Sales to SaaS ISVs @AWS, AI/ML co-build / GTM. Posts are personal opinions on: tech, RE & biz ownership, passionate horse racing fan, oyster farmer, Huskies fan

Seattle, WA
Joined December 2008
The short story + lessons from how I 'blew up' buying an SMB at age 43 1. 17 yrs of W2 Corp tech sales 2. Married, 3 kids 10-14 y.o. 3. Owned house, vaca home & rental 4. Living in Redmond Life is good, yes? Yes, life is good, I'm on TV! Soooo...why do this entrepreneur thing?
Replying to @jdklein33 @moizali
do you mind briefly sharing your journey in a paragraph?
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JD Klein retweeted
‡ Knightsbridge: Classic Contender or High-Class Rabbit? When Knightsbridge was declared a "go" in the Breeders' Cup Classic, there was some chatter along the lines of "fade Sovereignty, as if he were 100% they wouldn't have entered Knightsbridge". That view, to my mind, is unlikely to be correct. If Mott/Godolphin believed that Sovereignty was not at least close to 100%, I doubt very much that they would run him. The more likely explanation for the decision to enter both is that tactically they compliment one another, and the presence of Knightsbridge as a serious pace factor should benefit Sovereignty. Also, particularly given the recent loss of Medaglia d'Oro, which stood at Darley America, if Sovereignty were to win the Classic, it would catalyze further strong interest in him as an exciting new stallion prospect. Yes, Knightsbridge also has significant stud value, but he is neither a Classic winner nor a Champion, and his only Grade I win to date came at the expense of a very modest field. And given that, I would say that there is little doubt which of the two runners Godolphin would prefer to win the Classic. So, rather than thinking that Knightsbridge's entry is a negative sign for Sovereignty's chances, I view it differently. Tactically, his presence should benefit his stable-mate, and in the unlikely event that something less than a strong pace were to develop, Godolphin would have a runner that could benefit as a result. Let's assume, however, that a strong pace were to develop. Would Knightsbridge be a serious contender to win under such circumstances? I am skeptical, and partly because despite his having won a Grade I race over 10f. in his most recent start, there is evidence to suggest that he may not be as effective beyond 9f. as he is up to that distance. In the linked article below, I analyzed Knightsbridge's Pacific Classic performance, and I encourage readers who haven't read it to do so. Here's an excerpt: The pace was quite strong: 23.17 45.94 1:10.02 1:35.66 and while the winner was superficially impressive as the gap widened through the stretch, the fact is that he crawled home. These were Knightsbridge's fractions, rounded to fifths of a second: :23 1/5 :22 4/5 :24 :25 3/5 :26 3/5 That the gap between the winner and the rest of the field widened significantly over the final quarter-mile was more of a reflection of the relative weakness of Knightsbridge's opponents, than some sort of tour-de-force performance. Further underscoring the point, the 104 Beyer figure that he earned in the Pacific Classic was his slowest winning figure of any of his five Graded race wins. It is also worth noting that by far his two best performances from a speed figure standpoint came in races in which he dominated modest opponents. In fact, he has never beaten horses of anywhere near the class of Forever Young or Sovereignty, and the best horses that he has faced, Book'em Danno and Nysos, both finished ahead of him (see attached DRF PPs). Yes, he did finish ahead of Journalism in the Met Mile, but given that one's disappointing three race campaign this year, I wouldn't read much into it. Knightsbridge appears essentially to be a free-running type, but versatile enough to track the pace in a close attending position. That description also fit Fierceness, which ran a gallant second to the well set-up Sierra Leone, despite being swept in close to a very fast pace in the 2024 Classic. That he ran such fast fractions through the early and middle sections of the race is why he was beaten when stamina became paramount, and it begs very similar questions about Knightsbridge's chances on Saturday. He is now a fully mature five-year-old, and is coming off of two superficially impressive wins. I could understand why some might be tempted to take a shot, if his odds are attractive. But given the questions about his ability to stay a strongly run 10f. well, or "switch off" so that he might conserve energy for the final furlong, along with his arguably "dressed up" record of winning races against clearly inferior horses, Knightsbridge strikes me as a bet against. And while I used the expression somewhat tongue-in-cheek, I do expect him to serve essentially as a high-class rabbit (see attached image) for Sovereignty. Finally, please be sure to use the proper British pronunciation: high-clahss, to insure that Sir Knightsbridge won't be offended. 😀
