From IT Leader to Storyteller: The Boss Certified Insane and the Gig Economy Playbook | Dissecting Popular IT Nerds, Episode 220

This is the complete interview from Richard Lowe’s guest appearance on episode 220 of the Dissecting Popular IT Nerds podcast, recorded October 26, 2023, lightly edited for readability.

The early-80s deep end: defragmenters, SCADA, and phone-card fraud

Richard Lowe: I was in college, trying desperately to make enough money to move out of a bad home scene, and one of my teachers started a computer company, back when computers were the size of rooms and not very powerful. I jumped at it, and within a year I was VP of consulting, running a group of eight. On that team I was project lead for the very first disk defragmenter ever written, later acquired, I believe by Raxco. When that company went under, I took two jobs at once: senior designer on the SCADA systems, systems control and data acquisition, for the Las Vegas Valley, New Haven, Connecticut, and Ojai, California water districts, monitoring the dams, sluice gates, pipes, meters, and tanks. Most of those systems are still in place today, still running some of the original code, on VAX/VMS: one written in Fortran, one rewritten in Pascal after a difficult manager left, and the Pascal one was much better.

At the same time I was VP of consulting in Long Beach with about six people, where we built a fraud detection system for phone cards, in the mid-80s, with no AI and no national database. It built a profile of your calling behavior: if you normally called from California in certain hours, to your dad in Mississippi, that passed; deviations beyond a threshold flagged the card for investigation and shutdown. Quite advanced for the time. And this was before the internet existed; one project I senior-designed was an internet precursor built on top of DEC’s DECnet, which got shelved. I hung around with the phone phreaks in those days, the guys who could whistle tones into a handset, the Captain Crunch whistle crowd, and convince the phone that money had been deposited. I was never good at it, but it was, excuse the pun, freaky to watch.

Working two jobs meant weekdays in Oxnard and weekends flying to Vegas, and it ended when I did my taxes and discovered that under pre-Reagan tax law I was netting less from two jobs than one. Good riddance: I don’t drink, smoke, or gamble, and I don’t even like the shows, so Vegas was a cold computer room in the middle of a desert with nothing to do.

Trader Joe’s: the certificate on the wall

Richard Lowe: A warehousing customer of ours connected me to Trader Joe’s, where a man named Fred hired me as director of technical services, later amended to include computer operations. The first two years were interesting: Fred had a certificate on his wall stating he was certified by a psychiatrist to be insane. He did it for employment protection: you can’t fire somebody with a disability, and he was worried about being fired. He built a wall around the department: nobody could speak to anyone outside it without him present, and he personally approved every expenditure down to a five-dollar book. It ran the arguably most important department in the company that way, the one keeping products moving to the shelves of about 40 stores. Then one morning I came in to find two sumo-wrestler types with guns; they were firing him that day and thought he’d go postal. He quit, things settled down, and I got to work for John Shields.

John Shields is my hero. Ex-CEO of Macy’s, brought in to take Trader Joe’s from $250 million to a billion, which he did; a servant leader before the term existed, all support and flowed-down authority, and it was wonderful working directly for him. He’s passed away since. After him came Dan Bane, more introverted, and the reason the company became what it is today: on the order of $15 to $20 billion a year now, privately held so nobody publishes the numbers, around 340 stores when I left and about 500 now. A nautical-themed chain people are almost cultish about; to me it was a food store with friendly people, and unfriendliness toward customers simply was not tolerated.

Digital transformation that never touches the customer

Richard Lowe: Here’s the unique thing: Trader Joe’s did digital transformation twice, and I was one of the people in charge of it before the term existed, and every bit of it was on the back end. No website ordering, no mobile app, no coupons, no loyalty programs, nothing customer-facing, because that violates what Trader Joe’s wants: a comfortable, old-fashioned store. If you proposed customer-side technology, the answer was: no, and if you think we should, you don’t understand the company culture. Meanwhile the back end grew sophisticated, because private labeling effectively made us a food manufacturing company: vendors running special production in our packaging, and eventually our own assembly lines for salads and sandwiches, shipped maybe two states out for freshness. Operations found trucks returning empty and sold that space to other companies, the backhaul play. Efficiency everywhere the customer couldn’t see it.

