AI is going to destroy a lot of jobs. Let’s just start there. White collar jobs. Desk jobs. The kind of jobs where your primary output is information, analysis, or words on a screen. This isn’t speculation — it’s already happening.

But here’s the thing: the world has survived every major technological disruption in history. When the power loom arrived in the early 1800s, hand weavers rioted — literally smashed the machines — because they were certain it was the end of work. It wasn’t the end of work. It was the end of that work. New work emerged that no one could have predicted, like, oh say, the commercial mass-produced clothing industry, which had even more jobs on the other side of its creation, just different jobs.

The problem is that when you’re standing in the middle of a disruption, all you can see is what it’s going to destroy. You can’t yet see what it’s going to create. That’s the cognitive trap, and we’re deep in it right now.

History Lessons: The Good, the Bad, and the Fast

Think about how poorly globalization landed in terms of job displacement. It played out over 30 years, and we still didn’t have adequate retraining programs, social safety nets, or political will to manage the transition well. Entire communities were gutted while politicians debated.

We did reasonably well with the computing revolution — probably because it created visible new industries and job categories in parallel with the ones it displaced, and because the transition was gradual enough for institutions to adapt.

But this one? This one is going to be faster. Dramatically faster. And it’s arriving in a political universe that is less equipped to handle it. Governments can barely agree on basic tech regulation (or let’s be real, much of anything), let alone coordinate workforce transitions. The policy infrastructure to manage AI-driven displacement doesn’t exist yet, and the pace of AI advancement is not waiting for Congress to catch up. That gap — between the speed of the technology and the speed of institutional response — is the real danger zone.

The Window Is Open, But It’s Closing

Elena Verna nailed it in a recent post: “AI won’t take your job. Being complacent about what’s happening around you will.” She argues there’s a short window to get radically ahead by going AI-native, and she’s right. That window is open now. It won’t be open forever.

The Wall Street Journal ran a piece recently on what young workers are doing to “AI-proof” themselves. Some are pivoting to sectors less exposed to automation. Others are doubling down on AI skills within desk-job sectors. Both are rational strategies. But here’s the main point I want to make:

AI won’t take all jobs. We will still need software developers and paralegals. But we will need far fewer of them. And if you’re worried about not getting one of those remaining jobs, not keeping the one you have, or not getting promoted as fast — your best recourse is to get really, really good at using AI.

I mean really good. Not “I ask ChatGPT questions sometimes” good.

What “Really Good” Actually Looks Like

You MUST go beyond using AI as a fancy search engine or writing assistant. Here’s what I think the bar is:

• You should be building Custom GPTs or Gems for your specific workflows
• You should use multiple LLMs and understand the practical differences between Claude, GPT, and Gemini
• You should be using Claude Cowork, the Claude Chrome Extension, and Perplexity Computer to understand how they boost application productivity
• You should experiment with the AI browsers — Atlas and Comet — and see how they change your relationship with the web
• You should vibe code a couple of applications using Lovable or Replit
• You should figure out what OpenClaw is and why it’s the hottest AI agent tool of 2026

You should be talking about all of this on your résumé, on your LinkedIn profile, and in your interviews — with concrete examples, not buzzwords. Think about it this way. If you were the hiring manager for whatever job you’re interviewing for, and you have two finalist candidates, all else equal, which one will you hire – the one who makes a joke or snarky comment about AI, or the one who very succinctly explains how she used it to save her prior employer money or created an application to help her elderly parents manage their medication more effectively?

And if all else fails and you don’t get the job you wanted as a management consultant or paralegal, well, at least you’ll have learned a ton about how to use AI. That skill set will come in handy finding something else. No matter what the purpose and the use case, this is a good investment of your time.

A Note to Employers

I want to end with something I feel strongly about: please don’t fire all your junior people just because Claude can do their job today.

Someday, you’re going to need a batch of new not-junior people. And the way you get those people is by training junior people. Junior people have to learn by doing — not only by being clever at writing prompts. You can’t skip the apprenticeship phase of a career and expect to have seasoned leaders in five years.

Yes, white collar organizations are going to look different. More like stovepipes and less like pyramids. Fewer layers, fewer people per layer, with AI handling much of the work that used to require entry-level headcount. The organizational chart of 2030 won’t look like the one from 2020. That’s okay. But we have to be intentional about not hollowing out the pipeline of human talent in the process.

I had a great networking meeting yesterday along with Tami Forman, the CEO of our non-profit affiliate Path Forward, and Joanne Wilson, my board co-chair.  It was a meeting that Joanne set up that the three of us had been talking about for over a year.  Joanne made a great comment as we were debriefing in the elevator after the meeting that is the foundation of this post.  Tami and I shaped her comment into this metaphor:

Finding wood to help start a fire is different from pouring gasoline on a fire

As an entrepreneur, you need to constantly be asking for help and networking.  Those meetings will shape your business in ways that you can never predict.  They’ll shape your thinking, add ideas to the mix, kill bad ideas, and connect you to others who can help you in your journey.

