The road to $10M (from a Chief of Staff in NYC!)

Listen now:
Spotify // Apple // YouTube

Sawyer Middeleer is Chief of Staff at Omni, an AI startup with just four people aiming for $10 million in yearly revenue. He's also an AI systems builder and startup operations expert who leads business development and automation strategy. Before this, he worked for several years in city planning, real estate, and strategy roles across nonprofits, government, and private companies. His work included community engagement, financial planning, and smart cities technology projects. Sawyer also lived and worked in China, where he taught high school history and English while researching urban development. He's been learning Mandarin for 15 years and now speaks it fluently!

What you'll learn:

1. How to learn new skills by jumping in first, then studying - this builds deeper understanding than following tutorials

2. Why connecting AI tools to Notion creates powerful automation without needing technical skills or complex systems

3. How small startups can reach $10M revenue with fewer than 10 people using generalist team members and AI tools

4. Why "context engineering" is the secret to building AI agents that stay smart throughout their work processes

5. How to start with simple AI automations like email sorting and lead generation that give quick wins

6. Why tools like Lovable now let anyone build custom apps just by describing what they want in plain English

7. How combining different skills creates better career opportunities than becoming an expert in just one area

8. Why following your interests beats trying to predict what skills will be valuable in the future

Some takeaways:

Learn by doing first, then studying. Jump into new areas through hands-on practice before reading manuals or taking courses. This trial-and-error method helps you understand not just what works, but why it works. Sawyer used this approach to learn Mandarin over 15 years and to master AI development from the very beginning.

Use Notion as your AI control centre. Instead of building complex tech systems, connect AI tools to Notion databases. The AI can read from and write to your Notion pages, handling content updates, knowledge management, and testing without needing a programmer. This lets non-tech leaders deploy smart automation easily.

Build lean teams of multi-skilled people, not big specialist departments. Omni runs with four people targeting $10M revenue by hiring exceptional generalists who can do multiple jobs. Their team has a technical founder, an engineer who also does product design, a growth expert, and a chief of staff who handles operations, sales, and customer support. AI tools help each person do much more.

Master context engineering for better AI performance. The key to effective AI tools is managing what information they can access during their work. Use knowledge systems as "libraries" that AI agents can reference and update. This keeps information consistent and prevents AI performance from getting worse over time.

Start with simple automations that give quick wins. Email sorting agents, lead generation tools, and support ticket analysis provide immediate benefits with easy setup. These applications show clear value quickly and help teams understand what AI can do before building more complex systems.

Build custom software without coding skills. Tools like Lovable let anyone create working applications by describing what they want in normal language. This means individuals and small teams can solve specific problems without buying generic software or hiring expensive developers.

Combine skills instead of specialising deeply. Create unique career value by getting good at several related areas rather than becoming the best at just one thing. Sawyer's mix of leadership, sales, and coding skills creates opportunities that few people can fill. This approach gives more career flexibility and higher value to employers.

Follow your interests instead of guessing future trends. Rather than trying to predict which skills will matter, explore what genuinely interests you right now. Technology changes so fast that long-term planning is less valuable than staying curious and adaptable. New problems always emerge that need people who can solve them.

Aim for higher revenue before raising big funding rounds. The bar for Series A funding has jumped from $1-2M yearly revenue to around $10M, especially for AI companies. Success now means finding the right market and perfecting your product with a small team before hiring lots of people. This model works well for adaptable generalists.

Links:

Where to find Sawyer

• Linkedin: https://www.linkedin.com/in/sawyer-middeleer/

Where to find Milly

• Linkedin: https://www.linkedin.com/in/milly-tamati/

• Website: http://www.millytamati.com/

Generalist World resources:

• Podcast on Spotify: https://open.spotify.com/episode/50ypfms2omRqdjTe5Y6aPK?si=708eba329b304f20

• Podcast on Apple: https://podcasts.apple.com/us/podcast/the-road-to-%2410m-from-a-chief-of-staff-in-nyc/id1814092399?i=1000720094017

• Podcast on YouTube: https://youtu.be/k-G1Sh1biOE

• The Generalist Quiz: https://www.generalistquiz.com/

• The AI fluency Quiz: https://www.aiskillsquiz.com/

• Essays: https://www.generalistcareer.com/

• Upcoming events: https://lu.ma/generalist.events

• Positioning Guidebook: https://www.generalist.world/positioning

🙏 Special thanks to our podcast producer James McKinven! (get in touch for all your podcast needs, he’s really great!)