1 year of the newsletter: What's next, what worked and what didn't

A year ago, I sat down at a beach house, lit a cigar, and crafted my first newsletter for Silicon Holler Founding Father.

It wasn’t great.

I was trying to use the format other people recommended:

• Quick reads / bite-sized content

• Don’t make it too personal—focus on lessons not life

• Go hyper niche

• Be Tweetable

Over the next 52 newsletters, though, I’ve realized that’s just not for me. And apparently, it’s not for you all either.

My most read newsletters have been pretty much the antithesis of what the experts told me to do. Those posts were vulnerable, personal, long form, and focused on founding a company or leadership, and not hyper specific at all, like say, “founding a venture-backed tech company in the midwest when you don’t have a tech background.”

The top performing newsletters this year were:

• Why I canceled our festival

• I screwed up this week—don’t make this mistake

• The worst vacation policy I’ve seen—and how to avoid it

• The process I’ve used to raise $7M

• Your cover letter sucks

• The quick-start guide to creating content

• Political correctness is killing company culture

My first 11 pieces aren’t anywhere near the top. And most of my best performers have been of late, so it would seem I’m slowly figuring it out.

Why I do this—and why you should share your story

I share a lot of content. Some of it’s ridiculous content on LinkedIn, like picking fights with Facebook founder Mark Zuckerberg (he still hasn’t responded to my challenges), sometimes it’s deeply personal, and other times I try to be helpful.

It all comes down to this—every week, I meet someone who knows what I’m about because of the content.

As I’m building my business, I have to be the Chief Storyteller. No one else has the ability to build and share the vision like I do. I am the hype man for GoWild and Holler Commerce. These efforts may seem like a lot of work on the outside, but I’ll forever maintain it’s worth it to share the good work we’re doing, maintain enthusiasm for our products and to stay top of mind. I sat down with a potential investor just this week, and he said two things that tie back directly to content:

“Everyone I’ve met seems to know who you are.”

“I love your journey and story.”

What’s funny about this? I don’t even personally know the people who said they know me—they follow me on LinkedIn. My content reaches further than my direct personal connections.

Trust me, I do not do this for personal attention. Honestly, I hate the attention at times. Putting yourself out there generates blowback, whether it’s LinkedIn messages, emails or social media comments. I’ve been called a Tim Ferris wannabe, sugar coater, deck shiner and more. I block or unsubscribe the haters, and move on because the goal is connecting with those who are being helped, not arguing with those who aren’t.

What’s ahead for Silicon Holler Founding Father

I’m going to continue to lean into content that directly can help early-stage founders, which will also help leaders of small to mid sized companies. I’ve never worked in a massive corporation, and have no intention of doing so. I love small teams. I love building. And I love creating something out of nothing.

I’ll continue to write about building a great culture, challenges our startup has faced, lessons I’ve learned with fundraising and negotiations, and I’ll probably have the occasional piece on my attempts at balancing my work and responsibilities as a parent and spouse. Despite the occasional piece about parenting, I am considering changing the name of the newsletter and dropping the “Founding Father.” That change is TBD, but feels right.

Thank you to those of you who get this far into each piece

I don’t really care if it’s not for everyone. I’m writing from the perspective I’ve earned, and that journey isn’t going to resonate with many founders or leaders.

But enough of you read, reply, message and comment each week that this little project has proven worthwhile. It’s given me a little side project to lean into once a week, and I truly enjoy it.

So, for today, I just thank you. Thank you for sharing the newsletters, letting me know when a piece resonates, and for reading every single week.

Cheers to another year of sharing.

- Brad

Who I’m listening to: Kainen Kellum

What I’m reading: “Play Bigger” by the Category Pirates

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