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Issue #20: Rallying to Build Momentum

Two years ago, we hit a really rough patch. We had roughly 10 people, were expending about $60k per m

James Costa

August 1 · Issue #20 · View online
A batch of thoughts, resources, and motivation from a friendly digital agency owner delivered every Monday at 6am ET.

Two years ago, we hit a really rough patch. We had roughly 10 people, were expending about $60k per month in total expenses and payroll, and owed about $25k that we didn’t know where we’d find the money for. While we had a few projects ongoing and a few new ones starting up, things weren’t moving fast enough (and, let’s be real, invoices weren’t getting paid fast enough) to keep us afloat. We saw this coming for months but kept expecting things to pull up. We started having conversations with other agencies about what it might look like to be acquired or merge. I was freaking out, but also needed to stay focused on solutions. I still believe this was one of my biggest tests as an owner, and marked a pivotal turning point in how I viewed the company.
A few of you may be reading the above and nodding vigorously. It’s a scary situation to be in for those of us who have bootstrapped our companies. Most of us don’t have a secret stash of money we’re sitting on, and we care deeply about our people enough that the stress affects our whole being. We put all the stress on ourselves, when we admittedly don’t always have all the answers or even necessarily control over the outcomes.
The reality is, the solution is scarcely only ever on one person. For us, the solution was multi-faceted and meant needing to focus on improving our accounts receivable, getting better payment terms for our accounts payable, and having the team focus on getting as much done as possible so we could bill faster.
Ultimately this led to our writing out first “State of the Union”. The idea behind it was simple: we needed the team to push to get us over the hump in the coming weeks, but we couldn’t have them do that if they didn’t know what was going on. I laid out the situation and gave the team the choice: they could either decide they’re not up for it and leave with the best reference letter they’d ever get, or stay and fight. We also gave the team a bit of a status spreadsheet that outlined all of the important numbers and what we were looking at (which ultimately inspired our cash flow spreadsheet which I’ll share in a future issue). If any of you have watched Game of Thrones, at one point late in the first season Tyrion gives a rousing speech to rally his troops that lies at the heart of that first State of the Union.
I gave each of them a few days to think through it, and scheduled individual meetings with everyone to discuss. In the calls, I asked them what their thoughts were, and asked them each whether they would be sticking around or not. The outcome was overwhelming. Not only did everyone say they wanted to stay on board and fight, but they went over and above the expectations I had for them. The team put their trust in me to lead through a tough time and took a huge risk that I’m still grateful for today. Even in our best times I remind the team of what we’ve had to go through as we continue to fight to build the business we want.
To today, the State of the Union has served as a quarterly rally point for our team to band together and ensure we know what’s ahead of us. The post itself usually has a few core parts to it:
  • How we did in the previous quarter, and what we accomplished. We include numbers for what we invoiced, and any numbers relating to goals we have as a team (which are in a central company Trello board that everyone has access to).
  • What our goals are for the next quarter. Usually these are in line with the yearly goals we put together, but also allow us to create goals throughout the year and update goals with reality as we go.
  • A particular topic or idea for the team to focus on. This has ranged from the topic of whether we’d always like to do client services, to whether or not we need team leads. We also talk about where we’re at as a business from a qualitative point-of-view and look at the landscape of our industry.
Every State of the Union is followed by stand-ups with each individual member of the team which last anywhere from 10 minutes to 2 hours, where I get to answer questions and (more important) get thoughts from the team about problems we’re facing. They’re honest conversations where the team gets to step back from the work they’re doing and get an idea of how what they’re doing connects to something larger. I just finished a week of these stand-ups and whenever I do I always feel incredibly inspired and motivated. Incredible ideas come out of the conversations I wouldn’t have otherwise had the opportunity to have in the day-to-day. Whether done as structured as we do or not, I encourage every leader to have these conversations with those around them to focus on things other than the day-to-day and ensure everyone is aligned.
Looking back two years ago, I’m so proud of how far our little team has come, and am profoundly excited about what’s ahead. Here’s to your finding the inspiration that drives you through, your ability to honestly share with the people around you, and the growth ahead of you with a strong team that pulls together.
P.S: If you want to have a look at what I wrote this quarter for our State of the Union, I’ve posted it here for you.
P.P.S.: If you enjoyed this week’s issue, I’d really appreciate your support sharing this newsletter. Whether it’s a forward, a Twitter post, or by writing fan faction about me, it would mean the world to me.

Good Reads
Photo by Piera Gelardi on Instagram
The Connection Between Employee Trust and Financial Performance
Why We Pay to Save Time
How Typeform Created A Company Directory That Employees Actually Use
Is Doing Nothing the Key to Productivity?
Weekly Motivation
“America has been through big changes before – wars and depression, the influx of new immigrants, workers fighting for a fair deal, movements to expand civil rights. Each time, there have been those who told us to fear the future; who claimed we could slam the brakes on change; who promised to restore past glory if we just got some group or idea that was threatening America under control. And each time, we overcame those fears. We did not, in the words of Lincoln, adhere to the “dogmas of the quiet past.” Instead we thought anew, and acted anew. We made change work for us, always extending America’s promise outward, to the next frontier, to more people. And because we did – because we saw opportunity where others saw only peril – we emerged stronger and better than before.” — Barack Obama
In Closing
We’ve made it to 20! Each issue is hand crafted and takes time (roughly 2-3 hours per week), but has allowed me to focus on my own growth. Often when leading teams we don’t take enough time to focus on ourselves, but we should be consistently looking to sharpen our skills. We constantly feel like there’s not enough hours in a week, but we need to make this a priority for ourselves lest we burn ourselves out. I’m honored to be able to share my stories and thoughts week by week with you, and thank you for giving me the opportunity to do so. 🙏
If you have any questions or I can help you in any way, all you have to do is respond to this email.
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