📻 — The Inevitable Pivot: Thoughts on Starting (and Restarting) Communities and Startups

Reading Time: ~ 4 min.

Good morning yeniverse!

I have a bit more of a personal retrospective that I’d love to share with you in today’s issue but before we jump, here are a few good reads around the interwebs:

  1. Gumroad is trying Clubhouse instead of Zoom. FascinatingAirsend?
  2. Oh, to be young… and single… and to have a Jeep. LinkedIn Tips.
  3. How safe? OMFG. Hack the music. Don’t run out of cashMetahuman.
  4. Underwater photography winners. Everything is buggy. Podz RSS?
  5. Design system for Shopify. Developer portfolio. React VR/AR.
  6. Open source virtual event design, page. Wow. One more. Windows 7.

To infinity & community,

— john


Can we talk starts and “restarts” today? Can we talk “pivots”? Can we talk about the fact that as a creator, as a builder, as a serial entrepreneur that I’m constantly trying to figure out why things aren’t working and the fact that I’m always having to (re)create my projects over and over and over again?

Well, I guess we asked for it, right? This is the cost of being a true creator is this: We are always disappointing a ton of people. Always. This is what we signed up for.

Okay, okay, okay… some of you already know quite a bit about my personal / professional story but for those that don’t, let me run you through some of the larger projects that I’ve had in my career and the fact that all of them required a significant pivot, restart, or… effectively abandoning the “original idea” in sake of a better one.

TL;DR: Every single startup that I’ve worked on has pivoted at least once.

Here are some of the larger projects that memory lane took me down:

8BIT — Dec 2014, WordPress VIP After-Party

8BIT — We started as a software agency and pivoted to a product shop where are two products were eventually acquired; my first venture capital fundraise!

June, 2015 — Global All-Hands — Greenville, South Carolina

The Iron Yard — We started as a technology accelerator (a’la YC / Techstars) and pivoted into a 12-week software bootcamp to train full-time developers. It was acquired by a Fortune 500 just a few years later. It’s still hard to look at the above picture of all the folks that I hired… and the memories we made together on that long and difficult journey. I made some life-long friends and I’m so grateful for that.

The OG YEN Team, 2018.

YEN — We started in 2017, focused on the decentralized finance industry and after 3 years of riding The Startup Strugglebus™️ I pivoted the company in 2020 to community / communication data. We now have a clear path forward and enough money to get us to the next milestone. Our story, together, is still being written…

Pinpoint — 2016-ish

Pinpoint — I joined as a founder in 2016 and our mission was to build the system of record that tied engineering analytics to business outcomes. We gave it a serious shot raising > $16M+ in venture capital. But even though we had a massive financial war-chest it’s still impossibly-difficult to get to the promised land of Product-Market Fit.

Consequently, just this past week, my (previous) cofounder announced a pivot to attack a growing need in business operations, productivity, and content.

My first “big” software project / startup. August, 2007

Datecraft — My first major startup project was actually born out of the ashes of the first failed software platform — a social network for adoptees (as seen above).

A year later I refactored the codebase (not entirely a “pivot”) and launched a dating website for World of Warcraft players. It actually worked and in March of 2008, I went public with it (and got a bit more local press):

Datecraft, March 2008

This project would later be acquired by a larger dating conglomerate and would give me my first “win” and “exit” as a startup founder and entrepreneur. I would then go on to build many more projects and companies, a few of them listed above.

Community, All The Things.

There are two lessons that I want to share with you, the first is obvious and the second is not as obvious:

  1. Your original idea is unlikely to be the idea that eventually builds the business. Meaning, the original idea may get you started and headed in the right direction but there is a very good chance that the product that will eventually make you money will not be the one that you started with.
  2. The community that you build for the first iteration of your business / project can also be the community for not just the next iteration but also the next project! Meaning, as you build the folks in your larger orbit may decide to follow you, not just the project, thus growing the larger community around you and your personal brand. Be like Horst Schulze and be excellent (and kind) always.

Real community is functionally fluid and infinitely portable. Meaning that the folks that you authentically connect with will be more interested in you over the long haul than the project(s) that you start and eventually have to kill.

This is life. Starts. Stops. Beginnings. Endings. Things come… and go… and then do it all over again.

And throughout my entire history as a professional I’ve been slowly, one-by-one, building a (personal) community that grows whenever I dare to hope, dare to build, dare to believe that I can actually build the project, community, and business of my dreams.

I’m still doing that… are you?

If you’re down… I’m down. Let me know how I — and our amazing YENIVERSE — can help you build the project and business of your dreams.

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