‡ Knightsbridge Romps in the Pacific Classic Knightsbridge, sent off as the even-money favorite, dominated his modest opposition in the Gr. I Pacific Classic yesterday. Having battled with Full Serrano until the field straightened away in the stretch, he drew off to win by six lengths over Original Sin, which had rallied from last. The pace was quite strong: 23.17 45.94 1:10.02 1:35.66 and while the winner was superficially impressive as the gap widened through the stretch, the fact is that he crawled home. These were Knightsbridge's fractions, rounded to fifths of a second: :23 1/5 :22 4/5 :24 :25 3/5 :26 3/5 That the gap between the winner and the rest of the field widened significantly over the final quarter-mile was more of a reflection of the relative weakness of Knightsbridge's opponents, than some sort of tour-de-force performance. A good comparison would be the 2024 Breeders' Cup Classic, run over the same track. In that race, Fierceness pressed an even faster pace, ran a slightly faster final quarter, yet finished second. He was beaten because Sierra Leone was vastly superior to any of Knightsbridge's opponent's in the PC. These were Fierceness' fractions in the BCC: :22 3/5 :22 3/5 :24 2/5 :25 3/5 :26 To parse out the relative weakness (aside from the winner) of the PC field, consider that Original Sin had only previously won or placed in a single stakes race, a win in the Gr. III Blame at CD in May. Full Serrano, which to his credit continued on gamely after battling on the pace, finished third. He is a 7yo, hasn't won a stakes race of any description since 2024, and appears to be best suited to shorter distances. Om N Joy, the 4th place finisher, is a California-bred filly which previously won an open Gr. III race restricted to her own gender. That Hit Show, the 4/1 second-favorite, failed to even crack the top four places, suggests that he failed to run anywhere near his best. As it turned out, the race essentially boiled down to a match race between Knightsbridge and Full Serrano. They both ran admirably, and the best horse won. But Knightsbridge was flattered by the margin of victory, for the reasons presented above. Picking up on the earlier comparison, it appears to me that Knightsbridge and Fierceness share several important characteristics. They are/were both very fast, essentially free-running horses, though not one-dimensional. They are/were both arguably best suited to races from a mile to 9f., despite having won major races over 10f. It's also worth noting that every one of Knightsbridge's stakes victories, including the fastest, and superficially most impressive, have come over tracks that are historically "glib": Monmouth, Gulfstream and Del Mar. Some horses perform best over surfaces with high energy return, and he may well be one of them. If I happen to be correct about Knightsbridge being best suited to distances shorter than 10f., and most effective over harder surfaces, this year's Breeders' Cup Classic, which will be run at Keeneland, may not only prove to be a far stiffer test in terms of the depth of quality of the field, but also in that Knightsbridge's stamina may be tested more seriously than it was in the PC. (credit Benoit Photo via the Associated Press)
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JD Klein retweeted
Here are all the things that feel like being an entrepreneur that aren’t: Getting CIMs from brokers Listening to business podcasts Playing with Claude code or Grokbot Getting a full recourse loan Buying a course Building a new logo Negotiating a partnership agreement Hiring someone Rebuilding a website Hiring a vendor Networking Organizing a social meetup Going to conferences Building an excel model Getting a QofE done Having meetings with advisors Working on your pitch deck Bookmarking Twitter posts Opting in to a free lead magnet Writing a strategy Implementing EOS Here is what being an entrepreneur is: Making a living being paid more for something than it costs you to produce it, over and over again.
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Around half of Seattle businesses report that are considering moving or shrinking, blaming a business environment that they say is getting worse and don’t believe it looks like it will get better, according to a survey from the Downtown Seattle Association and Seattle Metropolitan Chamber of Commerce. kiro7.com/news/local/survey-…
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JD Klein retweeted
This was the moment Barack Obama broke Donald Trump. It was so bad that Trump has not experienced one second of joy since then.
