Joined August 2008
65 Photos and videos
BobCasey retweeted
Tomorrow. "Do not allow the tyranny of compounding costs to overwhelm the magic of compounding returns." -Jack Bogle
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In November of 2020, @TegusHQ ran its first paid ads - as presenting sponsor of @InvestLikeBest with @patrick_oshag. Tegus co-founder Mike Elnick cut a deal with Patrick where we initially paid $20k per month ($5k per episode). We'd been growing at at a steady clip, and thought ILTB would help us get in front of more of our target customers. That was a good bet. In November of 2020 we added ~$600k in net new ARR. In December we added $1m . We attributed that to typical end-of-year software buying habits, even though it felt like half of our new inbound clients were telling us that they heard about us via the podcast. The sales kept ramping. Fast forward to February of 2021, and we had our first month of $2m in net new ARR. A few months later and we had our first $3m month. ILTB turned out to be an incredible channel. Patrick had a captive audience that perfectly overlapped with our target customers at Tegus. It was the ideal advertising channel for our product. Given our high average contract values and our strong conversion rates, we could have paid far, far more than we did initially to advertise on ILTB. In time, Patrick realized that - and we did too. Pricing increased dramatically - by 5x, then 10x, then 20x what we initially paid - yet we were very happy to pay it. @djrosent and @gilbert create incredible content. I absolutely love @AcquiredFM, and I know so many founders, CEOs and investors who feel the same way. It's unsurprising to me that they're able to command these rates. So awesome to see their success.
everyone talks about TBPN making 20M in ads, but no one talks about how @AcquiredFM is pricing their midroll at 4.7M (goddamn)
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BobCasey retweeted
Really enjoyable read. I had a chance to meet Bob and Tom in ‘23 when I was invited to Chicago HQ to give a seminar on “what’s investors do all day” Conceptually, expert network transcripts are a relatively simple business that may cause one to think “I could do that too”, but it was super apparent to me that day how locked in they were on the customer problem and how impressive of an execution machine they built to achieve that vision. Insanely nice people too. The Tegus team deserves all the success they achieved.
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14 Dec 2025
This dynamic holds in public markets just as it does in venture! Research by Hendrik Bessembinder @ASU shows that most U.S. stocks have generated lifetime returns lower than one-month T-bills. Roughly 4% of companies account for the entire net gain of the U.S. stock market since 1926, and an even smaller group (the “Mag Seven” type names) driving a disproportionate share of those returns.
13 Dec 2025
This is an insightful blog post. People who don’t understand will inevitably gravitate toward playing venture lotto (venturelotto.com). “The Power Law is what happens to your portfolio if you select for resilience, non-obviousness, and uncapped potential. It is the destination, not the map.”
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14 Dec 2025
...and one could note the importance of the same criteria in assembling a portfolio: resilience, non-obviousness, uncapped potential! The nice thing in publics vs. venture though is that there's a near-zero cost way to buy the index and ensure exposure to those outsized winners
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24 Oct 2025
Yes. I want to know how Buffett consumes his morning media diet in painstaking detail. I want to see how Zuck runs a 1:1 with Susan Li or Andrew Bosworth. I want to understand how Anna Wintour plans a weeknight dinner party. x.com/WillManidis/status/198…

great moment in the cheeky pint episode with dan sundheim where daniel presses him to walk through his average earnings morning in exhaustive detail, both w/ and w/o a crisis i wish more interviews would do this: how you do the smallest things is how you do the biggest things.
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BobCasey retweeted
3 Jun 2025
So Constellation will sell power from its Clinton IL nuclear plant to Meta starting in ‘27, who is also considering building more gigawatt scale nuclear plants for its AI power needs. Time to lift our moratorium on large nuclear construction. Now! It’s been clear the last few years that tech firms, not residents, would be the primary payers footing any nuclear construction bill. Further, what will happen when this power output is no longer available to rest of state area it services? We will need new power to replace it. Sorry, but solar storage isn’t replacing 1 GW of power here anytime soon… And we essentially have a new coal and gas ban in place. Maybe the power will come magically. Nuclear is good for the environment and our economy. Given we have interested and extremely well capitalized financiers for new plants, there couldn’t be an easier slam dunk case to allow the construction of large scale nuclear to resume here.
1 Jun 2025
I’m going to be less diplomatic than my friend Michael. Not lifting the large scale nuclear construction moratorium is an inexcusable level of stupidity and legislative mismanagement. Good way to ensure we lose out on potential industrial, technology and manufacturing investment.
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BobCasey retweeted
Affordable housing is anything but affordable! When you have units costing almost $1 million, with almost 100% of the financing coming from government, it’s time to rethink “affordable housing”
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11 Feb 2025
I think about this tweet a lot. @moizali did a great takedown of wealth management. Conflicts of interest & principal/agent problems abound. Firms push their own products. Layers of fees on fees. Advisors focus on new assets, not serving clients. And PE is rolling it all up.