But you need to have a good sense of who to meet with, and when, along the way.  Some people, you can only meet once, unless they become core to your business, so you have to choose carefully when to fire that one bullet.  Others will meet with you regularly and are happy to see longitudinal progress.  Regardless, being clear on your ask is critical, and then backing up from that to figure out whether this is the one bullet you can fire with someone or whether it’s one ask of many will help you figure out if you should push for that networking meeting or not.

Why?

Because asking someone to help you find wood to start a fire (the early stages of your business) is different from pouring gasoline on an existing fire (once you’re up and running).  If you’re in the super early stages of your business and looking for product-market fit, you won’t want to meet with people who aren’t conceptual thinkers, who aren’t deep in your space, or who might only see you once.  Maybe they can help you brainstorm, but you’ll find better partners for that.  They might be able to provide concrete help or introductions, but you’re probably not ready for those yet.  It’s a waste of time.  You need wood to start your fire, and people like this aren’t helpful scouring the forest floor with you to find it.

However, those people can be fantastic to meet with once you have product-market fit and are deep in the revenue cycle.  You have clear demonstration of value, customer success stories, you know what works and what doesn’t and why.  You can have short, crisp asks that are easy for the person to follow-up on.  They will be willing to lend your their name and their network.  You have a fire, they have a cup of spare gasoline, and you can get them to pour that cup on your fire.

The judgment call around this isn’t easy.  Entrepreneurial zeal makes it abnormally comfortable to call on any stranger at any time and ask for help.  But developing this sense is critical to optimizing your extended network in the early years.

You've Never Seen a Girl Like This

I played hookey last night and went to a concert in San Diego — The Laura Roppe band was playing.  Laura is one of my oldest and dearest friends — we met in second grade and then went to junior high and high school together.  The title of this post is the title of her first album and its first song.  It's also true of Laura — she's one remarkable person.  Her web site is here. If you like country rock and female singer-songwriter music (think of Shania Twain or Norah Jones as comparables, although Laura is more versatile than both), and if you like discovering new up and coming artists, listen to the samples on her site, buy her album, or find her on iTunes.

I can't possibly do justice to Laura's story, which she tells very nicely on her web site here.  But the short of it is that she is in the middle of a dramatic personal transformation from brilliant lawyer to self made rock star, all while being a great mom and wife and just finishing up an exhausting 6-month successful fight against cancer.  Hopefully that's enough of a teaser to get you to at least give her music a sample!

I've been listening to her music on my ipod for months now, but especially after seeing her perform live last night, I have no doubt that she will be on an international tour within the next 12 months.  She is already getting great buzz and radio play in the US as well as Western Europe, and she's been nominated for a bunch of music awards.

I've never done a music recommendation post before in 5 years of blogging, and I may never do one again.  But Laura's story and music are just tremendous, and her lyrics are just plain fun.

My father-in-law, who is a doctor by training but now a health care executive, was recently talking about an unusual medical condition that someone in the family was fighting.  He had a wonderful expression he said docs use from time to time:

When you hear hoof beats, it’s probably horses. But you never know when it might be a zebra.

With experience (and presumably some mental wiring) comes the ability to recognize patterns.  It’s one of those things that doesn’t happen, no matter how smart you are, without the passage of time and seeing different scenarios play out in the wild.  It’s one of the big things that I’ve found that VC investors as Board members, and independent directors, bring to the Board room.  Good CEOs and senior executives will bring it to their jobs.  Good lawyers, doctors, and accountants will bring it to their professions.  If X, Y, and Z, then I am fairly certain of P, D, and Q.  Good pattern recognition allows you to make better decisions, short circuit lengthy processes, avoid mistakes, and much better understand risks.  The value of it is literally priceless.  Good pattern recognition in our business has accelerated all kinds of operational things and sparked game changing strategic thinking; it has also saved us over the years from making bad hires, making bad acquisitions, and executing poorly on everything from system implementations to process design.  Lack of pattern recognition has also cost us on a few things as well, where something seemed like a good idea but turned out not to be – but it was something no one around the Board table had any specific experience with.

But there’s a limitation, and even a downside to good pattern recognition as well.  And that is simple – pattern recognition of things in the past is not a guarantee that those same things will be true in the future.  Just because a big client’s legal or procurement team is negotiating something just like they did last time around doesn’t mean they want the same outcome this time around.  Just because you acquired a company in a new location and couldn’t manage the team remotely doesn’t mean you won’t be able to be successful doing that with another company.

