Break Time

The Importance of Scheduled Downtime


It's Spring Break time in the US. Though mainly for kids taking a week (or two) off of school, it ends up being a time for a lot of people, especially parents, to look to take a break too. I just got back from a family ski trip (no significant injuries!). Jason took his family to DC to learn about history (and walk about 85 miles through the DC Mall). Chris...well he was heads down looking at all of the deals that are coming our way, but he has some nice break time and travel scheduled for early in the summer. We all enjoy traveling and family time...and who doesn't love the first signs of Spring. But I want to talk about breaks.

Breaks are important parts of the rhythm of life. Things get busy, inevitably. Businesses hit challenges or opportunities when they need our complete attention and 110% effort. It turns out there is almost always some crisis or big opportunity in life and business. If we don't schedule/force breaks, we end up moving from one big effort situation to the next without taking time for ourselves to just stop...breath...don't think...don't hustle...don't 'crush'. That leads to being overwhelmed and poorer performance.

Big Band is new, so it may seem weird that it felt so good to take a break. But it turns out launching a business is really hard and there are always dozens of things to be done and only three of us (with a great extended team) to work on them. These breaks were yet another reminder that we need to accept, embrace, and schedule the cycles of life and work. Because life and work will always give you something to do…you probably have to schedule your breaks.

A break doesn't have to involve traveling...but it helps. Actually, Jason feels like he needs a vacation from his vacation because DC keeps people pretty busy if you want to learn and see everything it has to offer. But a break can simply mean not doing the thing you would usually be doing. I realized I was really 'taking a break' when I found myself doing a puzzle with my kids in the middle of a Tuesday morning. That is not normal life for me, but it felt good, it took my full attention (it was a super hard puzzle!) and it gave me a recharge.

Hopefully you have had a recent break and it gave you a recharge. If not, think about scheduling one soon. Even a long walk without your phone or a few hours in a coffee shop without looking at email can give you that recharge that helps you show up better afterward.

Write back and tell me your best break strategy. I may share it with the group in a future letter.

— Kevin

THE PLAYLIST (What We're Watching, Reading, and Listening to)

  • Made with Grit - Our very own Chris Reedy breaks down how founders can prepare for an exit, the current acquisition landscape for B2B SaaS, and IRC Section 174 treatment of R&D expenses and how it’s impacting founders’ taxes this year

  • What is a Software Company Worth? David Robinson, Head of Research at ParkerGale Capital, breaks down 20 years of public data to help inform what SaaS companies are worth. The private markets that we play in have their own unique dynamics but David’s research sheds light on what’s happening up-market - which inevitably impacts transactions across the board. The biggest takeaway? While multiples have contracted across the board, companies with modest growth and consistent profitability have seen much less decline in value vs. their high-flying, grow at all costs peers.

  • Tech companies continue to shed opex in the face of a slowing economy, higher interest rates, and contracting budgets. Over 150k positions have been eliminated YTD according to

  • Understanding Section 174 & how it might impact your tax return. This new legislation requires businesses to spread R&D expenses over five years vs. deducting in the year it was spent, potentially resulting in a major increase in tax liability.


  • Jason will be in Denver, CO April 16th to the 19th, attending Microconf US. If you’re attending or live in the area and want to connect please be sure to reach out!


While we’re not hiring quite yet, we’re building our database with the best leaders and operators out there. If you know exceptionally talented people that may one day want to work with us, please have them get in touch with us at [email protected] or fill out the form on our Connect page.

Was this newsletter forwarded to you? If so, subscribe by clicking the button below and follow along with our journey!