Squirrel Squadron Substack

The Squirrel Squadron Substack blends insights on technology, leadership, and management, targeting tech and non-tech executives. It emphasizes collaboration between humans and AI, encourages questioning norms, and seeks to enhance team dynamics and innovation through strategic experimentation, intelligent disobedience, and understanding the business value in tech initiatives.

Technology and Innovation Leadership and Management Team Dynamics and Culture Strategic Planning and Execution Artificial Intelligence and Human Collaboration Software Development and Engineering Practices Product Management Business Strategy and Value

The hottest Substack posts of Squirrel Squadron Substack

And their main takeaways

Centaurs and the Future of AI

1 HN point • 01 Jun 23
  1. Computers and humans work best together, not separately.
  2. When using AI, consider the computer as a 'method actor' in conversations.
  3. Incorporate humans in the loop with AI for better results, especially in operational processes.

🐿️ Hardening - The IPT Newsletter

0 implied HN points • 17 Jun 25
💼 Business Customer Service Product Management Software Development Marketing User Experience
  1. Fixing problems quickly makes a strong impression on customers. If a hotel or service handles issues well, people remember that positively.
  2. Customers are often less upset about mistakes if they see prompt and effective solutions. It's more about how you respond to problems than the problems themselves.
  3. In today's tech world, many people face constant bugs and bad user experiences. If you can help them easily, you'll stand out and earn their loyalty.

🐿️ Horns - The IPT Newsletter

0 implied HN points • 17 Jun 25
💼 Business Management Communication Agile Productivity Technology
  1. In New York City, car horns are used for many reasons, not just to express annoyance. They help communicate traffic situations quickly.
  2. Drivers in NYC often resolve conflicts fast by using their horns, while in other places, politeness can slow things down.
  3. Creating clear ways to share information, like dashboards, can help teams work better together and solve issues faster.
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🐿️ Recapitulation - The IPT Newsletter

0 implied HN points • 17 Jun 25
🕹 Technology Software Systems Innovation Engineering Culture
  1. Technology often has parts that look fragile but work together well. By understanding these 'contraptions,' we can better appreciate their value and reliability.
  2. Old computer systems sometimes carry outdated functions, making them act like their ancient versions. This shows how technology can evolve but still keep old elements alive.
  3. People often create makeshift solutions that can work surprisingly well, even if they're not ideal. These 'kludgy' setups remind us that not all systems need to be perfect to serve their purpose.

🐿️ Slow Turbo - The IPT Newsletter

0 implied HN points • 17 Jun 25
🕹 Technology Software Computing Internet Networking Programming
  1. Old computer hardware had a 'turbo' button, which was actually used to slow down the computer. This was necessary because faster computers could run programs too quickly for users to keep up.
  2. Modern software adapts to different speeds, but older systems can be very sensitive to changes. Even small updates need careful consideration to avoid issues.
  3. When software has many connections, even simple improvements can cause problems. It's important to simplify these connections to keep things running smoothly.

🐿️ Inspector Gadget - The IPT Newsletter

0 implied HN points • 17 Jun 25
🕹 Technology Software Engineering Design Systems Innovation
  1. Many technologies and systems are complicated and work just barely, like funny gadgets. They often rely on many small parts working together, even if they look messy or fragile.
  2. Rebuilding a system from scratch can make you lose important fixes and adaptations that made it work. It's better to replace parts slowly to improve it while keeping it running.
  3. Even though we think of computers as well-designed, many are actually put together in tricky ways. This is especially true for old software that can be a confusing mix of different ideas.

🐿️ Hamurabi, Think Again - The Insanely Profitable Tech Newsletter

0 implied HN points • 07 Jan 25
🕹 Technology Software Gaming Product Development Education Innovation
  1. Learning through experimentation is key to understanding complex problems. Just like playing a game, you need to try different approaches to find what works.
  2. In product development, there are guidelines but no strict rules. It's important to keep adjusting your methods based on what you discover during the process.
  3. Don't expect smooth and easy paths to success in tech. Expect to face challenges and changes, and use them to refine your strategies.

🐿️ The Three Laws of AI - The Insanely Profitable Tech Newsletter

0 implied HN points • 07 Jan 25
🕹 Technology AI Productivity Coding Innovation Automation
  1. It's best not to let AI talk to customers directly, as this can lead to funny but unprofessional mistakes. Keeping AI behind the scenes helps avoid embarrassing situations.
  2. Be cautious about ownership of what AI creates. It's important to have a backup plan if the AI's content turns out to belong to someone else.
  3. Always double-check what AI tells you. AI can produce boring or incorrect information, so having a human oversee its work can help keep things interesting and accurate.