The area where I worry the most about pattern recognition producing flawed results is in the area of hiring.  Unconscious bias is hard to fight, and stripping out markers that trigger unconscious bias is something everyone should try to do when interviewing/hiring – our People team is very focused on this and does a great job steering all of us around it.  But if you’re good at pattern recognition, it can cause a level of confidence that can trigger unconscious biases.  “The last person I hired out of XYZ company was terrible, so I’m inclined not to hire the next person who worked there.”  “Every time we promote someone from front-line sales into sales management, it doesn’t work out.”  You get the idea.

Because when you hear hoof beats, it’s probably horses.  But you never know when it might be a zebra!

Starbucks, Starbucks, Everywhere, Part II

In 2004, I blogged about Starbucks’ implausible Forbidden City location (post includes picture) in the heart of one of China’s most prominent national monuments.

Today, under pressure from the Chinese government, Starbucks announced that they’re closing the location, reflecting “Chinese sensitivity about cultural symbols and unease over an influx of foreign pop culture,” according to a very short blurb about this in today’s Wall Street Journal.

It must be indescribably different to live in a society that’s so tightly controlled.

Boiling the Frog

We boiled the frog recently at Return Path. 

What the heck does this mean?  There was an old story, I’ve since been told apocryphal, we told a lot back when I was a management consultant trying to work on change management projects.  It was basically that:

If you throw a frog into a pot of boiling water, it will leap right back out.  But if you put a frog in a pot of water on the stove and then heat it up to boiling, you’ll boil the frog because it never quite realized that it’s being cooked until its muscles and brain are slightly too cooked to jump out.

How have we boiled the frog?  Two ways recently.  First, we let a staffing problem sneak up on us.  We were short one person in a critical area (accounting and business operations), and we had decided to try to go without the extra person for a month or two for cost-savings reasons.  Then, another person in that group unexpectedly left.  Then, another person in that group got seriously sick and was out for several weeks.  The result?  We were down three people in an area very quickly, without a proper pipeline of candidates coming in the door for any of the open positions.  So for a period of time, we can’t get the things done out of that group we want to get done, despite the heroic efforts of the remaining people in the group.

Second, we have had an Exchange server problem that has been plaguing one of our three offices for six months now (no, the irony of an email company having internal email problems isn’t lost on us).  In retrospect, the first time we had a big problem with it, we should have dropped everything, brought in an outside consultant, and done a rapid-fire infrastructure upgrade/replacement.  But we were truly boiled here — we kept thinking we’d fixed the problem, the situation kept deteriorating slowly enough to the point where the productivity of this one office was seriously compromised for a few weeks.  Happily, I can report this weekend that our IT team is cuting over to our new environment — "the promised land," as they call it.

How do you stop yourself from getting boiled?  I think you have to:

1. Recognize when you’re in a pot of water.  What areas of your company are so mission critical that they’re always at risk?  Have you done everything you can do to eliminate single points of failure? 

2. Recognize when someone turns on the burner.  Do you know the early-warning signs for all of these areas?  Can you really live without an extra person or two in that department?  Is it ok if that server doesn’t work quite right?

3. Recognize when you care about the frog.  You can’t solve all problems, all of the time.  Figuring out which ones need to be solved urgently vs. eventually vs. never is one of the most important roles a decision-maker in a company can make.

Email Deliverability Data

We just published our 2004 year-end email deliverability report.  Feel free to download the pdf, but I’ll summarize here.  First, this report is very different from the reports you see published by Email Service Providers like Digital Impact and DoubleClick, because (a) it measures deliverability across a broad cross-section of mailers, not just a single ESP’s clients, and (b) it is a true measure of deliverability — what made it to the inbox — as opposed to the way some ESPs measure and report on deliverability, which is usually just the percentage of email that didn’t bounce or get outright blocked as spam.

Headline number one:  the “false positive” problem (non-spam ending up in the junk mailbox) is getting worse, not better.  Here’s the trend:

Full year 2004:  22%
Second half 2003:  18.7%
First half 2003:   17%
Second half 2002:  15%

Headline number two:  mailers who work on the problem can have a huge impact on their deliverability.  Obviously, I’m biased to Return Path’s own solution for mailers, but I think you can extrapolate our data to the broader universe:  companies that work on understanding, measuring, and solving the root causes of weak deliverablility can raise their inbox rate dramatically in a short time — in our study, the average improvement was a decrease in false positives from 22% to about 9% over the first three months.  But we have a number of mailers who are now closer to the 2% false positive level on a regular basis.

How Much Blogging is Too Much Blogging?

After being completely (and blissfully, I might add) offline for 11 days, I have returned to find 247 new postings in my Newsgator folder.  Only a short year ago, I would have come back from vacation to too many emails…now I get to sift through too many emails AND too many blog postings.

On the bright side, I have at least these two images of the Barolo wine country and the Amalfi coast solidly etched in my brain to ease re-entry to work. Anyone interested in a brief travelog of the Italian countryside, click here and follow the top link.