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a few thoughts on running AI agents in sales, 6 months in: 1. most of the admin side of selling should be run by agents now. follow-ups, meeting prep, CRM notes, account research 2. the outbound tools I was paying for would organize outreach, track follow-up sequences, and research accounts. nowadays i’m just using Claude and slowly replacing software i don’t need 3. build lots of small agents, not one. my chief of staff is Vera, my head of content is Gus, my researcher is Scout. each one stays good at one thing 4. train a watchdog. one agent’s whole job is watching the others. every time i fix something (an email, a meeting note, how a deal got logged) the fix gets written into the rules automatically 5. build it around your best reps. the hard part of any sales team is scaling what your top performers do. write down how they prospect, run discovery and follow up, then build the agents to mirror it. now the whole team starts from their playbook 6. AI isn’t killing outbound or the SDR 7. start with one agent: the morning brief. every day it tells you what moved, who to follow up with, and what’s on the calendar. connect it to everything you use 8. talk to it. my best input isn’t a prompt, it’s a voice note on a walk. the agents sort it into tasks, posts and follow-ups by the time i’m home 9. my current approach to AI is "be the last mile" ie. it does the prospect research and email drafting, you review and send 10. we’re in the golden age of AI. the monthly plans are priced to get you hooked, and running these workflows will probably never be this cheap again
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🚨 BREAKING: Israeli ad-tech firm Discover-Tech was the top bidder on Starlink traffic in 100+ countries, Reuters reports. Trend Micro researchers concluded it was likely tracking those users. Their report codenamed it "Shadow-Earth-79" after executives raised legal concerns.
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JD Klein retweeted
Whoops.
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I’ve spoken to trainers and owners preparing for this week’s @BreedersCup, and the overwhelming theme is FRUSTRATION. Between excessive veterinary scrutiny, PET scans and scratches, what should be one of the most exciting weeks in racing has become stressful, frustrating and downright unenjoyable. I’m 100% for Thoroughbred safety, but I’m also 100% FOR THOROUGHBRED RACING!!!!! At some point, enough is enough. I’m not a veterinarian or trainer, but I listen to those who have spent 20-30 years caring for horses. One concern I keep hearing is whether restrictions on therapeutic medications and treatments are actually doing more harm than good. Could a horse with a manageable condition end up compensating and injuring something else because appropriate treatment was restricted??? ARE WE PROTECTING HORSES OR PROTECTING REGULATIONS??? Are some medication withdrawal periods unnecessarily long??? Could shortening certain periods allow better treatment without compromising safety??? And LASIX continues to make ZERO sense to me. We allow it in claiming and allowance races but prohibit it for two-year-olds and stakes horses??? Does Lasix suddenly become dangerous because the purse is bigger??? If it’s harmful, ban it everywhere. If it’s beneficial, why not allow it consistently??? OUR GOAL SHOULD BE HEALTHIER HORSES, NOT SIMPLY FEWER MEDICATIONS!!!!! And of course, let’s not forget the @jockeyclub. They helped draft the legislation behind HISA, and somehow the same familiar faces keep appearing throughout The Jockey Club, Keeneland and Breeders’ Cup leadership. Everett Dobson chairs The Jockey Club, is a Keeneland trustee and a Breeders’ Cup member. Bill Lear helped draft the legislation and is also a Keeneland trustee. DIFFERENT ORGANIZATIONS. SAME INNER CIRCLE. Amazing how much influence a small group of clowns can have over an entire industry, yet somehow accountability always seems harder to find. HISA spends approximately $80 million annually. We should demand safer racing, fewer fatalities and catching cheaters. But shouldn’t we also question whether some of these regulations are making things WORSE??? We’re already dealing with a declining foal crop, shrinking fields, frustrated horseplayers and owners wondering why they’re spending millions to participate in a sport that’s becoming less enjoyable every year. HOW MANY MORE PEOPLE DO WE NEED TO DRIVE AWAY BEFORE SOMEONE REALIZES WE HAVE A PROBLEM??? WE MUST PROTECT OUR HORSES, BUT WE ALSO NEED TO PROTECT AND GROW THE FUTURE OF THOROUGHBRED RACING. THOSE TWO OBJECTIVES SHOULD NEVER BE IN CONFLICT!!!!! Am I missing something here, or has common sense become the latest scratch??? What do you guys think???
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Huber should be muted not followed. Everything he posts is the quality of 'water is wet' except for in some of his posts, that water is actually dried intellectual sap that you try to brush away but instead, it sticks to you and your clothing, then you lose IQ points, and you can't wash the sap off, so you apply for an SBA loan to buy a landscaping business while intending to be fully employed and wind up in a pretend Twitter BJJ battle over sweaty passive I come small businesses
This guy is worth a follow. Lucid explanation of the current state of AI and where we stand. 🧐
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I said this eight years ago.
