Redirecting.work

What Did He Pivot From?
Nelson’s early career began on the field—video, data, and performance analytics for Major League Baseball organizations (Cincinnati Reds, Tampa Bay Rays, Toronto Blue Jays summer affiliate) and later inside the Cleveland Guardians. A unique internal move there shifted him from player analytics to supporting the staff who support the players; an L&D- and people-analytics–flavored role that measured needs, learning preferences, and the realities of a year-round season. He also spent time at Major League Soccer’s league office in New York in a data strategy role. The 2023 tech layoffs, a grueling search, and a misfit role that ended in termination forced a hard reset. Therapy, reflection, and a candid inventory of strengths led him to ask different questions: What do I want to keep learning? Where do I want to spend my energy? What can I build?

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Current Direction
Today Nelson runs a portfolio career that blends several AI-forward lanes:

• Consulting for organizations just getting started with AI, setting their foundations and providing change management.
   

• Advising HR tech and future-of-work startups on product strategy and practical AI use cases, balancing builder and practitioner perspectives.
   

• Software development using AI to ship custom tools. An example is he’s built a community platform that turned manual “I heard about a job” chatter into structured opportunity sharing.
   

• Speaking on AI and the future of work (e.g., an IPAC keynote).
   

• Media via newsletters that mix curation, analysis, and original ideas, monetized through sponsorships and paid tiers.

 

He’s also pursuing an MBA at Columbia, pairing business frameworks with the lived experiment of an AI-enabled solo enterprise. Rather than fixate on endpoints, he measures success by showing up consistently and doing the real work daily. The output follows.

 

AI Toolkit & Workflow (How He Scales Himself)
Nelson’s operating system, an AI entrepreneur’s ecosystem, is built around Obsidian as a hub, where recordings, notes, and artifacts land automatically. He relies on AI agents inside Obsidian plus Cursor and Claude to clean up, sort, and make sense of inputs, especially meeting summaries and project notes, all while keeping human judgment in the loop for creative work. Use of a newer protocol, MCP (Model Context Protocol), lets his AI tools “talk” to other apps, so tasks chain together without manual copying.

For projects and product work, he uses Linear to track tasks across all ventures in one place. Calendars from multiple accounts roll up to a single availability view. For research sprints where he provides tool comparisons, business models, and market sweeps, he leans on Perplexity to compress hours of scanning into minutes of direction. And for speed, he “rarely types” instead, using Wispr Flow (cloud) and Monologue (on-device) to convert voice to text so ideas move fast from thought to artifact with privacy options when needed.

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Importantly, Nelson distinguishes automation for administration (e.g., summarizing and filing meeting notes with no human in the loop) from automation for creation (where he keeps his hands on the wheel). AI moves the bricks; he designs the house.

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Mindset Shifts
Setbacks—finishing second in interviews, the layoff, the firing, were catalysts. Therapy and honest self-assessment helped him redefine identity and ambition. He now monetizes what he’d do anyway: exploring AI and building useful things. The mantra he shares often: planning to do the thing is not doing the thing; organizing around the thing is not doing the thing; the only thing that is doing the thing is doing the thing. His work and life embodies a new future of work paradigm.

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Advice to Others

For those wanting to be a solo entrepreneur, specifically augmented by AI and focused on AI deliverables, he says:

• Go deeper with curiosity. Use AI not just to brainstorm but to prototype, compare models, and test offers.
   

• Combine AI with your strengths. The multiplier appears when you fuse your domain edge with modern tools.
   

• Build before you leap. If you’re in a corporate role today, use AI to stand up side projects such as courses, apps, and playbooks so you have traction before a switch.
   

• Design your systems. Map the processes you repeat (sales, delivery, content) and wire them with AI-enabled automation. Save your energy for the uniquely human parts.
   

• Execute. Ideas compound only when you ship.

 

In the end, Nelson’s pivot isn’t a rejection of the corporate path so much as a redesign of agency. He’s assembled a system where AI takes on the repetitive strain while he invests his attention in the human work that matters most: curiosity, relationships, and making useful things. The result is a portfolio that feels both sustainable and expansive: learning as a habit, execution as a practice, and enough structure to keep moving as his model of the future of work continues to unfold.