3 Sep 2024
I've worked with 3 different private wealth managers over the past 5 years, including @GoldmanSachs. To date, I can say that: A. They have provided virtually no value in growing my net worth. They promise access to exclusive investment opportunities, but the investments aren't nearly as good or as exclusive as you'd think. Elliott Management has $71 Billion under management. How exclusive do you think it is? Every wealth manager pitched me "exclusive access" to Elliott. It's the fucking Vanguard of private wealth managers. Forerunner Ventures? They raised $1 billion dollars. Nothing you couldn't get access to if you really wanted/tried. But to funds you can't get access to, they can't either. Sequoia? Not a chance in hell. B. They are structured against success. You know what I want to invest in? The small scrappy guy who bought two properties in SoCal or Idaho or Oklahoma and learned how to work with contractors and flipped them. Now, he wants to buy 10 or a small apartment building and do the same. But Private Wealth Managers are all focused on acquiring and retaining large, rich clients. Why? Because their compensation is based on a percentage of money you have with them. If you have $10M invested with them, they make less than if you have $100M. So they want big fish. As a result, they can't invest in a guy raising $10M to buy real estate in Coral Gables Florida, because he's too small for them. They can only invest in the Elliots of the word. C. The idea that they are going to set you up with unique advisors who will be helpful is malarkey. The people they set you up with are run of the mill attorneys or accountants. They aren't creative. They aren't thoughtful. They aren't amazing. If they were, they'd hang up with their own shingle and make a ton of money. You think the best tax attorney works at Goldman Sachs where he makes $1m a year? He can start his own firm and make 10X that. D. They aren't smarter than you. The Private Wealth Manager I work with today forecasted a soft landing with no meaningful interest rate raises 2.5 years ago. They suggested I invest ~$10M in medium term bonds because there was 3% yield to be had and they didn't think interest rates would go up. I remember sitting in that conference room listening to them and thinking "are you fucking incompetent or insane" I invested in one fund with Colony Capital that was focused on real estate during the pandemic. It LOST money. One of the few funds to break the buck during the pandemic in real estate. And it wasn't focused on office real estate, so don't even say that. Private Wealth Manager's Ph.Ds will say "discounted cash flows" and "regression analysis" to make your head spin, and then jerk off in the dark with your money. E. The worst is Goldman Sachs though. I mean they are the fucking worst. Rather than invest in Elliott, they say "we have our own Elliott where we do the same thing but better". That may be true, but they'd say that no matter what you suggested. If @BillGates agreed to pay me a billion dollars tomorrow if I loaned him $1 today, Goldman would advise against it. Goldman would say "don't lend him the dollar - give it to us to invest instead" because then they'd earn fees on that dollar. A. If you're a PWM, tell me why I'm wrong. How are you different than other managers? Why are you better? B. Are you a client and have had a better experience with Private Wealth Managers than me? If so, please explain why? C. If you're thinking about using a PWM, I'd suggest just investing in the S&P500. What do you think?
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BobCasey retweeted
30 Jan 2025
Aldermanic prerogative is terrible for Chicago. I wrote about we can incrementally reform it over at @acitythatworks 1/n
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BobCasey retweeted
you can waste your entire life overthinking it: the window will slam shut, they will move on, your coffee will get cold, and you get tired and old. just act decisively, stop thinking so much.
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21 Dec 2024
Tonight's firing of Pedro Martinez is the most flagrant exercise of regulatory capture I've ever seen. The @ChiPubSchools Board has shown a reckless disregard for their duty to act in the best interests of the children and residents of the City of Chicago.
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21 Dec 2024
I've wondered what catalyst might drive stronger voter engagement in Chicago. 2023 mayoral elections had only 35% turnout. I think this is it. Mess with schools and people get angry. The San Francisco 2022 School Board recall is a recent example.
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5 Dec 2024
BRM saved us $100k in the first month by identifying over-provisioned software licensing @TegusHQ. Our team went from blind on software utilization to a full picture of how vendor spend was translating into usage and value. I love BRM. Proud to be an investor & early customer!
