Why a startup founder still pays $1,000/month for a human assistant despite aggressively using AI in every corner of his life.
I'm an early adopter by nature, and I pretty aggressively use AI in most aspects of my personal and professional life:
I spend an hour a day on average talking to ChatGPT Advanced Voice Mode.
I typed the first drafts of this post using superwhisper, an AI speech-to-text tool.
I happily dished out $200/mo for OpenAI's Pro subscription as soon as it was released.
But despite all this, I still keep a remote personal assistant on our payroll for around $1,000 a month — and I don't see AI replacing her any time soon.
If you're curious about the kinds of work that human assistants can help with — and in particular, the jobs they can do better than AI — look no further.
Below is an incomplete list of things my assistant does better than AI can do them. I'll start the list with general roles that might be useful to a broad spectrum of entrepreneurs, then I'll get into tasks that are a little more specific to my personal workflow:
Supports travel-related administrative tasks: books good flights, Airbnbs/hotels
Proactively inspects my project backlog (Notion DB), finds tasks to help with, asks to help
Calls my pharmacy on my behalf to check on the status of prescriptions
Archives new books that I buy (~1/week) in Notion
Stays on top of irregular administrative tasks (e.g., taxes) and reminds me about them
Keeping my inboxes at inbox zero is probably the single most valuable thing my assistant does for me. If it were the only task she performed, I'd probably keep her on board for at least half of what I pay her. (Though to be fair, I really, really hate email.)
Keeps my personal email at inbox zero by labeling/archiving/replying at her discretion (or letting me know what needs a reply)
Keeps my professional email at inbox zero
Coordinates 1-on-1 meetups & events, then adds them to my calendar (via Notion Calendar)
The Indie Hackers newsroom publishes 5–10 articles every week. Here are some of the ways my assistant helps to project-manage this system:
Manages our editorial calendar (a database in Notion) by adding & scheduling content
Coordinates with newsroom journalists on upcoming content, i.e., project management
Creates cover images and newsletter GIFs for in-house content
Runs our Instagram account (recycles case study content published by newsroom)
Our forum is super active, and we have lots of algorithms (and even AI) in place to make sure the gems get uncovered and the spam gets hidden. But they don't do a perfect job. So here's how my assistant lends a hand:
Edits post titles according to our grammar conventions
Identifies and de-boosts low-value forum posts
Identifies and shadow bans bot accounts (our AI for this is imperfect)
We sell newsletter and website ads, but advertising isn't our main source of revenue or something we want to devote a lot of mindshare to. So I've outsourced most of the heavy lifting to my assistant.
Here are the things she does leading up to the sale of advertising placements as well as the things she does after a sale has been made:
When potential clients reach out with an interest in buying an ad placement, she guides them through the sales process
Often upsells clients to more expensive (but more appropriate) packages
Rejects nonsense offers before I ever even know about them
Workshops ad copy with clients, then directly updates the newsletter issue or the homepage with the final draft of the copy
Creates email previews (via Photoshop) for clients who buy our priciest newsletter ad
Manages back-and-forth coordination with BuySellAds, our sales partner
I've deliberately left out details about the service I used to find and hire my assistant because this article isn't about shilling for any specific company.
That said, I will share a few details about my assistant that I think are relevant:
She's Filipino and based in the Philippines, but she works 9 to 5 EST to align with my work hours
She's proficient in Photoshop and Figma, and she uses plenty of internally built AI tools to help her with writing tasks that require good English
She had prior experience working with tech execs before I hired her.
i dont think ai will replace assistants any time soon its more like ai makes a good assistant 10x stronger kinda like giving them iron man armor for boring admin stuff
Really resonates with me — no matter how far AI comes, there’s just a level of human judgment and proactive thinking that makes assistants irreplaceable. It reminds me a bit of solving riddles with kids: AI can spit out answers quickly, but part of the fun (and learning) comes from the human side — asking the right questions, making connections, and adding creativity that algorithms can’t fully replicate.
Great post! Curious, since email can be key to accessing financial resources (bank account, investment platforms..etc) do you have measures in place to protect yourself from getting hacked / robbed? $1000 isn't enough of a deterrent to keep someone away from a business bank account / investments.
