Clubhouse [Early Employee] – Learnings During High-Growth & Next Career Chapter with Fair Square Medicare

Yup, you read it. 

It’s time to close one chapter and begin a new one. 

This isn’t “breaking” news…

…because hey, we’ve all [for the most part] have had other jobs. 

But with any new start, 

it’s always important to take a moment and reflect:

🤔 What did I learn over the past year and a half from my time at Clubhouse? 

It’s important to start with some context. 

When I started to get involved with the team – Clubhouse was still invite-only…

…and was trending wildly on Twitter. 

For those OG’s reading this – I’m talking about that November 2021 hype. 🙌

With the viral buzz…

…also came an overload of demand across all aspects of the app that a small team of less than 10 has more than enough to keep up with. 

Servers are working at their max. Check. 

Support tickets are being created one after another. Check. 

Tons of feature requests coming in. Check.

👉 Lesson 1: Adding fuel to a fire prematurely is NOT what a startup wants. 

Unpopular opinion it may be…

…but doesn’t every startup want tons of media coverage and users begging for access? 

When something goes from zero to hero overnight – there NEEDS to be an infrastructure in place to support it. 

And I’m not talking about a technical infrastructure…

…I’m referring to the overall machine set and ready to go. 

Servers up and running is just one small, technical part. 

To accomplish building this infrastructure the team needs to be extremely disciplined across all aspects of the business. 

👉 Lesson 2: Ruthless Focus is the #1 Priority.

Ben Horowitz talks about the War-time and Peace-time CEO…

…the concept expands beyond the leadership team, 

But instead really sets the tone for the ENTIRE team. 

When everyone knows that it’s all hands on deck and time to grind, 

it’s essential to know that your teammate is to your left…

…and you right are on the same page. 

It’s what will make those long nights and hard discussions bearable. 

THESE are the times that will help forge the bonds between everyone, 

Not only with those on your direct team – but company-wide. 

Having the right dynamic within the team is essential to making sure everyone makes it through this ‘messy middle’ time.

👉 Lesson 3: Build a hungry team that can leverage past experiences, but not look to duplicate them. 

Build a hungry team…

…regardless if they are an industry expert, 

or a college graduate – 

The team needs to be HUNGRY wanting to make the company mission become a reality. 

It’s important in larger companies, sure, but within a smaller team…

…this mentality needs to be amplified across each and every team member. 

What someone may not know – they need to be willing to learn. 

What someone does know will help reduce time to value…

…but you MUST keep in mind to maintain the flexibility that THIS problem may need to be different than how you solved it in the past.

📖 The Next Chapter: Fair Square Medicare

What do they do in one line? 

Concierge-level medicare insurance broker that you can confidently recommend to your own parents, 

and is a team you can call on throughout any of your ongoing Medicare needs.

TL&DR: Make medicare “actually” work

The WHY for me on this one runs deep…

…as someone that has been involved in a variety of discussions with my grandparents, extended family, and own parents…

…this is something that is not easy to understand nor manage. 

From Medicare Plan A through Medicare Plan N, 

There are so many complexities that lie within each plan that selecting the wrong one can literally lead to a quicker death. 

🔁 Read that again: Selecting the wrong Medicare coverage can literally lead to our own parents dying earlier. 

How? 

Something medically happens to our parents that should have been covered in a plan from the start…

…that wasn’t. 

That is SCARY considering it’s not only mandated by our government to purchase, 

But we are also responsible to figure it out on our own. 

There are advisors out there today, 

but their incentives are totally misaligned. 

Traditional brokers receive a commission based on the plans they sell. 

This means that some plans put more money in their pockets than others…

…so naturally, that will create a biased approach to their recommendations. 

What really spoke to me about Fair Square Medicare was that the team that wants to flip that model on its head…. 🤯

Stray from the cash incentive from selling a plan, 

And focus on the plan that is actually utilized and aligned with the person who purchased it. 

In the startup world, 

it’s definitely a big hairy audacious goal (BHAG) to revamp the Medicare experience…

…but that is what makes it so special. 🤩

Really looking forward to how this next chapter will not only improve the lives of my parents, 

But each and every person’s Medicare experience going forward. 

Thank you to the Clubhouse team for the past 1.5+ years of amazing memories. 🙏

Hello Fair Square Medicare. 👋