The trials and tribulations of sourcing, structuring, fundraising, and closing deals in the middle market.

CONUS
We closed our first deal as an independent sponsor a few weeks ago. It’s a nice service business with good margins in a niche corner of the market. We’re in at a fair price with reasonable incentives for everyone involved. If we execute, we’ll do well. You might think that I’d write a thread espousing all the tips and tricks that we used to execute this acquisition. That’s not this thread. We’ve been at this for 3.5 years and just closed our first deal. Here are all the things I wish I’d known as a non-PE guy co-founding an IS firm. I have a small audience on X, but hopefully this is valuable to a handful of folks. If not, writing this was a good exercise for me to reflect through. Sorry in advance. No sunshine and rainbows here.
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Long shot here: anyone have an escalation contact at Trimble or Spectrum? Support is completely letting us down. Entire accounting system is completely stranded. I’ve never seen anything like it. @TrimbleCorpNews
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I've been studying this extensively during our bedtime routine, and I must say, the man with the yellow hat is an absolute menace to society.
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🥈
Submitting an LOI on a proprietary deal early next week. Just got this email from the seller: "I wanted to let you know that I've brought on [[FIRM]] to act as my advisors."

ALT Shocked The Wind GIF

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Heading back from the ISF Chicago conference this morning. I continue to be surprised by the magnitude of new capital flowing into this space. Investors are tailoring structures to plug longstanding gaps in this corner of the market. It’s great and so much different now than when we started. But my goodness there are a lot of new IS firms out there. I don’t envy the job of trying to separate the wheat from the chaff. I think this will be a “winners take most” outcome. My gut says 10% of IS firms will execute 70% of deals. Or at least that feels directionally correct.
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I've found that a lot of founders believe their businesses are extremely complex. It's a symptom of keyman risk. It feels complex because the founder is doing everything. The downstream effect is resistance to implementing processes and systems.
Tom Brady's call sheet from Super Bowl LI. The 28-3 comeback. Every down, distance, and score the game could throw at him had an answer written down before kickoff. Color coded. One of the best to ever play ran one of the hardest jobs in sports off standard work. Meanwhile I still get told customer service can't have standard work. Too many variables. If it fits on one laminated sheet for the Super Bowl, it fits on one sheet for your front desk.
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SpaceX must have phenomenal PMs to get the GCs to dance like this.
Captured this drone footage yesterday. Alot of activity at the newly acquired 444 acres SpaceX site along Hwy 4 near Starbase.
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Funless Sponsor retweeted
This post looks like the start of a VERY sophisticated and well-funded PR operation to get support for Democrats to regulate AI into oblivion. Let me show you how it works: 1.) This guy, with minimal followers and no previous account activity, goes to the Wall Street Journal which publishes an exclusive with quotes from him on his resignation 18 minutes BEFORE this post goes up. Planning was clearly done in advance. 2.) Within hours, it has tens of thousands of reposts and the account has 100k+ followers. The post is punchy, quotable, it almost seems professionally written. The first three accounts to quote tweet it all do so within 15 minutes of the initial posting. Remember, this account had basically zero engagement beforehand, so an organic reach explanation seems unlikely. According to Grok those accounts are @_NathanCalvin (General Counsel at Encode AI), @peterwildeford (Head of Policy at the AI Policy Network), and @DKokotajlo (Head of the AI Futures Project), all of which are up-and-coming AI-Doomer policy advocacy nonprofits. The AI Futures Project website says it is funded “primarily” by the Survival and Flourishing Fund, which says on its own website that it has advised Jaan Tallinn, Skype creator and one of the leading investors in Anthropic, to grant over $2.5 million to the AI Futures Project since 2024. Encode AI says on its website that it is ALSO funded by the Survival and Flourishing Fund, which in turn says that it told Anthropic investor Jaan Tallinn to grant $516,000 to Encode AI in 2025. And wouldn’t you know it, the Survival and Flourishing Fund ALSO says it told Jaan Tallinn to grant $2 million to the AI Policy Institute, the 501(c)(3) affiliate of the AI Policy Network, as well. What are the odds that the first three quote tweets of Coxon’s post would all be major AI-restriction policy advocates funded generously by the same donor, who also happens to be one of the leading investors in, and a board member of, Anthropic, the company Coxon was resigning from? And all within 15 minutes of posting (two within ten)? 3.) Jacob Coxon doesn’t have much of a resume, but we do know that, in 2022, he got a $20,159 scholarship for the “long term future scholarship program” from the Good Ventures Foundation, one of the philanthropic vehicles of Dustin Moskovitz, a notorious AI-doomer who has spent tens if not hundreds of millions on policy advocacy to strictly regulate AI, while also being an Anthropic Investor himself. It also just so happens that the 14th person to quote Coxon’s post was @MaxNadeau_ (27 minutes after posting) who is the program officer for the Technical AI Safety team at Coefficient Giving, another of Moskovitz’s philanthropic spending vehicles. Max is not a frequent poster, his last posts before quoting Coxon were before Labor Day, but he was remarkably quick off the mark for this one. 4.) Basically every major Democrat politician and candidate has suddenly glommed on to this post, and conveniently, as the people cry out foe answers, Bernie Sanders already has a bill written to “ban super intelligence” and regulate AI into oblivion, and will be releasing later this week. The bill, among many other things, will create “a new cabinet-level federal agency to safeguard the public from the dangers of artificial intelligence” that will be “advised by an Artificial Intelligence Advisory Board comprised of experts on artificial intelligence.” Do you think, perhaps, Anthropic and its many investors who fund AI policy advocacy might have interest in getting to place a pet “expert” on the board of an entity that dictates what AI is and isn’t allowed to do? And isn’t it fortuitous that this whistleblower came forward with his oh-so scary stories so close in proximity to the release of the most radical piece of AI legislation ever introduced?