I’m gonna reiterate this again. Any financial dealings between Trump, Kushner, and Mohammed Bin Salman must come to light, and soon. We need to investigate why MBS is getting unconditional loyalty and support from Trump. #khashoggi
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They can't and shouldn't, of course. We screen for it in every deal we review (see Operator Fit section of the Viso M&A Questionnaire):
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JD Klein retweeted
According to the book, Kushner got Tillerson fired for a $50 million UAE payment because Tillerson supported Qatar. This panicked Qatar because they realized Kushner was a pay-to-play operative, so they bought Kushner's New York City apartments, which were in the red, hoping this would help.
This book is really damning for Kushner. It claims the UAE paid Kushner $50 million to get Rex Tillerson fired as Secretary of State.
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The thing about winning, it's a full time job. It's not just about game days. The preparation has to start in practice. – Tyson Chandler
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One jockey, 3 different angles from 3 different photographers Jump racing isn’t for the weak hearted 😅 📸 Todd marks, Tammie J Monaco, middleburg photo
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UPDATE: Israeli company we caught delivering zero-click infections is #1 bidder on Starlink ads in 105 countries. Data from @trendai_RSRCH suggests worldwide surveillance op targeting @Starlink users. 1/ By @razhael reuters.com/business/media-t…
🚨NEW INVESTIGATION: zero-click mercenary spyware hacking via targeted ads. A normal-looking ad loads. If you're a target, you're infected. No click needed. To protect yourself, block ads now. First time it's been confirmed in the wild. We call it #AdFection. Candiru spyware infections at @AJEnglish. 45+ devices infected. Same ad pipeline operated by Israeli company Discover-Tech reached NATO, European Parliament, dozens of gov networks & critical infrastructure incl US nuclear giant Westinghouse. Confiant, which worked with us, found signs ads were displayed at US @DeptofWar, IAEA & ICC. Investigation ongoing 1/ READ our report by @billmarczak @WolfieChristl, me Astrid Perry, Siena Anstis & Ron Deibert : citizenlab.ca/research/how-d… Confiant's blog: blog.confiant.com/p/adint-we…
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Me and other small business owners in Seattle preparing for the possibility that the repeal of the millionaires tax DOESN'T pass. DM me if you want to join us this Sunday to practice getting punched in the nuts over and over again by the Governor and the State of Washington.
If you vote "Yes," it will repeal the illegal income tax. It will not reduce funding to schools or human services because the tax doesn't go into effect until 2029. So we aren't taking anything away. Starbucks left because of this. Microsoft has threatened to move jobs out of state. Amazon now employs nearly 15,000 fewer people in Seattle than at its peak. Seattle is second to last in the number of VC deals that closed in Q3. Holding a small number of companies and rich people hostage, when they have options, is a foolish strategy that is already backfiring spectacularly. The real solution to our problems is to reduce taxes on businesses and income. Why even tax people under 25 at all? Give families with children a HUGE tax credit. Make this state an incredible place to do business and have a family. Encourage entrepreneurs to come here. Get startups, agencies, and smart, motivated people to build here. We can increase overall state revenue if more people make stuff, employ people, and create more value for everyone here. Not by chasing them out of the state and creating a hostile environment for business. Remember this: governments and taxes don't make jobs. Entrepreneurs do.