I was there 20 years as the point man, which meant 2 a.m. calls when computers went down and 3 a.m. calls when a buyer couldn’t sleep and couldn’t log in. I built the company’s first live hot disaster site 40 miles away, in the era when moving serious data meant having the phone company physically install T1 and T3 lines, sometimes digging them. Stores ran on satellite first, then T1s, and I’d guess it’s all internet now. I started on 110-baud teletypes; getting a T1 at 1.5 megabits once felt like the future, and now my home line is a gigabit, with everything backed into the cloud.

The presentation that had to change mid-sentence

Richard Lowe: Biggest success out of a failure: learning to communicate with C-level people. I was as hardcore a geek as you can get, shy and introverted, presenting a multi-million-dollar system we genuinely needed, and fifteen minutes in I could see it: not glazed eyes, angry eyes. They were ready to throw me out. So I switched gears mid-presentation, literally said I’m throwing away these slides, and started talking business: ROI, response times going from this to that, productivity gains by this amount. I had all the numbers all along; I just wasn’t presenting them right. The whole room changed, and the project sold. I’d been a VP twice before, so the capability existed, just rusted from years back in the technology. The lesson: business people don’t talk geek, speak the right language, and don’t be arrogant about it. Same story your consultant’s controller lived: 35 seconds a page meant nothing until it became “that’s their entire day.”

Skull Rock, shyness, and the belly dancer who broke the barrier

Richard Lowe: The role kept changing. Trader Joe’s doesn’t add main-office staff, so with the company growing around 15 percent a year, I was cutting staff, not hiring, and the grind grew. But the real story starts earlier: my wife, from Guatemala, passed away in 2005 after being sick for about twelve of our twelve and a half years, MRSA among it, with me trained to run her IVs. When she died, I caved in completely; my life had been caregiving and work. Three days after the funeral I climbed Skull Rock in Joshua Tree, and, advice: wear sunscreen, because I sat up there for eight hours, got rained on, watched the birds and a cougar, and turned red. And I decided to change my life. That was roughly ten years before I left; the seeds were planted up there.

The specific decision: break the shyness. Introversion is fine; introversion just means people drain you and solitude recharges you, and I’m an introvert. Shyness is different, and shyness is detrimental to survival, because you need to talk to people. I broke it with photography. National parks first, all over Southern California and the Southwest, then Renaissance faires, where I became an honorary Rene and their photographer; I have something like five or six hundred thousand faire photos. Then I found the belly dancers, and I was so shy I sat in the back row with a telephoto lens, posting the shots online, where the dancers found them and loved them. One day one of the dancers approached me, self-tattooed arms, piercings, utterly exotic, and I’m sitting there with every personal-space alarm firing, and she sits down, puts her arm around me, and says: Richard, we’ve watched you all faire, we love your pictures, and we would like to see you front row center from now on. She introduced me to the entire Southern California belly dance community, about a thousand dancers, and within six months I was the photographer of dancers in Southern California. Three shows a night on weekdays, faires in Ohio on the weekends, all while on call 24/7. I was having a blast and killing myself. And because I gave the photos away, the dancers threw me a birthday party every year: fifty dancers at a rented pirate ship the first time, and eventually the Monrovia community center, which seats a thousand, across two venues on two nights.

What I concluded about all of it: everybody builds a box around themselves, and the standard advice is get out of your box. I finally asked: why the hell do we need a box? At the first annual World Mermaid pageant, where I was the photographer, I checked off a bucket-list item: lunch with a supermodel. Two of them, at once, just talking. There was never anything stopping me except the belief that something was stopping me. And that’s what set me up to leave Trader Joe’s: I was terrified of starting a business, and I looked at it squarely: it’s just in my head. People start businesses all the time. I’m not going to die. Worst case, there are safety nets. Just do it. So I did.

The toolkit today: AI, eBay, and streams that spin up slowly

Richard Lowe: I wrote 60 books in the first couple of years and learned that selling books is hard; ghostwriting gives you a client and steady income. On technology today: I use LinkedIn and Facebook for lead generation, carefully, because looking like a bot gets your account killed; a client of mine did three or four hundred connections a day, bang bang bang, and LinkedIn killed the account, twice. Which is fraud detection again, the same discipline I was building for phone cards in the 80s. I don’t write with AI, but I use it constantly around the writing: just today I fed my website’s front-page text to ChatGPT, told it “you’re an SEO expert, tell me why this page isn’t generating leads, considering only the text,” and it handed me a fix list, half of it things I’d simply forgotten. Twenty bucks a month well spent. For proofreading, ProWritingAid, which I consider better than Grammarly, partly because Grammarly advertises you to death. I run ad blockers everywhere, and if Chromium really does kill ad-blocker support, I’m going to Firefox that day.