I resigned from Anthropic today. I spent the last three years doing pretraining research at both OpenAI and Anthropic. Neither company is acting responsibly. They are racing straight to self-improving superintelligence and gambling with our lives. More thoughts below.
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The idea that politicians would hold spending while increasing revenue is delusional.
Realistically speaking, this is the only way we will ever solve the national debt problem We can try to grow ourselves out of the problem using AI. We can try to cut spending and entitlements But think the most obvious outcome in a decade from now is that tax rates are going to be much higher than today
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So good
Replying to @NASAWatch
Few thoughts in response: 1) NASA has not given up on LEO. Within weeks of being on the job, I publicly addressed the Starliner situation and the role NASA played in it, and we have since taken a very active role with Boeing in implementing the investigation recommendations and putting Starliner on a path to life beyond Atlas V. We intend for Starliner to safely transport astronauts to and from the International Space Station, and commercial LEO destinations, in the years ahead. I actually agree that we should have more crewed transport vehicles, but how many major endeavors do you want NASA to solve simultaneously? The more NASA takes on in parallel, the less will be accomplished. And if there is considerable demand in LEO and lots of economic potential, nothing stops the companies referenced from raising capital and building vehicles. We are trying to get back to the Moon, build a base, get underway on nuclear power, launch more science missions, replace the International Space Station with a commercial service, but now we also need to fund several new crewed vehicles too? To the author’s point, nothing stopped one company from building a suborbital vehicle and operating it dozens of times without NASA as an anchor tenant, but I think market realities have spoken and the service appears to have been paused. 2) America and NASA are not giving up our astronauts, and as a commercial astronaut, I state that as emphatically and patriotically as possible. Of course, if useful research and affordable data become available as a commercial service, similarly to how we purchase and make available Earth observation data, we would have to look at it. 3) I am about as pro-commercial space as it gets, for what I hope are obvious reasons. But to be clear, you cannot simply slap the word “commercial” on every problem or opportunity, pound the table about “deleting NASA’s burdensome requirements,” and assume it automatically produces a more affordable, better solution supported by a thriving market. When people talk about relying on private capital and commercial services, someone still has to pay, a service provider has to execute really well, and if NASA is the customer, it is likely a service that has rarely been done before. If it turns out NASA is ultimately the only meaningful customer, that has the potential to become a very expensive proposition, if it works at all. 4) Premature commercialization can set both the NASA program and the emerging industry up for failure. We have seen approaches ranging from spacewalking-as-a-service to lunar-nuclear-power-as-a-service, often premised on NASA eventually being just one customer of many. Sometimes that market materializes. Many times--it is speculative. NASA, the taxpayers and the interested public should care about whatever achieves the intended mission outcome as quickly, affordably and safely as possible, and the contracting method is secondary. We can screw up cost-plus, fixed-price and as-a-service contracts just as easily. The outcomes are what matter. If, along the way, we can create a credible demand signal, help industry mature the technology and buy time for a market to develop, that is outstanding. But we should be grounded in reality rather than pretending a market already exists when it does not. 5) There are absolutely areas where the commercial model works extraordinarily well. Launch, Earth observation and communications are real services supported by real markets, and have been for decades, where NASA truly can be one customer of many. There will be more examples in the years ahead. In those cases, NASA can execute missions at lower cost and free up more of the NASA budget for the low-TRL, cutting-edge missions that have no obvious business case or revenue model, but change the world in air and space. 6) People often point to commercial crew and cargo as proof that this model works everywhere. It does not. Those programs benefited from NASA providing substantial early demand across dozens of missions, creating an opportunity for private capital to generate a return, even though I believe most did not, while also allowing an iterative design process rather than jumping immediately to the dream state. There is a big difference between maturing capabilities over a dozen cargo missions before building a no-fail crew vehicle and jumping directly to the crew vehicle, and I think the real-world data has demonstrated that. Even then, the development record across all of the crew and cargo providers was far from perfect. And today, the category leader is increasingly focused on opportunities with much larger potential markets, which should tell us something about the near-term economics of the market NASA helped create. 7) I have been very open that, in the near term, I do not know whether there is a sufficiently large LEO market where NASA can truly be one customer of many, but we will do everything within reason and within our budget to set industry up for success and ensure there is a home beyond the International Space Station. I do know demand for commercial LEO destinations will be heavily influenced by transportation cost, and those costs are likely to go up in the near term rather than down. Now, you can argue that if NASA had funded more commercial crew vehicles in years past, that would have changed the dynamic, but how many did you want for two crewed NASA missions to the ISS per year? We picked two providers, the results are apparent (for better and for worse), and clearly there was not enough supplemental commercial demand to justify further industry investment. The same uncertainty exists on the Moon. I cannot promise today that the economic value extracted from the lunar surface will exceed all of the input costs. What we can do is create a demand signal for landers, rovers, power, communications and other infrastructure, do so in a logical way that affords iterative design, and give a lunar economy every opportunity to emerge. I believe it will, but there are no guarantees. The mission is to return to the Moon and build the base for scientific, technological, national security and even inspirational reasons, and along the way, we hope enormous economic potential is unleashed. 8) If the objective is to force an economy out of every NASA endeavor, then NASA should probably sit inside the Department of Commerce. But NASA is an independent agency with a broader mission: to extend humanity’s reach farther into space, pioneer breakthrough technologies, undertake the near-impossible and unlock the secrets of the universe. While at times that is sure to leverage commercial capabilities and stimulate economic activity, it is not a prerequisite to achieving every mission.