🐿️ Those Magnificent Men In Their Flying Machines - The Insanely Profitable Tech Newsletter

0 implied HN points • 07 Jan 25
🕹 Technology Aerospace Engineering Innovation Space Industry Tech startups
  1. Experimentation is key to learning. Just like early aviators learned from their crash attempts, businesses can benefit from trying new things and learning quickly from failures.
  2. SpaceX took more risks and embraced failures, which helped them succeed faster. They learned from their explosions, while Boeing took a safer approach and faced delays and high costs.
  3. In software development, mistakes can be less costly than in aerospace. Companies should feel free to experiment and gather feedback from users to improve their products, just like SpaceX does.

🐿️ The Thinker Thinks, The Prover Proves - The Insanely Profitable Tech Newsletter

0 implied HN points • 07 Jan 25
💼 Business Marketing Sales Leadership Psychology Productivity
  1. People have two main mental roles: the Thinker, who comes up with ideas, and the Prover, who searches for proof of those ideas. It's important to realize that the Thinker leads the way.
  2. If you want to persuade someone, focus on connecting with the Thinker first. This means building trust and understanding their feelings rather than just presenting facts.
  3. When trying to sell a product or convince a team, emotional storytelling can be more effective than logical reasoning. People often need a narrative that resonates with them before they look for evidence.

🐿️ Procrustes - The Insanely profitable Tech Newsletter

0 implied HN points • 07 Jan 25
🕹 Technology Software Development Project management Client Relations Business strategy Product Design
  1. When faced with too many demands, focus on solving the customer's most important problems first. It’s better to tackle what's truly necessary rather than trying to please everyone.
  2. Communication is key. A skilled account manager can help manage expectations and guide clients toward what they actually need instead of what they want.
  3. It’s important to distinguish between essential requirements and nice-to-have features. This clarity can help teams deliver projects successfully and on time.

🐿️ Riding the Current - The Insanely Profitable Tech Newsletter

0 implied HN points • 07 Jan 25
🕹 Technology AI Hardware Software Computing Innovation
  1. Smartphones today have much more power than computers from just 25 years ago. This shows how quickly technology improves, with more parts being added to chips every few years.
  2. There’s a slowdown coming in AI growth because we need special, big computer systems to run these complex programs. As we reach limits in technology, we might have to focus more on improving software instead of just making computers faster.
  3. Even though AI is advancing quickly, there are challenges like the lack of special chips and the environmental impact of new data centers. This means the future of AI development might not be as fast as we expect.

🐿️ YOU! - The Insanely Profitable Tech Newsletter

0 implied HN points • 07 Jan 25
💼 Business Leadership Management Teamwork Productivity Corporate culture
  1. In emergencies, everyone looks to others to act, so it helps to designate someone in charge to break the inaction. This was seen when a bystander gave orders at an accident scene, leading to quicker help for the injured.
  2. Teams often struggle with accountability because they wait for someone else to take responsibility. Setting clear roles and deadlines can help prevent this issue.
  3. Encouraging a culture where everyone feels empowered to take initiative is important. The key is to reward those who step up, as taking action is better than doing nothing at all.

🐿️ Greatest Fried Chicken - The Insanely Profitable Tech Newsletter

0 implied HN points • 07 Jan 25
🕹 Technology Innovation Startups Business Models Product Development
  1. Some businesses may look good from the outside but can be ineffective or even fronts for illegal activities. It's essential to look deeper to understand their true operations.
  2. Large organizations often struggle to innovate because new ideas can threaten their current success. This results in a culture that rejects new inventions.
  3. Investments in new 'innovation centers' often serve to make companies look good, rather than genuinely foster innovation. This leads to a lot of effort going into appearances rather than actual progress.

Flying Blind: Your Tech Instrument Panel - Squadron Weekly Email

0 implied HN points • 11 Dec 23
🕹 Technology
  1. Having the right instruments in your tech projects is crucial for staying on course.
  2. Key instruments to track progress include radar system, glidepath indicator, stall warning, ground proximity warning system, and cabin CCTV.
  3. Many teams and projects are not monitoring all these key indicators, leading to potential issues.

Having Fun: The Key To Tech Team Profit

0 implied HN points • 25 Oct 23
🕹 Technology Software Engineering Creativity Culture Business
  1. Software engineering teams should bring excitement and fun to the workplace to motivate developers and increase creativity and profitability.
  2. In complex systems like software, relaxation and fun can lead to better problem-solving and creativity.
  3. Encouraging experimentation and taking appropriate risks can lead to innovative solutions and success in technology teams.