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JD Klein retweeted
I bought a business with debt because an influencer on Instagram said it was easy. They got the views. I got the loan. I watched the first video at 1 a.m. while my daughter slept down the hall. A content creator in makeup stood in front of a whiteboard: “Buy a boring business. Use the SBA. Be CEO of your life.” Hell that sounds good! THE GRAY WAVE!! It had 2.3 million views, and the thumbnail showed a laundromat with dollar signs pouring out of the dryers. I watched forty more that week. I’d been playing with Claude Code every night after work. Now I knew what it was for. I changed my LinkedIn to “Looking for one great business to buy,” like the videos said I should. I made a personal website for my holding company: Ridgeline Blue Capital. I was SURE the boomers running these companies had no idea what was possible. I’d walk in, use AI and marketing like crazy, and double the margins by Christmas. I just needed a business to do it to. I wasn’t reckless. I bought the $2,997 course and religiously finished every module. I'd join the weekly coaching calls - and take lots of notes! I wouldn't have time once I was THE CEO OF A BORING BUSINESS! I joined the paid community, where the posts were all closings and champagne: “Just got the keys!” “Month 3, already cash-flowing!” Then I found it: an HVAC company doing $1.4 million in revenue. Sure it was a bit smaller than my "buy box"! But hell, gotta start somewhere! HVAC is super hot these days, right? I saw a video on instagram. Hell, the business had been around for 20 years, and I was WAY smarter than the owner. He didn’t even go to college! I paid a CPA $18,000 for a quality-of-earnings report and paid a lawyer to read every page. My spreadsheet had three downside scenarios, and on paper I survived all of them. I was finally able to use some of the skills I'd learned at my w-2! Wow this is entrepreneurship! So I bought it. I signed a personal guarantee on a $1.6 million loan and put the house up as collateral, because the videos called that “just the price to become CEO of your life.” But it’s just content, right? The lead technician, Ray, quit in the first week. He’d thought the owner was going to hand him the business. When he found out otherwise, he left. No QoE report could have told me the business was really Ray, and that the customers were loyal to Ray. Two more techs left with him. By summer I was in crawlspaces at 9 p.m., trying to learn a trade I’d only ever seen in B-roll. I had to pay a random guy a grand a month to rent his license, just to keep the lights on. Make money? Fuck. I was just trying to make it to Friday without touching even more of my savings. I barely even understood what I'd gotten myself into... just trying to make payroll, my debt, and the lease. The letters in the mail. OH THE LETTERS IN THE MAIL. But everyone on the internet seemed to be making it work? WHAT WAS WRONG WITH ME? I finally posted in the “community.” The replies poured in. “Proud of you for sharing.” “This is the messy middle.” “Sending strength, brother.” "My brother owns a plumbing company, are you posting on facebook? Happy to connect, lmk!" Forty-seven likes. I read them in the truck and felt worse. They called it “support,” but what the fuck did that even mean? Nobody offered to cover payroll. Nobody’s wife was asking where the money went. It was my house on the line, not theirs. In the morning they’d all scroll on to the next “just got the keys!” The loan payment came out on the 1st every month. It never missed. I stopped sleeping. I stopped coming to dinner. My wife found the line of credit I’d opened to make payroll, and all the stuff I'd been shuffling on our credit cards. She didn’t yell. She said, very quietly, “You didn’t tell me,” and that was way way worse. BUT IT’S JUST CONTENT, RIGHT? I kept watching. Then I noticed something I’d missed before. At the end of each video, after forty minutes of cash flow and freedom, the influencer would glance at the camera: “Look, nobody said this was easy.” Three hundred hours of entreporn, and six seconds of reality per video. But that was the rear view mirror. I was in now. So I hid it all: the line of credit, the sleepless nights, and eventually the six-pack a night and the weed every night to get to sleep in the face of crippling anxiety. Texts from crew in the middle of the night. Unexpected bills. Calls from vendors I'd been slow paying bc I didn't have the money. I kept up a highlight reel, because that’s what the internet demanded. I changed my LinkedIn to “Acquisition Entrepreneur” so the people I went to college with would be impressed. My wife saw through it anyway. She took our daughter to her mother’s, and the house went quiet. One night I sat in the truck outside the shop and couldn’t think of a reason to drive home. I scrolled. A new post in the community: “Closed on deal #2!” Fire emojis. Everyone else seemed to be making it work. I wondered how many of them were sitting in trucks, too. BUT IT’S JUST CONTENT, RIGHT? I put the phone down. Then I picked it back up and called my brother. “I’m not okay,” I said, and my voice broke on the last word. It was the first sentence in eighteen months that wasn’t a performance. Then I looked in the mirror, honestly, for the first time in eighteen months, and said under my breath: “This guy SMBs.”
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Augie Garrido won five national titles, and these two talks show why. One after a loss, one after a comeback win 🔥
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Holy shit. Dutch intelligence has uncovered Jared Kushner’s role as a Mossad agent.
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JD Klein retweeted
The four faces that show what it’s like playing vs the Seahawks in the Mike Macdonald era
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