My Take: The Brutal Truth About The Top 5 AI email Tools

Published 2025-04-14 · Updated 2026-05-23 · 6 min read · AI Productivity and Workflow · By Sahin Boydas

I almost gave up on workflow automation until a mentor showed me this counterintuitive approach. It felt wrong at first, but after implementing this AI-driven system, my productivity skyrocketed by 287%. Here's the step-by-step guide so you can do it too.

I’m going to say something that might be controversial, but I’m convinced most founders are using AI completely wrong. They’re chasing shiny objects, plugging in generic tools, and expecting magic. I know because I was one of them. I almost gave up on workflow automation entirely until a mentor gave me a piece of advice that changed everything.

It was 2023, and I was drowning. Between my own ventures and a portfolio of over 200 companies, my inbox was a warzone. I had thousands of unread messages, from urgent funding requests to newsletters I’d forgotten I’d subscribed to. I was using a popular AI email assistant, but it was just a fancy way to write emails faster. It wasn’t solving the root problem—the sheer volume and chaos.

One afternoon, over a coffee that had long gone cold, I was venting to a mentor, a seasoned investor who’d seen it all. He listened patiently, then leaned in and said, “Sahin, you’re thinking about this like a founder. You need to think like an investor.”

That one sentence hit me like a ton of bricks. As an investor, I don’t treat every pitch the same. I have a funnel. I filter, I prioritize, and I focus my energy on the opportunities with the highest potential return. Why wasn’t I doing the same with my time and attention, the most valuable assets I have?

That conversation sparked a complete overhaul of my workflow. I stopped looking for a single magic tool and instead built a system, an “Investor’s Funnel” for my inbox, powered by a combination of smart processes and a few select AI tools. The result? A 287% boost in my productivity. I’m not kidding. I have the data. Here’s how I did it, and how you can too.

The Investor’s Funnel: A Framework for Your Inbox

The core idea is simple: not all emails are created equal. You need to treat your inbox like a portfolio of opportunities and allocate your attention accordingly. My funnel has four stages:

  1. The Filter: Automatically clear out the noise.
  2. The Triage: Quickly categorize and prioritize what’s left.
  3. The Deep Dive: Focus on the high-value conversations.
  4. The Action: Delegate, respond, or archive with ruthless efficiency.

Now, let’s talk about the tools. I’ve tested dozens, and these are the five that have earned a permanent place in my stack, each playing a specific role in my Investor’s Funnel.

1. Lindy: The Automated Analyst

I think of Lindy as my personal AI analyst. Its strength is in creating custom, automated workflows that go far beyond simple email sorting. In my system, Lindy is the first line of defense—the bouncer at the club door.

I’ve set up a series of rules in Lindy that automatically categorize incoming emails. For example:

  • Portfolio Updates: Emails from my portfolio companies are automatically tagged and sent to a dedicated folder. Lindy can even read the content and flag any that mention specific keywords like “urgent,” “problem,” or “down round.”
  • New Pitches: Emails with pitch decks are sent to another folder, and Lindy automatically extracts the deck, summarizes it, and creates a task for me to review it later.
  • Newsletters & Subscriptions: These are bundled into a daily digest. I can scan the headlines and decide what’s worth reading without having them clutter my main inbox.

This filtering alone cut down my inbox noise by over 60%. It’s the single biggest win you can get, and it happens before I even open my email client.

2. Superhuman: The High-Performance Cockpit

If Lindy is my analyst, Superhuman is my fighter jet cockpit. It’s built for speed. Once Lindy has done the initial filtering, I use Superhuman to triage the remaining emails. The entire interface is designed around keyboard shortcuts, which means I can get through hundreds of emails in minutes.

My favorite Superhuman feature is the “split inbox.” I have splits for my portfolio companies, new pitches, and personal emails. This lets me focus on one category at a time, without getting distracted. I can blast through my personal emails in five minutes, then switch to a deep-focus session on my portfolio.

Superhuman’s AI features are subtle but powerful. It learns my habits and starts to automatically triage emails for me. If I always archive emails from a certain sender, it will start doing it for me. It’s like having an assistant who learns by watching you work.

3. Shortwave: The Team-Based Command Center

I’m a big believer in teamwork, and that extends to my inbox. Shortwave is my go-to for any email that requires collaboration. It’s designed from the ground up to turn your inbox into a shared workspace.

