Freewriting and Form Breaks: Dave Balter’s Take on Founder Communications

In November 2021, a year and some change into the pandemic (and remote work for many), Co-founder of Flipside Crypto and Venture Partner for True Ventures Dave Balter made the commitment to freewrite a note every week to his team; and not with loose intention.

“I had a rule to hold myself accountable and never miss a week,” he shared. Dave credits Help Scout Co-founder Nick Francis as well as ExactTarget CEO Scott Dorsey’s ‘Friday Notes’ for the inspiration — though Dave’s weekly notes to his team have taken on their own particular, essay-like, and highly comical flavor.

Essay-style founder communications for early stage startup teams

Dave’s “Friday CEO Notes” began as relatively corporate recaps of the week’s outcomes, reminders of company vision, updates on key performance indicators (KPIs), and goals looking forward.

“I slowly began to bore myself to tears, until one day I couldn’t help myself,” said Dave. “I just let go, went off a cliff, and never looked back.”

Since then, Dave’s updates have included a note likening crypto to space travel (that also congratulated team members on 5-year anniversaries), a comical complaint letter to an airline after experiencing spotty wifi, and a confession of a late send amid family needs that — without fabricated intention — communicated his values. He also recently penned a note about writing itself, a nod to his writing mentor, John Butman.

If emojis could talk: team response to informal communication

One fascinating aspect of Dave’s approach is how his team responds. These weekly notes are not just one-way communication; they’ve become a language of their own. Dave drops his notes into Slack at 9 AM most Fridays, and his team responds with emojis tied to themes and ideas shared in the notes.

It’s a form of visual storytelling where the team plays an active role in interpreting and reacting to the note. Some team members even reinvent parts of his notes using AI. The response isn’t about more emoji clicks; it’s about creating a shared experience.

“Sometimes team members spell out a word with multiple letter emojis or come up with a unique association,” said Dave. “In some senses it’s a language we’ve penned all our own: I scribe the note, they respond in kind via a visual, shape, or color. Sometimes they comment, sometimes they don’t. Sometimes they write their own story in response, sometimes not. One person used AI to rewrite parts of the story. That was a conversation in and of itself.”

Striking the right balance with startup team communication

During the pandemic, many companies adopted the practice of over-communicating to bridge the gap in remote work. Dave doesn’t believe in overdoing it.

“Every team needs a healthy dose of communication to understand your mission and values (and be reminded of them regularly),” said Dave. “The needs will change based on stage of your company and where you need to focus your team’s energy.”

The key, as Dave notes, is to adapt communication to meet the company’s needs at any given time, striking the right balance between keeping the team informed without overwhelming them.

While Dave’s Friday CEO Notes are shared company-wide with Flipside’s 60+ member team, the company’s vertical leaders write and share Discipline Leader Updates (DLUs) with a smaller group of 15 leaders within the company each week.

“It’s a shared strategy to express progress, challenges, and upcoming priorities,” said Dave. “It’s critical we establish clarity on our metrics and what good looks like in the new world order.”

Setting pace and tone as a founder

When it comes to early-stage founders, the frequency of broad communication isn’t just about the stage but also about the audience. Dave suggests founders consider guardrails for their weekly notes to their teams, even when they take shape as creative personal essays.

“Focus on larger themes, mission, vision, values, and essential messaging,” said Dave. “It’s about setting the tone and leading by example. You are the pace car and how you communicate indicates how others behave.”

Keeping it personal

While Dave tinkers with AI tools for sales language, writing thank-you notes, and other marketing and administrative drafting, he insists on starting fresh and writing in his own words anything attached to his name.

“I guess I’m just an old-fashioned Boomer; I’m writing this on a Blackberry,” said Dave. (His humor is never lost on us here at True.)

Embracing the element of surprise

While all startups face the shared challenge of prioritizing high-value work over reactivity and notification clutter, Dave sees the at times off-the-wall storylines of his weekly notes as a break from the norm; a “left turn” that gives his team a window into the core of the company and hopefully even some delight; an opportunity for connection no matter disparate zip codes. Dave shared the following:

“There’s a great story about the Grateful Dead’s Bob Weir reflecting on how he played guitar alongside Jerry Garcia. Often the rhythm to Garcia’s lead parts, Weir was more the straight man, but often delivered with funky chord shapes and completely haphazard fills.

“It somehow worked incredibly well. And when they really got going, Weir noted that he would aim to set up a little something special for Garcia to inspire him at the end of a passage. A tiny surprise. A little bit of a left turn where a right might have fit. A framing that might raise an eyebrow or an idea that opened a totally new door to walk through.

“I want our team to see these weekly notes from me the same way. The rhythm of the week can end with something that feels like an exclamation point; something they look forward to on Friday. And just to ensure it’s worth their time, they’re never sure if they’re going to get the fastball, or the knuckle, or a slider.”

Dave reposts many of his weekly team notes on Medium. Follow him for inspiration for your next company-wide note to your early stage startup team.