Absolutely! Protecting access is critical, especially with how central email has become to financial and operational systems. One of the steps I recommend is delegating access through secure password management tools like LastPass. This ensures sensitive login credentials are never shared directly, and you can control permissions or revoke access at any time. In addition, enabling (2FA), using separate email accounts for financial matters, and regularly reviewing login activity are smart habits to stay ahead of potential risks.
Absolutely love this breakdown of what a great assistant can do. I'm also a heavy AI user—probably more than most, but there’s something about human initiative that AI just can’t replicate (yet).
Running a human version of Upwork with South African talent has left me torn between pushing further into AI or doubling down on what I already know works. The AI version of what I do is sitting in my head, half-built, but simultaneously, I know the human element still wins in ways automation can’t.
Curious—have you found any tasks where AI has actually outperformed your assistant, or where the two work together in a way that surprised you?
What a great post, man.
After 14 years with a team, running my marketing agency, I've been doing everything on my own again. It's been so interesting, back to writing, editing, filming, booking talks and workshops.
I am using a few tools, from BeeHiiv to ChatGPT and some scheduling tools, crazy to see how much money we end up spending.
Slowly I'm scaling back the team for very specific things, and now I'm in the process of hiring the VA from the Philippines with similar needs.
I think this post will be very helpful for anyone feeling a bit overwhelmed with work and not knowing how to delegate.
Thank you for this insightful post—your honest take on how AI still falls short of replacing a human personal assistant really resonates. It’s refreshing to see someone value the nuance, empathy, and connection that only a person can bring.
The reminder that “hype cycles move faster than product cycles” is something we’ve felt firsthand. In voice AI, it’s easy to get caught chasing every shiny new model, but the real wins come from solving the gritty, unglamorous problems that customers actually feel, latency, reliability, and trust.
Your emphasis on long-term foundations over short-term polish is spot on. Feels like the builders who stay disciplined on that front will be the ones still around when the noise fades.
AI is literally helping me build a million dollar brand and I cant say I believe a live human could work like this on my behalf.
I think we might be underestimating how fast this gap is closing. Tools like GPT-4 and custom workflows can already handling a lot of scheduling, summarizing, and drafting.
Exactly what I was thinking. AI is advancing so fast - the gap between today’s AI and just a year ago is huge, not to mention what we’ll see in 3, 4, or 5 years. Even highly skilled assistants might soon be replaced by AI at this rate.
Thank you for writing this post. I am an Executive Assistant myself and I always get the question: Aren't you scared of losing your job because of AI?
Reading your reasons about why a human assistant is valuable, I feel more secure about the value I bring to my executives.
But just to be aware, what tasks related to this job is AI helping you with at the moment?
A well-observed and shared story of being kept up with EA or PA for daily operational assistance tasks being taken care of by the latter, as per my personal observation i do have 3 EAs under me doing the same thing for other ventures, keeping pace with operational leaders for regular updates in a summarized way for all of the chaos if i am going to handle it myself, to them i have given 4 days work week rotational shifts for better productivity and lesser leaves with strict policy emergency.
Totally agree. AI helps a lot, but there’s always a bit of human touch in everything we do—because some things just need that personal vibe.
how to apply for a VA, i am currently looking for a role EITHER VA/ project manager! Please reach out over email if anyone has any opportunities. over email - inayahk712@
Totally get it, AI tools are handy, but they still miss that human touch and flexibility a real assistant brings. Not surprised they’re not quite there yet.
A.I is great too but I'm impressed by your personal assistant dexterity. I didn't see only your personal assistant qualities here ; I see values .
Thank you for crafting this .
Great post! I agree that AI will continue to improve, but I don't see its growth following a straight, linear path. Instead, I believe it will follow on — accelerating rapidly, then eventually leveling off as it becomes fully integrated into our daily lives and work routines.
Great post. I also think AI is only bound to get better, but I don't think it will take the same linear progression, I think it will be an S-curve growth like most things in life. It will plateau at some point when we've worked it into our daily or work tasks as much as possible.
I love using my AI partners, but there are times, when human is the best or even only option, so I appreciate the breakdown and the reminder that AI and humans as partners is the best option.
Some valid points here!
Great post
AI is powerful but lacks the human touch. A personal assistant offers emotional intelligence, nuanced decision-making, and adaptability. For a startup founder, these qualities are invaluable for managing complex tasks and providing personalized support that AI alone cannot replicate.
