to really make those work well for us AND our people, ask yourself: who’s doing things you admire that you want to partner up with that would be a natural and easy fit?

Those kinds of partnerships will ALWAYS feel more organic than just choosing to sync up and work with anyone and everyone who comes knocking at your door. Ask yourself what matters to you, and then find the people who align with that — who can you partner with to support and show up with? Work with them in a way to serve your audience even more value, not to just selfishly get in front of more eyes.

03. Continual revenue opportunities.

In the entrepreneurial space, especially in the online education world but really everywhere right now, revenue is a bit like a roller coaster. That’s not a bad thing by any means if you can prepare for the drier seasons, but not everyone is able to prepare in a really effective way. During launches, revenue spikes, and then during prep and rest and unforeseen emergency seasons, it’s obviously slower. It’s the ebb and flow of running an online business — and any business, for that matter.

It seems like a lot of people I know in this industry are wanting to move toward things like membership sites on top of their other offerings. Not only does this provide continual revenue for the brand, but it’s also a consistent way to continue serving your audience and showing up for them on an ongoing basis.

It’s more community based than product based, which is something I can totally get behind and something we ALL need. Truth be told, I’ve considered starting a membership site for this reason, to be more of an ongoing resource for my people, and it’s something I think I’ll do eventually… one day! Would you be interested? Drop a comment below if you’d be into a JK membership.

For now, I’ma keep doing my thing, showing up for you online and giving you all the goods and tools to make your very own business a success — on your own terms. But I absolutely loved this mastermind experience because it got me thinking of new opportunities, ways to stretch myself in this decade, and how to protect my audience while exploring new partnerships.


If your business is hurting right now, I’m here for you.

Get my free small biz guide to take actionable steps to protect your business and survive this season.

by Jenna Kutcher 

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