Income streams: eBay generates five or six thousand a month for me now, and selling my own accumulated junk I’ve made as much as $35,000 in a year; I’m about to invest in the drop-shipping tooling, selling at list, buying at a vendor’s sale price, shipping direct. Affiliate marketing: sell a copy of ProWritingAid under my tag and I make about fifty dollars. Photography still earns: a couple of thousand a year in digital sales, and the stock-photo sites are on this year’s plan, at three or four hundred dollars a sale for the good ones. The doctrine underneath: the economy isn’t getting worse or better, it’s changing, and one job or one gig is a single point of failure. Multiple streams mean a downturn in one pushes resources to another. But every stream takes spin-up time: eBay takes six months to build the name and learn the tricks; Uber has peak-time tricks; everything has tricks. So build the streams before you need them and idle them in maintenance mode. And hire coaches: business coach, writing coach, whatever kind. A hundred bucks an hour for a few hours changed my life, and I’ve watched six hours of writing coaching change a client’s whole trajectory. Which is occasionally galling: one current client just figured out how to turn the book I’m writing for a fixed fee into a million dollars. That part of me goes: hmm. But I’m paid what I contracted; it’s the game I’m playing.

LinkedIn work, pig butchering, and the bright shirts

Richard Lowe: The LinkedIn service: when I left Trader Joe’s, I paid a thousand dollars to have my own profile made over, and a few months later the expert called and asked me to work for her. Two years at LinkedIn Makeover, trained by her, about 300 profiles, including C-levels and ambassadors, since I’d been C-level myself and I write. Now I do it solo: several collaborative hours making your profile as good as it can be, from the About down through the skills, plus an hour or two of coaching on how to use LinkedIn and what not to do.

And a warning while we’re on the platform: the pig butchering scam, also called the romance scam. The connection request from an attractive stranger with a nearly empty new profile. The goal is thin slices of the whole pig: they build daily communication, you start to think they’re a friend, then the car’s broken and they need a few hundred, then fees, then more, and people have lost three and four hundred thousand dollars, entire life savings. These are teams: lead-generation people, communication specialists, boiler rooms. If you want to see the other side, the YouTube channel Pleasant Green catches scammers and sometimes converts them; he funded one artist’s escape from the trade with a book of her drawings that sold about $20,000, and flew to Lesotho to visit another ex-scammer. Fascinating channel.

And the bright shirts, since you asked: I used to dress boring, and then I read Larry Winget, People Are Idiots and I Can Prove It, the bulldog of personal coaches, earrings and all, and his point stuck: be yourself, because if you’re the same as everybody else, you don’t stand out, and standing out is how you make money. It’s also why my favorite masquerade exists: the Labyrinth of Jareth in Hollywood, based on the Bowie film, where all the working makeup artists and effects people come out in their real costumes. I went five years running, and one year two makeup artists couldn’t afford tickets, so I bought them, on one condition: make me Count Dracula. Full goth makeup, the best Dracula you can imagine, and they played my acolytes for two hours. It was a blast.

Closing: fix the third of your life

Richard Lowe: Find me at thewritingking.com/: around 500 articles, plus my two podcasts, Author Talks and Conversations With Influencers, and I’m on YouTube under Richard Lowe Jr. Books, blogs, case studies, white papers, fiction and nonfiction, everything from AI to franchises to how to run an apartment complex. Have you heard of KnowBe4? I rewrote their Cyber Heist book, the free download on their site; it’s one of the few I can talk about, which is the ghostwriter’s standing problem.

The closing advice: if you’re not enjoying your job, fix that, because your job is a third of your life, and with another third spent sleeping, hating work means enjoying at most a third of your life. And learn technology, because there isn’t a job left without some level of it. Take the Microsoft 365 classes; they’re fifteen bucks on Udemy. Put ChatGPT skills on top and you get a better job. Learn Access, which has become rare, and you’ve got a gig you can sell to every mom-and-pop shop. Create a Fiverr account and build gigs. Stop worrying about the economy going down and make some gigs. Like yourself, respect yourself, learn to speak, don’t be shy, and hire coaches. There’s the advice in a nutshell. And hire me to write your book.

Find Richard Lowe at thewritingking.com/.

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Part of Richard Lowe on Air, his complete run of podcast, radio, and video guest appearances.