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AI will not replace human anytime soon. A lot of people are talking about how it will but when you really think how adaptable humans are and what we can do, machines can just help them become better.
Absolutely agree on the fact that human factor can't be replicated by AI.
I agree with you Alex. AI will only help humans work better.
This is a great breakdown of how human assistants still outperform AI in key areas. While AI is excellent for automation, a skilled assistant brings proactive thinking, nuanced decision-making, and adaptability—things AI still struggles with.
Your point about inbox management resonated with me. AI can categorize and summarize emails, but a human assistant understands context and relationships, making prioritization much smoother. The same applies to tasks like sales support and forum moderation—AI can assist, but a human touch ensures quality control.
For those balancing automation with human assistance, a hybrid approach seems ideal. I use AI for repetitive tasks, but when it comes to optimizing workflows or handling nuanced customer interactions, having a human assistant remains invaluable.
I also use AI to automate my. First i did not get too much response from them. Now, i am used to it and handle my business as startup. and in the future planning to expand it.
Would love to hear your thoughts—do you see AI evolving to handle some of these high-level tasks more efficiently in the near future?
I completely agree with you Channing. So much so that late last year I was starting up (but never got off the ground) a VA agency that specialized in experienced assistants that are also well-versed and trained in AI.
Looks like that was a good idea after all 🤦♂️
Also there's another argument to made In favor of, regarding talent and the future of the workforce. People in 3rd world countries are going to have fewer and fewer means of earning an income. I think AI up-skilling like this can help alleviate some of that.
That’s a really interesting point! A VA agency specializing in AI-trained assistants would have been ahead of the curve—there’s still a huge demand for skilled human assistants who can leverage AI effectively. Rather than replacing jobs, AI is transforming them, and those who adapt will stay valuable in the workforce.
I also agree that AI upskilling can create new opportunities, especially in developing countries. Instead of AI replacing jobs, it can empower people to work smarter and provide higher-value services. The key is striking the right balance—using AI for automation while relying on human expertise for decision-making.
It’s great to see more discussions around this. Have you considered revisiting the VA agency idea with a stronger AI focus? The demand for AI-enhanced virtual assistants seems to be growing rapidly!
I have not...I think there's far too much I don't know about a staffing agency business like this and a major problem I see (with no real solution) is churn. Attrition of talent between agencies/freelancing/clients seems to be the biggest thorn in agency owner's sides. I think it can be "solved" from the client's perspective where VA's tend to stay with a client for a while, but eventually having an agency in the middle becomes more of a burden than a benefit.
Another idea I had was an upskilling consultancy that would come into existing agencies and upskill their VA's with new AI skills and tools for a fee.
Along with that you could develop your own AI tools (just a nice consolidated UI/UX essentially) that makes VA's jobs easier and sell that to individual VA's or agencies as well. Honestly going this route may be the easiest.
AI has made significant strides in recent years, but it is still far from replacing a personal assistant. One of the key reasons for this is emotional intelligence; while AI can process data, it lacks the ability to understand or respond to emotions in the nuanced way a human can. A personal assistant can gauge your mood, adapt their tone, and offer empathy, something AI struggles to replicate. Additionally, AI doesn't have the same level of contextual understanding as a human; it often struggles with complex or ambiguous situations that require a deeper grasp of the broader context.
Another important difference is creativity—AI is excellent at processing and analyzing existing information, but it doesn't possess the true creativity and innovative problem-solving abilities that a human assistant can offer. Personal assistants also learn from experience, building relationships and adapting to your needs over time, whereas AI's ability to evolve is limited.
real way
I’m the founder of https://getinboxzero.com. Curious if you or your assistant has tried it? Where does it fall short for an ai replacing a human for reaching inbox zero?
you r amazing
I disagree as I recently lauched an AI OS to replace assistants, sign up for the waitlist here if interested.
Do you work with an assistant? Have you in the past?
I totally agree with Channing! AI is great, but a human assistant brings intuition, adaptability, and proactive problem-solving that AI just can’t match. Inbox management alone is a lifesaver! This article perfectly captures why both AI and human support are valuable.
Completely agree! AI is great for efficiency, but when it comes to context, judgment, and handling dynamic situations, human assistants are irreplaceable. Even in UX/UI, AI tools help, but they can’t replace real problem-solving and empathy-driven design.