How I Built (and Continually Refine) the Tech Stack That Runs My Life and Work

May 19, 2025

In entrepreneurship, there’s a common pattern I’ve observed and occasionally fallen into: the endless cycle of tool-hopping.

“Oh, I’ve got Notion, and then we’ll switch to Trello, and then we’ll move to Asana”—there’s this spin cycle where you can waste countless hours focusing on finding the “perfect” tool rather than making any actual progress.

How I Use My Tech Stack

What I’ve realized over time is that the tool doesn’t matter as much as the rules you put around it.

You and I can collaborate effectively on Trello, or we could do it with pen and paper.

The important elements are having a clear agenda before we check in, knowing you’ll respond to emails within certain timeframes, and other process elements.

The rules around the software are far more important than the tools themselves.

I’m always mindful that overly complex systems make tools less likely to be used.

Rather than chasing the next shiny object, I’d rather get really good at using my inbox or calendar.

Often, optimizing the tools you already have delivers more value than adopting something new.

My Core Productivity Tech Stack

Here is a list of apps in my core productivity tech stack.

Google Workspace: The Foundation

Most of my digital life revolves around Google Workspace. Gmail and Google Drive host 90% of my digital life, making me a frequent power user of these tools, along with Google Calendar.

This forms the backbone of my productivity system.

Calendar-First Project Management

If it isn’t on my calendar, it doesn’t happen.

While I’m starting to use tools like Trello and Asana for larger initiatives, Google Calendar remains my primary project management tool.

I read a book suggesting that successful people don’t rely heavily on dedicated project management tools; they use their calendar effectively.

This approach has provided me with tremendous comfort and clarity. I know that if I manage my calendar well, I’ll accomplish what needs to be done.

Everything goes in my calendar and gets adjusted as priorities shift.

As I bring on collaborators and tackle larger work projects, I do use additional specialized tools, but my personal management revolves around my calendar.

MixMax: My Email Superhero

MixMax is probably my number one tool – the one that makes a significant difference day to day.

This email management tool helps me in several key ways:

Reminders: I can set follow-up reminders directly in my inbox. If I want to circle back on something in six months, I can quickly set it to remind me at the appropriate time.
Send Later: This feature helps me schedule emails to send at future times, either as reminders or when I don’t want a back-and-forth exchange right away.
Smart Calendar Scheduling: The booking tool lets me embed specific available times directly into emails. I prefer this to tools like Calendly because it feels more personal—I can suggest specific times rather than forcing people to pick from a range of options.

At roughly $200 a year, MixMax is worth every penny because it transforms one of my least favorite tasks—scheduling—into a one-click action.

It’s a lightweight but powerful addition to my inbox ecosystem.

Zight: Screenshot and Annotation Expert

Zight (formerly CloudApp) is a screen capture and annotation tool similar to Loom.

I use it constantly—probably a hundred times a day—for screenshots because it lets me quickly capture, mark up, and share content.

It blows away the native screenshot tools on Mac or Windows with its simplicity.

The tool launches with a keystroke on both platforms and drops the link directly into whatever document or chat I’m working in.

It’s another example of my preference for tools that bolt onto systems I already use heavily.

Arc Browser: The Chrome Alternative

I’ve switched from being a heavy Chrome user to using Arc browser.

Chrome doesn’t play particularly well with Macs, and Arc seems to work better with my system.

Crucially, Arc still supports all my Chrome extensions, which makes the transition seamless.

Communication and Memory Tech Stack

Here is a list of tools for communication and memory.

Virtual Communication Improvement

I’m actively working on improving my virtual communication and presence using:

Poised / Microsoft Speaker Coach: These tools provide feedback by flagging when I’m using filler words or talking too fast.

I typically have Speaker Coach running during my work calls, while I use Poised more in my personal communications.

