The Upside

Mistakes to Avoid When Building a Community

You may have seen a lot of buzz (and gossip) going around lately about Chief. If you don’t know what I’m talking about, just take a quick look at this viral LinkedIn post and you’ll see what I mean.

This one post, by the way, sparked hundreds of similar LinkedIn posts, tens of thousands of LinkedIn comments, and dozens of articles in Forbes, Fortune and the likes.

One viral post. And now it seems like everyone is talking about Chief these days, for better or for worse.

I never joined Chief so I can’t comment on what they did or didn’t do right. But here’s what I do know to be true:

Community doesn’t play by the same rules as other business models.

When I started building The Upside community, I quickly realized that I needed to unlearn so much of what I was taught about business. In fact, I just threw the rulebook into the trashcan. Here’s why:

Trashcan Rule #1: Create FOMO to generate interest in your community.
Sure, we’ve all felt the curiosity that comes with FOMO marketing tactics, like: Limited time offer! Hurry, act now! Limited spots available! The last cohort sold out! And Chief mastered the art of FOMO with their mysterious application process and thousands-deep waitlist to join.

Lesson to be learned: Like those impossible-to-get restaurant reservations, eventually the hype dies down. And when it does, you better have some serious substance to whatever it is you’re selling. Substance and quality always beat out hype in a community business.

Trashcan Rule #2: A business can be exclusive, while also valuing inclusivity.
Chief worked hard to feel like an exclusive club for high-level executives. However, this exclusivity has left tens of thousands of people feeling rejected, with no explanation as to why they didn’t make the cut. This is the very foundation of being non-inclusive.

Lesson to be learned: A community can’t be exclusive and inclusive at the same time. They literally contradict each other. Pick one and own it.

Trashcan Rule #3: Raise lots of VC money so you can impact more people, faster.
The product-market fit stage of a community business is much longer than traditional tech companies. Building a successful community takes care. And care takes time. When it comes to community, VC-fueled, fast growth has never (ever) led to long-term success.

Lesson to be learned: It’s the turtle–not the hare–that wins the race in a community business.

Trashcan Rule #4: Use celebrity status to lure in the regular folks.
Chief is not the only community guilty of leveraging big-name members in their marketing. But here’s what I know to be mostly true: when you join a community, you won’t actually have access to those big-name celebrities.

Lesson to be learned: In community, superficial optics fade fast while authenticity creates long-term value, loyal members and measurable impact.  

Trashcan Rule #5: Build value and marketing around the brand, not the founder(s).
Soooooo…I fought this good fight for at least two years because it’s Business 101 to build a business that doesn’t depend on or revolve around YOU.

But ultimately, I learned that the draw of any community is directly correlated to the leadership style, values and personality of the person (or people) leading it. In fact, there’s not one person who joined The Upside without looking up “Erin Halper” first, or subscribing to my weekly email, or downloading one of my free guides.

Lesson to be learned: In community, you can’t hide behind your brand. You ARE the brand, whether you like it or not.

Whether you’re thinking about joining a community or building one, I hope that these trashcan rules reframe how you think about the business side of community.

Erin Halper

About the Author

Erin Halper is the founder and CEO of The Upside and the leading authority on independent consulting. Since launching The Upside in 2017, Erin has helped thousands of professionals transition from corporate life into consulting to achieve flexibility, autonomy, and a renewed sense of purpose in their careers.

Erin has been a frequent speaker at Columbia, NYU, Harvard, and Brown and has been featured as a leading future of work expert on dozens of podcasts as well as in Forbes, Business Insider, Nasdaq, Crunchbase and many more.

Get insider access

with our weekly newsletter

You’ll receive our Pricing Playbook, tactical tips on growing a consultancy, real-world stories, and solutions that will inspire you to play bigger.

Want a behind‑the‑scenes tour of The Upside?

Join us at The Upside’s Open House event on March 8

Someone has nominated to fast-track your membership to The Upside.
Accept your invitation and apply here before applications close on December 25.
Erin Halper of The Upside

Registration Now Open!

The Upside Accelerator

Bar

FOR EARLY – STAGE CONSULTANTS

Doors Close October 24!