A guy
Before the internet, you had a guy.
A guy for your health—the local doctor who really knew you. Saw you for check-ups, kept tabs on you, ran into you at the grocery store, was there for your mother-in-law’s funeral.
A guy for your money—an accountant down the street who helped you file your taxes, keep the books balanced, and gave advice on investments and business opportunities.
A guy for your travel—someone who helped you book your flights, find the best hotel, rent the car, manage travel disruptions, and snag you good deals.
Few people anymore have a guy for anything. This role that used to be so important to our day-to-day lives—the trusted advisor—has all but vanished, leaving us empowered (yay) but also forced to fend for ourselves (boo). Turns out, these “guys” actually did a lot of work.
Sure, it’s great that you can book your own flights! But you also have to keep track of your rewards points, find the best deal, figure out if that layover is long enough or not, remember the checked bag policy, and manage your own backup plan if flights are canceled or delayed.
It’s awesome that you can invest on Robinhood and TurboTax your way to a modest return! But you also have to do your own research, take full responsibility for the risks and downsides, and keep track of all your own paperwork throughout the year to make sure you don’t fuck up your taxes and draw the evil eye of the IRS.
The experience of a speedy virtual care appointment, followed up with a Capsule delivery of your prescription, can be utterly magical, especially when you are feeling rough. But if you want someone who understands the long-term arc of your health, the chronic issues you may be dealing with over the course of months and years, and who is motivated and invested in your long-term preventative care… well, good luck. And don’t get me started on WebMD-induced hypochondria.
The internet gave those of us craving agency the ability to just do it ourselves, and that’s a miraculous thing. Disintermediating from “the guy” to book your flights is, in many ways, absolutely good. But it means we’re all shouldering a load far greater than generations prior, even as the world gets more complicated and stressful, and technology keeps threatening our health and sanity in new ways seemingly every day.
AI, of course, wants to fill the trusted advisor role, and in some ways it can. I work with AI every single day, and for me it’s more of a trusted advisor than it is for most people. I still think there’s a role for humans to play. AI is fast and it never sleeps, but it doesn’t read the room… the body language, the emotion. And it will be a while—if ever—before most people can both trust and harness it in ways that actually lighten the load. Right now, my bet is that AI feels like just another stressful thing to contend with, and it lacks the warmth most of us would love in a partner we trust with our health, our money, and our leisure.
Unfortunately, the economics of modern, human-based “trusted advisors” are rough. People are expensive! AI is cheap! When all else fails, here’s a self-serve dashboard for you to figure it out on your own! Oh, you have two kids, a small business, a passion for art, and you want to exercise each day? Good luck fitting it all in, but I promise you’ve got this!
I don’t have an easy answer for bringing back trusted advisors in our day-to-day personal lives. I know that cobbling together AI agents, human-in-the-loop services like Duckbill (where I’m an advisor), and an army of skilled local craftspeople and services (painters, gardeners, pool maintenance, house cleaners, a nanny) helps me feel more sane, but this is an incredibly privileged position to be in. Someday, I would love to help figure out a way to give every human access to more trusted advisors that can help them navigate the increasingly complex and stressful world we inhabit.
Startup founders might have it hardest of all. They’re surrounded by smart people, and they still don’t have a guy, because almost everyone around them has a role to play and an outcome they want. The team is great, but each person has a job to do (and a job to keep). The investors and board are often excellent too, but a board member juggling dozens of portfolio companies and an IRR target they’re expected to meet can almost never give a founder weekly, undivided attention. You need to prep for a board meeting, and fire that early-stage employee who hasn’t scaled with the business, and figure out a data issue, and somehow keep up with the latest AI tools, and approve that marketing campaign? You’ve got this!
And under all of it is the call you can’t take to anyone: whether your cofounder is still the right person, whether to take the acquisition offer, whether the VP you just hired is the problem.
That’s the one place I get to be the guy, and I love it: someone whose job isn’t on the line and whose return isn’t either, in it with them every week. If you’re a founder who could use one, here’s how I work.