TBM 3/52: Real-World Learning Review

This week I will try something new, and I hope you like it.

As some of you know, I am an investor in DoubleLoop, an early-stage startup based here in the United States. I was chatting recently with Dan (the founder/CEO), and he said he wanted to do a learning review session for DoubleLoop and share it with the world. I shared that I hoped to add more "actionable" content this year (without glossing over the mess).

So we hatched up this idea: I would run a review session for Dan, provided I could share it with my newsletter audience. First, I can't thank Dan enough for being vulnerable like this. Being a founder is NO JOKE. Yes, he said he wanted to "build in public, " but following through like this is super impressive. Thank you.

Suffice to say, it is very rare to get this kind of view into an early-stage startup.

Here is some quick context about DoubleLoop before jumping in:

DoubleLoop is SaaS tool for modeling business drivers with data-connected maps. They've raised $2.8M so far. While they have early traction, they're iterating on their product and positioning to create strong product/market to raise a series A about a year from now.

Here’s the video! I have timestamps in an outline below.

Here’s an outline of our conversation. Feel free to jump around or watch the whole thing. Dan would love feedback, so feel free to email him at: dan@doubleloop.app with questions.

Short intro by Dan (0:00)

I check in about morale, team health, etc. (0:32)

Rewind to 6 weeks ago. Talk me through your view of the world then. (3:02)

• Focus on metrics, goals, assumptions

• Dan realizes he flipped an input and output (common)

• Dan notes where the North Star Metric fell short in reflecting customer value.

How would you brutally critique your view of the world six weeks ago, given what you know now? (7:03)

• Dan gives a deeper critique of himself. Bold move! He notes he didn’t think he was going the “full mile” to determine if they were solving a customer problem.

• Reviews key assumptions.

• Historical “wins” being a step towards future progress (but “not enough” in retrospect)

Please show us your current map, and review the difference between the new map and the old map. (10:00)

• Talk us through each change. New nodes, new metrics, insights. New bets

• The new map is part of a strategic reset

• Embraced complexity in the map

• North Star Metric is “way harder to grow.”

• Metric challenges (measuring some things is hard)

• Drivers vs. metrics vs. measurement

Given your current set of inputs, discuss leverage points, and key assumptions. (15:21)

• Talk through “opportunity” focused bets. 

• Discuss leverage points, assumptions, and “that is why we will try _____.”

• Resist the urge to “just build.”

• Zeroing in on the product analyst persona

• Dan does a mini-retro on “playbooks” (their UGC play)

• Using services to understand the customer challenge deeply

We discuss work that doesn’t show up on the map. (25:43)

• Multiple maps. Proactive and reactive work.

• Find levers of growth. High leverage

• All work represented on the map is the ideal

The final row of “solution” bets. (29:45)

Top 2-3 assumptions, 2-3 risk areas. (31:59)

• Dan digs into the “strategy services.”

• “We have to get good at helping customers model their strategy.”

• Which causal connections are the most significant leap of faith

• Dan acknowledges he “isn’t an analyst” (strong self-awareness)

• Is the value prop too abstract?

Goal setting! (41:17)

• New map! It is hard to set goals

• Dan has limited experience with these metrics

• It will take some time to figure out if these metrics are moveable

• The goal is to explore levers!

• Qualitative goal: Do sessions. Learn from customers.