Relationship and Memory Systems

Timehop: Timehop is often the first app I check each day. It surfaces memories from photos, Facebook, Instagram, Twitter, and Swarm, helping me reconnect with friends through shared moments from the past.
Swarm app: I’ve been active on Swarm for over a decade, and it makes it incredibly easy to remember places I’ve visited. My parents are also avid users, so it helps me keep track of their travels too.
Sagan: Sagan is the agency I used to hire my Virtual Assistant. They provide training for general entrepreneurial skills, which has proven valuable beyond just the VA placement.

Learning, Focus, and Wellbeing Tools

Here is a list of tools that help me learn, keep focus, and ensure wellbeing.

Knowledge Capture and Retention

Readwise.io: Readwise.io tool pulls all my Kindle highlights and sends me a digest, making it effortless to revisit key passages from books I’ve read. It’s a fantastic way to reinforce important ideas over time.
Snipd podcast app: I recently started using Snipd and love how it lets me clip interesting segments from podcasts for easy sharing and reference. Its summary feature is also quite impressive.

Deep Work and Digital Mindfulness

Brain.fm: When I need to eliminate distractions and dive into deep work, I turn on Brain.fm. I grabbed a lifetime deal through AppSumo years ago and have found it remarkably effective for focusing.
Jomo: I’m working on being more mindful of my phone usage. Jomo helps me set boundaries and track my screen time. I’ve established limits for social media apps, which helps me stay focused and present in real life.

AI Integration and Future Directions

Here is a list of tools for AI and the future.

Current AI Usage

I’m actively exploring ways to integrate AI more deeply into my workflow.

Perplexity: I use Perplexity regularly for research, and I’m part of the Perplexity Business Fellowship. I’m deliberately trying to replace some of my habitual Google searches with Perplexity to become more familiar with AI tools.
Microsoft Copilot: Since my consulting job revolves around the Microsoft Suite, and considering my firm’s AI usage policies, I’ve become a frequent Copilot user. I mainly use it as a thinking partner but am beginning to explore its integration with Word, PowerPoint, and Excel.

For my day job at EY, I also use their internal EYQ program alongside Copilot.

AI Agents for Action: My Next Frontier

The area I’m most interested in exploring next is having AI agents that can take action for me.

While I’m comfortable using AI for research, I want to make the jump to tools that can go out and do things on the web—researching flights, handling LinkedIn outreach, or automating other tasks.

It’s essentially like needing a sophisticated scraper or crawler that can actually take meaningful actions.

Tools I Might Add to My Tech Stack

I have several specific tools I’m planning to explore:

Wispr Flow: My current laptop struggles with voice dictation, so I plan to try Wispr Flow once I get a new one.
Internet Pipes: I bought an Internet Pipes course years ago and want to finally dig into it.
Replit & Cursor: I’m trying to get more hands-on experience with AI coding tools, so I want to experiment with platforms like Replit and Cursor.

Tech Stack Security and Integration Challenges

Here are some of my challenges I’ve experienced with my tech stack.

The Interoperability Dilemma

What I’m increasingly craving is better interoperability between my various data silos.

Currently, my health data lives in one place, my work data in another, and nothing connects seamlessly. This creates friction when trying to use AI or other tools across these systems.

There’s a delicate balance between wanting everything to flow through a central system like G Suite for convenience while maintaining necessary separation for security-sensitive areas like banking.

Security Approach

I use two-factor authentication for most services. For my most privileged data sets, I rely on a dedicated authenticator app.

I’m conscious of the “honey pot” risk of centralizing everything under a single sign-on like G Suite, so I intentionally keep certain systems separate.

Conclusion

My tech stack will continue to evolve, but my principles remain consistent: embed tools where I already work, manage my life through the calendar, and let process rules—not flashy features—drive performance.

A quick recap of my favorite apps:

If a new app can clear these hurdles, I’ll give it a shot.

Otherwise, I’d rather master what I have than embark on another spin cycle of tool-hopping.

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