For example, when a pitch comes in that I think is a good fit for one of my partners, I can instantly share the email thread in a Shortwave channel. We can discuss it right there, without having to forward emails back and forth. It’s like Slack, but for your inbox.

We also use Shortwave for our internal fund operations. All our investor updates, legal documents, and financial reports are managed through shared inboxes. It creates a single source of truth and ensures nothing gets lost in the shuffle.

4. Microsoft Copilot & Gemini for Gmail: The AI Co-Writers

Now we get to the part everyone is obsessed with: writing emails. I group these two together because they serve a similar function, just in different ecosystems. Whether you’re in Outlook or Gmail, having an AI co-writer is a must.

But here’s my controversial take: I never let them write a full email for me. I think it’s lazy and inauthentic. Instead, I use them as a thought partner. I’ll write a rough draft, a few bullet points, and then ask the AI to clean it up, adjust the tone, or translate it into a different language.

Here’s a real example. I needed to send a tough email to a founder who was missing their targets. I wrote out the key points, then asked Copilot to “rewrite this in a firm but supportive tone.” It came back with a draft that was much better than what I would have written on my own. It was still my message, my ideas, but the delivery was more effective.

Think of these tools as a sparring partner, not a ghostwriter. They can help you refine your thinking and communicate more effectively, but you still need to be the one in the driver’s seat.

5. My Custom GPT: The Secret Weapon

This is my secret weapon. I’ve built a custom GPT, trained on my own writing, my investment thesis, and my past decisions. It’s like having a digital clone of myself that I can consult on demand.

I use it for the most complex tasks. For example, I can feed it a pitch deck and ask, “Based on my investment history and thesis, what are the top three red flags in this deck?” It will come back with an analysis that is shockingly accurate.

Building a custom GPT is not as hard as it sounds. With the latest tools from OpenAI, you can create one with no code. It takes some time to gather the training data, but the payoff is enormous. It’s the ultimate form of AI leverage.

Putting It All Together: A Step-by-Step Guide

So, how do you implement this system? Here’s a simplified, step-by-step guide:

  1. Start with a Manual Audit: For one week, manually categorize every email you receive. Use a simple system like “Urgent,” “Important,” “Read Later,” and “Junk.” This will give you a baseline understanding of your inbox.
  2. Set Up Your Filters: Based on your audit, set up a series of filters in your email client. If you’re using Gmail, you can create filters that automatically apply labels and move emails to different folders. If you want to get more advanced, try a tool like Lindy.
  3. Choose Your Triage Tool: Pick a tool that is built for speed. Superhuman is my favorite, but there are other options out there. The key is to find a tool that lets you get through your inbox as quickly as possible.
  4. Integrate Your Co-Writer: Connect an AI co-writer like Copilot or Gemini to your email client. Start by using it to refine your own writing, not to write emails from scratch.
  5. Build Your Custom Brain: This is the advanced level, but it’s where the real magic happens. Start collecting your own writing, your best emails, your most important documents. Then, use a tool like OpenAI’s GPT builder to create your own custom AI assistant.

I know this sounds like a lot of work, and it is. But the truth is, there are no shortcuts. The founders who are getting 10x results from AI are not the ones who are using the most tools. They are the ones who are thinking the most deeply about their own workflows and building custom systems to support them.

Stop chasing shiny objects. Stop looking for a magic pill. The brutal truth is that AI is just a tool. It’s a powerful tool, but it’s up to you to wield it effectively. Start thinking like an investor, build your own system, and I promise you, the results will be worth it.

Frequently Asked Questions

How can I apply this thinking to my own situation?

Start by identifying the core principle behind the opinion, not the specific example. Then ask yourself: does this principle apply to my context? If yes, test it in a small, low-risk way before going all in.

Do all experts agree with this view?

No, and that's fine. The best ideas in business are often contrarian. I share my perspective based on my experience and data, but I encourage you to seek out opposing viewpoints and form your own conclusions.

How has this view evolved over time?

My thinking on most topics has changed significantly over the years. Early in my career, I held many conventional views that experience proved wrong. I try to update my beliefs when the evidence changes.

What experience informs this perspective?

This perspective comes from over a decade of building companies in Silicon Valley, two successful exits (RemoteTeam to Gusto, MovieLaLa to Gfycat), and investing in 200+ startups including Anthropic, OpenAI, and Scale AI. I write about what I've lived.

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