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Fascinating
Durante los 6 años y 1 días que duró la Segunda Guerra Mundial se hundieron 15.399 barcos en los que fallecieron 567.518 marineros. Este mapa refleja todos los naufragios. Hoy en el aniversario del inicio de la Guerra rendimos un homenaje a los caídos por su sacrificio y valentía
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A little digging into his actions in the New World yields some pretty shocking stuff. Let's just say his third voyage ended with a trip back to Spain in chains.
La gesta de Colón en este vídeo es más impresionante aún
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Funless Sponsor retweeted
JUST IN: Trade unions threaten to withhold political support from candidates opposing data centers, warning thousands of blue-collar jobs could be lost.
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This is oversimplified. Texas didn't pause data center approvals due to politics. The state has 474GW of hookup requests on its desk, 90% data centers. Record peak power demand in Texas occurred this summer at 91.1GW. So what can the state do besides step on the brakes? The industry needs to bring its own power to bear and connect that production to the grid. When a data center can occasionally become a net power contributor, the narrative changes fast.
Texas, Pennsylvania and now Ohio. This is a powder keg and has the potential to unwind 200-300 basis points of annual GDP if it metastasizes. How did it get this bad? The collective leadership of frontier AI has failed miserably in doing the basics: 1. Paint a positive picture of what is possible with AI. Instead of spilling the ink on the glass half full, stories abound of pearl clutching, catastrophizing or arcane technical jargon that, together, breed mistrust, fear and skepticism. 2. Visibly and disproportionately enrich the local communities AI data centers operate in. Tell these stories with a megaphone and have local leaders lead with the financial proof so it’s irrefutable. 3. Stop infighting and stop trying to influence the government or trick them because of the asymmetric knowledge the industry has relative to outsiders and observers. This further makes it seem like a shady money grab to many bystanders. Data centers have unfortunately become THE symbolic representation of the asymmetric upside for a very narrow tech elite and a class that are untrustworthy. Inasmuch, the safer bet may be that the pushback and resistance grows…
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Funless Sponsor retweeted
I’m a plumbing company owner and I’m using Grok @bot to automate a ton of office manager work. Here’s what I’ve done in the last 24 hours:
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Few things on earth will enrage you like a HughesNet internet connection.
Half of HughesNet customers switched to Starlink. What are the other half smoking!!?!
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Agree. You must have a lane and a reason to be in that lane.
You have to earn the right to be a generalist investor… I’ll say it: most entrants into the LMM IS game should specialize in a sector or two (or perhaps a type of deal…) That is despite the fact that there is a small sliver of investors in this space that are able to generate excellent returns time and time again despite not focusing on a particular space or type of deal… Wonder at them, but it’s best not to try to replicate them in today’s competitive marketplace… Specialization remains the default for new players…don’t fight it !
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Funless Sponsor retweeted
BREAKING: Major Australian critical-minerals company @iperionx plans to redomicile in Texas, creating a new U.S.-domiciled player in the critical-minerals market. The company already operates titanium and critical-minerals facilities across the U.S.
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CBP is required to issue refunds to every company that paid the IEEPA tariffs. Ironically, Apple only raised prices after the refund was announced due to memory pricing.
When the courts overturned the tariffs they stole your money and gave it to giant corporations that hate you
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Just got an email that SBIA is publishing an independent sponsors magazine.
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Friendly reminder that Delta has a deal with Leo rolling out in '28.
Hi @Delta, I am currently on one of your planes. Can you please adopt @Starlink, because your current Wi-fi sucks. Your competitors that have Starlink can achieve speeds 100x faster than this.
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