Email and Business Development: Two Great Tastes…

Interestingly, Chris Baggott offers compelling evidence for the opposite view he intended in his recent posting claiming email is not an acquisition tool.  I respect Chris as a thought leader in the email marketing services industry and am a fan of what he and his colleagues have done in building Exact Target, but I think he’s dead wrong on this one.

Email is a phenomenal customer retention tool, no question about it.  I totally agree with the claim that website owners should never let a prospect escape from their website without signing up for an email program.  It’s very true that spending money on website traffic can go to waste if a browser never buys or returns — or worse, if you pay the same search keyword fee time and time again to reach the same browser. 

However, his own post starts to lay out the reasons why email is, in fact, also really good for acquisition marketing:  because we all still love it, we spend a lot of time reading and responding to it, and we value the information it brings to us.  In short , it’s got all the strongest attributes of a great acquisition medium: reach, frequency and, most importantly, trust.  Isn’t that what advertisers look for when they are trying to figure out whether to spend their acquisition dollars in print, radio, TV, outdoor, or direct response vehicles?

In fact, more consumers and B2B professionals spend more time in their inboxes than they do consuming any other form of media — digital or not.  So, if you want to reach your target, you need to be using acquisition email.  And definitely never let a prospect come to your web site without giving you his or her email address for future contact!

Just because email is so extraordinary a retention and customer relationship tool, doesn’t exclude the reality that it also works really well to reach new prospects.  Smart marketers use email for both.

Agile Development

Sometime last year, our engineering and product teams embraced the Agile Software Development framework.  Without going into too much detail (here’s the Wikipedia entry for those who want it), the concept of Agile Development is to run software development in small pieces with a focus on more communication between product and development teams resulting in collaborative requirements development.  This leads to a “release early and often” environment where there are continual improvements.  For us, we group development projects now into a “release” that consists of a series of usually six, two-week “iterations.”

The release planning and iteration planning meetings are reasonably long meetings that involve the major stakeholders, product management and engineering.  The process also includes a very short, 10-minute Daily Stand-Up meeting with everyone on the team to review progress and identify roadblocks to completing the two-week iteration.  Requirements are not heavily documented and discussed more or less on the spot during the iteration meetings.  Because there’s a major pull-up every two weeks and a minor one every day, it’s easy to be light on requirements and for product management to constantly be in the loop with engineering to see progress, test functionality, and make mid-course corrections.

This methodology isn’t for everyone, but it’s particularly well suited to the kind of work we do at Return Path — small team, multiple internal and external stakeholders, very dynamic market, and web services as opposed to packaged software.

Our efforts have been bolstered by some limited consulting and more important, a fantastic web-based workflow management tool geared towards Agile Development run by a company called Rally Development in Boulder.  Think of it as Salesforce.com for your engineering and product team.

We’ve had great success with this methodology to date.  Engineering productivity is way up, product management visibility and input into development is way up, the level of friction/noise between product management and engineering is way down, and we have a much tighter grip on our development milestones than we ever have in the past.

Agile and Rally have worked so well for us, in fact, that we’re starting to extend the concept to other parts of our business, which I’ll write about separately.

Counter Cliche:  I Know When I See One, Too

I haven’t written a counter to one of Fred’s VC Cliche’s of the Week for a while now, but today’s was too good to resist.  While I haven’t (and most entrepreneurs haven’t) worked with 200 VCs, I have seen, heard about, been one (sort of), and worked with enough of them to know enough to comment as follows:  as is the case with Fred and entrepreneurs, I’m not sure I can define what makes a great VC in one phrase, but I know one when I see one, and here are some of the characteristics they exhibit:

– Major pattern recognition — "I’ve seen this movie before, and I know how it ends…";
– Deep understanding of the market and/or customer set to add strategic value;
– Fundamental desire to be a product manager or marketing manager of your product, but also —
– Ability to stay out of the weeds with day-to-day details when the Board meeting ends;
– Always ready with a story or bon mot about other crazy investors or even crazier entrepreneurs to make you feel better about your own life;
– Complete transparency about the motives of his/her fellow GPs and LPs and ability/appetite for follow-on financings (and needless to say, no/limited blocking of transactions that are clearly in the company’s best interests but might run counter to his/her firm’s own short-term interests);
– Willingness to jump into a debate with the strongest of convictions, yet without 100% of the facts, since 100% of the facts are never available;
– Equal willingness to admit being wrong if a clear and compelling argument comes forth; and of course the most critical —
– No fear of yielding to Management when Management knows best!
– Note — note included — major rolodex (a nice to have, but not required)

The other part of the counter cliche is that I’m sure there are some great entrepreneurs who only exhibit a few of Fred’s list of traits…much as I’m sure there are some great VCs who only exhibit a few of my list above.