After 2 years of building, I’m excited to announce @brm_ai $21.6M Series A and Seed, led by @caffeinatedcap ($15M) and @Base10Partners ($6.6M), respectively. Our vision from Day 1 was clear: Help people buy. Buying is broken. We've all been there—frustrated and stuck, searching for the perfect tool to elevate our work. Whether it’s optimizing a marketing funnel, writing cleaner code, closing deals, or building the dream team, the right tools make all the difference. We're only as good as the tools we rely on. What did we find in our search for the perfect tool? Internally, slow disjointed processes spread across multiple departments, and archaic systems. Externally, we were bombarded with flashy marketing jargon and endless discovery calls; we wanted honesty, and clarity. We wanted the right tool to do our best work. My whole career, I’ve lived this painful experience. You probably have too. So in December of 2022, Fabian and I decided to fix it. And BRM was born. The problem set is not new. But with the advancement in AI, the solution is completely new. BRM’s AI-powered SuperAgents can now complete tasks that previously a human struggled to do. SuperAgents take on your vendors for you. SuperAgents are trained to protect your time, and protect your budget. A few SuperAgent’s from our roster to highlight Contract Collector: Finds “misplaced” contracts, and important vendor documents from your inbox. Renewal Wrangler: You will never miss a renewal again. This SuperAgent combs through all vendor documents, determining when, and if, you should renew a tool. Pricer: Helps you decide what pricing package is the best fit for your team based on your budget, and needs. Compliance Crawler: Keeps you compliant, and reduces risk through searching the web, and private documents to find, analyze and assess a vendor's compliance posture. [Agent in training]…sales people are not going to like this one! Without BRM, vendor data is spread across multiple siloed systems, and the manpower to manage those vendors is spread across Finance, Legal, Compliance, Risk, and IT. Or even worse, completely ignored. BRM provides a centralized system of record for vendor data, and a team of SuperAgents to manage them. SuperAgents are helping customers like Tegus, Public, and Cadence eliminate hundreds of hours of manual toil, and reduce spend. "With BRM it feels like we didn’t purchase software, but actually got another member of our team that always had our back." - Allison Thompson, Head of Strategic Finance at Public Pricing with BRM is simple. You pay for the vendors our SuperAgents manage. That’s it. Since we quietly began building BRM in 2022, we’ve raised $21.6M of capital. Our $15M Series A, was led by @tonsing at @caffeinatedcapital, and follows a $6M seed round led by @tjnahigian at @Base10Partners. We are also proud to have @Definition_Cap, and @friendsfamcap @0riginalCapital as strong institutional partners. Thank you to all of our investors. We have the capital to continue building a world-class team that solves hard technical problems, and delights customers. If you are attracted to our mission, join us. And if you need a team to help you buy, hire BRM’s SuperAgents. Power to the buyers, Cuddy P.S. One more thing… the vision: We don’t believe AI powered GTM tooling is going to reverse the macro trend of increasing CAC, decreasing LTV, and increasing payback periods. If every seller has these tools, how is that any different than today's GTM stack? Prior to AI it was video, mobile, data, social, sequencing, customer success, etc… they were all supposed to supplant CRM. What’s different now? What if focusing on buyers is the unlock? brm.ai/blog
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BobCasey retweeted
For no particular reason (😔) some thoughts on what a recession would look like for SaaS. To be clear, macro is above my pay grade, but I try to stay aware that recession is well within the fan of outcomes and, in the long run, inevitable. First (because it’s been so long and the pandemic was so atypical) what is a recession? A recession is basically a mind-virus doom loop about the state of the economy. For whatever reason, confidence is cracked, consumers/businesses activity defensively (cutting jobs, holding back on capex, delaying big purchases) and those cycles reinforce themselves. We’re all a part of this as human participants in the system- the median person will start confident that it is just a dip and then capitulate and buy into some secular bearish negative about the economy. Basically the same doldrums SaaS has been in, but for everything. There are some signs of that. E-commerce is soft, the labor market is soft, commercial real estate continues to look incredibly vulnerable. Enough of those cycling in sync could trigger a spiral. There’s a bull case- as Amazon said, consumers are distracted by politics and the Olympics. But there’s also a scenario where we tip into a contraction. Again, the right approach is humility- this stuff is fiendishly difficult to predict, even for the best economists. So what does that mean for SaaS? Well, the sector would enter a recession in an unusual place- out of favor already, with high rates and businesses not run in a particularly shareholder-friendly way. Despite that- make no mistake, it would be ugly. Public SaaS companies would trade at multiples that feel “silly cheap,” even as narratives emerge to justify them (expect lots of SBC talk). There would be another wave of deep job cuts, further wounding the meta-players who sell to other tech companies. At the same time, some of the sector’s counter cyclical underpinnings would start to show. 1. SaaS contracts are often mission critical- many held up during pandemic-era bankruptcies. Recurring revenue businesses trade at a premium for exactly this reason. In 2008/2009 CRM slowed down, but did still grow. 2. Lower rates help the sector quite a bit on the other side of the initial drama- PE buyers may come back in force, marginal S&M spend is more justified, multiples are theoretically higher. 3. Finally, and I say this with no joy, the sector is still run quite inefficiently and cost-cutting will likely not harm the businesses the way it would if they were run tighter today. Recessions often serve as a catalyst for corporate fitness, and SaaS companies would probably weather that quite well. No matter what, no sane person can do anything other than hope that this is another false alarm and the Fed has managed a historic soft landing. Recessions are awful.
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BobCasey retweeted
1/ This is a love letter to the Midwest. Haters gonna hate. Lovers gonna love Growing up on the East Coast, I never thought much of the Midwest. I first visited Chicago in the summer 10 years ago & was in awe. Idk if there is a city more vibrant than Chicago in the summertime
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27 Mar 2024
Going to the Berkshire AGM in May? Like this or DM me and let me know. @TegusHQ is throwing a great event in Omaha and hoping to have lots of friends there :)
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