Fixing Things Using AI to Plan Tactics. An Experiment.

Rob Tyrie
4 min readApr 7, 2024
Photo by iwin on Unsplash

It is good to rethink things. And to use advisors and tools to do that.

I created this result below with Claude.Ai. I was generated with a complex, 17 point prompt, the following business planning summary . It was based on a business status note.

I am advising founders of a knowledge based startup are trying to do a 3 year plan and they are getting to be on the same page. They are very much like a software company using agile techniques.

I have done more than 15 start ups and scale ups in software across the last 25 years.m share. I have helped create and wired to take unicorns to duocorns. I personally prefer the following ARR revenue… $1M, $3M, $8M, $34m, you see the scale pattern here. Each stage needs a new strategy, methods, measurements, systems and tactics. System Thinking 101… and Accounting 101. Because, business.

I will say the same thing Joanie Mitchell said… “ You’re so vain, if you think this song is about you”.

The input letter and prompt design for AI is not real, the problem is in a number of start ups I work with. It based on a useful amalgam of problems .

In this Modern Company, they use AI to analyze and summarize things to go faster and help make decisions. They make event driven knowledge objects that are valuable like software and research analysis.

Every thing that follows was generated with edits to smooth things out.

What follows is generative AI results using Claude.AI with some light.efdits to protect the quileless.

I asked Claude to be a systems designer and design thinker from Silicon Valley Software start up culture..If you don’t like the diction and tone, call San Francisco. Fortunately or unfortunately, this is a familiar tone for me after working with awesome Valley Cos for a a couple of decades.

Strap in here we go. Note there are cliches but see above. Not my fault. 🥸

Photo by Growtika on Unsplash

Let’s do this Claude.AI … ding ding ding, lets go!

To: The Founder

From: The Other Founder

Subject: The Advisory meeting and your summary. WTH

Hey my man. My coolio.

Good meeting.. but I think we scared the leads.

After the monthly session, I’ve got some shit I need to get off my chest. Don’t take this the wrong way, man - I just want us to be real with each other and get our ducks in a row. We’re building something dope here, but we’ve gotta tighten up a few areas. Let me break it down for you:

1. I'm not feeling 100% stoked about where we're at right now. Seems like we've got some communication breakdowns and misaligned expectations happening. We need an open dialogue to hash this out and get on the same page.

2. This ain't gonna work if we're not crystal clear on how we make decisions and keep each other in the loop. We gotta establish some firm protocols for communicating and deciding on important shit, so no one feels left out or blindsided.

3. Time management is key, bro. I need to know how many hours you’re realistically putting into us versus your other ventures. We can’t let one effort overshadow the other - we’ve got to prioritize and balance our focus.

4. Speaking of priorities, let’s get that 5-page ventures plans locked down ASAP. And we need to align on our long-term vision, like nailing that $5M revenue target and making the 3 year forecast a reality. I know the 3 year thing is bullshit an may not come through but it’s a great lens. And back casting from 2026 is a good lens. Sensemaking and all that.

5. Your work has been solid, but we've got to step up the organization and summarization game. I'm not trying to be a dick, but those long, rambling lists ain't cutting it. Let's look into using some AI tools to help us think critically, summarize key points, and streamline our content.

6. Feedback and accountability are crucial in this game. I'll own up - I've dropped the ball on some commitments too. But we've got to get better at giving each other honest, constructive criticism and holding each other accountable for delivering.

7. I’ve got some ideas brewing that could be game-changers – things like individual grants, cool events like cool gnarly ai events, and potential revenue-generating projects. Let’s talk through these and see if they’re worth exploring further.

Look, at the end of the day, we're in this together. I'm not trying to rag on you or anything – I just want us to be real with each other, get our shit sorted, and keep pushing forward as a team. We've got something special brewing here, and I know we can take it to the next level if we stay focused and hold each other down.

Let me know when you want to grab a beer (or five) and hash this out, brother. I'm fired up to get this train moving full steam ahead.

Your partner in crime,
A Co-Founder, The Builder 👷🧰

Making it Work - AI Punks

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Rob Tyrie

Founder, Grey Swan Guild. CEO Ironstone Advisory: Serial Entrepreneur: Ideator, Thinker, Maker, Doer, Decider, Judge, Fan, Skeptic. Keeper of Libraries