Virtual Assistants

I'm nowhere close to outsourcing half my life/work a la Ferris 4-hour work week... but my virtual assistants are an important and very appreciated part of my work life. Even though I've been using assistants for 3+ years now, I still find new ways to incorporate outsourcing into my daily routine.

Currently Using

Dedicated Assistants

After years of searching, I finally found several wonderful assistants whom I've been lucky enough to work with for the past few years. They're a brother/sister team I work with full-time and are incredibly diligent, respectful, and highly competent. I plan on working with them for years.


Looks similar to Twinsy's offering, but better pricing. Downside is that the assistants are not available through Messenger.

Seems like a promising alternative to a dedicated assistant should my workload wind down for whatever reason.

AND CO was recently acquired by Fiverr and started offering their solution for free. Lewis from The Freelance Effect saw this post and wrote about his experience with trying it. Although I do not freelance, this is something I've been recommending to friends who do.


Very sad about M being shuttered, although entirely understand Facebook's rationale (and also wonder why this didn't happen sooner). My friends at Facebook say: "ask in late January [2018]."

While Facebook has locked down access to it's true assistant pilot to the general public, I have loved using my M assistant since 2015. Hunter Walk puts it well in his "Virtual Life" post - Facebook M is best used for either immediate, time-sensitive tasks that are easy to perform or queuing tasks in advance for the assistant to perform at an appropriate time.

M has slowly become less and less flexible over the years (my obvious assumption: in an effort to structuralize and incorporate the conversational data into models that are universally applicable to all Messenger users), but still is the easiest and only free way to manage restaurant reservations, product discovery, and minor recurring research tasks.

Mezi is one of the assistants that have outlasted its competition in the nascent "conversational commerce" category. I have found Mezi to outperform all other assistants in both speed, reliability, and accuracy of identifying objects for purchase from photos. That said, I now only use Mezi for identification, and very rarely purchase through the service anymore.

Wonder is a slow but thorough research service. While not a dedicated individual, the Wonder team of researchers are able to deftly handle most complex requests for information. In the past, I have used Wonder for curiosities - often for data on industries, corporate financial reports, and putting together pitch decks. Wonder is particularly useful for areas where time is not important, but the quality of information integrity is; think investing, presentations, business plans.

It's easy to find the appeal in Upwork as a source of quality VAs. The talent is often the lowest price available on the market, and you get to pick from candidates who have been competing for your eyes. However, much like Zirtual, the process of upkeep, payments, etc. made it a challenge to integrate a true VA into my everyday life. Despite the challenges, Upwork remains the best and easiest way to find a wide range of global talent.

Put on temporary pause as I find the best way to delegate my time. Twinsy is an invisible team of assistants who complete tasks that are given and assigned via Facebook Messenger.

I have a whole theory on verticalized services and why this operating model will be the future of many service-based businesses. Alongside more well-known examples like Bench and And Co, Twinsy is one of the best examples of a product executing on this model.

I never know who completes my requests. I never know if it's an individual or a team doing the work. But Twinsy always has context and a real individual who works with me to ensure quality completion, almost as my de facto project manager.

By far, Twinsy has the most transparent and fair pricing model (currently $99/mo for 10 tasks) and most flexible team of assistants. Because there are real people who have been trained on handling specialized requests as opposed to bots, I get reliably good completion on my requests. I most often use Twinsy for research, outreach, lead generation, and data enrichment - stuff that I don't want to do but now can afford outsourcing.

Recently replaced with full-time assistant. I have known the founders, Maran and Michael, behind Clara for a few years now, and I have watched the product evolve significantly during that time. Clara is the best-in-class scheduling assistant. When my meeting calendar and email volume surges, Clara is a godsend - I'm comfortable looping in Clara to help coordinate a meeting. The only downside is I'm not willing to do it in an email thread where I don't have the leverage (often for sales or pitches), but I am happy to use Clara to coordinate almost any other meeting.

Operator is a beautifully-designed solution to a problem/need that I don't quite have: conversational commerce. As they pulled out of the USA to focus on a Chinese audience with a hungry appetite for American products, it seemed like this was a stronger direction for the service than purely focusing on finding products to purchase via conversation. I don't purchase products very heavily, so I'm likely out of the ideal demographic.

Magic started out as a novelty and... never quite left that category for me. While Magic has pivoted in the past to serve either a wealthy clientele or business clients, I have found it impossible to adapt into my daily life due to pricing. That said, recent price drops and its integration into a Slack team are compelling.

Along with the rest of the lesser-known providers of virtual assistants, Zirtual was a service that introduced the concept of outsourcing to the general public (popularized and romanticized early on by Tim Ferriss). I found that I would often spend more time managing the virtual assistants than I would get time back from them. Maybe my opinion would be different now, but email feels like a step backwards from chatting with assistants via Slack or Messenger.

Much like Clara, Amy is an assistant that you loop into email threads to coordinate the scheduling of an event. Unlike Clara, however, Amy is powered entirely by bots as opposed to of Clara's team of humans. It's very much a case of "machine intelligence" vs "human-in-the-loop." In this competition, HITL wins, by a massive margin.

I have used "Amy" on and off for the past three years, and I have seen both the quality of email interactions and the assistant's ability to "understand" responses decline signficantly. It just feels like a very premature product: even if X.ai is 3X cheaper than Clara, which it is, it just simply doesn't work and I'm not comfortable CC'ing Amy into any conversation.

Ringr was awesome when it used to work, but at some point in time the turnaround time just simply... disappeared. After responses began taking weeks vs days, I stopped.

I really never had a good experience using Service, ever. It didn't make sense to modularize the conversation experience into button options. They've since pivoted away from just issuing complaints and service requests into simply flight delays or cancellations, so it might be worth paying another visit.

Fin has undergone significant changes in the past couple years of its existence. Founded by Sam Lessin (Facebook VP Product + angel in my co, Fountain) and Andrew Kortina (Venmo cofounder), Fin is a digital assistant that can do significantly more than the average VA, rivaling an EA in scope. Alongside the normal set of requests like ordering products, setting reminders, and doing research, Fin can also reach out and schedule meetings w/ individuals on your behalf and coordinate hefty manual tasks like planning trips and paying bills. Fin also "learns and improves" dependent on your past conversations - while this is often a marketing gimmick, you can actually see this happening while using Fin: the assistant learns and records your contacts, notes, etc.

While I don't use Fin as often as I ought to, they now have one of the most compelling pricing models in the market: $1.00 per minute worked.