Making Bets, not Guarantees

August 8, 2019

Like I’m sure tens of thousands of other people, I read Basecamp’s new book Shape Up.

The release was perfect timing. For weeks I had been reading anything I could get my hands on, interviewing folks from really successful companies, and just trying to answer the simple, yet nagging question:

“I feel like there’s a better way for our company to be working, but what would that look like?”

What’s interesting, is that perhaps the most useful thing I learned was more written between the lines than spelled out explicitly in any given chapter or section.

It was the idea of placing bets.

Bets vs Backlogs…
The book outlines the way they make bets in this way:

“Backlogs are big time wasters too…So what do we do instead? Before each six-week cycle, we hold a betting table where stakeholders decide what to do in the next cycle. At the betting table, they look at pitches from the last six weeks — or any pitches that somebody purposefully revived and lobbied for again.”

What’s interesting is that how, in their case, the opposite of placing bets seems to be a backlog.

But in my situation, the opposite of a bet is a guarantee.

…or Bets vs Guarantees
What I loved about the bets concept wasn’t that it replaced our backlog, it’s that it replaced mindset that was hindering my decision making process.

I’d look at a block of time – let’s say a month – and say to myself:

“What is going to move the needle. What is going to be the absolute best use of my time?”

But nobody knows what’s going to move the needle. I can’t see into the future and there will always be some uncertainty around that decision making process.

I was looking for a guarantee, instead of just making my best guess.

Huge Change
So at our last planning meeting, Patrick and I tried something new:

  • We looked at where we were.
  • We tried to describe where we wanted to be at the end of August.
  • We imagined our time was a stack of 10 “chips”.
  • And we spread out those chips across a combination of campaigns and features and work that we hoped would get us there.

Almost like a stock portfolio, some of those were high return but high risk while others were low risk but almost certain to give us something in return. It gave each decision context and a much needed dose of clarity.

But simply embracing the fact that we were never going to get it perfect? That made all the difference.

More updates from my making-bets-not-guarantees journal:

Hi, I'm Gregg.

I'm a marketer, maker, and long walk taker.


By day I run marketing for resort CRM / ecommerce provider, Inntopia. After the kids go to bed my laptop is my workshop where I'm building an email marketing tracking platform called SendView.